Review Article Chemistry and Functionality of Bioactive...

14
Review Article Chemistry and Functionality of Bioactive Compounds Present in Persimmon Shazia Yaqub, Umar Farooq, Afshan Shafi, Kashif Akram, Mian Anjum Murtaza, Tusneem Kausar, and Farzana Siddique Institute of Food Science and Nutrition, University of Sargodha, Sargodha 40100, Pakistan Correspondence should be addressed to Kashif Akram; kashifakramſt@gmail.com Received 12 October 2015; Revised 4 January 2016; Accepted 14 January 2016 Academic Editor: Volker B¨ ohm Copyright © 2016 Shazia Yaqub et al. is is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. Extensive research has related the consumption of persimmon with the reduced risk of various diseases and particularly highlighted the presence of bioactive phenolic compounds for their therapeutic properties. Major phenolic compounds present in persimmon are ferulic acid, p-coumaric acid, and gallic acid. -Cryptoxanthin, lycopene, -carotene, zeaxanthin, and lutein are important carotenoids having antioxidant potential. ey are important to prevent oxidation of low-density lipoproteins, safeguard beta cells of the pancreas, and reduce cardiovascular diseases, cancer, diabetes mellitus, and damage caused by chronic alcohol consumption. In this paper, the chemistry and health benefits of bioactive compounds present in persimmon are reviewed to encourage impending applications and to facilitate further research activities. 1. Introduction Scientific research-based knowledge regarding the impact of food on human health has steered to substantial nutritional discoveries, product innovations, and mass production on an unprecedented scale [1]. e starring role of food for improving health by decreasing the risk of illness and dis- ease has highlighted a new class of foods, now known as functional foods [1, 2]. Functional foods and therapeutic agents are obtained either directly or indirectly from different natural sources. e therapeutic value of functional foods depends upon the presence of biologically active compounds (bioactive compounds). ese bioactive compounds can offer various health benefits beyond the basic nutritional value of a food product [3–6]. Recently, natural bioactive compounds have been acknowl- edged with greater consideration [3]. Fruits and vegetables are vital parts of the diet and a rich source of bioactive compounds including dietary fiber, natural antioxidants, and various phytochemicals [3, 4, 7]. e individual phytochemi- cals that have been recognized are about 5000 in number, but large numbers of them are still unknown or unidentified [8]. Most bioactive compounds (phytochemicals, phenolics, and carotenoids) are nonnutritive but effective against different diseases [9, 10] as they play important roles as chemopreven- tive or chemotherapeutic agents [11]. Among the fruits, persimmon (Diospyros kaki) is a pop- ular and widespread fruit that is enriched with many bioac- tive compounds, including polyphenols, terpenoids, steroids, flavonoids, carotenoids, minerals, and dietary fiber [6, 12]. Some components like phenolics, antioxidants, sterols, and flavonoids have a beneficial effect on human health owing to their ability to prevent or control various ailments [6, 9]. ese bioactive components play an important role in reduc- ing arterial stiffness and prevent oxidation of low-density lipoproteins (LDL) thus resulting in the prevention of athero- sclerotic plaque formation [13]. Many phytochemicals also possess antimutagenic effects and regulate and trigger the immune system, thus resulting in the normal functioning of metabolism [14]. A number of them also serve as chemo- preventive [15], anticancer, anti-inflammatory, and immuno- modulatory agents [16, 17]. Hence, persimmon, like other fruits, contains a number of functional compounds which are useful in promoting human health. is paper is aimed at appraising the chemical profile of persimmon fruit with reference to prospective bioactive components and at Hindawi Publishing Corporation Journal of Chemistry Volume 2016, Article ID 3424025, 13 pages http://dx.doi.org/10.1155/2016/3424025

Transcript of Review Article Chemistry and Functionality of Bioactive...

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Review ArticleChemistry and Functionality of Bioactive CompoundsPresent in Persimmon

Shazia Yaqub Umar Farooq Afshan Shafi Kashif Akram Mian Anjum MurtazaTusneem Kausar and Farzana Siddique

Institute of Food Science and Nutrition University of Sargodha Sargodha 40100 Pakistan

Correspondence should be addressed to Kashif Akram kashifakramftgmailcom

Received 12 October 2015 Revised 4 January 2016 Accepted 14 January 2016

Academic Editor Volker Bohm

Copyright copy 2016 Shazia Yaqub et al This is an open access article distributed under the Creative Commons Attribution Licensewhich permits unrestricted use distribution and reproduction in any medium provided the original work is properly cited

Extensive research has related the consumption of persimmonwith the reduced risk of various diseases and particularly highlightedthe presence of bioactive phenolic compounds for their therapeutic properties Major phenolic compounds present in persimmonare ferulic acid p-coumaric acid and gallic acid 120573-Cryptoxanthin lycopene 120573-carotene zeaxanthin and lutein are importantcarotenoids having antioxidant potential They are important to prevent oxidation of low-density lipoproteins safeguard beta cellsof the pancreas and reduce cardiovascular diseases cancer diabetes mellitus and damage caused by chronic alcohol consumptionIn this paper the chemistry and health benefits of bioactive compounds present in persimmon are reviewed to encourage impendingapplications and to facilitate further research activities

1 Introduction

Scientific research-based knowledge regarding the impact offood on human health has steered to substantial nutritionaldiscoveries product innovations and mass production onan unprecedented scale [1] The starring role of food forimproving health by decreasing the risk of illness and dis-ease has highlighted a new class of foods now known asfunctional foods [1 2] Functional foods and therapeuticagents are obtained either directly or indirectly from differentnatural sources The therapeutic value of functional foodsdepends upon the presence of biologically active compounds(bioactive compounds)These bioactive compounds can offervarious health benefits beyond the basic nutritional value ofa food product [3ndash6]

Recently natural bioactive compounds have been acknowl-edged with greater consideration [3] Fruits and vegetablesare vital parts of the diet and a rich source of bioactivecompounds including dietary fiber natural antioxidants andvarious phytochemicals [3 4 7] The individual phytochemi-cals that have been recognized are about 5000 in number butlarge numbers of them are still unknown or unidentified [8]Most bioactive compounds (phytochemicals phenolics and

carotenoids) are nonnutritive but effective against differentdiseases [9 10] as they play important roles as chemopreven-tive or chemotherapeutic agents [11]

Among the fruits persimmon (Diospyros kaki) is a pop-ular and widespread fruit that is enriched with many bioac-tive compounds including polyphenols terpenoids steroidsflavonoids carotenoids minerals and dietary fiber [6 12]Some components like phenolics antioxidants sterols andflavonoids have a beneficial effect on human health owingto their ability to prevent or control various ailments [6 9]These bioactive components play an important role in reduc-ing arterial stiffness and prevent oxidation of low-densitylipoproteins (LDL) thus resulting in the prevention of athero-sclerotic plaque formation [13] Many phytochemicals alsopossess antimutagenic effects and regulate and trigger theimmune system thus resulting in the normal functioning ofmetabolism [14] A number of them also serve as chemo-preventive [15] anticancer anti-inflammatory and immuno-modulatory agents [16 17] Hence persimmon like otherfruits contains a number of functional compounds whichare useful in promoting human health This paper isaimed at appraising the chemical profile of persimmon fruitwith reference to prospective bioactive components and at

Hindawi Publishing CorporationJournal of ChemistryVolume 2016 Article ID 3424025 13 pageshttpdxdoiorg10115520163424025

2 Journal of Chemistry

exploring their functionality and potential applications indisease prevention

2 Persimmon Origin and Production

The Diospyros genus belongs to the Ebenaceae family andhas more than 350 known species [12] Diospyros kaki(persimmon) also known as Japanese or oriental persimmonis a deciduous fruit originated in Eastern Asia [18] Theregions with relatively mild summer andmoderate winter arethe most suitable for its growth It is widespread in ChinaJapan and Korea where it is traditionally used for medicinalpurposes [6] Persimmon production is expanding at a rate of576annually whichmakes it the 5th fastest developing fruitcrop in the world with a current annual production of 363million metric tons [19] China is ranked first in persimmonproduction in the world with an annual production of 165million metric tons [6]

Persimmon fruits are climacteric and ethylene regulatestheir process of ripening Therefore the shelf life of per-simmon fruits can be increased by slowing the ripeningprocess by inhibiting ethylene biosynthesis or its actionhence enhancing their storage life [20 21] Persimmon iseaten as fresh or dried fruits During drying persimmonpeel is removed otherwise it produces bitter taste becauseof its astringency Usually whole fruit and slices are dried tomake dried persimmon products Juices sherbet or puree isprepared from peeled persimmon pulp However unpeeledwhole persimmon fruit can be used for persimmon vinegarand wine production [22]

3 Physical Attributes

The persimmon fruit looks like an orange red tomato with apointed end The whole fruit is edible with the exemption ofits seed and calyxThe color of the fruit varies from yellow ororange to deep red [23] depending upon the concentration ofcarotenoid contents [24] Hence higher carotenoid contentsare imperative to get maximummarket value of the fruit [2526]

4 Classification Based on Taste

The persimmon fruits are usually classified into astringent(A) and nonastringent (NA) varieties depending upon theirtaste In the early stages of development persimmon fruitsaccumulate large amounts of proanthocyanidins (PAs) inspecialized tannin cells [27] In both types of varietiesastringency decreases with maturation resulting in about70ndash90 decline in the total polyphenolic components liketannins [28] Antioxidant activities of astringent persimmonare higher as compared to nonastringent varieties [29]Astringent (A) type fruits remain rich in soluble PAs evenafter they reach the full-mature stage whereas nonastringent(NA) type fruits lose these compounds before full maturation[30]

41 Astringent Persimmon The astringency among differentvarieties of persimmonmainly depends on the concentration

of water soluble tannins [19 31] that are present in largetannin cells [32] in fruit flesh and peel and the level decreasesas the fruit matures [31]

Among different varieties Mopan (Diospyros kaki L cvMopan) is the main cultivar of astringent persimmon pro-duced in Northern China [33] especially around Beijing [34ndash36] Hachiya is another variety of persimmon that cannot beconsumed until being fully ripened because of its astringencyDuring the course of ripening soluble tannins polymerizeinto insoluble ones resulting in reduced astringency [37]Immature persimmon has proanthocyanidins (PAs) whichare about 25 (dry basis) of the fruit weight [27] Howeveron maturation this level drops below 1 [38] resulting inreduced antioxidant activity [39]

Moreover on maturation the fruit peel becomes thinand waxy having thick jellylike pulpy flesh in it [40] Largeproduction losses take place during handling of too muchsoft fruits To avoid these postharvest losses and to reduce thelevel of astringency the use of ethylene or carbon dioxide andso forth along with the selection of appropriate cultivars hasbeen recommended [41] The effectiveness of CO

2treatment

to remove astringency is based on the insolubilization oftannins by the acetaldehyde generated during anaerobicrespiration which is triggered when fruit is exposed toa high CO

2atmosphere [42] However these treatments

(ethylene carbon dioxide) can generate undesirable changesespecially a characteristic yellow-orange color due to changesin carotenoids contents Novillo et al [42] also identified anewdisorder known as ldquopinkish-bruisingrdquo in astringent per-simmon that is associated with mechanical damage duringthe postharvest handling

42 Nonastringent Persimmon Nonastringent varietiesinclude Lzu 20th century Fuyu (flat) Maekawa Jiro andFuyu Hana (pomelo) These are sweet in taste and must beeaten before full maturation otherwise they become too softto eat In nonastringent types of persimmon water solubletannins completely disappear at maturity [31] Their flesh isdark in color due to higher levels of 120573-cryptoxanthin andtotal carotenoids [43] The level of these carotenoid contentsincreases up to 554 times from the first to the last stage ofmaturity during fruit development According to findingsby Zhao et al [12] the level of carotenoid contents is higher(more than double) in nonastringent persimmons thanastringent ones at each stage of development before ripening

Fuyu is the most important nonastringent cultivar grownin Japan They have a firm peel enclosing orange-yellow fleshand have a good (sweet) taste [44]

5 Compositional Profile

51 Persimmon Fruit Persimmon fruit contains 79 water07 pectin 04 protein and crude fiber [31] It is rich invitamin A (217 RE) compared to apple (5 RE) Vitamin Ccontents vary from 75 to 70mg per 100 g of the fruit fleshdepending upon the variety [39] Some varieties are as rich assatsumamandarin and strawberry in their vitaminC contents[25] It also contains various bioactive substances (Table 1)

Journal of Chemistry 3

Table 1 Nutritional valuea per 100 g (35 oz) of persimmon fruit(Diospyros kaki raw)

Energy 293 kJ (70 kcal)Carbohydrates 1859 g

Sugars 1253 gDietary fiber 36 g

Fat 019 gSaturated 002 g

Protein 058 gRiboflavin (Vit B

2) 25mg (208)

Folate (Vit B9) 8 120583g (2)

Vitamin C 75mg (9)Calcium 8mg (1)Iron 015mg (1)Sodium 1mg (0)aPercentages are relative to US recommendations for adults (Source [45])

like vitamins (A B complex C E and K) and minerals(zinc copper iron magnesium calcium and phosphorus)that are valuable for the proper physiology of human health[45] Proanthocyanidins (PAs) are potent antioxidants andshow 20 and 50 times more activity than vitamins C and Erespectively [46]

52 Persimmon Peel The external layers of a fruit such aspeel shell and hull that shield the inside materials generallycontain enormous quantities of functional compounds [2]Regarding the persimmon peel it is considered as waste yetit is receiving much attention because of its chemical com-position [47 48]Themain constituent of peel is dietary fiber(4035ww) In addition high levels of antioxidants includ-ing vitamin C total phenolics and total carotenoids are alsopresent [49] Among the phenolic compounds caffeic acidp-coumaric acid ferulic acid and gallic acid (Figure 1) arepresent in large quantities [50 51] Proanthocyanidins (PAs)are condensed tannins that exhibit powerful antioxidantactivities These are largely present in the peel as comparedto pulp [52] The level of total carotenoids in persimmonpeel is very high (about 340mg100 g of dried peels as 120573-carotene equivalents) as compared to the peels of other fruitslike banana [53] and apple [54] Among the carotenoids 120573-cryptoxanthin is the highest (about 42) followed by zeax-anthin lutein and 120573-carotene (Figure 2) [55] The quantityof bioactive compounds (biologically active components)especially carotenoids and polyphenols is greater in thepeel compared to the pulp [50] Hence persimmon peelshould be consumed by individuals and used for industrialprocessing [47]

53 Persimmon Fruit Pulp Persimmon pulp is rich in nutri-ents such as vitamin C (70mg100 g) vitamin A (65mg100 g) calcium (9mg100 g) and iron (02mg100 g) [56] Inthe edible part (pulp) of the persimmon the major phenolicacids are ferulic acid p-coumaric acid and gallic acid and theantioxidant activity of these phenolic acids is affected by theirchemical structures (number of hydroxyl groups attached)

OOH

Gallic acid

OO

OH

Ferulic acid

OOH

p-Coumaric acid

O

O

O

Tannins

OH

OOH

Caffeic acidOH

OOH

OH

Proanthocyanidins

OH

OH

OH

OH

OHHO

HO

HO

HO

HOOH

HO

HO

HO

HO

Figure 1 Chemical structures of common phenolics in persimmon

Carotenoids are the major pigment present in persimmonThey contribute to both color and nutritional value [57ndash59] Carotenoid contents rapidly increase as green maturefruit changes to soft mature persimmon except for luteinand lycopene that decrease during fruit maturation [60]Among them 120573-cryptoxanthin content is the highest (50)followed by lycopene (10) 120573-carotene (10) zeaxanthin(5) and lutein (5) [59]They are all excellent lipid-solubleantioxidants especially lutein astaxanthin and zeaxanthinhaving the ability to scavenge free radicals in a lipid-solubleenvironment and thus preventing the oxidation of lipidsThefinal composition and concentration of carotenoid contentsare properly regulated to some extent by the different devel-opmental stages of plant tissues [61] Carotenoids identifiedin persimmon fruits are cis-mutatoxanthin antheraxanthinzeaxanthin neolutein cryptoxanthins 120572-carotene and 120573-carotene and also fatty acid esters of 120573-cryptoxanthin andzeaxanthin [62]

54 Persimmon Seeds Palmitic acid oleic acid and linoleicacid are the major fatty acids found in persimmon seedsranging from 704 to 783 of total fatty acids [63] Amongthe fatty acids oleic acid plays a role in cancer preventionThe effect of oleic acid on the same lines of breast cancer cellswas examined and it supported the theory that oleic acid ischemopreventative [64] Moreover omega-6 fatty acid (lino-leic acid) diminishes the risk of cardiovascular diseases [65]

55 Persimmon Leaves Persimmon leaves contain 4 flavo-nols [66] The leaves of persimmon have been reported to

4 Journal of Chemistry

Lycopene

H

HLutein

Zeaxanthin

120573-Cryptoxanthin

HO

OH

CH3

H3C

H3CCH3 CH3

CH3

HO

HO

CH3CH3

CH3

H3C

OH

120572-Carotene

120573-Carotene

Figure 2 Chemical structures of common carotenoids in persimmon

contain the following compounds 40-dihydroxy-a-truxillicacid tatarine C myricetin annulatin trifolin astragalinhyperin isoquercetin rutin quercetin kampferol kakispy-rone and kaki saponin [67] Leaves have been used for teain Korea since they were was thought to be effective againsthypertension [68]

6 Persimmon Bioactive Compounds

Persimmon fruit is a good source of polyphenols [69] Theterm ldquopolyphenolsrdquo includes a large group of substances andthey all have more than one phenolic hydroxyl group bound

to one or more benzene ring systems [70] The phenoliccompounds are secondary metabolites of plants [71 72] andfound in free and bound forms in persimmon fruit [73]

Persimmon phenols can be grouped as a function oftheir molecular complexityweightThus free phenolic acidscatechins and hydrolyzable tannins are included in low-molecular weight phenols while high-molecular weight phe-nols which are also called as condensed tannins or proan-thocyanidins (PAs) are large polymers of catechins with orwithout galloylation [74] One of the major componentsof condensed tannin in persimmon fruit was identified byAkagi et al [75] during compositional study of persimmon

Journal of Chemistry 5

with phloroglucinol They characterized this component asnovel epigallocatechin-3-O-gallate-phloroglucinol (EGCG-P) adduct Li et al [76] also reported that the persimmon pulpis comprised of flavan-3-O-galloylated extenders flavan-3-ol and flavonol terminal units and A-type interflavanlinkages which are condensed tannins with high-molecularweight

Structurally phenols contain an aromatic ring havinghydroxyl substituents ranging from simple to highly poly-merized compounds [77] The naturally present compoundsform linkages with saccharides and might be functionalderivatives like esters and methyl esters Hence the extensivevariety of phenolic compounds occurring in nature is theresult of this structural assortment These compounds arecategorized in several groups Out of them phenolic acidsflavonoids and tannins are considered as the main dietarycomponents [78]

Phenolic acids are non-flavonoid polyphenolic com-pounds comprised of 2 subgroups hydroxybenzoic andhydroxycinnamic acids Hydroxybenzoic acids contain gal-lic p-hydroxybenzoic protocatechuic vanillic and syringicacids in which they all have the C6ndashC1 structure Hydrox-ycinnamic acids instead are aromatic compounds like caf-feic ferulic p-coumaric and sinapic acids with a 3-carbon(C6ndashC3) side chain [78] The structure of phenolic com-pounds is a vital factor affecting radical-scavenging andmetalchelating activities and hence it is referred to as having astructurendashactivity relationship In the case of phenolic acidsthe antioxidant activity is influenced by the numbers andpositions of the hydroxyl groups with respect to the carboxylfunctional group [47] Hence they give their hydrogen atomsto scavenge free radicals as shown in Figure 1

Flavonoids have the C6ndashC3ndashC6 general structural back-bone in which the two C6 units (Ring A and Ring B) areof phenolic nature Flavonoids can be further divided intodifferent subgroups on basis of variations in chromane ringand hydroxylation pattern Flavonoids can be further dividedinto different subgroups such as anthocyanins flavan-3-olsflavones flavanones and flavonols While the vast majorityof the flavonoids have their Ring B attached to the C2position of Ring C these basic structures of flavonoids areaglycones however in plants most of these compoundsexist as glycosides Biological activities of these compoundsincluding antioxidant activity depend on both the structuralvariation and the glycosylation patterns [79]

Tannins the third important group of phenolics aresegmented as hydrolysable and condensed tannins which areesters of gallic acid and polymers of polyhydroxyflavan-3-ol monomers respectivelyThe third segment phlorotanninscomprised of phloroglucinol is found in brown algae How-ever these are insignificant regarding human diet [75 76]Tannins are present in persimmonprolonged life and reducedthe incidence of stroke in hypertensive rats [80 81]This effectwas attributed to the fact that persimmon tannins are 20 timesmore potent than antioxidant vitamin E [82]The persimmontannin is composed mostly of epicatechin epicatechin-3-O-gallate epigallocatechin and epigallocatechin-3-O-gallate[83]

7 Therapeutic Effects of Persimmon

Persimmon has been used for various medicinal purposes(Table 2) owing to the therapeutic properties such as diureticeffect blood pressure-lowering capability and the coughtreatment viral and bacterial infectious diseases [84] anddental caries [85] Various bioactive compounds includingpolyphenols carotenoids vitamins and dietary fiber in thefruit are responsible for beneficial properties [49] Subagioet al [52] reported the protective effect of proanthocyanidinfrompersimmon peel against DNAdamage and SIRT expres-sion in the aging process

The persimmon leaves are a good source of antioxidants[102] while the seed extracts have a strong radical-scavengingactivity [104] The fruits are a rich source of dietary carote-noids (a-carotene a-cryptoxanthin zeaxanthin lutein andlycopene) which have been implicated in the reduction ofdegenerative human diseases [91] The concentration of a-carotene and a-cryptoxanthin is so high that 100 g of pulpprovides 10 of the recommend daily allowance provitaminA [105]

Persimmon fruit can be used in the manufacturing ofproducts with functional characteristics because of its bioac-tive properties It is an excellent source of ascorbic acid tan-nins and carotenoids having healthy aspects owing to theirantioxidant and other health protecting activities [6]

71 Diabetes Diabetes mellitus is a chronic disease and thereason behind that is inherited andor acquired insufficientinsulin production by the pancreas or by the incompetenceof the insulin produced Such a deficiency results in raisedconcentrations of glucose in the blood which sequentiallydamage many of the bodyrsquos systems particularly the bloodvessels and nerves [106] When bodyrsquos defense systems nei-ther detoxify the reactive intermediates nor repair the result-ing damage from reactive oxygen species (ROS) then such animbalance condition is known as oxidative stress responsiblefor diabetes mellitus and related complications [107]

Along with insulin many other agents like sulfonylureaand biguanide can be used to reduce blood glucose levelin order to treat diabetes These hypoglycemic agents haveconsiderable side effects [108] In chronic diabetes thesehypoglycemic agents sometimes become ineffective [109]Therefore the demand of such hypoglycemic agents whichhave side effects and are either made artificially or fromnatural source is decreasing day by day [110] Hence there isneed of natural agents like plant and plant based materialswhich can show more potential for control and treatment ofdiabetes and its complications with no side effects [111] Sinceseveral years herbal remedies including different medicinalplants or their extracts have been taken orally in order totreat diabetes The search for effective natural hypoglycemicagent is under consideration as recommended by WHO[112] Recently great attention has been paid to a numberof nonvitamin antioxidants widely distributed in naturalsources like fruit vegetables and spices having the abilityto enhance the antioxidative defense mechanism at cellularlevel without side effects [113]Themain group of compoundsthat act primarily as free radical terminator or antioxidants isplant phenolics

6 Journal of Chemistry

Table 2 Various bioactive compounds present in persimmon and their functional properties

Source Health benefits ReferenceExtracted polyphenol119901-Coumaric Prevention of oxidative stress related diseases including diabetes [86]Tannins Scavenging action against active oxygen free radicals [82 87 88]

Tannin Assists the neuronal degeneration and karyopyknosis in cells reduction ofthickness of skin epidermis [89]

Flavonoids Scavenging action against active oxygen free radicals [82 87 88]Persimmon fruit

Whole fruit

Possesses antitumor effects due to betulinic acid [47 90]Blood pressure-lowering and diuretic effects also effective for coughs treatment [91]Has antioxidative potentials due to compounds like vitamin A beta-carotenelycopene lutein zeaxanthin and cryptoxanthin [92]

Exhibits hypolipidemic and antioxidant properties [50 82]Contains nutritional antioxidant vitamins polyphenols and dietary fiber [93 94]Reduction of patches of pigmentation on skin [95]Has ability to dilate the blood vessels near the surface of the skin thereby allowingmore blood to flow through the skin where it can be cooled by the air (antifebrile) [96]

Reduction of degenerative disease in human beings [91 97ndash99]Fruit peel powder Pharmacological potential such as antioxidant and hypocholesterolemic [51 95 100]Water-solublepolysaccharides extractedfrom persimmon fruits

Have ability to alter or regulate immune functions (immunomodulatory activity) [85]

Persimmon vinegar Has antitumor and antioxidative effects and also prevents metabolic disorderinduced by chronic alcohol administration [101]

Plant and leaf extracts

Persimmon leaf tea Prevents hardening of the arteries which ultimately lowers the blood pressure [95]Good source of natural antioxidants [102]

Persimmon plant extracts Contain antitumor and multidrug resistance-reversing agentsStop oxidative damage of DNA [47]

Persimmon calyx extracts Anticonvulsants [103]Persimmon plantsupplemented to a diet Hypocholesterolemic and antioxidative effects [82]

Persimmon seeds Contain omega 6 fatty acids like palmitic acid oleic acid and linoleic acid [63]Radical-scavenging activity [104]

Among fruits persimmon is comprised of a large numberof biologically active polyphenols like tannins and flavonoidshaving good antioxidant potential These polyphenols pre-vent the diabetes resulting from oxidative stress [86] sincethese work as antioxidants preventing the peroxidation oflipids by the donation of a hydrogen atom from hydroxylgroup attached to their chemical structure rapidly and formperoxyl radical (ROO) that ultimately leads to the formationof alkyl (aryl) hydroperoxide (ROOH) as shown in thefollowing reaction

ROOminus + PPH 997888rarr ROOH + PPminus (1)

The phenolic antioxidant (PPH) itself changes intopolyphenol phenoxyl radical (PP) which becomes stable afterdonating a hydrogen atom by conversion into quinines andit hinders the initiation of new chain reaction by reactingwith another radical inwhich another phenoxyl radical is alsoincluded [114 115]

Gorinstein et al [49] reported that a 2-week intake ofpersimmon peel supplemented diet considerably reducesfood intake blood glucose total cholesterol and plasmatriglycerides level in diabeticsThe researchers concluded thatpersimmon peel rich in high level of antioxidant and dietaryfiber with antidiabetic properties may be characterized asa possible nutritional supplement for improving diabeticcomplications and hyperglycemia

In fresh persimmon leaves most of the polyphenols arefound to be water soluble The chief components in persim-mon leaf tea are unique proanthocyanidin oligomers andoral administration of this tea along with starch resulted in adose-dependent decline in the blood glucose level in Wistarrats [116]

72 Atherosclerosis Inflammation and high levels of oxida-tive stress are a major initiator of cardiovascular diseaseslike atherosclerosis that ultimately leads to coronary artery

Journal of Chemistry 7

disease (CAD) In such condition the oxidative stress is char-acterized by the accumulation of metabolites (from the oxi-dation of proteins and lipids) and macrophages Accordingto the hypothesis of oxidative modification the early eventwhich initiates the development of atherogenesis (develop-ment of atheromatous plaques) is the oxidative breakdownof low-density lipoproteins Reactive oxygen species in thevessel wall have been considered to be one of the mostimportant causes of vascular dysfunction [117]

Dietary components having antioxidant properties as thepolyphenols are receiving a lot of attention because of theirability to reduce cardiovascular diseases [118 119] When dietrich in fiber is largely consumed it results in preventionand treatment of diverticular and coronary heart diseases[120] Coronary atherosclerosis especially is inhibited bypreventing oxidation of low-density lipoprotein (LDL) and bynutritional antioxidants like phenolics [121] and vitamins AC and E [122]

Hence many reports have shown that if intake of veg-etables and fruits is increased in diet then chances of coro-nary heart diseases could greatly be reduced [123] Accord-ing to Hertog et al [124] if 100 g of persimmon is con-sumed regularly then it will be sufficient to inhibit occlu-sion of arteries In young fruits of persimmon (Diospyroskaki) tannin is found to have the ability of bonding bile acid[83]

It has been established that addition of persimmon inthe diet hinders the increase in plasma lipid level and henceworks as antiatherosclerosis [80 124] which reduces thechances of mortality by the action of polyphenols [125]Matsumoto et al [82] also reported that the persimmon peelsupplemented diet shows hypocholesterolemic and antiox-idative effect

Total dietary fibers including soluble and insoluble totalphenolics including epicatechin gallic and p-coumaric acidsand concentrations of minerals like Na K Mg Ca Feand Mn are high in peel pulp and whole persimmon fruitcompared to apple [50] Hence persimmon must be givenpreference over apples and some other fruits in selecting anantiatherosclerotic diet Liu [126] reported decline in bloodtriglyceride and total cholesterol contents after intake ofpersimmon vinegar (PV) for 6 weeks

73 Cancer In recent years persimmon has been thefocus of attention for potential medicinal applications forprevention of cancer [47] Carotenoids are naturersquos mostwidespread pigments and have also received substantialattention because of both their provitamin and antioxidantroles [127] Carotenoids possess antioxidant properties thathave been associatedwith cellular protection [128] regulationof cell growth differentiation and apoptosis [129]

Not only are the carotenoid contents responsible forthe superficial appearance (color) and nutritional quality offruit [130] but also they provide potential health benefitsand disease prevention by quenching singlet oxygen andscavenging free radicals [131] Chemoprotective effects ofpersimmon against various forms of cancer are due to thecarotenoid contents [132 133] Persimmon was shown tobe effective in the treatment of prostate and breast cancers

[134] oral carcinoma cells [47] human lymphoid leukemiacells [135] and precancerous colon polyps in women [136]The bioactive compounds in persimmon may also affectmultidrug resistant (MDR) inhibiting activity It enhances theaccumulation of cancer cells due to the reduced activity ofefflux pumps MDR inhibitors from persimmon may helpto treat noncurable cancer because of the modulating effects[47] The calyx (persimmon) extracts act as anticonvulsantsand may alleviate the side effects of barbituric acid com-pounds [103]

8 Other Health Promoting Properties

Dried persimmon snacks were found to be effective inreducing the concentration of alcohol in the blood [55]Similarly Matsuno [137] observed that kaki-tannin foundin persimmon fruit flesh and leaves was soluble in artifi-cial stomach liquid and reduced blood alcohol (40) andacetaldehyde contents (30) Dietary intake of persimmontannin was found to prevent hypercholesterolemia in someanimal models and humans [138]

Some carotenoids present in persimmon are precur-sors of vitamin A [139] and also have immunoregulatory[140] and antiaging effects [141] Carotenoids are inverselylinked with inflammation atherosclerosis cardiovasculardiseases sarcopenia and mortality Carotenoid supplemen-tation improves the antioxidant status and reduces lipidperoxidation

Carotenoids like 120573-carotene 120572-carotene 120573-cryptoxan-thin lycopene and lutein (Figure 2) have been found to beassociated with inflammation and mortality risks [142] Inaddition lutein (carotenoids) present in persimmon peel canhelp protect eye vision [143]

9 Persimmon Leaves and Health

Persimmon leaves and extracts are being used as a greentea oriental medicines deodorants antiallergic substratesand cosmetics (especially for dermatitis) as they prevent skinproblems and have an antiwrinkle effect [68 143] and skinwhitening effect [72] The leaves are brewed into a beverageto release their antioxidant activity and antitumor effects andto inhibit angiotensin converting enzymes as well as alphaamylase [66] The leaves of persimmon possess antithrom-botic activity Arakawa et al [144] demonstrated that a 10000D anticoagulant fraction has been purified from the leavesthat inhibited thrombin-catalyzed fibrin formation with acompetitive inhibition pattern Based on their antimicrobialproperties persimmon leaf-based products have been incor-porated into athletersquos foot socks and soaps and persimmonleaves have been used as a sushi ingredient [145]

10 Unripen Persimmons and Health Issues

Bezoars are thick hard masses formed in gastrointestinaltract usually the stomach [146] Patients who have undergonestomach surgery and have delayed gastric emptying areoften more prone to the development of bezoars [147]Phytobezoars are the most common types of bezoars and

8 Journal of Chemistry

these are composed of skins seeds and vegetative matterincluding lignin cellulose hemicelluloses tannins and othernondigestible matter from fruits and vegetables ingestedDiospyrobezoars are a type of phytobezoars related to theconsumption of persimmon fruit and are common world-wide These are more difficult to treat because of their hardconsistency [146 148 149] Most bezoars in animals arecaused by hairs

When unripe astringent persimmon having a high levelof tannin is ingested a coagulum is formed in the stomachdue to the contact of tannin and shibuol with hydrochloricacid that accumulates cellulose hemicellulose and pro-tein [150] Phytobezoars may require surgical removal orendoscopic treatment as they are usually resistant to drugtreatment [151] Han et al [152] suggested a nonsurgicalapproach for cases of persimmon phytobezoar small intesti-nal obstruction with its partial dissolution of a bezoar byperforming oral and injected Coca-Cola therapy

11 Conclusion

Bioactive compounds particularly phenolics (ferulic p-coumaric and gallic acids) and carotenoids (120573-cryptoxan-thin lycopene 120573-carotene and lutein) are of major interestsin persimmon fruitThese valued bioactive components havestrong antioxidant potential which relates to the variety stageof maturity and fruit parts These functional compoundscan play a significant role in preventing and curing variousailments like diabetes hypercholesterolemia and cancerHence the known impact of natural bioactive compounds toimprove human health has introduced a substantial area ofresearch resulting in extensive advances in biochemical andnutritional sciences

Conflict of Interests

The authors declare that there is no conflict of interestsregarding the publication of this paper

References

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[2] S Yaqub U Farooq T Kausar Z Hayat M Jaskani and S MUllah ldquoHypocholestrolemic effect of persimmon peel powderin rabbitsrdquo Journal of Science International vol 25 no 3 pp605ndash609 2013

[3] M S Butt M T Sultan M Aziz et al ldquoPersimmon (Piospyroskaki) fruit hidden phytochemicals and health claimsrdquo EXCLIJournal vol 14 pp 542ndash561 2015

[4] A H A Hadi M E Duru and A B Martin-Diana ldquoBioactivenatural productsrdquo Journal of Chemistry vol 2013 Article ID208507 1 page 2013

[5] M R Segura Campos J Ruiz Ruiz L Chel-Guerrero and DBetancur Ancona ldquoCoccoloba uvifera (L)(Polygonaceae) fruitphytochemical screening and potential antioxidant activityrdquoJournal of Chemistry vol 2015 Article ID 534954 9 pages 2015

[6] S Karaman O S Toker F Yuksel M Cam A Kayacier andM Dogan ldquoPhysicochemical bioactive and sensory propertiesof persimmon-based ice cream technique for order prefer-ence by similarity to ideal solution to determine optimum con-centrationrdquo Journal of Dairy Science vol 97 no 1 pp 97ndash1102014

[7] M C Caruso F Galgano M Pecora R Tolve M Verrastroand F Favati ldquoImprovement of analytical methods for thedetermination of polyphenolic bioactive compounds in berryfruitsrdquo Journal of Chemistry vol 2015 Article ID 384051 6pages 2015

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[9] L Dauchet P Amouyel S Hercberg and J Dallongeville ldquoFruitand vegetable consumption and risk of coronary heart diseasea meta-analysis of cohort studiesrdquo Journal of Nutrition vol 136no 10 pp 2588ndash2593 2006

[10] A Denny and J Buttriss ldquoPlant foods and health focuson plant bioactivesrdquo EU 6th Framework Food Quality andSafety Thematic Priority Contract FOOD-CT-2005-513944European Food Information Resource (EuroFIR) Consortium2007

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[12] D Zhao C Zhou Y Sheng G Liang and J Tao ldquoMolecularcloning and expression of phytoene synthase lycopene beta-cyclase and beta-carotene hydroxylase genes in persimmon(Diospyros kaki L) fruitsrdquo PlantMolecular Biology Reporter vol29 no 2 pp 345ndash351 2011

[13] K Suzuki S Tsubaki M Fujita N Koyama M Takahashiand K Takazawa ldquoEffects of safflower seed extract on arterialstiffnessrdquo Vascular Health and Risk Management vol 6 no 1pp 1007ndash1014 2010

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[19] M J Li D Liang F Pu F W Ma C M Hou and T LuldquoAscorbate levels and the activity of key enzymes in ascorbatebiosynthesis and recycling in the leaves of 22 Chinese persim-mon cultivarsrdquo Scientia Horticulturae vol 120 no 2 pp 250ndash256 2009

[20] Z Luo ldquoEffect of 1-methylcyclopropene on ripening of posthar-vest persimmon (Diospyros kaki L) fruitrdquo LWTmdashFood Scienceand Technology vol 40 no 2 pp 285ndash291 2007

Journal of Chemistry 9

[21] A T Oz ldquoCombined effects of 1-methyl cyclopropene (1-MCP)andmodified atmosphere packaging (MAP) on different ripen-ing stages of persimmon fruit during storagerdquo African Journalof Biotechnology vol 10 no 5 pp 807ndash814 2011

[22] M S Akter M Ahmed and J B Eun ldquoDietary fibre compo-nents antioxidant activities and hydration properties of ripepersimmon (Diospyros kaki L cv Daebong) peel powders asaffected by different washing treatmentsrdquo International Journalof Food Science and Technology vol 45 no 7 pp 1464ndash14712010

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[30] A Ikegami T Akagi D Potter et al ldquoMolecular identifica-tion of 1-Cys peroxiredoxin and anthocyanidinflavonol 3-O-galactosyltransferase from proanthocyanidin-rich young fruitsof persimmon (Diospyros kakiThunb)rdquo Planta vol 230 no 4pp 841ndash855 2009

[31] T Radha and L Mathew Fruit Crops Horticulture ScienceSeries Jai Baharat Press 2007

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[33] X N Chen J F Fan X Yue X R Wu and L T Li ldquoRadicalscavenging activity and phenolic compounds in persimmon(Diospyros kaki L cv Mopan)rdquo Journal of Food Science vol 73no 1 pp C24ndashC28 2008

[34] H R Wang P Leng and C S Wang ldquoEffect of absorbentson storage quality of the Mopan persimmonrdquo Journal ShanxiAgriculture and Science vol 33 no 1 pp 59ndash61 2005

[35] X H Guo S Z Fang J Wang X X Guo L Q Xu and L YuanldquoStudy on the infection of the Mopan persimmon quality bycarbon dioxiderdquo Food Research Developments vol 27 pp 156ndash159 2006

[36] S Li P Zhang J K Li L Wang and Y F Huang ldquoEffect of1-methylcyclopropene for the Mopan persimmon crispiness-keeping under ambient temperaturerdquo Storing Process vol 6 pp13ndash16 2006

[37] J L Vazquez-Gutierrez I Hernando and A Quiles ldquoChangesin tannin solubility and microstructure of high hydrostaticpressurendashtreated persimmon cubes during storage at 4∘CrdquoEuropean Food Research and Technology vol 237 no 1 pp 9ndash172013

[38] N Bibi A B Khattak and ZMehmood ldquoQuality improvementand shelf life extension of persimmon fruit (Diospyros kaki)rdquoJournal of Food Engineering vol 79 no 4 pp 1359ndash1363 2007

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[40] X Wei F Liu Z Qiu Y Shao and Y He ldquoRipeness classifica-tion of astringent persimmon using hyperspectral imagingtechniquerdquo Food and Bioprocess Technology vol 7 no 5 pp1371ndash1380 2014

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2deastringency treatment on flesh disorders

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[47] W Bei W Peng Y Ma and A Xu ldquoFlavonoids from the leavesof Diospyros kaki reduce hydrogen peroxide-induced injury ofNG108-15 cellsrdquo Life Sciences vol 76 no 17 pp 1975ndash1988 2005

[48] S-O Lee S-K Chung and I-S Lee ldquoThe antidiabetic effect ofdietary persimmon (Diospyros kaki L cv sangjudungsi) peel instreptozotocin-induced daibetic ratsrdquo Journal of Food Sciencevol 71 no 3 pp S293ndashS298 2006

[49] S Gorinstein Z Zachwieja M Folta et al ldquoComparative con-tents of dietary fiber total phenolics and minerals in persim-mons and applesrdquo Journal of Agricultural and Food Chemistryvol 49 no 2 pp 952ndash957 2001

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2O2-induced cellular senescencerdquo Biolog-

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10 Journal of Chemistry

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[56] B YuanH L Xu and S P Leng ldquoContent and chemical compo-sition of carotenoids in persimmon fruitrdquo Chinese AgriculturalScience Bulletin vol 22 pp 277ndash280 2006 (Chinese)

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Journal of Chemistry 11

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[89] Y Achiwa H Hibasami H Katsuzaki K Imai and T KomiyaldquoInhibitory effects of persimmon (Diospyros kaki) extract andrelated polyphenol compounds on growth of human lymphoidleukemia cellsrdquo Bioscience Biotechnology and Biochemistry vol61 no 7 pp 1099ndash1101 1997

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[99] T Johns R L A Mahunnah P Sanaya L Chapman and TTicktin ldquoSaponins and phenolic content in plant dietary addi-tives of a traditional subsistence community the Batemi ofNgorongoro District Tanzaniardquo Journal of Ethnopharmacologyvol 66 no 1 pp 1ndash10 1999

[100] Y Zhang X Lu Y Zhang L Qin and J Zhang ldquoSulfatedmodification and immunomodulatory activity of water-solublepolysaccharides derived from fresh Chinese persimmon fruitrdquoInternational Journal of Biological Macromolecules vol 46 no1 pp 67ndash71 2010

[101] Y-J Moon and Y-S Cha ldquoEffects of persimmon-vinegar onlipid metabolism and alcohol clearance in chronic alcohol-fedratsrdquo Journal of Medicinal Food vol 11 no 1 pp 38ndash45 2008

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[103] H Itamurah N Murakami and H Nagamatsu ldquoProperty ofkaki-tannin as a functional composition in persimmon fruitflesh and leaves and its solubility in artificial stomach liquidrdquoin Proceedings of the 27th International Horticultural Congressamp Exhibition (IHC rsquo06) vol 8 pp 265ndash267 August 2006

[104] K A Steinmetz and J D Potter ldquoVegetables fruit and cancerprevention a reviewrdquo Journal of the American Dietetic Associa-tion vol 96 no 10 pp 1027ndash1039 1996

[105] A N Nagappa P A Thakurdesai N V Rao and J SinghldquoAntidiabetic activity ofTerminalia catappa Linn fruitsrdquo Journalof Ethnopharmacology vol 88 no 1 pp 45ndash50 2003

[106] K Datta S Sinha and P Chattopadhyay ldquoReactive oxygenspecies in health and diseaserdquoNationalMedical Journal of Indiavol 13 no 6 pp 304ndash310 2000

[107] R R Holman and R C Turner ldquoOral agents and insulin in thetreatment of NIDDMrdquo in Textbook of Diabetes J Williams Edpp 407ndash469 Blackwell Press Oxford UK 1991

[108] F Giacco and M Brownlee ldquoOxidative stress and diabeticcomplicationsrdquo Circulation Research vol 107 no 9 pp 1058ndash1070 2010

[109] B K Rao M M Kesavulu R Giri and C A Rao ldquoAntidiabeticand hypolipidemic effects ofMomordicacymbalariaHook fruitpowder in alloxan-diabetic ratsrdquo Journal of Ethnopharmacologyvol 67 no 1 pp 103ndash109 1999

[110] J K Grover V Vats V Rathi and S S Dawar ldquoTraditionalIndian anti-diabetic plants attenuate progression of renal dam-age in streptozotocin induced diabetic micerdquo Journal of Ethno-pharmacology vol 76 no 3 pp 233ndash238 2001

[111] R K Gupta A N Kesari P S Murthy R Chandra V Tandonand GWatal ldquoHypoglycemic and antidiabetic effect of ethano-lic extract of leaves of Annona squamosa L in experimentalanimalsrdquo Journal of Ethnopharmacology vol 99 no 1 pp 75ndash81 2005

[112] S Gupta N Ahmad A-L Nieminen andHMukhtar ldquoGrowthinhibition cell-cycle dysregulation and induction of apopto-sis by green tea constituent (-)-epigallocatechin-3-gallate inandrogen-sensitive and androgen-insensitive human prostatecarcinoma cellsrdquoToxicology andApplied Pharmacology vol 164no 1 pp 82ndash90 2000

[113] T Yokozawa Y A Kim H Y Kim Y A Lee and G-I NonakaldquoProtective effect of persimmon peel polyphenol against highglucose-induced oxidative stress in LLC-PK1 cellsrdquo Food andChemical Toxicology vol 45 no 10 pp 1979ndash1987 2007

12 Journal of Chemistry

[114] M S Brewer ldquoNatural antioxidants sources compoundsmechanisms of action and potential applicationsrdquo Comprehen-sive Reviews in Food Science and Food Safety vol 10 no 4 pp221ndash247 2011

[115] K Kawakami H Nishida N Tatewaki Y Nakajima T Konishiand M Hirayama ldquoPersimmon leaf extract inhibits the ATMactivity during DNA damage response induced by Doxorubicinin A549 lung adenocarcinoma cellsrdquo Bioscience Biotechnologyand Biochemistry vol 75 no 4 pp 650ndash655 2011

[116] D Steinberg S Parthasarathy T E Carew J C Khoo and JL Witztum ldquoBeyond cholesterol modifications of low-densitylipoprotein that increase its atherogenicityrdquo The New EnglandJournal of Medicine vol 320 no 14 pp 915ndash924 1989

[117] P M Kris-Etherton and C L Keen ldquoEvidence that the anti-oxidant flavonoids in tea and cocoa are beneficial for cardiovas-cular healthrdquo Current Opinion in Lipidology vol 13 no 1 pp41ndash49 2002

[118] C Manach A Mazur and A Scalbert ldquoPolyphenols and pre-vention of cardiovascular diseasesrdquo Current Opinion in Lipidol-ogy vol 16 no 1 pp 77ndash84 2005

[119] J W Anderson B M Smith and N J Gustafson ldquoHealthbenefits and practical aspects of high-fiber dietsrdquo AmericanJournal of Clinical Nutrition vol 59 no 5 pp 1242ndash1247 1994

[120] D Kromhout A Menotti H Kesteloot and S Sans ldquoPreven-tion of coronary heart disease by diet and lifestyle evidencefrom prospective cross-cultural cohort and intervention stud-iesrdquo Circulation vol 105 no 7 pp 893ndash898 2002

[121] E B Rimm M J Stampfer A Ascherio E Giovannucci G AColditz andWCWillett ldquoVitamin E consumption and the riskof coronary heart disease in menrdquo The New England Journal ofMedicine vol 328 no 20 pp 1450ndash1456 1993

[122] L Dauchet J Ferrieres D Arveiler et al ldquoFrequency of fruitand vegetable consumption and coronary heart disease inFrance and Northern Ireland the prime studyrdquo British Journalof Nutrition vol 92 no 6 pp 963ndash972 2004

[123] S Gorinstein GW Kulasek E Bartnikowska et al ldquoThe effectsof diets supplementedwith either whole persimmon or phenol-free persimmon on rats fed cholesterolrdquo Food Chemistry vol70 no 3 pp 303ndash308 2000

[124] M G L Hertog E J M Feskens P C H HollmanM B Katanand D Kromhout ldquoDietary antioxidant flavonoids and risk ofcoronary heart disease the Zutphen Elderly studyrdquoThe Lancetvol 342 no 8878 pp 1007ndash1011 1993

[125] H Seo B D Jeon andR Sungpil ldquoPersimmon vinegar ripeningwith the mountain-cultivated ginseng ingestion reduces bloodlipids and lowers inflammatory cytokines in obese adolescentsrdquoJournal of Exercise Nutrition and Biochemistry vol 19 no 1 pp1ndash10 2015

[126] R H Liu ldquoPotential synergy of phytochemicals in cancerprevention mechanism of actionrdquo Journal of Nutrition vol 134no 12 supplement pp 3479Sndash3485S 2004

[127] S T Mayne ldquoAntioxidant nutrients and chronic disease use ofbiomarkers of exposure and oxidative stress status in epidemi-ologic researchrdquo Journal of Nutrition vol 133 no 3 pp 933sndash940s 2003

[128] H Tapiero D M Townsend and K D Tew ldquoThe role of caro-tenoids in the prevention of human pathologiesrdquo Biomedicineand Pharmacotherapy vol 58 no 2 pp 100ndash110 2004

[129] J Tao and S L Zhang ldquoMetabolismof carotenoid and its regula-tion in garden croprdquo Journal of Zhejiang University (Agricultureamp Life Sciences) vol 29 pp 585ndash590 2003

[130] W Miki ldquoBiological functions and activities of animal caro-tenoidsrdquo Pure and Applied Chemistry vol 63 no 1 pp 141ndash1461991

[131] H Fujiki ldquoGreen tea health benefits as cancer preventive forhumansrdquo Chemical Record vol 5 no 3 pp 119ndash132 2005

[132] A P George and S Redpath ldquoHealth and medicinal benefits ofpersimmon fruit a reviewrdquo Advances in Horticultural Sciencevol 22 no 4 pp 244ndash249 2008

[133] T Hussain S Gupta V M Adhami and H Mukhtar ldquoGreentea constituent epigallocatechin-3-gallate selectively inhibitsCOX-2 without affecting COX-1 expression in human prostatecarcinoma cellsrdquo International Journal of Cancer vol 113 no 4pp 660ndash669 2005

[134] Y-C Wang and U Bachrach ldquoThe specific anti-cancer activityof green tea (minus)-epigallocatechin-3-gallate (EGCG)rdquo AminoAcids vol 22 no 2 pp 131ndash143 2002

[135] O Takayuki ldquoPersimmons your healthy autumn treatsrdquoAsahikawa Information vol 108 pp 1ndash2 2005

[136] T Fukuda and H Shibata ldquoPersimmon calyx extracts as anti-convulsants and to alleviate the side effects of barbituric acidcompoundsrdquo Patent Japanease Kokai Tokkyo Koho vol 6 pp649ndash653 1994

[137] T Matsuno ldquoXanthophylls as precursors of retinoidsrdquo Pure andApplied Chemistry vol 63 no 1 pp 81ndash88 1991

[138] N Gato A Kadowaki N Hashimoto S-I Yokoyama and KMatsumoto ldquoPersimmon fruit tannin-rich fiber reduces choles-terol levels in humansrdquoAnnals of Nutrition andMetabolism vol62 no 1 pp 1ndash6 2013

[139] A Nagao ldquoAbsorption and function of dietary carotenoidsrdquoForum of Nutrition vol 61 pp 55ndash63 2009

[140] PD Fraser andPM Bramley ldquoThebiosynthesis andnutritionaluses of carotenoidsrdquo Progress in Lipid Research vol 43 no 3 pp228ndash265 2004

[141] D Fusco G Colloca M R Lo Monaco and M Cesari ldquoEffectsof antioxidant supplementation on the aging processrdquo ClinicalInterventions in Aging vol 2 no 3 pp 377ndash387 2007

[142] JM Seddon U Ajan and R D Sperduto ldquoDietary carotenoidsvitamins A C and E and advance age-related macular degen-eration Eye Disease Case Study Grouprdquo Journal of AmericanMedical Association vol 272 no 18 pp 1413ndash1420 1992

[143] B-J An J-H Kwak J-M Park et al ldquoInhibition of enzymeactivities and the antiwrinkle effect of polyphenol isolated fromthe persimmon leaf (Diospyros kaki folium) on human skinrdquoDermatologic Surgery vol 31 no 7 pp 848ndash854 2005

[144] H Arakawa M Takasaki N Tajima H Fukamachi and TIgarashi ldquoAntibacterial activities of persimmon extracts relatewith their hydrogen peroxide concentrationrdquo Biological andPharmaceutical Bulletin vol 37 no 7 pp 1119ndash1123 2014

[145] S D Ladas D Kamberoglou G Karamanolis J Vlachogian-nakos and I Zouboulis-Vafiadis ldquoSystematic review Coca-Cola can effectively dissolve gastric phytobezoars as a first-linetreatmentrdquo Alimentary Pharmacology and Therapeutics vol 37no 2 pp 169ndash173 2013

[146] T J Cifuentes C R Robles P P Parrilla et al ldquoPolyphenols andhealth what compounds are involvedrdquo Nutrition Metabolismand Cardiovascular Diseases vol 20 no 1 pp 1ndash6 2010

[147] J Gaya L Barranco A Llompart J Reyes and A ObradorldquoPersimmon bezoars a successful combined therapyrdquoGastroin-testinal Endoscopy vol 55 no 4 pp 581ndash583 2002

[148] P G Hayes and O D Rotstein ldquoGastrointestinal phytobezoarspresentation and managementrdquo Canadian Journal of Surgeryvol 29 no 6 pp 419ndash420 1986

Journal of Chemistry 13

[149] MM Krausz E ZMoriel A Ayalon D Pode and A L DurstldquoSurgical aspects of gastrointestinal persimmon phytobezoartreatmentrdquoThe American Journal of Surgery vol 152 no 5 pp526ndash530 1986

[150] P Walker-Renard ldquoUpdate on the medicinal management ofphytobezoarsrdquo The American Journal of Gastroenterology vol88 no 10 pp 1663ndash1666 1993

[151] S S Ha H S LeeM K Jung et al ldquoAcute intestinal obstructioncaused by a persimmon phytobezoar after dissolution therapywith Coca-Colardquo The Korean Journal of Internal Medicine vol22 no 4 pp 300ndash303 2007

[152] J Han S Kang R Choue et al ldquoFree radical scavenging effectofDiospyros kaki Laminaria japonica andUndaria pinnatifidardquoFitoterapia vol 73 no 7-8 pp 710ndash712 2002

Submit your manuscripts athttpwwwhindawicom

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Page 2: Review Article Chemistry and Functionality of Bioactive ...downloads.hindawi.com/journals/jchem/2016/3424025.pdf · Review Article Chemistry and Functionality of Bioactive Compounds

2 Journal of Chemistry

exploring their functionality and potential applications indisease prevention

2 Persimmon Origin and Production

The Diospyros genus belongs to the Ebenaceae family andhas more than 350 known species [12] Diospyros kaki(persimmon) also known as Japanese or oriental persimmonis a deciduous fruit originated in Eastern Asia [18] Theregions with relatively mild summer andmoderate winter arethe most suitable for its growth It is widespread in ChinaJapan and Korea where it is traditionally used for medicinalpurposes [6] Persimmon production is expanding at a rate of576annually whichmakes it the 5th fastest developing fruitcrop in the world with a current annual production of 363million metric tons [19] China is ranked first in persimmonproduction in the world with an annual production of 165million metric tons [6]

Persimmon fruits are climacteric and ethylene regulatestheir process of ripening Therefore the shelf life of per-simmon fruits can be increased by slowing the ripeningprocess by inhibiting ethylene biosynthesis or its actionhence enhancing their storage life [20 21] Persimmon iseaten as fresh or dried fruits During drying persimmonpeel is removed otherwise it produces bitter taste becauseof its astringency Usually whole fruit and slices are dried tomake dried persimmon products Juices sherbet or puree isprepared from peeled persimmon pulp However unpeeledwhole persimmon fruit can be used for persimmon vinegarand wine production [22]

3 Physical Attributes

The persimmon fruit looks like an orange red tomato with apointed end The whole fruit is edible with the exemption ofits seed and calyxThe color of the fruit varies from yellow ororange to deep red [23] depending upon the concentration ofcarotenoid contents [24] Hence higher carotenoid contentsare imperative to get maximummarket value of the fruit [2526]

4 Classification Based on Taste

The persimmon fruits are usually classified into astringent(A) and nonastringent (NA) varieties depending upon theirtaste In the early stages of development persimmon fruitsaccumulate large amounts of proanthocyanidins (PAs) inspecialized tannin cells [27] In both types of varietiesastringency decreases with maturation resulting in about70ndash90 decline in the total polyphenolic components liketannins [28] Antioxidant activities of astringent persimmonare higher as compared to nonastringent varieties [29]Astringent (A) type fruits remain rich in soluble PAs evenafter they reach the full-mature stage whereas nonastringent(NA) type fruits lose these compounds before full maturation[30]

41 Astringent Persimmon The astringency among differentvarieties of persimmonmainly depends on the concentration

of water soluble tannins [19 31] that are present in largetannin cells [32] in fruit flesh and peel and the level decreasesas the fruit matures [31]

Among different varieties Mopan (Diospyros kaki L cvMopan) is the main cultivar of astringent persimmon pro-duced in Northern China [33] especially around Beijing [34ndash36] Hachiya is another variety of persimmon that cannot beconsumed until being fully ripened because of its astringencyDuring the course of ripening soluble tannins polymerizeinto insoluble ones resulting in reduced astringency [37]Immature persimmon has proanthocyanidins (PAs) whichare about 25 (dry basis) of the fruit weight [27] Howeveron maturation this level drops below 1 [38] resulting inreduced antioxidant activity [39]

Moreover on maturation the fruit peel becomes thinand waxy having thick jellylike pulpy flesh in it [40] Largeproduction losses take place during handling of too muchsoft fruits To avoid these postharvest losses and to reduce thelevel of astringency the use of ethylene or carbon dioxide andso forth along with the selection of appropriate cultivars hasbeen recommended [41] The effectiveness of CO

2treatment

to remove astringency is based on the insolubilization oftannins by the acetaldehyde generated during anaerobicrespiration which is triggered when fruit is exposed toa high CO

2atmosphere [42] However these treatments

(ethylene carbon dioxide) can generate undesirable changesespecially a characteristic yellow-orange color due to changesin carotenoids contents Novillo et al [42] also identified anewdisorder known as ldquopinkish-bruisingrdquo in astringent per-simmon that is associated with mechanical damage duringthe postharvest handling

42 Nonastringent Persimmon Nonastringent varietiesinclude Lzu 20th century Fuyu (flat) Maekawa Jiro andFuyu Hana (pomelo) These are sweet in taste and must beeaten before full maturation otherwise they become too softto eat In nonastringent types of persimmon water solubletannins completely disappear at maturity [31] Their flesh isdark in color due to higher levels of 120573-cryptoxanthin andtotal carotenoids [43] The level of these carotenoid contentsincreases up to 554 times from the first to the last stage ofmaturity during fruit development According to findingsby Zhao et al [12] the level of carotenoid contents is higher(more than double) in nonastringent persimmons thanastringent ones at each stage of development before ripening

Fuyu is the most important nonastringent cultivar grownin Japan They have a firm peel enclosing orange-yellow fleshand have a good (sweet) taste [44]

5 Compositional Profile

51 Persimmon Fruit Persimmon fruit contains 79 water07 pectin 04 protein and crude fiber [31] It is rich invitamin A (217 RE) compared to apple (5 RE) Vitamin Ccontents vary from 75 to 70mg per 100 g of the fruit fleshdepending upon the variety [39] Some varieties are as rich assatsumamandarin and strawberry in their vitaminC contents[25] It also contains various bioactive substances (Table 1)

Journal of Chemistry 3

Table 1 Nutritional valuea per 100 g (35 oz) of persimmon fruit(Diospyros kaki raw)

Energy 293 kJ (70 kcal)Carbohydrates 1859 g

Sugars 1253 gDietary fiber 36 g

Fat 019 gSaturated 002 g

Protein 058 gRiboflavin (Vit B

2) 25mg (208)

Folate (Vit B9) 8 120583g (2)

Vitamin C 75mg (9)Calcium 8mg (1)Iron 015mg (1)Sodium 1mg (0)aPercentages are relative to US recommendations for adults (Source [45])

like vitamins (A B complex C E and K) and minerals(zinc copper iron magnesium calcium and phosphorus)that are valuable for the proper physiology of human health[45] Proanthocyanidins (PAs) are potent antioxidants andshow 20 and 50 times more activity than vitamins C and Erespectively [46]

52 Persimmon Peel The external layers of a fruit such aspeel shell and hull that shield the inside materials generallycontain enormous quantities of functional compounds [2]Regarding the persimmon peel it is considered as waste yetit is receiving much attention because of its chemical com-position [47 48]Themain constituent of peel is dietary fiber(4035ww) In addition high levels of antioxidants includ-ing vitamin C total phenolics and total carotenoids are alsopresent [49] Among the phenolic compounds caffeic acidp-coumaric acid ferulic acid and gallic acid (Figure 1) arepresent in large quantities [50 51] Proanthocyanidins (PAs)are condensed tannins that exhibit powerful antioxidantactivities These are largely present in the peel as comparedto pulp [52] The level of total carotenoids in persimmonpeel is very high (about 340mg100 g of dried peels as 120573-carotene equivalents) as compared to the peels of other fruitslike banana [53] and apple [54] Among the carotenoids 120573-cryptoxanthin is the highest (about 42) followed by zeax-anthin lutein and 120573-carotene (Figure 2) [55] The quantityof bioactive compounds (biologically active components)especially carotenoids and polyphenols is greater in thepeel compared to the pulp [50] Hence persimmon peelshould be consumed by individuals and used for industrialprocessing [47]

53 Persimmon Fruit Pulp Persimmon pulp is rich in nutri-ents such as vitamin C (70mg100 g) vitamin A (65mg100 g) calcium (9mg100 g) and iron (02mg100 g) [56] Inthe edible part (pulp) of the persimmon the major phenolicacids are ferulic acid p-coumaric acid and gallic acid and theantioxidant activity of these phenolic acids is affected by theirchemical structures (number of hydroxyl groups attached)

OOH

Gallic acid

OO

OH

Ferulic acid

OOH

p-Coumaric acid

O

O

O

Tannins

OH

OOH

Caffeic acidOH

OOH

OH

Proanthocyanidins

OH

OH

OH

OH

OHHO

HO

HO

HO

HOOH

HO

HO

HO

HO

Figure 1 Chemical structures of common phenolics in persimmon

Carotenoids are the major pigment present in persimmonThey contribute to both color and nutritional value [57ndash59] Carotenoid contents rapidly increase as green maturefruit changes to soft mature persimmon except for luteinand lycopene that decrease during fruit maturation [60]Among them 120573-cryptoxanthin content is the highest (50)followed by lycopene (10) 120573-carotene (10) zeaxanthin(5) and lutein (5) [59]They are all excellent lipid-solubleantioxidants especially lutein astaxanthin and zeaxanthinhaving the ability to scavenge free radicals in a lipid-solubleenvironment and thus preventing the oxidation of lipidsThefinal composition and concentration of carotenoid contentsare properly regulated to some extent by the different devel-opmental stages of plant tissues [61] Carotenoids identifiedin persimmon fruits are cis-mutatoxanthin antheraxanthinzeaxanthin neolutein cryptoxanthins 120572-carotene and 120573-carotene and also fatty acid esters of 120573-cryptoxanthin andzeaxanthin [62]

54 Persimmon Seeds Palmitic acid oleic acid and linoleicacid are the major fatty acids found in persimmon seedsranging from 704 to 783 of total fatty acids [63] Amongthe fatty acids oleic acid plays a role in cancer preventionThe effect of oleic acid on the same lines of breast cancer cellswas examined and it supported the theory that oleic acid ischemopreventative [64] Moreover omega-6 fatty acid (lino-leic acid) diminishes the risk of cardiovascular diseases [65]

55 Persimmon Leaves Persimmon leaves contain 4 flavo-nols [66] The leaves of persimmon have been reported to

4 Journal of Chemistry

Lycopene

H

HLutein

Zeaxanthin

120573-Cryptoxanthin

HO

OH

CH3

H3C

H3CCH3 CH3

CH3

HO

HO

CH3CH3

CH3

H3C

OH

120572-Carotene

120573-Carotene

Figure 2 Chemical structures of common carotenoids in persimmon

contain the following compounds 40-dihydroxy-a-truxillicacid tatarine C myricetin annulatin trifolin astragalinhyperin isoquercetin rutin quercetin kampferol kakispy-rone and kaki saponin [67] Leaves have been used for teain Korea since they were was thought to be effective againsthypertension [68]

6 Persimmon Bioactive Compounds

Persimmon fruit is a good source of polyphenols [69] Theterm ldquopolyphenolsrdquo includes a large group of substances andthey all have more than one phenolic hydroxyl group bound

to one or more benzene ring systems [70] The phenoliccompounds are secondary metabolites of plants [71 72] andfound in free and bound forms in persimmon fruit [73]

Persimmon phenols can be grouped as a function oftheir molecular complexityweightThus free phenolic acidscatechins and hydrolyzable tannins are included in low-molecular weight phenols while high-molecular weight phe-nols which are also called as condensed tannins or proan-thocyanidins (PAs) are large polymers of catechins with orwithout galloylation [74] One of the major componentsof condensed tannin in persimmon fruit was identified byAkagi et al [75] during compositional study of persimmon

Journal of Chemistry 5

with phloroglucinol They characterized this component asnovel epigallocatechin-3-O-gallate-phloroglucinol (EGCG-P) adduct Li et al [76] also reported that the persimmon pulpis comprised of flavan-3-O-galloylated extenders flavan-3-ol and flavonol terminal units and A-type interflavanlinkages which are condensed tannins with high-molecularweight

Structurally phenols contain an aromatic ring havinghydroxyl substituents ranging from simple to highly poly-merized compounds [77] The naturally present compoundsform linkages with saccharides and might be functionalderivatives like esters and methyl esters Hence the extensivevariety of phenolic compounds occurring in nature is theresult of this structural assortment These compounds arecategorized in several groups Out of them phenolic acidsflavonoids and tannins are considered as the main dietarycomponents [78]

Phenolic acids are non-flavonoid polyphenolic com-pounds comprised of 2 subgroups hydroxybenzoic andhydroxycinnamic acids Hydroxybenzoic acids contain gal-lic p-hydroxybenzoic protocatechuic vanillic and syringicacids in which they all have the C6ndashC1 structure Hydrox-ycinnamic acids instead are aromatic compounds like caf-feic ferulic p-coumaric and sinapic acids with a 3-carbon(C6ndashC3) side chain [78] The structure of phenolic com-pounds is a vital factor affecting radical-scavenging andmetalchelating activities and hence it is referred to as having astructurendashactivity relationship In the case of phenolic acidsthe antioxidant activity is influenced by the numbers andpositions of the hydroxyl groups with respect to the carboxylfunctional group [47] Hence they give their hydrogen atomsto scavenge free radicals as shown in Figure 1

Flavonoids have the C6ndashC3ndashC6 general structural back-bone in which the two C6 units (Ring A and Ring B) areof phenolic nature Flavonoids can be further divided intodifferent subgroups on basis of variations in chromane ringand hydroxylation pattern Flavonoids can be further dividedinto different subgroups such as anthocyanins flavan-3-olsflavones flavanones and flavonols While the vast majorityof the flavonoids have their Ring B attached to the C2position of Ring C these basic structures of flavonoids areaglycones however in plants most of these compoundsexist as glycosides Biological activities of these compoundsincluding antioxidant activity depend on both the structuralvariation and the glycosylation patterns [79]

Tannins the third important group of phenolics aresegmented as hydrolysable and condensed tannins which areesters of gallic acid and polymers of polyhydroxyflavan-3-ol monomers respectivelyThe third segment phlorotanninscomprised of phloroglucinol is found in brown algae How-ever these are insignificant regarding human diet [75 76]Tannins are present in persimmonprolonged life and reducedthe incidence of stroke in hypertensive rats [80 81]This effectwas attributed to the fact that persimmon tannins are 20 timesmore potent than antioxidant vitamin E [82]The persimmontannin is composed mostly of epicatechin epicatechin-3-O-gallate epigallocatechin and epigallocatechin-3-O-gallate[83]

7 Therapeutic Effects of Persimmon

Persimmon has been used for various medicinal purposes(Table 2) owing to the therapeutic properties such as diureticeffect blood pressure-lowering capability and the coughtreatment viral and bacterial infectious diseases [84] anddental caries [85] Various bioactive compounds includingpolyphenols carotenoids vitamins and dietary fiber in thefruit are responsible for beneficial properties [49] Subagioet al [52] reported the protective effect of proanthocyanidinfrompersimmon peel against DNAdamage and SIRT expres-sion in the aging process

The persimmon leaves are a good source of antioxidants[102] while the seed extracts have a strong radical-scavengingactivity [104] The fruits are a rich source of dietary carote-noids (a-carotene a-cryptoxanthin zeaxanthin lutein andlycopene) which have been implicated in the reduction ofdegenerative human diseases [91] The concentration of a-carotene and a-cryptoxanthin is so high that 100 g of pulpprovides 10 of the recommend daily allowance provitaminA [105]

Persimmon fruit can be used in the manufacturing ofproducts with functional characteristics because of its bioac-tive properties It is an excellent source of ascorbic acid tan-nins and carotenoids having healthy aspects owing to theirantioxidant and other health protecting activities [6]

71 Diabetes Diabetes mellitus is a chronic disease and thereason behind that is inherited andor acquired insufficientinsulin production by the pancreas or by the incompetenceof the insulin produced Such a deficiency results in raisedconcentrations of glucose in the blood which sequentiallydamage many of the bodyrsquos systems particularly the bloodvessels and nerves [106] When bodyrsquos defense systems nei-ther detoxify the reactive intermediates nor repair the result-ing damage from reactive oxygen species (ROS) then such animbalance condition is known as oxidative stress responsiblefor diabetes mellitus and related complications [107]

Along with insulin many other agents like sulfonylureaand biguanide can be used to reduce blood glucose levelin order to treat diabetes These hypoglycemic agents haveconsiderable side effects [108] In chronic diabetes thesehypoglycemic agents sometimes become ineffective [109]Therefore the demand of such hypoglycemic agents whichhave side effects and are either made artificially or fromnatural source is decreasing day by day [110] Hence there isneed of natural agents like plant and plant based materialswhich can show more potential for control and treatment ofdiabetes and its complications with no side effects [111] Sinceseveral years herbal remedies including different medicinalplants or their extracts have been taken orally in order totreat diabetes The search for effective natural hypoglycemicagent is under consideration as recommended by WHO[112] Recently great attention has been paid to a numberof nonvitamin antioxidants widely distributed in naturalsources like fruit vegetables and spices having the abilityto enhance the antioxidative defense mechanism at cellularlevel without side effects [113]Themain group of compoundsthat act primarily as free radical terminator or antioxidants isplant phenolics

6 Journal of Chemistry

Table 2 Various bioactive compounds present in persimmon and their functional properties

Source Health benefits ReferenceExtracted polyphenol119901-Coumaric Prevention of oxidative stress related diseases including diabetes [86]Tannins Scavenging action against active oxygen free radicals [82 87 88]

Tannin Assists the neuronal degeneration and karyopyknosis in cells reduction ofthickness of skin epidermis [89]

Flavonoids Scavenging action against active oxygen free radicals [82 87 88]Persimmon fruit

Whole fruit

Possesses antitumor effects due to betulinic acid [47 90]Blood pressure-lowering and diuretic effects also effective for coughs treatment [91]Has antioxidative potentials due to compounds like vitamin A beta-carotenelycopene lutein zeaxanthin and cryptoxanthin [92]

Exhibits hypolipidemic and antioxidant properties [50 82]Contains nutritional antioxidant vitamins polyphenols and dietary fiber [93 94]Reduction of patches of pigmentation on skin [95]Has ability to dilate the blood vessels near the surface of the skin thereby allowingmore blood to flow through the skin where it can be cooled by the air (antifebrile) [96]

Reduction of degenerative disease in human beings [91 97ndash99]Fruit peel powder Pharmacological potential such as antioxidant and hypocholesterolemic [51 95 100]Water-solublepolysaccharides extractedfrom persimmon fruits

Have ability to alter or regulate immune functions (immunomodulatory activity) [85]

Persimmon vinegar Has antitumor and antioxidative effects and also prevents metabolic disorderinduced by chronic alcohol administration [101]

Plant and leaf extracts

Persimmon leaf tea Prevents hardening of the arteries which ultimately lowers the blood pressure [95]Good source of natural antioxidants [102]

Persimmon plant extracts Contain antitumor and multidrug resistance-reversing agentsStop oxidative damage of DNA [47]

Persimmon calyx extracts Anticonvulsants [103]Persimmon plantsupplemented to a diet Hypocholesterolemic and antioxidative effects [82]

Persimmon seeds Contain omega 6 fatty acids like palmitic acid oleic acid and linoleic acid [63]Radical-scavenging activity [104]

Among fruits persimmon is comprised of a large numberof biologically active polyphenols like tannins and flavonoidshaving good antioxidant potential These polyphenols pre-vent the diabetes resulting from oxidative stress [86] sincethese work as antioxidants preventing the peroxidation oflipids by the donation of a hydrogen atom from hydroxylgroup attached to their chemical structure rapidly and formperoxyl radical (ROO) that ultimately leads to the formationof alkyl (aryl) hydroperoxide (ROOH) as shown in thefollowing reaction

ROOminus + PPH 997888rarr ROOH + PPminus (1)

The phenolic antioxidant (PPH) itself changes intopolyphenol phenoxyl radical (PP) which becomes stable afterdonating a hydrogen atom by conversion into quinines andit hinders the initiation of new chain reaction by reactingwith another radical inwhich another phenoxyl radical is alsoincluded [114 115]

Gorinstein et al [49] reported that a 2-week intake ofpersimmon peel supplemented diet considerably reducesfood intake blood glucose total cholesterol and plasmatriglycerides level in diabeticsThe researchers concluded thatpersimmon peel rich in high level of antioxidant and dietaryfiber with antidiabetic properties may be characterized asa possible nutritional supplement for improving diabeticcomplications and hyperglycemia

In fresh persimmon leaves most of the polyphenols arefound to be water soluble The chief components in persim-mon leaf tea are unique proanthocyanidin oligomers andoral administration of this tea along with starch resulted in adose-dependent decline in the blood glucose level in Wistarrats [116]

72 Atherosclerosis Inflammation and high levels of oxida-tive stress are a major initiator of cardiovascular diseaseslike atherosclerosis that ultimately leads to coronary artery

Journal of Chemistry 7

disease (CAD) In such condition the oxidative stress is char-acterized by the accumulation of metabolites (from the oxi-dation of proteins and lipids) and macrophages Accordingto the hypothesis of oxidative modification the early eventwhich initiates the development of atherogenesis (develop-ment of atheromatous plaques) is the oxidative breakdownof low-density lipoproteins Reactive oxygen species in thevessel wall have been considered to be one of the mostimportant causes of vascular dysfunction [117]

Dietary components having antioxidant properties as thepolyphenols are receiving a lot of attention because of theirability to reduce cardiovascular diseases [118 119] When dietrich in fiber is largely consumed it results in preventionand treatment of diverticular and coronary heart diseases[120] Coronary atherosclerosis especially is inhibited bypreventing oxidation of low-density lipoprotein (LDL) and bynutritional antioxidants like phenolics [121] and vitamins AC and E [122]

Hence many reports have shown that if intake of veg-etables and fruits is increased in diet then chances of coro-nary heart diseases could greatly be reduced [123] Accord-ing to Hertog et al [124] if 100 g of persimmon is con-sumed regularly then it will be sufficient to inhibit occlu-sion of arteries In young fruits of persimmon (Diospyroskaki) tannin is found to have the ability of bonding bile acid[83]

It has been established that addition of persimmon inthe diet hinders the increase in plasma lipid level and henceworks as antiatherosclerosis [80 124] which reduces thechances of mortality by the action of polyphenols [125]Matsumoto et al [82] also reported that the persimmon peelsupplemented diet shows hypocholesterolemic and antiox-idative effect

Total dietary fibers including soluble and insoluble totalphenolics including epicatechin gallic and p-coumaric acidsand concentrations of minerals like Na K Mg Ca Feand Mn are high in peel pulp and whole persimmon fruitcompared to apple [50] Hence persimmon must be givenpreference over apples and some other fruits in selecting anantiatherosclerotic diet Liu [126] reported decline in bloodtriglyceride and total cholesterol contents after intake ofpersimmon vinegar (PV) for 6 weeks

73 Cancer In recent years persimmon has been thefocus of attention for potential medicinal applications forprevention of cancer [47] Carotenoids are naturersquos mostwidespread pigments and have also received substantialattention because of both their provitamin and antioxidantroles [127] Carotenoids possess antioxidant properties thathave been associatedwith cellular protection [128] regulationof cell growth differentiation and apoptosis [129]

Not only are the carotenoid contents responsible forthe superficial appearance (color) and nutritional quality offruit [130] but also they provide potential health benefitsand disease prevention by quenching singlet oxygen andscavenging free radicals [131] Chemoprotective effects ofpersimmon against various forms of cancer are due to thecarotenoid contents [132 133] Persimmon was shown tobe effective in the treatment of prostate and breast cancers

[134] oral carcinoma cells [47] human lymphoid leukemiacells [135] and precancerous colon polyps in women [136]The bioactive compounds in persimmon may also affectmultidrug resistant (MDR) inhibiting activity It enhances theaccumulation of cancer cells due to the reduced activity ofefflux pumps MDR inhibitors from persimmon may helpto treat noncurable cancer because of the modulating effects[47] The calyx (persimmon) extracts act as anticonvulsantsand may alleviate the side effects of barbituric acid com-pounds [103]

8 Other Health Promoting Properties

Dried persimmon snacks were found to be effective inreducing the concentration of alcohol in the blood [55]Similarly Matsuno [137] observed that kaki-tannin foundin persimmon fruit flesh and leaves was soluble in artifi-cial stomach liquid and reduced blood alcohol (40) andacetaldehyde contents (30) Dietary intake of persimmontannin was found to prevent hypercholesterolemia in someanimal models and humans [138]

Some carotenoids present in persimmon are precur-sors of vitamin A [139] and also have immunoregulatory[140] and antiaging effects [141] Carotenoids are inverselylinked with inflammation atherosclerosis cardiovasculardiseases sarcopenia and mortality Carotenoid supplemen-tation improves the antioxidant status and reduces lipidperoxidation

Carotenoids like 120573-carotene 120572-carotene 120573-cryptoxan-thin lycopene and lutein (Figure 2) have been found to beassociated with inflammation and mortality risks [142] Inaddition lutein (carotenoids) present in persimmon peel canhelp protect eye vision [143]

9 Persimmon Leaves and Health

Persimmon leaves and extracts are being used as a greentea oriental medicines deodorants antiallergic substratesand cosmetics (especially for dermatitis) as they prevent skinproblems and have an antiwrinkle effect [68 143] and skinwhitening effect [72] The leaves are brewed into a beverageto release their antioxidant activity and antitumor effects andto inhibit angiotensin converting enzymes as well as alphaamylase [66] The leaves of persimmon possess antithrom-botic activity Arakawa et al [144] demonstrated that a 10000D anticoagulant fraction has been purified from the leavesthat inhibited thrombin-catalyzed fibrin formation with acompetitive inhibition pattern Based on their antimicrobialproperties persimmon leaf-based products have been incor-porated into athletersquos foot socks and soaps and persimmonleaves have been used as a sushi ingredient [145]

10 Unripen Persimmons and Health Issues

Bezoars are thick hard masses formed in gastrointestinaltract usually the stomach [146] Patients who have undergonestomach surgery and have delayed gastric emptying areoften more prone to the development of bezoars [147]Phytobezoars are the most common types of bezoars and

8 Journal of Chemistry

these are composed of skins seeds and vegetative matterincluding lignin cellulose hemicelluloses tannins and othernondigestible matter from fruits and vegetables ingestedDiospyrobezoars are a type of phytobezoars related to theconsumption of persimmon fruit and are common world-wide These are more difficult to treat because of their hardconsistency [146 148 149] Most bezoars in animals arecaused by hairs

When unripe astringent persimmon having a high levelof tannin is ingested a coagulum is formed in the stomachdue to the contact of tannin and shibuol with hydrochloricacid that accumulates cellulose hemicellulose and pro-tein [150] Phytobezoars may require surgical removal orendoscopic treatment as they are usually resistant to drugtreatment [151] Han et al [152] suggested a nonsurgicalapproach for cases of persimmon phytobezoar small intesti-nal obstruction with its partial dissolution of a bezoar byperforming oral and injected Coca-Cola therapy

11 Conclusion

Bioactive compounds particularly phenolics (ferulic p-coumaric and gallic acids) and carotenoids (120573-cryptoxan-thin lycopene 120573-carotene and lutein) are of major interestsin persimmon fruitThese valued bioactive components havestrong antioxidant potential which relates to the variety stageof maturity and fruit parts These functional compoundscan play a significant role in preventing and curing variousailments like diabetes hypercholesterolemia and cancerHence the known impact of natural bioactive compounds toimprove human health has introduced a substantial area ofresearch resulting in extensive advances in biochemical andnutritional sciences

Conflict of Interests

The authors declare that there is no conflict of interestsregarding the publication of this paper

References

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[2] S Yaqub U Farooq T Kausar Z Hayat M Jaskani and S MUllah ldquoHypocholestrolemic effect of persimmon peel powderin rabbitsrdquo Journal of Science International vol 25 no 3 pp605ndash609 2013

[3] M S Butt M T Sultan M Aziz et al ldquoPersimmon (Piospyroskaki) fruit hidden phytochemicals and health claimsrdquo EXCLIJournal vol 14 pp 542ndash561 2015

[4] A H A Hadi M E Duru and A B Martin-Diana ldquoBioactivenatural productsrdquo Journal of Chemistry vol 2013 Article ID208507 1 page 2013

[5] M R Segura Campos J Ruiz Ruiz L Chel-Guerrero and DBetancur Ancona ldquoCoccoloba uvifera (L)(Polygonaceae) fruitphytochemical screening and potential antioxidant activityrdquoJournal of Chemistry vol 2015 Article ID 534954 9 pages 2015

[6] S Karaman O S Toker F Yuksel M Cam A Kayacier andM Dogan ldquoPhysicochemical bioactive and sensory propertiesof persimmon-based ice cream technique for order prefer-ence by similarity to ideal solution to determine optimum con-centrationrdquo Journal of Dairy Science vol 97 no 1 pp 97ndash1102014

[7] M C Caruso F Galgano M Pecora R Tolve M Verrastroand F Favati ldquoImprovement of analytical methods for thedetermination of polyphenolic bioactive compounds in berryfruitsrdquo Journal of Chemistry vol 2015 Article ID 384051 6pages 2015

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[9] L Dauchet P Amouyel S Hercberg and J Dallongeville ldquoFruitand vegetable consumption and risk of coronary heart diseasea meta-analysis of cohort studiesrdquo Journal of Nutrition vol 136no 10 pp 2588ndash2593 2006

[10] A Denny and J Buttriss ldquoPlant foods and health focuson plant bioactivesrdquo EU 6th Framework Food Quality andSafety Thematic Priority Contract FOOD-CT-2005-513944European Food Information Resource (EuroFIR) Consortium2007

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[12] D Zhao C Zhou Y Sheng G Liang and J Tao ldquoMolecularcloning and expression of phytoene synthase lycopene beta-cyclase and beta-carotene hydroxylase genes in persimmon(Diospyros kaki L) fruitsrdquo PlantMolecular Biology Reporter vol29 no 2 pp 345ndash351 2011

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[20] Z Luo ldquoEffect of 1-methylcyclopropene on ripening of posthar-vest persimmon (Diospyros kaki L) fruitrdquo LWTmdashFood Scienceand Technology vol 40 no 2 pp 285ndash291 2007

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[21] A T Oz ldquoCombined effects of 1-methyl cyclopropene (1-MCP)andmodified atmosphere packaging (MAP) on different ripen-ing stages of persimmon fruit during storagerdquo African Journalof Biotechnology vol 10 no 5 pp 807ndash814 2011

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[33] X N Chen J F Fan X Yue X R Wu and L T Li ldquoRadicalscavenging activity and phenolic compounds in persimmon(Diospyros kaki L cv Mopan)rdquo Journal of Food Science vol 73no 1 pp C24ndashC28 2008

[34] H R Wang P Leng and C S Wang ldquoEffect of absorbentson storage quality of the Mopan persimmonrdquo Journal ShanxiAgriculture and Science vol 33 no 1 pp 59ndash61 2005

[35] X H Guo S Z Fang J Wang X X Guo L Q Xu and L YuanldquoStudy on the infection of the Mopan persimmon quality bycarbon dioxiderdquo Food Research Developments vol 27 pp 156ndash159 2006

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[38] N Bibi A B Khattak and ZMehmood ldquoQuality improvementand shelf life extension of persimmon fruit (Diospyros kaki)rdquoJournal of Food Engineering vol 79 no 4 pp 1359ndash1363 2007

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[48] S-O Lee S-K Chung and I-S Lee ldquoThe antidiabetic effect ofdietary persimmon (Diospyros kaki L cv sangjudungsi) peel instreptozotocin-induced daibetic ratsrdquo Journal of Food Sciencevol 71 no 3 pp S293ndashS298 2006

[49] S Gorinstein Z Zachwieja M Folta et al ldquoComparative con-tents of dietary fiber total phenolics and minerals in persim-mons and applesrdquo Journal of Agricultural and Food Chemistryvol 49 no 2 pp 952ndash957 2001

[50] H Leontowicz S Gorinstein A Lojek et al ldquoComparativecontent of some bioactive compounds in apples peaches andpears and their influence on lipids and antioxidant capacity inratsrdquo Journal of Nutritional Biochemistry vol 13 no 10 pp 603ndash610 2002

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2O2-induced cellular senescencerdquo Biolog-

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10 Journal of Chemistry

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[75] T Akagi Y Suzuki A Ikegami et al ldquoCondensed tannin com-position analysis in persimmon (Diospyros kakiThunb) fruit byacid catalysis in the presence of excess phloroglucinolrdquo Journalof the Japanese Society for Horticultural Science vol 79 no 3 pp275ndash281 2010

[76] C Li R Leverence J D Trombley et al ldquoHighmolecularweightpersimmon (Diospyros kaki L) proanthocyanidin a highlygalloylated a-linked tannin with an unusual flavonol terminalunitmyricetinrdquo Journal of Agricultural and FoodChemistry vol58 no 16 pp 9033ndash9042 2010

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[79] S Uchida H Ohta R Edamatsu M Hiromatsu A Mori andG I Nomaka ldquoPersimmon tannin prolongs life span of stroke-prone spontaneously hypertensive rats (SHRSP) by acting as afree-radical scavengerrdquo in New Horizons in Preventing Cardio-vascular Diseases Y Yamori and T Strasser Eds pp 15ndash17Academic Press Amsterdam The Netherlands Elsevier NewYork NY USA 1989

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Journal of Chemistry 11

kaki) on a broad range of virusesrdquo PLoS ONE vol 8 no 1Article ID e55343 10 pages 2013

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[89] Y Achiwa H Hibasami H Katsuzaki K Imai and T KomiyaldquoInhibitory effects of persimmon (Diospyros kaki) extract andrelated polyphenol compounds on growth of human lymphoidleukemia cellsrdquo Bioscience Biotechnology and Biochemistry vol61 no 7 pp 1099ndash1101 1997

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[100] Y Zhang X Lu Y Zhang L Qin and J Zhang ldquoSulfatedmodification and immunomodulatory activity of water-solublepolysaccharides derived from fresh Chinese persimmon fruitrdquoInternational Journal of Biological Macromolecules vol 46 no1 pp 67ndash71 2010

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[103] H Itamurah N Murakami and H Nagamatsu ldquoProperty ofkaki-tannin as a functional composition in persimmon fruitflesh and leaves and its solubility in artificial stomach liquidrdquoin Proceedings of the 27th International Horticultural Congressamp Exhibition (IHC rsquo06) vol 8 pp 265ndash267 August 2006

[104] K A Steinmetz and J D Potter ldquoVegetables fruit and cancerprevention a reviewrdquo Journal of the American Dietetic Associa-tion vol 96 no 10 pp 1027ndash1039 1996

[105] A N Nagappa P A Thakurdesai N V Rao and J SinghldquoAntidiabetic activity ofTerminalia catappa Linn fruitsrdquo Journalof Ethnopharmacology vol 88 no 1 pp 45ndash50 2003

[106] K Datta S Sinha and P Chattopadhyay ldquoReactive oxygenspecies in health and diseaserdquoNationalMedical Journal of Indiavol 13 no 6 pp 304ndash310 2000

[107] R R Holman and R C Turner ldquoOral agents and insulin in thetreatment of NIDDMrdquo in Textbook of Diabetes J Williams Edpp 407ndash469 Blackwell Press Oxford UK 1991

[108] F Giacco and M Brownlee ldquoOxidative stress and diabeticcomplicationsrdquo Circulation Research vol 107 no 9 pp 1058ndash1070 2010

[109] B K Rao M M Kesavulu R Giri and C A Rao ldquoAntidiabeticand hypolipidemic effects ofMomordicacymbalariaHook fruitpowder in alloxan-diabetic ratsrdquo Journal of Ethnopharmacologyvol 67 no 1 pp 103ndash109 1999

[110] J K Grover V Vats V Rathi and S S Dawar ldquoTraditionalIndian anti-diabetic plants attenuate progression of renal dam-age in streptozotocin induced diabetic micerdquo Journal of Ethno-pharmacology vol 76 no 3 pp 233ndash238 2001

[111] R K Gupta A N Kesari P S Murthy R Chandra V Tandonand GWatal ldquoHypoglycemic and antidiabetic effect of ethano-lic extract of leaves of Annona squamosa L in experimentalanimalsrdquo Journal of Ethnopharmacology vol 99 no 1 pp 75ndash81 2005

[112] S Gupta N Ahmad A-L Nieminen andHMukhtar ldquoGrowthinhibition cell-cycle dysregulation and induction of apopto-sis by green tea constituent (-)-epigallocatechin-3-gallate inandrogen-sensitive and androgen-insensitive human prostatecarcinoma cellsrdquoToxicology andApplied Pharmacology vol 164no 1 pp 82ndash90 2000

[113] T Yokozawa Y A Kim H Y Kim Y A Lee and G-I NonakaldquoProtective effect of persimmon peel polyphenol against highglucose-induced oxidative stress in LLC-PK1 cellsrdquo Food andChemical Toxicology vol 45 no 10 pp 1979ndash1987 2007

12 Journal of Chemistry

[114] M S Brewer ldquoNatural antioxidants sources compoundsmechanisms of action and potential applicationsrdquo Comprehen-sive Reviews in Food Science and Food Safety vol 10 no 4 pp221ndash247 2011

[115] K Kawakami H Nishida N Tatewaki Y Nakajima T Konishiand M Hirayama ldquoPersimmon leaf extract inhibits the ATMactivity during DNA damage response induced by Doxorubicinin A549 lung adenocarcinoma cellsrdquo Bioscience Biotechnologyand Biochemistry vol 75 no 4 pp 650ndash655 2011

[116] D Steinberg S Parthasarathy T E Carew J C Khoo and JL Witztum ldquoBeyond cholesterol modifications of low-densitylipoprotein that increase its atherogenicityrdquo The New EnglandJournal of Medicine vol 320 no 14 pp 915ndash924 1989

[117] P M Kris-Etherton and C L Keen ldquoEvidence that the anti-oxidant flavonoids in tea and cocoa are beneficial for cardiovas-cular healthrdquo Current Opinion in Lipidology vol 13 no 1 pp41ndash49 2002

[118] C Manach A Mazur and A Scalbert ldquoPolyphenols and pre-vention of cardiovascular diseasesrdquo Current Opinion in Lipidol-ogy vol 16 no 1 pp 77ndash84 2005

[119] J W Anderson B M Smith and N J Gustafson ldquoHealthbenefits and practical aspects of high-fiber dietsrdquo AmericanJournal of Clinical Nutrition vol 59 no 5 pp 1242ndash1247 1994

[120] D Kromhout A Menotti H Kesteloot and S Sans ldquoPreven-tion of coronary heart disease by diet and lifestyle evidencefrom prospective cross-cultural cohort and intervention stud-iesrdquo Circulation vol 105 no 7 pp 893ndash898 2002

[121] E B Rimm M J Stampfer A Ascherio E Giovannucci G AColditz andWCWillett ldquoVitamin E consumption and the riskof coronary heart disease in menrdquo The New England Journal ofMedicine vol 328 no 20 pp 1450ndash1456 1993

[122] L Dauchet J Ferrieres D Arveiler et al ldquoFrequency of fruitand vegetable consumption and coronary heart disease inFrance and Northern Ireland the prime studyrdquo British Journalof Nutrition vol 92 no 6 pp 963ndash972 2004

[123] S Gorinstein GW Kulasek E Bartnikowska et al ldquoThe effectsof diets supplementedwith either whole persimmon or phenol-free persimmon on rats fed cholesterolrdquo Food Chemistry vol70 no 3 pp 303ndash308 2000

[124] M G L Hertog E J M Feskens P C H HollmanM B Katanand D Kromhout ldquoDietary antioxidant flavonoids and risk ofcoronary heart disease the Zutphen Elderly studyrdquoThe Lancetvol 342 no 8878 pp 1007ndash1011 1993

[125] H Seo B D Jeon andR Sungpil ldquoPersimmon vinegar ripeningwith the mountain-cultivated ginseng ingestion reduces bloodlipids and lowers inflammatory cytokines in obese adolescentsrdquoJournal of Exercise Nutrition and Biochemistry vol 19 no 1 pp1ndash10 2015

[126] R H Liu ldquoPotential synergy of phytochemicals in cancerprevention mechanism of actionrdquo Journal of Nutrition vol 134no 12 supplement pp 3479Sndash3485S 2004

[127] S T Mayne ldquoAntioxidant nutrients and chronic disease use ofbiomarkers of exposure and oxidative stress status in epidemi-ologic researchrdquo Journal of Nutrition vol 133 no 3 pp 933sndash940s 2003

[128] H Tapiero D M Townsend and K D Tew ldquoThe role of caro-tenoids in the prevention of human pathologiesrdquo Biomedicineand Pharmacotherapy vol 58 no 2 pp 100ndash110 2004

[129] J Tao and S L Zhang ldquoMetabolismof carotenoid and its regula-tion in garden croprdquo Journal of Zhejiang University (Agricultureamp Life Sciences) vol 29 pp 585ndash590 2003

[130] W Miki ldquoBiological functions and activities of animal caro-tenoidsrdquo Pure and Applied Chemistry vol 63 no 1 pp 141ndash1461991

[131] H Fujiki ldquoGreen tea health benefits as cancer preventive forhumansrdquo Chemical Record vol 5 no 3 pp 119ndash132 2005

[132] A P George and S Redpath ldquoHealth and medicinal benefits ofpersimmon fruit a reviewrdquo Advances in Horticultural Sciencevol 22 no 4 pp 244ndash249 2008

[133] T Hussain S Gupta V M Adhami and H Mukhtar ldquoGreentea constituent epigallocatechin-3-gallate selectively inhibitsCOX-2 without affecting COX-1 expression in human prostatecarcinoma cellsrdquo International Journal of Cancer vol 113 no 4pp 660ndash669 2005

[134] Y-C Wang and U Bachrach ldquoThe specific anti-cancer activityof green tea (minus)-epigallocatechin-3-gallate (EGCG)rdquo AminoAcids vol 22 no 2 pp 131ndash143 2002

[135] O Takayuki ldquoPersimmons your healthy autumn treatsrdquoAsahikawa Information vol 108 pp 1ndash2 2005

[136] T Fukuda and H Shibata ldquoPersimmon calyx extracts as anti-convulsants and to alleviate the side effects of barbituric acidcompoundsrdquo Patent Japanease Kokai Tokkyo Koho vol 6 pp649ndash653 1994

[137] T Matsuno ldquoXanthophylls as precursors of retinoidsrdquo Pure andApplied Chemistry vol 63 no 1 pp 81ndash88 1991

[138] N Gato A Kadowaki N Hashimoto S-I Yokoyama and KMatsumoto ldquoPersimmon fruit tannin-rich fiber reduces choles-terol levels in humansrdquoAnnals of Nutrition andMetabolism vol62 no 1 pp 1ndash6 2013

[139] A Nagao ldquoAbsorption and function of dietary carotenoidsrdquoForum of Nutrition vol 61 pp 55ndash63 2009

[140] PD Fraser andPM Bramley ldquoThebiosynthesis andnutritionaluses of carotenoidsrdquo Progress in Lipid Research vol 43 no 3 pp228ndash265 2004

[141] D Fusco G Colloca M R Lo Monaco and M Cesari ldquoEffectsof antioxidant supplementation on the aging processrdquo ClinicalInterventions in Aging vol 2 no 3 pp 377ndash387 2007

[142] JM Seddon U Ajan and R D Sperduto ldquoDietary carotenoidsvitamins A C and E and advance age-related macular degen-eration Eye Disease Case Study Grouprdquo Journal of AmericanMedical Association vol 272 no 18 pp 1413ndash1420 1992

[143] B-J An J-H Kwak J-M Park et al ldquoInhibition of enzymeactivities and the antiwrinkle effect of polyphenol isolated fromthe persimmon leaf (Diospyros kaki folium) on human skinrdquoDermatologic Surgery vol 31 no 7 pp 848ndash854 2005

[144] H Arakawa M Takasaki N Tajima H Fukamachi and TIgarashi ldquoAntibacterial activities of persimmon extracts relatewith their hydrogen peroxide concentrationrdquo Biological andPharmaceutical Bulletin vol 37 no 7 pp 1119ndash1123 2014

[145] S D Ladas D Kamberoglou G Karamanolis J Vlachogian-nakos and I Zouboulis-Vafiadis ldquoSystematic review Coca-Cola can effectively dissolve gastric phytobezoars as a first-linetreatmentrdquo Alimentary Pharmacology and Therapeutics vol 37no 2 pp 169ndash173 2013

[146] T J Cifuentes C R Robles P P Parrilla et al ldquoPolyphenols andhealth what compounds are involvedrdquo Nutrition Metabolismand Cardiovascular Diseases vol 20 no 1 pp 1ndash6 2010

[147] J Gaya L Barranco A Llompart J Reyes and A ObradorldquoPersimmon bezoars a successful combined therapyrdquoGastroin-testinal Endoscopy vol 55 no 4 pp 581ndash583 2002

[148] P G Hayes and O D Rotstein ldquoGastrointestinal phytobezoarspresentation and managementrdquo Canadian Journal of Surgeryvol 29 no 6 pp 419ndash420 1986

Journal of Chemistry 13

[149] MM Krausz E ZMoriel A Ayalon D Pode and A L DurstldquoSurgical aspects of gastrointestinal persimmon phytobezoartreatmentrdquoThe American Journal of Surgery vol 152 no 5 pp526ndash530 1986

[150] P Walker-Renard ldquoUpdate on the medicinal management ofphytobezoarsrdquo The American Journal of Gastroenterology vol88 no 10 pp 1663ndash1666 1993

[151] S S Ha H S LeeM K Jung et al ldquoAcute intestinal obstructioncaused by a persimmon phytobezoar after dissolution therapywith Coca-Colardquo The Korean Journal of Internal Medicine vol22 no 4 pp 300ndash303 2007

[152] J Han S Kang R Choue et al ldquoFree radical scavenging effectofDiospyros kaki Laminaria japonica andUndaria pinnatifidardquoFitoterapia vol 73 no 7-8 pp 710ndash712 2002

Submit your manuscripts athttpwwwhindawicom

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

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CatalystsJournal of

Page 3: Review Article Chemistry and Functionality of Bioactive ...downloads.hindawi.com/journals/jchem/2016/3424025.pdf · Review Article Chemistry and Functionality of Bioactive Compounds

Journal of Chemistry 3

Table 1 Nutritional valuea per 100 g (35 oz) of persimmon fruit(Diospyros kaki raw)

Energy 293 kJ (70 kcal)Carbohydrates 1859 g

Sugars 1253 gDietary fiber 36 g

Fat 019 gSaturated 002 g

Protein 058 gRiboflavin (Vit B

2) 25mg (208)

Folate (Vit B9) 8 120583g (2)

Vitamin C 75mg (9)Calcium 8mg (1)Iron 015mg (1)Sodium 1mg (0)aPercentages are relative to US recommendations for adults (Source [45])

like vitamins (A B complex C E and K) and minerals(zinc copper iron magnesium calcium and phosphorus)that are valuable for the proper physiology of human health[45] Proanthocyanidins (PAs) are potent antioxidants andshow 20 and 50 times more activity than vitamins C and Erespectively [46]

52 Persimmon Peel The external layers of a fruit such aspeel shell and hull that shield the inside materials generallycontain enormous quantities of functional compounds [2]Regarding the persimmon peel it is considered as waste yetit is receiving much attention because of its chemical com-position [47 48]Themain constituent of peel is dietary fiber(4035ww) In addition high levels of antioxidants includ-ing vitamin C total phenolics and total carotenoids are alsopresent [49] Among the phenolic compounds caffeic acidp-coumaric acid ferulic acid and gallic acid (Figure 1) arepresent in large quantities [50 51] Proanthocyanidins (PAs)are condensed tannins that exhibit powerful antioxidantactivities These are largely present in the peel as comparedto pulp [52] The level of total carotenoids in persimmonpeel is very high (about 340mg100 g of dried peels as 120573-carotene equivalents) as compared to the peels of other fruitslike banana [53] and apple [54] Among the carotenoids 120573-cryptoxanthin is the highest (about 42) followed by zeax-anthin lutein and 120573-carotene (Figure 2) [55] The quantityof bioactive compounds (biologically active components)especially carotenoids and polyphenols is greater in thepeel compared to the pulp [50] Hence persimmon peelshould be consumed by individuals and used for industrialprocessing [47]

53 Persimmon Fruit Pulp Persimmon pulp is rich in nutri-ents such as vitamin C (70mg100 g) vitamin A (65mg100 g) calcium (9mg100 g) and iron (02mg100 g) [56] Inthe edible part (pulp) of the persimmon the major phenolicacids are ferulic acid p-coumaric acid and gallic acid and theantioxidant activity of these phenolic acids is affected by theirchemical structures (number of hydroxyl groups attached)

OOH

Gallic acid

OO

OH

Ferulic acid

OOH

p-Coumaric acid

O

O

O

Tannins

OH

OOH

Caffeic acidOH

OOH

OH

Proanthocyanidins

OH

OH

OH

OH

OHHO

HO

HO

HO

HOOH

HO

HO

HO

HO

Figure 1 Chemical structures of common phenolics in persimmon

Carotenoids are the major pigment present in persimmonThey contribute to both color and nutritional value [57ndash59] Carotenoid contents rapidly increase as green maturefruit changes to soft mature persimmon except for luteinand lycopene that decrease during fruit maturation [60]Among them 120573-cryptoxanthin content is the highest (50)followed by lycopene (10) 120573-carotene (10) zeaxanthin(5) and lutein (5) [59]They are all excellent lipid-solubleantioxidants especially lutein astaxanthin and zeaxanthinhaving the ability to scavenge free radicals in a lipid-solubleenvironment and thus preventing the oxidation of lipidsThefinal composition and concentration of carotenoid contentsare properly regulated to some extent by the different devel-opmental stages of plant tissues [61] Carotenoids identifiedin persimmon fruits are cis-mutatoxanthin antheraxanthinzeaxanthin neolutein cryptoxanthins 120572-carotene and 120573-carotene and also fatty acid esters of 120573-cryptoxanthin andzeaxanthin [62]

54 Persimmon Seeds Palmitic acid oleic acid and linoleicacid are the major fatty acids found in persimmon seedsranging from 704 to 783 of total fatty acids [63] Amongthe fatty acids oleic acid plays a role in cancer preventionThe effect of oleic acid on the same lines of breast cancer cellswas examined and it supported the theory that oleic acid ischemopreventative [64] Moreover omega-6 fatty acid (lino-leic acid) diminishes the risk of cardiovascular diseases [65]

55 Persimmon Leaves Persimmon leaves contain 4 flavo-nols [66] The leaves of persimmon have been reported to

4 Journal of Chemistry

Lycopene

H

HLutein

Zeaxanthin

120573-Cryptoxanthin

HO

OH

CH3

H3C

H3CCH3 CH3

CH3

HO

HO

CH3CH3

CH3

H3C

OH

120572-Carotene

120573-Carotene

Figure 2 Chemical structures of common carotenoids in persimmon

contain the following compounds 40-dihydroxy-a-truxillicacid tatarine C myricetin annulatin trifolin astragalinhyperin isoquercetin rutin quercetin kampferol kakispy-rone and kaki saponin [67] Leaves have been used for teain Korea since they were was thought to be effective againsthypertension [68]

6 Persimmon Bioactive Compounds

Persimmon fruit is a good source of polyphenols [69] Theterm ldquopolyphenolsrdquo includes a large group of substances andthey all have more than one phenolic hydroxyl group bound

to one or more benzene ring systems [70] The phenoliccompounds are secondary metabolites of plants [71 72] andfound in free and bound forms in persimmon fruit [73]

Persimmon phenols can be grouped as a function oftheir molecular complexityweightThus free phenolic acidscatechins and hydrolyzable tannins are included in low-molecular weight phenols while high-molecular weight phe-nols which are also called as condensed tannins or proan-thocyanidins (PAs) are large polymers of catechins with orwithout galloylation [74] One of the major componentsof condensed tannin in persimmon fruit was identified byAkagi et al [75] during compositional study of persimmon

Journal of Chemistry 5

with phloroglucinol They characterized this component asnovel epigallocatechin-3-O-gallate-phloroglucinol (EGCG-P) adduct Li et al [76] also reported that the persimmon pulpis comprised of flavan-3-O-galloylated extenders flavan-3-ol and flavonol terminal units and A-type interflavanlinkages which are condensed tannins with high-molecularweight

Structurally phenols contain an aromatic ring havinghydroxyl substituents ranging from simple to highly poly-merized compounds [77] The naturally present compoundsform linkages with saccharides and might be functionalderivatives like esters and methyl esters Hence the extensivevariety of phenolic compounds occurring in nature is theresult of this structural assortment These compounds arecategorized in several groups Out of them phenolic acidsflavonoids and tannins are considered as the main dietarycomponents [78]

Phenolic acids are non-flavonoid polyphenolic com-pounds comprised of 2 subgroups hydroxybenzoic andhydroxycinnamic acids Hydroxybenzoic acids contain gal-lic p-hydroxybenzoic protocatechuic vanillic and syringicacids in which they all have the C6ndashC1 structure Hydrox-ycinnamic acids instead are aromatic compounds like caf-feic ferulic p-coumaric and sinapic acids with a 3-carbon(C6ndashC3) side chain [78] The structure of phenolic com-pounds is a vital factor affecting radical-scavenging andmetalchelating activities and hence it is referred to as having astructurendashactivity relationship In the case of phenolic acidsthe antioxidant activity is influenced by the numbers andpositions of the hydroxyl groups with respect to the carboxylfunctional group [47] Hence they give their hydrogen atomsto scavenge free radicals as shown in Figure 1

Flavonoids have the C6ndashC3ndashC6 general structural back-bone in which the two C6 units (Ring A and Ring B) areof phenolic nature Flavonoids can be further divided intodifferent subgroups on basis of variations in chromane ringand hydroxylation pattern Flavonoids can be further dividedinto different subgroups such as anthocyanins flavan-3-olsflavones flavanones and flavonols While the vast majorityof the flavonoids have their Ring B attached to the C2position of Ring C these basic structures of flavonoids areaglycones however in plants most of these compoundsexist as glycosides Biological activities of these compoundsincluding antioxidant activity depend on both the structuralvariation and the glycosylation patterns [79]

Tannins the third important group of phenolics aresegmented as hydrolysable and condensed tannins which areesters of gallic acid and polymers of polyhydroxyflavan-3-ol monomers respectivelyThe third segment phlorotanninscomprised of phloroglucinol is found in brown algae How-ever these are insignificant regarding human diet [75 76]Tannins are present in persimmonprolonged life and reducedthe incidence of stroke in hypertensive rats [80 81]This effectwas attributed to the fact that persimmon tannins are 20 timesmore potent than antioxidant vitamin E [82]The persimmontannin is composed mostly of epicatechin epicatechin-3-O-gallate epigallocatechin and epigallocatechin-3-O-gallate[83]

7 Therapeutic Effects of Persimmon

Persimmon has been used for various medicinal purposes(Table 2) owing to the therapeutic properties such as diureticeffect blood pressure-lowering capability and the coughtreatment viral and bacterial infectious diseases [84] anddental caries [85] Various bioactive compounds includingpolyphenols carotenoids vitamins and dietary fiber in thefruit are responsible for beneficial properties [49] Subagioet al [52] reported the protective effect of proanthocyanidinfrompersimmon peel against DNAdamage and SIRT expres-sion in the aging process

The persimmon leaves are a good source of antioxidants[102] while the seed extracts have a strong radical-scavengingactivity [104] The fruits are a rich source of dietary carote-noids (a-carotene a-cryptoxanthin zeaxanthin lutein andlycopene) which have been implicated in the reduction ofdegenerative human diseases [91] The concentration of a-carotene and a-cryptoxanthin is so high that 100 g of pulpprovides 10 of the recommend daily allowance provitaminA [105]

Persimmon fruit can be used in the manufacturing ofproducts with functional characteristics because of its bioac-tive properties It is an excellent source of ascorbic acid tan-nins and carotenoids having healthy aspects owing to theirantioxidant and other health protecting activities [6]

71 Diabetes Diabetes mellitus is a chronic disease and thereason behind that is inherited andor acquired insufficientinsulin production by the pancreas or by the incompetenceof the insulin produced Such a deficiency results in raisedconcentrations of glucose in the blood which sequentiallydamage many of the bodyrsquos systems particularly the bloodvessels and nerves [106] When bodyrsquos defense systems nei-ther detoxify the reactive intermediates nor repair the result-ing damage from reactive oxygen species (ROS) then such animbalance condition is known as oxidative stress responsiblefor diabetes mellitus and related complications [107]

Along with insulin many other agents like sulfonylureaand biguanide can be used to reduce blood glucose levelin order to treat diabetes These hypoglycemic agents haveconsiderable side effects [108] In chronic diabetes thesehypoglycemic agents sometimes become ineffective [109]Therefore the demand of such hypoglycemic agents whichhave side effects and are either made artificially or fromnatural source is decreasing day by day [110] Hence there isneed of natural agents like plant and plant based materialswhich can show more potential for control and treatment ofdiabetes and its complications with no side effects [111] Sinceseveral years herbal remedies including different medicinalplants or their extracts have been taken orally in order totreat diabetes The search for effective natural hypoglycemicagent is under consideration as recommended by WHO[112] Recently great attention has been paid to a numberof nonvitamin antioxidants widely distributed in naturalsources like fruit vegetables and spices having the abilityto enhance the antioxidative defense mechanism at cellularlevel without side effects [113]Themain group of compoundsthat act primarily as free radical terminator or antioxidants isplant phenolics

6 Journal of Chemistry

Table 2 Various bioactive compounds present in persimmon and their functional properties

Source Health benefits ReferenceExtracted polyphenol119901-Coumaric Prevention of oxidative stress related diseases including diabetes [86]Tannins Scavenging action against active oxygen free radicals [82 87 88]

Tannin Assists the neuronal degeneration and karyopyknosis in cells reduction ofthickness of skin epidermis [89]

Flavonoids Scavenging action against active oxygen free radicals [82 87 88]Persimmon fruit

Whole fruit

Possesses antitumor effects due to betulinic acid [47 90]Blood pressure-lowering and diuretic effects also effective for coughs treatment [91]Has antioxidative potentials due to compounds like vitamin A beta-carotenelycopene lutein zeaxanthin and cryptoxanthin [92]

Exhibits hypolipidemic and antioxidant properties [50 82]Contains nutritional antioxidant vitamins polyphenols and dietary fiber [93 94]Reduction of patches of pigmentation on skin [95]Has ability to dilate the blood vessels near the surface of the skin thereby allowingmore blood to flow through the skin where it can be cooled by the air (antifebrile) [96]

Reduction of degenerative disease in human beings [91 97ndash99]Fruit peel powder Pharmacological potential such as antioxidant and hypocholesterolemic [51 95 100]Water-solublepolysaccharides extractedfrom persimmon fruits

Have ability to alter or regulate immune functions (immunomodulatory activity) [85]

Persimmon vinegar Has antitumor and antioxidative effects and also prevents metabolic disorderinduced by chronic alcohol administration [101]

Plant and leaf extracts

Persimmon leaf tea Prevents hardening of the arteries which ultimately lowers the blood pressure [95]Good source of natural antioxidants [102]

Persimmon plant extracts Contain antitumor and multidrug resistance-reversing agentsStop oxidative damage of DNA [47]

Persimmon calyx extracts Anticonvulsants [103]Persimmon plantsupplemented to a diet Hypocholesterolemic and antioxidative effects [82]

Persimmon seeds Contain omega 6 fatty acids like palmitic acid oleic acid and linoleic acid [63]Radical-scavenging activity [104]

Among fruits persimmon is comprised of a large numberof biologically active polyphenols like tannins and flavonoidshaving good antioxidant potential These polyphenols pre-vent the diabetes resulting from oxidative stress [86] sincethese work as antioxidants preventing the peroxidation oflipids by the donation of a hydrogen atom from hydroxylgroup attached to their chemical structure rapidly and formperoxyl radical (ROO) that ultimately leads to the formationof alkyl (aryl) hydroperoxide (ROOH) as shown in thefollowing reaction

ROOminus + PPH 997888rarr ROOH + PPminus (1)

The phenolic antioxidant (PPH) itself changes intopolyphenol phenoxyl radical (PP) which becomes stable afterdonating a hydrogen atom by conversion into quinines andit hinders the initiation of new chain reaction by reactingwith another radical inwhich another phenoxyl radical is alsoincluded [114 115]

Gorinstein et al [49] reported that a 2-week intake ofpersimmon peel supplemented diet considerably reducesfood intake blood glucose total cholesterol and plasmatriglycerides level in diabeticsThe researchers concluded thatpersimmon peel rich in high level of antioxidant and dietaryfiber with antidiabetic properties may be characterized asa possible nutritional supplement for improving diabeticcomplications and hyperglycemia

In fresh persimmon leaves most of the polyphenols arefound to be water soluble The chief components in persim-mon leaf tea are unique proanthocyanidin oligomers andoral administration of this tea along with starch resulted in adose-dependent decline in the blood glucose level in Wistarrats [116]

72 Atherosclerosis Inflammation and high levels of oxida-tive stress are a major initiator of cardiovascular diseaseslike atherosclerosis that ultimately leads to coronary artery

Journal of Chemistry 7

disease (CAD) In such condition the oxidative stress is char-acterized by the accumulation of metabolites (from the oxi-dation of proteins and lipids) and macrophages Accordingto the hypothesis of oxidative modification the early eventwhich initiates the development of atherogenesis (develop-ment of atheromatous plaques) is the oxidative breakdownof low-density lipoproteins Reactive oxygen species in thevessel wall have been considered to be one of the mostimportant causes of vascular dysfunction [117]

Dietary components having antioxidant properties as thepolyphenols are receiving a lot of attention because of theirability to reduce cardiovascular diseases [118 119] When dietrich in fiber is largely consumed it results in preventionand treatment of diverticular and coronary heart diseases[120] Coronary atherosclerosis especially is inhibited bypreventing oxidation of low-density lipoprotein (LDL) and bynutritional antioxidants like phenolics [121] and vitamins AC and E [122]

Hence many reports have shown that if intake of veg-etables and fruits is increased in diet then chances of coro-nary heart diseases could greatly be reduced [123] Accord-ing to Hertog et al [124] if 100 g of persimmon is con-sumed regularly then it will be sufficient to inhibit occlu-sion of arteries In young fruits of persimmon (Diospyroskaki) tannin is found to have the ability of bonding bile acid[83]

It has been established that addition of persimmon inthe diet hinders the increase in plasma lipid level and henceworks as antiatherosclerosis [80 124] which reduces thechances of mortality by the action of polyphenols [125]Matsumoto et al [82] also reported that the persimmon peelsupplemented diet shows hypocholesterolemic and antiox-idative effect

Total dietary fibers including soluble and insoluble totalphenolics including epicatechin gallic and p-coumaric acidsand concentrations of minerals like Na K Mg Ca Feand Mn are high in peel pulp and whole persimmon fruitcompared to apple [50] Hence persimmon must be givenpreference over apples and some other fruits in selecting anantiatherosclerotic diet Liu [126] reported decline in bloodtriglyceride and total cholesterol contents after intake ofpersimmon vinegar (PV) for 6 weeks

73 Cancer In recent years persimmon has been thefocus of attention for potential medicinal applications forprevention of cancer [47] Carotenoids are naturersquos mostwidespread pigments and have also received substantialattention because of both their provitamin and antioxidantroles [127] Carotenoids possess antioxidant properties thathave been associatedwith cellular protection [128] regulationof cell growth differentiation and apoptosis [129]

Not only are the carotenoid contents responsible forthe superficial appearance (color) and nutritional quality offruit [130] but also they provide potential health benefitsand disease prevention by quenching singlet oxygen andscavenging free radicals [131] Chemoprotective effects ofpersimmon against various forms of cancer are due to thecarotenoid contents [132 133] Persimmon was shown tobe effective in the treatment of prostate and breast cancers

[134] oral carcinoma cells [47] human lymphoid leukemiacells [135] and precancerous colon polyps in women [136]The bioactive compounds in persimmon may also affectmultidrug resistant (MDR) inhibiting activity It enhances theaccumulation of cancer cells due to the reduced activity ofefflux pumps MDR inhibitors from persimmon may helpto treat noncurable cancer because of the modulating effects[47] The calyx (persimmon) extracts act as anticonvulsantsand may alleviate the side effects of barbituric acid com-pounds [103]

8 Other Health Promoting Properties

Dried persimmon snacks were found to be effective inreducing the concentration of alcohol in the blood [55]Similarly Matsuno [137] observed that kaki-tannin foundin persimmon fruit flesh and leaves was soluble in artifi-cial stomach liquid and reduced blood alcohol (40) andacetaldehyde contents (30) Dietary intake of persimmontannin was found to prevent hypercholesterolemia in someanimal models and humans [138]

Some carotenoids present in persimmon are precur-sors of vitamin A [139] and also have immunoregulatory[140] and antiaging effects [141] Carotenoids are inverselylinked with inflammation atherosclerosis cardiovasculardiseases sarcopenia and mortality Carotenoid supplemen-tation improves the antioxidant status and reduces lipidperoxidation

Carotenoids like 120573-carotene 120572-carotene 120573-cryptoxan-thin lycopene and lutein (Figure 2) have been found to beassociated with inflammation and mortality risks [142] Inaddition lutein (carotenoids) present in persimmon peel canhelp protect eye vision [143]

9 Persimmon Leaves and Health

Persimmon leaves and extracts are being used as a greentea oriental medicines deodorants antiallergic substratesand cosmetics (especially for dermatitis) as they prevent skinproblems and have an antiwrinkle effect [68 143] and skinwhitening effect [72] The leaves are brewed into a beverageto release their antioxidant activity and antitumor effects andto inhibit angiotensin converting enzymes as well as alphaamylase [66] The leaves of persimmon possess antithrom-botic activity Arakawa et al [144] demonstrated that a 10000D anticoagulant fraction has been purified from the leavesthat inhibited thrombin-catalyzed fibrin formation with acompetitive inhibition pattern Based on their antimicrobialproperties persimmon leaf-based products have been incor-porated into athletersquos foot socks and soaps and persimmonleaves have been used as a sushi ingredient [145]

10 Unripen Persimmons and Health Issues

Bezoars are thick hard masses formed in gastrointestinaltract usually the stomach [146] Patients who have undergonestomach surgery and have delayed gastric emptying areoften more prone to the development of bezoars [147]Phytobezoars are the most common types of bezoars and

8 Journal of Chemistry

these are composed of skins seeds and vegetative matterincluding lignin cellulose hemicelluloses tannins and othernondigestible matter from fruits and vegetables ingestedDiospyrobezoars are a type of phytobezoars related to theconsumption of persimmon fruit and are common world-wide These are more difficult to treat because of their hardconsistency [146 148 149] Most bezoars in animals arecaused by hairs

When unripe astringent persimmon having a high levelof tannin is ingested a coagulum is formed in the stomachdue to the contact of tannin and shibuol with hydrochloricacid that accumulates cellulose hemicellulose and pro-tein [150] Phytobezoars may require surgical removal orendoscopic treatment as they are usually resistant to drugtreatment [151] Han et al [152] suggested a nonsurgicalapproach for cases of persimmon phytobezoar small intesti-nal obstruction with its partial dissolution of a bezoar byperforming oral and injected Coca-Cola therapy

11 Conclusion

Bioactive compounds particularly phenolics (ferulic p-coumaric and gallic acids) and carotenoids (120573-cryptoxan-thin lycopene 120573-carotene and lutein) are of major interestsin persimmon fruitThese valued bioactive components havestrong antioxidant potential which relates to the variety stageof maturity and fruit parts These functional compoundscan play a significant role in preventing and curing variousailments like diabetes hypercholesterolemia and cancerHence the known impact of natural bioactive compounds toimprove human health has introduced a substantial area ofresearch resulting in extensive advances in biochemical andnutritional sciences

Conflict of Interests

The authors declare that there is no conflict of interestsregarding the publication of this paper

References

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[2] S Yaqub U Farooq T Kausar Z Hayat M Jaskani and S MUllah ldquoHypocholestrolemic effect of persimmon peel powderin rabbitsrdquo Journal of Science International vol 25 no 3 pp605ndash609 2013

[3] M S Butt M T Sultan M Aziz et al ldquoPersimmon (Piospyroskaki) fruit hidden phytochemicals and health claimsrdquo EXCLIJournal vol 14 pp 542ndash561 2015

[4] A H A Hadi M E Duru and A B Martin-Diana ldquoBioactivenatural productsrdquo Journal of Chemistry vol 2013 Article ID208507 1 page 2013

[5] M R Segura Campos J Ruiz Ruiz L Chel-Guerrero and DBetancur Ancona ldquoCoccoloba uvifera (L)(Polygonaceae) fruitphytochemical screening and potential antioxidant activityrdquoJournal of Chemistry vol 2015 Article ID 534954 9 pages 2015

[6] S Karaman O S Toker F Yuksel M Cam A Kayacier andM Dogan ldquoPhysicochemical bioactive and sensory propertiesof persimmon-based ice cream technique for order prefer-ence by similarity to ideal solution to determine optimum con-centrationrdquo Journal of Dairy Science vol 97 no 1 pp 97ndash1102014

[7] M C Caruso F Galgano M Pecora R Tolve M Verrastroand F Favati ldquoImprovement of analytical methods for thedetermination of polyphenolic bioactive compounds in berryfruitsrdquo Journal of Chemistry vol 2015 Article ID 384051 6pages 2015

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[20] Z Luo ldquoEffect of 1-methylcyclopropene on ripening of posthar-vest persimmon (Diospyros kaki L) fruitrdquo LWTmdashFood Scienceand Technology vol 40 no 2 pp 285ndash291 2007

Journal of Chemistry 9

[21] A T Oz ldquoCombined effects of 1-methyl cyclopropene (1-MCP)andmodified atmosphere packaging (MAP) on different ripen-ing stages of persimmon fruit during storagerdquo African Journalof Biotechnology vol 10 no 5 pp 807ndash814 2011

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[34] H R Wang P Leng and C S Wang ldquoEffect of absorbentson storage quality of the Mopan persimmonrdquo Journal ShanxiAgriculture and Science vol 33 no 1 pp 59ndash61 2005

[35] X H Guo S Z Fang J Wang X X Guo L Q Xu and L YuanldquoStudy on the infection of the Mopan persimmon quality bycarbon dioxiderdquo Food Research Developments vol 27 pp 156ndash159 2006

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[37] J L Vazquez-Gutierrez I Hernando and A Quiles ldquoChangesin tannin solubility and microstructure of high hydrostaticpressurendashtreated persimmon cubes during storage at 4∘CrdquoEuropean Food Research and Technology vol 237 no 1 pp 9ndash172013

[38] N Bibi A B Khattak and ZMehmood ldquoQuality improvementand shelf life extension of persimmon fruit (Diospyros kaki)rdquoJournal of Food Engineering vol 79 no 4 pp 1359ndash1363 2007

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[48] S-O Lee S-K Chung and I-S Lee ldquoThe antidiabetic effect ofdietary persimmon (Diospyros kaki L cv sangjudungsi) peel instreptozotocin-induced daibetic ratsrdquo Journal of Food Sciencevol 71 no 3 pp S293ndashS298 2006

[49] S Gorinstein Z Zachwieja M Folta et al ldquoComparative con-tents of dietary fiber total phenolics and minerals in persim-mons and applesrdquo Journal of Agricultural and Food Chemistryvol 49 no 2 pp 952ndash957 2001

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2O2-induced cellular senescencerdquo Biolog-

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10 Journal of Chemistry

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Journal of Chemistry 11

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[89] Y Achiwa H Hibasami H Katsuzaki K Imai and T KomiyaldquoInhibitory effects of persimmon (Diospyros kaki) extract andrelated polyphenol compounds on growth of human lymphoidleukemia cellsrdquo Bioscience Biotechnology and Biochemistry vol61 no 7 pp 1099ndash1101 1997

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[100] Y Zhang X Lu Y Zhang L Qin and J Zhang ldquoSulfatedmodification and immunomodulatory activity of water-solublepolysaccharides derived from fresh Chinese persimmon fruitrdquoInternational Journal of Biological Macromolecules vol 46 no1 pp 67ndash71 2010

[101] Y-J Moon and Y-S Cha ldquoEffects of persimmon-vinegar onlipid metabolism and alcohol clearance in chronic alcohol-fedratsrdquo Journal of Medicinal Food vol 11 no 1 pp 38ndash45 2008

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[104] K A Steinmetz and J D Potter ldquoVegetables fruit and cancerprevention a reviewrdquo Journal of the American Dietetic Associa-tion vol 96 no 10 pp 1027ndash1039 1996

[105] A N Nagappa P A Thakurdesai N V Rao and J SinghldquoAntidiabetic activity ofTerminalia catappa Linn fruitsrdquo Journalof Ethnopharmacology vol 88 no 1 pp 45ndash50 2003

[106] K Datta S Sinha and P Chattopadhyay ldquoReactive oxygenspecies in health and diseaserdquoNationalMedical Journal of Indiavol 13 no 6 pp 304ndash310 2000

[107] R R Holman and R C Turner ldquoOral agents and insulin in thetreatment of NIDDMrdquo in Textbook of Diabetes J Williams Edpp 407ndash469 Blackwell Press Oxford UK 1991

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[109] B K Rao M M Kesavulu R Giri and C A Rao ldquoAntidiabeticand hypolipidemic effects ofMomordicacymbalariaHook fruitpowder in alloxan-diabetic ratsrdquo Journal of Ethnopharmacologyvol 67 no 1 pp 103ndash109 1999

[110] J K Grover V Vats V Rathi and S S Dawar ldquoTraditionalIndian anti-diabetic plants attenuate progression of renal dam-age in streptozotocin induced diabetic micerdquo Journal of Ethno-pharmacology vol 76 no 3 pp 233ndash238 2001

[111] R K Gupta A N Kesari P S Murthy R Chandra V Tandonand GWatal ldquoHypoglycemic and antidiabetic effect of ethano-lic extract of leaves of Annona squamosa L in experimentalanimalsrdquo Journal of Ethnopharmacology vol 99 no 1 pp 75ndash81 2005

[112] S Gupta N Ahmad A-L Nieminen andHMukhtar ldquoGrowthinhibition cell-cycle dysregulation and induction of apopto-sis by green tea constituent (-)-epigallocatechin-3-gallate inandrogen-sensitive and androgen-insensitive human prostatecarcinoma cellsrdquoToxicology andApplied Pharmacology vol 164no 1 pp 82ndash90 2000

[113] T Yokozawa Y A Kim H Y Kim Y A Lee and G-I NonakaldquoProtective effect of persimmon peel polyphenol against highglucose-induced oxidative stress in LLC-PK1 cellsrdquo Food andChemical Toxicology vol 45 no 10 pp 1979ndash1987 2007

12 Journal of Chemistry

[114] M S Brewer ldquoNatural antioxidants sources compoundsmechanisms of action and potential applicationsrdquo Comprehen-sive Reviews in Food Science and Food Safety vol 10 no 4 pp221ndash247 2011

[115] K Kawakami H Nishida N Tatewaki Y Nakajima T Konishiand M Hirayama ldquoPersimmon leaf extract inhibits the ATMactivity during DNA damage response induced by Doxorubicinin A549 lung adenocarcinoma cellsrdquo Bioscience Biotechnologyand Biochemistry vol 75 no 4 pp 650ndash655 2011

[116] D Steinberg S Parthasarathy T E Carew J C Khoo and JL Witztum ldquoBeyond cholesterol modifications of low-densitylipoprotein that increase its atherogenicityrdquo The New EnglandJournal of Medicine vol 320 no 14 pp 915ndash924 1989

[117] P M Kris-Etherton and C L Keen ldquoEvidence that the anti-oxidant flavonoids in tea and cocoa are beneficial for cardiovas-cular healthrdquo Current Opinion in Lipidology vol 13 no 1 pp41ndash49 2002

[118] C Manach A Mazur and A Scalbert ldquoPolyphenols and pre-vention of cardiovascular diseasesrdquo Current Opinion in Lipidol-ogy vol 16 no 1 pp 77ndash84 2005

[119] J W Anderson B M Smith and N J Gustafson ldquoHealthbenefits and practical aspects of high-fiber dietsrdquo AmericanJournal of Clinical Nutrition vol 59 no 5 pp 1242ndash1247 1994

[120] D Kromhout A Menotti H Kesteloot and S Sans ldquoPreven-tion of coronary heart disease by diet and lifestyle evidencefrom prospective cross-cultural cohort and intervention stud-iesrdquo Circulation vol 105 no 7 pp 893ndash898 2002

[121] E B Rimm M J Stampfer A Ascherio E Giovannucci G AColditz andWCWillett ldquoVitamin E consumption and the riskof coronary heart disease in menrdquo The New England Journal ofMedicine vol 328 no 20 pp 1450ndash1456 1993

[122] L Dauchet J Ferrieres D Arveiler et al ldquoFrequency of fruitand vegetable consumption and coronary heart disease inFrance and Northern Ireland the prime studyrdquo British Journalof Nutrition vol 92 no 6 pp 963ndash972 2004

[123] S Gorinstein GW Kulasek E Bartnikowska et al ldquoThe effectsof diets supplementedwith either whole persimmon or phenol-free persimmon on rats fed cholesterolrdquo Food Chemistry vol70 no 3 pp 303ndash308 2000

[124] M G L Hertog E J M Feskens P C H HollmanM B Katanand D Kromhout ldquoDietary antioxidant flavonoids and risk ofcoronary heart disease the Zutphen Elderly studyrdquoThe Lancetvol 342 no 8878 pp 1007ndash1011 1993

[125] H Seo B D Jeon andR Sungpil ldquoPersimmon vinegar ripeningwith the mountain-cultivated ginseng ingestion reduces bloodlipids and lowers inflammatory cytokines in obese adolescentsrdquoJournal of Exercise Nutrition and Biochemistry vol 19 no 1 pp1ndash10 2015

[126] R H Liu ldquoPotential synergy of phytochemicals in cancerprevention mechanism of actionrdquo Journal of Nutrition vol 134no 12 supplement pp 3479Sndash3485S 2004

[127] S T Mayne ldquoAntioxidant nutrients and chronic disease use ofbiomarkers of exposure and oxidative stress status in epidemi-ologic researchrdquo Journal of Nutrition vol 133 no 3 pp 933sndash940s 2003

[128] H Tapiero D M Townsend and K D Tew ldquoThe role of caro-tenoids in the prevention of human pathologiesrdquo Biomedicineand Pharmacotherapy vol 58 no 2 pp 100ndash110 2004

[129] J Tao and S L Zhang ldquoMetabolismof carotenoid and its regula-tion in garden croprdquo Journal of Zhejiang University (Agricultureamp Life Sciences) vol 29 pp 585ndash590 2003

[130] W Miki ldquoBiological functions and activities of animal caro-tenoidsrdquo Pure and Applied Chemistry vol 63 no 1 pp 141ndash1461991

[131] H Fujiki ldquoGreen tea health benefits as cancer preventive forhumansrdquo Chemical Record vol 5 no 3 pp 119ndash132 2005

[132] A P George and S Redpath ldquoHealth and medicinal benefits ofpersimmon fruit a reviewrdquo Advances in Horticultural Sciencevol 22 no 4 pp 244ndash249 2008

[133] T Hussain S Gupta V M Adhami and H Mukhtar ldquoGreentea constituent epigallocatechin-3-gallate selectively inhibitsCOX-2 without affecting COX-1 expression in human prostatecarcinoma cellsrdquo International Journal of Cancer vol 113 no 4pp 660ndash669 2005

[134] Y-C Wang and U Bachrach ldquoThe specific anti-cancer activityof green tea (minus)-epigallocatechin-3-gallate (EGCG)rdquo AminoAcids vol 22 no 2 pp 131ndash143 2002

[135] O Takayuki ldquoPersimmons your healthy autumn treatsrdquoAsahikawa Information vol 108 pp 1ndash2 2005

[136] T Fukuda and H Shibata ldquoPersimmon calyx extracts as anti-convulsants and to alleviate the side effects of barbituric acidcompoundsrdquo Patent Japanease Kokai Tokkyo Koho vol 6 pp649ndash653 1994

[137] T Matsuno ldquoXanthophylls as precursors of retinoidsrdquo Pure andApplied Chemistry vol 63 no 1 pp 81ndash88 1991

[138] N Gato A Kadowaki N Hashimoto S-I Yokoyama and KMatsumoto ldquoPersimmon fruit tannin-rich fiber reduces choles-terol levels in humansrdquoAnnals of Nutrition andMetabolism vol62 no 1 pp 1ndash6 2013

[139] A Nagao ldquoAbsorption and function of dietary carotenoidsrdquoForum of Nutrition vol 61 pp 55ndash63 2009

[140] PD Fraser andPM Bramley ldquoThebiosynthesis andnutritionaluses of carotenoidsrdquo Progress in Lipid Research vol 43 no 3 pp228ndash265 2004

[141] D Fusco G Colloca M R Lo Monaco and M Cesari ldquoEffectsof antioxidant supplementation on the aging processrdquo ClinicalInterventions in Aging vol 2 no 3 pp 377ndash387 2007

[142] JM Seddon U Ajan and R D Sperduto ldquoDietary carotenoidsvitamins A C and E and advance age-related macular degen-eration Eye Disease Case Study Grouprdquo Journal of AmericanMedical Association vol 272 no 18 pp 1413ndash1420 1992

[143] B-J An J-H Kwak J-M Park et al ldquoInhibition of enzymeactivities and the antiwrinkle effect of polyphenol isolated fromthe persimmon leaf (Diospyros kaki folium) on human skinrdquoDermatologic Surgery vol 31 no 7 pp 848ndash854 2005

[144] H Arakawa M Takasaki N Tajima H Fukamachi and TIgarashi ldquoAntibacterial activities of persimmon extracts relatewith their hydrogen peroxide concentrationrdquo Biological andPharmaceutical Bulletin vol 37 no 7 pp 1119ndash1123 2014

[145] S D Ladas D Kamberoglou G Karamanolis J Vlachogian-nakos and I Zouboulis-Vafiadis ldquoSystematic review Coca-Cola can effectively dissolve gastric phytobezoars as a first-linetreatmentrdquo Alimentary Pharmacology and Therapeutics vol 37no 2 pp 169ndash173 2013

[146] T J Cifuentes C R Robles P P Parrilla et al ldquoPolyphenols andhealth what compounds are involvedrdquo Nutrition Metabolismand Cardiovascular Diseases vol 20 no 1 pp 1ndash6 2010

[147] J Gaya L Barranco A Llompart J Reyes and A ObradorldquoPersimmon bezoars a successful combined therapyrdquoGastroin-testinal Endoscopy vol 55 no 4 pp 581ndash583 2002

[148] P G Hayes and O D Rotstein ldquoGastrointestinal phytobezoarspresentation and managementrdquo Canadian Journal of Surgeryvol 29 no 6 pp 419ndash420 1986

Journal of Chemistry 13

[149] MM Krausz E ZMoriel A Ayalon D Pode and A L DurstldquoSurgical aspects of gastrointestinal persimmon phytobezoartreatmentrdquoThe American Journal of Surgery vol 152 no 5 pp526ndash530 1986

[150] P Walker-Renard ldquoUpdate on the medicinal management ofphytobezoarsrdquo The American Journal of Gastroenterology vol88 no 10 pp 1663ndash1666 1993

[151] S S Ha H S LeeM K Jung et al ldquoAcute intestinal obstructioncaused by a persimmon phytobezoar after dissolution therapywith Coca-Colardquo The Korean Journal of Internal Medicine vol22 no 4 pp 300ndash303 2007

[152] J Han S Kang R Choue et al ldquoFree radical scavenging effectofDiospyros kaki Laminaria japonica andUndaria pinnatifidardquoFitoterapia vol 73 no 7-8 pp 710ndash712 2002

Submit your manuscripts athttpwwwhindawicom

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Page 4: Review Article Chemistry and Functionality of Bioactive ...downloads.hindawi.com/journals/jchem/2016/3424025.pdf · Review Article Chemistry and Functionality of Bioactive Compounds

4 Journal of Chemistry

Lycopene

H

HLutein

Zeaxanthin

120573-Cryptoxanthin

HO

OH

CH3

H3C

H3CCH3 CH3

CH3

HO

HO

CH3CH3

CH3

H3C

OH

120572-Carotene

120573-Carotene

Figure 2 Chemical structures of common carotenoids in persimmon

contain the following compounds 40-dihydroxy-a-truxillicacid tatarine C myricetin annulatin trifolin astragalinhyperin isoquercetin rutin quercetin kampferol kakispy-rone and kaki saponin [67] Leaves have been used for teain Korea since they were was thought to be effective againsthypertension [68]

6 Persimmon Bioactive Compounds

Persimmon fruit is a good source of polyphenols [69] Theterm ldquopolyphenolsrdquo includes a large group of substances andthey all have more than one phenolic hydroxyl group bound

to one or more benzene ring systems [70] The phenoliccompounds are secondary metabolites of plants [71 72] andfound in free and bound forms in persimmon fruit [73]

Persimmon phenols can be grouped as a function oftheir molecular complexityweightThus free phenolic acidscatechins and hydrolyzable tannins are included in low-molecular weight phenols while high-molecular weight phe-nols which are also called as condensed tannins or proan-thocyanidins (PAs) are large polymers of catechins with orwithout galloylation [74] One of the major componentsof condensed tannin in persimmon fruit was identified byAkagi et al [75] during compositional study of persimmon

Journal of Chemistry 5

with phloroglucinol They characterized this component asnovel epigallocatechin-3-O-gallate-phloroglucinol (EGCG-P) adduct Li et al [76] also reported that the persimmon pulpis comprised of flavan-3-O-galloylated extenders flavan-3-ol and flavonol terminal units and A-type interflavanlinkages which are condensed tannins with high-molecularweight

Structurally phenols contain an aromatic ring havinghydroxyl substituents ranging from simple to highly poly-merized compounds [77] The naturally present compoundsform linkages with saccharides and might be functionalderivatives like esters and methyl esters Hence the extensivevariety of phenolic compounds occurring in nature is theresult of this structural assortment These compounds arecategorized in several groups Out of them phenolic acidsflavonoids and tannins are considered as the main dietarycomponents [78]

Phenolic acids are non-flavonoid polyphenolic com-pounds comprised of 2 subgroups hydroxybenzoic andhydroxycinnamic acids Hydroxybenzoic acids contain gal-lic p-hydroxybenzoic protocatechuic vanillic and syringicacids in which they all have the C6ndashC1 structure Hydrox-ycinnamic acids instead are aromatic compounds like caf-feic ferulic p-coumaric and sinapic acids with a 3-carbon(C6ndashC3) side chain [78] The structure of phenolic com-pounds is a vital factor affecting radical-scavenging andmetalchelating activities and hence it is referred to as having astructurendashactivity relationship In the case of phenolic acidsthe antioxidant activity is influenced by the numbers andpositions of the hydroxyl groups with respect to the carboxylfunctional group [47] Hence they give their hydrogen atomsto scavenge free radicals as shown in Figure 1

Flavonoids have the C6ndashC3ndashC6 general structural back-bone in which the two C6 units (Ring A and Ring B) areof phenolic nature Flavonoids can be further divided intodifferent subgroups on basis of variations in chromane ringand hydroxylation pattern Flavonoids can be further dividedinto different subgroups such as anthocyanins flavan-3-olsflavones flavanones and flavonols While the vast majorityof the flavonoids have their Ring B attached to the C2position of Ring C these basic structures of flavonoids areaglycones however in plants most of these compoundsexist as glycosides Biological activities of these compoundsincluding antioxidant activity depend on both the structuralvariation and the glycosylation patterns [79]

Tannins the third important group of phenolics aresegmented as hydrolysable and condensed tannins which areesters of gallic acid and polymers of polyhydroxyflavan-3-ol monomers respectivelyThe third segment phlorotanninscomprised of phloroglucinol is found in brown algae How-ever these are insignificant regarding human diet [75 76]Tannins are present in persimmonprolonged life and reducedthe incidence of stroke in hypertensive rats [80 81]This effectwas attributed to the fact that persimmon tannins are 20 timesmore potent than antioxidant vitamin E [82]The persimmontannin is composed mostly of epicatechin epicatechin-3-O-gallate epigallocatechin and epigallocatechin-3-O-gallate[83]

7 Therapeutic Effects of Persimmon

Persimmon has been used for various medicinal purposes(Table 2) owing to the therapeutic properties such as diureticeffect blood pressure-lowering capability and the coughtreatment viral and bacterial infectious diseases [84] anddental caries [85] Various bioactive compounds includingpolyphenols carotenoids vitamins and dietary fiber in thefruit are responsible for beneficial properties [49] Subagioet al [52] reported the protective effect of proanthocyanidinfrompersimmon peel against DNAdamage and SIRT expres-sion in the aging process

The persimmon leaves are a good source of antioxidants[102] while the seed extracts have a strong radical-scavengingactivity [104] The fruits are a rich source of dietary carote-noids (a-carotene a-cryptoxanthin zeaxanthin lutein andlycopene) which have been implicated in the reduction ofdegenerative human diseases [91] The concentration of a-carotene and a-cryptoxanthin is so high that 100 g of pulpprovides 10 of the recommend daily allowance provitaminA [105]

Persimmon fruit can be used in the manufacturing ofproducts with functional characteristics because of its bioac-tive properties It is an excellent source of ascorbic acid tan-nins and carotenoids having healthy aspects owing to theirantioxidant and other health protecting activities [6]

71 Diabetes Diabetes mellitus is a chronic disease and thereason behind that is inherited andor acquired insufficientinsulin production by the pancreas or by the incompetenceof the insulin produced Such a deficiency results in raisedconcentrations of glucose in the blood which sequentiallydamage many of the bodyrsquos systems particularly the bloodvessels and nerves [106] When bodyrsquos defense systems nei-ther detoxify the reactive intermediates nor repair the result-ing damage from reactive oxygen species (ROS) then such animbalance condition is known as oxidative stress responsiblefor diabetes mellitus and related complications [107]

Along with insulin many other agents like sulfonylureaand biguanide can be used to reduce blood glucose levelin order to treat diabetes These hypoglycemic agents haveconsiderable side effects [108] In chronic diabetes thesehypoglycemic agents sometimes become ineffective [109]Therefore the demand of such hypoglycemic agents whichhave side effects and are either made artificially or fromnatural source is decreasing day by day [110] Hence there isneed of natural agents like plant and plant based materialswhich can show more potential for control and treatment ofdiabetes and its complications with no side effects [111] Sinceseveral years herbal remedies including different medicinalplants or their extracts have been taken orally in order totreat diabetes The search for effective natural hypoglycemicagent is under consideration as recommended by WHO[112] Recently great attention has been paid to a numberof nonvitamin antioxidants widely distributed in naturalsources like fruit vegetables and spices having the abilityto enhance the antioxidative defense mechanism at cellularlevel without side effects [113]Themain group of compoundsthat act primarily as free radical terminator or antioxidants isplant phenolics

6 Journal of Chemistry

Table 2 Various bioactive compounds present in persimmon and their functional properties

Source Health benefits ReferenceExtracted polyphenol119901-Coumaric Prevention of oxidative stress related diseases including diabetes [86]Tannins Scavenging action against active oxygen free radicals [82 87 88]

Tannin Assists the neuronal degeneration and karyopyknosis in cells reduction ofthickness of skin epidermis [89]

Flavonoids Scavenging action against active oxygen free radicals [82 87 88]Persimmon fruit

Whole fruit

Possesses antitumor effects due to betulinic acid [47 90]Blood pressure-lowering and diuretic effects also effective for coughs treatment [91]Has antioxidative potentials due to compounds like vitamin A beta-carotenelycopene lutein zeaxanthin and cryptoxanthin [92]

Exhibits hypolipidemic and antioxidant properties [50 82]Contains nutritional antioxidant vitamins polyphenols and dietary fiber [93 94]Reduction of patches of pigmentation on skin [95]Has ability to dilate the blood vessels near the surface of the skin thereby allowingmore blood to flow through the skin where it can be cooled by the air (antifebrile) [96]

Reduction of degenerative disease in human beings [91 97ndash99]Fruit peel powder Pharmacological potential such as antioxidant and hypocholesterolemic [51 95 100]Water-solublepolysaccharides extractedfrom persimmon fruits

Have ability to alter or regulate immune functions (immunomodulatory activity) [85]

Persimmon vinegar Has antitumor and antioxidative effects and also prevents metabolic disorderinduced by chronic alcohol administration [101]

Plant and leaf extracts

Persimmon leaf tea Prevents hardening of the arteries which ultimately lowers the blood pressure [95]Good source of natural antioxidants [102]

Persimmon plant extracts Contain antitumor and multidrug resistance-reversing agentsStop oxidative damage of DNA [47]

Persimmon calyx extracts Anticonvulsants [103]Persimmon plantsupplemented to a diet Hypocholesterolemic and antioxidative effects [82]

Persimmon seeds Contain omega 6 fatty acids like palmitic acid oleic acid and linoleic acid [63]Radical-scavenging activity [104]

Among fruits persimmon is comprised of a large numberof biologically active polyphenols like tannins and flavonoidshaving good antioxidant potential These polyphenols pre-vent the diabetes resulting from oxidative stress [86] sincethese work as antioxidants preventing the peroxidation oflipids by the donation of a hydrogen atom from hydroxylgroup attached to their chemical structure rapidly and formperoxyl radical (ROO) that ultimately leads to the formationof alkyl (aryl) hydroperoxide (ROOH) as shown in thefollowing reaction

ROOminus + PPH 997888rarr ROOH + PPminus (1)

The phenolic antioxidant (PPH) itself changes intopolyphenol phenoxyl radical (PP) which becomes stable afterdonating a hydrogen atom by conversion into quinines andit hinders the initiation of new chain reaction by reactingwith another radical inwhich another phenoxyl radical is alsoincluded [114 115]

Gorinstein et al [49] reported that a 2-week intake ofpersimmon peel supplemented diet considerably reducesfood intake blood glucose total cholesterol and plasmatriglycerides level in diabeticsThe researchers concluded thatpersimmon peel rich in high level of antioxidant and dietaryfiber with antidiabetic properties may be characterized asa possible nutritional supplement for improving diabeticcomplications and hyperglycemia

In fresh persimmon leaves most of the polyphenols arefound to be water soluble The chief components in persim-mon leaf tea are unique proanthocyanidin oligomers andoral administration of this tea along with starch resulted in adose-dependent decline in the blood glucose level in Wistarrats [116]

72 Atherosclerosis Inflammation and high levels of oxida-tive stress are a major initiator of cardiovascular diseaseslike atherosclerosis that ultimately leads to coronary artery

Journal of Chemistry 7

disease (CAD) In such condition the oxidative stress is char-acterized by the accumulation of metabolites (from the oxi-dation of proteins and lipids) and macrophages Accordingto the hypothesis of oxidative modification the early eventwhich initiates the development of atherogenesis (develop-ment of atheromatous plaques) is the oxidative breakdownof low-density lipoproteins Reactive oxygen species in thevessel wall have been considered to be one of the mostimportant causes of vascular dysfunction [117]

Dietary components having antioxidant properties as thepolyphenols are receiving a lot of attention because of theirability to reduce cardiovascular diseases [118 119] When dietrich in fiber is largely consumed it results in preventionand treatment of diverticular and coronary heart diseases[120] Coronary atherosclerosis especially is inhibited bypreventing oxidation of low-density lipoprotein (LDL) and bynutritional antioxidants like phenolics [121] and vitamins AC and E [122]

Hence many reports have shown that if intake of veg-etables and fruits is increased in diet then chances of coro-nary heart diseases could greatly be reduced [123] Accord-ing to Hertog et al [124] if 100 g of persimmon is con-sumed regularly then it will be sufficient to inhibit occlu-sion of arteries In young fruits of persimmon (Diospyroskaki) tannin is found to have the ability of bonding bile acid[83]

It has been established that addition of persimmon inthe diet hinders the increase in plasma lipid level and henceworks as antiatherosclerosis [80 124] which reduces thechances of mortality by the action of polyphenols [125]Matsumoto et al [82] also reported that the persimmon peelsupplemented diet shows hypocholesterolemic and antiox-idative effect

Total dietary fibers including soluble and insoluble totalphenolics including epicatechin gallic and p-coumaric acidsand concentrations of minerals like Na K Mg Ca Feand Mn are high in peel pulp and whole persimmon fruitcompared to apple [50] Hence persimmon must be givenpreference over apples and some other fruits in selecting anantiatherosclerotic diet Liu [126] reported decline in bloodtriglyceride and total cholesterol contents after intake ofpersimmon vinegar (PV) for 6 weeks

73 Cancer In recent years persimmon has been thefocus of attention for potential medicinal applications forprevention of cancer [47] Carotenoids are naturersquos mostwidespread pigments and have also received substantialattention because of both their provitamin and antioxidantroles [127] Carotenoids possess antioxidant properties thathave been associatedwith cellular protection [128] regulationof cell growth differentiation and apoptosis [129]

Not only are the carotenoid contents responsible forthe superficial appearance (color) and nutritional quality offruit [130] but also they provide potential health benefitsand disease prevention by quenching singlet oxygen andscavenging free radicals [131] Chemoprotective effects ofpersimmon against various forms of cancer are due to thecarotenoid contents [132 133] Persimmon was shown tobe effective in the treatment of prostate and breast cancers

[134] oral carcinoma cells [47] human lymphoid leukemiacells [135] and precancerous colon polyps in women [136]The bioactive compounds in persimmon may also affectmultidrug resistant (MDR) inhibiting activity It enhances theaccumulation of cancer cells due to the reduced activity ofefflux pumps MDR inhibitors from persimmon may helpto treat noncurable cancer because of the modulating effects[47] The calyx (persimmon) extracts act as anticonvulsantsand may alleviate the side effects of barbituric acid com-pounds [103]

8 Other Health Promoting Properties

Dried persimmon snacks were found to be effective inreducing the concentration of alcohol in the blood [55]Similarly Matsuno [137] observed that kaki-tannin foundin persimmon fruit flesh and leaves was soluble in artifi-cial stomach liquid and reduced blood alcohol (40) andacetaldehyde contents (30) Dietary intake of persimmontannin was found to prevent hypercholesterolemia in someanimal models and humans [138]

Some carotenoids present in persimmon are precur-sors of vitamin A [139] and also have immunoregulatory[140] and antiaging effects [141] Carotenoids are inverselylinked with inflammation atherosclerosis cardiovasculardiseases sarcopenia and mortality Carotenoid supplemen-tation improves the antioxidant status and reduces lipidperoxidation

Carotenoids like 120573-carotene 120572-carotene 120573-cryptoxan-thin lycopene and lutein (Figure 2) have been found to beassociated with inflammation and mortality risks [142] Inaddition lutein (carotenoids) present in persimmon peel canhelp protect eye vision [143]

9 Persimmon Leaves and Health

Persimmon leaves and extracts are being used as a greentea oriental medicines deodorants antiallergic substratesand cosmetics (especially for dermatitis) as they prevent skinproblems and have an antiwrinkle effect [68 143] and skinwhitening effect [72] The leaves are brewed into a beverageto release their antioxidant activity and antitumor effects andto inhibit angiotensin converting enzymes as well as alphaamylase [66] The leaves of persimmon possess antithrom-botic activity Arakawa et al [144] demonstrated that a 10000D anticoagulant fraction has been purified from the leavesthat inhibited thrombin-catalyzed fibrin formation with acompetitive inhibition pattern Based on their antimicrobialproperties persimmon leaf-based products have been incor-porated into athletersquos foot socks and soaps and persimmonleaves have been used as a sushi ingredient [145]

10 Unripen Persimmons and Health Issues

Bezoars are thick hard masses formed in gastrointestinaltract usually the stomach [146] Patients who have undergonestomach surgery and have delayed gastric emptying areoften more prone to the development of bezoars [147]Phytobezoars are the most common types of bezoars and

8 Journal of Chemistry

these are composed of skins seeds and vegetative matterincluding lignin cellulose hemicelluloses tannins and othernondigestible matter from fruits and vegetables ingestedDiospyrobezoars are a type of phytobezoars related to theconsumption of persimmon fruit and are common world-wide These are more difficult to treat because of their hardconsistency [146 148 149] Most bezoars in animals arecaused by hairs

When unripe astringent persimmon having a high levelof tannin is ingested a coagulum is formed in the stomachdue to the contact of tannin and shibuol with hydrochloricacid that accumulates cellulose hemicellulose and pro-tein [150] Phytobezoars may require surgical removal orendoscopic treatment as they are usually resistant to drugtreatment [151] Han et al [152] suggested a nonsurgicalapproach for cases of persimmon phytobezoar small intesti-nal obstruction with its partial dissolution of a bezoar byperforming oral and injected Coca-Cola therapy

11 Conclusion

Bioactive compounds particularly phenolics (ferulic p-coumaric and gallic acids) and carotenoids (120573-cryptoxan-thin lycopene 120573-carotene and lutein) are of major interestsin persimmon fruitThese valued bioactive components havestrong antioxidant potential which relates to the variety stageof maturity and fruit parts These functional compoundscan play a significant role in preventing and curing variousailments like diabetes hypercholesterolemia and cancerHence the known impact of natural bioactive compounds toimprove human health has introduced a substantial area ofresearch resulting in extensive advances in biochemical andnutritional sciences

Conflict of Interests

The authors declare that there is no conflict of interestsregarding the publication of this paper

References

[1] S Lordan R P Ross and C Stanton ldquoMarine bioactives asfunctional food ingredients potential to reduce the incidenceof chronic diseasesrdquoMarine Drugs vol 9 no 6 pp 1056ndash11002011

[2] S Yaqub U Farooq T Kausar Z Hayat M Jaskani and S MUllah ldquoHypocholestrolemic effect of persimmon peel powderin rabbitsrdquo Journal of Science International vol 25 no 3 pp605ndash609 2013

[3] M S Butt M T Sultan M Aziz et al ldquoPersimmon (Piospyroskaki) fruit hidden phytochemicals and health claimsrdquo EXCLIJournal vol 14 pp 542ndash561 2015

[4] A H A Hadi M E Duru and A B Martin-Diana ldquoBioactivenatural productsrdquo Journal of Chemistry vol 2013 Article ID208507 1 page 2013

[5] M R Segura Campos J Ruiz Ruiz L Chel-Guerrero and DBetancur Ancona ldquoCoccoloba uvifera (L)(Polygonaceae) fruitphytochemical screening and potential antioxidant activityrdquoJournal of Chemistry vol 2015 Article ID 534954 9 pages 2015

[6] S Karaman O S Toker F Yuksel M Cam A Kayacier andM Dogan ldquoPhysicochemical bioactive and sensory propertiesof persimmon-based ice cream technique for order prefer-ence by similarity to ideal solution to determine optimum con-centrationrdquo Journal of Dairy Science vol 97 no 1 pp 97ndash1102014

[7] M C Caruso F Galgano M Pecora R Tolve M Verrastroand F Favati ldquoImprovement of analytical methods for thedetermination of polyphenolic bioactive compounds in berryfruitsrdquo Journal of Chemistry vol 2015 Article ID 384051 6pages 2015

[8] R H Liu ldquoHealth benefits of fruit and vegetables are fromadditive and synergistic combinations of phytochemicalsrdquo TheAmerican Journal of Clinical Nutrition vol 78 no 3 pp 517Sndash520S 2003

[9] L Dauchet P Amouyel S Hercberg and J Dallongeville ldquoFruitand vegetable consumption and risk of coronary heart diseasea meta-analysis of cohort studiesrdquo Journal of Nutrition vol 136no 10 pp 2588ndash2593 2006

[10] A Denny and J Buttriss ldquoPlant foods and health focuson plant bioactivesrdquo EU 6th Framework Food Quality andSafety Thematic Priority Contract FOOD-CT-2005-513944European Food Information Resource (EuroFIR) Consortium2007

[11] S M K Rates ldquoPlants as source of drugsrdquo Toxicon vol 39 no5 pp 603ndash613 2001

[12] D Zhao C Zhou Y Sheng G Liang and J Tao ldquoMolecularcloning and expression of phytoene synthase lycopene beta-cyclase and beta-carotene hydroxylase genes in persimmon(Diospyros kaki L) fruitsrdquo PlantMolecular Biology Reporter vol29 no 2 pp 345ndash351 2011

[13] K Suzuki S Tsubaki M Fujita N Koyama M Takahashiand K Takazawa ldquoEffects of safflower seed extract on arterialstiffnessrdquo Vascular Health and Risk Management vol 6 no 1pp 1007ndash1014 2010

[14] M S Butt and M T Sultan ldquoGreen tea naturersquos defense againstmalignanciesrdquo Critical Reviews in Food Science and Nutritionvol 49 no 5 pp 463ndash473 2009

[15] I Raskin D M Ribnicky S Komarnytsky et al ldquoPlants andhuman health in the twenty-first centuryrdquo Trends in Biotechnol-ogy vol 20 no 12 pp 522ndash531 2002

[16] S Parab R Kulkarni and U Thatte ldquoHeavy metals in herbalmedicinesrdquo Indian Journal of Gastroenterology vol 22 no 3 pp111ndash112 2003

[17] K L Miller R S Liebowitz and L K Newby ldquoComplementaryand alternative medicine in cardiovascular disease a review ofbiologically based approachesrdquoAmericanHeart Journal vol 147no 3 pp 401ndash411 2004

[18] D L Guo and Z R Luo ldquoGenetic relationships of the Japanesepersimmon Diospyros kaki (Ebenaceae) and related speciesrevealed by SSR analysisrdquo Genetics and Molecular Research vol10 no 2 pp 1060ndash1068 2011

[19] M J Li D Liang F Pu F W Ma C M Hou and T LuldquoAscorbate levels and the activity of key enzymes in ascorbatebiosynthesis and recycling in the leaves of 22 Chinese persim-mon cultivarsrdquo Scientia Horticulturae vol 120 no 2 pp 250ndash256 2009

[20] Z Luo ldquoEffect of 1-methylcyclopropene on ripening of posthar-vest persimmon (Diospyros kaki L) fruitrdquo LWTmdashFood Scienceand Technology vol 40 no 2 pp 285ndash291 2007

Journal of Chemistry 9

[21] A T Oz ldquoCombined effects of 1-methyl cyclopropene (1-MCP)andmodified atmosphere packaging (MAP) on different ripen-ing stages of persimmon fruit during storagerdquo African Journalof Biotechnology vol 10 no 5 pp 807ndash814 2011

[22] M S Akter M Ahmed and J B Eun ldquoDietary fibre compo-nents antioxidant activities and hydration properties of ripepersimmon (Diospyros kaki L cv Daebong) peel powders asaffected by different washing treatmentsrdquo International Journalof Food Science and Technology vol 45 no 7 pp 1464ndash14712010

[23] K Yonemori A Sugiura andM Yamada ldquoPersimmon geneticsand breedingrdquo Plant Breeding Reviews vol 19 pp 191ndash225 2000

[24] P Thomas and T S Chen ldquoQuantitative analyses of majorcarotenoid fatty acid esters in fruits by liquid chromatographypersimmon and papayardquo Journal of Food Science vol 53 no 6pp 1720ndash1722 1988

[25] T Nakagawa A Nakatsuka K Yano et al ldquoExpressed sequencetags from persimmon at different developmental stagesrdquo PlantCell Reports vol 27 no 5 pp 931ndash938 2008

[26] R Veberic J Jurhar M Mikulic-Petkovsek F Stampar andV Schmitzer ldquoComparative study of primary and secondarymetabolites in 11 cultivars of persimmon fruit (Diospyros kakiL)rdquo Food Chemistry vol 119 no 2 pp 477ndash483 2010

[27] A Ikegami S Eguchi A Kitajima K Inoue and K YonemorildquoIdentification of genes involved in proanthocyanidin biosyn-thesis of persimmon (Diospyros kaki) fruitrdquo Plant Science vol172 no 5 pp 1037ndash1047 2007

[28] A Sattar N Bibi and M A Chaudry ldquoPhenolic compoundsin persimmon during maturation and on-tree ripeningrdquo Food Nahrung vol 36 no 5 pp 466ndash472 1992

[29] Y-S Park S-T Jung S-G Kang et al ldquoDrying of persimmons(Diospyros kaki L) and the following changes in the studiedbioactive compounds and the total radical scavenging activi-tiesrdquo LWTmdashFood Science and Technology vol 39 no 7 pp 748ndash755 2006

[30] A Ikegami T Akagi D Potter et al ldquoMolecular identifica-tion of 1-Cys peroxiredoxin and anthocyanidinflavonol 3-O-galactosyltransferase from proanthocyanidin-rich young fruitsof persimmon (Diospyros kakiThunb)rdquo Planta vol 230 no 4pp 841ndash855 2009

[31] T Radha and L Mathew Fruit Crops Horticulture ScienceSeries Jai Baharat Press 2007

[32] H Yakushiji ldquoRecent persimmon research in Japanrdquo JapaneseJournal of Plant Science vol 1 pp 42ndash62 2007

[33] X N Chen J F Fan X Yue X R Wu and L T Li ldquoRadicalscavenging activity and phenolic compounds in persimmon(Diospyros kaki L cv Mopan)rdquo Journal of Food Science vol 73no 1 pp C24ndashC28 2008

[34] H R Wang P Leng and C S Wang ldquoEffect of absorbentson storage quality of the Mopan persimmonrdquo Journal ShanxiAgriculture and Science vol 33 no 1 pp 59ndash61 2005

[35] X H Guo S Z Fang J Wang X X Guo L Q Xu and L YuanldquoStudy on the infection of the Mopan persimmon quality bycarbon dioxiderdquo Food Research Developments vol 27 pp 156ndash159 2006

[36] S Li P Zhang J K Li L Wang and Y F Huang ldquoEffect of1-methylcyclopropene for the Mopan persimmon crispiness-keeping under ambient temperaturerdquo Storing Process vol 6 pp13ndash16 2006

[37] J L Vazquez-Gutierrez I Hernando and A Quiles ldquoChangesin tannin solubility and microstructure of high hydrostaticpressurendashtreated persimmon cubes during storage at 4∘CrdquoEuropean Food Research and Technology vol 237 no 1 pp 9ndash172013

[38] N Bibi A B Khattak and ZMehmood ldquoQuality improvementand shelf life extension of persimmon fruit (Diospyros kaki)rdquoJournal of Food Engineering vol 79 no 4 pp 1359ndash1363 2007

[39] S Kondo H Yoshikawa and R Katayama ldquoAntioxidant activityin astringent and non-astringent persimmonsrdquo Journal of Hor-ticultural Science and Biotechnology vol 79 no 3 pp 390ndash3942004

[40] X Wei F Liu Z Qiu Y Shao and Y He ldquoRipeness classifica-tion of astringent persimmon using hyperspectral imagingtechniquerdquo Food and Bioprocess Technology vol 7 no 5 pp1371ndash1380 2014

[41] K P Wright and A A Kader ldquoEffect of controlled-atmospherestorage on the quality and carotenoid content of sliced persim-mons and peachesrdquo Postharvest Biology and Technology vol 10no 1 pp 89ndash97 1997

[42] P Novillo A Salvador E Llorca I Hernando and C BesadaldquoEffect of CO

2deastringency treatment on flesh disorders

induced by mechanical damage in persimmon Biochemicaland microstructural studiesrdquo Food Chemistry vol 145 pp 454ndash463 2014

[43] C J Xu and S L Zhang ldquoCarotenoid biosynthesis and its regu-lation in plantsrdquo Plant Physiology and Communication vol 36pp 64ndash70 2000

[44] E Bellini G Giannelli and E Picardi ldquoPanoramica varietaledel Kaki nel mondo e orientamenti produttivi per lrsquoItaliardquoLrsquoinformatore Agrario vol 44 no 47 pp 47ndash88 2011

[45] USDA-Agriculture Research Service National AgriculturalLibrary Beltsville Md USA vol 44 pp 47ndash88 1998

[46] M Kawase N Motohashi K Satoh et al ldquoBiological activityof persimmon (Diospyros kaki) peel extractsrdquo PhytotherapyResearch vol 17 no 5 pp 495ndash500 2003

[47] W Bei W Peng Y Ma and A Xu ldquoFlavonoids from the leavesof Diospyros kaki reduce hydrogen peroxide-induced injury ofNG108-15 cellsrdquo Life Sciences vol 76 no 17 pp 1975ndash1988 2005

[48] S-O Lee S-K Chung and I-S Lee ldquoThe antidiabetic effect ofdietary persimmon (Diospyros kaki L cv sangjudungsi) peel instreptozotocin-induced daibetic ratsrdquo Journal of Food Sciencevol 71 no 3 pp S293ndashS298 2006

[49] S Gorinstein Z Zachwieja M Folta et al ldquoComparative con-tents of dietary fiber total phenolics and minerals in persim-mons and applesrdquo Journal of Agricultural and Food Chemistryvol 49 no 2 pp 952ndash957 2001

[50] H Leontowicz S Gorinstein A Lojek et al ldquoComparativecontent of some bioactive compounds in apples peaches andpears and their influence on lipids and antioxidant capacity inratsrdquo Journal of Nutritional Biochemistry vol 13 no 10 pp 603ndash610 2002

[51] Y A Lee E J Cho and T Yokozawa ldquoProtective effect of per-simmon (Diospyros kaki) peel proanthocyanidin against oxida-tive damage under H

2O2-induced cellular senescencerdquo Biolog-

ical and Pharmaceutical Bulletin vol 31 no 6 pp 1265ndash12692008

[52] A Subagio N Morita and S Sawada ldquoCarotenoids and theirfatty-acid esters in banana peelrdquo Journal of Nutritional Scienceand Vitaminology vol 42 no 6 pp 553ndash566 1996

10 Journal of Chemistry

[53] Y J Yang and S J Kim ldquoChanges in chlorophyll and carotenoidcontents during cold and CA storage and characterization ofthe carotenoids in the peel of lsquoFujirsquo apple fruitrdquo Journal of KoreanSociety and Horticultural Science vol 36 pp 500ndash505 1995

[54] Y C Kim J B Kim K J Cho I S Lee and S K ChungldquoCarotenoid content of Korean persimmon peel and theirchanges in storagerdquo Food Science and Biotechnology vol 11 no5 pp 477ndash479 2002

[55] J Tous and L Ferguson ldquoMediterranean fruitsrdquo in Progress inNew Crops J Janick Ed pp 416ndash430 ASHS Press ArlingtonVa USA 1996

[56] B YuanH L Xu and S P Leng ldquoContent and chemical compo-sition of carotenoids in persimmon fruitrdquo Chinese AgriculturalScience Bulletin vol 22 pp 277ndash280 2006 (Chinese)

[57] D Zhao C Zhou and J Tao ldquoCarotenoid accumulation andcarotenogenic genes expression during two types of persimmonfruit (Diospyros kaki L) developmentrdquo Plant Molecular BiologyReporter vol 29 no 3 pp 646ndash654 2011

[58] L Plaza C Colina B D Ancos C Sanchez-Moreno and MPilar Cano ldquoInfluence of ripening and astringency on carote-noid content of high-pressure treated persimmon fruit (Dio-spyros kakiL)rdquo FoodChemistry vol 130 no 3 pp 591ndash597 2012

[59] T Niikawa T Suzuki T Ozeki M Kato and Y Ikoma ldquoChar-acteristics of carotenoid accumulation duringmaturation of theJapanese persimmon lsquoFuyursquordquo Horticultural Research vol 6 pp251ndash256 2007 (Japanese)

[60] G Britton ldquoStructure and properties of carotenoids in relationto functionrdquo The FASEB Journal vol 9 no 15 pp 1551ndash15581995

[61] H G Daood P Biacs B Czinkotai and A Hoschke ldquoChroma-tographic investigation of carotenoids sugars and organic acidsfrom Diospyros kaki fruitsrdquo Food Chemistry vol 45 no 2 pp151ndash155 1992

[62] I-C Jang E-K Jo S-M Bae et al ldquoAntioxidant activity andfatty acid composition of four different persimmon seedsrdquo FoodScience and Technology Research vol 16 no 6 pp 577ndash5842010

[63] J AMenendez L Vellon R Colomer and R Lupu ldquoOleic acidthe main monounsaturated fatty acid of olive oil suppressesHer-2neu (erbB-2) expression and synergistically enhances thegrowth inhibitory effects of trastuzumab (Herceptin) in breastcancer cells with Her-2neu oncogene amplificationrdquo Annals ofOncology vol 16 no 3 pp 359ndash371 2005

[64] W C Willett ldquoThe role of dietary n-6 fatty acids in theprevention of cardiovascular diseaserdquo Journal of CardiovascularMedicine vol 8 no 1 pp S42ndashS45 2007

[65] K Kawakami S Aketa H Sakai Y Watanabe H Nishida andM Hirayama ldquoAntihypertensive and vasorelaxant effects ofwater-soluble proanthocyanidins from persimmon leaf tea inspontaneously hypertensive ratsrdquo Bioscience Biotechnology andBiochemistry vol 75 no 8 pp 1435ndash1439 2011

[66] G Chen J Xue S-X Xu and R-Q Zhang ldquoChemical con-stituents of the leaves of Diospyros kaki and their cytotoxiceffectsrdquo Journal of Asian Natural Products Research vol 9 no4 pp 347ndash353 2007

[67] S Singh and H Joshi ldquoDiospyros kaki (Ebenaceae) a reviewrdquoAsian Journal of Research in Pharmaceutical Science vol 1 no3 pp 55ndash58 2011

[68] J L Navarro A Tarrega M A Sentandreu and E SentandreuldquoPartial purification and characterization of polyphenol oxi-dase from persimmonrdquo Food Chemistry vol 157 pp 283ndash2892014

[69] O V Zillich U Schweiggert-Weisz P Eisner and M KerscherldquoPolyphenols as active ingredients for cosmetic productsrdquoInternational Journal of Cosmetic Science vol 37 no 5 pp 455ndash464 2015

[70] H Palafox-Carlos J F Ayala-Zavala and G A Gonzalez-Aguilar ldquoThe role of dietary fiber in the bioaccessibility andbioavailability of fruit and vegetable antioxidantsrdquo Journal ofFood Science vol 76 no 1 pp R6ndashR15 2011

[71] A Ratz-Łyko J Arct SMajewski andK Pytkowska ldquoInfluenceof polyphenols on the physiological processes in the skinrdquoPhytotherapy Research vol 29 no 4 pp 509ndash517 2015

[72] J Sun Y-F Chu X Wu and R H Liu ldquoAntioxidant andantiproliferative activities of common fruitsrdquo Journal of Agricul-tural and Food Chemistry vol 50 no 25 pp 7449ndash7454 2002

[73] E Sentandreu M Cerdan-Calero J M Halket and J LNavarro ldquoRapid screening of low-molecular-weight phenolsfrom persimmon (Diospyros kaki) pulp using liquid chroma-tographyUVndashvisibleelectrospray mass spectrometry analysisrdquoJournal of the Science of Food and Agriculture vol 95 pp 1648ndash1654 2015

[74] L Bravo ldquoPolyphenols chemistry dietary sources metabolismand nutritional significancerdquo Nutrition Reviews vol 56 no 11pp 317ndash333 1998

[75] T Akagi Y Suzuki A Ikegami et al ldquoCondensed tannin com-position analysis in persimmon (Diospyros kakiThunb) fruit byacid catalysis in the presence of excess phloroglucinolrdquo Journalof the Japanese Society for Horticultural Science vol 79 no 3 pp275ndash281 2010

[76] C Li R Leverence J D Trombley et al ldquoHighmolecularweightpersimmon (Diospyros kaki L) proanthocyanidin a highlygalloylated a-linked tannin with an unusual flavonol terminalunitmyricetinrdquo Journal of Agricultural and FoodChemistry vol58 no 16 pp 9033ndash9042 2010

[77] C A Rice-Evans N J Miller and G Paganga ldquoStructure-antioxidant activity relationships of flavonoids and phenolicacidsrdquo Free Radical Biology andMedicine vol 20 no 7 pp 933ndash956 1996

[78] R Tsao ldquoChemistry and biochemistry of dietary polyphenolsrdquoNutrients vol 2 no 12 pp 1231ndash1246 2010

[79] S Uchida H Ohta R Edamatsu M Hiromatsu A Mori andG I Nomaka ldquoPersimmon tannin prolongs life span of stroke-prone spontaneously hypertensive rats (SHRSP) by acting as afree-radical scavengerrdquo in New Horizons in Preventing Cardio-vascular Diseases Y Yamori and T Strasser Eds pp 15ndash17Academic Press Amsterdam The Netherlands Elsevier NewYork NY USA 1989

[80] S Uchida H Ohta M Niwa et al ldquoProlongation of life spanof stroke-prone spontaneously hypertensive rats (SHRSP)ingesting persimmon tanninrdquo Chemical and PharmaceuticalBulletin vol 38 no 4 pp 1049ndash1052 1990

[81] S Gorinstein G W Kulasek E Bartnikowska et al ldquoThe influ-ence of persimmon peel and persimmon pulp on the lipidmeta-bolism and antioxidant activity of rats fed cholesterolrdquo Journalof Nutritional Biochemistry vol 9 no 4 pp 223ndash227 1998

[82] K Matsumoto A Kadowaki N Ozaki et al ldquoBile acid-bind-ing ability of kaki-tannin from young fruits of persimmon (Dio-spyros kaki) in vitro and in vivordquo Phytotherapy Research vol 25no 4 pp 624ndash628 2011

[83] K Ueda R Kawabata T Irie Y Nakai Y Tohya and T Sak-aguchi ldquoInactivation of pathogenic viruses by plant-derivedtannins strong effects of extracts from persimmon (Diospyros

Journal of Chemistry 11

kaki) on a broad range of virusesrdquo PLoS ONE vol 8 no 1Article ID e55343 10 pages 2013

[84] H Suzuki M Konishi M Kimura T Mori M Suzuki and TIkemi ldquoInhibitory effects ofDiospyros kakiTHUNB Extracts indental caries in ratsrdquo Japanese Journal of Conservative Dentistryvol 50 no 2 pp 140ndash145 2007

[85] S Sakanaka Y Tachibana and Y Okada ldquoPreparation andantioxidant properties of extracts of Japanese persimmon leaftea (Kakinoha-cha)rdquo Food Chemistry vol 89 no 4 pp 569ndash5752005

[86] MHosny and J PN Rosazza ldquoNovel oxidations of (+)-catechinby horseradish peroxidase and laccaserdquo Journal of Agriculturaland Food Chemistry vol 50 no 20 pp 5539ndash5545 2002

[87] J-I Inokuchi H Okabe T Yamauchi and A NagamatsuldquoInhibitors of angiotensin converting enzyme in crude drugsrdquoChemical and Pharmaceutical Bulletin vol 32 no 9 pp 3615ndash3619 1984

[88] Y Tian B Zou L Yang et al ldquoHigh molecular weight per-simmon tannin ameliorates cognition deficits and attenuatesoxidative damage in senescent mice induced by d-galactoserdquoFood andChemical Toxicology vol 49 no 8 pp 1728ndash1736 2011

[89] Y Achiwa H Hibasami H Katsuzaki K Imai and T KomiyaldquoInhibitory effects of persimmon (Diospyros kaki) extract andrelated polyphenol compounds on growth of human lymphoidleukemia cellsrdquo Bioscience Biotechnology and Biochemistry vol61 no 7 pp 1099ndash1101 1997

[90] J Gross Carotenoids vol 123 Academic Press New York NYUSA 1987

[91] B De Ancos E Gonzalez and M P Cano ldquoEffect of high-pressure treatment on the carotenoid composition and theradical scavenging activity of persimmon fruit pureesrdquo Journalof Agricultural and Food Chemistry vol 48 no 8 pp 3542ndash3548 2000

[92] T Matsuo and S Ito ldquoThe chemical structure of Kaki-tanninfrom immature fruit of the persimmon (Diospyros kaki L)rdquoAgricultural and Biological Chemistry vol 42 no 9 pp 1637ndash1643 1978

[93] S Gorinstein M Zemser M Weisz et al ldquoFluorometric anal-ysis of phenolics in persimmonsrdquo Bioscience Biotechnology andBiochemistry vol 58 no 6 pp 1087ndash1092 1994

[94] S O Lee H J LeeMH Yu H G Im and I S Lee ldquoTotal poly-phenol contents and antioxidant activities of methanol extractsfrom vegetables produced in Ullung Islandrdquo Korean Journal ofFood Science and Technology vol 37 no 2 pp 233ndash240 2005

[95] U V Mallavadhani A K Panda and Y R Rao ldquoPharmacologyand chemotaxonomy of Diospyrosrdquo Phytochemistry vol 49 no4 pp 901ndash951 1998

[96] G Block B Patterson and A Subar ldquoFruit vegetables andcancer prevention a review of the epidemiological evidencerdquoNutrition and Cancer vol 18 no 1 pp 1ndash29 1992

[97] G van Poppel ldquoCarotenoids and cancer an updatewith empha-sis on human intervention studiesrdquo European Journal of Cancervol 29 no 9 pp 1335ndash1344 1993

[98] E Giovannucci A Ascherio E B Rimm M J Stampfer G AColditz and W C Willett ldquoIntake of carotenoids and retino inrelation to risk of prostate cancerrdquo Journal of theNational CancerInstitute vol 87 no 23 pp 1767ndash1776 1995

[99] T Johns R L A Mahunnah P Sanaya L Chapman and TTicktin ldquoSaponins and phenolic content in plant dietary addi-tives of a traditional subsistence community the Batemi ofNgorongoro District Tanzaniardquo Journal of Ethnopharmacologyvol 66 no 1 pp 1ndash10 1999

[100] Y Zhang X Lu Y Zhang L Qin and J Zhang ldquoSulfatedmodification and immunomodulatory activity of water-solublepolysaccharides derived from fresh Chinese persimmon fruitrdquoInternational Journal of Biological Macromolecules vol 46 no1 pp 67ndash71 2010

[101] Y-J Moon and Y-S Cha ldquoEffects of persimmon-vinegar onlipid metabolism and alcohol clearance in chronic alcohol-fedratsrdquo Journal of Medicinal Food vol 11 no 1 pp 38ndash45 2008

[102] H S Ahn T I Jeon J Y Lee S G Hwang Y Lim and D KPark ldquoAntioxidative activity of persimmon and grape seedextract in vitro and in vivordquo Nutrition Research vol 22 no 11pp 1265ndash1273 2002

[103] H Itamurah N Murakami and H Nagamatsu ldquoProperty ofkaki-tannin as a functional composition in persimmon fruitflesh and leaves and its solubility in artificial stomach liquidrdquoin Proceedings of the 27th International Horticultural Congressamp Exhibition (IHC rsquo06) vol 8 pp 265ndash267 August 2006

[104] K A Steinmetz and J D Potter ldquoVegetables fruit and cancerprevention a reviewrdquo Journal of the American Dietetic Associa-tion vol 96 no 10 pp 1027ndash1039 1996

[105] A N Nagappa P A Thakurdesai N V Rao and J SinghldquoAntidiabetic activity ofTerminalia catappa Linn fruitsrdquo Journalof Ethnopharmacology vol 88 no 1 pp 45ndash50 2003

[106] K Datta S Sinha and P Chattopadhyay ldquoReactive oxygenspecies in health and diseaserdquoNationalMedical Journal of Indiavol 13 no 6 pp 304ndash310 2000

[107] R R Holman and R C Turner ldquoOral agents and insulin in thetreatment of NIDDMrdquo in Textbook of Diabetes J Williams Edpp 407ndash469 Blackwell Press Oxford UK 1991

[108] F Giacco and M Brownlee ldquoOxidative stress and diabeticcomplicationsrdquo Circulation Research vol 107 no 9 pp 1058ndash1070 2010

[109] B K Rao M M Kesavulu R Giri and C A Rao ldquoAntidiabeticand hypolipidemic effects ofMomordicacymbalariaHook fruitpowder in alloxan-diabetic ratsrdquo Journal of Ethnopharmacologyvol 67 no 1 pp 103ndash109 1999

[110] J K Grover V Vats V Rathi and S S Dawar ldquoTraditionalIndian anti-diabetic plants attenuate progression of renal dam-age in streptozotocin induced diabetic micerdquo Journal of Ethno-pharmacology vol 76 no 3 pp 233ndash238 2001

[111] R K Gupta A N Kesari P S Murthy R Chandra V Tandonand GWatal ldquoHypoglycemic and antidiabetic effect of ethano-lic extract of leaves of Annona squamosa L in experimentalanimalsrdquo Journal of Ethnopharmacology vol 99 no 1 pp 75ndash81 2005

[112] S Gupta N Ahmad A-L Nieminen andHMukhtar ldquoGrowthinhibition cell-cycle dysregulation and induction of apopto-sis by green tea constituent (-)-epigallocatechin-3-gallate inandrogen-sensitive and androgen-insensitive human prostatecarcinoma cellsrdquoToxicology andApplied Pharmacology vol 164no 1 pp 82ndash90 2000

[113] T Yokozawa Y A Kim H Y Kim Y A Lee and G-I NonakaldquoProtective effect of persimmon peel polyphenol against highglucose-induced oxidative stress in LLC-PK1 cellsrdquo Food andChemical Toxicology vol 45 no 10 pp 1979ndash1987 2007

12 Journal of Chemistry

[114] M S Brewer ldquoNatural antioxidants sources compoundsmechanisms of action and potential applicationsrdquo Comprehen-sive Reviews in Food Science and Food Safety vol 10 no 4 pp221ndash247 2011

[115] K Kawakami H Nishida N Tatewaki Y Nakajima T Konishiand M Hirayama ldquoPersimmon leaf extract inhibits the ATMactivity during DNA damage response induced by Doxorubicinin A549 lung adenocarcinoma cellsrdquo Bioscience Biotechnologyand Biochemistry vol 75 no 4 pp 650ndash655 2011

[116] D Steinberg S Parthasarathy T E Carew J C Khoo and JL Witztum ldquoBeyond cholesterol modifications of low-densitylipoprotein that increase its atherogenicityrdquo The New EnglandJournal of Medicine vol 320 no 14 pp 915ndash924 1989

[117] P M Kris-Etherton and C L Keen ldquoEvidence that the anti-oxidant flavonoids in tea and cocoa are beneficial for cardiovas-cular healthrdquo Current Opinion in Lipidology vol 13 no 1 pp41ndash49 2002

[118] C Manach A Mazur and A Scalbert ldquoPolyphenols and pre-vention of cardiovascular diseasesrdquo Current Opinion in Lipidol-ogy vol 16 no 1 pp 77ndash84 2005

[119] J W Anderson B M Smith and N J Gustafson ldquoHealthbenefits and practical aspects of high-fiber dietsrdquo AmericanJournal of Clinical Nutrition vol 59 no 5 pp 1242ndash1247 1994

[120] D Kromhout A Menotti H Kesteloot and S Sans ldquoPreven-tion of coronary heart disease by diet and lifestyle evidencefrom prospective cross-cultural cohort and intervention stud-iesrdquo Circulation vol 105 no 7 pp 893ndash898 2002

[121] E B Rimm M J Stampfer A Ascherio E Giovannucci G AColditz andWCWillett ldquoVitamin E consumption and the riskof coronary heart disease in menrdquo The New England Journal ofMedicine vol 328 no 20 pp 1450ndash1456 1993

[122] L Dauchet J Ferrieres D Arveiler et al ldquoFrequency of fruitand vegetable consumption and coronary heart disease inFrance and Northern Ireland the prime studyrdquo British Journalof Nutrition vol 92 no 6 pp 963ndash972 2004

[123] S Gorinstein GW Kulasek E Bartnikowska et al ldquoThe effectsof diets supplementedwith either whole persimmon or phenol-free persimmon on rats fed cholesterolrdquo Food Chemistry vol70 no 3 pp 303ndash308 2000

[124] M G L Hertog E J M Feskens P C H HollmanM B Katanand D Kromhout ldquoDietary antioxidant flavonoids and risk ofcoronary heart disease the Zutphen Elderly studyrdquoThe Lancetvol 342 no 8878 pp 1007ndash1011 1993

[125] H Seo B D Jeon andR Sungpil ldquoPersimmon vinegar ripeningwith the mountain-cultivated ginseng ingestion reduces bloodlipids and lowers inflammatory cytokines in obese adolescentsrdquoJournal of Exercise Nutrition and Biochemistry vol 19 no 1 pp1ndash10 2015

[126] R H Liu ldquoPotential synergy of phytochemicals in cancerprevention mechanism of actionrdquo Journal of Nutrition vol 134no 12 supplement pp 3479Sndash3485S 2004

[127] S T Mayne ldquoAntioxidant nutrients and chronic disease use ofbiomarkers of exposure and oxidative stress status in epidemi-ologic researchrdquo Journal of Nutrition vol 133 no 3 pp 933sndash940s 2003

[128] H Tapiero D M Townsend and K D Tew ldquoThe role of caro-tenoids in the prevention of human pathologiesrdquo Biomedicineand Pharmacotherapy vol 58 no 2 pp 100ndash110 2004

[129] J Tao and S L Zhang ldquoMetabolismof carotenoid and its regula-tion in garden croprdquo Journal of Zhejiang University (Agricultureamp Life Sciences) vol 29 pp 585ndash590 2003

[130] W Miki ldquoBiological functions and activities of animal caro-tenoidsrdquo Pure and Applied Chemistry vol 63 no 1 pp 141ndash1461991

[131] H Fujiki ldquoGreen tea health benefits as cancer preventive forhumansrdquo Chemical Record vol 5 no 3 pp 119ndash132 2005

[132] A P George and S Redpath ldquoHealth and medicinal benefits ofpersimmon fruit a reviewrdquo Advances in Horticultural Sciencevol 22 no 4 pp 244ndash249 2008

[133] T Hussain S Gupta V M Adhami and H Mukhtar ldquoGreentea constituent epigallocatechin-3-gallate selectively inhibitsCOX-2 without affecting COX-1 expression in human prostatecarcinoma cellsrdquo International Journal of Cancer vol 113 no 4pp 660ndash669 2005

[134] Y-C Wang and U Bachrach ldquoThe specific anti-cancer activityof green tea (minus)-epigallocatechin-3-gallate (EGCG)rdquo AminoAcids vol 22 no 2 pp 131ndash143 2002

[135] O Takayuki ldquoPersimmons your healthy autumn treatsrdquoAsahikawa Information vol 108 pp 1ndash2 2005

[136] T Fukuda and H Shibata ldquoPersimmon calyx extracts as anti-convulsants and to alleviate the side effects of barbituric acidcompoundsrdquo Patent Japanease Kokai Tokkyo Koho vol 6 pp649ndash653 1994

[137] T Matsuno ldquoXanthophylls as precursors of retinoidsrdquo Pure andApplied Chemistry vol 63 no 1 pp 81ndash88 1991

[138] N Gato A Kadowaki N Hashimoto S-I Yokoyama and KMatsumoto ldquoPersimmon fruit tannin-rich fiber reduces choles-terol levels in humansrdquoAnnals of Nutrition andMetabolism vol62 no 1 pp 1ndash6 2013

[139] A Nagao ldquoAbsorption and function of dietary carotenoidsrdquoForum of Nutrition vol 61 pp 55ndash63 2009

[140] PD Fraser andPM Bramley ldquoThebiosynthesis andnutritionaluses of carotenoidsrdquo Progress in Lipid Research vol 43 no 3 pp228ndash265 2004

[141] D Fusco G Colloca M R Lo Monaco and M Cesari ldquoEffectsof antioxidant supplementation on the aging processrdquo ClinicalInterventions in Aging vol 2 no 3 pp 377ndash387 2007

[142] JM Seddon U Ajan and R D Sperduto ldquoDietary carotenoidsvitamins A C and E and advance age-related macular degen-eration Eye Disease Case Study Grouprdquo Journal of AmericanMedical Association vol 272 no 18 pp 1413ndash1420 1992

[143] B-J An J-H Kwak J-M Park et al ldquoInhibition of enzymeactivities and the antiwrinkle effect of polyphenol isolated fromthe persimmon leaf (Diospyros kaki folium) on human skinrdquoDermatologic Surgery vol 31 no 7 pp 848ndash854 2005

[144] H Arakawa M Takasaki N Tajima H Fukamachi and TIgarashi ldquoAntibacterial activities of persimmon extracts relatewith their hydrogen peroxide concentrationrdquo Biological andPharmaceutical Bulletin vol 37 no 7 pp 1119ndash1123 2014

[145] S D Ladas D Kamberoglou G Karamanolis J Vlachogian-nakos and I Zouboulis-Vafiadis ldquoSystematic review Coca-Cola can effectively dissolve gastric phytobezoars as a first-linetreatmentrdquo Alimentary Pharmacology and Therapeutics vol 37no 2 pp 169ndash173 2013

[146] T J Cifuentes C R Robles P P Parrilla et al ldquoPolyphenols andhealth what compounds are involvedrdquo Nutrition Metabolismand Cardiovascular Diseases vol 20 no 1 pp 1ndash6 2010

[147] J Gaya L Barranco A Llompart J Reyes and A ObradorldquoPersimmon bezoars a successful combined therapyrdquoGastroin-testinal Endoscopy vol 55 no 4 pp 581ndash583 2002

[148] P G Hayes and O D Rotstein ldquoGastrointestinal phytobezoarspresentation and managementrdquo Canadian Journal of Surgeryvol 29 no 6 pp 419ndash420 1986

Journal of Chemistry 13

[149] MM Krausz E ZMoriel A Ayalon D Pode and A L DurstldquoSurgical aspects of gastrointestinal persimmon phytobezoartreatmentrdquoThe American Journal of Surgery vol 152 no 5 pp526ndash530 1986

[150] P Walker-Renard ldquoUpdate on the medicinal management ofphytobezoarsrdquo The American Journal of Gastroenterology vol88 no 10 pp 1663ndash1666 1993

[151] S S Ha H S LeeM K Jung et al ldquoAcute intestinal obstructioncaused by a persimmon phytobezoar after dissolution therapywith Coca-Colardquo The Korean Journal of Internal Medicine vol22 no 4 pp 300ndash303 2007

[152] J Han S Kang R Choue et al ldquoFree radical scavenging effectofDiospyros kaki Laminaria japonica andUndaria pinnatifidardquoFitoterapia vol 73 no 7-8 pp 710ndash712 2002

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Page 5: Review Article Chemistry and Functionality of Bioactive ...downloads.hindawi.com/journals/jchem/2016/3424025.pdf · Review Article Chemistry and Functionality of Bioactive Compounds

Journal of Chemistry 5

with phloroglucinol They characterized this component asnovel epigallocatechin-3-O-gallate-phloroglucinol (EGCG-P) adduct Li et al [76] also reported that the persimmon pulpis comprised of flavan-3-O-galloylated extenders flavan-3-ol and flavonol terminal units and A-type interflavanlinkages which are condensed tannins with high-molecularweight

Structurally phenols contain an aromatic ring havinghydroxyl substituents ranging from simple to highly poly-merized compounds [77] The naturally present compoundsform linkages with saccharides and might be functionalderivatives like esters and methyl esters Hence the extensivevariety of phenolic compounds occurring in nature is theresult of this structural assortment These compounds arecategorized in several groups Out of them phenolic acidsflavonoids and tannins are considered as the main dietarycomponents [78]

Phenolic acids are non-flavonoid polyphenolic com-pounds comprised of 2 subgroups hydroxybenzoic andhydroxycinnamic acids Hydroxybenzoic acids contain gal-lic p-hydroxybenzoic protocatechuic vanillic and syringicacids in which they all have the C6ndashC1 structure Hydrox-ycinnamic acids instead are aromatic compounds like caf-feic ferulic p-coumaric and sinapic acids with a 3-carbon(C6ndashC3) side chain [78] The structure of phenolic com-pounds is a vital factor affecting radical-scavenging andmetalchelating activities and hence it is referred to as having astructurendashactivity relationship In the case of phenolic acidsthe antioxidant activity is influenced by the numbers andpositions of the hydroxyl groups with respect to the carboxylfunctional group [47] Hence they give their hydrogen atomsto scavenge free radicals as shown in Figure 1

Flavonoids have the C6ndashC3ndashC6 general structural back-bone in which the two C6 units (Ring A and Ring B) areof phenolic nature Flavonoids can be further divided intodifferent subgroups on basis of variations in chromane ringand hydroxylation pattern Flavonoids can be further dividedinto different subgroups such as anthocyanins flavan-3-olsflavones flavanones and flavonols While the vast majorityof the flavonoids have their Ring B attached to the C2position of Ring C these basic structures of flavonoids areaglycones however in plants most of these compoundsexist as glycosides Biological activities of these compoundsincluding antioxidant activity depend on both the structuralvariation and the glycosylation patterns [79]

Tannins the third important group of phenolics aresegmented as hydrolysable and condensed tannins which areesters of gallic acid and polymers of polyhydroxyflavan-3-ol monomers respectivelyThe third segment phlorotanninscomprised of phloroglucinol is found in brown algae How-ever these are insignificant regarding human diet [75 76]Tannins are present in persimmonprolonged life and reducedthe incidence of stroke in hypertensive rats [80 81]This effectwas attributed to the fact that persimmon tannins are 20 timesmore potent than antioxidant vitamin E [82]The persimmontannin is composed mostly of epicatechin epicatechin-3-O-gallate epigallocatechin and epigallocatechin-3-O-gallate[83]

7 Therapeutic Effects of Persimmon

Persimmon has been used for various medicinal purposes(Table 2) owing to the therapeutic properties such as diureticeffect blood pressure-lowering capability and the coughtreatment viral and bacterial infectious diseases [84] anddental caries [85] Various bioactive compounds includingpolyphenols carotenoids vitamins and dietary fiber in thefruit are responsible for beneficial properties [49] Subagioet al [52] reported the protective effect of proanthocyanidinfrompersimmon peel against DNAdamage and SIRT expres-sion in the aging process

The persimmon leaves are a good source of antioxidants[102] while the seed extracts have a strong radical-scavengingactivity [104] The fruits are a rich source of dietary carote-noids (a-carotene a-cryptoxanthin zeaxanthin lutein andlycopene) which have been implicated in the reduction ofdegenerative human diseases [91] The concentration of a-carotene and a-cryptoxanthin is so high that 100 g of pulpprovides 10 of the recommend daily allowance provitaminA [105]

Persimmon fruit can be used in the manufacturing ofproducts with functional characteristics because of its bioac-tive properties It is an excellent source of ascorbic acid tan-nins and carotenoids having healthy aspects owing to theirantioxidant and other health protecting activities [6]

71 Diabetes Diabetes mellitus is a chronic disease and thereason behind that is inherited andor acquired insufficientinsulin production by the pancreas or by the incompetenceof the insulin produced Such a deficiency results in raisedconcentrations of glucose in the blood which sequentiallydamage many of the bodyrsquos systems particularly the bloodvessels and nerves [106] When bodyrsquos defense systems nei-ther detoxify the reactive intermediates nor repair the result-ing damage from reactive oxygen species (ROS) then such animbalance condition is known as oxidative stress responsiblefor diabetes mellitus and related complications [107]

Along with insulin many other agents like sulfonylureaand biguanide can be used to reduce blood glucose levelin order to treat diabetes These hypoglycemic agents haveconsiderable side effects [108] In chronic diabetes thesehypoglycemic agents sometimes become ineffective [109]Therefore the demand of such hypoglycemic agents whichhave side effects and are either made artificially or fromnatural source is decreasing day by day [110] Hence there isneed of natural agents like plant and plant based materialswhich can show more potential for control and treatment ofdiabetes and its complications with no side effects [111] Sinceseveral years herbal remedies including different medicinalplants or their extracts have been taken orally in order totreat diabetes The search for effective natural hypoglycemicagent is under consideration as recommended by WHO[112] Recently great attention has been paid to a numberof nonvitamin antioxidants widely distributed in naturalsources like fruit vegetables and spices having the abilityto enhance the antioxidative defense mechanism at cellularlevel without side effects [113]Themain group of compoundsthat act primarily as free radical terminator or antioxidants isplant phenolics

6 Journal of Chemistry

Table 2 Various bioactive compounds present in persimmon and their functional properties

Source Health benefits ReferenceExtracted polyphenol119901-Coumaric Prevention of oxidative stress related diseases including diabetes [86]Tannins Scavenging action against active oxygen free radicals [82 87 88]

Tannin Assists the neuronal degeneration and karyopyknosis in cells reduction ofthickness of skin epidermis [89]

Flavonoids Scavenging action against active oxygen free radicals [82 87 88]Persimmon fruit

Whole fruit

Possesses antitumor effects due to betulinic acid [47 90]Blood pressure-lowering and diuretic effects also effective for coughs treatment [91]Has antioxidative potentials due to compounds like vitamin A beta-carotenelycopene lutein zeaxanthin and cryptoxanthin [92]

Exhibits hypolipidemic and antioxidant properties [50 82]Contains nutritional antioxidant vitamins polyphenols and dietary fiber [93 94]Reduction of patches of pigmentation on skin [95]Has ability to dilate the blood vessels near the surface of the skin thereby allowingmore blood to flow through the skin where it can be cooled by the air (antifebrile) [96]

Reduction of degenerative disease in human beings [91 97ndash99]Fruit peel powder Pharmacological potential such as antioxidant and hypocholesterolemic [51 95 100]Water-solublepolysaccharides extractedfrom persimmon fruits

Have ability to alter or regulate immune functions (immunomodulatory activity) [85]

Persimmon vinegar Has antitumor and antioxidative effects and also prevents metabolic disorderinduced by chronic alcohol administration [101]

Plant and leaf extracts

Persimmon leaf tea Prevents hardening of the arteries which ultimately lowers the blood pressure [95]Good source of natural antioxidants [102]

Persimmon plant extracts Contain antitumor and multidrug resistance-reversing agentsStop oxidative damage of DNA [47]

Persimmon calyx extracts Anticonvulsants [103]Persimmon plantsupplemented to a diet Hypocholesterolemic and antioxidative effects [82]

Persimmon seeds Contain omega 6 fatty acids like palmitic acid oleic acid and linoleic acid [63]Radical-scavenging activity [104]

Among fruits persimmon is comprised of a large numberof biologically active polyphenols like tannins and flavonoidshaving good antioxidant potential These polyphenols pre-vent the diabetes resulting from oxidative stress [86] sincethese work as antioxidants preventing the peroxidation oflipids by the donation of a hydrogen atom from hydroxylgroup attached to their chemical structure rapidly and formperoxyl radical (ROO) that ultimately leads to the formationof alkyl (aryl) hydroperoxide (ROOH) as shown in thefollowing reaction

ROOminus + PPH 997888rarr ROOH + PPminus (1)

The phenolic antioxidant (PPH) itself changes intopolyphenol phenoxyl radical (PP) which becomes stable afterdonating a hydrogen atom by conversion into quinines andit hinders the initiation of new chain reaction by reactingwith another radical inwhich another phenoxyl radical is alsoincluded [114 115]

Gorinstein et al [49] reported that a 2-week intake ofpersimmon peel supplemented diet considerably reducesfood intake blood glucose total cholesterol and plasmatriglycerides level in diabeticsThe researchers concluded thatpersimmon peel rich in high level of antioxidant and dietaryfiber with antidiabetic properties may be characterized asa possible nutritional supplement for improving diabeticcomplications and hyperglycemia

In fresh persimmon leaves most of the polyphenols arefound to be water soluble The chief components in persim-mon leaf tea are unique proanthocyanidin oligomers andoral administration of this tea along with starch resulted in adose-dependent decline in the blood glucose level in Wistarrats [116]

72 Atherosclerosis Inflammation and high levels of oxida-tive stress are a major initiator of cardiovascular diseaseslike atherosclerosis that ultimately leads to coronary artery

Journal of Chemistry 7

disease (CAD) In such condition the oxidative stress is char-acterized by the accumulation of metabolites (from the oxi-dation of proteins and lipids) and macrophages Accordingto the hypothesis of oxidative modification the early eventwhich initiates the development of atherogenesis (develop-ment of atheromatous plaques) is the oxidative breakdownof low-density lipoproteins Reactive oxygen species in thevessel wall have been considered to be one of the mostimportant causes of vascular dysfunction [117]

Dietary components having antioxidant properties as thepolyphenols are receiving a lot of attention because of theirability to reduce cardiovascular diseases [118 119] When dietrich in fiber is largely consumed it results in preventionand treatment of diverticular and coronary heart diseases[120] Coronary atherosclerosis especially is inhibited bypreventing oxidation of low-density lipoprotein (LDL) and bynutritional antioxidants like phenolics [121] and vitamins AC and E [122]

Hence many reports have shown that if intake of veg-etables and fruits is increased in diet then chances of coro-nary heart diseases could greatly be reduced [123] Accord-ing to Hertog et al [124] if 100 g of persimmon is con-sumed regularly then it will be sufficient to inhibit occlu-sion of arteries In young fruits of persimmon (Diospyroskaki) tannin is found to have the ability of bonding bile acid[83]

It has been established that addition of persimmon inthe diet hinders the increase in plasma lipid level and henceworks as antiatherosclerosis [80 124] which reduces thechances of mortality by the action of polyphenols [125]Matsumoto et al [82] also reported that the persimmon peelsupplemented diet shows hypocholesterolemic and antiox-idative effect

Total dietary fibers including soluble and insoluble totalphenolics including epicatechin gallic and p-coumaric acidsand concentrations of minerals like Na K Mg Ca Feand Mn are high in peel pulp and whole persimmon fruitcompared to apple [50] Hence persimmon must be givenpreference over apples and some other fruits in selecting anantiatherosclerotic diet Liu [126] reported decline in bloodtriglyceride and total cholesterol contents after intake ofpersimmon vinegar (PV) for 6 weeks

73 Cancer In recent years persimmon has been thefocus of attention for potential medicinal applications forprevention of cancer [47] Carotenoids are naturersquos mostwidespread pigments and have also received substantialattention because of both their provitamin and antioxidantroles [127] Carotenoids possess antioxidant properties thathave been associatedwith cellular protection [128] regulationof cell growth differentiation and apoptosis [129]

Not only are the carotenoid contents responsible forthe superficial appearance (color) and nutritional quality offruit [130] but also they provide potential health benefitsand disease prevention by quenching singlet oxygen andscavenging free radicals [131] Chemoprotective effects ofpersimmon against various forms of cancer are due to thecarotenoid contents [132 133] Persimmon was shown tobe effective in the treatment of prostate and breast cancers

[134] oral carcinoma cells [47] human lymphoid leukemiacells [135] and precancerous colon polyps in women [136]The bioactive compounds in persimmon may also affectmultidrug resistant (MDR) inhibiting activity It enhances theaccumulation of cancer cells due to the reduced activity ofefflux pumps MDR inhibitors from persimmon may helpto treat noncurable cancer because of the modulating effects[47] The calyx (persimmon) extracts act as anticonvulsantsand may alleviate the side effects of barbituric acid com-pounds [103]

8 Other Health Promoting Properties

Dried persimmon snacks were found to be effective inreducing the concentration of alcohol in the blood [55]Similarly Matsuno [137] observed that kaki-tannin foundin persimmon fruit flesh and leaves was soluble in artifi-cial stomach liquid and reduced blood alcohol (40) andacetaldehyde contents (30) Dietary intake of persimmontannin was found to prevent hypercholesterolemia in someanimal models and humans [138]

Some carotenoids present in persimmon are precur-sors of vitamin A [139] and also have immunoregulatory[140] and antiaging effects [141] Carotenoids are inverselylinked with inflammation atherosclerosis cardiovasculardiseases sarcopenia and mortality Carotenoid supplemen-tation improves the antioxidant status and reduces lipidperoxidation

Carotenoids like 120573-carotene 120572-carotene 120573-cryptoxan-thin lycopene and lutein (Figure 2) have been found to beassociated with inflammation and mortality risks [142] Inaddition lutein (carotenoids) present in persimmon peel canhelp protect eye vision [143]

9 Persimmon Leaves and Health

Persimmon leaves and extracts are being used as a greentea oriental medicines deodorants antiallergic substratesand cosmetics (especially for dermatitis) as they prevent skinproblems and have an antiwrinkle effect [68 143] and skinwhitening effect [72] The leaves are brewed into a beverageto release their antioxidant activity and antitumor effects andto inhibit angiotensin converting enzymes as well as alphaamylase [66] The leaves of persimmon possess antithrom-botic activity Arakawa et al [144] demonstrated that a 10000D anticoagulant fraction has been purified from the leavesthat inhibited thrombin-catalyzed fibrin formation with acompetitive inhibition pattern Based on their antimicrobialproperties persimmon leaf-based products have been incor-porated into athletersquos foot socks and soaps and persimmonleaves have been used as a sushi ingredient [145]

10 Unripen Persimmons and Health Issues

Bezoars are thick hard masses formed in gastrointestinaltract usually the stomach [146] Patients who have undergonestomach surgery and have delayed gastric emptying areoften more prone to the development of bezoars [147]Phytobezoars are the most common types of bezoars and

8 Journal of Chemistry

these are composed of skins seeds and vegetative matterincluding lignin cellulose hemicelluloses tannins and othernondigestible matter from fruits and vegetables ingestedDiospyrobezoars are a type of phytobezoars related to theconsumption of persimmon fruit and are common world-wide These are more difficult to treat because of their hardconsistency [146 148 149] Most bezoars in animals arecaused by hairs

When unripe astringent persimmon having a high levelof tannin is ingested a coagulum is formed in the stomachdue to the contact of tannin and shibuol with hydrochloricacid that accumulates cellulose hemicellulose and pro-tein [150] Phytobezoars may require surgical removal orendoscopic treatment as they are usually resistant to drugtreatment [151] Han et al [152] suggested a nonsurgicalapproach for cases of persimmon phytobezoar small intesti-nal obstruction with its partial dissolution of a bezoar byperforming oral and injected Coca-Cola therapy

11 Conclusion

Bioactive compounds particularly phenolics (ferulic p-coumaric and gallic acids) and carotenoids (120573-cryptoxan-thin lycopene 120573-carotene and lutein) are of major interestsin persimmon fruitThese valued bioactive components havestrong antioxidant potential which relates to the variety stageof maturity and fruit parts These functional compoundscan play a significant role in preventing and curing variousailments like diabetes hypercholesterolemia and cancerHence the known impact of natural bioactive compounds toimprove human health has introduced a substantial area ofresearch resulting in extensive advances in biochemical andnutritional sciences

Conflict of Interests

The authors declare that there is no conflict of interestsregarding the publication of this paper

References

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[2] S Yaqub U Farooq T Kausar Z Hayat M Jaskani and S MUllah ldquoHypocholestrolemic effect of persimmon peel powderin rabbitsrdquo Journal of Science International vol 25 no 3 pp605ndash609 2013

[3] M S Butt M T Sultan M Aziz et al ldquoPersimmon (Piospyroskaki) fruit hidden phytochemicals and health claimsrdquo EXCLIJournal vol 14 pp 542ndash561 2015

[4] A H A Hadi M E Duru and A B Martin-Diana ldquoBioactivenatural productsrdquo Journal of Chemistry vol 2013 Article ID208507 1 page 2013

[5] M R Segura Campos J Ruiz Ruiz L Chel-Guerrero and DBetancur Ancona ldquoCoccoloba uvifera (L)(Polygonaceae) fruitphytochemical screening and potential antioxidant activityrdquoJournal of Chemistry vol 2015 Article ID 534954 9 pages 2015

[6] S Karaman O S Toker F Yuksel M Cam A Kayacier andM Dogan ldquoPhysicochemical bioactive and sensory propertiesof persimmon-based ice cream technique for order prefer-ence by similarity to ideal solution to determine optimum con-centrationrdquo Journal of Dairy Science vol 97 no 1 pp 97ndash1102014

[7] M C Caruso F Galgano M Pecora R Tolve M Verrastroand F Favati ldquoImprovement of analytical methods for thedetermination of polyphenolic bioactive compounds in berryfruitsrdquo Journal of Chemistry vol 2015 Article ID 384051 6pages 2015

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[34] H R Wang P Leng and C S Wang ldquoEffect of absorbentson storage quality of the Mopan persimmonrdquo Journal ShanxiAgriculture and Science vol 33 no 1 pp 59ndash61 2005

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[38] N Bibi A B Khattak and ZMehmood ldquoQuality improvementand shelf life extension of persimmon fruit (Diospyros kaki)rdquoJournal of Food Engineering vol 79 no 4 pp 1359ndash1363 2007

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[48] S-O Lee S-K Chung and I-S Lee ldquoThe antidiabetic effect ofdietary persimmon (Diospyros kaki L cv sangjudungsi) peel instreptozotocin-induced daibetic ratsrdquo Journal of Food Sciencevol 71 no 3 pp S293ndashS298 2006

[49] S Gorinstein Z Zachwieja M Folta et al ldquoComparative con-tents of dietary fiber total phenolics and minerals in persim-mons and applesrdquo Journal of Agricultural and Food Chemistryvol 49 no 2 pp 952ndash957 2001

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2O2-induced cellular senescencerdquo Biolog-

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10 Journal of Chemistry

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[64] W C Willett ldquoThe role of dietary n-6 fatty acids in theprevention of cardiovascular diseaserdquo Journal of CardiovascularMedicine vol 8 no 1 pp S42ndashS45 2007

[65] K Kawakami S Aketa H Sakai Y Watanabe H Nishida andM Hirayama ldquoAntihypertensive and vasorelaxant effects ofwater-soluble proanthocyanidins from persimmon leaf tea inspontaneously hypertensive ratsrdquo Bioscience Biotechnology andBiochemistry vol 75 no 8 pp 1435ndash1439 2011

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[69] O V Zillich U Schweiggert-Weisz P Eisner and M KerscherldquoPolyphenols as active ingredients for cosmetic productsrdquoInternational Journal of Cosmetic Science vol 37 no 5 pp 455ndash464 2015

[70] H Palafox-Carlos J F Ayala-Zavala and G A Gonzalez-Aguilar ldquoThe role of dietary fiber in the bioaccessibility andbioavailability of fruit and vegetable antioxidantsrdquo Journal ofFood Science vol 76 no 1 pp R6ndashR15 2011

[71] A Ratz-Łyko J Arct SMajewski andK Pytkowska ldquoInfluenceof polyphenols on the physiological processes in the skinrdquoPhytotherapy Research vol 29 no 4 pp 509ndash517 2015

[72] J Sun Y-F Chu X Wu and R H Liu ldquoAntioxidant andantiproliferative activities of common fruitsrdquo Journal of Agricul-tural and Food Chemistry vol 50 no 25 pp 7449ndash7454 2002

[73] E Sentandreu M Cerdan-Calero J M Halket and J LNavarro ldquoRapid screening of low-molecular-weight phenolsfrom persimmon (Diospyros kaki) pulp using liquid chroma-tographyUVndashvisibleelectrospray mass spectrometry analysisrdquoJournal of the Science of Food and Agriculture vol 95 pp 1648ndash1654 2015

[74] L Bravo ldquoPolyphenols chemistry dietary sources metabolismand nutritional significancerdquo Nutrition Reviews vol 56 no 11pp 317ndash333 1998

[75] T Akagi Y Suzuki A Ikegami et al ldquoCondensed tannin com-position analysis in persimmon (Diospyros kakiThunb) fruit byacid catalysis in the presence of excess phloroglucinolrdquo Journalof the Japanese Society for Horticultural Science vol 79 no 3 pp275ndash281 2010

[76] C Li R Leverence J D Trombley et al ldquoHighmolecularweightpersimmon (Diospyros kaki L) proanthocyanidin a highlygalloylated a-linked tannin with an unusual flavonol terminalunitmyricetinrdquo Journal of Agricultural and FoodChemistry vol58 no 16 pp 9033ndash9042 2010

[77] C A Rice-Evans N J Miller and G Paganga ldquoStructure-antioxidant activity relationships of flavonoids and phenolicacidsrdquo Free Radical Biology andMedicine vol 20 no 7 pp 933ndash956 1996

[78] R Tsao ldquoChemistry and biochemistry of dietary polyphenolsrdquoNutrients vol 2 no 12 pp 1231ndash1246 2010

[79] S Uchida H Ohta R Edamatsu M Hiromatsu A Mori andG I Nomaka ldquoPersimmon tannin prolongs life span of stroke-prone spontaneously hypertensive rats (SHRSP) by acting as afree-radical scavengerrdquo in New Horizons in Preventing Cardio-vascular Diseases Y Yamori and T Strasser Eds pp 15ndash17Academic Press Amsterdam The Netherlands Elsevier NewYork NY USA 1989

[80] S Uchida H Ohta M Niwa et al ldquoProlongation of life spanof stroke-prone spontaneously hypertensive rats (SHRSP)ingesting persimmon tanninrdquo Chemical and PharmaceuticalBulletin vol 38 no 4 pp 1049ndash1052 1990

[81] S Gorinstein G W Kulasek E Bartnikowska et al ldquoThe influ-ence of persimmon peel and persimmon pulp on the lipidmeta-bolism and antioxidant activity of rats fed cholesterolrdquo Journalof Nutritional Biochemistry vol 9 no 4 pp 223ndash227 1998

[82] K Matsumoto A Kadowaki N Ozaki et al ldquoBile acid-bind-ing ability of kaki-tannin from young fruits of persimmon (Dio-spyros kaki) in vitro and in vivordquo Phytotherapy Research vol 25no 4 pp 624ndash628 2011

[83] K Ueda R Kawabata T Irie Y Nakai Y Tohya and T Sak-aguchi ldquoInactivation of pathogenic viruses by plant-derivedtannins strong effects of extracts from persimmon (Diospyros

Journal of Chemistry 11

kaki) on a broad range of virusesrdquo PLoS ONE vol 8 no 1Article ID e55343 10 pages 2013

[84] H Suzuki M Konishi M Kimura T Mori M Suzuki and TIkemi ldquoInhibitory effects ofDiospyros kakiTHUNB Extracts indental caries in ratsrdquo Japanese Journal of Conservative Dentistryvol 50 no 2 pp 140ndash145 2007

[85] S Sakanaka Y Tachibana and Y Okada ldquoPreparation andantioxidant properties of extracts of Japanese persimmon leaftea (Kakinoha-cha)rdquo Food Chemistry vol 89 no 4 pp 569ndash5752005

[86] MHosny and J PN Rosazza ldquoNovel oxidations of (+)-catechinby horseradish peroxidase and laccaserdquo Journal of Agriculturaland Food Chemistry vol 50 no 20 pp 5539ndash5545 2002

[87] J-I Inokuchi H Okabe T Yamauchi and A NagamatsuldquoInhibitors of angiotensin converting enzyme in crude drugsrdquoChemical and Pharmaceutical Bulletin vol 32 no 9 pp 3615ndash3619 1984

[88] Y Tian B Zou L Yang et al ldquoHigh molecular weight per-simmon tannin ameliorates cognition deficits and attenuatesoxidative damage in senescent mice induced by d-galactoserdquoFood andChemical Toxicology vol 49 no 8 pp 1728ndash1736 2011

[89] Y Achiwa H Hibasami H Katsuzaki K Imai and T KomiyaldquoInhibitory effects of persimmon (Diospyros kaki) extract andrelated polyphenol compounds on growth of human lymphoidleukemia cellsrdquo Bioscience Biotechnology and Biochemistry vol61 no 7 pp 1099ndash1101 1997

[90] J Gross Carotenoids vol 123 Academic Press New York NYUSA 1987

[91] B De Ancos E Gonzalez and M P Cano ldquoEffect of high-pressure treatment on the carotenoid composition and theradical scavenging activity of persimmon fruit pureesrdquo Journalof Agricultural and Food Chemistry vol 48 no 8 pp 3542ndash3548 2000

[92] T Matsuo and S Ito ldquoThe chemical structure of Kaki-tanninfrom immature fruit of the persimmon (Diospyros kaki L)rdquoAgricultural and Biological Chemistry vol 42 no 9 pp 1637ndash1643 1978

[93] S Gorinstein M Zemser M Weisz et al ldquoFluorometric anal-ysis of phenolics in persimmonsrdquo Bioscience Biotechnology andBiochemistry vol 58 no 6 pp 1087ndash1092 1994

[94] S O Lee H J LeeMH Yu H G Im and I S Lee ldquoTotal poly-phenol contents and antioxidant activities of methanol extractsfrom vegetables produced in Ullung Islandrdquo Korean Journal ofFood Science and Technology vol 37 no 2 pp 233ndash240 2005

[95] U V Mallavadhani A K Panda and Y R Rao ldquoPharmacologyand chemotaxonomy of Diospyrosrdquo Phytochemistry vol 49 no4 pp 901ndash951 1998

[96] G Block B Patterson and A Subar ldquoFruit vegetables andcancer prevention a review of the epidemiological evidencerdquoNutrition and Cancer vol 18 no 1 pp 1ndash29 1992

[97] G van Poppel ldquoCarotenoids and cancer an updatewith empha-sis on human intervention studiesrdquo European Journal of Cancervol 29 no 9 pp 1335ndash1344 1993

[98] E Giovannucci A Ascherio E B Rimm M J Stampfer G AColditz and W C Willett ldquoIntake of carotenoids and retino inrelation to risk of prostate cancerrdquo Journal of theNational CancerInstitute vol 87 no 23 pp 1767ndash1776 1995

[99] T Johns R L A Mahunnah P Sanaya L Chapman and TTicktin ldquoSaponins and phenolic content in plant dietary addi-tives of a traditional subsistence community the Batemi ofNgorongoro District Tanzaniardquo Journal of Ethnopharmacologyvol 66 no 1 pp 1ndash10 1999

[100] Y Zhang X Lu Y Zhang L Qin and J Zhang ldquoSulfatedmodification and immunomodulatory activity of water-solublepolysaccharides derived from fresh Chinese persimmon fruitrdquoInternational Journal of Biological Macromolecules vol 46 no1 pp 67ndash71 2010

[101] Y-J Moon and Y-S Cha ldquoEffects of persimmon-vinegar onlipid metabolism and alcohol clearance in chronic alcohol-fedratsrdquo Journal of Medicinal Food vol 11 no 1 pp 38ndash45 2008

[102] H S Ahn T I Jeon J Y Lee S G Hwang Y Lim and D KPark ldquoAntioxidative activity of persimmon and grape seedextract in vitro and in vivordquo Nutrition Research vol 22 no 11pp 1265ndash1273 2002

[103] H Itamurah N Murakami and H Nagamatsu ldquoProperty ofkaki-tannin as a functional composition in persimmon fruitflesh and leaves and its solubility in artificial stomach liquidrdquoin Proceedings of the 27th International Horticultural Congressamp Exhibition (IHC rsquo06) vol 8 pp 265ndash267 August 2006

[104] K A Steinmetz and J D Potter ldquoVegetables fruit and cancerprevention a reviewrdquo Journal of the American Dietetic Associa-tion vol 96 no 10 pp 1027ndash1039 1996

[105] A N Nagappa P A Thakurdesai N V Rao and J SinghldquoAntidiabetic activity ofTerminalia catappa Linn fruitsrdquo Journalof Ethnopharmacology vol 88 no 1 pp 45ndash50 2003

[106] K Datta S Sinha and P Chattopadhyay ldquoReactive oxygenspecies in health and diseaserdquoNationalMedical Journal of Indiavol 13 no 6 pp 304ndash310 2000

[107] R R Holman and R C Turner ldquoOral agents and insulin in thetreatment of NIDDMrdquo in Textbook of Diabetes J Williams Edpp 407ndash469 Blackwell Press Oxford UK 1991

[108] F Giacco and M Brownlee ldquoOxidative stress and diabeticcomplicationsrdquo Circulation Research vol 107 no 9 pp 1058ndash1070 2010

[109] B K Rao M M Kesavulu R Giri and C A Rao ldquoAntidiabeticand hypolipidemic effects ofMomordicacymbalariaHook fruitpowder in alloxan-diabetic ratsrdquo Journal of Ethnopharmacologyvol 67 no 1 pp 103ndash109 1999

[110] J K Grover V Vats V Rathi and S S Dawar ldquoTraditionalIndian anti-diabetic plants attenuate progression of renal dam-age in streptozotocin induced diabetic micerdquo Journal of Ethno-pharmacology vol 76 no 3 pp 233ndash238 2001

[111] R K Gupta A N Kesari P S Murthy R Chandra V Tandonand GWatal ldquoHypoglycemic and antidiabetic effect of ethano-lic extract of leaves of Annona squamosa L in experimentalanimalsrdquo Journal of Ethnopharmacology vol 99 no 1 pp 75ndash81 2005

[112] S Gupta N Ahmad A-L Nieminen andHMukhtar ldquoGrowthinhibition cell-cycle dysregulation and induction of apopto-sis by green tea constituent (-)-epigallocatechin-3-gallate inandrogen-sensitive and androgen-insensitive human prostatecarcinoma cellsrdquoToxicology andApplied Pharmacology vol 164no 1 pp 82ndash90 2000

[113] T Yokozawa Y A Kim H Y Kim Y A Lee and G-I NonakaldquoProtective effect of persimmon peel polyphenol against highglucose-induced oxidative stress in LLC-PK1 cellsrdquo Food andChemical Toxicology vol 45 no 10 pp 1979ndash1987 2007

12 Journal of Chemistry

[114] M S Brewer ldquoNatural antioxidants sources compoundsmechanisms of action and potential applicationsrdquo Comprehen-sive Reviews in Food Science and Food Safety vol 10 no 4 pp221ndash247 2011

[115] K Kawakami H Nishida N Tatewaki Y Nakajima T Konishiand M Hirayama ldquoPersimmon leaf extract inhibits the ATMactivity during DNA damage response induced by Doxorubicinin A549 lung adenocarcinoma cellsrdquo Bioscience Biotechnologyand Biochemistry vol 75 no 4 pp 650ndash655 2011

[116] D Steinberg S Parthasarathy T E Carew J C Khoo and JL Witztum ldquoBeyond cholesterol modifications of low-densitylipoprotein that increase its atherogenicityrdquo The New EnglandJournal of Medicine vol 320 no 14 pp 915ndash924 1989

[117] P M Kris-Etherton and C L Keen ldquoEvidence that the anti-oxidant flavonoids in tea and cocoa are beneficial for cardiovas-cular healthrdquo Current Opinion in Lipidology vol 13 no 1 pp41ndash49 2002

[118] C Manach A Mazur and A Scalbert ldquoPolyphenols and pre-vention of cardiovascular diseasesrdquo Current Opinion in Lipidol-ogy vol 16 no 1 pp 77ndash84 2005

[119] J W Anderson B M Smith and N J Gustafson ldquoHealthbenefits and practical aspects of high-fiber dietsrdquo AmericanJournal of Clinical Nutrition vol 59 no 5 pp 1242ndash1247 1994

[120] D Kromhout A Menotti H Kesteloot and S Sans ldquoPreven-tion of coronary heart disease by diet and lifestyle evidencefrom prospective cross-cultural cohort and intervention stud-iesrdquo Circulation vol 105 no 7 pp 893ndash898 2002

[121] E B Rimm M J Stampfer A Ascherio E Giovannucci G AColditz andWCWillett ldquoVitamin E consumption and the riskof coronary heart disease in menrdquo The New England Journal ofMedicine vol 328 no 20 pp 1450ndash1456 1993

[122] L Dauchet J Ferrieres D Arveiler et al ldquoFrequency of fruitand vegetable consumption and coronary heart disease inFrance and Northern Ireland the prime studyrdquo British Journalof Nutrition vol 92 no 6 pp 963ndash972 2004

[123] S Gorinstein GW Kulasek E Bartnikowska et al ldquoThe effectsof diets supplementedwith either whole persimmon or phenol-free persimmon on rats fed cholesterolrdquo Food Chemistry vol70 no 3 pp 303ndash308 2000

[124] M G L Hertog E J M Feskens P C H HollmanM B Katanand D Kromhout ldquoDietary antioxidant flavonoids and risk ofcoronary heart disease the Zutphen Elderly studyrdquoThe Lancetvol 342 no 8878 pp 1007ndash1011 1993

[125] H Seo B D Jeon andR Sungpil ldquoPersimmon vinegar ripeningwith the mountain-cultivated ginseng ingestion reduces bloodlipids and lowers inflammatory cytokines in obese adolescentsrdquoJournal of Exercise Nutrition and Biochemistry vol 19 no 1 pp1ndash10 2015

[126] R H Liu ldquoPotential synergy of phytochemicals in cancerprevention mechanism of actionrdquo Journal of Nutrition vol 134no 12 supplement pp 3479Sndash3485S 2004

[127] S T Mayne ldquoAntioxidant nutrients and chronic disease use ofbiomarkers of exposure and oxidative stress status in epidemi-ologic researchrdquo Journal of Nutrition vol 133 no 3 pp 933sndash940s 2003

[128] H Tapiero D M Townsend and K D Tew ldquoThe role of caro-tenoids in the prevention of human pathologiesrdquo Biomedicineand Pharmacotherapy vol 58 no 2 pp 100ndash110 2004

[129] J Tao and S L Zhang ldquoMetabolismof carotenoid and its regula-tion in garden croprdquo Journal of Zhejiang University (Agricultureamp Life Sciences) vol 29 pp 585ndash590 2003

[130] W Miki ldquoBiological functions and activities of animal caro-tenoidsrdquo Pure and Applied Chemistry vol 63 no 1 pp 141ndash1461991

[131] H Fujiki ldquoGreen tea health benefits as cancer preventive forhumansrdquo Chemical Record vol 5 no 3 pp 119ndash132 2005

[132] A P George and S Redpath ldquoHealth and medicinal benefits ofpersimmon fruit a reviewrdquo Advances in Horticultural Sciencevol 22 no 4 pp 244ndash249 2008

[133] T Hussain S Gupta V M Adhami and H Mukhtar ldquoGreentea constituent epigallocatechin-3-gallate selectively inhibitsCOX-2 without affecting COX-1 expression in human prostatecarcinoma cellsrdquo International Journal of Cancer vol 113 no 4pp 660ndash669 2005

[134] Y-C Wang and U Bachrach ldquoThe specific anti-cancer activityof green tea (minus)-epigallocatechin-3-gallate (EGCG)rdquo AminoAcids vol 22 no 2 pp 131ndash143 2002

[135] O Takayuki ldquoPersimmons your healthy autumn treatsrdquoAsahikawa Information vol 108 pp 1ndash2 2005

[136] T Fukuda and H Shibata ldquoPersimmon calyx extracts as anti-convulsants and to alleviate the side effects of barbituric acidcompoundsrdquo Patent Japanease Kokai Tokkyo Koho vol 6 pp649ndash653 1994

[137] T Matsuno ldquoXanthophylls as precursors of retinoidsrdquo Pure andApplied Chemistry vol 63 no 1 pp 81ndash88 1991

[138] N Gato A Kadowaki N Hashimoto S-I Yokoyama and KMatsumoto ldquoPersimmon fruit tannin-rich fiber reduces choles-terol levels in humansrdquoAnnals of Nutrition andMetabolism vol62 no 1 pp 1ndash6 2013

[139] A Nagao ldquoAbsorption and function of dietary carotenoidsrdquoForum of Nutrition vol 61 pp 55ndash63 2009

[140] PD Fraser andPM Bramley ldquoThebiosynthesis andnutritionaluses of carotenoidsrdquo Progress in Lipid Research vol 43 no 3 pp228ndash265 2004

[141] D Fusco G Colloca M R Lo Monaco and M Cesari ldquoEffectsof antioxidant supplementation on the aging processrdquo ClinicalInterventions in Aging vol 2 no 3 pp 377ndash387 2007

[142] JM Seddon U Ajan and R D Sperduto ldquoDietary carotenoidsvitamins A C and E and advance age-related macular degen-eration Eye Disease Case Study Grouprdquo Journal of AmericanMedical Association vol 272 no 18 pp 1413ndash1420 1992

[143] B-J An J-H Kwak J-M Park et al ldquoInhibition of enzymeactivities and the antiwrinkle effect of polyphenol isolated fromthe persimmon leaf (Diospyros kaki folium) on human skinrdquoDermatologic Surgery vol 31 no 7 pp 848ndash854 2005

[144] H Arakawa M Takasaki N Tajima H Fukamachi and TIgarashi ldquoAntibacterial activities of persimmon extracts relatewith their hydrogen peroxide concentrationrdquo Biological andPharmaceutical Bulletin vol 37 no 7 pp 1119ndash1123 2014

[145] S D Ladas D Kamberoglou G Karamanolis J Vlachogian-nakos and I Zouboulis-Vafiadis ldquoSystematic review Coca-Cola can effectively dissolve gastric phytobezoars as a first-linetreatmentrdquo Alimentary Pharmacology and Therapeutics vol 37no 2 pp 169ndash173 2013

[146] T J Cifuentes C R Robles P P Parrilla et al ldquoPolyphenols andhealth what compounds are involvedrdquo Nutrition Metabolismand Cardiovascular Diseases vol 20 no 1 pp 1ndash6 2010

[147] J Gaya L Barranco A Llompart J Reyes and A ObradorldquoPersimmon bezoars a successful combined therapyrdquoGastroin-testinal Endoscopy vol 55 no 4 pp 581ndash583 2002

[148] P G Hayes and O D Rotstein ldquoGastrointestinal phytobezoarspresentation and managementrdquo Canadian Journal of Surgeryvol 29 no 6 pp 419ndash420 1986

Journal of Chemistry 13

[149] MM Krausz E ZMoriel A Ayalon D Pode and A L DurstldquoSurgical aspects of gastrointestinal persimmon phytobezoartreatmentrdquoThe American Journal of Surgery vol 152 no 5 pp526ndash530 1986

[150] P Walker-Renard ldquoUpdate on the medicinal management ofphytobezoarsrdquo The American Journal of Gastroenterology vol88 no 10 pp 1663ndash1666 1993

[151] S S Ha H S LeeM K Jung et al ldquoAcute intestinal obstructioncaused by a persimmon phytobezoar after dissolution therapywith Coca-Colardquo The Korean Journal of Internal Medicine vol22 no 4 pp 300ndash303 2007

[152] J Han S Kang R Choue et al ldquoFree radical scavenging effectofDiospyros kaki Laminaria japonica andUndaria pinnatifidardquoFitoterapia vol 73 no 7-8 pp 710ndash712 2002

Submit your manuscripts athttpwwwhindawicom

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Inorganic ChemistryInternational Journal of

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CatalystsJournal of

Page 6: Review Article Chemistry and Functionality of Bioactive ...downloads.hindawi.com/journals/jchem/2016/3424025.pdf · Review Article Chemistry and Functionality of Bioactive Compounds

6 Journal of Chemistry

Table 2 Various bioactive compounds present in persimmon and their functional properties

Source Health benefits ReferenceExtracted polyphenol119901-Coumaric Prevention of oxidative stress related diseases including diabetes [86]Tannins Scavenging action against active oxygen free radicals [82 87 88]

Tannin Assists the neuronal degeneration and karyopyknosis in cells reduction ofthickness of skin epidermis [89]

Flavonoids Scavenging action against active oxygen free radicals [82 87 88]Persimmon fruit

Whole fruit

Possesses antitumor effects due to betulinic acid [47 90]Blood pressure-lowering and diuretic effects also effective for coughs treatment [91]Has antioxidative potentials due to compounds like vitamin A beta-carotenelycopene lutein zeaxanthin and cryptoxanthin [92]

Exhibits hypolipidemic and antioxidant properties [50 82]Contains nutritional antioxidant vitamins polyphenols and dietary fiber [93 94]Reduction of patches of pigmentation on skin [95]Has ability to dilate the blood vessels near the surface of the skin thereby allowingmore blood to flow through the skin where it can be cooled by the air (antifebrile) [96]

Reduction of degenerative disease in human beings [91 97ndash99]Fruit peel powder Pharmacological potential such as antioxidant and hypocholesterolemic [51 95 100]Water-solublepolysaccharides extractedfrom persimmon fruits

Have ability to alter or regulate immune functions (immunomodulatory activity) [85]

Persimmon vinegar Has antitumor and antioxidative effects and also prevents metabolic disorderinduced by chronic alcohol administration [101]

Plant and leaf extracts

Persimmon leaf tea Prevents hardening of the arteries which ultimately lowers the blood pressure [95]Good source of natural antioxidants [102]

Persimmon plant extracts Contain antitumor and multidrug resistance-reversing agentsStop oxidative damage of DNA [47]

Persimmon calyx extracts Anticonvulsants [103]Persimmon plantsupplemented to a diet Hypocholesterolemic and antioxidative effects [82]

Persimmon seeds Contain omega 6 fatty acids like palmitic acid oleic acid and linoleic acid [63]Radical-scavenging activity [104]

Among fruits persimmon is comprised of a large numberof biologically active polyphenols like tannins and flavonoidshaving good antioxidant potential These polyphenols pre-vent the diabetes resulting from oxidative stress [86] sincethese work as antioxidants preventing the peroxidation oflipids by the donation of a hydrogen atom from hydroxylgroup attached to their chemical structure rapidly and formperoxyl radical (ROO) that ultimately leads to the formationof alkyl (aryl) hydroperoxide (ROOH) as shown in thefollowing reaction

ROOminus + PPH 997888rarr ROOH + PPminus (1)

The phenolic antioxidant (PPH) itself changes intopolyphenol phenoxyl radical (PP) which becomes stable afterdonating a hydrogen atom by conversion into quinines andit hinders the initiation of new chain reaction by reactingwith another radical inwhich another phenoxyl radical is alsoincluded [114 115]

Gorinstein et al [49] reported that a 2-week intake ofpersimmon peel supplemented diet considerably reducesfood intake blood glucose total cholesterol and plasmatriglycerides level in diabeticsThe researchers concluded thatpersimmon peel rich in high level of antioxidant and dietaryfiber with antidiabetic properties may be characterized asa possible nutritional supplement for improving diabeticcomplications and hyperglycemia

In fresh persimmon leaves most of the polyphenols arefound to be water soluble The chief components in persim-mon leaf tea are unique proanthocyanidin oligomers andoral administration of this tea along with starch resulted in adose-dependent decline in the blood glucose level in Wistarrats [116]

72 Atherosclerosis Inflammation and high levels of oxida-tive stress are a major initiator of cardiovascular diseaseslike atherosclerosis that ultimately leads to coronary artery

Journal of Chemistry 7

disease (CAD) In such condition the oxidative stress is char-acterized by the accumulation of metabolites (from the oxi-dation of proteins and lipids) and macrophages Accordingto the hypothesis of oxidative modification the early eventwhich initiates the development of atherogenesis (develop-ment of atheromatous plaques) is the oxidative breakdownof low-density lipoproteins Reactive oxygen species in thevessel wall have been considered to be one of the mostimportant causes of vascular dysfunction [117]

Dietary components having antioxidant properties as thepolyphenols are receiving a lot of attention because of theirability to reduce cardiovascular diseases [118 119] When dietrich in fiber is largely consumed it results in preventionand treatment of diverticular and coronary heart diseases[120] Coronary atherosclerosis especially is inhibited bypreventing oxidation of low-density lipoprotein (LDL) and bynutritional antioxidants like phenolics [121] and vitamins AC and E [122]

Hence many reports have shown that if intake of veg-etables and fruits is increased in diet then chances of coro-nary heart diseases could greatly be reduced [123] Accord-ing to Hertog et al [124] if 100 g of persimmon is con-sumed regularly then it will be sufficient to inhibit occlu-sion of arteries In young fruits of persimmon (Diospyroskaki) tannin is found to have the ability of bonding bile acid[83]

It has been established that addition of persimmon inthe diet hinders the increase in plasma lipid level and henceworks as antiatherosclerosis [80 124] which reduces thechances of mortality by the action of polyphenols [125]Matsumoto et al [82] also reported that the persimmon peelsupplemented diet shows hypocholesterolemic and antiox-idative effect

Total dietary fibers including soluble and insoluble totalphenolics including epicatechin gallic and p-coumaric acidsand concentrations of minerals like Na K Mg Ca Feand Mn are high in peel pulp and whole persimmon fruitcompared to apple [50] Hence persimmon must be givenpreference over apples and some other fruits in selecting anantiatherosclerotic diet Liu [126] reported decline in bloodtriglyceride and total cholesterol contents after intake ofpersimmon vinegar (PV) for 6 weeks

73 Cancer In recent years persimmon has been thefocus of attention for potential medicinal applications forprevention of cancer [47] Carotenoids are naturersquos mostwidespread pigments and have also received substantialattention because of both their provitamin and antioxidantroles [127] Carotenoids possess antioxidant properties thathave been associatedwith cellular protection [128] regulationof cell growth differentiation and apoptosis [129]

Not only are the carotenoid contents responsible forthe superficial appearance (color) and nutritional quality offruit [130] but also they provide potential health benefitsand disease prevention by quenching singlet oxygen andscavenging free radicals [131] Chemoprotective effects ofpersimmon against various forms of cancer are due to thecarotenoid contents [132 133] Persimmon was shown tobe effective in the treatment of prostate and breast cancers

[134] oral carcinoma cells [47] human lymphoid leukemiacells [135] and precancerous colon polyps in women [136]The bioactive compounds in persimmon may also affectmultidrug resistant (MDR) inhibiting activity It enhances theaccumulation of cancer cells due to the reduced activity ofefflux pumps MDR inhibitors from persimmon may helpto treat noncurable cancer because of the modulating effects[47] The calyx (persimmon) extracts act as anticonvulsantsand may alleviate the side effects of barbituric acid com-pounds [103]

8 Other Health Promoting Properties

Dried persimmon snacks were found to be effective inreducing the concentration of alcohol in the blood [55]Similarly Matsuno [137] observed that kaki-tannin foundin persimmon fruit flesh and leaves was soluble in artifi-cial stomach liquid and reduced blood alcohol (40) andacetaldehyde contents (30) Dietary intake of persimmontannin was found to prevent hypercholesterolemia in someanimal models and humans [138]

Some carotenoids present in persimmon are precur-sors of vitamin A [139] and also have immunoregulatory[140] and antiaging effects [141] Carotenoids are inverselylinked with inflammation atherosclerosis cardiovasculardiseases sarcopenia and mortality Carotenoid supplemen-tation improves the antioxidant status and reduces lipidperoxidation

Carotenoids like 120573-carotene 120572-carotene 120573-cryptoxan-thin lycopene and lutein (Figure 2) have been found to beassociated with inflammation and mortality risks [142] Inaddition lutein (carotenoids) present in persimmon peel canhelp protect eye vision [143]

9 Persimmon Leaves and Health

Persimmon leaves and extracts are being used as a greentea oriental medicines deodorants antiallergic substratesand cosmetics (especially for dermatitis) as they prevent skinproblems and have an antiwrinkle effect [68 143] and skinwhitening effect [72] The leaves are brewed into a beverageto release their antioxidant activity and antitumor effects andto inhibit angiotensin converting enzymes as well as alphaamylase [66] The leaves of persimmon possess antithrom-botic activity Arakawa et al [144] demonstrated that a 10000D anticoagulant fraction has been purified from the leavesthat inhibited thrombin-catalyzed fibrin formation with acompetitive inhibition pattern Based on their antimicrobialproperties persimmon leaf-based products have been incor-porated into athletersquos foot socks and soaps and persimmonleaves have been used as a sushi ingredient [145]

10 Unripen Persimmons and Health Issues

Bezoars are thick hard masses formed in gastrointestinaltract usually the stomach [146] Patients who have undergonestomach surgery and have delayed gastric emptying areoften more prone to the development of bezoars [147]Phytobezoars are the most common types of bezoars and

8 Journal of Chemistry

these are composed of skins seeds and vegetative matterincluding lignin cellulose hemicelluloses tannins and othernondigestible matter from fruits and vegetables ingestedDiospyrobezoars are a type of phytobezoars related to theconsumption of persimmon fruit and are common world-wide These are more difficult to treat because of their hardconsistency [146 148 149] Most bezoars in animals arecaused by hairs

When unripe astringent persimmon having a high levelof tannin is ingested a coagulum is formed in the stomachdue to the contact of tannin and shibuol with hydrochloricacid that accumulates cellulose hemicellulose and pro-tein [150] Phytobezoars may require surgical removal orendoscopic treatment as they are usually resistant to drugtreatment [151] Han et al [152] suggested a nonsurgicalapproach for cases of persimmon phytobezoar small intesti-nal obstruction with its partial dissolution of a bezoar byperforming oral and injected Coca-Cola therapy

11 Conclusion

Bioactive compounds particularly phenolics (ferulic p-coumaric and gallic acids) and carotenoids (120573-cryptoxan-thin lycopene 120573-carotene and lutein) are of major interestsin persimmon fruitThese valued bioactive components havestrong antioxidant potential which relates to the variety stageof maturity and fruit parts These functional compoundscan play a significant role in preventing and curing variousailments like diabetes hypercholesterolemia and cancerHence the known impact of natural bioactive compounds toimprove human health has introduced a substantial area ofresearch resulting in extensive advances in biochemical andnutritional sciences

Conflict of Interests

The authors declare that there is no conflict of interestsregarding the publication of this paper

References

[1] S Lordan R P Ross and C Stanton ldquoMarine bioactives asfunctional food ingredients potential to reduce the incidenceof chronic diseasesrdquoMarine Drugs vol 9 no 6 pp 1056ndash11002011

[2] S Yaqub U Farooq T Kausar Z Hayat M Jaskani and S MUllah ldquoHypocholestrolemic effect of persimmon peel powderin rabbitsrdquo Journal of Science International vol 25 no 3 pp605ndash609 2013

[3] M S Butt M T Sultan M Aziz et al ldquoPersimmon (Piospyroskaki) fruit hidden phytochemicals and health claimsrdquo EXCLIJournal vol 14 pp 542ndash561 2015

[4] A H A Hadi M E Duru and A B Martin-Diana ldquoBioactivenatural productsrdquo Journal of Chemistry vol 2013 Article ID208507 1 page 2013

[5] M R Segura Campos J Ruiz Ruiz L Chel-Guerrero and DBetancur Ancona ldquoCoccoloba uvifera (L)(Polygonaceae) fruitphytochemical screening and potential antioxidant activityrdquoJournal of Chemistry vol 2015 Article ID 534954 9 pages 2015

[6] S Karaman O S Toker F Yuksel M Cam A Kayacier andM Dogan ldquoPhysicochemical bioactive and sensory propertiesof persimmon-based ice cream technique for order prefer-ence by similarity to ideal solution to determine optimum con-centrationrdquo Journal of Dairy Science vol 97 no 1 pp 97ndash1102014

[7] M C Caruso F Galgano M Pecora R Tolve M Verrastroand F Favati ldquoImprovement of analytical methods for thedetermination of polyphenolic bioactive compounds in berryfruitsrdquo Journal of Chemistry vol 2015 Article ID 384051 6pages 2015

[8] R H Liu ldquoHealth benefits of fruit and vegetables are fromadditive and synergistic combinations of phytochemicalsrdquo TheAmerican Journal of Clinical Nutrition vol 78 no 3 pp 517Sndash520S 2003

[9] L Dauchet P Amouyel S Hercberg and J Dallongeville ldquoFruitand vegetable consumption and risk of coronary heart diseasea meta-analysis of cohort studiesrdquo Journal of Nutrition vol 136no 10 pp 2588ndash2593 2006

[10] A Denny and J Buttriss ldquoPlant foods and health focuson plant bioactivesrdquo EU 6th Framework Food Quality andSafety Thematic Priority Contract FOOD-CT-2005-513944European Food Information Resource (EuroFIR) Consortium2007

[11] S M K Rates ldquoPlants as source of drugsrdquo Toxicon vol 39 no5 pp 603ndash613 2001

[12] D Zhao C Zhou Y Sheng G Liang and J Tao ldquoMolecularcloning and expression of phytoene synthase lycopene beta-cyclase and beta-carotene hydroxylase genes in persimmon(Diospyros kaki L) fruitsrdquo PlantMolecular Biology Reporter vol29 no 2 pp 345ndash351 2011

[13] K Suzuki S Tsubaki M Fujita N Koyama M Takahashiand K Takazawa ldquoEffects of safflower seed extract on arterialstiffnessrdquo Vascular Health and Risk Management vol 6 no 1pp 1007ndash1014 2010

[14] M S Butt and M T Sultan ldquoGreen tea naturersquos defense againstmalignanciesrdquo Critical Reviews in Food Science and Nutritionvol 49 no 5 pp 463ndash473 2009

[15] I Raskin D M Ribnicky S Komarnytsky et al ldquoPlants andhuman health in the twenty-first centuryrdquo Trends in Biotechnol-ogy vol 20 no 12 pp 522ndash531 2002

[16] S Parab R Kulkarni and U Thatte ldquoHeavy metals in herbalmedicinesrdquo Indian Journal of Gastroenterology vol 22 no 3 pp111ndash112 2003

[17] K L Miller R S Liebowitz and L K Newby ldquoComplementaryand alternative medicine in cardiovascular disease a review ofbiologically based approachesrdquoAmericanHeart Journal vol 147no 3 pp 401ndash411 2004

[18] D L Guo and Z R Luo ldquoGenetic relationships of the Japanesepersimmon Diospyros kaki (Ebenaceae) and related speciesrevealed by SSR analysisrdquo Genetics and Molecular Research vol10 no 2 pp 1060ndash1068 2011

[19] M J Li D Liang F Pu F W Ma C M Hou and T LuldquoAscorbate levels and the activity of key enzymes in ascorbatebiosynthesis and recycling in the leaves of 22 Chinese persim-mon cultivarsrdquo Scientia Horticulturae vol 120 no 2 pp 250ndash256 2009

[20] Z Luo ldquoEffect of 1-methylcyclopropene on ripening of posthar-vest persimmon (Diospyros kaki L) fruitrdquo LWTmdashFood Scienceand Technology vol 40 no 2 pp 285ndash291 2007

Journal of Chemistry 9

[21] A T Oz ldquoCombined effects of 1-methyl cyclopropene (1-MCP)andmodified atmosphere packaging (MAP) on different ripen-ing stages of persimmon fruit during storagerdquo African Journalof Biotechnology vol 10 no 5 pp 807ndash814 2011

[22] M S Akter M Ahmed and J B Eun ldquoDietary fibre compo-nents antioxidant activities and hydration properties of ripepersimmon (Diospyros kaki L cv Daebong) peel powders asaffected by different washing treatmentsrdquo International Journalof Food Science and Technology vol 45 no 7 pp 1464ndash14712010

[23] K Yonemori A Sugiura andM Yamada ldquoPersimmon geneticsand breedingrdquo Plant Breeding Reviews vol 19 pp 191ndash225 2000

[24] P Thomas and T S Chen ldquoQuantitative analyses of majorcarotenoid fatty acid esters in fruits by liquid chromatographypersimmon and papayardquo Journal of Food Science vol 53 no 6pp 1720ndash1722 1988

[25] T Nakagawa A Nakatsuka K Yano et al ldquoExpressed sequencetags from persimmon at different developmental stagesrdquo PlantCell Reports vol 27 no 5 pp 931ndash938 2008

[26] R Veberic J Jurhar M Mikulic-Petkovsek F Stampar andV Schmitzer ldquoComparative study of primary and secondarymetabolites in 11 cultivars of persimmon fruit (Diospyros kakiL)rdquo Food Chemistry vol 119 no 2 pp 477ndash483 2010

[27] A Ikegami S Eguchi A Kitajima K Inoue and K YonemorildquoIdentification of genes involved in proanthocyanidin biosyn-thesis of persimmon (Diospyros kaki) fruitrdquo Plant Science vol172 no 5 pp 1037ndash1047 2007

[28] A Sattar N Bibi and M A Chaudry ldquoPhenolic compoundsin persimmon during maturation and on-tree ripeningrdquo Food Nahrung vol 36 no 5 pp 466ndash472 1992

[29] Y-S Park S-T Jung S-G Kang et al ldquoDrying of persimmons(Diospyros kaki L) and the following changes in the studiedbioactive compounds and the total radical scavenging activi-tiesrdquo LWTmdashFood Science and Technology vol 39 no 7 pp 748ndash755 2006

[30] A Ikegami T Akagi D Potter et al ldquoMolecular identifica-tion of 1-Cys peroxiredoxin and anthocyanidinflavonol 3-O-galactosyltransferase from proanthocyanidin-rich young fruitsof persimmon (Diospyros kakiThunb)rdquo Planta vol 230 no 4pp 841ndash855 2009

[31] T Radha and L Mathew Fruit Crops Horticulture ScienceSeries Jai Baharat Press 2007

[32] H Yakushiji ldquoRecent persimmon research in Japanrdquo JapaneseJournal of Plant Science vol 1 pp 42ndash62 2007

[33] X N Chen J F Fan X Yue X R Wu and L T Li ldquoRadicalscavenging activity and phenolic compounds in persimmon(Diospyros kaki L cv Mopan)rdquo Journal of Food Science vol 73no 1 pp C24ndashC28 2008

[34] H R Wang P Leng and C S Wang ldquoEffect of absorbentson storage quality of the Mopan persimmonrdquo Journal ShanxiAgriculture and Science vol 33 no 1 pp 59ndash61 2005

[35] X H Guo S Z Fang J Wang X X Guo L Q Xu and L YuanldquoStudy on the infection of the Mopan persimmon quality bycarbon dioxiderdquo Food Research Developments vol 27 pp 156ndash159 2006

[36] S Li P Zhang J K Li L Wang and Y F Huang ldquoEffect of1-methylcyclopropene for the Mopan persimmon crispiness-keeping under ambient temperaturerdquo Storing Process vol 6 pp13ndash16 2006

[37] J L Vazquez-Gutierrez I Hernando and A Quiles ldquoChangesin tannin solubility and microstructure of high hydrostaticpressurendashtreated persimmon cubes during storage at 4∘CrdquoEuropean Food Research and Technology vol 237 no 1 pp 9ndash172013

[38] N Bibi A B Khattak and ZMehmood ldquoQuality improvementand shelf life extension of persimmon fruit (Diospyros kaki)rdquoJournal of Food Engineering vol 79 no 4 pp 1359ndash1363 2007

[39] S Kondo H Yoshikawa and R Katayama ldquoAntioxidant activityin astringent and non-astringent persimmonsrdquo Journal of Hor-ticultural Science and Biotechnology vol 79 no 3 pp 390ndash3942004

[40] X Wei F Liu Z Qiu Y Shao and Y He ldquoRipeness classifica-tion of astringent persimmon using hyperspectral imagingtechniquerdquo Food and Bioprocess Technology vol 7 no 5 pp1371ndash1380 2014

[41] K P Wright and A A Kader ldquoEffect of controlled-atmospherestorage on the quality and carotenoid content of sliced persim-mons and peachesrdquo Postharvest Biology and Technology vol 10no 1 pp 89ndash97 1997

[42] P Novillo A Salvador E Llorca I Hernando and C BesadaldquoEffect of CO

2deastringency treatment on flesh disorders

induced by mechanical damage in persimmon Biochemicaland microstructural studiesrdquo Food Chemistry vol 145 pp 454ndash463 2014

[43] C J Xu and S L Zhang ldquoCarotenoid biosynthesis and its regu-lation in plantsrdquo Plant Physiology and Communication vol 36pp 64ndash70 2000

[44] E Bellini G Giannelli and E Picardi ldquoPanoramica varietaledel Kaki nel mondo e orientamenti produttivi per lrsquoItaliardquoLrsquoinformatore Agrario vol 44 no 47 pp 47ndash88 2011

[45] USDA-Agriculture Research Service National AgriculturalLibrary Beltsville Md USA vol 44 pp 47ndash88 1998

[46] M Kawase N Motohashi K Satoh et al ldquoBiological activityof persimmon (Diospyros kaki) peel extractsrdquo PhytotherapyResearch vol 17 no 5 pp 495ndash500 2003

[47] W Bei W Peng Y Ma and A Xu ldquoFlavonoids from the leavesof Diospyros kaki reduce hydrogen peroxide-induced injury ofNG108-15 cellsrdquo Life Sciences vol 76 no 17 pp 1975ndash1988 2005

[48] S-O Lee S-K Chung and I-S Lee ldquoThe antidiabetic effect ofdietary persimmon (Diospyros kaki L cv sangjudungsi) peel instreptozotocin-induced daibetic ratsrdquo Journal of Food Sciencevol 71 no 3 pp S293ndashS298 2006

[49] S Gorinstein Z Zachwieja M Folta et al ldquoComparative con-tents of dietary fiber total phenolics and minerals in persim-mons and applesrdquo Journal of Agricultural and Food Chemistryvol 49 no 2 pp 952ndash957 2001

[50] H Leontowicz S Gorinstein A Lojek et al ldquoComparativecontent of some bioactive compounds in apples peaches andpears and their influence on lipids and antioxidant capacity inratsrdquo Journal of Nutritional Biochemistry vol 13 no 10 pp 603ndash610 2002

[51] Y A Lee E J Cho and T Yokozawa ldquoProtective effect of per-simmon (Diospyros kaki) peel proanthocyanidin against oxida-tive damage under H

2O2-induced cellular senescencerdquo Biolog-

ical and Pharmaceutical Bulletin vol 31 no 6 pp 1265ndash12692008

[52] A Subagio N Morita and S Sawada ldquoCarotenoids and theirfatty-acid esters in banana peelrdquo Journal of Nutritional Scienceand Vitaminology vol 42 no 6 pp 553ndash566 1996

10 Journal of Chemistry

[53] Y J Yang and S J Kim ldquoChanges in chlorophyll and carotenoidcontents during cold and CA storage and characterization ofthe carotenoids in the peel of lsquoFujirsquo apple fruitrdquo Journal of KoreanSociety and Horticultural Science vol 36 pp 500ndash505 1995

[54] Y C Kim J B Kim K J Cho I S Lee and S K ChungldquoCarotenoid content of Korean persimmon peel and theirchanges in storagerdquo Food Science and Biotechnology vol 11 no5 pp 477ndash479 2002

[55] J Tous and L Ferguson ldquoMediterranean fruitsrdquo in Progress inNew Crops J Janick Ed pp 416ndash430 ASHS Press ArlingtonVa USA 1996

[56] B YuanH L Xu and S P Leng ldquoContent and chemical compo-sition of carotenoids in persimmon fruitrdquo Chinese AgriculturalScience Bulletin vol 22 pp 277ndash280 2006 (Chinese)

[57] D Zhao C Zhou and J Tao ldquoCarotenoid accumulation andcarotenogenic genes expression during two types of persimmonfruit (Diospyros kaki L) developmentrdquo Plant Molecular BiologyReporter vol 29 no 3 pp 646ndash654 2011

[58] L Plaza C Colina B D Ancos C Sanchez-Moreno and MPilar Cano ldquoInfluence of ripening and astringency on carote-noid content of high-pressure treated persimmon fruit (Dio-spyros kakiL)rdquo FoodChemistry vol 130 no 3 pp 591ndash597 2012

[59] T Niikawa T Suzuki T Ozeki M Kato and Y Ikoma ldquoChar-acteristics of carotenoid accumulation duringmaturation of theJapanese persimmon lsquoFuyursquordquo Horticultural Research vol 6 pp251ndash256 2007 (Japanese)

[60] G Britton ldquoStructure and properties of carotenoids in relationto functionrdquo The FASEB Journal vol 9 no 15 pp 1551ndash15581995

[61] H G Daood P Biacs B Czinkotai and A Hoschke ldquoChroma-tographic investigation of carotenoids sugars and organic acidsfrom Diospyros kaki fruitsrdquo Food Chemistry vol 45 no 2 pp151ndash155 1992

[62] I-C Jang E-K Jo S-M Bae et al ldquoAntioxidant activity andfatty acid composition of four different persimmon seedsrdquo FoodScience and Technology Research vol 16 no 6 pp 577ndash5842010

[63] J AMenendez L Vellon R Colomer and R Lupu ldquoOleic acidthe main monounsaturated fatty acid of olive oil suppressesHer-2neu (erbB-2) expression and synergistically enhances thegrowth inhibitory effects of trastuzumab (Herceptin) in breastcancer cells with Her-2neu oncogene amplificationrdquo Annals ofOncology vol 16 no 3 pp 359ndash371 2005

[64] W C Willett ldquoThe role of dietary n-6 fatty acids in theprevention of cardiovascular diseaserdquo Journal of CardiovascularMedicine vol 8 no 1 pp S42ndashS45 2007

[65] K Kawakami S Aketa H Sakai Y Watanabe H Nishida andM Hirayama ldquoAntihypertensive and vasorelaxant effects ofwater-soluble proanthocyanidins from persimmon leaf tea inspontaneously hypertensive ratsrdquo Bioscience Biotechnology andBiochemistry vol 75 no 8 pp 1435ndash1439 2011

[66] G Chen J Xue S-X Xu and R-Q Zhang ldquoChemical con-stituents of the leaves of Diospyros kaki and their cytotoxiceffectsrdquo Journal of Asian Natural Products Research vol 9 no4 pp 347ndash353 2007

[67] S Singh and H Joshi ldquoDiospyros kaki (Ebenaceae) a reviewrdquoAsian Journal of Research in Pharmaceutical Science vol 1 no3 pp 55ndash58 2011

[68] J L Navarro A Tarrega M A Sentandreu and E SentandreuldquoPartial purification and characterization of polyphenol oxi-dase from persimmonrdquo Food Chemistry vol 157 pp 283ndash2892014

[69] O V Zillich U Schweiggert-Weisz P Eisner and M KerscherldquoPolyphenols as active ingredients for cosmetic productsrdquoInternational Journal of Cosmetic Science vol 37 no 5 pp 455ndash464 2015

[70] H Palafox-Carlos J F Ayala-Zavala and G A Gonzalez-Aguilar ldquoThe role of dietary fiber in the bioaccessibility andbioavailability of fruit and vegetable antioxidantsrdquo Journal ofFood Science vol 76 no 1 pp R6ndashR15 2011

[71] A Ratz-Łyko J Arct SMajewski andK Pytkowska ldquoInfluenceof polyphenols on the physiological processes in the skinrdquoPhytotherapy Research vol 29 no 4 pp 509ndash517 2015

[72] J Sun Y-F Chu X Wu and R H Liu ldquoAntioxidant andantiproliferative activities of common fruitsrdquo Journal of Agricul-tural and Food Chemistry vol 50 no 25 pp 7449ndash7454 2002

[73] E Sentandreu M Cerdan-Calero J M Halket and J LNavarro ldquoRapid screening of low-molecular-weight phenolsfrom persimmon (Diospyros kaki) pulp using liquid chroma-tographyUVndashvisibleelectrospray mass spectrometry analysisrdquoJournal of the Science of Food and Agriculture vol 95 pp 1648ndash1654 2015

[74] L Bravo ldquoPolyphenols chemistry dietary sources metabolismand nutritional significancerdquo Nutrition Reviews vol 56 no 11pp 317ndash333 1998

[75] T Akagi Y Suzuki A Ikegami et al ldquoCondensed tannin com-position analysis in persimmon (Diospyros kakiThunb) fruit byacid catalysis in the presence of excess phloroglucinolrdquo Journalof the Japanese Society for Horticultural Science vol 79 no 3 pp275ndash281 2010

[76] C Li R Leverence J D Trombley et al ldquoHighmolecularweightpersimmon (Diospyros kaki L) proanthocyanidin a highlygalloylated a-linked tannin with an unusual flavonol terminalunitmyricetinrdquo Journal of Agricultural and FoodChemistry vol58 no 16 pp 9033ndash9042 2010

[77] C A Rice-Evans N J Miller and G Paganga ldquoStructure-antioxidant activity relationships of flavonoids and phenolicacidsrdquo Free Radical Biology andMedicine vol 20 no 7 pp 933ndash956 1996

[78] R Tsao ldquoChemistry and biochemistry of dietary polyphenolsrdquoNutrients vol 2 no 12 pp 1231ndash1246 2010

[79] S Uchida H Ohta R Edamatsu M Hiromatsu A Mori andG I Nomaka ldquoPersimmon tannin prolongs life span of stroke-prone spontaneously hypertensive rats (SHRSP) by acting as afree-radical scavengerrdquo in New Horizons in Preventing Cardio-vascular Diseases Y Yamori and T Strasser Eds pp 15ndash17Academic Press Amsterdam The Netherlands Elsevier NewYork NY USA 1989

[80] S Uchida H Ohta M Niwa et al ldquoProlongation of life spanof stroke-prone spontaneously hypertensive rats (SHRSP)ingesting persimmon tanninrdquo Chemical and PharmaceuticalBulletin vol 38 no 4 pp 1049ndash1052 1990

[81] S Gorinstein G W Kulasek E Bartnikowska et al ldquoThe influ-ence of persimmon peel and persimmon pulp on the lipidmeta-bolism and antioxidant activity of rats fed cholesterolrdquo Journalof Nutritional Biochemistry vol 9 no 4 pp 223ndash227 1998

[82] K Matsumoto A Kadowaki N Ozaki et al ldquoBile acid-bind-ing ability of kaki-tannin from young fruits of persimmon (Dio-spyros kaki) in vitro and in vivordquo Phytotherapy Research vol 25no 4 pp 624ndash628 2011

[83] K Ueda R Kawabata T Irie Y Nakai Y Tohya and T Sak-aguchi ldquoInactivation of pathogenic viruses by plant-derivedtannins strong effects of extracts from persimmon (Diospyros

Journal of Chemistry 11

kaki) on a broad range of virusesrdquo PLoS ONE vol 8 no 1Article ID e55343 10 pages 2013

[84] H Suzuki M Konishi M Kimura T Mori M Suzuki and TIkemi ldquoInhibitory effects ofDiospyros kakiTHUNB Extracts indental caries in ratsrdquo Japanese Journal of Conservative Dentistryvol 50 no 2 pp 140ndash145 2007

[85] S Sakanaka Y Tachibana and Y Okada ldquoPreparation andantioxidant properties of extracts of Japanese persimmon leaftea (Kakinoha-cha)rdquo Food Chemistry vol 89 no 4 pp 569ndash5752005

[86] MHosny and J PN Rosazza ldquoNovel oxidations of (+)-catechinby horseradish peroxidase and laccaserdquo Journal of Agriculturaland Food Chemistry vol 50 no 20 pp 5539ndash5545 2002

[87] J-I Inokuchi H Okabe T Yamauchi and A NagamatsuldquoInhibitors of angiotensin converting enzyme in crude drugsrdquoChemical and Pharmaceutical Bulletin vol 32 no 9 pp 3615ndash3619 1984

[88] Y Tian B Zou L Yang et al ldquoHigh molecular weight per-simmon tannin ameliorates cognition deficits and attenuatesoxidative damage in senescent mice induced by d-galactoserdquoFood andChemical Toxicology vol 49 no 8 pp 1728ndash1736 2011

[89] Y Achiwa H Hibasami H Katsuzaki K Imai and T KomiyaldquoInhibitory effects of persimmon (Diospyros kaki) extract andrelated polyphenol compounds on growth of human lymphoidleukemia cellsrdquo Bioscience Biotechnology and Biochemistry vol61 no 7 pp 1099ndash1101 1997

[90] J Gross Carotenoids vol 123 Academic Press New York NYUSA 1987

[91] B De Ancos E Gonzalez and M P Cano ldquoEffect of high-pressure treatment on the carotenoid composition and theradical scavenging activity of persimmon fruit pureesrdquo Journalof Agricultural and Food Chemistry vol 48 no 8 pp 3542ndash3548 2000

[92] T Matsuo and S Ito ldquoThe chemical structure of Kaki-tanninfrom immature fruit of the persimmon (Diospyros kaki L)rdquoAgricultural and Biological Chemistry vol 42 no 9 pp 1637ndash1643 1978

[93] S Gorinstein M Zemser M Weisz et al ldquoFluorometric anal-ysis of phenolics in persimmonsrdquo Bioscience Biotechnology andBiochemistry vol 58 no 6 pp 1087ndash1092 1994

[94] S O Lee H J LeeMH Yu H G Im and I S Lee ldquoTotal poly-phenol contents and antioxidant activities of methanol extractsfrom vegetables produced in Ullung Islandrdquo Korean Journal ofFood Science and Technology vol 37 no 2 pp 233ndash240 2005

[95] U V Mallavadhani A K Panda and Y R Rao ldquoPharmacologyand chemotaxonomy of Diospyrosrdquo Phytochemistry vol 49 no4 pp 901ndash951 1998

[96] G Block B Patterson and A Subar ldquoFruit vegetables andcancer prevention a review of the epidemiological evidencerdquoNutrition and Cancer vol 18 no 1 pp 1ndash29 1992

[97] G van Poppel ldquoCarotenoids and cancer an updatewith empha-sis on human intervention studiesrdquo European Journal of Cancervol 29 no 9 pp 1335ndash1344 1993

[98] E Giovannucci A Ascherio E B Rimm M J Stampfer G AColditz and W C Willett ldquoIntake of carotenoids and retino inrelation to risk of prostate cancerrdquo Journal of theNational CancerInstitute vol 87 no 23 pp 1767ndash1776 1995

[99] T Johns R L A Mahunnah P Sanaya L Chapman and TTicktin ldquoSaponins and phenolic content in plant dietary addi-tives of a traditional subsistence community the Batemi ofNgorongoro District Tanzaniardquo Journal of Ethnopharmacologyvol 66 no 1 pp 1ndash10 1999

[100] Y Zhang X Lu Y Zhang L Qin and J Zhang ldquoSulfatedmodification and immunomodulatory activity of water-solublepolysaccharides derived from fresh Chinese persimmon fruitrdquoInternational Journal of Biological Macromolecules vol 46 no1 pp 67ndash71 2010

[101] Y-J Moon and Y-S Cha ldquoEffects of persimmon-vinegar onlipid metabolism and alcohol clearance in chronic alcohol-fedratsrdquo Journal of Medicinal Food vol 11 no 1 pp 38ndash45 2008

[102] H S Ahn T I Jeon J Y Lee S G Hwang Y Lim and D KPark ldquoAntioxidative activity of persimmon and grape seedextract in vitro and in vivordquo Nutrition Research vol 22 no 11pp 1265ndash1273 2002

[103] H Itamurah N Murakami and H Nagamatsu ldquoProperty ofkaki-tannin as a functional composition in persimmon fruitflesh and leaves and its solubility in artificial stomach liquidrdquoin Proceedings of the 27th International Horticultural Congressamp Exhibition (IHC rsquo06) vol 8 pp 265ndash267 August 2006

[104] K A Steinmetz and J D Potter ldquoVegetables fruit and cancerprevention a reviewrdquo Journal of the American Dietetic Associa-tion vol 96 no 10 pp 1027ndash1039 1996

[105] A N Nagappa P A Thakurdesai N V Rao and J SinghldquoAntidiabetic activity ofTerminalia catappa Linn fruitsrdquo Journalof Ethnopharmacology vol 88 no 1 pp 45ndash50 2003

[106] K Datta S Sinha and P Chattopadhyay ldquoReactive oxygenspecies in health and diseaserdquoNationalMedical Journal of Indiavol 13 no 6 pp 304ndash310 2000

[107] R R Holman and R C Turner ldquoOral agents and insulin in thetreatment of NIDDMrdquo in Textbook of Diabetes J Williams Edpp 407ndash469 Blackwell Press Oxford UK 1991

[108] F Giacco and M Brownlee ldquoOxidative stress and diabeticcomplicationsrdquo Circulation Research vol 107 no 9 pp 1058ndash1070 2010

[109] B K Rao M M Kesavulu R Giri and C A Rao ldquoAntidiabeticand hypolipidemic effects ofMomordicacymbalariaHook fruitpowder in alloxan-diabetic ratsrdquo Journal of Ethnopharmacologyvol 67 no 1 pp 103ndash109 1999

[110] J K Grover V Vats V Rathi and S S Dawar ldquoTraditionalIndian anti-diabetic plants attenuate progression of renal dam-age in streptozotocin induced diabetic micerdquo Journal of Ethno-pharmacology vol 76 no 3 pp 233ndash238 2001

[111] R K Gupta A N Kesari P S Murthy R Chandra V Tandonand GWatal ldquoHypoglycemic and antidiabetic effect of ethano-lic extract of leaves of Annona squamosa L in experimentalanimalsrdquo Journal of Ethnopharmacology vol 99 no 1 pp 75ndash81 2005

[112] S Gupta N Ahmad A-L Nieminen andHMukhtar ldquoGrowthinhibition cell-cycle dysregulation and induction of apopto-sis by green tea constituent (-)-epigallocatechin-3-gallate inandrogen-sensitive and androgen-insensitive human prostatecarcinoma cellsrdquoToxicology andApplied Pharmacology vol 164no 1 pp 82ndash90 2000

[113] T Yokozawa Y A Kim H Y Kim Y A Lee and G-I NonakaldquoProtective effect of persimmon peel polyphenol against highglucose-induced oxidative stress in LLC-PK1 cellsrdquo Food andChemical Toxicology vol 45 no 10 pp 1979ndash1987 2007

12 Journal of Chemistry

[114] M S Brewer ldquoNatural antioxidants sources compoundsmechanisms of action and potential applicationsrdquo Comprehen-sive Reviews in Food Science and Food Safety vol 10 no 4 pp221ndash247 2011

[115] K Kawakami H Nishida N Tatewaki Y Nakajima T Konishiand M Hirayama ldquoPersimmon leaf extract inhibits the ATMactivity during DNA damage response induced by Doxorubicinin A549 lung adenocarcinoma cellsrdquo Bioscience Biotechnologyand Biochemistry vol 75 no 4 pp 650ndash655 2011

[116] D Steinberg S Parthasarathy T E Carew J C Khoo and JL Witztum ldquoBeyond cholesterol modifications of low-densitylipoprotein that increase its atherogenicityrdquo The New EnglandJournal of Medicine vol 320 no 14 pp 915ndash924 1989

[117] P M Kris-Etherton and C L Keen ldquoEvidence that the anti-oxidant flavonoids in tea and cocoa are beneficial for cardiovas-cular healthrdquo Current Opinion in Lipidology vol 13 no 1 pp41ndash49 2002

[118] C Manach A Mazur and A Scalbert ldquoPolyphenols and pre-vention of cardiovascular diseasesrdquo Current Opinion in Lipidol-ogy vol 16 no 1 pp 77ndash84 2005

[119] J W Anderson B M Smith and N J Gustafson ldquoHealthbenefits and practical aspects of high-fiber dietsrdquo AmericanJournal of Clinical Nutrition vol 59 no 5 pp 1242ndash1247 1994

[120] D Kromhout A Menotti H Kesteloot and S Sans ldquoPreven-tion of coronary heart disease by diet and lifestyle evidencefrom prospective cross-cultural cohort and intervention stud-iesrdquo Circulation vol 105 no 7 pp 893ndash898 2002

[121] E B Rimm M J Stampfer A Ascherio E Giovannucci G AColditz andWCWillett ldquoVitamin E consumption and the riskof coronary heart disease in menrdquo The New England Journal ofMedicine vol 328 no 20 pp 1450ndash1456 1993

[122] L Dauchet J Ferrieres D Arveiler et al ldquoFrequency of fruitand vegetable consumption and coronary heart disease inFrance and Northern Ireland the prime studyrdquo British Journalof Nutrition vol 92 no 6 pp 963ndash972 2004

[123] S Gorinstein GW Kulasek E Bartnikowska et al ldquoThe effectsof diets supplementedwith either whole persimmon or phenol-free persimmon on rats fed cholesterolrdquo Food Chemistry vol70 no 3 pp 303ndash308 2000

[124] M G L Hertog E J M Feskens P C H HollmanM B Katanand D Kromhout ldquoDietary antioxidant flavonoids and risk ofcoronary heart disease the Zutphen Elderly studyrdquoThe Lancetvol 342 no 8878 pp 1007ndash1011 1993

[125] H Seo B D Jeon andR Sungpil ldquoPersimmon vinegar ripeningwith the mountain-cultivated ginseng ingestion reduces bloodlipids and lowers inflammatory cytokines in obese adolescentsrdquoJournal of Exercise Nutrition and Biochemistry vol 19 no 1 pp1ndash10 2015

[126] R H Liu ldquoPotential synergy of phytochemicals in cancerprevention mechanism of actionrdquo Journal of Nutrition vol 134no 12 supplement pp 3479Sndash3485S 2004

[127] S T Mayne ldquoAntioxidant nutrients and chronic disease use ofbiomarkers of exposure and oxidative stress status in epidemi-ologic researchrdquo Journal of Nutrition vol 133 no 3 pp 933sndash940s 2003

[128] H Tapiero D M Townsend and K D Tew ldquoThe role of caro-tenoids in the prevention of human pathologiesrdquo Biomedicineand Pharmacotherapy vol 58 no 2 pp 100ndash110 2004

[129] J Tao and S L Zhang ldquoMetabolismof carotenoid and its regula-tion in garden croprdquo Journal of Zhejiang University (Agricultureamp Life Sciences) vol 29 pp 585ndash590 2003

[130] W Miki ldquoBiological functions and activities of animal caro-tenoidsrdquo Pure and Applied Chemistry vol 63 no 1 pp 141ndash1461991

[131] H Fujiki ldquoGreen tea health benefits as cancer preventive forhumansrdquo Chemical Record vol 5 no 3 pp 119ndash132 2005

[132] A P George and S Redpath ldquoHealth and medicinal benefits ofpersimmon fruit a reviewrdquo Advances in Horticultural Sciencevol 22 no 4 pp 244ndash249 2008

[133] T Hussain S Gupta V M Adhami and H Mukhtar ldquoGreentea constituent epigallocatechin-3-gallate selectively inhibitsCOX-2 without affecting COX-1 expression in human prostatecarcinoma cellsrdquo International Journal of Cancer vol 113 no 4pp 660ndash669 2005

[134] Y-C Wang and U Bachrach ldquoThe specific anti-cancer activityof green tea (minus)-epigallocatechin-3-gallate (EGCG)rdquo AminoAcids vol 22 no 2 pp 131ndash143 2002

[135] O Takayuki ldquoPersimmons your healthy autumn treatsrdquoAsahikawa Information vol 108 pp 1ndash2 2005

[136] T Fukuda and H Shibata ldquoPersimmon calyx extracts as anti-convulsants and to alleviate the side effects of barbituric acidcompoundsrdquo Patent Japanease Kokai Tokkyo Koho vol 6 pp649ndash653 1994

[137] T Matsuno ldquoXanthophylls as precursors of retinoidsrdquo Pure andApplied Chemistry vol 63 no 1 pp 81ndash88 1991

[138] N Gato A Kadowaki N Hashimoto S-I Yokoyama and KMatsumoto ldquoPersimmon fruit tannin-rich fiber reduces choles-terol levels in humansrdquoAnnals of Nutrition andMetabolism vol62 no 1 pp 1ndash6 2013

[139] A Nagao ldquoAbsorption and function of dietary carotenoidsrdquoForum of Nutrition vol 61 pp 55ndash63 2009

[140] PD Fraser andPM Bramley ldquoThebiosynthesis andnutritionaluses of carotenoidsrdquo Progress in Lipid Research vol 43 no 3 pp228ndash265 2004

[141] D Fusco G Colloca M R Lo Monaco and M Cesari ldquoEffectsof antioxidant supplementation on the aging processrdquo ClinicalInterventions in Aging vol 2 no 3 pp 377ndash387 2007

[142] JM Seddon U Ajan and R D Sperduto ldquoDietary carotenoidsvitamins A C and E and advance age-related macular degen-eration Eye Disease Case Study Grouprdquo Journal of AmericanMedical Association vol 272 no 18 pp 1413ndash1420 1992

[143] B-J An J-H Kwak J-M Park et al ldquoInhibition of enzymeactivities and the antiwrinkle effect of polyphenol isolated fromthe persimmon leaf (Diospyros kaki folium) on human skinrdquoDermatologic Surgery vol 31 no 7 pp 848ndash854 2005

[144] H Arakawa M Takasaki N Tajima H Fukamachi and TIgarashi ldquoAntibacterial activities of persimmon extracts relatewith their hydrogen peroxide concentrationrdquo Biological andPharmaceutical Bulletin vol 37 no 7 pp 1119ndash1123 2014

[145] S D Ladas D Kamberoglou G Karamanolis J Vlachogian-nakos and I Zouboulis-Vafiadis ldquoSystematic review Coca-Cola can effectively dissolve gastric phytobezoars as a first-linetreatmentrdquo Alimentary Pharmacology and Therapeutics vol 37no 2 pp 169ndash173 2013

[146] T J Cifuentes C R Robles P P Parrilla et al ldquoPolyphenols andhealth what compounds are involvedrdquo Nutrition Metabolismand Cardiovascular Diseases vol 20 no 1 pp 1ndash6 2010

[147] J Gaya L Barranco A Llompart J Reyes and A ObradorldquoPersimmon bezoars a successful combined therapyrdquoGastroin-testinal Endoscopy vol 55 no 4 pp 581ndash583 2002

[148] P G Hayes and O D Rotstein ldquoGastrointestinal phytobezoarspresentation and managementrdquo Canadian Journal of Surgeryvol 29 no 6 pp 419ndash420 1986

Journal of Chemistry 13

[149] MM Krausz E ZMoriel A Ayalon D Pode and A L DurstldquoSurgical aspects of gastrointestinal persimmon phytobezoartreatmentrdquoThe American Journal of Surgery vol 152 no 5 pp526ndash530 1986

[150] P Walker-Renard ldquoUpdate on the medicinal management ofphytobezoarsrdquo The American Journal of Gastroenterology vol88 no 10 pp 1663ndash1666 1993

[151] S S Ha H S LeeM K Jung et al ldquoAcute intestinal obstructioncaused by a persimmon phytobezoar after dissolution therapywith Coca-Colardquo The Korean Journal of Internal Medicine vol22 no 4 pp 300ndash303 2007

[152] J Han S Kang R Choue et al ldquoFree radical scavenging effectofDiospyros kaki Laminaria japonica andUndaria pinnatifidardquoFitoterapia vol 73 no 7-8 pp 710ndash712 2002

Submit your manuscripts athttpwwwhindawicom

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Page 7: Review Article Chemistry and Functionality of Bioactive ...downloads.hindawi.com/journals/jchem/2016/3424025.pdf · Review Article Chemistry and Functionality of Bioactive Compounds

Journal of Chemistry 7

disease (CAD) In such condition the oxidative stress is char-acterized by the accumulation of metabolites (from the oxi-dation of proteins and lipids) and macrophages Accordingto the hypothesis of oxidative modification the early eventwhich initiates the development of atherogenesis (develop-ment of atheromatous plaques) is the oxidative breakdownof low-density lipoproteins Reactive oxygen species in thevessel wall have been considered to be one of the mostimportant causes of vascular dysfunction [117]

Dietary components having antioxidant properties as thepolyphenols are receiving a lot of attention because of theirability to reduce cardiovascular diseases [118 119] When dietrich in fiber is largely consumed it results in preventionand treatment of diverticular and coronary heart diseases[120] Coronary atherosclerosis especially is inhibited bypreventing oxidation of low-density lipoprotein (LDL) and bynutritional antioxidants like phenolics [121] and vitamins AC and E [122]

Hence many reports have shown that if intake of veg-etables and fruits is increased in diet then chances of coro-nary heart diseases could greatly be reduced [123] Accord-ing to Hertog et al [124] if 100 g of persimmon is con-sumed regularly then it will be sufficient to inhibit occlu-sion of arteries In young fruits of persimmon (Diospyroskaki) tannin is found to have the ability of bonding bile acid[83]

It has been established that addition of persimmon inthe diet hinders the increase in plasma lipid level and henceworks as antiatherosclerosis [80 124] which reduces thechances of mortality by the action of polyphenols [125]Matsumoto et al [82] also reported that the persimmon peelsupplemented diet shows hypocholesterolemic and antiox-idative effect

Total dietary fibers including soluble and insoluble totalphenolics including epicatechin gallic and p-coumaric acidsand concentrations of minerals like Na K Mg Ca Feand Mn are high in peel pulp and whole persimmon fruitcompared to apple [50] Hence persimmon must be givenpreference over apples and some other fruits in selecting anantiatherosclerotic diet Liu [126] reported decline in bloodtriglyceride and total cholesterol contents after intake ofpersimmon vinegar (PV) for 6 weeks

73 Cancer In recent years persimmon has been thefocus of attention for potential medicinal applications forprevention of cancer [47] Carotenoids are naturersquos mostwidespread pigments and have also received substantialattention because of both their provitamin and antioxidantroles [127] Carotenoids possess antioxidant properties thathave been associatedwith cellular protection [128] regulationof cell growth differentiation and apoptosis [129]

Not only are the carotenoid contents responsible forthe superficial appearance (color) and nutritional quality offruit [130] but also they provide potential health benefitsand disease prevention by quenching singlet oxygen andscavenging free radicals [131] Chemoprotective effects ofpersimmon against various forms of cancer are due to thecarotenoid contents [132 133] Persimmon was shown tobe effective in the treatment of prostate and breast cancers

[134] oral carcinoma cells [47] human lymphoid leukemiacells [135] and precancerous colon polyps in women [136]The bioactive compounds in persimmon may also affectmultidrug resistant (MDR) inhibiting activity It enhances theaccumulation of cancer cells due to the reduced activity ofefflux pumps MDR inhibitors from persimmon may helpto treat noncurable cancer because of the modulating effects[47] The calyx (persimmon) extracts act as anticonvulsantsand may alleviate the side effects of barbituric acid com-pounds [103]

8 Other Health Promoting Properties

Dried persimmon snacks were found to be effective inreducing the concentration of alcohol in the blood [55]Similarly Matsuno [137] observed that kaki-tannin foundin persimmon fruit flesh and leaves was soluble in artifi-cial stomach liquid and reduced blood alcohol (40) andacetaldehyde contents (30) Dietary intake of persimmontannin was found to prevent hypercholesterolemia in someanimal models and humans [138]

Some carotenoids present in persimmon are precur-sors of vitamin A [139] and also have immunoregulatory[140] and antiaging effects [141] Carotenoids are inverselylinked with inflammation atherosclerosis cardiovasculardiseases sarcopenia and mortality Carotenoid supplemen-tation improves the antioxidant status and reduces lipidperoxidation

Carotenoids like 120573-carotene 120572-carotene 120573-cryptoxan-thin lycopene and lutein (Figure 2) have been found to beassociated with inflammation and mortality risks [142] Inaddition lutein (carotenoids) present in persimmon peel canhelp protect eye vision [143]

9 Persimmon Leaves and Health

Persimmon leaves and extracts are being used as a greentea oriental medicines deodorants antiallergic substratesand cosmetics (especially for dermatitis) as they prevent skinproblems and have an antiwrinkle effect [68 143] and skinwhitening effect [72] The leaves are brewed into a beverageto release their antioxidant activity and antitumor effects andto inhibit angiotensin converting enzymes as well as alphaamylase [66] The leaves of persimmon possess antithrom-botic activity Arakawa et al [144] demonstrated that a 10000D anticoagulant fraction has been purified from the leavesthat inhibited thrombin-catalyzed fibrin formation with acompetitive inhibition pattern Based on their antimicrobialproperties persimmon leaf-based products have been incor-porated into athletersquos foot socks and soaps and persimmonleaves have been used as a sushi ingredient [145]

10 Unripen Persimmons and Health Issues

Bezoars are thick hard masses formed in gastrointestinaltract usually the stomach [146] Patients who have undergonestomach surgery and have delayed gastric emptying areoften more prone to the development of bezoars [147]Phytobezoars are the most common types of bezoars and

8 Journal of Chemistry

these are composed of skins seeds and vegetative matterincluding lignin cellulose hemicelluloses tannins and othernondigestible matter from fruits and vegetables ingestedDiospyrobezoars are a type of phytobezoars related to theconsumption of persimmon fruit and are common world-wide These are more difficult to treat because of their hardconsistency [146 148 149] Most bezoars in animals arecaused by hairs

When unripe astringent persimmon having a high levelof tannin is ingested a coagulum is formed in the stomachdue to the contact of tannin and shibuol with hydrochloricacid that accumulates cellulose hemicellulose and pro-tein [150] Phytobezoars may require surgical removal orendoscopic treatment as they are usually resistant to drugtreatment [151] Han et al [152] suggested a nonsurgicalapproach for cases of persimmon phytobezoar small intesti-nal obstruction with its partial dissolution of a bezoar byperforming oral and injected Coca-Cola therapy

11 Conclusion

Bioactive compounds particularly phenolics (ferulic p-coumaric and gallic acids) and carotenoids (120573-cryptoxan-thin lycopene 120573-carotene and lutein) are of major interestsin persimmon fruitThese valued bioactive components havestrong antioxidant potential which relates to the variety stageof maturity and fruit parts These functional compoundscan play a significant role in preventing and curing variousailments like diabetes hypercholesterolemia and cancerHence the known impact of natural bioactive compounds toimprove human health has introduced a substantial area ofresearch resulting in extensive advances in biochemical andnutritional sciences

Conflict of Interests

The authors declare that there is no conflict of interestsregarding the publication of this paper

References

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[2] S Yaqub U Farooq T Kausar Z Hayat M Jaskani and S MUllah ldquoHypocholestrolemic effect of persimmon peel powderin rabbitsrdquo Journal of Science International vol 25 no 3 pp605ndash609 2013

[3] M S Butt M T Sultan M Aziz et al ldquoPersimmon (Piospyroskaki) fruit hidden phytochemicals and health claimsrdquo EXCLIJournal vol 14 pp 542ndash561 2015

[4] A H A Hadi M E Duru and A B Martin-Diana ldquoBioactivenatural productsrdquo Journal of Chemistry vol 2013 Article ID208507 1 page 2013

[5] M R Segura Campos J Ruiz Ruiz L Chel-Guerrero and DBetancur Ancona ldquoCoccoloba uvifera (L)(Polygonaceae) fruitphytochemical screening and potential antioxidant activityrdquoJournal of Chemistry vol 2015 Article ID 534954 9 pages 2015

[6] S Karaman O S Toker F Yuksel M Cam A Kayacier andM Dogan ldquoPhysicochemical bioactive and sensory propertiesof persimmon-based ice cream technique for order prefer-ence by similarity to ideal solution to determine optimum con-centrationrdquo Journal of Dairy Science vol 97 no 1 pp 97ndash1102014

[7] M C Caruso F Galgano M Pecora R Tolve M Verrastroand F Favati ldquoImprovement of analytical methods for thedetermination of polyphenolic bioactive compounds in berryfruitsrdquo Journal of Chemistry vol 2015 Article ID 384051 6pages 2015

[8] R H Liu ldquoHealth benefits of fruit and vegetables are fromadditive and synergistic combinations of phytochemicalsrdquo TheAmerican Journal of Clinical Nutrition vol 78 no 3 pp 517Sndash520S 2003

[9] L Dauchet P Amouyel S Hercberg and J Dallongeville ldquoFruitand vegetable consumption and risk of coronary heart diseasea meta-analysis of cohort studiesrdquo Journal of Nutrition vol 136no 10 pp 2588ndash2593 2006

[10] A Denny and J Buttriss ldquoPlant foods and health focuson plant bioactivesrdquo EU 6th Framework Food Quality andSafety Thematic Priority Contract FOOD-CT-2005-513944European Food Information Resource (EuroFIR) Consortium2007

[11] S M K Rates ldquoPlants as source of drugsrdquo Toxicon vol 39 no5 pp 603ndash613 2001

[12] D Zhao C Zhou Y Sheng G Liang and J Tao ldquoMolecularcloning and expression of phytoene synthase lycopene beta-cyclase and beta-carotene hydroxylase genes in persimmon(Diospyros kaki L) fruitsrdquo PlantMolecular Biology Reporter vol29 no 2 pp 345ndash351 2011

[13] K Suzuki S Tsubaki M Fujita N Koyama M Takahashiand K Takazawa ldquoEffects of safflower seed extract on arterialstiffnessrdquo Vascular Health and Risk Management vol 6 no 1pp 1007ndash1014 2010

[14] M S Butt and M T Sultan ldquoGreen tea naturersquos defense againstmalignanciesrdquo Critical Reviews in Food Science and Nutritionvol 49 no 5 pp 463ndash473 2009

[15] I Raskin D M Ribnicky S Komarnytsky et al ldquoPlants andhuman health in the twenty-first centuryrdquo Trends in Biotechnol-ogy vol 20 no 12 pp 522ndash531 2002

[16] S Parab R Kulkarni and U Thatte ldquoHeavy metals in herbalmedicinesrdquo Indian Journal of Gastroenterology vol 22 no 3 pp111ndash112 2003

[17] K L Miller R S Liebowitz and L K Newby ldquoComplementaryand alternative medicine in cardiovascular disease a review ofbiologically based approachesrdquoAmericanHeart Journal vol 147no 3 pp 401ndash411 2004

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[19] M J Li D Liang F Pu F W Ma C M Hou and T LuldquoAscorbate levels and the activity of key enzymes in ascorbatebiosynthesis and recycling in the leaves of 22 Chinese persim-mon cultivarsrdquo Scientia Horticulturae vol 120 no 2 pp 250ndash256 2009

[20] Z Luo ldquoEffect of 1-methylcyclopropene on ripening of posthar-vest persimmon (Diospyros kaki L) fruitrdquo LWTmdashFood Scienceand Technology vol 40 no 2 pp 285ndash291 2007

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[21] A T Oz ldquoCombined effects of 1-methyl cyclopropene (1-MCP)andmodified atmosphere packaging (MAP) on different ripen-ing stages of persimmon fruit during storagerdquo African Journalof Biotechnology vol 10 no 5 pp 807ndash814 2011

[22] M S Akter M Ahmed and J B Eun ldquoDietary fibre compo-nents antioxidant activities and hydration properties of ripepersimmon (Diospyros kaki L cv Daebong) peel powders asaffected by different washing treatmentsrdquo International Journalof Food Science and Technology vol 45 no 7 pp 1464ndash14712010

[23] K Yonemori A Sugiura andM Yamada ldquoPersimmon geneticsand breedingrdquo Plant Breeding Reviews vol 19 pp 191ndash225 2000

[24] P Thomas and T S Chen ldquoQuantitative analyses of majorcarotenoid fatty acid esters in fruits by liquid chromatographypersimmon and papayardquo Journal of Food Science vol 53 no 6pp 1720ndash1722 1988

[25] T Nakagawa A Nakatsuka K Yano et al ldquoExpressed sequencetags from persimmon at different developmental stagesrdquo PlantCell Reports vol 27 no 5 pp 931ndash938 2008

[26] R Veberic J Jurhar M Mikulic-Petkovsek F Stampar andV Schmitzer ldquoComparative study of primary and secondarymetabolites in 11 cultivars of persimmon fruit (Diospyros kakiL)rdquo Food Chemistry vol 119 no 2 pp 477ndash483 2010

[27] A Ikegami S Eguchi A Kitajima K Inoue and K YonemorildquoIdentification of genes involved in proanthocyanidin biosyn-thesis of persimmon (Diospyros kaki) fruitrdquo Plant Science vol172 no 5 pp 1037ndash1047 2007

[28] A Sattar N Bibi and M A Chaudry ldquoPhenolic compoundsin persimmon during maturation and on-tree ripeningrdquo Food Nahrung vol 36 no 5 pp 466ndash472 1992

[29] Y-S Park S-T Jung S-G Kang et al ldquoDrying of persimmons(Diospyros kaki L) and the following changes in the studiedbioactive compounds and the total radical scavenging activi-tiesrdquo LWTmdashFood Science and Technology vol 39 no 7 pp 748ndash755 2006

[30] A Ikegami T Akagi D Potter et al ldquoMolecular identifica-tion of 1-Cys peroxiredoxin and anthocyanidinflavonol 3-O-galactosyltransferase from proanthocyanidin-rich young fruitsof persimmon (Diospyros kakiThunb)rdquo Planta vol 230 no 4pp 841ndash855 2009

[31] T Radha and L Mathew Fruit Crops Horticulture ScienceSeries Jai Baharat Press 2007

[32] H Yakushiji ldquoRecent persimmon research in Japanrdquo JapaneseJournal of Plant Science vol 1 pp 42ndash62 2007

[33] X N Chen J F Fan X Yue X R Wu and L T Li ldquoRadicalscavenging activity and phenolic compounds in persimmon(Diospyros kaki L cv Mopan)rdquo Journal of Food Science vol 73no 1 pp C24ndashC28 2008

[34] H R Wang P Leng and C S Wang ldquoEffect of absorbentson storage quality of the Mopan persimmonrdquo Journal ShanxiAgriculture and Science vol 33 no 1 pp 59ndash61 2005

[35] X H Guo S Z Fang J Wang X X Guo L Q Xu and L YuanldquoStudy on the infection of the Mopan persimmon quality bycarbon dioxiderdquo Food Research Developments vol 27 pp 156ndash159 2006

[36] S Li P Zhang J K Li L Wang and Y F Huang ldquoEffect of1-methylcyclopropene for the Mopan persimmon crispiness-keeping under ambient temperaturerdquo Storing Process vol 6 pp13ndash16 2006

[37] J L Vazquez-Gutierrez I Hernando and A Quiles ldquoChangesin tannin solubility and microstructure of high hydrostaticpressurendashtreated persimmon cubes during storage at 4∘CrdquoEuropean Food Research and Technology vol 237 no 1 pp 9ndash172013

[38] N Bibi A B Khattak and ZMehmood ldquoQuality improvementand shelf life extension of persimmon fruit (Diospyros kaki)rdquoJournal of Food Engineering vol 79 no 4 pp 1359ndash1363 2007

[39] S Kondo H Yoshikawa and R Katayama ldquoAntioxidant activityin astringent and non-astringent persimmonsrdquo Journal of Hor-ticultural Science and Biotechnology vol 79 no 3 pp 390ndash3942004

[40] X Wei F Liu Z Qiu Y Shao and Y He ldquoRipeness classifica-tion of astringent persimmon using hyperspectral imagingtechniquerdquo Food and Bioprocess Technology vol 7 no 5 pp1371ndash1380 2014

[41] K P Wright and A A Kader ldquoEffect of controlled-atmospherestorage on the quality and carotenoid content of sliced persim-mons and peachesrdquo Postharvest Biology and Technology vol 10no 1 pp 89ndash97 1997

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2deastringency treatment on flesh disorders

induced by mechanical damage in persimmon Biochemicaland microstructural studiesrdquo Food Chemistry vol 145 pp 454ndash463 2014

[43] C J Xu and S L Zhang ldquoCarotenoid biosynthesis and its regu-lation in plantsrdquo Plant Physiology and Communication vol 36pp 64ndash70 2000

[44] E Bellini G Giannelli and E Picardi ldquoPanoramica varietaledel Kaki nel mondo e orientamenti produttivi per lrsquoItaliardquoLrsquoinformatore Agrario vol 44 no 47 pp 47ndash88 2011

[45] USDA-Agriculture Research Service National AgriculturalLibrary Beltsville Md USA vol 44 pp 47ndash88 1998

[46] M Kawase N Motohashi K Satoh et al ldquoBiological activityof persimmon (Diospyros kaki) peel extractsrdquo PhytotherapyResearch vol 17 no 5 pp 495ndash500 2003

[47] W Bei W Peng Y Ma and A Xu ldquoFlavonoids from the leavesof Diospyros kaki reduce hydrogen peroxide-induced injury ofNG108-15 cellsrdquo Life Sciences vol 76 no 17 pp 1975ndash1988 2005

[48] S-O Lee S-K Chung and I-S Lee ldquoThe antidiabetic effect ofdietary persimmon (Diospyros kaki L cv sangjudungsi) peel instreptozotocin-induced daibetic ratsrdquo Journal of Food Sciencevol 71 no 3 pp S293ndashS298 2006

[49] S Gorinstein Z Zachwieja M Folta et al ldquoComparative con-tents of dietary fiber total phenolics and minerals in persim-mons and applesrdquo Journal of Agricultural and Food Chemistryvol 49 no 2 pp 952ndash957 2001

[50] H Leontowicz S Gorinstein A Lojek et al ldquoComparativecontent of some bioactive compounds in apples peaches andpears and their influence on lipids and antioxidant capacity inratsrdquo Journal of Nutritional Biochemistry vol 13 no 10 pp 603ndash610 2002

[51] Y A Lee E J Cho and T Yokozawa ldquoProtective effect of per-simmon (Diospyros kaki) peel proanthocyanidin against oxida-tive damage under H

2O2-induced cellular senescencerdquo Biolog-

ical and Pharmaceutical Bulletin vol 31 no 6 pp 1265ndash12692008

[52] A Subagio N Morita and S Sawada ldquoCarotenoids and theirfatty-acid esters in banana peelrdquo Journal of Nutritional Scienceand Vitaminology vol 42 no 6 pp 553ndash566 1996

10 Journal of Chemistry

[53] Y J Yang and S J Kim ldquoChanges in chlorophyll and carotenoidcontents during cold and CA storage and characterization ofthe carotenoids in the peel of lsquoFujirsquo apple fruitrdquo Journal of KoreanSociety and Horticultural Science vol 36 pp 500ndash505 1995

[54] Y C Kim J B Kim K J Cho I S Lee and S K ChungldquoCarotenoid content of Korean persimmon peel and theirchanges in storagerdquo Food Science and Biotechnology vol 11 no5 pp 477ndash479 2002

[55] J Tous and L Ferguson ldquoMediterranean fruitsrdquo in Progress inNew Crops J Janick Ed pp 416ndash430 ASHS Press ArlingtonVa USA 1996

[56] B YuanH L Xu and S P Leng ldquoContent and chemical compo-sition of carotenoids in persimmon fruitrdquo Chinese AgriculturalScience Bulletin vol 22 pp 277ndash280 2006 (Chinese)

[57] D Zhao C Zhou and J Tao ldquoCarotenoid accumulation andcarotenogenic genes expression during two types of persimmonfruit (Diospyros kaki L) developmentrdquo Plant Molecular BiologyReporter vol 29 no 3 pp 646ndash654 2011

[58] L Plaza C Colina B D Ancos C Sanchez-Moreno and MPilar Cano ldquoInfluence of ripening and astringency on carote-noid content of high-pressure treated persimmon fruit (Dio-spyros kakiL)rdquo FoodChemistry vol 130 no 3 pp 591ndash597 2012

[59] T Niikawa T Suzuki T Ozeki M Kato and Y Ikoma ldquoChar-acteristics of carotenoid accumulation duringmaturation of theJapanese persimmon lsquoFuyursquordquo Horticultural Research vol 6 pp251ndash256 2007 (Japanese)

[60] G Britton ldquoStructure and properties of carotenoids in relationto functionrdquo The FASEB Journal vol 9 no 15 pp 1551ndash15581995

[61] H G Daood P Biacs B Czinkotai and A Hoschke ldquoChroma-tographic investigation of carotenoids sugars and organic acidsfrom Diospyros kaki fruitsrdquo Food Chemistry vol 45 no 2 pp151ndash155 1992

[62] I-C Jang E-K Jo S-M Bae et al ldquoAntioxidant activity andfatty acid composition of four different persimmon seedsrdquo FoodScience and Technology Research vol 16 no 6 pp 577ndash5842010

[63] J AMenendez L Vellon R Colomer and R Lupu ldquoOleic acidthe main monounsaturated fatty acid of olive oil suppressesHer-2neu (erbB-2) expression and synergistically enhances thegrowth inhibitory effects of trastuzumab (Herceptin) in breastcancer cells with Her-2neu oncogene amplificationrdquo Annals ofOncology vol 16 no 3 pp 359ndash371 2005

[64] W C Willett ldquoThe role of dietary n-6 fatty acids in theprevention of cardiovascular diseaserdquo Journal of CardiovascularMedicine vol 8 no 1 pp S42ndashS45 2007

[65] K Kawakami S Aketa H Sakai Y Watanabe H Nishida andM Hirayama ldquoAntihypertensive and vasorelaxant effects ofwater-soluble proanthocyanidins from persimmon leaf tea inspontaneously hypertensive ratsrdquo Bioscience Biotechnology andBiochemistry vol 75 no 8 pp 1435ndash1439 2011

[66] G Chen J Xue S-X Xu and R-Q Zhang ldquoChemical con-stituents of the leaves of Diospyros kaki and their cytotoxiceffectsrdquo Journal of Asian Natural Products Research vol 9 no4 pp 347ndash353 2007

[67] S Singh and H Joshi ldquoDiospyros kaki (Ebenaceae) a reviewrdquoAsian Journal of Research in Pharmaceutical Science vol 1 no3 pp 55ndash58 2011

[68] J L Navarro A Tarrega M A Sentandreu and E SentandreuldquoPartial purification and characterization of polyphenol oxi-dase from persimmonrdquo Food Chemistry vol 157 pp 283ndash2892014

[69] O V Zillich U Schweiggert-Weisz P Eisner and M KerscherldquoPolyphenols as active ingredients for cosmetic productsrdquoInternational Journal of Cosmetic Science vol 37 no 5 pp 455ndash464 2015

[70] H Palafox-Carlos J F Ayala-Zavala and G A Gonzalez-Aguilar ldquoThe role of dietary fiber in the bioaccessibility andbioavailability of fruit and vegetable antioxidantsrdquo Journal ofFood Science vol 76 no 1 pp R6ndashR15 2011

[71] A Ratz-Łyko J Arct SMajewski andK Pytkowska ldquoInfluenceof polyphenols on the physiological processes in the skinrdquoPhytotherapy Research vol 29 no 4 pp 509ndash517 2015

[72] J Sun Y-F Chu X Wu and R H Liu ldquoAntioxidant andantiproliferative activities of common fruitsrdquo Journal of Agricul-tural and Food Chemistry vol 50 no 25 pp 7449ndash7454 2002

[73] E Sentandreu M Cerdan-Calero J M Halket and J LNavarro ldquoRapid screening of low-molecular-weight phenolsfrom persimmon (Diospyros kaki) pulp using liquid chroma-tographyUVndashvisibleelectrospray mass spectrometry analysisrdquoJournal of the Science of Food and Agriculture vol 95 pp 1648ndash1654 2015

[74] L Bravo ldquoPolyphenols chemistry dietary sources metabolismand nutritional significancerdquo Nutrition Reviews vol 56 no 11pp 317ndash333 1998

[75] T Akagi Y Suzuki A Ikegami et al ldquoCondensed tannin com-position analysis in persimmon (Diospyros kakiThunb) fruit byacid catalysis in the presence of excess phloroglucinolrdquo Journalof the Japanese Society for Horticultural Science vol 79 no 3 pp275ndash281 2010

[76] C Li R Leverence J D Trombley et al ldquoHighmolecularweightpersimmon (Diospyros kaki L) proanthocyanidin a highlygalloylated a-linked tannin with an unusual flavonol terminalunitmyricetinrdquo Journal of Agricultural and FoodChemistry vol58 no 16 pp 9033ndash9042 2010

[77] C A Rice-Evans N J Miller and G Paganga ldquoStructure-antioxidant activity relationships of flavonoids and phenolicacidsrdquo Free Radical Biology andMedicine vol 20 no 7 pp 933ndash956 1996

[78] R Tsao ldquoChemistry and biochemistry of dietary polyphenolsrdquoNutrients vol 2 no 12 pp 1231ndash1246 2010

[79] S Uchida H Ohta R Edamatsu M Hiromatsu A Mori andG I Nomaka ldquoPersimmon tannin prolongs life span of stroke-prone spontaneously hypertensive rats (SHRSP) by acting as afree-radical scavengerrdquo in New Horizons in Preventing Cardio-vascular Diseases Y Yamori and T Strasser Eds pp 15ndash17Academic Press Amsterdam The Netherlands Elsevier NewYork NY USA 1989

[80] S Uchida H Ohta M Niwa et al ldquoProlongation of life spanof stroke-prone spontaneously hypertensive rats (SHRSP)ingesting persimmon tanninrdquo Chemical and PharmaceuticalBulletin vol 38 no 4 pp 1049ndash1052 1990

[81] S Gorinstein G W Kulasek E Bartnikowska et al ldquoThe influ-ence of persimmon peel and persimmon pulp on the lipidmeta-bolism and antioxidant activity of rats fed cholesterolrdquo Journalof Nutritional Biochemistry vol 9 no 4 pp 223ndash227 1998

[82] K Matsumoto A Kadowaki N Ozaki et al ldquoBile acid-bind-ing ability of kaki-tannin from young fruits of persimmon (Dio-spyros kaki) in vitro and in vivordquo Phytotherapy Research vol 25no 4 pp 624ndash628 2011

[83] K Ueda R Kawabata T Irie Y Nakai Y Tohya and T Sak-aguchi ldquoInactivation of pathogenic viruses by plant-derivedtannins strong effects of extracts from persimmon (Diospyros

Journal of Chemistry 11

kaki) on a broad range of virusesrdquo PLoS ONE vol 8 no 1Article ID e55343 10 pages 2013

[84] H Suzuki M Konishi M Kimura T Mori M Suzuki and TIkemi ldquoInhibitory effects ofDiospyros kakiTHUNB Extracts indental caries in ratsrdquo Japanese Journal of Conservative Dentistryvol 50 no 2 pp 140ndash145 2007

[85] S Sakanaka Y Tachibana and Y Okada ldquoPreparation andantioxidant properties of extracts of Japanese persimmon leaftea (Kakinoha-cha)rdquo Food Chemistry vol 89 no 4 pp 569ndash5752005

[86] MHosny and J PN Rosazza ldquoNovel oxidations of (+)-catechinby horseradish peroxidase and laccaserdquo Journal of Agriculturaland Food Chemistry vol 50 no 20 pp 5539ndash5545 2002

[87] J-I Inokuchi H Okabe T Yamauchi and A NagamatsuldquoInhibitors of angiotensin converting enzyme in crude drugsrdquoChemical and Pharmaceutical Bulletin vol 32 no 9 pp 3615ndash3619 1984

[88] Y Tian B Zou L Yang et al ldquoHigh molecular weight per-simmon tannin ameliorates cognition deficits and attenuatesoxidative damage in senescent mice induced by d-galactoserdquoFood andChemical Toxicology vol 49 no 8 pp 1728ndash1736 2011

[89] Y Achiwa H Hibasami H Katsuzaki K Imai and T KomiyaldquoInhibitory effects of persimmon (Diospyros kaki) extract andrelated polyphenol compounds on growth of human lymphoidleukemia cellsrdquo Bioscience Biotechnology and Biochemistry vol61 no 7 pp 1099ndash1101 1997

[90] J Gross Carotenoids vol 123 Academic Press New York NYUSA 1987

[91] B De Ancos E Gonzalez and M P Cano ldquoEffect of high-pressure treatment on the carotenoid composition and theradical scavenging activity of persimmon fruit pureesrdquo Journalof Agricultural and Food Chemistry vol 48 no 8 pp 3542ndash3548 2000

[92] T Matsuo and S Ito ldquoThe chemical structure of Kaki-tanninfrom immature fruit of the persimmon (Diospyros kaki L)rdquoAgricultural and Biological Chemistry vol 42 no 9 pp 1637ndash1643 1978

[93] S Gorinstein M Zemser M Weisz et al ldquoFluorometric anal-ysis of phenolics in persimmonsrdquo Bioscience Biotechnology andBiochemistry vol 58 no 6 pp 1087ndash1092 1994

[94] S O Lee H J LeeMH Yu H G Im and I S Lee ldquoTotal poly-phenol contents and antioxidant activities of methanol extractsfrom vegetables produced in Ullung Islandrdquo Korean Journal ofFood Science and Technology vol 37 no 2 pp 233ndash240 2005

[95] U V Mallavadhani A K Panda and Y R Rao ldquoPharmacologyand chemotaxonomy of Diospyrosrdquo Phytochemistry vol 49 no4 pp 901ndash951 1998

[96] G Block B Patterson and A Subar ldquoFruit vegetables andcancer prevention a review of the epidemiological evidencerdquoNutrition and Cancer vol 18 no 1 pp 1ndash29 1992

[97] G van Poppel ldquoCarotenoids and cancer an updatewith empha-sis on human intervention studiesrdquo European Journal of Cancervol 29 no 9 pp 1335ndash1344 1993

[98] E Giovannucci A Ascherio E B Rimm M J Stampfer G AColditz and W C Willett ldquoIntake of carotenoids and retino inrelation to risk of prostate cancerrdquo Journal of theNational CancerInstitute vol 87 no 23 pp 1767ndash1776 1995

[99] T Johns R L A Mahunnah P Sanaya L Chapman and TTicktin ldquoSaponins and phenolic content in plant dietary addi-tives of a traditional subsistence community the Batemi ofNgorongoro District Tanzaniardquo Journal of Ethnopharmacologyvol 66 no 1 pp 1ndash10 1999

[100] Y Zhang X Lu Y Zhang L Qin and J Zhang ldquoSulfatedmodification and immunomodulatory activity of water-solublepolysaccharides derived from fresh Chinese persimmon fruitrdquoInternational Journal of Biological Macromolecules vol 46 no1 pp 67ndash71 2010

[101] Y-J Moon and Y-S Cha ldquoEffects of persimmon-vinegar onlipid metabolism and alcohol clearance in chronic alcohol-fedratsrdquo Journal of Medicinal Food vol 11 no 1 pp 38ndash45 2008

[102] H S Ahn T I Jeon J Y Lee S G Hwang Y Lim and D KPark ldquoAntioxidative activity of persimmon and grape seedextract in vitro and in vivordquo Nutrition Research vol 22 no 11pp 1265ndash1273 2002

[103] H Itamurah N Murakami and H Nagamatsu ldquoProperty ofkaki-tannin as a functional composition in persimmon fruitflesh and leaves and its solubility in artificial stomach liquidrdquoin Proceedings of the 27th International Horticultural Congressamp Exhibition (IHC rsquo06) vol 8 pp 265ndash267 August 2006

[104] K A Steinmetz and J D Potter ldquoVegetables fruit and cancerprevention a reviewrdquo Journal of the American Dietetic Associa-tion vol 96 no 10 pp 1027ndash1039 1996

[105] A N Nagappa P A Thakurdesai N V Rao and J SinghldquoAntidiabetic activity ofTerminalia catappa Linn fruitsrdquo Journalof Ethnopharmacology vol 88 no 1 pp 45ndash50 2003

[106] K Datta S Sinha and P Chattopadhyay ldquoReactive oxygenspecies in health and diseaserdquoNationalMedical Journal of Indiavol 13 no 6 pp 304ndash310 2000

[107] R R Holman and R C Turner ldquoOral agents and insulin in thetreatment of NIDDMrdquo in Textbook of Diabetes J Williams Edpp 407ndash469 Blackwell Press Oxford UK 1991

[108] F Giacco and M Brownlee ldquoOxidative stress and diabeticcomplicationsrdquo Circulation Research vol 107 no 9 pp 1058ndash1070 2010

[109] B K Rao M M Kesavulu R Giri and C A Rao ldquoAntidiabeticand hypolipidemic effects ofMomordicacymbalariaHook fruitpowder in alloxan-diabetic ratsrdquo Journal of Ethnopharmacologyvol 67 no 1 pp 103ndash109 1999

[110] J K Grover V Vats V Rathi and S S Dawar ldquoTraditionalIndian anti-diabetic plants attenuate progression of renal dam-age in streptozotocin induced diabetic micerdquo Journal of Ethno-pharmacology vol 76 no 3 pp 233ndash238 2001

[111] R K Gupta A N Kesari P S Murthy R Chandra V Tandonand GWatal ldquoHypoglycemic and antidiabetic effect of ethano-lic extract of leaves of Annona squamosa L in experimentalanimalsrdquo Journal of Ethnopharmacology vol 99 no 1 pp 75ndash81 2005

[112] S Gupta N Ahmad A-L Nieminen andHMukhtar ldquoGrowthinhibition cell-cycle dysregulation and induction of apopto-sis by green tea constituent (-)-epigallocatechin-3-gallate inandrogen-sensitive and androgen-insensitive human prostatecarcinoma cellsrdquoToxicology andApplied Pharmacology vol 164no 1 pp 82ndash90 2000

[113] T Yokozawa Y A Kim H Y Kim Y A Lee and G-I NonakaldquoProtective effect of persimmon peel polyphenol against highglucose-induced oxidative stress in LLC-PK1 cellsrdquo Food andChemical Toxicology vol 45 no 10 pp 1979ndash1987 2007

12 Journal of Chemistry

[114] M S Brewer ldquoNatural antioxidants sources compoundsmechanisms of action and potential applicationsrdquo Comprehen-sive Reviews in Food Science and Food Safety vol 10 no 4 pp221ndash247 2011

[115] K Kawakami H Nishida N Tatewaki Y Nakajima T Konishiand M Hirayama ldquoPersimmon leaf extract inhibits the ATMactivity during DNA damage response induced by Doxorubicinin A549 lung adenocarcinoma cellsrdquo Bioscience Biotechnologyand Biochemistry vol 75 no 4 pp 650ndash655 2011

[116] D Steinberg S Parthasarathy T E Carew J C Khoo and JL Witztum ldquoBeyond cholesterol modifications of low-densitylipoprotein that increase its atherogenicityrdquo The New EnglandJournal of Medicine vol 320 no 14 pp 915ndash924 1989

[117] P M Kris-Etherton and C L Keen ldquoEvidence that the anti-oxidant flavonoids in tea and cocoa are beneficial for cardiovas-cular healthrdquo Current Opinion in Lipidology vol 13 no 1 pp41ndash49 2002

[118] C Manach A Mazur and A Scalbert ldquoPolyphenols and pre-vention of cardiovascular diseasesrdquo Current Opinion in Lipidol-ogy vol 16 no 1 pp 77ndash84 2005

[119] J W Anderson B M Smith and N J Gustafson ldquoHealthbenefits and practical aspects of high-fiber dietsrdquo AmericanJournal of Clinical Nutrition vol 59 no 5 pp 1242ndash1247 1994

[120] D Kromhout A Menotti H Kesteloot and S Sans ldquoPreven-tion of coronary heart disease by diet and lifestyle evidencefrom prospective cross-cultural cohort and intervention stud-iesrdquo Circulation vol 105 no 7 pp 893ndash898 2002

[121] E B Rimm M J Stampfer A Ascherio E Giovannucci G AColditz andWCWillett ldquoVitamin E consumption and the riskof coronary heart disease in menrdquo The New England Journal ofMedicine vol 328 no 20 pp 1450ndash1456 1993

[122] L Dauchet J Ferrieres D Arveiler et al ldquoFrequency of fruitand vegetable consumption and coronary heart disease inFrance and Northern Ireland the prime studyrdquo British Journalof Nutrition vol 92 no 6 pp 963ndash972 2004

[123] S Gorinstein GW Kulasek E Bartnikowska et al ldquoThe effectsof diets supplementedwith either whole persimmon or phenol-free persimmon on rats fed cholesterolrdquo Food Chemistry vol70 no 3 pp 303ndash308 2000

[124] M G L Hertog E J M Feskens P C H HollmanM B Katanand D Kromhout ldquoDietary antioxidant flavonoids and risk ofcoronary heart disease the Zutphen Elderly studyrdquoThe Lancetvol 342 no 8878 pp 1007ndash1011 1993

[125] H Seo B D Jeon andR Sungpil ldquoPersimmon vinegar ripeningwith the mountain-cultivated ginseng ingestion reduces bloodlipids and lowers inflammatory cytokines in obese adolescentsrdquoJournal of Exercise Nutrition and Biochemistry vol 19 no 1 pp1ndash10 2015

[126] R H Liu ldquoPotential synergy of phytochemicals in cancerprevention mechanism of actionrdquo Journal of Nutrition vol 134no 12 supplement pp 3479Sndash3485S 2004

[127] S T Mayne ldquoAntioxidant nutrients and chronic disease use ofbiomarkers of exposure and oxidative stress status in epidemi-ologic researchrdquo Journal of Nutrition vol 133 no 3 pp 933sndash940s 2003

[128] H Tapiero D M Townsend and K D Tew ldquoThe role of caro-tenoids in the prevention of human pathologiesrdquo Biomedicineand Pharmacotherapy vol 58 no 2 pp 100ndash110 2004

[129] J Tao and S L Zhang ldquoMetabolismof carotenoid and its regula-tion in garden croprdquo Journal of Zhejiang University (Agricultureamp Life Sciences) vol 29 pp 585ndash590 2003

[130] W Miki ldquoBiological functions and activities of animal caro-tenoidsrdquo Pure and Applied Chemistry vol 63 no 1 pp 141ndash1461991

[131] H Fujiki ldquoGreen tea health benefits as cancer preventive forhumansrdquo Chemical Record vol 5 no 3 pp 119ndash132 2005

[132] A P George and S Redpath ldquoHealth and medicinal benefits ofpersimmon fruit a reviewrdquo Advances in Horticultural Sciencevol 22 no 4 pp 244ndash249 2008

[133] T Hussain S Gupta V M Adhami and H Mukhtar ldquoGreentea constituent epigallocatechin-3-gallate selectively inhibitsCOX-2 without affecting COX-1 expression in human prostatecarcinoma cellsrdquo International Journal of Cancer vol 113 no 4pp 660ndash669 2005

[134] Y-C Wang and U Bachrach ldquoThe specific anti-cancer activityof green tea (minus)-epigallocatechin-3-gallate (EGCG)rdquo AminoAcids vol 22 no 2 pp 131ndash143 2002

[135] O Takayuki ldquoPersimmons your healthy autumn treatsrdquoAsahikawa Information vol 108 pp 1ndash2 2005

[136] T Fukuda and H Shibata ldquoPersimmon calyx extracts as anti-convulsants and to alleviate the side effects of barbituric acidcompoundsrdquo Patent Japanease Kokai Tokkyo Koho vol 6 pp649ndash653 1994

[137] T Matsuno ldquoXanthophylls as precursors of retinoidsrdquo Pure andApplied Chemistry vol 63 no 1 pp 81ndash88 1991

[138] N Gato A Kadowaki N Hashimoto S-I Yokoyama and KMatsumoto ldquoPersimmon fruit tannin-rich fiber reduces choles-terol levels in humansrdquoAnnals of Nutrition andMetabolism vol62 no 1 pp 1ndash6 2013

[139] A Nagao ldquoAbsorption and function of dietary carotenoidsrdquoForum of Nutrition vol 61 pp 55ndash63 2009

[140] PD Fraser andPM Bramley ldquoThebiosynthesis andnutritionaluses of carotenoidsrdquo Progress in Lipid Research vol 43 no 3 pp228ndash265 2004

[141] D Fusco G Colloca M R Lo Monaco and M Cesari ldquoEffectsof antioxidant supplementation on the aging processrdquo ClinicalInterventions in Aging vol 2 no 3 pp 377ndash387 2007

[142] JM Seddon U Ajan and R D Sperduto ldquoDietary carotenoidsvitamins A C and E and advance age-related macular degen-eration Eye Disease Case Study Grouprdquo Journal of AmericanMedical Association vol 272 no 18 pp 1413ndash1420 1992

[143] B-J An J-H Kwak J-M Park et al ldquoInhibition of enzymeactivities and the antiwrinkle effect of polyphenol isolated fromthe persimmon leaf (Diospyros kaki folium) on human skinrdquoDermatologic Surgery vol 31 no 7 pp 848ndash854 2005

[144] H Arakawa M Takasaki N Tajima H Fukamachi and TIgarashi ldquoAntibacterial activities of persimmon extracts relatewith their hydrogen peroxide concentrationrdquo Biological andPharmaceutical Bulletin vol 37 no 7 pp 1119ndash1123 2014

[145] S D Ladas D Kamberoglou G Karamanolis J Vlachogian-nakos and I Zouboulis-Vafiadis ldquoSystematic review Coca-Cola can effectively dissolve gastric phytobezoars as a first-linetreatmentrdquo Alimentary Pharmacology and Therapeutics vol 37no 2 pp 169ndash173 2013

[146] T J Cifuentes C R Robles P P Parrilla et al ldquoPolyphenols andhealth what compounds are involvedrdquo Nutrition Metabolismand Cardiovascular Diseases vol 20 no 1 pp 1ndash6 2010

[147] J Gaya L Barranco A Llompart J Reyes and A ObradorldquoPersimmon bezoars a successful combined therapyrdquoGastroin-testinal Endoscopy vol 55 no 4 pp 581ndash583 2002

[148] P G Hayes and O D Rotstein ldquoGastrointestinal phytobezoarspresentation and managementrdquo Canadian Journal of Surgeryvol 29 no 6 pp 419ndash420 1986

Journal of Chemistry 13

[149] MM Krausz E ZMoriel A Ayalon D Pode and A L DurstldquoSurgical aspects of gastrointestinal persimmon phytobezoartreatmentrdquoThe American Journal of Surgery vol 152 no 5 pp526ndash530 1986

[150] P Walker-Renard ldquoUpdate on the medicinal management ofphytobezoarsrdquo The American Journal of Gastroenterology vol88 no 10 pp 1663ndash1666 1993

[151] S S Ha H S LeeM K Jung et al ldquoAcute intestinal obstructioncaused by a persimmon phytobezoar after dissolution therapywith Coca-Colardquo The Korean Journal of Internal Medicine vol22 no 4 pp 300ndash303 2007

[152] J Han S Kang R Choue et al ldquoFree radical scavenging effectofDiospyros kaki Laminaria japonica andUndaria pinnatifidardquoFitoterapia vol 73 no 7-8 pp 710ndash712 2002

Submit your manuscripts athttpwwwhindawicom

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Inorganic ChemistryInternational Journal of

Hindawi Publishing Corporation httpwwwhindawicom Volume 2014

International Journal ofPhotoenergy

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Carbohydrate Chemistry

International Journal of

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Journal of

Chemistry

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Advances in

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Analytical Methods in Chemistry

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Bioinorganic Chemistry and ApplicationsHindawi Publishing Corporationhttpwwwhindawicom Volume 2014

SpectroscopyInternational Journal of

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Medicinal ChemistryInternational Journal of

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Chromatography Research International

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Applied ChemistryJournal of

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CatalystsJournal of

Page 8: Review Article Chemistry and Functionality of Bioactive ...downloads.hindawi.com/journals/jchem/2016/3424025.pdf · Review Article Chemistry and Functionality of Bioactive Compounds

8 Journal of Chemistry

these are composed of skins seeds and vegetative matterincluding lignin cellulose hemicelluloses tannins and othernondigestible matter from fruits and vegetables ingestedDiospyrobezoars are a type of phytobezoars related to theconsumption of persimmon fruit and are common world-wide These are more difficult to treat because of their hardconsistency [146 148 149] Most bezoars in animals arecaused by hairs

When unripe astringent persimmon having a high levelof tannin is ingested a coagulum is formed in the stomachdue to the contact of tannin and shibuol with hydrochloricacid that accumulates cellulose hemicellulose and pro-tein [150] Phytobezoars may require surgical removal orendoscopic treatment as they are usually resistant to drugtreatment [151] Han et al [152] suggested a nonsurgicalapproach for cases of persimmon phytobezoar small intesti-nal obstruction with its partial dissolution of a bezoar byperforming oral and injected Coca-Cola therapy

11 Conclusion

Bioactive compounds particularly phenolics (ferulic p-coumaric and gallic acids) and carotenoids (120573-cryptoxan-thin lycopene 120573-carotene and lutein) are of major interestsin persimmon fruitThese valued bioactive components havestrong antioxidant potential which relates to the variety stageof maturity and fruit parts These functional compoundscan play a significant role in preventing and curing variousailments like diabetes hypercholesterolemia and cancerHence the known impact of natural bioactive compounds toimprove human health has introduced a substantial area ofresearch resulting in extensive advances in biochemical andnutritional sciences

Conflict of Interests

The authors declare that there is no conflict of interestsregarding the publication of this paper

References

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[2] S Yaqub U Farooq T Kausar Z Hayat M Jaskani and S MUllah ldquoHypocholestrolemic effect of persimmon peel powderin rabbitsrdquo Journal of Science International vol 25 no 3 pp605ndash609 2013

[3] M S Butt M T Sultan M Aziz et al ldquoPersimmon (Piospyroskaki) fruit hidden phytochemicals and health claimsrdquo EXCLIJournal vol 14 pp 542ndash561 2015

[4] A H A Hadi M E Duru and A B Martin-Diana ldquoBioactivenatural productsrdquo Journal of Chemistry vol 2013 Article ID208507 1 page 2013

[5] M R Segura Campos J Ruiz Ruiz L Chel-Guerrero and DBetancur Ancona ldquoCoccoloba uvifera (L)(Polygonaceae) fruitphytochemical screening and potential antioxidant activityrdquoJournal of Chemistry vol 2015 Article ID 534954 9 pages 2015

[6] S Karaman O S Toker F Yuksel M Cam A Kayacier andM Dogan ldquoPhysicochemical bioactive and sensory propertiesof persimmon-based ice cream technique for order prefer-ence by similarity to ideal solution to determine optimum con-centrationrdquo Journal of Dairy Science vol 97 no 1 pp 97ndash1102014

[7] M C Caruso F Galgano M Pecora R Tolve M Verrastroand F Favati ldquoImprovement of analytical methods for thedetermination of polyphenolic bioactive compounds in berryfruitsrdquo Journal of Chemistry vol 2015 Article ID 384051 6pages 2015

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[10] A Denny and J Buttriss ldquoPlant foods and health focuson plant bioactivesrdquo EU 6th Framework Food Quality andSafety Thematic Priority Contract FOOD-CT-2005-513944European Food Information Resource (EuroFIR) Consortium2007

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[12] D Zhao C Zhou Y Sheng G Liang and J Tao ldquoMolecularcloning and expression of phytoene synthase lycopene beta-cyclase and beta-carotene hydroxylase genes in persimmon(Diospyros kaki L) fruitsrdquo PlantMolecular Biology Reporter vol29 no 2 pp 345ndash351 2011

[13] K Suzuki S Tsubaki M Fujita N Koyama M Takahashiand K Takazawa ldquoEffects of safflower seed extract on arterialstiffnessrdquo Vascular Health and Risk Management vol 6 no 1pp 1007ndash1014 2010

[14] M S Butt and M T Sultan ldquoGreen tea naturersquos defense againstmalignanciesrdquo Critical Reviews in Food Science and Nutritionvol 49 no 5 pp 463ndash473 2009

[15] I Raskin D M Ribnicky S Komarnytsky et al ldquoPlants andhuman health in the twenty-first centuryrdquo Trends in Biotechnol-ogy vol 20 no 12 pp 522ndash531 2002

[16] S Parab R Kulkarni and U Thatte ldquoHeavy metals in herbalmedicinesrdquo Indian Journal of Gastroenterology vol 22 no 3 pp111ndash112 2003

[17] K L Miller R S Liebowitz and L K Newby ldquoComplementaryand alternative medicine in cardiovascular disease a review ofbiologically based approachesrdquoAmericanHeart Journal vol 147no 3 pp 401ndash411 2004

[18] D L Guo and Z R Luo ldquoGenetic relationships of the Japanesepersimmon Diospyros kaki (Ebenaceae) and related speciesrevealed by SSR analysisrdquo Genetics and Molecular Research vol10 no 2 pp 1060ndash1068 2011

[19] M J Li D Liang F Pu F W Ma C M Hou and T LuldquoAscorbate levels and the activity of key enzymes in ascorbatebiosynthesis and recycling in the leaves of 22 Chinese persim-mon cultivarsrdquo Scientia Horticulturae vol 120 no 2 pp 250ndash256 2009

[20] Z Luo ldquoEffect of 1-methylcyclopropene on ripening of posthar-vest persimmon (Diospyros kaki L) fruitrdquo LWTmdashFood Scienceand Technology vol 40 no 2 pp 285ndash291 2007

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[21] A T Oz ldquoCombined effects of 1-methyl cyclopropene (1-MCP)andmodified atmosphere packaging (MAP) on different ripen-ing stages of persimmon fruit during storagerdquo African Journalof Biotechnology vol 10 no 5 pp 807ndash814 2011

[22] M S Akter M Ahmed and J B Eun ldquoDietary fibre compo-nents antioxidant activities and hydration properties of ripepersimmon (Diospyros kaki L cv Daebong) peel powders asaffected by different washing treatmentsrdquo International Journalof Food Science and Technology vol 45 no 7 pp 1464ndash14712010

[23] K Yonemori A Sugiura andM Yamada ldquoPersimmon geneticsand breedingrdquo Plant Breeding Reviews vol 19 pp 191ndash225 2000

[24] P Thomas and T S Chen ldquoQuantitative analyses of majorcarotenoid fatty acid esters in fruits by liquid chromatographypersimmon and papayardquo Journal of Food Science vol 53 no 6pp 1720ndash1722 1988

[25] T Nakagawa A Nakatsuka K Yano et al ldquoExpressed sequencetags from persimmon at different developmental stagesrdquo PlantCell Reports vol 27 no 5 pp 931ndash938 2008

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[27] A Ikegami S Eguchi A Kitajima K Inoue and K YonemorildquoIdentification of genes involved in proanthocyanidin biosyn-thesis of persimmon (Diospyros kaki) fruitrdquo Plant Science vol172 no 5 pp 1037ndash1047 2007

[28] A Sattar N Bibi and M A Chaudry ldquoPhenolic compoundsin persimmon during maturation and on-tree ripeningrdquo Food Nahrung vol 36 no 5 pp 466ndash472 1992

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[30] A Ikegami T Akagi D Potter et al ldquoMolecular identifica-tion of 1-Cys peroxiredoxin and anthocyanidinflavonol 3-O-galactosyltransferase from proanthocyanidin-rich young fruitsof persimmon (Diospyros kakiThunb)rdquo Planta vol 230 no 4pp 841ndash855 2009

[31] T Radha and L Mathew Fruit Crops Horticulture ScienceSeries Jai Baharat Press 2007

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[33] X N Chen J F Fan X Yue X R Wu and L T Li ldquoRadicalscavenging activity and phenolic compounds in persimmon(Diospyros kaki L cv Mopan)rdquo Journal of Food Science vol 73no 1 pp C24ndashC28 2008

[34] H R Wang P Leng and C S Wang ldquoEffect of absorbentson storage quality of the Mopan persimmonrdquo Journal ShanxiAgriculture and Science vol 33 no 1 pp 59ndash61 2005

[35] X H Guo S Z Fang J Wang X X Guo L Q Xu and L YuanldquoStudy on the infection of the Mopan persimmon quality bycarbon dioxiderdquo Food Research Developments vol 27 pp 156ndash159 2006

[36] S Li P Zhang J K Li L Wang and Y F Huang ldquoEffect of1-methylcyclopropene for the Mopan persimmon crispiness-keeping under ambient temperaturerdquo Storing Process vol 6 pp13ndash16 2006

[37] J L Vazquez-Gutierrez I Hernando and A Quiles ldquoChangesin tannin solubility and microstructure of high hydrostaticpressurendashtreated persimmon cubes during storage at 4∘CrdquoEuropean Food Research and Technology vol 237 no 1 pp 9ndash172013

[38] N Bibi A B Khattak and ZMehmood ldquoQuality improvementand shelf life extension of persimmon fruit (Diospyros kaki)rdquoJournal of Food Engineering vol 79 no 4 pp 1359ndash1363 2007

[39] S Kondo H Yoshikawa and R Katayama ldquoAntioxidant activityin astringent and non-astringent persimmonsrdquo Journal of Hor-ticultural Science and Biotechnology vol 79 no 3 pp 390ndash3942004

[40] X Wei F Liu Z Qiu Y Shao and Y He ldquoRipeness classifica-tion of astringent persimmon using hyperspectral imagingtechniquerdquo Food and Bioprocess Technology vol 7 no 5 pp1371ndash1380 2014

[41] K P Wright and A A Kader ldquoEffect of controlled-atmospherestorage on the quality and carotenoid content of sliced persim-mons and peachesrdquo Postharvest Biology and Technology vol 10no 1 pp 89ndash97 1997

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2deastringency treatment on flesh disorders

induced by mechanical damage in persimmon Biochemicaland microstructural studiesrdquo Food Chemistry vol 145 pp 454ndash463 2014

[43] C J Xu and S L Zhang ldquoCarotenoid biosynthesis and its regu-lation in plantsrdquo Plant Physiology and Communication vol 36pp 64ndash70 2000

[44] E Bellini G Giannelli and E Picardi ldquoPanoramica varietaledel Kaki nel mondo e orientamenti produttivi per lrsquoItaliardquoLrsquoinformatore Agrario vol 44 no 47 pp 47ndash88 2011

[45] USDA-Agriculture Research Service National AgriculturalLibrary Beltsville Md USA vol 44 pp 47ndash88 1998

[46] M Kawase N Motohashi K Satoh et al ldquoBiological activityof persimmon (Diospyros kaki) peel extractsrdquo PhytotherapyResearch vol 17 no 5 pp 495ndash500 2003

[47] W Bei W Peng Y Ma and A Xu ldquoFlavonoids from the leavesof Diospyros kaki reduce hydrogen peroxide-induced injury ofNG108-15 cellsrdquo Life Sciences vol 76 no 17 pp 1975ndash1988 2005

[48] S-O Lee S-K Chung and I-S Lee ldquoThe antidiabetic effect ofdietary persimmon (Diospyros kaki L cv sangjudungsi) peel instreptozotocin-induced daibetic ratsrdquo Journal of Food Sciencevol 71 no 3 pp S293ndashS298 2006

[49] S Gorinstein Z Zachwieja M Folta et al ldquoComparative con-tents of dietary fiber total phenolics and minerals in persim-mons and applesrdquo Journal of Agricultural and Food Chemistryvol 49 no 2 pp 952ndash957 2001

[50] H Leontowicz S Gorinstein A Lojek et al ldquoComparativecontent of some bioactive compounds in apples peaches andpears and their influence on lipids and antioxidant capacity inratsrdquo Journal of Nutritional Biochemistry vol 13 no 10 pp 603ndash610 2002

[51] Y A Lee E J Cho and T Yokozawa ldquoProtective effect of per-simmon (Diospyros kaki) peel proanthocyanidin against oxida-tive damage under H

2O2-induced cellular senescencerdquo Biolog-

ical and Pharmaceutical Bulletin vol 31 no 6 pp 1265ndash12692008

[52] A Subagio N Morita and S Sawada ldquoCarotenoids and theirfatty-acid esters in banana peelrdquo Journal of Nutritional Scienceand Vitaminology vol 42 no 6 pp 553ndash566 1996

10 Journal of Chemistry

[53] Y J Yang and S J Kim ldquoChanges in chlorophyll and carotenoidcontents during cold and CA storage and characterization ofthe carotenoids in the peel of lsquoFujirsquo apple fruitrdquo Journal of KoreanSociety and Horticultural Science vol 36 pp 500ndash505 1995

[54] Y C Kim J B Kim K J Cho I S Lee and S K ChungldquoCarotenoid content of Korean persimmon peel and theirchanges in storagerdquo Food Science and Biotechnology vol 11 no5 pp 477ndash479 2002

[55] J Tous and L Ferguson ldquoMediterranean fruitsrdquo in Progress inNew Crops J Janick Ed pp 416ndash430 ASHS Press ArlingtonVa USA 1996

[56] B YuanH L Xu and S P Leng ldquoContent and chemical compo-sition of carotenoids in persimmon fruitrdquo Chinese AgriculturalScience Bulletin vol 22 pp 277ndash280 2006 (Chinese)

[57] D Zhao C Zhou and J Tao ldquoCarotenoid accumulation andcarotenogenic genes expression during two types of persimmonfruit (Diospyros kaki L) developmentrdquo Plant Molecular BiologyReporter vol 29 no 3 pp 646ndash654 2011

[58] L Plaza C Colina B D Ancos C Sanchez-Moreno and MPilar Cano ldquoInfluence of ripening and astringency on carote-noid content of high-pressure treated persimmon fruit (Dio-spyros kakiL)rdquo FoodChemistry vol 130 no 3 pp 591ndash597 2012

[59] T Niikawa T Suzuki T Ozeki M Kato and Y Ikoma ldquoChar-acteristics of carotenoid accumulation duringmaturation of theJapanese persimmon lsquoFuyursquordquo Horticultural Research vol 6 pp251ndash256 2007 (Japanese)

[60] G Britton ldquoStructure and properties of carotenoids in relationto functionrdquo The FASEB Journal vol 9 no 15 pp 1551ndash15581995

[61] H G Daood P Biacs B Czinkotai and A Hoschke ldquoChroma-tographic investigation of carotenoids sugars and organic acidsfrom Diospyros kaki fruitsrdquo Food Chemistry vol 45 no 2 pp151ndash155 1992

[62] I-C Jang E-K Jo S-M Bae et al ldquoAntioxidant activity andfatty acid composition of four different persimmon seedsrdquo FoodScience and Technology Research vol 16 no 6 pp 577ndash5842010

[63] J AMenendez L Vellon R Colomer and R Lupu ldquoOleic acidthe main monounsaturated fatty acid of olive oil suppressesHer-2neu (erbB-2) expression and synergistically enhances thegrowth inhibitory effects of trastuzumab (Herceptin) in breastcancer cells with Her-2neu oncogene amplificationrdquo Annals ofOncology vol 16 no 3 pp 359ndash371 2005

[64] W C Willett ldquoThe role of dietary n-6 fatty acids in theprevention of cardiovascular diseaserdquo Journal of CardiovascularMedicine vol 8 no 1 pp S42ndashS45 2007

[65] K Kawakami S Aketa H Sakai Y Watanabe H Nishida andM Hirayama ldquoAntihypertensive and vasorelaxant effects ofwater-soluble proanthocyanidins from persimmon leaf tea inspontaneously hypertensive ratsrdquo Bioscience Biotechnology andBiochemistry vol 75 no 8 pp 1435ndash1439 2011

[66] G Chen J Xue S-X Xu and R-Q Zhang ldquoChemical con-stituents of the leaves of Diospyros kaki and their cytotoxiceffectsrdquo Journal of Asian Natural Products Research vol 9 no4 pp 347ndash353 2007

[67] S Singh and H Joshi ldquoDiospyros kaki (Ebenaceae) a reviewrdquoAsian Journal of Research in Pharmaceutical Science vol 1 no3 pp 55ndash58 2011

[68] J L Navarro A Tarrega M A Sentandreu and E SentandreuldquoPartial purification and characterization of polyphenol oxi-dase from persimmonrdquo Food Chemistry vol 157 pp 283ndash2892014

[69] O V Zillich U Schweiggert-Weisz P Eisner and M KerscherldquoPolyphenols as active ingredients for cosmetic productsrdquoInternational Journal of Cosmetic Science vol 37 no 5 pp 455ndash464 2015

[70] H Palafox-Carlos J F Ayala-Zavala and G A Gonzalez-Aguilar ldquoThe role of dietary fiber in the bioaccessibility andbioavailability of fruit and vegetable antioxidantsrdquo Journal ofFood Science vol 76 no 1 pp R6ndashR15 2011

[71] A Ratz-Łyko J Arct SMajewski andK Pytkowska ldquoInfluenceof polyphenols on the physiological processes in the skinrdquoPhytotherapy Research vol 29 no 4 pp 509ndash517 2015

[72] J Sun Y-F Chu X Wu and R H Liu ldquoAntioxidant andantiproliferative activities of common fruitsrdquo Journal of Agricul-tural and Food Chemistry vol 50 no 25 pp 7449ndash7454 2002

[73] E Sentandreu M Cerdan-Calero J M Halket and J LNavarro ldquoRapid screening of low-molecular-weight phenolsfrom persimmon (Diospyros kaki) pulp using liquid chroma-tographyUVndashvisibleelectrospray mass spectrometry analysisrdquoJournal of the Science of Food and Agriculture vol 95 pp 1648ndash1654 2015

[74] L Bravo ldquoPolyphenols chemistry dietary sources metabolismand nutritional significancerdquo Nutrition Reviews vol 56 no 11pp 317ndash333 1998

[75] T Akagi Y Suzuki A Ikegami et al ldquoCondensed tannin com-position analysis in persimmon (Diospyros kakiThunb) fruit byacid catalysis in the presence of excess phloroglucinolrdquo Journalof the Japanese Society for Horticultural Science vol 79 no 3 pp275ndash281 2010

[76] C Li R Leverence J D Trombley et al ldquoHighmolecularweightpersimmon (Diospyros kaki L) proanthocyanidin a highlygalloylated a-linked tannin with an unusual flavonol terminalunitmyricetinrdquo Journal of Agricultural and FoodChemistry vol58 no 16 pp 9033ndash9042 2010

[77] C A Rice-Evans N J Miller and G Paganga ldquoStructure-antioxidant activity relationships of flavonoids and phenolicacidsrdquo Free Radical Biology andMedicine vol 20 no 7 pp 933ndash956 1996

[78] R Tsao ldquoChemistry and biochemistry of dietary polyphenolsrdquoNutrients vol 2 no 12 pp 1231ndash1246 2010

[79] S Uchida H Ohta R Edamatsu M Hiromatsu A Mori andG I Nomaka ldquoPersimmon tannin prolongs life span of stroke-prone spontaneously hypertensive rats (SHRSP) by acting as afree-radical scavengerrdquo in New Horizons in Preventing Cardio-vascular Diseases Y Yamori and T Strasser Eds pp 15ndash17Academic Press Amsterdam The Netherlands Elsevier NewYork NY USA 1989

[80] S Uchida H Ohta M Niwa et al ldquoProlongation of life spanof stroke-prone spontaneously hypertensive rats (SHRSP)ingesting persimmon tanninrdquo Chemical and PharmaceuticalBulletin vol 38 no 4 pp 1049ndash1052 1990

[81] S Gorinstein G W Kulasek E Bartnikowska et al ldquoThe influ-ence of persimmon peel and persimmon pulp on the lipidmeta-bolism and antioxidant activity of rats fed cholesterolrdquo Journalof Nutritional Biochemistry vol 9 no 4 pp 223ndash227 1998

[82] K Matsumoto A Kadowaki N Ozaki et al ldquoBile acid-bind-ing ability of kaki-tannin from young fruits of persimmon (Dio-spyros kaki) in vitro and in vivordquo Phytotherapy Research vol 25no 4 pp 624ndash628 2011

[83] K Ueda R Kawabata T Irie Y Nakai Y Tohya and T Sak-aguchi ldquoInactivation of pathogenic viruses by plant-derivedtannins strong effects of extracts from persimmon (Diospyros

Journal of Chemistry 11

kaki) on a broad range of virusesrdquo PLoS ONE vol 8 no 1Article ID e55343 10 pages 2013

[84] H Suzuki M Konishi M Kimura T Mori M Suzuki and TIkemi ldquoInhibitory effects ofDiospyros kakiTHUNB Extracts indental caries in ratsrdquo Japanese Journal of Conservative Dentistryvol 50 no 2 pp 140ndash145 2007

[85] S Sakanaka Y Tachibana and Y Okada ldquoPreparation andantioxidant properties of extracts of Japanese persimmon leaftea (Kakinoha-cha)rdquo Food Chemistry vol 89 no 4 pp 569ndash5752005

[86] MHosny and J PN Rosazza ldquoNovel oxidations of (+)-catechinby horseradish peroxidase and laccaserdquo Journal of Agriculturaland Food Chemistry vol 50 no 20 pp 5539ndash5545 2002

[87] J-I Inokuchi H Okabe T Yamauchi and A NagamatsuldquoInhibitors of angiotensin converting enzyme in crude drugsrdquoChemical and Pharmaceutical Bulletin vol 32 no 9 pp 3615ndash3619 1984

[88] Y Tian B Zou L Yang et al ldquoHigh molecular weight per-simmon tannin ameliorates cognition deficits and attenuatesoxidative damage in senescent mice induced by d-galactoserdquoFood andChemical Toxicology vol 49 no 8 pp 1728ndash1736 2011

[89] Y Achiwa H Hibasami H Katsuzaki K Imai and T KomiyaldquoInhibitory effects of persimmon (Diospyros kaki) extract andrelated polyphenol compounds on growth of human lymphoidleukemia cellsrdquo Bioscience Biotechnology and Biochemistry vol61 no 7 pp 1099ndash1101 1997

[90] J Gross Carotenoids vol 123 Academic Press New York NYUSA 1987

[91] B De Ancos E Gonzalez and M P Cano ldquoEffect of high-pressure treatment on the carotenoid composition and theradical scavenging activity of persimmon fruit pureesrdquo Journalof Agricultural and Food Chemistry vol 48 no 8 pp 3542ndash3548 2000

[92] T Matsuo and S Ito ldquoThe chemical structure of Kaki-tanninfrom immature fruit of the persimmon (Diospyros kaki L)rdquoAgricultural and Biological Chemistry vol 42 no 9 pp 1637ndash1643 1978

[93] S Gorinstein M Zemser M Weisz et al ldquoFluorometric anal-ysis of phenolics in persimmonsrdquo Bioscience Biotechnology andBiochemistry vol 58 no 6 pp 1087ndash1092 1994

[94] S O Lee H J LeeMH Yu H G Im and I S Lee ldquoTotal poly-phenol contents and antioxidant activities of methanol extractsfrom vegetables produced in Ullung Islandrdquo Korean Journal ofFood Science and Technology vol 37 no 2 pp 233ndash240 2005

[95] U V Mallavadhani A K Panda and Y R Rao ldquoPharmacologyand chemotaxonomy of Diospyrosrdquo Phytochemistry vol 49 no4 pp 901ndash951 1998

[96] G Block B Patterson and A Subar ldquoFruit vegetables andcancer prevention a review of the epidemiological evidencerdquoNutrition and Cancer vol 18 no 1 pp 1ndash29 1992

[97] G van Poppel ldquoCarotenoids and cancer an updatewith empha-sis on human intervention studiesrdquo European Journal of Cancervol 29 no 9 pp 1335ndash1344 1993

[98] E Giovannucci A Ascherio E B Rimm M J Stampfer G AColditz and W C Willett ldquoIntake of carotenoids and retino inrelation to risk of prostate cancerrdquo Journal of theNational CancerInstitute vol 87 no 23 pp 1767ndash1776 1995

[99] T Johns R L A Mahunnah P Sanaya L Chapman and TTicktin ldquoSaponins and phenolic content in plant dietary addi-tives of a traditional subsistence community the Batemi ofNgorongoro District Tanzaniardquo Journal of Ethnopharmacologyvol 66 no 1 pp 1ndash10 1999

[100] Y Zhang X Lu Y Zhang L Qin and J Zhang ldquoSulfatedmodification and immunomodulatory activity of water-solublepolysaccharides derived from fresh Chinese persimmon fruitrdquoInternational Journal of Biological Macromolecules vol 46 no1 pp 67ndash71 2010

[101] Y-J Moon and Y-S Cha ldquoEffects of persimmon-vinegar onlipid metabolism and alcohol clearance in chronic alcohol-fedratsrdquo Journal of Medicinal Food vol 11 no 1 pp 38ndash45 2008

[102] H S Ahn T I Jeon J Y Lee S G Hwang Y Lim and D KPark ldquoAntioxidative activity of persimmon and grape seedextract in vitro and in vivordquo Nutrition Research vol 22 no 11pp 1265ndash1273 2002

[103] H Itamurah N Murakami and H Nagamatsu ldquoProperty ofkaki-tannin as a functional composition in persimmon fruitflesh and leaves and its solubility in artificial stomach liquidrdquoin Proceedings of the 27th International Horticultural Congressamp Exhibition (IHC rsquo06) vol 8 pp 265ndash267 August 2006

[104] K A Steinmetz and J D Potter ldquoVegetables fruit and cancerprevention a reviewrdquo Journal of the American Dietetic Associa-tion vol 96 no 10 pp 1027ndash1039 1996

[105] A N Nagappa P A Thakurdesai N V Rao and J SinghldquoAntidiabetic activity ofTerminalia catappa Linn fruitsrdquo Journalof Ethnopharmacology vol 88 no 1 pp 45ndash50 2003

[106] K Datta S Sinha and P Chattopadhyay ldquoReactive oxygenspecies in health and diseaserdquoNationalMedical Journal of Indiavol 13 no 6 pp 304ndash310 2000

[107] R R Holman and R C Turner ldquoOral agents and insulin in thetreatment of NIDDMrdquo in Textbook of Diabetes J Williams Edpp 407ndash469 Blackwell Press Oxford UK 1991

[108] F Giacco and M Brownlee ldquoOxidative stress and diabeticcomplicationsrdquo Circulation Research vol 107 no 9 pp 1058ndash1070 2010

[109] B K Rao M M Kesavulu R Giri and C A Rao ldquoAntidiabeticand hypolipidemic effects ofMomordicacymbalariaHook fruitpowder in alloxan-diabetic ratsrdquo Journal of Ethnopharmacologyvol 67 no 1 pp 103ndash109 1999

[110] J K Grover V Vats V Rathi and S S Dawar ldquoTraditionalIndian anti-diabetic plants attenuate progression of renal dam-age in streptozotocin induced diabetic micerdquo Journal of Ethno-pharmacology vol 76 no 3 pp 233ndash238 2001

[111] R K Gupta A N Kesari P S Murthy R Chandra V Tandonand GWatal ldquoHypoglycemic and antidiabetic effect of ethano-lic extract of leaves of Annona squamosa L in experimentalanimalsrdquo Journal of Ethnopharmacology vol 99 no 1 pp 75ndash81 2005

[112] S Gupta N Ahmad A-L Nieminen andHMukhtar ldquoGrowthinhibition cell-cycle dysregulation and induction of apopto-sis by green tea constituent (-)-epigallocatechin-3-gallate inandrogen-sensitive and androgen-insensitive human prostatecarcinoma cellsrdquoToxicology andApplied Pharmacology vol 164no 1 pp 82ndash90 2000

[113] T Yokozawa Y A Kim H Y Kim Y A Lee and G-I NonakaldquoProtective effect of persimmon peel polyphenol against highglucose-induced oxidative stress in LLC-PK1 cellsrdquo Food andChemical Toxicology vol 45 no 10 pp 1979ndash1987 2007

12 Journal of Chemistry

[114] M S Brewer ldquoNatural antioxidants sources compoundsmechanisms of action and potential applicationsrdquo Comprehen-sive Reviews in Food Science and Food Safety vol 10 no 4 pp221ndash247 2011

[115] K Kawakami H Nishida N Tatewaki Y Nakajima T Konishiand M Hirayama ldquoPersimmon leaf extract inhibits the ATMactivity during DNA damage response induced by Doxorubicinin A549 lung adenocarcinoma cellsrdquo Bioscience Biotechnologyand Biochemistry vol 75 no 4 pp 650ndash655 2011

[116] D Steinberg S Parthasarathy T E Carew J C Khoo and JL Witztum ldquoBeyond cholesterol modifications of low-densitylipoprotein that increase its atherogenicityrdquo The New EnglandJournal of Medicine vol 320 no 14 pp 915ndash924 1989

[117] P M Kris-Etherton and C L Keen ldquoEvidence that the anti-oxidant flavonoids in tea and cocoa are beneficial for cardiovas-cular healthrdquo Current Opinion in Lipidology vol 13 no 1 pp41ndash49 2002

[118] C Manach A Mazur and A Scalbert ldquoPolyphenols and pre-vention of cardiovascular diseasesrdquo Current Opinion in Lipidol-ogy vol 16 no 1 pp 77ndash84 2005

[119] J W Anderson B M Smith and N J Gustafson ldquoHealthbenefits and practical aspects of high-fiber dietsrdquo AmericanJournal of Clinical Nutrition vol 59 no 5 pp 1242ndash1247 1994

[120] D Kromhout A Menotti H Kesteloot and S Sans ldquoPreven-tion of coronary heart disease by diet and lifestyle evidencefrom prospective cross-cultural cohort and intervention stud-iesrdquo Circulation vol 105 no 7 pp 893ndash898 2002

[121] E B Rimm M J Stampfer A Ascherio E Giovannucci G AColditz andWCWillett ldquoVitamin E consumption and the riskof coronary heart disease in menrdquo The New England Journal ofMedicine vol 328 no 20 pp 1450ndash1456 1993

[122] L Dauchet J Ferrieres D Arveiler et al ldquoFrequency of fruitand vegetable consumption and coronary heart disease inFrance and Northern Ireland the prime studyrdquo British Journalof Nutrition vol 92 no 6 pp 963ndash972 2004

[123] S Gorinstein GW Kulasek E Bartnikowska et al ldquoThe effectsof diets supplementedwith either whole persimmon or phenol-free persimmon on rats fed cholesterolrdquo Food Chemistry vol70 no 3 pp 303ndash308 2000

[124] M G L Hertog E J M Feskens P C H HollmanM B Katanand D Kromhout ldquoDietary antioxidant flavonoids and risk ofcoronary heart disease the Zutphen Elderly studyrdquoThe Lancetvol 342 no 8878 pp 1007ndash1011 1993

[125] H Seo B D Jeon andR Sungpil ldquoPersimmon vinegar ripeningwith the mountain-cultivated ginseng ingestion reduces bloodlipids and lowers inflammatory cytokines in obese adolescentsrdquoJournal of Exercise Nutrition and Biochemistry vol 19 no 1 pp1ndash10 2015

[126] R H Liu ldquoPotential synergy of phytochemicals in cancerprevention mechanism of actionrdquo Journal of Nutrition vol 134no 12 supplement pp 3479Sndash3485S 2004

[127] S T Mayne ldquoAntioxidant nutrients and chronic disease use ofbiomarkers of exposure and oxidative stress status in epidemi-ologic researchrdquo Journal of Nutrition vol 133 no 3 pp 933sndash940s 2003

[128] H Tapiero D M Townsend and K D Tew ldquoThe role of caro-tenoids in the prevention of human pathologiesrdquo Biomedicineand Pharmacotherapy vol 58 no 2 pp 100ndash110 2004

[129] J Tao and S L Zhang ldquoMetabolismof carotenoid and its regula-tion in garden croprdquo Journal of Zhejiang University (Agricultureamp Life Sciences) vol 29 pp 585ndash590 2003

[130] W Miki ldquoBiological functions and activities of animal caro-tenoidsrdquo Pure and Applied Chemistry vol 63 no 1 pp 141ndash1461991

[131] H Fujiki ldquoGreen tea health benefits as cancer preventive forhumansrdquo Chemical Record vol 5 no 3 pp 119ndash132 2005

[132] A P George and S Redpath ldquoHealth and medicinal benefits ofpersimmon fruit a reviewrdquo Advances in Horticultural Sciencevol 22 no 4 pp 244ndash249 2008

[133] T Hussain S Gupta V M Adhami and H Mukhtar ldquoGreentea constituent epigallocatechin-3-gallate selectively inhibitsCOX-2 without affecting COX-1 expression in human prostatecarcinoma cellsrdquo International Journal of Cancer vol 113 no 4pp 660ndash669 2005

[134] Y-C Wang and U Bachrach ldquoThe specific anti-cancer activityof green tea (minus)-epigallocatechin-3-gallate (EGCG)rdquo AminoAcids vol 22 no 2 pp 131ndash143 2002

[135] O Takayuki ldquoPersimmons your healthy autumn treatsrdquoAsahikawa Information vol 108 pp 1ndash2 2005

[136] T Fukuda and H Shibata ldquoPersimmon calyx extracts as anti-convulsants and to alleviate the side effects of barbituric acidcompoundsrdquo Patent Japanease Kokai Tokkyo Koho vol 6 pp649ndash653 1994

[137] T Matsuno ldquoXanthophylls as precursors of retinoidsrdquo Pure andApplied Chemistry vol 63 no 1 pp 81ndash88 1991

[138] N Gato A Kadowaki N Hashimoto S-I Yokoyama and KMatsumoto ldquoPersimmon fruit tannin-rich fiber reduces choles-terol levels in humansrdquoAnnals of Nutrition andMetabolism vol62 no 1 pp 1ndash6 2013

[139] A Nagao ldquoAbsorption and function of dietary carotenoidsrdquoForum of Nutrition vol 61 pp 55ndash63 2009

[140] PD Fraser andPM Bramley ldquoThebiosynthesis andnutritionaluses of carotenoidsrdquo Progress in Lipid Research vol 43 no 3 pp228ndash265 2004

[141] D Fusco G Colloca M R Lo Monaco and M Cesari ldquoEffectsof antioxidant supplementation on the aging processrdquo ClinicalInterventions in Aging vol 2 no 3 pp 377ndash387 2007

[142] JM Seddon U Ajan and R D Sperduto ldquoDietary carotenoidsvitamins A C and E and advance age-related macular degen-eration Eye Disease Case Study Grouprdquo Journal of AmericanMedical Association vol 272 no 18 pp 1413ndash1420 1992

[143] B-J An J-H Kwak J-M Park et al ldquoInhibition of enzymeactivities and the antiwrinkle effect of polyphenol isolated fromthe persimmon leaf (Diospyros kaki folium) on human skinrdquoDermatologic Surgery vol 31 no 7 pp 848ndash854 2005

[144] H Arakawa M Takasaki N Tajima H Fukamachi and TIgarashi ldquoAntibacterial activities of persimmon extracts relatewith their hydrogen peroxide concentrationrdquo Biological andPharmaceutical Bulletin vol 37 no 7 pp 1119ndash1123 2014

[145] S D Ladas D Kamberoglou G Karamanolis J Vlachogian-nakos and I Zouboulis-Vafiadis ldquoSystematic review Coca-Cola can effectively dissolve gastric phytobezoars as a first-linetreatmentrdquo Alimentary Pharmacology and Therapeutics vol 37no 2 pp 169ndash173 2013

[146] T J Cifuentes C R Robles P P Parrilla et al ldquoPolyphenols andhealth what compounds are involvedrdquo Nutrition Metabolismand Cardiovascular Diseases vol 20 no 1 pp 1ndash6 2010

[147] J Gaya L Barranco A Llompart J Reyes and A ObradorldquoPersimmon bezoars a successful combined therapyrdquoGastroin-testinal Endoscopy vol 55 no 4 pp 581ndash583 2002

[148] P G Hayes and O D Rotstein ldquoGastrointestinal phytobezoarspresentation and managementrdquo Canadian Journal of Surgeryvol 29 no 6 pp 419ndash420 1986

Journal of Chemistry 13

[149] MM Krausz E ZMoriel A Ayalon D Pode and A L DurstldquoSurgical aspects of gastrointestinal persimmon phytobezoartreatmentrdquoThe American Journal of Surgery vol 152 no 5 pp526ndash530 1986

[150] P Walker-Renard ldquoUpdate on the medicinal management ofphytobezoarsrdquo The American Journal of Gastroenterology vol88 no 10 pp 1663ndash1666 1993

[151] S S Ha H S LeeM K Jung et al ldquoAcute intestinal obstructioncaused by a persimmon phytobezoar after dissolution therapywith Coca-Colardquo The Korean Journal of Internal Medicine vol22 no 4 pp 300ndash303 2007

[152] J Han S Kang R Choue et al ldquoFree radical scavenging effectofDiospyros kaki Laminaria japonica andUndaria pinnatifidardquoFitoterapia vol 73 no 7-8 pp 710ndash712 2002

Submit your manuscripts athttpwwwhindawicom

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Inorganic ChemistryInternational Journal of

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Carbohydrate Chemistry

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Page 9: Review Article Chemistry and Functionality of Bioactive ...downloads.hindawi.com/journals/jchem/2016/3424025.pdf · Review Article Chemistry and Functionality of Bioactive Compounds

Journal of Chemistry 9

[21] A T Oz ldquoCombined effects of 1-methyl cyclopropene (1-MCP)andmodified atmosphere packaging (MAP) on different ripen-ing stages of persimmon fruit during storagerdquo African Journalof Biotechnology vol 10 no 5 pp 807ndash814 2011

[22] M S Akter M Ahmed and J B Eun ldquoDietary fibre compo-nents antioxidant activities and hydration properties of ripepersimmon (Diospyros kaki L cv Daebong) peel powders asaffected by different washing treatmentsrdquo International Journalof Food Science and Technology vol 45 no 7 pp 1464ndash14712010

[23] K Yonemori A Sugiura andM Yamada ldquoPersimmon geneticsand breedingrdquo Plant Breeding Reviews vol 19 pp 191ndash225 2000

[24] P Thomas and T S Chen ldquoQuantitative analyses of majorcarotenoid fatty acid esters in fruits by liquid chromatographypersimmon and papayardquo Journal of Food Science vol 53 no 6pp 1720ndash1722 1988

[25] T Nakagawa A Nakatsuka K Yano et al ldquoExpressed sequencetags from persimmon at different developmental stagesrdquo PlantCell Reports vol 27 no 5 pp 931ndash938 2008

[26] R Veberic J Jurhar M Mikulic-Petkovsek F Stampar andV Schmitzer ldquoComparative study of primary and secondarymetabolites in 11 cultivars of persimmon fruit (Diospyros kakiL)rdquo Food Chemistry vol 119 no 2 pp 477ndash483 2010

[27] A Ikegami S Eguchi A Kitajima K Inoue and K YonemorildquoIdentification of genes involved in proanthocyanidin biosyn-thesis of persimmon (Diospyros kaki) fruitrdquo Plant Science vol172 no 5 pp 1037ndash1047 2007

[28] A Sattar N Bibi and M A Chaudry ldquoPhenolic compoundsin persimmon during maturation and on-tree ripeningrdquo Food Nahrung vol 36 no 5 pp 466ndash472 1992

[29] Y-S Park S-T Jung S-G Kang et al ldquoDrying of persimmons(Diospyros kaki L) and the following changes in the studiedbioactive compounds and the total radical scavenging activi-tiesrdquo LWTmdashFood Science and Technology vol 39 no 7 pp 748ndash755 2006

[30] A Ikegami T Akagi D Potter et al ldquoMolecular identifica-tion of 1-Cys peroxiredoxin and anthocyanidinflavonol 3-O-galactosyltransferase from proanthocyanidin-rich young fruitsof persimmon (Diospyros kakiThunb)rdquo Planta vol 230 no 4pp 841ndash855 2009

[31] T Radha and L Mathew Fruit Crops Horticulture ScienceSeries Jai Baharat Press 2007

[32] H Yakushiji ldquoRecent persimmon research in Japanrdquo JapaneseJournal of Plant Science vol 1 pp 42ndash62 2007

[33] X N Chen J F Fan X Yue X R Wu and L T Li ldquoRadicalscavenging activity and phenolic compounds in persimmon(Diospyros kaki L cv Mopan)rdquo Journal of Food Science vol 73no 1 pp C24ndashC28 2008

[34] H R Wang P Leng and C S Wang ldquoEffect of absorbentson storage quality of the Mopan persimmonrdquo Journal ShanxiAgriculture and Science vol 33 no 1 pp 59ndash61 2005

[35] X H Guo S Z Fang J Wang X X Guo L Q Xu and L YuanldquoStudy on the infection of the Mopan persimmon quality bycarbon dioxiderdquo Food Research Developments vol 27 pp 156ndash159 2006

[36] S Li P Zhang J K Li L Wang and Y F Huang ldquoEffect of1-methylcyclopropene for the Mopan persimmon crispiness-keeping under ambient temperaturerdquo Storing Process vol 6 pp13ndash16 2006

[37] J L Vazquez-Gutierrez I Hernando and A Quiles ldquoChangesin tannin solubility and microstructure of high hydrostaticpressurendashtreated persimmon cubes during storage at 4∘CrdquoEuropean Food Research and Technology vol 237 no 1 pp 9ndash172013

[38] N Bibi A B Khattak and ZMehmood ldquoQuality improvementand shelf life extension of persimmon fruit (Diospyros kaki)rdquoJournal of Food Engineering vol 79 no 4 pp 1359ndash1363 2007

[39] S Kondo H Yoshikawa and R Katayama ldquoAntioxidant activityin astringent and non-astringent persimmonsrdquo Journal of Hor-ticultural Science and Biotechnology vol 79 no 3 pp 390ndash3942004

[40] X Wei F Liu Z Qiu Y Shao and Y He ldquoRipeness classifica-tion of astringent persimmon using hyperspectral imagingtechniquerdquo Food and Bioprocess Technology vol 7 no 5 pp1371ndash1380 2014

[41] K P Wright and A A Kader ldquoEffect of controlled-atmospherestorage on the quality and carotenoid content of sliced persim-mons and peachesrdquo Postharvest Biology and Technology vol 10no 1 pp 89ndash97 1997

[42] P Novillo A Salvador E Llorca I Hernando and C BesadaldquoEffect of CO

2deastringency treatment on flesh disorders

induced by mechanical damage in persimmon Biochemicaland microstructural studiesrdquo Food Chemistry vol 145 pp 454ndash463 2014

[43] C J Xu and S L Zhang ldquoCarotenoid biosynthesis and its regu-lation in plantsrdquo Plant Physiology and Communication vol 36pp 64ndash70 2000

[44] E Bellini G Giannelli and E Picardi ldquoPanoramica varietaledel Kaki nel mondo e orientamenti produttivi per lrsquoItaliardquoLrsquoinformatore Agrario vol 44 no 47 pp 47ndash88 2011

[45] USDA-Agriculture Research Service National AgriculturalLibrary Beltsville Md USA vol 44 pp 47ndash88 1998

[46] M Kawase N Motohashi K Satoh et al ldquoBiological activityof persimmon (Diospyros kaki) peel extractsrdquo PhytotherapyResearch vol 17 no 5 pp 495ndash500 2003

[47] W Bei W Peng Y Ma and A Xu ldquoFlavonoids from the leavesof Diospyros kaki reduce hydrogen peroxide-induced injury ofNG108-15 cellsrdquo Life Sciences vol 76 no 17 pp 1975ndash1988 2005

[48] S-O Lee S-K Chung and I-S Lee ldquoThe antidiabetic effect ofdietary persimmon (Diospyros kaki L cv sangjudungsi) peel instreptozotocin-induced daibetic ratsrdquo Journal of Food Sciencevol 71 no 3 pp S293ndashS298 2006

[49] S Gorinstein Z Zachwieja M Folta et al ldquoComparative con-tents of dietary fiber total phenolics and minerals in persim-mons and applesrdquo Journal of Agricultural and Food Chemistryvol 49 no 2 pp 952ndash957 2001

[50] H Leontowicz S Gorinstein A Lojek et al ldquoComparativecontent of some bioactive compounds in apples peaches andpears and their influence on lipids and antioxidant capacity inratsrdquo Journal of Nutritional Biochemistry vol 13 no 10 pp 603ndash610 2002

[51] Y A Lee E J Cho and T Yokozawa ldquoProtective effect of per-simmon (Diospyros kaki) peel proanthocyanidin against oxida-tive damage under H

2O2-induced cellular senescencerdquo Biolog-

ical and Pharmaceutical Bulletin vol 31 no 6 pp 1265ndash12692008

[52] A Subagio N Morita and S Sawada ldquoCarotenoids and theirfatty-acid esters in banana peelrdquo Journal of Nutritional Scienceand Vitaminology vol 42 no 6 pp 553ndash566 1996

10 Journal of Chemistry

[53] Y J Yang and S J Kim ldquoChanges in chlorophyll and carotenoidcontents during cold and CA storage and characterization ofthe carotenoids in the peel of lsquoFujirsquo apple fruitrdquo Journal of KoreanSociety and Horticultural Science vol 36 pp 500ndash505 1995

[54] Y C Kim J B Kim K J Cho I S Lee and S K ChungldquoCarotenoid content of Korean persimmon peel and theirchanges in storagerdquo Food Science and Biotechnology vol 11 no5 pp 477ndash479 2002

[55] J Tous and L Ferguson ldquoMediterranean fruitsrdquo in Progress inNew Crops J Janick Ed pp 416ndash430 ASHS Press ArlingtonVa USA 1996

[56] B YuanH L Xu and S P Leng ldquoContent and chemical compo-sition of carotenoids in persimmon fruitrdquo Chinese AgriculturalScience Bulletin vol 22 pp 277ndash280 2006 (Chinese)

[57] D Zhao C Zhou and J Tao ldquoCarotenoid accumulation andcarotenogenic genes expression during two types of persimmonfruit (Diospyros kaki L) developmentrdquo Plant Molecular BiologyReporter vol 29 no 3 pp 646ndash654 2011

[58] L Plaza C Colina B D Ancos C Sanchez-Moreno and MPilar Cano ldquoInfluence of ripening and astringency on carote-noid content of high-pressure treated persimmon fruit (Dio-spyros kakiL)rdquo FoodChemistry vol 130 no 3 pp 591ndash597 2012

[59] T Niikawa T Suzuki T Ozeki M Kato and Y Ikoma ldquoChar-acteristics of carotenoid accumulation duringmaturation of theJapanese persimmon lsquoFuyursquordquo Horticultural Research vol 6 pp251ndash256 2007 (Japanese)

[60] G Britton ldquoStructure and properties of carotenoids in relationto functionrdquo The FASEB Journal vol 9 no 15 pp 1551ndash15581995

[61] H G Daood P Biacs B Czinkotai and A Hoschke ldquoChroma-tographic investigation of carotenoids sugars and organic acidsfrom Diospyros kaki fruitsrdquo Food Chemistry vol 45 no 2 pp151ndash155 1992

[62] I-C Jang E-K Jo S-M Bae et al ldquoAntioxidant activity andfatty acid composition of four different persimmon seedsrdquo FoodScience and Technology Research vol 16 no 6 pp 577ndash5842010

[63] J AMenendez L Vellon R Colomer and R Lupu ldquoOleic acidthe main monounsaturated fatty acid of olive oil suppressesHer-2neu (erbB-2) expression and synergistically enhances thegrowth inhibitory effects of trastuzumab (Herceptin) in breastcancer cells with Her-2neu oncogene amplificationrdquo Annals ofOncology vol 16 no 3 pp 359ndash371 2005

[64] W C Willett ldquoThe role of dietary n-6 fatty acids in theprevention of cardiovascular diseaserdquo Journal of CardiovascularMedicine vol 8 no 1 pp S42ndashS45 2007

[65] K Kawakami S Aketa H Sakai Y Watanabe H Nishida andM Hirayama ldquoAntihypertensive and vasorelaxant effects ofwater-soluble proanthocyanidins from persimmon leaf tea inspontaneously hypertensive ratsrdquo Bioscience Biotechnology andBiochemistry vol 75 no 8 pp 1435ndash1439 2011

[66] G Chen J Xue S-X Xu and R-Q Zhang ldquoChemical con-stituents of the leaves of Diospyros kaki and their cytotoxiceffectsrdquo Journal of Asian Natural Products Research vol 9 no4 pp 347ndash353 2007

[67] S Singh and H Joshi ldquoDiospyros kaki (Ebenaceae) a reviewrdquoAsian Journal of Research in Pharmaceutical Science vol 1 no3 pp 55ndash58 2011

[68] J L Navarro A Tarrega M A Sentandreu and E SentandreuldquoPartial purification and characterization of polyphenol oxi-dase from persimmonrdquo Food Chemistry vol 157 pp 283ndash2892014

[69] O V Zillich U Schweiggert-Weisz P Eisner and M KerscherldquoPolyphenols as active ingredients for cosmetic productsrdquoInternational Journal of Cosmetic Science vol 37 no 5 pp 455ndash464 2015

[70] H Palafox-Carlos J F Ayala-Zavala and G A Gonzalez-Aguilar ldquoThe role of dietary fiber in the bioaccessibility andbioavailability of fruit and vegetable antioxidantsrdquo Journal ofFood Science vol 76 no 1 pp R6ndashR15 2011

[71] A Ratz-Łyko J Arct SMajewski andK Pytkowska ldquoInfluenceof polyphenols on the physiological processes in the skinrdquoPhytotherapy Research vol 29 no 4 pp 509ndash517 2015

[72] J Sun Y-F Chu X Wu and R H Liu ldquoAntioxidant andantiproliferative activities of common fruitsrdquo Journal of Agricul-tural and Food Chemistry vol 50 no 25 pp 7449ndash7454 2002

[73] E Sentandreu M Cerdan-Calero J M Halket and J LNavarro ldquoRapid screening of low-molecular-weight phenolsfrom persimmon (Diospyros kaki) pulp using liquid chroma-tographyUVndashvisibleelectrospray mass spectrometry analysisrdquoJournal of the Science of Food and Agriculture vol 95 pp 1648ndash1654 2015

[74] L Bravo ldquoPolyphenols chemistry dietary sources metabolismand nutritional significancerdquo Nutrition Reviews vol 56 no 11pp 317ndash333 1998

[75] T Akagi Y Suzuki A Ikegami et al ldquoCondensed tannin com-position analysis in persimmon (Diospyros kakiThunb) fruit byacid catalysis in the presence of excess phloroglucinolrdquo Journalof the Japanese Society for Horticultural Science vol 79 no 3 pp275ndash281 2010

[76] C Li R Leverence J D Trombley et al ldquoHighmolecularweightpersimmon (Diospyros kaki L) proanthocyanidin a highlygalloylated a-linked tannin with an unusual flavonol terminalunitmyricetinrdquo Journal of Agricultural and FoodChemistry vol58 no 16 pp 9033ndash9042 2010

[77] C A Rice-Evans N J Miller and G Paganga ldquoStructure-antioxidant activity relationships of flavonoids and phenolicacidsrdquo Free Radical Biology andMedicine vol 20 no 7 pp 933ndash956 1996

[78] R Tsao ldquoChemistry and biochemistry of dietary polyphenolsrdquoNutrients vol 2 no 12 pp 1231ndash1246 2010

[79] S Uchida H Ohta R Edamatsu M Hiromatsu A Mori andG I Nomaka ldquoPersimmon tannin prolongs life span of stroke-prone spontaneously hypertensive rats (SHRSP) by acting as afree-radical scavengerrdquo in New Horizons in Preventing Cardio-vascular Diseases Y Yamori and T Strasser Eds pp 15ndash17Academic Press Amsterdam The Netherlands Elsevier NewYork NY USA 1989

[80] S Uchida H Ohta M Niwa et al ldquoProlongation of life spanof stroke-prone spontaneously hypertensive rats (SHRSP)ingesting persimmon tanninrdquo Chemical and PharmaceuticalBulletin vol 38 no 4 pp 1049ndash1052 1990

[81] S Gorinstein G W Kulasek E Bartnikowska et al ldquoThe influ-ence of persimmon peel and persimmon pulp on the lipidmeta-bolism and antioxidant activity of rats fed cholesterolrdquo Journalof Nutritional Biochemistry vol 9 no 4 pp 223ndash227 1998

[82] K Matsumoto A Kadowaki N Ozaki et al ldquoBile acid-bind-ing ability of kaki-tannin from young fruits of persimmon (Dio-spyros kaki) in vitro and in vivordquo Phytotherapy Research vol 25no 4 pp 624ndash628 2011

[83] K Ueda R Kawabata T Irie Y Nakai Y Tohya and T Sak-aguchi ldquoInactivation of pathogenic viruses by plant-derivedtannins strong effects of extracts from persimmon (Diospyros

Journal of Chemistry 11

kaki) on a broad range of virusesrdquo PLoS ONE vol 8 no 1Article ID e55343 10 pages 2013

[84] H Suzuki M Konishi M Kimura T Mori M Suzuki and TIkemi ldquoInhibitory effects ofDiospyros kakiTHUNB Extracts indental caries in ratsrdquo Japanese Journal of Conservative Dentistryvol 50 no 2 pp 140ndash145 2007

[85] S Sakanaka Y Tachibana and Y Okada ldquoPreparation andantioxidant properties of extracts of Japanese persimmon leaftea (Kakinoha-cha)rdquo Food Chemistry vol 89 no 4 pp 569ndash5752005

[86] MHosny and J PN Rosazza ldquoNovel oxidations of (+)-catechinby horseradish peroxidase and laccaserdquo Journal of Agriculturaland Food Chemistry vol 50 no 20 pp 5539ndash5545 2002

[87] J-I Inokuchi H Okabe T Yamauchi and A NagamatsuldquoInhibitors of angiotensin converting enzyme in crude drugsrdquoChemical and Pharmaceutical Bulletin vol 32 no 9 pp 3615ndash3619 1984

[88] Y Tian B Zou L Yang et al ldquoHigh molecular weight per-simmon tannin ameliorates cognition deficits and attenuatesoxidative damage in senescent mice induced by d-galactoserdquoFood andChemical Toxicology vol 49 no 8 pp 1728ndash1736 2011

[89] Y Achiwa H Hibasami H Katsuzaki K Imai and T KomiyaldquoInhibitory effects of persimmon (Diospyros kaki) extract andrelated polyphenol compounds on growth of human lymphoidleukemia cellsrdquo Bioscience Biotechnology and Biochemistry vol61 no 7 pp 1099ndash1101 1997

[90] J Gross Carotenoids vol 123 Academic Press New York NYUSA 1987

[91] B De Ancos E Gonzalez and M P Cano ldquoEffect of high-pressure treatment on the carotenoid composition and theradical scavenging activity of persimmon fruit pureesrdquo Journalof Agricultural and Food Chemistry vol 48 no 8 pp 3542ndash3548 2000

[92] T Matsuo and S Ito ldquoThe chemical structure of Kaki-tanninfrom immature fruit of the persimmon (Diospyros kaki L)rdquoAgricultural and Biological Chemistry vol 42 no 9 pp 1637ndash1643 1978

[93] S Gorinstein M Zemser M Weisz et al ldquoFluorometric anal-ysis of phenolics in persimmonsrdquo Bioscience Biotechnology andBiochemistry vol 58 no 6 pp 1087ndash1092 1994

[94] S O Lee H J LeeMH Yu H G Im and I S Lee ldquoTotal poly-phenol contents and antioxidant activities of methanol extractsfrom vegetables produced in Ullung Islandrdquo Korean Journal ofFood Science and Technology vol 37 no 2 pp 233ndash240 2005

[95] U V Mallavadhani A K Panda and Y R Rao ldquoPharmacologyand chemotaxonomy of Diospyrosrdquo Phytochemistry vol 49 no4 pp 901ndash951 1998

[96] G Block B Patterson and A Subar ldquoFruit vegetables andcancer prevention a review of the epidemiological evidencerdquoNutrition and Cancer vol 18 no 1 pp 1ndash29 1992

[97] G van Poppel ldquoCarotenoids and cancer an updatewith empha-sis on human intervention studiesrdquo European Journal of Cancervol 29 no 9 pp 1335ndash1344 1993

[98] E Giovannucci A Ascherio E B Rimm M J Stampfer G AColditz and W C Willett ldquoIntake of carotenoids and retino inrelation to risk of prostate cancerrdquo Journal of theNational CancerInstitute vol 87 no 23 pp 1767ndash1776 1995

[99] T Johns R L A Mahunnah P Sanaya L Chapman and TTicktin ldquoSaponins and phenolic content in plant dietary addi-tives of a traditional subsistence community the Batemi ofNgorongoro District Tanzaniardquo Journal of Ethnopharmacologyvol 66 no 1 pp 1ndash10 1999

[100] Y Zhang X Lu Y Zhang L Qin and J Zhang ldquoSulfatedmodification and immunomodulatory activity of water-solublepolysaccharides derived from fresh Chinese persimmon fruitrdquoInternational Journal of Biological Macromolecules vol 46 no1 pp 67ndash71 2010

[101] Y-J Moon and Y-S Cha ldquoEffects of persimmon-vinegar onlipid metabolism and alcohol clearance in chronic alcohol-fedratsrdquo Journal of Medicinal Food vol 11 no 1 pp 38ndash45 2008

[102] H S Ahn T I Jeon J Y Lee S G Hwang Y Lim and D KPark ldquoAntioxidative activity of persimmon and grape seedextract in vitro and in vivordquo Nutrition Research vol 22 no 11pp 1265ndash1273 2002

[103] H Itamurah N Murakami and H Nagamatsu ldquoProperty ofkaki-tannin as a functional composition in persimmon fruitflesh and leaves and its solubility in artificial stomach liquidrdquoin Proceedings of the 27th International Horticultural Congressamp Exhibition (IHC rsquo06) vol 8 pp 265ndash267 August 2006

[104] K A Steinmetz and J D Potter ldquoVegetables fruit and cancerprevention a reviewrdquo Journal of the American Dietetic Associa-tion vol 96 no 10 pp 1027ndash1039 1996

[105] A N Nagappa P A Thakurdesai N V Rao and J SinghldquoAntidiabetic activity ofTerminalia catappa Linn fruitsrdquo Journalof Ethnopharmacology vol 88 no 1 pp 45ndash50 2003

[106] K Datta S Sinha and P Chattopadhyay ldquoReactive oxygenspecies in health and diseaserdquoNationalMedical Journal of Indiavol 13 no 6 pp 304ndash310 2000

[107] R R Holman and R C Turner ldquoOral agents and insulin in thetreatment of NIDDMrdquo in Textbook of Diabetes J Williams Edpp 407ndash469 Blackwell Press Oxford UK 1991

[108] F Giacco and M Brownlee ldquoOxidative stress and diabeticcomplicationsrdquo Circulation Research vol 107 no 9 pp 1058ndash1070 2010

[109] B K Rao M M Kesavulu R Giri and C A Rao ldquoAntidiabeticand hypolipidemic effects ofMomordicacymbalariaHook fruitpowder in alloxan-diabetic ratsrdquo Journal of Ethnopharmacologyvol 67 no 1 pp 103ndash109 1999

[110] J K Grover V Vats V Rathi and S S Dawar ldquoTraditionalIndian anti-diabetic plants attenuate progression of renal dam-age in streptozotocin induced diabetic micerdquo Journal of Ethno-pharmacology vol 76 no 3 pp 233ndash238 2001

[111] R K Gupta A N Kesari P S Murthy R Chandra V Tandonand GWatal ldquoHypoglycemic and antidiabetic effect of ethano-lic extract of leaves of Annona squamosa L in experimentalanimalsrdquo Journal of Ethnopharmacology vol 99 no 1 pp 75ndash81 2005

[112] S Gupta N Ahmad A-L Nieminen andHMukhtar ldquoGrowthinhibition cell-cycle dysregulation and induction of apopto-sis by green tea constituent (-)-epigallocatechin-3-gallate inandrogen-sensitive and androgen-insensitive human prostatecarcinoma cellsrdquoToxicology andApplied Pharmacology vol 164no 1 pp 82ndash90 2000

[113] T Yokozawa Y A Kim H Y Kim Y A Lee and G-I NonakaldquoProtective effect of persimmon peel polyphenol against highglucose-induced oxidative stress in LLC-PK1 cellsrdquo Food andChemical Toxicology vol 45 no 10 pp 1979ndash1987 2007

12 Journal of Chemistry

[114] M S Brewer ldquoNatural antioxidants sources compoundsmechanisms of action and potential applicationsrdquo Comprehen-sive Reviews in Food Science and Food Safety vol 10 no 4 pp221ndash247 2011

[115] K Kawakami H Nishida N Tatewaki Y Nakajima T Konishiand M Hirayama ldquoPersimmon leaf extract inhibits the ATMactivity during DNA damage response induced by Doxorubicinin A549 lung adenocarcinoma cellsrdquo Bioscience Biotechnologyand Biochemistry vol 75 no 4 pp 650ndash655 2011

[116] D Steinberg S Parthasarathy T E Carew J C Khoo and JL Witztum ldquoBeyond cholesterol modifications of low-densitylipoprotein that increase its atherogenicityrdquo The New EnglandJournal of Medicine vol 320 no 14 pp 915ndash924 1989

[117] P M Kris-Etherton and C L Keen ldquoEvidence that the anti-oxidant flavonoids in tea and cocoa are beneficial for cardiovas-cular healthrdquo Current Opinion in Lipidology vol 13 no 1 pp41ndash49 2002

[118] C Manach A Mazur and A Scalbert ldquoPolyphenols and pre-vention of cardiovascular diseasesrdquo Current Opinion in Lipidol-ogy vol 16 no 1 pp 77ndash84 2005

[119] J W Anderson B M Smith and N J Gustafson ldquoHealthbenefits and practical aspects of high-fiber dietsrdquo AmericanJournal of Clinical Nutrition vol 59 no 5 pp 1242ndash1247 1994

[120] D Kromhout A Menotti H Kesteloot and S Sans ldquoPreven-tion of coronary heart disease by diet and lifestyle evidencefrom prospective cross-cultural cohort and intervention stud-iesrdquo Circulation vol 105 no 7 pp 893ndash898 2002

[121] E B Rimm M J Stampfer A Ascherio E Giovannucci G AColditz andWCWillett ldquoVitamin E consumption and the riskof coronary heart disease in menrdquo The New England Journal ofMedicine vol 328 no 20 pp 1450ndash1456 1993

[122] L Dauchet J Ferrieres D Arveiler et al ldquoFrequency of fruitand vegetable consumption and coronary heart disease inFrance and Northern Ireland the prime studyrdquo British Journalof Nutrition vol 92 no 6 pp 963ndash972 2004

[123] S Gorinstein GW Kulasek E Bartnikowska et al ldquoThe effectsof diets supplementedwith either whole persimmon or phenol-free persimmon on rats fed cholesterolrdquo Food Chemistry vol70 no 3 pp 303ndash308 2000

[124] M G L Hertog E J M Feskens P C H HollmanM B Katanand D Kromhout ldquoDietary antioxidant flavonoids and risk ofcoronary heart disease the Zutphen Elderly studyrdquoThe Lancetvol 342 no 8878 pp 1007ndash1011 1993

[125] H Seo B D Jeon andR Sungpil ldquoPersimmon vinegar ripeningwith the mountain-cultivated ginseng ingestion reduces bloodlipids and lowers inflammatory cytokines in obese adolescentsrdquoJournal of Exercise Nutrition and Biochemistry vol 19 no 1 pp1ndash10 2015

[126] R H Liu ldquoPotential synergy of phytochemicals in cancerprevention mechanism of actionrdquo Journal of Nutrition vol 134no 12 supplement pp 3479Sndash3485S 2004

[127] S T Mayne ldquoAntioxidant nutrients and chronic disease use ofbiomarkers of exposure and oxidative stress status in epidemi-ologic researchrdquo Journal of Nutrition vol 133 no 3 pp 933sndash940s 2003

[128] H Tapiero D M Townsend and K D Tew ldquoThe role of caro-tenoids in the prevention of human pathologiesrdquo Biomedicineand Pharmacotherapy vol 58 no 2 pp 100ndash110 2004

[129] J Tao and S L Zhang ldquoMetabolismof carotenoid and its regula-tion in garden croprdquo Journal of Zhejiang University (Agricultureamp Life Sciences) vol 29 pp 585ndash590 2003

[130] W Miki ldquoBiological functions and activities of animal caro-tenoidsrdquo Pure and Applied Chemistry vol 63 no 1 pp 141ndash1461991

[131] H Fujiki ldquoGreen tea health benefits as cancer preventive forhumansrdquo Chemical Record vol 5 no 3 pp 119ndash132 2005

[132] A P George and S Redpath ldquoHealth and medicinal benefits ofpersimmon fruit a reviewrdquo Advances in Horticultural Sciencevol 22 no 4 pp 244ndash249 2008

[133] T Hussain S Gupta V M Adhami and H Mukhtar ldquoGreentea constituent epigallocatechin-3-gallate selectively inhibitsCOX-2 without affecting COX-1 expression in human prostatecarcinoma cellsrdquo International Journal of Cancer vol 113 no 4pp 660ndash669 2005

[134] Y-C Wang and U Bachrach ldquoThe specific anti-cancer activityof green tea (minus)-epigallocatechin-3-gallate (EGCG)rdquo AminoAcids vol 22 no 2 pp 131ndash143 2002

[135] O Takayuki ldquoPersimmons your healthy autumn treatsrdquoAsahikawa Information vol 108 pp 1ndash2 2005

[136] T Fukuda and H Shibata ldquoPersimmon calyx extracts as anti-convulsants and to alleviate the side effects of barbituric acidcompoundsrdquo Patent Japanease Kokai Tokkyo Koho vol 6 pp649ndash653 1994

[137] T Matsuno ldquoXanthophylls as precursors of retinoidsrdquo Pure andApplied Chemistry vol 63 no 1 pp 81ndash88 1991

[138] N Gato A Kadowaki N Hashimoto S-I Yokoyama and KMatsumoto ldquoPersimmon fruit tannin-rich fiber reduces choles-terol levels in humansrdquoAnnals of Nutrition andMetabolism vol62 no 1 pp 1ndash6 2013

[139] A Nagao ldquoAbsorption and function of dietary carotenoidsrdquoForum of Nutrition vol 61 pp 55ndash63 2009

[140] PD Fraser andPM Bramley ldquoThebiosynthesis andnutritionaluses of carotenoidsrdquo Progress in Lipid Research vol 43 no 3 pp228ndash265 2004

[141] D Fusco G Colloca M R Lo Monaco and M Cesari ldquoEffectsof antioxidant supplementation on the aging processrdquo ClinicalInterventions in Aging vol 2 no 3 pp 377ndash387 2007

[142] JM Seddon U Ajan and R D Sperduto ldquoDietary carotenoidsvitamins A C and E and advance age-related macular degen-eration Eye Disease Case Study Grouprdquo Journal of AmericanMedical Association vol 272 no 18 pp 1413ndash1420 1992

[143] B-J An J-H Kwak J-M Park et al ldquoInhibition of enzymeactivities and the antiwrinkle effect of polyphenol isolated fromthe persimmon leaf (Diospyros kaki folium) on human skinrdquoDermatologic Surgery vol 31 no 7 pp 848ndash854 2005

[144] H Arakawa M Takasaki N Tajima H Fukamachi and TIgarashi ldquoAntibacterial activities of persimmon extracts relatewith their hydrogen peroxide concentrationrdquo Biological andPharmaceutical Bulletin vol 37 no 7 pp 1119ndash1123 2014

[145] S D Ladas D Kamberoglou G Karamanolis J Vlachogian-nakos and I Zouboulis-Vafiadis ldquoSystematic review Coca-Cola can effectively dissolve gastric phytobezoars as a first-linetreatmentrdquo Alimentary Pharmacology and Therapeutics vol 37no 2 pp 169ndash173 2013

[146] T J Cifuentes C R Robles P P Parrilla et al ldquoPolyphenols andhealth what compounds are involvedrdquo Nutrition Metabolismand Cardiovascular Diseases vol 20 no 1 pp 1ndash6 2010

[147] J Gaya L Barranco A Llompart J Reyes and A ObradorldquoPersimmon bezoars a successful combined therapyrdquoGastroin-testinal Endoscopy vol 55 no 4 pp 581ndash583 2002

[148] P G Hayes and O D Rotstein ldquoGastrointestinal phytobezoarspresentation and managementrdquo Canadian Journal of Surgeryvol 29 no 6 pp 419ndash420 1986

Journal of Chemistry 13

[149] MM Krausz E ZMoriel A Ayalon D Pode and A L DurstldquoSurgical aspects of gastrointestinal persimmon phytobezoartreatmentrdquoThe American Journal of Surgery vol 152 no 5 pp526ndash530 1986

[150] P Walker-Renard ldquoUpdate on the medicinal management ofphytobezoarsrdquo The American Journal of Gastroenterology vol88 no 10 pp 1663ndash1666 1993

[151] S S Ha H S LeeM K Jung et al ldquoAcute intestinal obstructioncaused by a persimmon phytobezoar after dissolution therapywith Coca-Colardquo The Korean Journal of Internal Medicine vol22 no 4 pp 300ndash303 2007

[152] J Han S Kang R Choue et al ldquoFree radical scavenging effectofDiospyros kaki Laminaria japonica andUndaria pinnatifidardquoFitoterapia vol 73 no 7-8 pp 710ndash712 2002

Submit your manuscripts athttpwwwhindawicom

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Inorganic ChemistryInternational Journal of

Hindawi Publishing Corporation httpwwwhindawicom Volume 2014

International Journal ofPhotoenergy

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Carbohydrate Chemistry

International Journal of

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CatalystsJournal of

Page 10: Review Article Chemistry and Functionality of Bioactive ...downloads.hindawi.com/journals/jchem/2016/3424025.pdf · Review Article Chemistry and Functionality of Bioactive Compounds

10 Journal of Chemistry

[53] Y J Yang and S J Kim ldquoChanges in chlorophyll and carotenoidcontents during cold and CA storage and characterization ofthe carotenoids in the peel of lsquoFujirsquo apple fruitrdquo Journal of KoreanSociety and Horticultural Science vol 36 pp 500ndash505 1995

[54] Y C Kim J B Kim K J Cho I S Lee and S K ChungldquoCarotenoid content of Korean persimmon peel and theirchanges in storagerdquo Food Science and Biotechnology vol 11 no5 pp 477ndash479 2002

[55] J Tous and L Ferguson ldquoMediterranean fruitsrdquo in Progress inNew Crops J Janick Ed pp 416ndash430 ASHS Press ArlingtonVa USA 1996

[56] B YuanH L Xu and S P Leng ldquoContent and chemical compo-sition of carotenoids in persimmon fruitrdquo Chinese AgriculturalScience Bulletin vol 22 pp 277ndash280 2006 (Chinese)

[57] D Zhao C Zhou and J Tao ldquoCarotenoid accumulation andcarotenogenic genes expression during two types of persimmonfruit (Diospyros kaki L) developmentrdquo Plant Molecular BiologyReporter vol 29 no 3 pp 646ndash654 2011

[58] L Plaza C Colina B D Ancos C Sanchez-Moreno and MPilar Cano ldquoInfluence of ripening and astringency on carote-noid content of high-pressure treated persimmon fruit (Dio-spyros kakiL)rdquo FoodChemistry vol 130 no 3 pp 591ndash597 2012

[59] T Niikawa T Suzuki T Ozeki M Kato and Y Ikoma ldquoChar-acteristics of carotenoid accumulation duringmaturation of theJapanese persimmon lsquoFuyursquordquo Horticultural Research vol 6 pp251ndash256 2007 (Japanese)

[60] G Britton ldquoStructure and properties of carotenoids in relationto functionrdquo The FASEB Journal vol 9 no 15 pp 1551ndash15581995

[61] H G Daood P Biacs B Czinkotai and A Hoschke ldquoChroma-tographic investigation of carotenoids sugars and organic acidsfrom Diospyros kaki fruitsrdquo Food Chemistry vol 45 no 2 pp151ndash155 1992

[62] I-C Jang E-K Jo S-M Bae et al ldquoAntioxidant activity andfatty acid composition of four different persimmon seedsrdquo FoodScience and Technology Research vol 16 no 6 pp 577ndash5842010

[63] J AMenendez L Vellon R Colomer and R Lupu ldquoOleic acidthe main monounsaturated fatty acid of olive oil suppressesHer-2neu (erbB-2) expression and synergistically enhances thegrowth inhibitory effects of trastuzumab (Herceptin) in breastcancer cells with Her-2neu oncogene amplificationrdquo Annals ofOncology vol 16 no 3 pp 359ndash371 2005

[64] W C Willett ldquoThe role of dietary n-6 fatty acids in theprevention of cardiovascular diseaserdquo Journal of CardiovascularMedicine vol 8 no 1 pp S42ndashS45 2007

[65] K Kawakami S Aketa H Sakai Y Watanabe H Nishida andM Hirayama ldquoAntihypertensive and vasorelaxant effects ofwater-soluble proanthocyanidins from persimmon leaf tea inspontaneously hypertensive ratsrdquo Bioscience Biotechnology andBiochemistry vol 75 no 8 pp 1435ndash1439 2011

[66] G Chen J Xue S-X Xu and R-Q Zhang ldquoChemical con-stituents of the leaves of Diospyros kaki and their cytotoxiceffectsrdquo Journal of Asian Natural Products Research vol 9 no4 pp 347ndash353 2007

[67] S Singh and H Joshi ldquoDiospyros kaki (Ebenaceae) a reviewrdquoAsian Journal of Research in Pharmaceutical Science vol 1 no3 pp 55ndash58 2011

[68] J L Navarro A Tarrega M A Sentandreu and E SentandreuldquoPartial purification and characterization of polyphenol oxi-dase from persimmonrdquo Food Chemistry vol 157 pp 283ndash2892014

[69] O V Zillich U Schweiggert-Weisz P Eisner and M KerscherldquoPolyphenols as active ingredients for cosmetic productsrdquoInternational Journal of Cosmetic Science vol 37 no 5 pp 455ndash464 2015

[70] H Palafox-Carlos J F Ayala-Zavala and G A Gonzalez-Aguilar ldquoThe role of dietary fiber in the bioaccessibility andbioavailability of fruit and vegetable antioxidantsrdquo Journal ofFood Science vol 76 no 1 pp R6ndashR15 2011

[71] A Ratz-Łyko J Arct SMajewski andK Pytkowska ldquoInfluenceof polyphenols on the physiological processes in the skinrdquoPhytotherapy Research vol 29 no 4 pp 509ndash517 2015

[72] J Sun Y-F Chu X Wu and R H Liu ldquoAntioxidant andantiproliferative activities of common fruitsrdquo Journal of Agricul-tural and Food Chemistry vol 50 no 25 pp 7449ndash7454 2002

[73] E Sentandreu M Cerdan-Calero J M Halket and J LNavarro ldquoRapid screening of low-molecular-weight phenolsfrom persimmon (Diospyros kaki) pulp using liquid chroma-tographyUVndashvisibleelectrospray mass spectrometry analysisrdquoJournal of the Science of Food and Agriculture vol 95 pp 1648ndash1654 2015

[74] L Bravo ldquoPolyphenols chemistry dietary sources metabolismand nutritional significancerdquo Nutrition Reviews vol 56 no 11pp 317ndash333 1998

[75] T Akagi Y Suzuki A Ikegami et al ldquoCondensed tannin com-position analysis in persimmon (Diospyros kakiThunb) fruit byacid catalysis in the presence of excess phloroglucinolrdquo Journalof the Japanese Society for Horticultural Science vol 79 no 3 pp275ndash281 2010

[76] C Li R Leverence J D Trombley et al ldquoHighmolecularweightpersimmon (Diospyros kaki L) proanthocyanidin a highlygalloylated a-linked tannin with an unusual flavonol terminalunitmyricetinrdquo Journal of Agricultural and FoodChemistry vol58 no 16 pp 9033ndash9042 2010

[77] C A Rice-Evans N J Miller and G Paganga ldquoStructure-antioxidant activity relationships of flavonoids and phenolicacidsrdquo Free Radical Biology andMedicine vol 20 no 7 pp 933ndash956 1996

[78] R Tsao ldquoChemistry and biochemistry of dietary polyphenolsrdquoNutrients vol 2 no 12 pp 1231ndash1246 2010

[79] S Uchida H Ohta R Edamatsu M Hiromatsu A Mori andG I Nomaka ldquoPersimmon tannin prolongs life span of stroke-prone spontaneously hypertensive rats (SHRSP) by acting as afree-radical scavengerrdquo in New Horizons in Preventing Cardio-vascular Diseases Y Yamori and T Strasser Eds pp 15ndash17Academic Press Amsterdam The Netherlands Elsevier NewYork NY USA 1989

[80] S Uchida H Ohta M Niwa et al ldquoProlongation of life spanof stroke-prone spontaneously hypertensive rats (SHRSP)ingesting persimmon tanninrdquo Chemical and PharmaceuticalBulletin vol 38 no 4 pp 1049ndash1052 1990

[81] S Gorinstein G W Kulasek E Bartnikowska et al ldquoThe influ-ence of persimmon peel and persimmon pulp on the lipidmeta-bolism and antioxidant activity of rats fed cholesterolrdquo Journalof Nutritional Biochemistry vol 9 no 4 pp 223ndash227 1998

[82] K Matsumoto A Kadowaki N Ozaki et al ldquoBile acid-bind-ing ability of kaki-tannin from young fruits of persimmon (Dio-spyros kaki) in vitro and in vivordquo Phytotherapy Research vol 25no 4 pp 624ndash628 2011

[83] K Ueda R Kawabata T Irie Y Nakai Y Tohya and T Sak-aguchi ldquoInactivation of pathogenic viruses by plant-derivedtannins strong effects of extracts from persimmon (Diospyros

Journal of Chemistry 11

kaki) on a broad range of virusesrdquo PLoS ONE vol 8 no 1Article ID e55343 10 pages 2013

[84] H Suzuki M Konishi M Kimura T Mori M Suzuki and TIkemi ldquoInhibitory effects ofDiospyros kakiTHUNB Extracts indental caries in ratsrdquo Japanese Journal of Conservative Dentistryvol 50 no 2 pp 140ndash145 2007

[85] S Sakanaka Y Tachibana and Y Okada ldquoPreparation andantioxidant properties of extracts of Japanese persimmon leaftea (Kakinoha-cha)rdquo Food Chemistry vol 89 no 4 pp 569ndash5752005

[86] MHosny and J PN Rosazza ldquoNovel oxidations of (+)-catechinby horseradish peroxidase and laccaserdquo Journal of Agriculturaland Food Chemistry vol 50 no 20 pp 5539ndash5545 2002

[87] J-I Inokuchi H Okabe T Yamauchi and A NagamatsuldquoInhibitors of angiotensin converting enzyme in crude drugsrdquoChemical and Pharmaceutical Bulletin vol 32 no 9 pp 3615ndash3619 1984

[88] Y Tian B Zou L Yang et al ldquoHigh molecular weight per-simmon tannin ameliorates cognition deficits and attenuatesoxidative damage in senescent mice induced by d-galactoserdquoFood andChemical Toxicology vol 49 no 8 pp 1728ndash1736 2011

[89] Y Achiwa H Hibasami H Katsuzaki K Imai and T KomiyaldquoInhibitory effects of persimmon (Diospyros kaki) extract andrelated polyphenol compounds on growth of human lymphoidleukemia cellsrdquo Bioscience Biotechnology and Biochemistry vol61 no 7 pp 1099ndash1101 1997

[90] J Gross Carotenoids vol 123 Academic Press New York NYUSA 1987

[91] B De Ancos E Gonzalez and M P Cano ldquoEffect of high-pressure treatment on the carotenoid composition and theradical scavenging activity of persimmon fruit pureesrdquo Journalof Agricultural and Food Chemistry vol 48 no 8 pp 3542ndash3548 2000

[92] T Matsuo and S Ito ldquoThe chemical structure of Kaki-tanninfrom immature fruit of the persimmon (Diospyros kaki L)rdquoAgricultural and Biological Chemistry vol 42 no 9 pp 1637ndash1643 1978

[93] S Gorinstein M Zemser M Weisz et al ldquoFluorometric anal-ysis of phenolics in persimmonsrdquo Bioscience Biotechnology andBiochemistry vol 58 no 6 pp 1087ndash1092 1994

[94] S O Lee H J LeeMH Yu H G Im and I S Lee ldquoTotal poly-phenol contents and antioxidant activities of methanol extractsfrom vegetables produced in Ullung Islandrdquo Korean Journal ofFood Science and Technology vol 37 no 2 pp 233ndash240 2005

[95] U V Mallavadhani A K Panda and Y R Rao ldquoPharmacologyand chemotaxonomy of Diospyrosrdquo Phytochemistry vol 49 no4 pp 901ndash951 1998

[96] G Block B Patterson and A Subar ldquoFruit vegetables andcancer prevention a review of the epidemiological evidencerdquoNutrition and Cancer vol 18 no 1 pp 1ndash29 1992

[97] G van Poppel ldquoCarotenoids and cancer an updatewith empha-sis on human intervention studiesrdquo European Journal of Cancervol 29 no 9 pp 1335ndash1344 1993

[98] E Giovannucci A Ascherio E B Rimm M J Stampfer G AColditz and W C Willett ldquoIntake of carotenoids and retino inrelation to risk of prostate cancerrdquo Journal of theNational CancerInstitute vol 87 no 23 pp 1767ndash1776 1995

[99] T Johns R L A Mahunnah P Sanaya L Chapman and TTicktin ldquoSaponins and phenolic content in plant dietary addi-tives of a traditional subsistence community the Batemi ofNgorongoro District Tanzaniardquo Journal of Ethnopharmacologyvol 66 no 1 pp 1ndash10 1999

[100] Y Zhang X Lu Y Zhang L Qin and J Zhang ldquoSulfatedmodification and immunomodulatory activity of water-solublepolysaccharides derived from fresh Chinese persimmon fruitrdquoInternational Journal of Biological Macromolecules vol 46 no1 pp 67ndash71 2010

[101] Y-J Moon and Y-S Cha ldquoEffects of persimmon-vinegar onlipid metabolism and alcohol clearance in chronic alcohol-fedratsrdquo Journal of Medicinal Food vol 11 no 1 pp 38ndash45 2008

[102] H S Ahn T I Jeon J Y Lee S G Hwang Y Lim and D KPark ldquoAntioxidative activity of persimmon and grape seedextract in vitro and in vivordquo Nutrition Research vol 22 no 11pp 1265ndash1273 2002

[103] H Itamurah N Murakami and H Nagamatsu ldquoProperty ofkaki-tannin as a functional composition in persimmon fruitflesh and leaves and its solubility in artificial stomach liquidrdquoin Proceedings of the 27th International Horticultural Congressamp Exhibition (IHC rsquo06) vol 8 pp 265ndash267 August 2006

[104] K A Steinmetz and J D Potter ldquoVegetables fruit and cancerprevention a reviewrdquo Journal of the American Dietetic Associa-tion vol 96 no 10 pp 1027ndash1039 1996

[105] A N Nagappa P A Thakurdesai N V Rao and J SinghldquoAntidiabetic activity ofTerminalia catappa Linn fruitsrdquo Journalof Ethnopharmacology vol 88 no 1 pp 45ndash50 2003

[106] K Datta S Sinha and P Chattopadhyay ldquoReactive oxygenspecies in health and diseaserdquoNationalMedical Journal of Indiavol 13 no 6 pp 304ndash310 2000

[107] R R Holman and R C Turner ldquoOral agents and insulin in thetreatment of NIDDMrdquo in Textbook of Diabetes J Williams Edpp 407ndash469 Blackwell Press Oxford UK 1991

[108] F Giacco and M Brownlee ldquoOxidative stress and diabeticcomplicationsrdquo Circulation Research vol 107 no 9 pp 1058ndash1070 2010

[109] B K Rao M M Kesavulu R Giri and C A Rao ldquoAntidiabeticand hypolipidemic effects ofMomordicacymbalariaHook fruitpowder in alloxan-diabetic ratsrdquo Journal of Ethnopharmacologyvol 67 no 1 pp 103ndash109 1999

[110] J K Grover V Vats V Rathi and S S Dawar ldquoTraditionalIndian anti-diabetic plants attenuate progression of renal dam-age in streptozotocin induced diabetic micerdquo Journal of Ethno-pharmacology vol 76 no 3 pp 233ndash238 2001

[111] R K Gupta A N Kesari P S Murthy R Chandra V Tandonand GWatal ldquoHypoglycemic and antidiabetic effect of ethano-lic extract of leaves of Annona squamosa L in experimentalanimalsrdquo Journal of Ethnopharmacology vol 99 no 1 pp 75ndash81 2005

[112] S Gupta N Ahmad A-L Nieminen andHMukhtar ldquoGrowthinhibition cell-cycle dysregulation and induction of apopto-sis by green tea constituent (-)-epigallocatechin-3-gallate inandrogen-sensitive and androgen-insensitive human prostatecarcinoma cellsrdquoToxicology andApplied Pharmacology vol 164no 1 pp 82ndash90 2000

[113] T Yokozawa Y A Kim H Y Kim Y A Lee and G-I NonakaldquoProtective effect of persimmon peel polyphenol against highglucose-induced oxidative stress in LLC-PK1 cellsrdquo Food andChemical Toxicology vol 45 no 10 pp 1979ndash1987 2007

12 Journal of Chemistry

[114] M S Brewer ldquoNatural antioxidants sources compoundsmechanisms of action and potential applicationsrdquo Comprehen-sive Reviews in Food Science and Food Safety vol 10 no 4 pp221ndash247 2011

[115] K Kawakami H Nishida N Tatewaki Y Nakajima T Konishiand M Hirayama ldquoPersimmon leaf extract inhibits the ATMactivity during DNA damage response induced by Doxorubicinin A549 lung adenocarcinoma cellsrdquo Bioscience Biotechnologyand Biochemistry vol 75 no 4 pp 650ndash655 2011

[116] D Steinberg S Parthasarathy T E Carew J C Khoo and JL Witztum ldquoBeyond cholesterol modifications of low-densitylipoprotein that increase its atherogenicityrdquo The New EnglandJournal of Medicine vol 320 no 14 pp 915ndash924 1989

[117] P M Kris-Etherton and C L Keen ldquoEvidence that the anti-oxidant flavonoids in tea and cocoa are beneficial for cardiovas-cular healthrdquo Current Opinion in Lipidology vol 13 no 1 pp41ndash49 2002

[118] C Manach A Mazur and A Scalbert ldquoPolyphenols and pre-vention of cardiovascular diseasesrdquo Current Opinion in Lipidol-ogy vol 16 no 1 pp 77ndash84 2005

[119] J W Anderson B M Smith and N J Gustafson ldquoHealthbenefits and practical aspects of high-fiber dietsrdquo AmericanJournal of Clinical Nutrition vol 59 no 5 pp 1242ndash1247 1994

[120] D Kromhout A Menotti H Kesteloot and S Sans ldquoPreven-tion of coronary heart disease by diet and lifestyle evidencefrom prospective cross-cultural cohort and intervention stud-iesrdquo Circulation vol 105 no 7 pp 893ndash898 2002

[121] E B Rimm M J Stampfer A Ascherio E Giovannucci G AColditz andWCWillett ldquoVitamin E consumption and the riskof coronary heart disease in menrdquo The New England Journal ofMedicine vol 328 no 20 pp 1450ndash1456 1993

[122] L Dauchet J Ferrieres D Arveiler et al ldquoFrequency of fruitand vegetable consumption and coronary heart disease inFrance and Northern Ireland the prime studyrdquo British Journalof Nutrition vol 92 no 6 pp 963ndash972 2004

[123] S Gorinstein GW Kulasek E Bartnikowska et al ldquoThe effectsof diets supplementedwith either whole persimmon or phenol-free persimmon on rats fed cholesterolrdquo Food Chemistry vol70 no 3 pp 303ndash308 2000

[124] M G L Hertog E J M Feskens P C H HollmanM B Katanand D Kromhout ldquoDietary antioxidant flavonoids and risk ofcoronary heart disease the Zutphen Elderly studyrdquoThe Lancetvol 342 no 8878 pp 1007ndash1011 1993

[125] H Seo B D Jeon andR Sungpil ldquoPersimmon vinegar ripeningwith the mountain-cultivated ginseng ingestion reduces bloodlipids and lowers inflammatory cytokines in obese adolescentsrdquoJournal of Exercise Nutrition and Biochemistry vol 19 no 1 pp1ndash10 2015

[126] R H Liu ldquoPotential synergy of phytochemicals in cancerprevention mechanism of actionrdquo Journal of Nutrition vol 134no 12 supplement pp 3479Sndash3485S 2004

[127] S T Mayne ldquoAntioxidant nutrients and chronic disease use ofbiomarkers of exposure and oxidative stress status in epidemi-ologic researchrdquo Journal of Nutrition vol 133 no 3 pp 933sndash940s 2003

[128] H Tapiero D M Townsend and K D Tew ldquoThe role of caro-tenoids in the prevention of human pathologiesrdquo Biomedicineand Pharmacotherapy vol 58 no 2 pp 100ndash110 2004

[129] J Tao and S L Zhang ldquoMetabolismof carotenoid and its regula-tion in garden croprdquo Journal of Zhejiang University (Agricultureamp Life Sciences) vol 29 pp 585ndash590 2003

[130] W Miki ldquoBiological functions and activities of animal caro-tenoidsrdquo Pure and Applied Chemistry vol 63 no 1 pp 141ndash1461991

[131] H Fujiki ldquoGreen tea health benefits as cancer preventive forhumansrdquo Chemical Record vol 5 no 3 pp 119ndash132 2005

[132] A P George and S Redpath ldquoHealth and medicinal benefits ofpersimmon fruit a reviewrdquo Advances in Horticultural Sciencevol 22 no 4 pp 244ndash249 2008

[133] T Hussain S Gupta V M Adhami and H Mukhtar ldquoGreentea constituent epigallocatechin-3-gallate selectively inhibitsCOX-2 without affecting COX-1 expression in human prostatecarcinoma cellsrdquo International Journal of Cancer vol 113 no 4pp 660ndash669 2005

[134] Y-C Wang and U Bachrach ldquoThe specific anti-cancer activityof green tea (minus)-epigallocatechin-3-gallate (EGCG)rdquo AminoAcids vol 22 no 2 pp 131ndash143 2002

[135] O Takayuki ldquoPersimmons your healthy autumn treatsrdquoAsahikawa Information vol 108 pp 1ndash2 2005

[136] T Fukuda and H Shibata ldquoPersimmon calyx extracts as anti-convulsants and to alleviate the side effects of barbituric acidcompoundsrdquo Patent Japanease Kokai Tokkyo Koho vol 6 pp649ndash653 1994

[137] T Matsuno ldquoXanthophylls as precursors of retinoidsrdquo Pure andApplied Chemistry vol 63 no 1 pp 81ndash88 1991

[138] N Gato A Kadowaki N Hashimoto S-I Yokoyama and KMatsumoto ldquoPersimmon fruit tannin-rich fiber reduces choles-terol levels in humansrdquoAnnals of Nutrition andMetabolism vol62 no 1 pp 1ndash6 2013

[139] A Nagao ldquoAbsorption and function of dietary carotenoidsrdquoForum of Nutrition vol 61 pp 55ndash63 2009

[140] PD Fraser andPM Bramley ldquoThebiosynthesis andnutritionaluses of carotenoidsrdquo Progress in Lipid Research vol 43 no 3 pp228ndash265 2004

[141] D Fusco G Colloca M R Lo Monaco and M Cesari ldquoEffectsof antioxidant supplementation on the aging processrdquo ClinicalInterventions in Aging vol 2 no 3 pp 377ndash387 2007

[142] JM Seddon U Ajan and R D Sperduto ldquoDietary carotenoidsvitamins A C and E and advance age-related macular degen-eration Eye Disease Case Study Grouprdquo Journal of AmericanMedical Association vol 272 no 18 pp 1413ndash1420 1992

[143] B-J An J-H Kwak J-M Park et al ldquoInhibition of enzymeactivities and the antiwrinkle effect of polyphenol isolated fromthe persimmon leaf (Diospyros kaki folium) on human skinrdquoDermatologic Surgery vol 31 no 7 pp 848ndash854 2005

[144] H Arakawa M Takasaki N Tajima H Fukamachi and TIgarashi ldquoAntibacterial activities of persimmon extracts relatewith their hydrogen peroxide concentrationrdquo Biological andPharmaceutical Bulletin vol 37 no 7 pp 1119ndash1123 2014

[145] S D Ladas D Kamberoglou G Karamanolis J Vlachogian-nakos and I Zouboulis-Vafiadis ldquoSystematic review Coca-Cola can effectively dissolve gastric phytobezoars as a first-linetreatmentrdquo Alimentary Pharmacology and Therapeutics vol 37no 2 pp 169ndash173 2013

[146] T J Cifuentes C R Robles P P Parrilla et al ldquoPolyphenols andhealth what compounds are involvedrdquo Nutrition Metabolismand Cardiovascular Diseases vol 20 no 1 pp 1ndash6 2010

[147] J Gaya L Barranco A Llompart J Reyes and A ObradorldquoPersimmon bezoars a successful combined therapyrdquoGastroin-testinal Endoscopy vol 55 no 4 pp 581ndash583 2002

[148] P G Hayes and O D Rotstein ldquoGastrointestinal phytobezoarspresentation and managementrdquo Canadian Journal of Surgeryvol 29 no 6 pp 419ndash420 1986

Journal of Chemistry 13

[149] MM Krausz E ZMoriel A Ayalon D Pode and A L DurstldquoSurgical aspects of gastrointestinal persimmon phytobezoartreatmentrdquoThe American Journal of Surgery vol 152 no 5 pp526ndash530 1986

[150] P Walker-Renard ldquoUpdate on the medicinal management ofphytobezoarsrdquo The American Journal of Gastroenterology vol88 no 10 pp 1663ndash1666 1993

[151] S S Ha H S LeeM K Jung et al ldquoAcute intestinal obstructioncaused by a persimmon phytobezoar after dissolution therapywith Coca-Colardquo The Korean Journal of Internal Medicine vol22 no 4 pp 300ndash303 2007

[152] J Han S Kang R Choue et al ldquoFree radical scavenging effectofDiospyros kaki Laminaria japonica andUndaria pinnatifidardquoFitoterapia vol 73 no 7-8 pp 710ndash712 2002

Submit your manuscripts athttpwwwhindawicom

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Inorganic ChemistryInternational Journal of

Hindawi Publishing Corporation httpwwwhindawicom Volume 2014

International Journal ofPhotoenergy

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Carbohydrate Chemistry

International Journal of

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Journal of

Chemistry

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Advances in

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Analytical Methods in Chemistry

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Bioinorganic Chemistry and ApplicationsHindawi Publishing Corporationhttpwwwhindawicom Volume 2014

SpectroscopyInternational Journal of

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The Scientific World JournalHindawi Publishing Corporation httpwwwhindawicom Volume 2014

Medicinal ChemistryInternational Journal of

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Chromatography Research International

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Applied ChemistryJournal of

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Theoretical ChemistryJournal of

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Analytical ChemistryInternational Journal of

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Quantum Chemistry

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Organic Chemistry International

ElectrochemistryInternational Journal of

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CatalystsJournal of

Page 11: Review Article Chemistry and Functionality of Bioactive ...downloads.hindawi.com/journals/jchem/2016/3424025.pdf · Review Article Chemistry and Functionality of Bioactive Compounds

Journal of Chemistry 11

kaki) on a broad range of virusesrdquo PLoS ONE vol 8 no 1Article ID e55343 10 pages 2013

[84] H Suzuki M Konishi M Kimura T Mori M Suzuki and TIkemi ldquoInhibitory effects ofDiospyros kakiTHUNB Extracts indental caries in ratsrdquo Japanese Journal of Conservative Dentistryvol 50 no 2 pp 140ndash145 2007

[85] S Sakanaka Y Tachibana and Y Okada ldquoPreparation andantioxidant properties of extracts of Japanese persimmon leaftea (Kakinoha-cha)rdquo Food Chemistry vol 89 no 4 pp 569ndash5752005

[86] MHosny and J PN Rosazza ldquoNovel oxidations of (+)-catechinby horseradish peroxidase and laccaserdquo Journal of Agriculturaland Food Chemistry vol 50 no 20 pp 5539ndash5545 2002

[87] J-I Inokuchi H Okabe T Yamauchi and A NagamatsuldquoInhibitors of angiotensin converting enzyme in crude drugsrdquoChemical and Pharmaceutical Bulletin vol 32 no 9 pp 3615ndash3619 1984

[88] Y Tian B Zou L Yang et al ldquoHigh molecular weight per-simmon tannin ameliorates cognition deficits and attenuatesoxidative damage in senescent mice induced by d-galactoserdquoFood andChemical Toxicology vol 49 no 8 pp 1728ndash1736 2011

[89] Y Achiwa H Hibasami H Katsuzaki K Imai and T KomiyaldquoInhibitory effects of persimmon (Diospyros kaki) extract andrelated polyphenol compounds on growth of human lymphoidleukemia cellsrdquo Bioscience Biotechnology and Biochemistry vol61 no 7 pp 1099ndash1101 1997

[90] J Gross Carotenoids vol 123 Academic Press New York NYUSA 1987

[91] B De Ancos E Gonzalez and M P Cano ldquoEffect of high-pressure treatment on the carotenoid composition and theradical scavenging activity of persimmon fruit pureesrdquo Journalof Agricultural and Food Chemistry vol 48 no 8 pp 3542ndash3548 2000

[92] T Matsuo and S Ito ldquoThe chemical structure of Kaki-tanninfrom immature fruit of the persimmon (Diospyros kaki L)rdquoAgricultural and Biological Chemistry vol 42 no 9 pp 1637ndash1643 1978

[93] S Gorinstein M Zemser M Weisz et al ldquoFluorometric anal-ysis of phenolics in persimmonsrdquo Bioscience Biotechnology andBiochemistry vol 58 no 6 pp 1087ndash1092 1994

[94] S O Lee H J LeeMH Yu H G Im and I S Lee ldquoTotal poly-phenol contents and antioxidant activities of methanol extractsfrom vegetables produced in Ullung Islandrdquo Korean Journal ofFood Science and Technology vol 37 no 2 pp 233ndash240 2005

[95] U V Mallavadhani A K Panda and Y R Rao ldquoPharmacologyand chemotaxonomy of Diospyrosrdquo Phytochemistry vol 49 no4 pp 901ndash951 1998

[96] G Block B Patterson and A Subar ldquoFruit vegetables andcancer prevention a review of the epidemiological evidencerdquoNutrition and Cancer vol 18 no 1 pp 1ndash29 1992

[97] G van Poppel ldquoCarotenoids and cancer an updatewith empha-sis on human intervention studiesrdquo European Journal of Cancervol 29 no 9 pp 1335ndash1344 1993

[98] E Giovannucci A Ascherio E B Rimm M J Stampfer G AColditz and W C Willett ldquoIntake of carotenoids and retino inrelation to risk of prostate cancerrdquo Journal of theNational CancerInstitute vol 87 no 23 pp 1767ndash1776 1995

[99] T Johns R L A Mahunnah P Sanaya L Chapman and TTicktin ldquoSaponins and phenolic content in plant dietary addi-tives of a traditional subsistence community the Batemi ofNgorongoro District Tanzaniardquo Journal of Ethnopharmacologyvol 66 no 1 pp 1ndash10 1999

[100] Y Zhang X Lu Y Zhang L Qin and J Zhang ldquoSulfatedmodification and immunomodulatory activity of water-solublepolysaccharides derived from fresh Chinese persimmon fruitrdquoInternational Journal of Biological Macromolecules vol 46 no1 pp 67ndash71 2010

[101] Y-J Moon and Y-S Cha ldquoEffects of persimmon-vinegar onlipid metabolism and alcohol clearance in chronic alcohol-fedratsrdquo Journal of Medicinal Food vol 11 no 1 pp 38ndash45 2008

[102] H S Ahn T I Jeon J Y Lee S G Hwang Y Lim and D KPark ldquoAntioxidative activity of persimmon and grape seedextract in vitro and in vivordquo Nutrition Research vol 22 no 11pp 1265ndash1273 2002

[103] H Itamurah N Murakami and H Nagamatsu ldquoProperty ofkaki-tannin as a functional composition in persimmon fruitflesh and leaves and its solubility in artificial stomach liquidrdquoin Proceedings of the 27th International Horticultural Congressamp Exhibition (IHC rsquo06) vol 8 pp 265ndash267 August 2006

[104] K A Steinmetz and J D Potter ldquoVegetables fruit and cancerprevention a reviewrdquo Journal of the American Dietetic Associa-tion vol 96 no 10 pp 1027ndash1039 1996

[105] A N Nagappa P A Thakurdesai N V Rao and J SinghldquoAntidiabetic activity ofTerminalia catappa Linn fruitsrdquo Journalof Ethnopharmacology vol 88 no 1 pp 45ndash50 2003

[106] K Datta S Sinha and P Chattopadhyay ldquoReactive oxygenspecies in health and diseaserdquoNationalMedical Journal of Indiavol 13 no 6 pp 304ndash310 2000

[107] R R Holman and R C Turner ldquoOral agents and insulin in thetreatment of NIDDMrdquo in Textbook of Diabetes J Williams Edpp 407ndash469 Blackwell Press Oxford UK 1991

[108] F Giacco and M Brownlee ldquoOxidative stress and diabeticcomplicationsrdquo Circulation Research vol 107 no 9 pp 1058ndash1070 2010

[109] B K Rao M M Kesavulu R Giri and C A Rao ldquoAntidiabeticand hypolipidemic effects ofMomordicacymbalariaHook fruitpowder in alloxan-diabetic ratsrdquo Journal of Ethnopharmacologyvol 67 no 1 pp 103ndash109 1999

[110] J K Grover V Vats V Rathi and S S Dawar ldquoTraditionalIndian anti-diabetic plants attenuate progression of renal dam-age in streptozotocin induced diabetic micerdquo Journal of Ethno-pharmacology vol 76 no 3 pp 233ndash238 2001

[111] R K Gupta A N Kesari P S Murthy R Chandra V Tandonand GWatal ldquoHypoglycemic and antidiabetic effect of ethano-lic extract of leaves of Annona squamosa L in experimentalanimalsrdquo Journal of Ethnopharmacology vol 99 no 1 pp 75ndash81 2005

[112] S Gupta N Ahmad A-L Nieminen andHMukhtar ldquoGrowthinhibition cell-cycle dysregulation and induction of apopto-sis by green tea constituent (-)-epigallocatechin-3-gallate inandrogen-sensitive and androgen-insensitive human prostatecarcinoma cellsrdquoToxicology andApplied Pharmacology vol 164no 1 pp 82ndash90 2000

[113] T Yokozawa Y A Kim H Y Kim Y A Lee and G-I NonakaldquoProtective effect of persimmon peel polyphenol against highglucose-induced oxidative stress in LLC-PK1 cellsrdquo Food andChemical Toxicology vol 45 no 10 pp 1979ndash1987 2007

12 Journal of Chemistry

[114] M S Brewer ldquoNatural antioxidants sources compoundsmechanisms of action and potential applicationsrdquo Comprehen-sive Reviews in Food Science and Food Safety vol 10 no 4 pp221ndash247 2011

[115] K Kawakami H Nishida N Tatewaki Y Nakajima T Konishiand M Hirayama ldquoPersimmon leaf extract inhibits the ATMactivity during DNA damage response induced by Doxorubicinin A549 lung adenocarcinoma cellsrdquo Bioscience Biotechnologyand Biochemistry vol 75 no 4 pp 650ndash655 2011

[116] D Steinberg S Parthasarathy T E Carew J C Khoo and JL Witztum ldquoBeyond cholesterol modifications of low-densitylipoprotein that increase its atherogenicityrdquo The New EnglandJournal of Medicine vol 320 no 14 pp 915ndash924 1989

[117] P M Kris-Etherton and C L Keen ldquoEvidence that the anti-oxidant flavonoids in tea and cocoa are beneficial for cardiovas-cular healthrdquo Current Opinion in Lipidology vol 13 no 1 pp41ndash49 2002

[118] C Manach A Mazur and A Scalbert ldquoPolyphenols and pre-vention of cardiovascular diseasesrdquo Current Opinion in Lipidol-ogy vol 16 no 1 pp 77ndash84 2005

[119] J W Anderson B M Smith and N J Gustafson ldquoHealthbenefits and practical aspects of high-fiber dietsrdquo AmericanJournal of Clinical Nutrition vol 59 no 5 pp 1242ndash1247 1994

[120] D Kromhout A Menotti H Kesteloot and S Sans ldquoPreven-tion of coronary heart disease by diet and lifestyle evidencefrom prospective cross-cultural cohort and intervention stud-iesrdquo Circulation vol 105 no 7 pp 893ndash898 2002

[121] E B Rimm M J Stampfer A Ascherio E Giovannucci G AColditz andWCWillett ldquoVitamin E consumption and the riskof coronary heart disease in menrdquo The New England Journal ofMedicine vol 328 no 20 pp 1450ndash1456 1993

[122] L Dauchet J Ferrieres D Arveiler et al ldquoFrequency of fruitand vegetable consumption and coronary heart disease inFrance and Northern Ireland the prime studyrdquo British Journalof Nutrition vol 92 no 6 pp 963ndash972 2004

[123] S Gorinstein GW Kulasek E Bartnikowska et al ldquoThe effectsof diets supplementedwith either whole persimmon or phenol-free persimmon on rats fed cholesterolrdquo Food Chemistry vol70 no 3 pp 303ndash308 2000

[124] M G L Hertog E J M Feskens P C H HollmanM B Katanand D Kromhout ldquoDietary antioxidant flavonoids and risk ofcoronary heart disease the Zutphen Elderly studyrdquoThe Lancetvol 342 no 8878 pp 1007ndash1011 1993

[125] H Seo B D Jeon andR Sungpil ldquoPersimmon vinegar ripeningwith the mountain-cultivated ginseng ingestion reduces bloodlipids and lowers inflammatory cytokines in obese adolescentsrdquoJournal of Exercise Nutrition and Biochemistry vol 19 no 1 pp1ndash10 2015

[126] R H Liu ldquoPotential synergy of phytochemicals in cancerprevention mechanism of actionrdquo Journal of Nutrition vol 134no 12 supplement pp 3479Sndash3485S 2004

[127] S T Mayne ldquoAntioxidant nutrients and chronic disease use ofbiomarkers of exposure and oxidative stress status in epidemi-ologic researchrdquo Journal of Nutrition vol 133 no 3 pp 933sndash940s 2003

[128] H Tapiero D M Townsend and K D Tew ldquoThe role of caro-tenoids in the prevention of human pathologiesrdquo Biomedicineand Pharmacotherapy vol 58 no 2 pp 100ndash110 2004

[129] J Tao and S L Zhang ldquoMetabolismof carotenoid and its regula-tion in garden croprdquo Journal of Zhejiang University (Agricultureamp Life Sciences) vol 29 pp 585ndash590 2003

[130] W Miki ldquoBiological functions and activities of animal caro-tenoidsrdquo Pure and Applied Chemistry vol 63 no 1 pp 141ndash1461991

[131] H Fujiki ldquoGreen tea health benefits as cancer preventive forhumansrdquo Chemical Record vol 5 no 3 pp 119ndash132 2005

[132] A P George and S Redpath ldquoHealth and medicinal benefits ofpersimmon fruit a reviewrdquo Advances in Horticultural Sciencevol 22 no 4 pp 244ndash249 2008

[133] T Hussain S Gupta V M Adhami and H Mukhtar ldquoGreentea constituent epigallocatechin-3-gallate selectively inhibitsCOX-2 without affecting COX-1 expression in human prostatecarcinoma cellsrdquo International Journal of Cancer vol 113 no 4pp 660ndash669 2005

[134] Y-C Wang and U Bachrach ldquoThe specific anti-cancer activityof green tea (minus)-epigallocatechin-3-gallate (EGCG)rdquo AminoAcids vol 22 no 2 pp 131ndash143 2002

[135] O Takayuki ldquoPersimmons your healthy autumn treatsrdquoAsahikawa Information vol 108 pp 1ndash2 2005

[136] T Fukuda and H Shibata ldquoPersimmon calyx extracts as anti-convulsants and to alleviate the side effects of barbituric acidcompoundsrdquo Patent Japanease Kokai Tokkyo Koho vol 6 pp649ndash653 1994

[137] T Matsuno ldquoXanthophylls as precursors of retinoidsrdquo Pure andApplied Chemistry vol 63 no 1 pp 81ndash88 1991

[138] N Gato A Kadowaki N Hashimoto S-I Yokoyama and KMatsumoto ldquoPersimmon fruit tannin-rich fiber reduces choles-terol levels in humansrdquoAnnals of Nutrition andMetabolism vol62 no 1 pp 1ndash6 2013

[139] A Nagao ldquoAbsorption and function of dietary carotenoidsrdquoForum of Nutrition vol 61 pp 55ndash63 2009

[140] PD Fraser andPM Bramley ldquoThebiosynthesis andnutritionaluses of carotenoidsrdquo Progress in Lipid Research vol 43 no 3 pp228ndash265 2004

[141] D Fusco G Colloca M R Lo Monaco and M Cesari ldquoEffectsof antioxidant supplementation on the aging processrdquo ClinicalInterventions in Aging vol 2 no 3 pp 377ndash387 2007

[142] JM Seddon U Ajan and R D Sperduto ldquoDietary carotenoidsvitamins A C and E and advance age-related macular degen-eration Eye Disease Case Study Grouprdquo Journal of AmericanMedical Association vol 272 no 18 pp 1413ndash1420 1992

[143] B-J An J-H Kwak J-M Park et al ldquoInhibition of enzymeactivities and the antiwrinkle effect of polyphenol isolated fromthe persimmon leaf (Diospyros kaki folium) on human skinrdquoDermatologic Surgery vol 31 no 7 pp 848ndash854 2005

[144] H Arakawa M Takasaki N Tajima H Fukamachi and TIgarashi ldquoAntibacterial activities of persimmon extracts relatewith their hydrogen peroxide concentrationrdquo Biological andPharmaceutical Bulletin vol 37 no 7 pp 1119ndash1123 2014

[145] S D Ladas D Kamberoglou G Karamanolis J Vlachogian-nakos and I Zouboulis-Vafiadis ldquoSystematic review Coca-Cola can effectively dissolve gastric phytobezoars as a first-linetreatmentrdquo Alimentary Pharmacology and Therapeutics vol 37no 2 pp 169ndash173 2013

[146] T J Cifuentes C R Robles P P Parrilla et al ldquoPolyphenols andhealth what compounds are involvedrdquo Nutrition Metabolismand Cardiovascular Diseases vol 20 no 1 pp 1ndash6 2010

[147] J Gaya L Barranco A Llompart J Reyes and A ObradorldquoPersimmon bezoars a successful combined therapyrdquoGastroin-testinal Endoscopy vol 55 no 4 pp 581ndash583 2002

[148] P G Hayes and O D Rotstein ldquoGastrointestinal phytobezoarspresentation and managementrdquo Canadian Journal of Surgeryvol 29 no 6 pp 419ndash420 1986

Journal of Chemistry 13

[149] MM Krausz E ZMoriel A Ayalon D Pode and A L DurstldquoSurgical aspects of gastrointestinal persimmon phytobezoartreatmentrdquoThe American Journal of Surgery vol 152 no 5 pp526ndash530 1986

[150] P Walker-Renard ldquoUpdate on the medicinal management ofphytobezoarsrdquo The American Journal of Gastroenterology vol88 no 10 pp 1663ndash1666 1993

[151] S S Ha H S LeeM K Jung et al ldquoAcute intestinal obstructioncaused by a persimmon phytobezoar after dissolution therapywith Coca-Colardquo The Korean Journal of Internal Medicine vol22 no 4 pp 300ndash303 2007

[152] J Han S Kang R Choue et al ldquoFree radical scavenging effectofDiospyros kaki Laminaria japonica andUndaria pinnatifidardquoFitoterapia vol 73 no 7-8 pp 710ndash712 2002

Submit your manuscripts athttpwwwhindawicom

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Inorganic ChemistryInternational Journal of

Hindawi Publishing Corporation httpwwwhindawicom Volume 2014

International Journal ofPhotoenergy

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Carbohydrate Chemistry

International Journal of

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Journal of

Chemistry

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Advances in

Physical Chemistry

Hindawi Publishing Corporationhttpwwwhindawicom

Analytical Methods in Chemistry

Journal of

Volume 2014

Bioinorganic Chemistry and ApplicationsHindawi Publishing Corporationhttpwwwhindawicom Volume 2014

SpectroscopyInternational Journal of

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

The Scientific World JournalHindawi Publishing Corporation httpwwwhindawicom Volume 2014

Medicinal ChemistryInternational Journal of

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Chromatography Research International

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Applied ChemistryJournal of

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Theoretical ChemistryJournal of

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Journal of

Spectroscopy

Analytical ChemistryInternational Journal of

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Journal of

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Quantum Chemistry

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Organic Chemistry International

ElectrochemistryInternational Journal of

Hindawi Publishing Corporation httpwwwhindawicom Volume 2014

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

CatalystsJournal of

Page 12: Review Article Chemistry and Functionality of Bioactive ...downloads.hindawi.com/journals/jchem/2016/3424025.pdf · Review Article Chemistry and Functionality of Bioactive Compounds

12 Journal of Chemistry

[114] M S Brewer ldquoNatural antioxidants sources compoundsmechanisms of action and potential applicationsrdquo Comprehen-sive Reviews in Food Science and Food Safety vol 10 no 4 pp221ndash247 2011

[115] K Kawakami H Nishida N Tatewaki Y Nakajima T Konishiand M Hirayama ldquoPersimmon leaf extract inhibits the ATMactivity during DNA damage response induced by Doxorubicinin A549 lung adenocarcinoma cellsrdquo Bioscience Biotechnologyand Biochemistry vol 75 no 4 pp 650ndash655 2011

[116] D Steinberg S Parthasarathy T E Carew J C Khoo and JL Witztum ldquoBeyond cholesterol modifications of low-densitylipoprotein that increase its atherogenicityrdquo The New EnglandJournal of Medicine vol 320 no 14 pp 915ndash924 1989

[117] P M Kris-Etherton and C L Keen ldquoEvidence that the anti-oxidant flavonoids in tea and cocoa are beneficial for cardiovas-cular healthrdquo Current Opinion in Lipidology vol 13 no 1 pp41ndash49 2002

[118] C Manach A Mazur and A Scalbert ldquoPolyphenols and pre-vention of cardiovascular diseasesrdquo Current Opinion in Lipidol-ogy vol 16 no 1 pp 77ndash84 2005

[119] J W Anderson B M Smith and N J Gustafson ldquoHealthbenefits and practical aspects of high-fiber dietsrdquo AmericanJournal of Clinical Nutrition vol 59 no 5 pp 1242ndash1247 1994

[120] D Kromhout A Menotti H Kesteloot and S Sans ldquoPreven-tion of coronary heart disease by diet and lifestyle evidencefrom prospective cross-cultural cohort and intervention stud-iesrdquo Circulation vol 105 no 7 pp 893ndash898 2002

[121] E B Rimm M J Stampfer A Ascherio E Giovannucci G AColditz andWCWillett ldquoVitamin E consumption and the riskof coronary heart disease in menrdquo The New England Journal ofMedicine vol 328 no 20 pp 1450ndash1456 1993

[122] L Dauchet J Ferrieres D Arveiler et al ldquoFrequency of fruitand vegetable consumption and coronary heart disease inFrance and Northern Ireland the prime studyrdquo British Journalof Nutrition vol 92 no 6 pp 963ndash972 2004

[123] S Gorinstein GW Kulasek E Bartnikowska et al ldquoThe effectsof diets supplementedwith either whole persimmon or phenol-free persimmon on rats fed cholesterolrdquo Food Chemistry vol70 no 3 pp 303ndash308 2000

[124] M G L Hertog E J M Feskens P C H HollmanM B Katanand D Kromhout ldquoDietary antioxidant flavonoids and risk ofcoronary heart disease the Zutphen Elderly studyrdquoThe Lancetvol 342 no 8878 pp 1007ndash1011 1993

[125] H Seo B D Jeon andR Sungpil ldquoPersimmon vinegar ripeningwith the mountain-cultivated ginseng ingestion reduces bloodlipids and lowers inflammatory cytokines in obese adolescentsrdquoJournal of Exercise Nutrition and Biochemistry vol 19 no 1 pp1ndash10 2015

[126] R H Liu ldquoPotential synergy of phytochemicals in cancerprevention mechanism of actionrdquo Journal of Nutrition vol 134no 12 supplement pp 3479Sndash3485S 2004

[127] S T Mayne ldquoAntioxidant nutrients and chronic disease use ofbiomarkers of exposure and oxidative stress status in epidemi-ologic researchrdquo Journal of Nutrition vol 133 no 3 pp 933sndash940s 2003

[128] H Tapiero D M Townsend and K D Tew ldquoThe role of caro-tenoids in the prevention of human pathologiesrdquo Biomedicineand Pharmacotherapy vol 58 no 2 pp 100ndash110 2004

[129] J Tao and S L Zhang ldquoMetabolismof carotenoid and its regula-tion in garden croprdquo Journal of Zhejiang University (Agricultureamp Life Sciences) vol 29 pp 585ndash590 2003

[130] W Miki ldquoBiological functions and activities of animal caro-tenoidsrdquo Pure and Applied Chemistry vol 63 no 1 pp 141ndash1461991

[131] H Fujiki ldquoGreen tea health benefits as cancer preventive forhumansrdquo Chemical Record vol 5 no 3 pp 119ndash132 2005

[132] A P George and S Redpath ldquoHealth and medicinal benefits ofpersimmon fruit a reviewrdquo Advances in Horticultural Sciencevol 22 no 4 pp 244ndash249 2008

[133] T Hussain S Gupta V M Adhami and H Mukhtar ldquoGreentea constituent epigallocatechin-3-gallate selectively inhibitsCOX-2 without affecting COX-1 expression in human prostatecarcinoma cellsrdquo International Journal of Cancer vol 113 no 4pp 660ndash669 2005

[134] Y-C Wang and U Bachrach ldquoThe specific anti-cancer activityof green tea (minus)-epigallocatechin-3-gallate (EGCG)rdquo AminoAcids vol 22 no 2 pp 131ndash143 2002

[135] O Takayuki ldquoPersimmons your healthy autumn treatsrdquoAsahikawa Information vol 108 pp 1ndash2 2005

[136] T Fukuda and H Shibata ldquoPersimmon calyx extracts as anti-convulsants and to alleviate the side effects of barbituric acidcompoundsrdquo Patent Japanease Kokai Tokkyo Koho vol 6 pp649ndash653 1994

[137] T Matsuno ldquoXanthophylls as precursors of retinoidsrdquo Pure andApplied Chemistry vol 63 no 1 pp 81ndash88 1991

[138] N Gato A Kadowaki N Hashimoto S-I Yokoyama and KMatsumoto ldquoPersimmon fruit tannin-rich fiber reduces choles-terol levels in humansrdquoAnnals of Nutrition andMetabolism vol62 no 1 pp 1ndash6 2013

[139] A Nagao ldquoAbsorption and function of dietary carotenoidsrdquoForum of Nutrition vol 61 pp 55ndash63 2009

[140] PD Fraser andPM Bramley ldquoThebiosynthesis andnutritionaluses of carotenoidsrdquo Progress in Lipid Research vol 43 no 3 pp228ndash265 2004

[141] D Fusco G Colloca M R Lo Monaco and M Cesari ldquoEffectsof antioxidant supplementation on the aging processrdquo ClinicalInterventions in Aging vol 2 no 3 pp 377ndash387 2007

[142] JM Seddon U Ajan and R D Sperduto ldquoDietary carotenoidsvitamins A C and E and advance age-related macular degen-eration Eye Disease Case Study Grouprdquo Journal of AmericanMedical Association vol 272 no 18 pp 1413ndash1420 1992

[143] B-J An J-H Kwak J-M Park et al ldquoInhibition of enzymeactivities and the antiwrinkle effect of polyphenol isolated fromthe persimmon leaf (Diospyros kaki folium) on human skinrdquoDermatologic Surgery vol 31 no 7 pp 848ndash854 2005

[144] H Arakawa M Takasaki N Tajima H Fukamachi and TIgarashi ldquoAntibacterial activities of persimmon extracts relatewith their hydrogen peroxide concentrationrdquo Biological andPharmaceutical Bulletin vol 37 no 7 pp 1119ndash1123 2014

[145] S D Ladas D Kamberoglou G Karamanolis J Vlachogian-nakos and I Zouboulis-Vafiadis ldquoSystematic review Coca-Cola can effectively dissolve gastric phytobezoars as a first-linetreatmentrdquo Alimentary Pharmacology and Therapeutics vol 37no 2 pp 169ndash173 2013

[146] T J Cifuentes C R Robles P P Parrilla et al ldquoPolyphenols andhealth what compounds are involvedrdquo Nutrition Metabolismand Cardiovascular Diseases vol 20 no 1 pp 1ndash6 2010

[147] J Gaya L Barranco A Llompart J Reyes and A ObradorldquoPersimmon bezoars a successful combined therapyrdquoGastroin-testinal Endoscopy vol 55 no 4 pp 581ndash583 2002

[148] P G Hayes and O D Rotstein ldquoGastrointestinal phytobezoarspresentation and managementrdquo Canadian Journal of Surgeryvol 29 no 6 pp 419ndash420 1986

Journal of Chemistry 13

[149] MM Krausz E ZMoriel A Ayalon D Pode and A L DurstldquoSurgical aspects of gastrointestinal persimmon phytobezoartreatmentrdquoThe American Journal of Surgery vol 152 no 5 pp526ndash530 1986

[150] P Walker-Renard ldquoUpdate on the medicinal management ofphytobezoarsrdquo The American Journal of Gastroenterology vol88 no 10 pp 1663ndash1666 1993

[151] S S Ha H S LeeM K Jung et al ldquoAcute intestinal obstructioncaused by a persimmon phytobezoar after dissolution therapywith Coca-Colardquo The Korean Journal of Internal Medicine vol22 no 4 pp 300ndash303 2007

[152] J Han S Kang R Choue et al ldquoFree radical scavenging effectofDiospyros kaki Laminaria japonica andUndaria pinnatifidardquoFitoterapia vol 73 no 7-8 pp 710ndash712 2002

Submit your manuscripts athttpwwwhindawicom

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Inorganic ChemistryInternational Journal of

Hindawi Publishing Corporation httpwwwhindawicom Volume 2014

International Journal ofPhotoenergy

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Carbohydrate Chemistry

International Journal of

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Journal of

Chemistry

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Advances in

Physical Chemistry

Hindawi Publishing Corporationhttpwwwhindawicom

Analytical Methods in Chemistry

Journal of

Volume 2014

Bioinorganic Chemistry and ApplicationsHindawi Publishing Corporationhttpwwwhindawicom Volume 2014

SpectroscopyInternational Journal of

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

The Scientific World JournalHindawi Publishing Corporation httpwwwhindawicom Volume 2014

Medicinal ChemistryInternational Journal of

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Chromatography Research International

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Applied ChemistryJournal of

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Theoretical ChemistryJournal of

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Journal of

Spectroscopy

Analytical ChemistryInternational Journal of

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Journal of

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Quantum Chemistry

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Organic Chemistry International

ElectrochemistryInternational Journal of

Hindawi Publishing Corporation httpwwwhindawicom Volume 2014

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

CatalystsJournal of

Page 13: Review Article Chemistry and Functionality of Bioactive ...downloads.hindawi.com/journals/jchem/2016/3424025.pdf · Review Article Chemistry and Functionality of Bioactive Compounds

Journal of Chemistry 13

[149] MM Krausz E ZMoriel A Ayalon D Pode and A L DurstldquoSurgical aspects of gastrointestinal persimmon phytobezoartreatmentrdquoThe American Journal of Surgery vol 152 no 5 pp526ndash530 1986

[150] P Walker-Renard ldquoUpdate on the medicinal management ofphytobezoarsrdquo The American Journal of Gastroenterology vol88 no 10 pp 1663ndash1666 1993

[151] S S Ha H S LeeM K Jung et al ldquoAcute intestinal obstructioncaused by a persimmon phytobezoar after dissolution therapywith Coca-Colardquo The Korean Journal of Internal Medicine vol22 no 4 pp 300ndash303 2007

[152] J Han S Kang R Choue et al ldquoFree radical scavenging effectofDiospyros kaki Laminaria japonica andUndaria pinnatifidardquoFitoterapia vol 73 no 7-8 pp 710ndash712 2002

Submit your manuscripts athttpwwwhindawicom

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Inorganic ChemistryInternational Journal of

Hindawi Publishing Corporation httpwwwhindawicom Volume 2014

International Journal ofPhotoenergy

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Carbohydrate Chemistry

International Journal of

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Journal of

Chemistry

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Advances in

Physical Chemistry

Hindawi Publishing Corporationhttpwwwhindawicom

Analytical Methods in Chemistry

Journal of

Volume 2014

Bioinorganic Chemistry and ApplicationsHindawi Publishing Corporationhttpwwwhindawicom Volume 2014

SpectroscopyInternational Journal of

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

The Scientific World JournalHindawi Publishing Corporation httpwwwhindawicom Volume 2014

Medicinal ChemistryInternational Journal of

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Chromatography Research International

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Applied ChemistryJournal of

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Theoretical ChemistryJournal of

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Journal of

Spectroscopy

Analytical ChemistryInternational Journal of

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Journal of

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Quantum Chemistry

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Organic Chemistry International

ElectrochemistryInternational Journal of

Hindawi Publishing Corporation httpwwwhindawicom Volume 2014

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

CatalystsJournal of

Page 14: Review Article Chemistry and Functionality of Bioactive ...downloads.hindawi.com/journals/jchem/2016/3424025.pdf · Review Article Chemistry and Functionality of Bioactive Compounds

Submit your manuscripts athttpwwwhindawicom

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Inorganic ChemistryInternational Journal of

Hindawi Publishing Corporation httpwwwhindawicom Volume 2014

International Journal ofPhotoenergy

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Carbohydrate Chemistry

International Journal of

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Journal of

Chemistry

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Advances in

Physical Chemistry

Hindawi Publishing Corporationhttpwwwhindawicom

Analytical Methods in Chemistry

Journal of

Volume 2014

Bioinorganic Chemistry and ApplicationsHindawi Publishing Corporationhttpwwwhindawicom Volume 2014

SpectroscopyInternational Journal of

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

The Scientific World JournalHindawi Publishing Corporation httpwwwhindawicom Volume 2014

Medicinal ChemistryInternational Journal of

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Chromatography Research International

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Applied ChemistryJournal of

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Theoretical ChemistryJournal of

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Journal of

Spectroscopy

Analytical ChemistryInternational Journal of

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Journal of

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Quantum Chemistry

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

Organic Chemistry International

ElectrochemistryInternational Journal of

Hindawi Publishing Corporation httpwwwhindawicom Volume 2014

Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014

CatalystsJournal of