Evaluation of Chemical Constituents and Important ...ReviewArticle Evaluation of Chemical...

Review ArticleEvaluation of Chemical Constituents and Important Mechanismof Pharmacological Biology in Dendrobium Plants

Yau Lam1 Tzi Bun Ng2 Ren Ming Yao1 Jun Shi1 Kai Xu1

Stephen Cho Wing Sze1 and Kalin Yanbo Zhang1

1School of Chinese Medicine LKS Faculty of Medicine The University of Hong Kong 10 Sassoon Road Hong Kong2School of Biomedical Sciences Faculty of Medicine The Chinese University of Hong Kong Shatin NT Hong Kong

Correspondence should be addressed to Tzi Bun Ng b021770mailservcuhkeduhk Stephen Cho Wing Sze stephenshkuhkand Kalin Yanbo Zhang ybzhanghkucchkuhk

Received 24 November 2014 Accepted 9 February 2015

Academic Editor Wagner Vilegas

Copyright copy 2015 Yau Lam et alThis is an open access article distributed under the Creative Commons Attribution License whichpermits unrestricted use distribution and reproduction in any medium provided the original work is properly cited

Dendrobium species commonly known as ldquoShihurdquo or ldquoHuangcaordquo represents the second largest genus of Orchidaceae which areused commonly as tonic herbs and healthy food in many Asian countries The aim of this paper is to review the history chemistryand pharmacology of differentDendrobium species on the basis of the latest academic literatures found in Google Scholar PubMedSciencedirect Scopus and SID

1 Introduction

The origin of orchids (Orchidaceae) probably has to bebackdated to 120 million years ago It is the largest familygroup among angiosperms as well as themost highly evolvedfamily of the flowering plants with approximately 25000 to35000 species under 750 to 900 genera [1ndash4] Dendrobiumspecies commonly known as ldquoShihurdquo or ldquoHuangcaordquo isthe second largest genus in Orchidaceae Most Dendrobiumspecies grow best in relatively high and mountainous areasat 1400ndash1600m above sea level at a mild temperature andin a humid and foggy environment Characterized by abroad geographical distribution which allows Dendrobiumspecies to grow into tremendous diversities producing a largenumber of interspecific hybrids with different morphologicalfeatures they are widely distributed in Asia Australia andEurope for instance in India Sri Lanka China JapanKorea New Guinea and New Caledonia [5] In the earlyage using molecular approaches would delimit the subtribe-Dendrobiinae affecting approximately 1100 species (900 inDendrobium Sw) from Indo-Asian and Pacific regions [6 7]and more than 1200 species in Australasia are from variousDendrobium species Today Indo-Asian and Pacific regionshave one of the largest and most diverse and taxonomicallyproblematic orchid groups [8] Interestingly there has been

a long history of the usage of first-rate herbs and folktraditional herbs in India and China [9]

Since the ancient times (600 BC) in India the oldestreferences regarding the use of medicinal herbs are foundin the Sanskrit literature namely ldquoCharaka Samhitardquo Theearliest treatise on ldquoAyurvedardquo describes the property of plantdrugs and their uses In the Ayurvedic system of medicineFlickingeria macraei is used in ldquoAyurvedardquo It is commonlynamed as ldquojeevantirdquo and is used as an astringent to thebowels as an aphrodisiac and in asthma and bronchitis[10] Other commonly used orchid drugs in the Ayurvedicsystem are salem including jewanti (Dendrobium alpestre)Similarly it is the first time for China to regard orchids asherbal medicines [11] The Emperor ldquoShen-Nungrdquo advised onthe medicinal properties of Dendrobium species in ldquomateriamedicardquo in the 28th century BC [12] As early as 200 BC theChinese pharmacopoeia ldquoThe Sang Nung Pen Tsao Chingrdquomentioned Dendrobium as a source of tonic astringentanalgesic and anti-inflammatory substances [13] In SongDynasty (960ndash1279 AD) It mentioned the medicinal uses oforchids namely Dendrobium species according A Diagnosisof Medical Herbs from the ldquoZheng Lei Ben Caordquo In MingDynasty (1368ndash1644) many references on the use of orchidsas medicinal herbs were available [14]

Hindawi Publishing CorporationEvidence-Based Complementary and Alternative MedicineVolume 2015 Article ID 841752 25 pageshttpdxdoiorg1011552015841752

2 Evidence-Based Complementary and Alternative Medicine

2 The Chemical Compounds ofDendrobium Species

The stem of Dendrobium species has been used in traditionalChinesemedicine as a tonic and antipyretic since ancient daysfor treating human disorders However misidentificationand adulteration led to a loss of therapeutic potency andpotential intoxication For decades fast developingmoleculartechniques using DNA fingerprinting DNA sequencing andDNA microarray have been applied extensively to authen-ticate Chinese medicinal materials including various Den-drobium species [15] namely D aphyllum D candidum Dchrysanthum D densiflorum D huoshanense D gratiosissi-mumD longicornuD nobileD secundumD chrysotoxumD crystallinum D fimbriatum and others [16] In the earlyyears Williams and Harborne conducted a major surveyof leaf flavonoids at the Plant Science Laboratories of theUniversity of Reading in UK They conducted research on142 species belonging to 75 genera and found that the mostcommon constituents were flavone C-glycoside and flavonols[17] Since then about 100 compounds from 42 Dendrobiumspecies including 32 alkaloids 6 coumarins 15 bibenzyls 4fluorenones 22 phenanthrenes and 7 sesquiterpenoids con-stituents have been discussed and reviewed [18ndash31] (Table 1)To date various Dendrobium species are known to producea variety of secondary metabolites The biological activitiesand pharmacological actions of all of these compounds wereinvestigated in detail [32ndash39]

3 The Pharmacological Effects ofDendrobium Species

31 Antioxidant Activities Oxidative stress is induced byfree radicals that participate in a variety of chemical reac-tions with biomolecules leading to a pathological conditionReactive oxygen species (ROS) is one of the major freeradicals It mainly comprises superoxide (O

2

minus) and nitricoxide (NO) radicals including (1) catalase (CAT) (2) perox-idase (POD) (3) ascorbate peroxidase (APX) (4) 221015840-azino-bis(3-ethylbenzothiazoline-6-sulphonic acid) or ABTS (5)hydroxyl and (6) 11-diphenyl-2-picrylhydrazyl (DPPH) rad-icals During these processes it was found that the content ofmalondialdehyde (MDA) was increased

However cells possess two distinctive antioxidant defensesystems to counteract the damage including enzymatic anti-oxidants and nonenzymatic antioxidants Enzymatic antiox-idants comprise catalase superoxide dismutase (SOD) gluta-thione peroxidase (GPx) and others associated with en-zymesmolecules Nonenzymatic antioxidants include ascor-bic acid (vitamin C) 120572-tocopherol (vitamin E) and 120573-carotene which play a key role in removing reactive oxygenspecies

Oxidative stresses have been classified as exogenousfactors and endogenous factors Factors related to environ-mental stress includewatersoil drought stress chilling injurystress and soundwave stressTherewere studies on the effectsof cold storage on cut Dendrobium inflorescences showingthat chilling injury symptoms for floral buds and open flowers

ofDendrobium could lead to oxidative stress stemming fromthe production of reactive oxygen species In this process thedecrease of cellular functions by peroxidation of membranelipids when lipoxygenase enzymes are degraded in cellsHowever this physiological process in floral buds and openflowers is part of antioxidant defense systems which candecrease the content of oxygen free radicals and other oxygencompounds It indicates the protective cellular functions andantioxidant capacity This is an adaptive nature to ensuresome plants survive in the freezing winter [62]

In addition soundwave stress is one of the environmentalstresses similar to the low temperature stress Studies ofthe effects of sound wave stress on D candidum yieldeddata indicated it as a lipid peroxidation parameter whichcan regulate the levels of MDA Firstly the MDA content indifferent organs is increased and then declines afterwardswhich will then be followed by an increase again That givesa net increase of the level of MDA It was noted that theMDA level appears to be the lowest when the activities ofantioxidant enzymes are the highest However the levelsof MDA are yet to be fully understood We believe theantioxidant enzymes could protect plant cells from oxidativedamage in sound wave stress [63] However the correlationbetween themechanisms of antioxidant action and the soundwave stress and chilling injury stress has yet to be identified

Water deficit caused by soil drought is one of the mostfrequent environmental stresses The effects of exogenousdrought menace prompting further increases in the activityof ROS and decrease in themalondialdehyde (MDA) contentto prevent the breakage of DNA and protein degradationfrom doing damage to plant life [64] It is well knownthat nitric oxide (NO) is a ubiquitous signal moleculeinvolved in many life processes of plants seed germinationhypocotyl elongation leaf expansion root growth lateralroots initiation and apoptosis and so forth It is also involvedin multiple plant responses to environmental stress Datademonstrated that at lower concentrations of exogenous NOwith 50mmol Lminus1 SNP the activation of POD SOD and CATwas significantly increased and the MDA content decreasedwith 50Ml SNPNO could protect D huoshanense against theoxidative insult caused by a drought stress meanwhile a highlevel of RWCcan bemaintained Furthermore it suggests thatthe molecular messenger NO can trigger epigenetic variationand increase the demethylation ratio ofmethylated sites forDhuoshanense by using DNA analysis These results may implythat the expression of some genes is involved in the responseto drought stress triggered by NO [65]

Numerous Dendrobium species such as D nobile D den-neanum D huoshanense D chrysotoxum D moniliforme Dtosaense D linawianum D candidum D loddigesii and Dfimbriatum have polysaccharides as the active compoundsPolysaccharides play important roles in many biologicalprocesses and are used to treat various diseases [66 67]Polysaccharides isolated from D nobile D huoshanense Dchrysotoxum andD fimbriatum species manifest antioxidantand free radical scavenging activities D nobile polysac-charide displayed the highest scavenging activity towardhydroxyl ABTS and DPPH free radicals [40 68 69] How-everD fimbriatum polysaccharide has significant scavenging

Evidence-Based Complementary and Alternative Medicine 3

Table1Th

ecom

poun

dsof

vario

usDendrobium

species

Species

Con

stituent

Chem

icalform

ula

Structures

ofcompo

und

Reference

Da

moenu

mBibenzylsd

erivatives

Amoenylin

R 1=R 3

=MeR 2

=OHR

4=HR

5=OMe

1

23

456

AB

120572

120572998400

1998400

2998400

3998400

4998400

5998400

6998400

OR 1

R 2

OR 3

R 4

R 5[19

]

Isoamoenylin

R 1=R 3

=MeR 2

=OMeR 4

=OHR

5=H

Moscatilin

(analogues)

mdash341015840-D

ihydroxy-5-m

etho

xybibenzyl

mdashmdash

R 1=R 2

=R 4

=HR

3=MeR 5

=OH

mdashR 1

=R 3

=MeR 2

=OHR

4=HR

5=OMe

mdashR 1

=R 3

=MeR 2

=OAc

R4=HR

5=OMe

mdashR 1

=R 3

=MeR 2

=OMeR 4

=OAc

R5=H

mdashR 1

=Ac

R2=R 4

=HR

3=MeR 5

=OAc

mdashR 1

=R 3

=MeR 2

=R 5

=OHR

4=OMe

mdashR 1

=R 3

=MeR 2

=R 4

=OMeR 5

=OH

mdashR 1

=R 3

=MeR 2

=R 5

=OMeR 4

=OAc

mdashR 1

=R 2

=R 5

=HR

3=MeR 4

=OH

mdashR 1

=Ac

R2=R 5

=HR

3=MeR 4

=OAc

mdashR 1

=R 2

=R 3

=R 4

=HR

5=OH

Dc

andidu

mBibenzylsd

erivatives

DendrocandinC

((S)-344-tr

ihydroxy-5120572-dim

etho

xybibenzyl)

DendrocandinD

((S)-344-tr

ihydroxy-5-m

etho

xy-120572-ethoxybibenzyl)

DendrocandinE

(3344-te

trahydroxy-5-m

etho

xybibenzyl)

R 1=R 2

=R 5

=OHR

3=R 6

=OCH

3R 4

=H

R 1=R 2

=R 5

=OHR

3=OCH

3R 6

=OCH

2CH

3R 4

=H

R 1=R 2

=R 4

=R 5

=OHR

3=OCH

3R 6

=H

1

23

4

56

120572

120572998400

1998400

2998400

3998400

4998400

5998400

6998400

R 1

R 2

R 3

R 4

R 5

R 6

[20]

Amotin

(type

1sesquiterpenoids)

mdash

HO

OH

O

O

OO

Me

HH

[19]


Table1Con

tinued

Species

Con

stituent

Chem

icalform

ula

Structures

ofcompo

und

Reference

Amoenin(ty

pe2sesquiterpenoids)

mdash

HO HO

OH

O Me

H

OO

[19]

Flaccidin(910

-dihydroph

enanthropyran)

mdash

O

HO

OM

e

OH

[19]

Bibenzylsd

erivatives

44-Dihydroxy-35-dim

etho

xybibenzyl

34-Dihydroxy-54dimetho

xybibenzyl

3-O-M

ethylgigantol

Dendrop

heno

lGigantol

New

compo

unds

DendrocandinA

((R)-34-dihydroxy-54120572-tr

imetho

xybibenzyl)

R 2=R 5

=OHR

1=R 3

=OCH

3R 4

=R 6

=OH

R 1=R 2

=OHR

3=R 5

=OCH

3R 4

=R 6

=OH

R 1=OHR

3=R 4

=R 5

=OCH

3R 2

=R 6

=H

R 2=R 4

=R 5

=OHR

1=R 3

=OCH

3R 6

=H

R 1=R 5

=OHR

3=R 4

=OCH

3R 2

=R 6

=H

R 1=R 2

=OHR

3=R 5

=R 6

=OCH

3R 4

=H

1

23

4

56

120572

120572998400

1998400

2998400

3998400

4998400

5998400

6998400

R 1

R 2

R 3

R 4

R 5

R 6

[21]

DendrocandinB

(4-[2-[(2S3S)-3-(4-hydroxy-35-dimetho

xyph

enyl)-2-

hydroxym

ethyl-8

-metho

xy-23-

dihydrob

enzo[14]dioxin-6-yl]ethyl]-1-m

etho

xyl

benzene)

mdashOO

12

345

6

120572120572998400

1998400

2998400

3998400 4998400

5998400

6998400

1998400998400

2998400998400

3998400998400 4998400998400

5998400998400

6998400998400

7998400998400

8998400998400

9998400998400

H3CO

OCH

3

OCH

3

OCH

3

OH

OH

[21]


Table1Con

tinued

Species

Con

stituent

Chem

icalform

ula

Structures

ofcompo

und

Reference

Da

phyllum

Aromaticcompo

unds

Flavanthrin

mdash

OCH

3

OCH

3

OH

OH

HO

HO

[22]

Coelonin

Iusia

nthridin

R 1=OHR

2=OMe

R 1=OMeR 2

=OH

HO

R 1

R 2

[22]

Moscatin

mdashO

H

OH

OM

e

[22]

Gigantol

Batatasin

III

R 1=R 3

=OMeR 2

=OH

R 1=OHR

2=HR

3=OMe

HO

R 1

R 2

R 3

[22]


Table1Con

tinued

Species

Con

stituent

Chem

icalform

ula

Structures

ofcompo

und

Reference

Dibutylph

thalate

Diisob

utylph

thalate

R=CH

2CH

2CH

2CH

3R=CH

2CH(C

H3)

2

CCO

R

OR

O O

[22]

P-hydroxyphenylpropion

icmethyleste

rmdash

COO

Me

OH

[22]

Dc

ariniferum

Phenanthrenequ

inon

e

Dendron

one(5-hydroxy-7-metho

xy-910

-dihydro-14-

phenanthrenequ

inon

e)mdash

O

MeO

OH

2

34

110

a8a

87

65

4b4a

109

O

[23]

Dc

hrysotoxum

Aromaticorganicc

ompo

unds

(Fluorenon

es)

Dendrofl

orin

DenchrysanA

R 1=HR

2=OH

R 1=OHR

2=H

O

OCH

3

OH

OH

R 1R 2

[24]

145-tr

ihydroxy-7-m

etho

xy-9H-fluo

ren-9-on

emdash

OCH

3

OH

OH 4

56 7

89

123

8a9a4a

4b

OH

O

[24]


Table1Con

tinued

Species

Con

stituent

Chem

icalform

ula

Structures

ofcompo

und

Reference

(Fluorenol)

(9R)-4metho

xy-9H-fluo

rene-259-tr

iol

R=H

OR

OR

RO

OM

e

[25]

Phenanthrene

27-dihydroxy-8m

etho

xyph

enanthro[45-bcd]pyran-

5(5H

)-on

emdash

O

O

OH

OH

OM

e

[25]

Dd

ensifl

orum

Bibenzyl

Densifl

orolA

mdash

O

MeO

O

OH

1

2

33

a4

5

6

77

a

1998400

2998400

1998400998400

2998400998400

3998400998400

49984009984005998400998400

6998400998400

7998400998400

[26]

Phenanthrenedion

e

Densifl

orolB

R=H

HO

1

2

3

4a 10

a8

a

4b

45

6

910

7

8

OM

e

O

O

R

[26]


Table1Con

tinued

Species

Con

stituent

Chem

icalform

ula

Structures

ofcompo

und

Reference

Dendrofl

orin

R=OH

OH

OH

OR1

234

a

9a

8a

4b

45

6

9

7

8OM

e

[26]

Know

nas

oleano

licacid

andb-sitosterolcom

poun

ds

(A)D

engibsin

R=H

OH

OH

OR1

23

9a

8a

4a

4b

45

6

9

7

8OM

e

[26]

(B)C

yprip

edin

R=OMe

O

RO

HO

OM

e1

2

3

8a

4a

4b

45

6

910

10a

7

8

[26]

(C)G

igantol

(D)M

oscatilin

(E)T

ristin

R=OHR

=HR

=OMe

R=R=OMeR=OH

R=R=OHR

=H

R

OH

OM

e

R998400 R998400998400

[26]

(F)N

aringenin

(G)H

omoerio

dictyol

R=H

R=OMe

OOO

H

OH

HO

R[26]


Table1Con

tinued

Species

Con

stituent

Chem

icalform

ula

Structures

ofcompo

und

Reference

(H)M

oscatin

mdashO

H

HO

OM

e

[26]

(I)2

6-dihydroxy-157-trim

etho

xyph

enanthrene

mdashO

H

HO

OM

e

OM

e

MeO

[26]

(J)4

7-dihydroxy-2-metho

xy-910

-dihydroph

enanthrene

mdash

OH

HO

OM

e[26]

(K)S

coparone

(L)S

copo

letin

(M)A

yapin

R=R=OMe

R=OMeR=OH

R+R=OCH

2OO

O

R R998400[26]

Dlongicornu

Mon

oaromatic

compo

unds

Bis(2-ethylhexyl)phthalate

Dibutylph

thalate

CH2C

H(C

2H5)(C

H2)

3CH

3(C

H2)

3CH

3

O O

OR

OR

[27]

Ethylh

aematom

mate

C 11H

12O

5

HO

CHO

OH

COO

C 2H5

CH3

[27]


Table1Con

tinued

Species

Con

stituent

Chem

icalform

ula

Structures

ofcompo

und

Reference

MethylB

-orcinolcarboxylate

C 10H

12O

4

HO

OH

CH3

H3C

COO

CH3

[27]

N-D

ocosyltra

ns-fe

rulate

Ferulaldehyde

R=CO

OCH

2(CH

2)20CH

3R=CH

O

R

HH

OH

OCH

3

[27]

Dn

obile

Sesquiterpenes

(Dendron

obilins

A)

Cop

acam

phane-type

(1R2R

4S5S6S8S9R)-28-

Dihydroxycopacamph

an-15-on

eH H

H

H

H

O

HO

OH

(R)

11 109

7

15

1214

13

16 5

(R) (R)

(S)

(S)

(S)

(S)

[28]

Picrotoxane-type

(2b3b4b5b)-2411-Trihydroxy-picrotoxano

-3(15)-lacton

e

H

H H

H

H

O O

HO

OH

OH

1214

15

133

11

110

9

6[28]


Table1Con

tinued

Species

Con

stituent

Chem

icalform

ula

Structures

ofcompo

und

Reference

Picrotoxane-type

(2b3b5b9a11b)-211-Epo

xy-91113

-trihydroxypicrotoxano3(15)-la

cton

e

H

HHH

H H

OO O

HO H

O

OH

123

14

15

56

9 1

11 10 13

[28]

Picrotoxane-type

(2b3b5b12Rlowast

)-21113

-Trih

ydroxy-

picrotoxano-3(15)-lacton

e

H

HHH

H H

O O

HO H

O

OH

1214

15

567

91

11

10 13(R

lowast)

[28]

Picrotoxane-type

(2b3b5b12Slowast)21113

-Trih

ydroxy-


eO O

H HH

HH

H

HO H

O

OH

1215569

110

11

7

1314

(Slowast

)

[28]


Table1Con

tinued

Species

Con

stituent

Chem

icalform

ula

Structures

ofcompo

und

Reference

Picrotoxane-type

(2b3b5b9a)-10

-Cyclo-21113

-trihydroxy-


eO O

H HH

H H HO

HO

OH

121556

9 110

11

7

1314

[28]

Muu

rolene-ty

pe(9b10a)-M

uurol-4

-ene-910

11-tr

iol

H

HHH

HO

OH

OH

12

15 69

110

11

4

2

1314

[28]

Allo

arom

adendrene-type

(10a)-A

lloarom

adendrene-1012

14-tr

iol

H

H

HH

H

HO

OH

OH 12

15

6

91

10

1142

1314

5[28]

Cyclo

copacamph

ane-type

(5b)-C

yclocopacamph

ane-51215

-triol

H

1

14

10

7 24

35

6

1512

1311 H

HH

H

H

HO

OH

OH

[28]

Evidence-Based Complementary and Alternative Medicine 13Ta

ble1Con

tinued

Species

Con

stituent

Chem

icalform

ula

Structures

ofcompo

und

Reference

Bibenzylderiv

atives

Dendron

opheno

lA221015840991015840-Tetrametho

xy131015840141015840-peroxy-111015840-

bis(bibenzyl)-661015840-diol)

OO

MeO

MeO

OM

e

OM

eHO

OH

12

3 4

56

7

8

9

10

1112

13

14

15

161998400

2998400

3998400

4998400

5998400

6998400

7998400

8998400

9998400

10998400

11998400

12998400

13998400

14998400

15998400

16998400

[29]

Dendron

opheno

lB1-(2101584061015840-D

imetho

xy7101584081015840-peroxyphenyl-

prop

yl)-29-dimetho

xybibenzyl-691015840-diol)

O

OH

OH

OM

eO

MeO

OM

e

OM

e 12

3 4

56

7

8

9

10

1112

13

14

15

161998400

2998400

3998400

4998400

5998400

6998400

7998400

8998400 9998400

10998400

11998400

[29]

Dthyrsiflorum

Bi-bicyclic

andbi-tr

icyclic

compo

unds

Denthyrsin

[3-(5101584061015840-D

imetho

xybenzofuran-21015840-yl)-67-

dimetho

xy-2H-chrom

en-2-one

O

OO 1

23

45

678

9 10

1998400

2998400

3998400

4998400

59984006998400

7998400

8998400

9998400

H3CO

H3CO

OCH

3

OCH

3

[30]

Denthyrsin

ol(451015840-D

imetho

xy-[111015840]biphenanthrenyl-

25410158407-tetraol

OCH

3

OCH

3

OH

OH

OH

OH

1

2

34

4a

4b

56

7

88

a

910

10a

1998400 3998400

2998400

49984004

a9984004

b998400

5998400

6998400

7998400

8998400

8a998400

9998400

10998400

10a998400

[30]


Table1Con

tinued

Species

Con

stituent

Chem

icalform

ula

Structures

ofcompo

und

Reference

Denthyrsin

one

(74101584071015840-Trih

ydroxy-22101584081015840-tr

imetho

xy-

[511015840]biphenanthrenyl-14-dione)

OCH

3

O

O

OH

OH

OH

12

34

4a

4b

56

7

88

a910 10

a

1998400

2998400 3998400

49984004

a9984004

b998400

5998400

69984007998400

8998400

8a9984009998400

10998400

10a998400

H3CO

H3CO

[30]

Denthyrsin

in15

7-Trim

etho

xyph

enanthrene-26-diol

OCH

3

OH

H3CO

H3CO

HO

[30]

Scop

aron

emdash

OO

H3CO

H3CO

[30]

b-Sitoste

rol

mdash

OCH

3

OH

OH

[30]

Daucoste

rol

mdash

OCH

3

OH

OH

[30]


Table 2 Polysaccharides DDP1-1 DDP2-1 and DDP3-1 isolatedfrom D denneanum and DNP1-1 DNP2-1 DNP3-1 and DNP4-2isolated from D nobile

ABTSradicals

Hydroxylradicals

DPPHradicals

D denneanumDDP1-1 (LW) (LW) (LW)DDP2-1 (LW) (HH) (HH)DDP3-1 (LW) (LW) (LW)

D nobileDNP1-1 (LW) (LW) (LW)DNP2-1 (LW) (LW) (LW)DNP3-1 (LW) (LW) (LW)DNP4-2 (HH) (HH) (HH)

lowastNotes Low (LW) High (HH)Up the table the antioxidant effect ofDNP4-2 onABTS hydroxyl andDPPHfree radicals suggesting the levels of DNP4-2 higher than DNP1-1 DNP2-1and DNP3-1 however the antioxidant effects of DDP2-1 on hydroxyl andDPPH free radicals were higher than ABTS free radicals Moreover theDDP1-1 and DDP 3-1 on inhibitory effect were low than other compoundsWe believe that the focus on antioxidant potential of DNP4-2 and DDP2-1structures in near future

action toward ABTS free radicals and it also shows a weakDPPH free radical scavenging action On the contrary Ddenneanum polysaccharide exerts a powerful DPPH freeradical scavenging action but its ABTS scavenging effectis not obvious [54] In addition both D huoshanense andD chrysotoxum polysaccharides reveal an insufficient ABTSfree radical scavenging effect However it manifests poten-tial hydroxyl radical scavenging activity Overall the freeradical scavenging activities of polysaccharides on hydroxyland DPPH free radicals remain at a high level but theinhibitory effect on ABTS free radicals is weak The aboveresults compared with other types of polysaccharides fromD denneanum andD nobile are shown in Tables 2 and 3 andothers are shown in Table 4 [41 53] The polysaccharide ofDhuoshanensehas a backbone of (1rarr 4)-linked120572-D-Glcp (1rarr6)-linked 120572-D-Glcp and (1rarr 4)-linked 120573-D-Manp frommannose (Man) glucose (Glc) and a trace of galactose (Gal)Its antioxidant effect in the livers of CCl4-treated mice wasevidenced by a decrease of malondialdehyde (MDA) andincrease of superoxide dismutase (SOD) catalase (CAT) andglutathione peroxidase (GPx) [70]

311 The Antioxidant Activities of Bibenzyl Derivatives Phe-nanthrenes and Stilbenes from D candidum and D loddi-gesii Four new bibenzyl derivatives dendrocandin F den-drocandin G dendrocandin H and dendrocandin I areextracted from D candidum They act as antioxidant agentsto clear up the free radicals Accordingly the IC50 valuesof dendrocandin F and dendrocandin G are 558mM and324mM respectively [49] A series of structurally relatedcompounds from D loddigesii known as loddigesiinol AndashD suppress the production of nitric oxide (NO) with IC

50

values of 26mM for loddigesiinol A 109mM for loddi-gesiinol B and 697mM for loddigesiinol D Further study

Table 3 Assessment of the ABTS hydroxyl and DPPH scavengingabilities of DNP and compounds DNP4-2 DNP2-1 DNP3-1 andDNP1-1 derived from DNP

DNP DNP4-2 DNP2-1 DNP3-1 and DNP1-105mg for DPPHscavenging ()

1mg for DPPHscavenging ()

Type Scavenging () Type Scavenging ()DNP 20 DNP 20ndash30DNP4-2 20ndash30 DNP4-2 30ndash40DNP2-1 5ndash10 DNP2-1 10ndash20DNP3-1 About 5 DNP3-1 lt5DNP1-1 lt5 DNP1-1 About 5

05mg for ABTSscavenging ()


Type Scavenging () Type Scavenging ()DNP 30ndash40 DNP lt60DNP4-2 About 40 DNP4-2 gt60DNP2-1 lt20 DNP2-1 About 40DNP3-1 ge20 DNP3-1 30ndash40DNP1-1 10 DNP1-1 30

05mg for hydroxylscavenging ()


Type Scavenging () Type Scavenging ()DNP 30ndash40 DNP 35ndash40DNP4-2 20ndash30 DNP4-2 30ndash35DNP2-1 10 DNP2-1 10ndash15DNP3-1 5ndash10 DNP3-1 10DNP1-1 0 DNP1-1 5Based on data for DNP DNP4-2 DNP2-1 DNP3-1 and DNP1-1

scavenging ()DPPH scavenging (05mg content) DNP4-2 gt DNP gt DNP2-1

gt DNP3-1 gt DNP1-1DPPH scavenging (1mg content) DNP4-2 gt DNP gt DNP2-1 gt

DNP1-1 gt DNP3-1ABTS scavenging (05mg content) DNP4-2 gt DNP gt DNP3-1

gt DNP2-1 gt DNP1-1ABTS scavenging (1mg content) DNP4-2 gt DNP gt DNP2-1 gt

DNP3-1 gt DNP1-1Hydroyl scavenging (05mg content) DNP gt DNP4-2 gt

DNP2-1 gt DNP3-1 gt DNP1-1Hydroyl scavenging (1mg content) DNP gt DNP4-2 gt DNP2-1

gt DNP3-1 gt DNP1-1Up the table it is shown that DPPH and ABTS free radical scavenging () ofDNP4-2 are better than other compounds however the hydroxyl free radicalscavenging () of DNP is better than other compounds

indicated that phenanthrenes and dihydrophenanthrenesinD loddigesii have significant effects on inhibiting the pro-duction of NO and DPPH free radicals These compoundsare known as (numbered as 1andash7a) phenanthrenes (1a)phenanthrenes (2a) phenanthrenes (3a) phenanthrenes (4a)dihydrophenanthrenes (5a) dihydrophenanthrenes (6a) anddihydrophenanthrenes (7a) Based on the above results thescavenging activity of loddigesiinols toward NO free radicals


Table 4 Comparison of the DPPH hydroxyl and ABTS free radical scavenging abilities of polysaccharides from D huoshanense Dchrysotoxum and D fimbriatum species

Dendrobium species Chemical compounds DPPH concentration (mgmL)05 1 2 3

D huoshanense and D chrysotoxum Polysaccharides (scavenging effects ) 45ndash50 AB 80 90ndash95 mdashD fimbriatum Polysaccharides (scavenging effects ) mdash 10 mdash 40ndash50

Dendrobium species Chemical compounds Hydroxyl concentration (mgmL)05 1 2 3

D huoshanense and D chrysotoxum Polysaccharides (scavenging effects ) 50 60ndash65 80 mdashD fimbriatum Polysaccharides (scavenging effects ) mdash 55ndash60 mdash 70ndash75

Dendrobium species Chemical compounds ABTS concentration (mgmL)05 1 2 3

D huoshanense and D chrysotoxum Polysaccharides (scavenging effects ) AB 10 AB 20 AB 25 mdashD fimbriatum Polysaccharides (scavenging effects ) mdash AB 70 mdash AB 90lowastNotes mdash no tests and about ABThe scavenging hydroxyl free radicals abilities of polysaccharides fromD huoshanense andD chrysotoxum are stronger thanD fimbriatum and the scavengingABTS free radicals abilities of polysaccharides fromD fimbriatum are stronger thanD huoshanense andD chrysotoxum polysaccharides Results showed thatpolysaccharides (scavenging DPPH effects ) fromD huoshanense andD chrysotoxum are higher than hydroxyl and ABTS And polysaccharides (scavengingABTS effects ) from D fimbriatum are higher than DPPH and hydroxyl free radicals

is pronounced The inhibitory actions of phenanthrenes anddihydrophenanthrenes from D loddigesii on the productionof NO and DPPH free radicals are recognised The relevantdata and information are shown in Table 5 [71]

32 Anti-Inflammatory Activity

321 Inhibition of Nitric Oxide (NO) by D nobile and D chry-santhum Constituents It is known that upon lipopolysac-charide (LPS) stimulation macrophages produce a largeamount of inflammatory factors such as tumor necrosis fac-tor120572 (TNF-120572) interleukin-1 beta (IL-1120573) interleukin 6 (IL-6)interferon (IFN) and other cytokines LPS induces endoge-nous nitric oxide (NO) biosynthesis through induction ofinducible nitric oxide synthase (iNOS) in macrophageswhich is involved in inflammatory responses [42] D nobileand D chrysanthum constituents strongly inhibit TNF-120572 IL-1120573 IL-6 and the NO production

322 D nobile Constituents From D nobile two new biben-zyl derivatives namely nobilin D (given number 1) andnobilin E (given number 2) and a new fluorenone namelynobilone (given number 3) together with seven knowncompounds (given numbers 4ndash10) including R

1= R2=

OCH3R3= OH R

4= H (4) R

1= R2= R3= OCH

3R4= H

(5) R1= R2= OH R

3= R4= H (6) R

1= R3= OCH

3R2

= OH R4= H (7) R

1= OCH

3R2= R3= OH R

4= H (8)

R1= R3= OH R

2= R4= H (9) and R

1= R3= OH R

2=

HR4= OCH

3(10) have been identified Compounds 1ndash3

5 and 8ndash10 can inhibit NO production On the other handcompounds 2 and 10 can exhibit a strong to resveratrol whileenhanced cytotoxic potential has been found in compounds4 and 7 Compounds 1ndash10 act as NO inhibitors as evidencedby oxygen radical absorbency capacity (ORAC) assaysThesefindings are focused on all of these compounds except

compound 6 and their inhibitory effects on NO productionin murine macrophages (RAW 2647) activated by LPS andinterferon (IFN-c) are shown in Table 5 [38] Furthermoreit was found that a new phenanthrene together with nineknown phenanthrenes and three known bibenzyls manifestsan inhibitory effect on NO production in RAW 2647 cellsThe structures of all of the compounds (given numbers AndashM) including R

1= R3= OH R

2= R5= OCH

3 R4= H(A)

R1= R4= R5= OH R

2= H R

3= OCH

3(B) R

1= R5=

OH R2= R3= OCH

3 R4= H(C) R

1= R2= OCH

3 R3=

R5= OH R

4= H(D) R

1= H R

2= R3= OH(E) R

1= H

R2= OH R

3= OCH

3(F) R

1= OCH

3 R2= R4= OH R

3

= R5= H(G) R

1= R3= OH R

2= OCH

3(H) R

1= R5=

OH R2= R4= H R

3= OCH

3(I) R1= R3= OCH

3 R2=

R5= OH R

4= H(J) R

1= R2= R4= OH R

3= OCH

3 R5=

H(K) R1= OCH

3 R2= R4= H R

3= R5= OH(L) and

R1= R2= R3= OH R

4= R5= H(M) were elucidated by

analysis of the spectroscopic data including extensive two-dimensional nuclear magnetic resonance spectroscopy (2D-NMR) and mass spectrometry (MS) All of compounds C DI K and L are relatively strong inhibitors of NO productionand their potencies are better than those of compoundsA andEndashH [58] Compounds C D I K and L could inhibit NOsynthesis which might contribute to the suppression of LPS-induced TNF-120572 and IL-1120573 production

323 D chrysanthum Constituents Anti-inflammatorycompounds from ethyl acetate extracts of D chrysanthumspecies were evaluated These structures were elucidated onthe basis of the high-resolution mass spectrometry NMRspectroscopy and X-ray crystal diffraction analysis A novelphenanthrene phenol derivative with a spironolactone ring(dendrochrysanene) namely 2-hydro-770100-trihydroxy-4-40-dimethoxylspiro[(1H)-cyclopenta[a]naphthalene-330-(20H)-phenanthro[21-b]furan]-120-dione was identifiedResults showed anti-inflammatory activity of dendrochry-


Table 5 Inhibition of compounds from D loddigesii and D nobilespecies on NO and DPPH formation

Species Chemical constituent NO DPPH

Dloddigesii

Phenanthrenes (1a) 26 261Phenanthrenes (2a) 64 598Phenanthrenes (3a) 53 12Phenanthrenes (4a) 109 mdashDihydrophenanthrenes (5a) 46 622Dihydrophenanthrenes (6a) 291 mdashDihydrophenanthrenes (7a) 292 mdashLoddigesiinols A 26 mdashLoddigesiinols B 109 mdashLoddigesiinols C mdash 237Loddigesiinols D 697 mdash

Dnobile

Nobilin D (1) 153 mdashNobilin E (2) 192 mdashNobilone F (3) 381 mdashPhenanthrenes and bibenzylsrelated-composition (4ndash10)RO R1 = R2 = OCH3 R3 = OH R4 = H (4) mdash mdashRO R1 = R2 = R3 = OCH3 R4 = H (5) 482 mdashRO R1 = R2 = OH R3 = R4 = H (6) mdash mdashRO R1 = R3 = OCH3 R2 = OH R4 = H (7) mdash mdashRO R1 = OCH3 R2 = R3 = OH R4 = H (8) 368 mdashRO R1 = R3 = OH R2 = R4 = H (9) 329 mdashRO R1 = R3 = OH R2 = H R4 = OCH3 (10) 134 mdash

lowastNotes mdash no tests RO relation compositionInhibitory effects of different compounds from D loddigesii and D nobilespecies on NO production Result shown in Table 5 ranked from high tolow as follows loddigesiinol D gt R1 = R2 = R3 = OCH3 R4 = H (5) gtnobilone F (3) gt R1 = OCH3 R2 = R3 = OH R4 = H (8) gt R1 = R3 = OHR2 = R4 = H (9) gt dihydrophenanthrenes (7a) gt dihydrophenanthrenes(6a) gt nobilin E (2) gt nobilin D (1) gt R1 = R3 = OH R2 = H R4 =OCH3 (10) gt phenanthrenes (4a) = loddigesiinols B gt phenanthrenes (2a) gtphenanthrenes (3a) gt dihydrophenanthrenes (5a) gt phenanthrenes (1a) gtloddigesiinols A and all of the compounds inhibit DPPH prodruction(from high to low) dihydrophenanthrenes (5a) gt phenanthrenes (2a) gtphenanthrenes (1a) gt loddigesiinol C gt phenanthrenes (3a)

sanene on iNOS mRNA induced by LPS in mouse peritonealmacrophages Meanwhile there are several inflammatorycytokines such as TNF-120572 IL-8 and IL-10 which wereinhibited Thus the beneficial effects of dendrochrysanenecompounds as anti-inflammatory agents were identified [72]

33 Sjogrenrsquos Syndrome (SS) Sjogrenrsquos syndrome (SS) is achronic autoimmune disease with disorder of the exocrineglands The symptoms are dry eyes dry mouth dry throatand thirst with blurred vision and so forth The abnormaldistribution of salivary glands in SS leads to an inflam-matory effect and pathological processes triggering lym-phocyte infiltration and apoptosis Lymphocyte infiltrationand apoptotic pathways shown by regulation of Bax Bcl-2and caspase-3 have been reported in submandibular glands(SG) Furthermore in pathological processes were also found

that the subsequent signal of cell expression to mRNA ofproinflammatory cytokines such 30 as tumor necrosis (TNF-a) interleukin (IL-1120573) and IL-6 As well as a high level ofexpression of aquaporin-5 (AQP-5) is identifiedAQP-5 is oneof a water channel protein and plays an important role in 31the salivary secretions [73 74]

Treatment with D officinale polysaccharides (DP) couldsuppress the progression of lymphocyte infiltration and apop-tosis in SS and rectify the chaos of proinflammatory cytokinesincluding TNF-120572 IL-1 beta and IL-6 in SG [71 75] (Figure 1)mRNA expression of TNF-120572 was inhibited The process ofregulation resulted in a series of marked responses such astranslocation of NF-120581B prolonged MAPK cytochrome Crelease and caspase-3 activation which have been identified[55 76] In addition to the findings onDP treatment there arereports on the findings on the extracts ofD candidum andDnobile

A clinical study found that after 1 week of oral adminis-tration of the extract of D candidum salivary secretion wasincreased by approximately 65 The extract promoted theexpression of aquaporin-5 useful for treatment of Sjogrenrsquossyndrome (SS)

Chrysotoxine isolated from D nobile can increase theexpression of AQP-5 in dry eyes one of the symptoms of SSand restore the distribution of AQP-5 in lacrimal glands andcorneal epithelia by inhibiting the release of cytokines suchas IL-1 IL-6 and TNF-120572 In the meantime it can activate themitogen-activated protein kinase (MAPK) signaling path-ways Furthermore it elicits an increase in the production ofmatrix metalloproteinase-9 (MMP-9) Ultimately it leads toan increase of saliva and tear secretion The medical efficacyof the extracts of D officinale D nobile and D candidumspecies has been demonstrated [43] (Figure 1)

34 Neuroprotective Effect (Parkinsonian Syndrome) Fivebioactive derivatives isolated from Dendrobium speciesnamely chrysotoxine (CTX) moscatilin crepidatin nobilinB and chrysotobibenzyl are potential neuroprotective com-pounds with antioxidant activity which can be used inthe treatment of Parkinsonrsquos disease (PD) The IC

50values

of DPPH free radical scavenging activities of chrysotoxine(CTX) moscatilin crepidatin and nobilin B were 208 plusmn 09281 plusmn 71 382 plusmn 35 and 222 plusmn 14 respectively The abovedata show that crepidatin is better than other compounds inDPPH free radical scavenging capacity CTX could selectivelyantagonize MPP+ in dopaminergic pathways in the brainalso 6-hydroxydopamine (6-OHDA) has been inhibited bymitochondrial protection and NF-120581B modulation in SH-SY5Y cells Thus it could explain how it may be beneficialin preventing PD [44 77]

In addition results of CTX compound in Dendro-bium nobile Lindl used in treatment of PD have alsobeen clearly reported We evaluated the pharmacokineticsof oral (100mgkg) and intravenous (25mgkg) adminis-tration of CTX preparation using high performance liq-uid chromatography-tandem mass spectrometric (HPLC-MSMS)method in animal tests [78] Results indicate efficacy


Polysaccharide

HPS-IB23

OAc3 OAc2 OAc2 OAc3 OAc2

Cytokines factorsHematopoietic growth factors

OAc3 120572-D-Gal 120572-D-Gal

[-Manp-(1-[---4)-120573-D---4)-b-D-Glcp-(1rarr4)-b-D-Manp-(1rarr4)-120573-D-Manp-(1rarr4)-120573-D-Manp-(1rarr4)-120573-D-Manp-(1rarr4)-120573-D-Manp-(1rarr4)-120573-D-Manp-(1rarr4-)-b-D-Manp-(1rarr4-]n

TNF-120572uarrGC-SFuarr

GM-CSFuarr

rarr1)-120572-D-Glup(6-1) -120572-D-Glup(6-1) -120572-D-Glup(6-1) -120572-D-Glup(6-1) -120572-D-Glup(6-1)-120572-D-Glup(6-1-120572-D-Glup(6rarr1) -120572-D-Glup(6-1) -120572-D-Glup(4-1) -120572-D-Glup(4-]n

lowastNotes inducementdarr activationuarr

Figure 1 Cytokines activated by polysaccharide and polysaccharide (HPS-IB23) fromD huoshanenseThe effect of twoOAc3 and three Oac2from polysaccharide on GC-SF and GM-CSF upregulation and also the effect of one oAc3 and two 120572-D-Gal from polysaccharide (HPS-IB23)on TNF-120572 upregulation

and safety in treating PD conditions The antioxidant mech-anisms towards 6-OHDA and SH-SY5Y and regulation ofantiapoptosis in cell signaling pathways were described [52]

35 Immunomodulatory Activity Lymphocytes can be clas-sified as T lymphocytes B lymphocytes and macrophagesrespectively They are important to immune cells and playa key role for reactions and responses in the immunesystem Generally there are various types of lymphocyteswhich are activated by very complex signal transductionpathways Among all the most common type is the action oflipopolysaccharides (LPS) in macrophages which are able toproduce many different kinds of proinflammatory cytokinesespecially TNF-120572 which is one of the main proinflammatorycytokines and plays a critical role in mediating signal trans-duction and stimulating the immune defense system [79]The immunopotentiating action from Dendrobium speciesproduced by concanavalin A- (Con A-) stimulated prolifer-ation of splenocytes in mouse Finding the part of which theD officinalis produced a more potent immunopotentiatingaction although it did not provided related to informationof biological activity [57]

Sesquiterpenes from D nobile showed a comitogeniceffect on Con A- and LPS-stimulated mouse splenocytesOther chemical components including polysaccharidesand sesquiterpene glycosides were also confirmed Related

sesquiterpene glycosides with alloaromadendrane emmotinand picrotoxane type aglycones namely dendroside A den-dronobilosides A In vitro biological tests suggest the typesof polysaccharides and sesquiterpene glycosides (given asdendrosides DndashG) significantly promoted cell proliferationand more stimulation of mouse T andor B lymphocytes[45 80] On the other hand compounds fromDmoniliformenamely dendroside A dendroside C and vanilloloside werefound to stimulate the proliferation of B cells and inhibit theproliferation of T cells in vitro [46] (Table 6)

In addition the leaf stem (cell walls) and mucilageisolated of D huoshanense using chemical and enzymaticanalyzed by chromatographic and spectroscopic methodsresults demonstrated the bioactivity from polysaccharidesand itrsquos structure HPS-1B23 The potential effects for maincomposed ofmoremonosaccharides showing Xyl AraManGlc Gal and GalA by HPS-1B23 signify an increasingimmunostimulating activity through upregulating the levelsof several cytokines including TNF-120572 IL-10 IL-6 and IL-1 [47] In addition the stem cell mucilage polysaccharidesof D huoshanense composed of 120573-(1-4)-D-Glcp and 120573-(1-4)-D-Manp linkages with partial acetylated mannosides wereidentified which upregulated the growth factors GM-CSFand G-CSF DHP-4A stimulated RAW 2647 macrophagesto secrete NO TNF-120572 IL-6 and IL-10 by activating p38ERK JNK and NF-120581B The results provide clear scientific


Table 6 The chemical compounds from D nobile and D monili-forme that inhibitedactivated T cells and B cells

Dendrobiumspecies Compoundstructure Lymphocytes

T cell B cell

D nobile

Dendroside D (AD) (AD)Dendroside E (AD) (AD)Dendroside F (AD) (AD)Dendroside G (AD) (AD)

D moniliforme

Dendroside A (IY) (AD)Dendroside C (IY) (AD)Vanilloloside (IY) (AD)Denbinobin (IY) (AD)26-Dimethoxy 1458-phenanthradiquinone (IY) (AD)

lowastNotes activation AD inhibition IYUp the table showed T cell and B cell activated by chemical compounds fromD nobile and inhibit T cell and activated on B cell by chemical compoundsfrom D moniliforme

evidence on regulation of hematopoietic growth factorsand cytokines factors in the immune system by differentpolysaccharides from D huoshanense [81 82] Interestinglythe total polysaccharides of D huoshanense induced theexpression of interleukin-1 receptor antagonist (IL-1ra) inhuman monocytes Which the IL-1ra was regulated by 37a series of signaling pathways like ERKELK p38 MAPKPI3K and NF-120581B [83]

In addition the water-soluble polysaccharides (DTP)derived fromD tosaensewere isolated by usingHPAEC-PADHP-SEC GCndashMS andNMR spectroscopyThey significantlyincreased the number of natural killer (NK) cells NK cyto-toxicitymacrophage phagocytosis and cytokine induction insplenocytes when administered orally to BALBc mice for 3weeks [59]

36 Treatment of Diabetes The compounds isolated fromDendrobium huoshanense (DHP) have been evaluated fortreatment of diabetes in recent years The hypoglycemicand antioxidative activities of three polysaccharides namelyD officinale (DOP) D nobile (DNP) and D chrysotoxum(DCP) have been compared in diabetic mice Result showedthat the hypoglycemic effect of DHP was better than thoseof DNP and DOP In addition the antioxidant effect ofDHP was better than those of DOP and DNP by regulatingthe superoxide dismutase catalase malonaldehyde and l-glutathione levels in the liver and kidney Thus the hypo-glycemic and antioxidant activities of DHPneed to be studiedmore extensively in the future [60]

37 Antitumor Activity

371 The Anticancer Effect of D chrysotoxum and D nobileFluorenone derivatives namely dendroflorin and den-chrysan A isolated from stems of D chrysotoxum speciesshow significant inhibitory effects on the growth of human

hepatomaBEL-7402 cellsThe IC50values of 145-trihydroxy-

7-methoxy-9H-fluoren-9-one denchrysan A 1 and den-droflorin were 149 120583gmL 138 120583gmL and 097 120583gmLrespectively

On the other hand erianin a phenanthrene from Dchrysanthum is recognized as an antitumor agent Reportsshowed that it has potent inhibitory activity in hepatomaBel7402 melanoma A375 and HL-60 cells as evidencedby inhibition of angiogenesis and induction of endothelialcytoskeletal disorganization in vivo and in vitro but did notshow antitumor activity [56 61] Thus further investigationis needed to identify if the antitumor mechanisms of erianinand denbinobin are similar

The antitumor effects of polysaccharides isolated fromstems of D nobile namely DNP-W DNP-OH and DNP-H were studied DNP-W was further fractionated to givesix subfractions including DNP-W1 DNP-W2 DNP-W3DNP-W4 DNP-W5 and DNP-W6 by using anion exchangechromatography The results show that DNP-W DNP-OHand DNP-H DNP-W1 DNP-W2 and DNP-W3 especiallyDNP-W1 and DNP-W3 have a strong antitumor action ininhibiting sarcoma 180 in vivo and HL-60 cells in vitro [48]In addition denbinobin is a major phenanthrene isolatedfrom stems of D nobile The inhibitory mechanisms ofdenbinobin in SNU-484 cells have been observed It signifi-cantly decreased the expressions of matrix metalloproteinase(MMP-2) and (MMP-9) and induced apoptosis throughdownregulation of Bcl-2 and upregulation of Bax in cancercells These findings may be used to provide reference forfurther studies on the pharmacological mechanisms fromdenbinobin and polysaccharides in D nobile [50 51 84]

372 Antilymphoma Activity of Dendrobium formosumLymphoma is a cancer of the immune system The ethanolicextract of Dendrobium formosum showed antilymphomaactivity in vitro as evaluated by the MTT assay It alsosignificantly prolonged survival time in Daltonrsquos lymphomabearing mice [85]

373 Anti-Lung-Cancer Activity of Dendrobium draconisThe bibenzyl compound gigantol has been isolated fromDendrobium draconis It inhibits several cancer cell linesand inhibits filopodia formation of the non-small-cell lungcancer cells The molecular mechanism of gigantol includes(1) downregulating caveolin-1 (Cav-1) (2) activating ATP-dependent tyrosine kinase and (3) regulating cell divisioncycle 42 (Cdc42) [86]

38 Antimicrobial Activity and Antifungal Activity Dendro-bium is an important economic plant however there havebeen certain cultivation issues yet to be resolved particularlyfungal infection [87] Pythium vexans has been reported tocause stem rot crown rot root rot damping-off and patchcanker in Dendrobium plants [88] The diseases could leadto damage to the seedlings of D chrysotoxum D chrysan-thum D thyrsiflorum and D aurantiacum characterizedby water-soaked brown or yellowish lesions with a brownmargin resulting in dieback of the plants within a few days


Table 7 The pharmacological effects of Dendrobium species

Species Chemical compoundsstructures Pharmacological activities ReferencesD nobile Polysaccharides Scavenging effect of hydroxyl ABTS and DPPH [40 41](SR) Nobilin D nobilin E nobilone Inhibitory on NO production [42]

(SR) Phenanthrenes Inhibition of LPS-induced of nitric oxideproduction [38]

(SR) Dendroside A Dendronobilosides A Immunomodulatory activity [43 44]

(SR) Glycosides (dendrosides DndashG) Significant Stimulation of the proliferation ofmouse T andor B lymphocytes [43 44]

(SR) Polysaccharides (DNP-W1 DNP-W2DNP-W3 DNP-W4) Anticancer activity [45]

(SR) 47-Dihydroxy-2-methoxy-910-dihy Anticancer activity [46]Drophenanthrene denbinobin (SNU-484 human gastric cancer cells) [46]

(SR) (SR) (human lung carcinoma) SK-OV-3 [47](SR) (SR) (human ovary adenocarcinoma) [47](SR) (SR) HL-60 (human promyelocytic leukemia) cell lines [47](SR) Bibenzyl Inhibit on furylfuramide [48](SR) (SR) 4-nitroquinoline-1-oxide (4NQO) [48](SR) (SR) N-Methyl-N1015840-nitro-N-nitrosoguanidine [48](SR) (SR) UV irradiation [48]

(SR) (SR) 3-Amino-14-dimethyl-5H-pyrido[43b]indole(Trp-P-1) [48]

(SR) (SR) Benzo[a]pyrene (B[a]P) [48](SR) (SR) Aflatoxin B(1) [48](SR) Nobilin D Anti-inflammatory activity [42](SR) Nobilin E (SR) [42](SR) Nobilone (SR) [42](SR) R1 = R2 = OCH3 R3 = OH R4 = H (SR) [42](SR) R1 = R2 = R3 = OCH3 R4 = H (SR) [42](SR) R1 = R3 = OCH3 R2 = OH R4 = H (SR) [42](SR) R1 = OCH3 R2 = R3 = OH R4 = H (SR) [42](SR) R1 = R3 = OH R2 = R4 = H (SR) [42](SR) R1 = R3 = OH R2 = H R4 = OCH3 (SR) [42]D loddigesii Phenanthrenes Inhibition of nitric oxide (NO) [49](SR) Loddigesiinols AndashD (SR) [49]

(SR) Moscatilin moscatin moscatilindiacetate

Inhibited both AA and collagen-induced plateletaggregations [50 51]

(SR) mdash Inhibition of aggregation of rabbit plateletsinduced by arachidonic acid and collagen [50 51]

D huoshanense Polysaccharides Inducing several cytokines including IFN-cIL-10 IL-6 and IL-1 [52]

(SR) (SR) Immunostimulating activity [52](SR) (SR) Increase of TNF-120572 production [52]

(SR) (SR) Inducing several cytokines includinghematopoietic growth factors GM-CSF and GCSF [52]

D denneanum Polysaccharides Scavenging effect of hydroxyl ABTS and DPPH [53]D fimbriatum Polysaccharides Scavenging effect of hydroxyl ABTS DPPH [54]D candidum Bibenzyl Antioxidant activity [20]D officinalis mdash Immunomodulatory activity [55]D findlayanum mdash Inhibition of Alternaria alternata and other [56]


Table 7 Continued

Species Chemical compoundsstructures Pharmacological activities References

D densiflorum Moscatilin homoeriodictyol scoparonescopoletin gigantol Antiplatelet aggregation activity [50 51]

D nobile Dchrysanthum Erianin Anticancer activity hepatoma Bel7402 melanoma

A375 and HL-60 cells [57]

D chrysanthum Dhuoshanense Dendrochrysanene

TNF-120572 IL-8 IL-10 and iNOS mRNAs wereinduced readily from mouse peritonealmacrophages by LPS

[58]

D devonianum Dthyrsiflorum

Epicoccum sp epicorazine A EpicorazineB Inhibition of S aureus E coli and B subtilis [59 60]

D devonianum Dthyrsiflorum Pyrenophorol derivatives Inhibition of Ecoli Bacillus megaterium and

Microbotryum violaceum [61]lowastNotes mdash no tests SR similar

[89] Interestingly it also resulted in antimicrobial activityfrom endophytic bacteria isolated from Dendrobium speciesScreening of various endophytic fungi from roots and stemsof different Dendrobium species including 53 endophyticfungi from D devonianum 23 endophytic fungi from Dthyrsiflorum by way of morphological andor molecularbiological methods showed that 10 endophytic fungi fromD devonianum and 11 endophytic fungi from D thyrsiflorumexhibited strong antimicrobial activity Phoma Epicoccumand Fusarium isolated from two abovementioned Den-drobium species demonstrated antibacterial and antifungalactivities The pyrenophorol derivatives of Phoma possessedantagonistic activity against E coli Bacillus megateriumand Microbotryum violaceum and Epicoccum sp slightlyinhibited S aureus E coli and B subtilis Fusarium demon-strated inhibitory effect on different pathogens Moreoverepicorazine A and epicorazine B derivatives of Epicoccumnigrum isolated from D thyrsiflorum possessed antibacterialactivity against S aureus and B subtilis and also inhibited thegrowth of Gram-positive and Gram-negative bacteria with apotency stronger than that of ampicillin sodium [90ndash93]

39 Antimalarial and Antiherpetic Activities

391 Antimutagenic Activity Moscatilin obtained from Dnobile is a naturally occurring antimutagenic bibenzyl com-pound This compound can exert a suppressive effect onthe mutagenic activity of furylfuramide 4-nitroquinoline-1-oxide (4NQO) N-methyl-N1015840-nitro-N-nitrosoguanidine UVirradiation 3-amino-14-dimethyl-5H-pyrido[4 3b]indole(Trp-P-1) benzo[a]pyrene (B[a]P) and aflatoxin B(1) [94]

310 Diabetic Retinopathy (DR) Diabetes mellitus (DM) isone of the metabolic diseases It can cause many compli-cations such as kidney failure stroke and foot ulcers Theethanol extract of Dendrobium chrysotoxum (DC) used intreatment of diabetic retinopathy reduced the expressionof a series of growing factors in DC-treated diabetic ratsIt decreased the retinal mRNA expression level of vascu-lar endothelial growth factor (VEGF) vascular endothelialgrowth factor receptor 2 (VEGFR2) serum growth factor

(SVEGF) matrix metalloproteinase (MMP) 29 basic fibrob-last growth factor (bFGF) platelet-derived growth factor(PDGF) AB insulin-like growth factor 1 (IGF-1) interleukin1120573 (IL-1120573) interleukin 6 (IL-6) and phosphorylation ofp65 Moreover a decrease in the expression of intercellularadhesion molecule-1 (ICAM-1) has been reported [95]

311 Antiplatelet Aggregating Activity Studies on the aggre-gation of platelets induced through thrombin arachidonicacid (AA) thrombin collagen and platelet-activating factor(PAF)were conducted by using 4 different aggregation induc-ers Animal tests disclosed that different Dendrobium speciesincluding Dendrobium loddigesii and Dendrobium densiflo-rum possess antiplatelet aggregating activity The resultsindicated some compounds isolated from two Dendrobiumspecies more effectively inhibited AA-induced aggregationthan they inhibited aggregation induced by PAF and collagen[96] In animal tests the antiplatelet aggregation ofD loddige-sii species which those compounds in part from moscatilinmoscatin and diacetate They inhibit platelet aggregationwas induced by AA was completely abolished by fraction 4(50 120583gmL) in rabbit platelets Meanwhile further demon-strated there are strongly inhibited both AA and collagen-induced platelet aggregations about 100120583gmL However inPAF there are no significant effects In addition comparisonof different compounds from D densiflorum species suchas moscatilin homoeriodictyol scoparone scopoletin andgigantol which the antiplatelet aggregation activity of theirwere identified in vitro Especially for scoparone has beenreported to possess potent antiplatelet aggregation whomorethan other compounds Thus it possible interactied bycompounds-compounds for antiplatelet aggregation [26 9798] (Table 7)

4 Conclusion

In this paper the history chemistry and pharmacology ofdifferent Dendrobium species are reviewed Especially forbiological pharmacology (Table 7) The pharmacologicalactivities examined include antioxidant anti-inflammatoryimmunomodulatory antitumor antimicrobialantifungal


antimutagenic activities and antiplatelet aggregation acti-vities The ABTS DPPH and hydroxyl radical scavengingeffects of different polysaccharides such as DNP DNP2-1DNP1-1 DNP3-1 and DNP4-2 have been investigated Lod-digesiinol nobilone dihydrophenanthrenes and phenan-threnes have been evaluated for nitric oxide (NO) scavengingeffect Five types of polysaccharides from D huoshanense Dchrysotoxum and D fimbriatum species were compared Dhuoshanense and D chrysotoxum polysaccharides exhibitedstronger DPPH and hydroxyl scavenging activity while Dfimbriatum polysaccharides have stronger ABTS scavengingactivity Dihydrophenanthrenes and loddigesiinol D wereisolated from D loddigesii and D nobile species Dihy-drophenanthrenes significantly inhibited DPPH productionLoddigesiinol D significantly inhibited NO production

Conflict of Interests

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

Acknowledgments

This study was supported by Seed Funding Programme forBasic Research from The University of Hong Kong Projectno 201311159022 and Seed Funding Programme for BasicResearch from the University of Hong Kong Project no201111159043

References

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[2] D K Singh ldquoMorphological diversity of the orchids ofOrissaSarat Misrardquo in Orchids Science and Commerce PPathak R N Sehgal N ShekharM Sharma and A Sood Edsp 35 BSMPS New Delhi India 2001

[3] S P Vaughan A M Grisoni A M H Kumagai and A AR Kuehnle ldquoCharacterization of Hawaiian isolates of Cymbid-ium mosaic virus (CymMV) co-infecting Dendrobium orchidrdquoArchives of Virology vol 153 no 6 pp 1185ndash1189 2008

[4] M M Hossain ldquoTraditional therapeutic uses of some indige-nous orchids of Bangladeshrdquo Medicinal and Aromatic PlantScience and Biotechnology vol 42 no 1 pp 101ndash106 2009

[5] H P Wood The Dendrobiums Timber Press Portland OreUSA 2006

[6] K M Cameron M W Chase W M Whitten et al ldquoAphylogenetic analysis of the Orchidaceae evidence from rbcLnucleotide sequencesrdquo American Journal of Botany vol 86 no2 pp 208ndash224 1999

[7] R L Dressler The Orchids Natural History and ClassificationHarvard University Press Cambridge Mass USA 1981

[8] M A Clements ldquoMolecular phylogenetic systematics in theDendrobiinae (Orchidaceae) with emphasis on Dendrobiumsection Pedilonumrdquo Telopea vol 10 pp 247ndash298 2003

[9] J Xu J Guan X J Chen J Zhao and S P Li ldquoComparisonof polysaccharides from differentDendrobium using saccharidemappingrdquo Journal of Pharmaceutical and Biomedical Analysisvol 55 no 5 pp 977ndash983 2011

[10] K R Kirtiker and B D Basu Indian Medicinal Plants IVBishen Singh Mohendra Pal Singh Dehradun India 2ndedition 1975

[11] C J Bulpitt ldquoThe uses and misuses of orchids in medicinerdquoQJM vol 98 no 9 pp 625ndash631 2005

[12] C L Withner The Orchid A Scientific Survey Ronald PressCompany New York NY USA 1959

[13] S P Das and S K Bhattacherjee ldquoOrchidsrdquo in HerbaceousPerennials and Shade Loving Foliage Plants S K BhattacherjeeEd Pointer Publishers Jaipur India 2006

[14] J-M Kong N-K Goh L-S Chia and T-F Chia ldquoRecentadvances in traditional plant drugs and orchidsrdquo Acta Pharma-cologica Sinica vol 24 no 1 pp 7ndash21 2003

[15] M Li K Y-B Zhang P P-H But and P-C Shaw ldquoForensicallyinformative nucleotide sequencing (FINS) for the authentica-tion of Chinese medicinal materialsrdquo Chinese Medicine vol 6article 42 2011

[16] T B Ng J Liu J H Wong et al ldquoReview of research onDendrobium a prized folk medicinerdquo Applied Microbiology andBiotechnology vol 93 no 5 pp 1795ndash1803 2012

[17] C A Williams ldquoThe leaf flavonoids of the OrchidaceaerdquoPhytochemistry vol 18 no 5 pp 803ndash813 1979

[18] H J Zhang J J Zhou and X S Li ldquoStudy advance of gastrodiaelata b1rdquo Amino Acids and Biotic Resources vol 25 no 1 pp17ndash20 2003

[19] P L Majumder S Guha and S Sen ldquoBibenzyl derivatives fromthe orchid Dendrobium amoenumrdquo Phytochemistry vol 52 no7 pp 1365ndash1369 1999

[20] Y Li C-L Wang Y-J Wang et al ldquoThree new bibenzylderivatives from Dendrobium candidumrdquo Chemical and Phar-maceutical Bulletin vol 57 no 2 pp 218ndash219 2009

[21] Y Li C L Wang S X Guo J S Yang and P G Xiao ldquoTwonew compounds from Dendrob-ium candidumrdquo Chemical andPharmaceutical Bulletin vol 56 pp 1477ndash1499 2008

[22] Y Chen J Li L Wang and Y Liu ldquoAromatic compounds fromDendrobium aphyllumrdquo Biochemical Systematics and Ecologyvol 36 no 5-6 pp 458ndash460 2008

[23] Y Chen Y Liu J Jiang Y Zhang and B Yin ldquoDendrononea new phenanthrenequinone from Dendrobium cariniferumrdquoFood Chemistry vol 111 no 1 pp 11ndash12 2008

[24] Y Chen Y Li C Qing Y Zhang L Wang and Y Liuldquo145-Trihydroxy-7-methoxy-9H-fluoren-9-one a new cyto-toxic compound from Dendrobium chrysotoxumrdquo Food Chem-istry vol 108 no 3 pp 973ndash976 2008

[25] H Yang G-X Chou Z-TWang Y-W Guo Z-B Hua and L-S Xu ldquoTwo new compounds from Dendrobium chrysotoxumrdquoHelvetica Chimica Acta vol 87 no 2 pp 394ndash399 2004

[26] C Fan W Wang Y Wang G Qin and W Zhao ldquoChemicalconstituents from Dendrobium densiflorumrdquo Phytochemistryvol 57 no 8 pp 1255ndash1258 2001

[27] J-T Li B-L Yin Y Liu L-Q Wang and Y-G Chen ldquoMono-aromatic constituents of Dendrobium longicornurdquo Chemistry ofNatural Compounds vol 45 no 2 pp 234ndash236 2009

[28] X Zhang H-W Liu H Gao et al ldquoNine new sesquiterpenesfrom Dendrobium nobilerdquo Helvetica Chimica Acta vol 90 no12 pp 2386ndash2394 2007

[29] Q-F Liu W-L Chen J Tang and W-M Zhao ldquoNovelbis(bibenzyl) and (propylphenyl)bibenzyl derivatives fromDendrobium nobilerdquo Helvetica Chimica Acta vol 90 no 9 pp1745ndash1750 2007


[30] G-N Zhang L-Y Zhong S W A Bligh et al ldquoBi-bicyclicand bi-tricyclic compounds from Dendrobium thyrsiflorumrdquoPhytochemistry vol 66 no 10 pp 1113ndash1120 2005

[31] Y Liu J-H Jiang B-L Yin and Y-G Chen ldquoChemicalconstituents of Dendrobium cariniferumrdquo Chemistry of NaturalCompounds vol 45 no 2 pp 237ndash238 2009

[32] S-F Lo V Mulabagal C-L Chen C-L Kuo and H-S TsayldquoBioguided fractionation and isolation of free radical scaveng-ing components from in vitro propagated chinese medicinalplants Dendrobium tosaense Makino and Dendrobium monili-forme SWrdquo Journal of Agricultural and Food Chemistry vol 52no 23 pp 6916ndash6919 2004

[33] P LMajumder and R C Sen ldquoMoscatilin a bibenzyl derivativefrom the orchid Dendrobium moscatumrdquo Phytochemistry vol26 no 7 pp 2121ndash2124 1987

[34] P L Majumder and S Chatterjee ldquoCrepidatin a bibenzylderivative from the orchid Dendrobium crepidatumrdquo Phyto-chemistry vol 28 no 7 pp 1986ndash1988 1989

[35] P L Majumder and S Pal (Nee Ray) ldquoRotundatin a new910-didydrophenanthrene derivative from Dendrobium rotun-datumrdquo Phytochemistry vol 31 no 9 pp 3225ndash3228 1992

[36] C Honda and M Yamaki ldquoPhenanthrenes from Dendrobiumplicatilerdquo Phytochemistry vol 53 no 8 pp 987ndash990 2000

[37] K Krohn U Loock K Paavilainen B M Hausen H WSchmalle and H Kiesele ldquoSynthesis and electrochemistryof annoquinone-A cypripedin methyl ether denbinobin andrelated 14-phenanthrenequinonesrdquo Arkivoc vol 2001 no 1 pp88ndash130 2001

[38] X Zhang J-K Xu JWang et al ldquoBioactive bibenzyl derivativesand fluorenones from Dendrobium nobilerdquo Journal of NaturalProducts vol 70 no 1 pp 24ndash28 2007

[39] Y Li C-L Wang S-X Guo J-S Yang and P-G Xiao ldquoTwonew compounds from Dendrobium candidumrdquo Chemical andPharmaceutical Bulletin vol 56 no 10 pp 1477ndash1479 2008

[40] A X Luo X J He S D Zhou Y J Fan T He and Z ChunldquoIn vitro antioxidant activities of a water-soluble polysaccharidederived from Dendrobium nobile Lindl extractsrdquo InternationalJournal of Biological Macromolecules vol 45 no 4 pp 359ndash3632009

[41] A Luo and Y Fan ldquoIn vitro antioxidant of a water-solublepolysaccharide from Dendrobium fimhriatum Hookvarocu-latumHookrdquo International Journal of Molecular Sciences vol 12no 6 pp 4068ndash4079 2011

[42] R M Chen T G Chen T L Chen et al ldquoAnti-inflammatoryand antioxidative effects of propofol on lipopolysaccharide-activated macrophagesrdquo Annals of the New York Academy ofSciences vol 1042 pp 262ndash271 2005

[43] L Xiao T B Ng Y-B Feng et al ldquoDendrobium candidumextract increases the expression of aquaporin-5 in labial glandsfrom patients with Sjogrenrsquos syndromerdquo Phytomedicine vol 18no 2-3 pp 194ndash198 2011

[44] J-X Song P-C Shaw C-W Sze et al ldquoChrysotoxine a novelbibenzyl compound inhibits 6-hydroxydopamine inducedapoptosis in SH-SY5Y cells via mitochondria protection andNF-kB modulationrdquo Neurochemistry International vol 57 no6 pp 676ndash689 2010

[45] QYeGQin andWZhao ldquoImmunomodulatory sesquiterpeneglycosides fromDendrobiumnobilerdquoPhytochemistry vol 61 no8 pp 885ndash890 2002

[46] C Zhao Q Liu F Halaweish B Shao Y Ye and WZhao ldquoCopacamphane picrotoxane and alloaromadendrane

sesquiterpene glycosides and phenolic glycosides fromDendro-bium moniliformerdquo Journal of Natural Products vol 66 no 8pp 1140ndash1143 2003

[47] X Q Zha J P Luo S Z Luo and S T Jiang ldquoStructureidentification of a new immunostimulating polysaccharidefrom the stems of Dendrobium huoshanenserdquo CarbohydratePolymers vol 69 no 1 pp 86ndash93 2007

[48] J-HWang J-P Luo X-Q Zha and B-J Feng ldquoComparison ofantitumor activities of different polysaccharide fractions fromthe stems of Dendrobium nobile Lindlrdquo Carbohydrate Polymersvol 79 no 1 pp 114ndash118 2010

[49] Y Li C-L Wang Y-J Wang et al ldquoFour new bibenzylderivatives from Dendrobium candidumrdquo Chemical and Phar-maceutical Bulletin vol 57 no 9 pp 997ndash999 2009

[50] J I Song Y J Kang H Y Yong Y C Kim and A MoonldquoDenbinobin a phenanthrene fromDendrobiumnobile inhibitsinvasion and induces apoptosis in SNU-484 human gastriccancer cellsrdquo Oncology Reports vol 27 no 3 pp 813ndash818 2012

[51] J I Song Y J Kang H-Y Yong Y C Kim and A MoonldquoDenbinobin a phenanthrene fromDendrobiumnobile inhibitsinvasion and induces apoptosis in SNU-484 human gastriccancer cellsrdquo Oncology Reports vol 27 no 3 pp 813ndash818 2012

[52] J-X Song S C-W Sze T-B Ng et al ldquoAnti-Parkinsoniandrug discovery from herbal medicines what have we got fromneurotoxicmodelsrdquo Journal of Ethnopharmacology vol 139 no3 pp 698ndash711 2012

[53] A Luo Z Ge Y Fan Z Chun and X Jin He ldquoIn vitro and invivo antioxidant activity of a water-soluble polysaccharide fromDendrobium denneanumrdquo Molecules vol 16 no 2 pp 1579ndash1592 2011

[54] Y Fan X He S Zhou A Luo T He and Z Chun ldquoCompo-sition analysis and antioxidant activity of polysaccharide fromDendrobium denneanumrdquo International Journal of BiologicalMacromolecules vol 45 no 2 pp 169ndash173 2009

[55] X Lin P-C Shaw S C-W Sze Y Tong and Y B Zhang ldquoDen-drobium officinale polysaccharides ameliorate the abnormalityof aquaporin 5 pro-inflammatory cytokines and inhibit apopto-sis in the experimental Sjogrenrsquos syndrome micerdquo InternationalImmunopharmacology vol 11 no 12 pp 2025ndash2032 2011

[56] T-H Lin S-J Chang C-C Chen J-P Wang and L-T TsaoldquoTwo phenanthraquinones from Dendrobium moniliformerdquoJournal of Natural Products vol 64 no 8 pp 1084ndash1086 2001

[57] D T W Lau M Poon H Leung and K Ko ldquoImmunopoten-tiating activity of Dendrobium species in mouse splenocytesrdquoChinese Medicine vol 2 no 3 pp 103ndash108 2011

[58] J S Hwang S A Lee S S Hong et al ldquoPhenanthrenes fromDendrobium nobile and their inhibition of the LPS-inducedproduction of nitric oxide in macrophage RAW 2647 cellsrdquoBioorganic and Medicinal Chemistry Letters vol 20 no 12 pp3785ndash3787 2010

[59] L C Yang T J Lu C CHsieh andWC Lin ldquoCharacterizationand immunomodulatory activity of polysaccharides derivedfromDendrobium tosaenserdquoCarbohydrate Polymers vol 111 pp856ndash863 2014

[60] L-H Pan X-F Li M-N Wang et al ldquoComparison of hypo-glycemic and antioxidative effects of polysaccharides from fourdifferentDendrobium speciesrdquo International Journal of BiologicalMacromolecules vol 64 pp 420ndash427 2014



[62] S Phetsirikoon S Ketsa andW G van Doorn ldquoChilling injuryinDendrobium inflorescences is alleviated by 1-MCP treatmentrdquoPostharvest Biology and Technology vol 67 pp 144ndash153 2012

[63] B Li J Wei X Wei et al ldquoEffect of sound wave stresson antioxidant enzyme activities and lipid peroxidation ofDendrobium candidumrdquo Colloids and Surfaces B Biointerfacesvol 63 no 2 pp 269ndash275 2008

[64] X Tian and Y Lei ldquoNitric oxide treatment alleviates droughtstress in wheat seedlingsrdquo Biologia Plantarum vol 50 no 4 pp775ndash778 2006

[65] H Fan T Li L Guan et al ldquoEffects of exogenous nitricoxide on antioxidation and DNA methylation of Dendrobiumhuoshanense grown under drought stressrdquo Plant Cell Tissue andOrgan Culture vol 109 no 2 pp 307ndash314 2012

[66] S F Lo S M Nalawade V Mulabagal et al ldquoIn vitro prop-agation by asymbiotic seed germination and 11-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging activity studies oftissue culture raised plants of three medicinally importantspecies ofDendrobiumrdquo Biological and Pharmaceutical Bulletinvol 27 no 5 pp 731ndash735 2004


[68] J-H Wang X-Q Zha J-P Luo and X-F Yang ldquoAn acetylatedgalactomannoglucan from the stems of Dendrobium nobileLindlrdquo Carbohydrate Research vol 345 no 8 pp 1023ndash10272010

[69] W-G Zhang R Zhao J Ren et al ldquoSynthesis and anti-proliferative in-vitro activity of two natural dihydrostilbenesand their analoguesrdquo Archiv der Pharmazie vol 340 no 5 pp244ndash250 2007

[70] C C Tian X Q Zha L H Pan and J P Luo ldquoStructuralcharacterization and antioxidant activity of a low-molecularpolysaccharide from Dendrobium huoshanenserdquo Fitoterapiavol 91 pp 247ndash255 2013

[71] M Ito K Matsuzaki J Wang et al ldquoNew phenanthrenes andstilbenes from Dendrobium loddigesiirdquo Chemical and Pharma-ceutical Bulletin vol 58 no 5 pp 628ndash633 2010

[72] L Yang L H Qin S W A Bligh et al ldquoA new phenanthrenewith a spirolactone fromDendrobium chrysanthum and its anti-inflammatory activitiesrdquo Bioorganic and Medicinal Chemistryvol 14 no 10 pp 3496ndash3501 2006

[73] R I Fox ldquoSjogrenrsquos syndromerdquo The Lancet vol 366 no 9482pp 321ndash331 2005

[74] Y P Ding L SWu and LW Yu ldquoOptimized harvesting periodfor Dendrobium candidumrdquo China journal Chinese MateriaMedica vol 23 pp 458ndash460 1998

[75] N Roescher P P Tak and G G Illei ldquoCytokines inSjogrenrsquos syndrome potential therapeutic targetsrdquo Annals of theRheumatic Diseases vol 69 no 6 pp 945ndash948 2010

[76] L Xiang C W Stephen Sze T B Ng et al ldquoPolysaccharides ofDendrobium officinale inhibit TNF-120572-induced apoptosis in A-253 cell linerdquo Inflammation Research vol 62 no 3 pp 313ndash3242013

[77] J-X Song P-C Shaw N-S Wong et al ldquoChrysotoxine anovel bibenzyl compound selectively antagonizes MPP+ butnot rotenone neurotoxicity in dopaminergic SH-SY5Y cellsrdquoNeuroscience Letters vol 521 no 1 pp 76ndash81 2012

[78] J Fan L Guan Z Kou F Feng Y B Zhang and WLiu ldquoDetermination of chrysotoxine in rat plasma by liquidchromatography-tandemmass spectrometry and its applicationto a rat pharmacokinetic studyrdquo Journal of Chromatography Bvol 967 pp 57ndash62 2014

[79] M Liu J Li F Kong J Lin and Y Gao ldquoInduction of immuno-modulating cytokines by a new polysaccharide-peptide com-plex from culture mycelia of Lentinus edodesrdquo Immunopharma-cology vol 40 no 3 pp 187ndash198 1998

[80] W Zhao Q Ye X Tan et al ldquoThree new sesquiterpeneglycosides from Dendrobium nobile with immunomodulatoryactivityrdquo Journal of Natural Products vol 64 no 9 pp 1196ndash1200 2001

[81] Y S-YHsieh C Chien S K-S Liao et al ldquoStructure and bioac-tivity of the polysaccharides in medicinal plant Dendrobiumhuoshanenserdquo Bioorganic and Medicinal Chemistry vol 16 no11 pp 6054ndash6068 2008

[82] F Li S H Cui X Q Zha et al ldquoStructure and bioactivityof a polysaccharide extracted from protocorm-like bodies ofDendrobium huoshanenserdquo International Journal of BiologicalMacromolecules vol 72 pp 664ndash672 2015

[83] J Lin Y-J Chang W-B Yang A L Yu and C-H Wong ldquoThemultifaceted effects of polysaccharides isolated from Dendro-bium huoshanense on immune functions with the induction ofinterleukin-1 receptor antagonist (IL-1ra) in monocytesrdquo PLoSONE vol 9 no 4 Article ID e94040 2014

[84] H L You J D ParkN I Baek S I Kim andB Z Ahn ldquoIn vitroand in vivo antitumoral phenanthrenes from the aerial parts ofDendrobium nobilerdquo Planta Medica vol 61 no 2 pp 178ndash1801995

[85] R Prasad and B Koch ldquoAntitumor activity of ethanolic extractof Dendrobium formosum in T-cell lymphoma an in vitro andin vivo studyrdquo BioMed Research International vol 2014 ArticleID 753451 11 pages 2014

[86] S Charoenrungruang P Chanvorachote B Sritularak andV Pongrakhananon ldquoGigantol a bibenzyl from Dendrobiumdraconis inhibits the migratory behavior of non-small cell lungcancer cellsrdquo Journal of Natural Products vol 77 no 6 pp 1359ndash1366 2014

[87] P Benjaphorn T Lalita N Ratchaya and P Cholakan ldquoEfficacyof crude extract of antifungal compounds produced from Bacil-lus subtilis on prevention of anthracnose disease inDendrobiumorchidrdquo EnvironmentAsia vol 5 no 1 pp 32ndash38 2012

[88] Y Tao F Zeng H Ho et al ldquoPythium vexans causing stemrot of Dendrobium in Yunnan Province Chinardquo Journal ofPhytopathology vol 159 no 4 pp 255ndash259 2011

[89] M E Barrow Lucero Jr I Reyes-Vera and K M Havstad ldquoDosymbiotic microbes have a role in plant evolution performanceand response to stressrdquo Communicative amp Integrative Biologyvol 1 pp 1ndash5 2008

[90] M A Baute G Deffieux R Baute and A Neveu ldquoNewantibiotics from the fungus Epicoccum nigrum I Fermentationisolation and antibacterial propertiesrdquo The Journal of Antibi-otics vol 31 no 11 pp 1099ndash1101 1978

[91] Y Zhang S Liu Y Che and X Liu ldquoEpicoccins A-D epipoly-thiodioxopiperazines from a Cordyceps-colonizing isolate ofEpicoccum nigrumrdquo Journal of Natural Products vol 70 no 9pp 1522ndash1525 2007

[92] W Zhang K Krohn H Egold S Draeger and B SchulzldquoDiversity of antimicrobial pyrenophorol derivatives from anendophytic fungus Phoma sprdquo European Journal of OrganicChemistry no 25 pp 4320ndash4328 2008


[93] N Sattayasai R Sudmoon S Nuchadomrong et al ldquoDendro-bium findleyanum agglutinin production localization anti-fungal activity and gene characterizationrdquo Plant Cell Reportsvol 28 no 8 pp 1243ndash1252 2009

[94] M Miyazawa H Shimamura S-I Nakamura W SugiuraH Kosaka and H Kameoka ldquoMoscatilin from Dendrobiumnobile a naturally occurring bibenzyl compound with potentialantimutagenic activityrdquo Journal of Agricultural and Food Chem-istry vol 47 no 5 pp 2163ndash2167 1999

[95] C Y Gong Z Y Yu B Lu et al ldquoEthanol extract ofDendrobiumchrysotoxum Lindl ameliorates diabetic retinopathy and itsmechanismrdquoVascular Pharmacology vol 62 no 3 pp 134ndash1422014

[96] C-C Chen Y-L Huang and C-M Teng ldquoAntiplatelet aggre-gation principles from Ephemerantha lonchophyllardquo PlantaMedica vol 66 no 4 pp 372ndash374 2000

[97] Y Okada N Miyauchi K Suzuki et al ldquoSearch for naturallyoccurring substances to prevent the complications of diabetesII Inhibitory effect of coumarin and flavonoid derivatives onbovine lens aldose reductase and rabbit platelet aggregationrdquoChemical and Pharmaceutical Bulletin vol 43 no 8 pp 1385ndash1387 1995

[98] J-M Hu J-J Chen H Yu Y-X Zhao and J Zhou ldquoTwonovel bibenzyls from Dendrobium trigonopusrdquo Journal of AsianNatural Products Research vol 10 no 7-8 pp 653ndash657 2008

Submit your manuscripts athttpwwwhindawicom

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Hindawi Publishing Corporationhttpwwwhindawicom Volume 2014


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Volume 2014Hindawi Publishing Corporationhttpwwwhindawicom


2 The Chemical Compounds ofDendrobium Species

The stem of Dendrobium species has been used in traditionalChinesemedicine as a tonic and antipyretic since ancient daysfor treating human disorders However misidentificationand adulteration led to a loss of therapeutic potency andpotential intoxication For decades fast developingmoleculartechniques using DNA fingerprinting DNA sequencing andDNA microarray have been applied extensively to authen-ticate Chinese medicinal materials including various Den-drobium species [15] namely D aphyllum D candidum Dchrysanthum D densiflorum D huoshanense D gratiosissi-mumD longicornuD nobileD secundumD chrysotoxumD crystallinum D fimbriatum and others [16] In the earlyyears Williams and Harborne conducted a major surveyof leaf flavonoids at the Plant Science Laboratories of theUniversity of Reading in UK They conducted research on142 species belonging to 75 genera and found that the mostcommon constituents were flavone C-glycoside and flavonols[17] Since then about 100 compounds from 42 Dendrobiumspecies including 32 alkaloids 6 coumarins 15 bibenzyls 4fluorenones 22 phenanthrenes and 7 sesquiterpenoids con-stituents have been discussed and reviewed [18ndash31] (Table 1)To date various Dendrobium species are known to producea variety of secondary metabolites The biological activitiesand pharmacological actions of all of these compounds wereinvestigated in detail [32ndash39]

3 The Pharmacological Effects ofDendrobium Species

31 Antioxidant Activities Oxidative stress is induced byfree radicals that participate in a variety of chemical reac-tions with biomolecules leading to a pathological conditionReactive oxygen species (ROS) is one of the major freeradicals It mainly comprises superoxide (O

2

minus) and nitricoxide (NO) radicals including (1) catalase (CAT) (2) perox-idase (POD) (3) ascorbate peroxidase (APX) (4) 221015840-azino-bis(3-ethylbenzothiazoline-6-sulphonic acid) or ABTS (5)hydroxyl and (6) 11-diphenyl-2-picrylhydrazyl (DPPH) rad-icals During these processes it was found that the content ofmalondialdehyde (MDA) was increased

However cells possess two distinctive antioxidant defensesystems to counteract the damage including enzymatic anti-oxidants and nonenzymatic antioxidants Enzymatic antiox-idants comprise catalase superoxide dismutase (SOD) gluta-thione peroxidase (GPx) and others associated with en-zymesmolecules Nonenzymatic antioxidants include ascor-bic acid (vitamin C) 120572-tocopherol (vitamin E) and 120573-carotene which play a key role in removing reactive oxygenspecies

Oxidative stresses have been classified as exogenousfactors and endogenous factors Factors related to environ-mental stress includewatersoil drought stress chilling injurystress and soundwave stressTherewere studies on the effectsof cold storage on cut Dendrobium inflorescences showingthat chilling injury symptoms for floral buds and open flowers

ofDendrobium could lead to oxidative stress stemming fromthe production of reactive oxygen species In this process thedecrease of cellular functions by peroxidation of membranelipids when lipoxygenase enzymes are degraded in cellsHowever this physiological process in floral buds and openflowers is part of antioxidant defense systems which candecrease the content of oxygen free radicals and other oxygencompounds It indicates the protective cellular functions andantioxidant capacity This is an adaptive nature to ensuresome plants survive in the freezing winter [62]

In addition soundwave stress is one of the environmentalstresses similar to the low temperature stress Studies ofthe effects of sound wave stress on D candidum yieldeddata indicated it as a lipid peroxidation parameter whichcan regulate the levels of MDA Firstly the MDA content indifferent organs is increased and then declines afterwardswhich will then be followed by an increase again That givesa net increase of the level of MDA It was noted that theMDA level appears to be the lowest when the activities ofantioxidant enzymes are the highest However the levelsof MDA are yet to be fully understood We believe theantioxidant enzymes could protect plant cells from oxidativedamage in sound wave stress [63] However the correlationbetween themechanisms of antioxidant action and the soundwave stress and chilling injury stress has yet to be identified

Water deficit caused by soil drought is one of the mostfrequent environmental stresses The effects of exogenousdrought menace prompting further increases in the activityof ROS and decrease in themalondialdehyde (MDA) contentto prevent the breakage of DNA and protein degradationfrom doing damage to plant life [64] It is well knownthat nitric oxide (NO) is a ubiquitous signal moleculeinvolved in many life processes of plants seed germinationhypocotyl elongation leaf expansion root growth lateralroots initiation and apoptosis and so forth It is also involvedin multiple plant responses to environmental stress Datademonstrated that at lower concentrations of exogenous NOwith 50mmol Lminus1 SNP the activation of POD SOD and CATwas significantly increased and the MDA content decreasedwith 50Ml SNPNO could protect D huoshanense against theoxidative insult caused by a drought stress meanwhile a highlevel of RWCcan bemaintained Furthermore it suggests thatthe molecular messenger NO can trigger epigenetic variationand increase the demethylation ratio ofmethylated sites forDhuoshanense by using DNA analysis These results may implythat the expression of some genes is involved in the responseto drought stress triggered by NO [65]

Numerous Dendrobium species such as D nobile D den-neanum D huoshanense D chrysotoxum D moniliforme Dtosaense D linawianum D candidum D loddigesii and Dfimbriatum have polysaccharides as the active compoundsPolysaccharides play important roles in many biologicalprocesses and are used to treat various diseases [66 67]Polysaccharides isolated from D nobile D huoshanense Dchrysotoxum andD fimbriatum species manifest antioxidantand free radical scavenging activities D nobile polysac-charide displayed the highest scavenging activity towardhydroxyl ABTS and DPPH free radicals [40 68 69] How-everD fimbriatum polysaccharide has significant scavenging


Table1Th

ecom

poun

dsof

vario

usDendrobium

species

Species

Con

stituent

Chem

icalform

ula

Structures

ofcompo

und

Reference

Da

moenu

mBibenzylsd

erivatives

Amoenylin

R 1=R 3

=MeR 2

=OHR

4=HR

5=OMe

1

23

456

AB

120572

120572998400

1998400

2998400

3998400

4998400

5998400

6998400

OR 1

R 2

OR 3

R 4

R 5[19

]

Isoamoenylin

R 1=R 3

=MeR 2

=OMeR 4

=OHR

5=H

Moscatilin

(analogues)

mdash341015840-D

ihydroxy-5-m

etho

xybibenzyl

mdashmdash

R 1=R 2

=R 4

=HR

3=MeR 5

=OH

mdashR 1

=R 3

=MeR 2

=OHR

4=HR

5=OMe

mdashR 1

=R 3

=MeR 2

=OAc

R4=HR

5=OMe

mdashR 1

=R 3

=MeR 2

=OMeR 4

=OAc

R5=H

mdashR 1

=Ac

R2=R 4

=HR

3=MeR 5

=OAc

mdashR 1

=R 3

=MeR 2

=R 5

=OHR

4=OMe

mdashR 1

=R 3

=MeR 2

=R 4

=OMeR 5

=OH

mdashR 1

=R 3

=MeR 2

=R 5

=OMeR 4

=OAc

mdashR 1

=R 2

=R 5

=HR

3=MeR 4

=OH

mdashR 1

=Ac

R2=R 5

=HR

3=MeR 4

=OAc

mdashR 1

=R 2

=R 3

=R 4

=HR

5=OH

Dc

andidu

mBibenzylsd

erivatives

DendrocandinC

((S)-344-tr


etho

xybibenzyl)

DendrocandinD

((S)-344-tr

ihydroxy-5-m

etho


DendrocandinE

(3344-te

trahydroxy-5-m

etho

xybibenzyl)

R 1=R 2

=R 5

=OHR

3=R 6

=OCH

3R 4

=H

R 1=R 2

=R 5

=OHR

3=OCH

3R 6

=OCH

2CH

3R 4

=H

R 1=R 2

=R 4

=R 5

=OHR

3=OCH

3R 6

=H

1

23

4

56

120572

120572998400

1998400

2998400

3998400

4998400

5998400

6998400

R 1

R 2

R 3

R 4

R 5

R 6

[20]

Amotin

(type

1sesquiterpenoids)

mdash

HO

OH

O

O

OO

Me

HH

[19]


Table1Con

tinued

Species

Con

stituent

Chem

icalform

ula

Structures

ofcompo

und

Reference

Amoenin(ty


mdash

HO HO

OH

O Me

H

OO

[19]

Flaccidin(910

-dihydroph

enanthropyran)

mdash

O

HO

OM

e

OH

[19]

Bibenzylsd

erivatives

44-Dihydroxy-35-dim

etho

xybibenzyl


xybibenzyl

3-O-M

ethylgigantol

Dendrop

heno

lGigantol

New

compo

unds

DendrocandinA


imetho

xybibenzyl)

R 2=R 5

=OHR

1=R 3

=OCH

3R 4

=R 6

=OH

R 1=R 2

=OHR

3=R 5

=OCH

3R 4

=R 6

=OH

R 1=OHR

3=R 4

=R 5

=OCH

3R 2

=R 6

=H

R 2=R 4

=R 5

=OHR

1=R 3

=OCH

3R 6

=H

R 1=R 5

=OHR

3=R 4

=OCH

3R 2

=R 6

=H

R 1=R 2

=OHR

3=R 5

=R 6

=OCH

3R 4

=H

1

23

4

56

120572

120572998400

1998400

2998400

3998400

4998400

5998400

6998400

R 1

R 2

R 3

R 4

R 5

R 6

[21]

DendrocandinB


xyph

enyl)-2-

hydroxym

ethyl-8

-metho

xy-23-

dihydrob


etho

xyl

benzene)

mdashOO

12

345

6

120572120572998400

1998400

2998400

3998400 4998400

5998400

6998400

1998400998400

2998400998400

3998400998400 4998400998400

5998400998400

6998400998400

7998400998400

8998400998400

9998400998400

H3CO

OCH

3

OCH

3

OCH

3

OH

OH

[21]


Table1Con

tinued

Species

Con

stituent

Chem

icalform

ula

Structures

ofcompo

und

Reference

Da

phyllum

Aromaticcompo

unds

Flavanthrin

mdash

OCH

3

OCH

3

OH

OH

HO

HO

[22]

Coelonin

Iusia

nthridin

R 1=OHR

2=OMe

R 1=OMeR 2

=OH

HO

R 1

R 2

[22]

Moscatin

mdashO

H

OH

OM

e

[22]

Gigantol

Batatasin

III

R 1=R 3

=OMeR 2

=OH

R 1=OHR

2=HR

3=OMe

HO

R 1

R 2

R 3

[22]


Table1Con

tinued

Species

Con

stituent

Chem

icalform

ula

Structures

ofcompo

und

Reference

Dibutylph

thalate

Diisob

utylph

thalate

R=CH

2CH

2CH

2CH

3R=CH

2CH(C

H3)

2

CCO

R

OR

O O

[22]


icmethyleste

rmdash

COO

Me

OH

[22]

Dc

ariniferum

Phenanthrenequ

inon

e

Dendron


xy-910

-dihydro-14-

phenanthrenequ

inon

e)mdash

O

MeO

OH

2

34

110

a8a

87

65

4b4a

109

O

[23]

Dc

hrysotoxum

Aromaticorganicc

ompo

unds

(Fluorenon

es)

Dendrofl

orin

DenchrysanA

R 1=HR

2=OH

R 1=OHR

2=H

O

OCH

3

OH

OH

R 1R 2

[24]

145-tr

ihydroxy-7-m

etho

xy-9H-fluo

ren-9-on

emdash

OCH

3

OH

OH 4

56 7

89

123

8a9a4a

4b

OH

O

[24]


Table1Con

tinued

Species

Con

stituent

Chem

icalform

ula

Structures

ofcompo

und

Reference

(Fluorenol)

(9R)-4metho

xy-9H-fluo

rene-259-tr

iol

R=H

OR

OR

RO

OM

e

[25]

Phenanthrene

27-dihydroxy-8m

etho

xyph


5(5H

)-on

emdash

O

O

OH

OH

OM

e

[25]

Dd

ensifl

orum

Bibenzyl

Densifl

orolA

mdash

O

MeO

O

OH

1

2

33

a4

5

6

77

a

1998400

2998400

1998400998400

2998400998400

3998400998400

49984009984005998400998400

6998400998400

7998400998400

[26]

Phenanthrenedion

e

Densifl

orolB

R=H

HO

1

2

3

4a 10

a8

a

4b

45

6

910

7

8

OM

e

O

O

R

[26]


Table1Con

tinued

Species

Con

stituent

Chem

icalform

ula

Structures

ofcompo

und

Reference

Dendrofl

orin

R=OH

OH

OH

OR1

234

a

9a

8a

4b

45

6

9

7

8OM

e

[26]

Know

nas

oleano

licacid

andb-sitosterolcom

poun

ds

(A)D

engibsin

R=H

OH

OH

OR1

23

9a

8a

4a

4b

45

6

9

7

8OM

e

[26]

(B)C

yprip

edin

R=OMe

O

RO

HO

OM

e1

2

3

8a

4a

4b

45

6

910

10a

7

8

[26]

(C)G

igantol

(D)M

oscatilin

(E)T

ristin

R=OHR

=HR

=OMe

R=R=OMeR=OH

R=R=OHR

=H

R

OH

OM

e

R998400 R998400998400

[26]

(F)N

aringenin

(G)H

omoerio

dictyol

R=H

R=OMe

OOO

H

OH

HO

R[26]


Table1Con

tinued

Species

Con

stituent

Chem

icalform

ula

Structures

ofcompo

und

Reference

(H)M

oscatin

mdashO

H

HO

OM

e

[26]

(I)2


etho

xyph

enanthrene

mdashO

H

HO

OM

e

OM

e

MeO

[26]

(J)4

7-dihydroxy-2-metho

xy-910

-dihydroph

enanthrene

mdash

OH

HO

OM

e[26]

(K)S

coparone

(L)S

copo

letin

(M)A

yapin

R=R=OMe

R=OMeR=OH

R+R=OCH

2OO

O

R R998400[26]

Dlongicornu

Mon

oaromatic

compo

unds


Dibutylph

thalate

CH2C

H(C

2H5)(C

H2)

3CH

3(C

H2)

3CH

3

O O

OR

OR

[27]

Ethylh

aematom

mate

C 11H

12O

5

HO

CHO

OH

COO

C 2H5

CH3

[27]


Table1Con

tinued

Species

Con

stituent

Chem

icalform

ula

Structures

ofcompo

und

Reference

MethylB

-orcinolcarboxylate

C 10H

12O

4

HO

OH

CH3

H3C

COO

CH3

[27]

N-D

ocosyltra

ns-fe

rulate

Ferulaldehyde

R=CO

OCH

2(CH

2)20CH

3R=CH

O

R

HH

OH

OCH

3

[27]

Dn

obile

Sesquiterpenes

(Dendron

obilins

A)

Cop

acam

phane-type

(1R2R

4S5S6S8S9R)-28-

Dihydroxycopacamph

an-15-on

eH H

H

H

H

O

HO

OH

(R)

11 109

7

15

1214

13

16 5

(R) (R)

(S)

(S)

(S)

(S)

[28]

Picrotoxane-type


-3(15)-lacton

e

H

H H

H

H

O O

HO

OH

OH

1214

15

133

11

110

9

6[28]


Table1Con

tinued

Species

Con

stituent

Chem

icalform

ula

Structures

ofcompo

und

Reference

Picrotoxane-type

(2b3b5b9a11b)-211-Epo

xy-91113


cton

e

H

HHH

H H

OO O

HO H

O

OH

123

14

15

56

9 1

11 10 13

[28]

Picrotoxane-type

(2b3b5b12Rlowast

)-21113

-Trih

ydroxy-


e

H

HHH

H H

O O

HO H

O

OH

1214

15

567

91

11

10 13(R

lowast)

[28]

Picrotoxane-type


-Trih

ydroxy-


eO O

H HH

HH

H

HO H

O

OH

1215569

110

11

7

1314

(Slowast

)

[28]


Table1Con

tinued

Species

Con

stituent

Chem

icalform

ula

Structures

ofcompo

und

Reference

Picrotoxane-type

(2b3b5b9a)-10

-Cyclo-21113

-trihydroxy-


eO O

H HH

H H HO

HO

OH

121556

9 110

11

7

1314

[28]

Muu

rolene-ty

pe(9b10a)-M

uurol-4

-ene-910

11-tr

iol

H

HHH

HO

OH

OH

12

15 69

110

11

4

2

1314

[28]

Allo

arom

adendrene-type

(10a)-A

lloarom

adendrene-1012

14-tr

iol

H

H

HH

H

HO

OH

OH 12

15

6

91

10

1142

1314

5[28]

Cyclo

copacamph

ane-type

(5b)-C

yclocopacamph

ane-51215

-triol

H

1

14

10

7 24

35

6

1512

1311 H

HH

H

H

HO

OH

OH

[28]


ble1Con

tinued

Species

Con

stituent

Chem

icalform

ula

Structures

ofcompo

und

Reference

Bibenzylderiv

atives

Dendron

opheno

lA221015840991015840-Tetrametho

xy131015840141015840-peroxy-111015840-


OO

MeO

MeO

OM

e

OM

eHO

OH

12

3 4

56

7

8

9

10

1112

13

14

15

161998400

2998400

3998400

4998400

5998400

6998400

7998400

8998400

9998400

10998400

11998400

12998400

13998400

14998400

15998400

16998400

[29]

Dendron

opheno

lB1-(2101584061015840-D

imetho


prop

yl)-29-dimetho


O

OH

OH

OM

eO

MeO

OM

e

OM

e 12

3 4

56

7

8

9

10

1112

13

14

15

161998400

2998400

3998400

4998400

5998400

6998400

7998400

8998400 9998400

10998400

11998400

[29]

Dthyrsiflorum

Bi-bicyclic

andbi-tr

icyclic

compo

unds

Denthyrsin

[3-(5101584061015840-D

imetho


dimetho

xy-2H-chrom

en-2-one

O

OO 1

23

45

678

9 10

1998400

2998400

3998400

4998400

59984006998400

7998400

8998400

9998400

H3CO

H3CO

OCH

3

OCH

3

[30]

Denthyrsin

ol(451015840-D

imetho


25410158407-tetraol

OCH

3

OCH

3

OH

OH

OH

OH

1

2

34

4a

4b

56

7

88

a

910

10a

1998400 3998400

2998400

49984004

a9984004

b998400

5998400

6998400

7998400

8998400

8a998400

9998400

10998400

10a998400

[30]


Table1Con

tinued

Species

Con

stituent

Chem

icalform

ula

Structures

ofcompo

und

Reference

Denthyrsin

one

(74101584071015840-Trih

ydroxy-22101584081015840-tr

imetho

xy-


OCH

3

O

O

OH

OH

OH

12

34

4a

4b

56

7

88

a910 10

a

1998400

2998400 3998400

49984004

a9984004

b998400

5998400

69984007998400

8998400

8a9984009998400

10998400

10a998400

H3CO

H3CO

[30]

Denthyrsin

in15

7-Trim

etho

xyph

enanthrene-26-diol

OCH

3

OH

H3CO

H3CO

HO

[30]

Scop

aron

emdash

OO

H3CO

H3CO

[30]

b-Sitoste

rol

mdash

OCH

3

OH

OH

[30]

Daucoste

rol

mdash

OCH

3

OH

OH

[30]



ABTSradicals

Hydroxylradicals

DPPHradicals






50
































1= R2=

OCH3R3= OH R

4= H (4) R

1= R2= R3= OCH

3R4= H

(5) R1= R2= OH R

3= R4= H (6) R

1= R3= OCH

3R2

= OH R4= H (7) R

1= OCH

3R2= R3= OH R

4= H (8)

R1= R3= OH R

2= R4= H (9) and R

1= R3= OH R

2=

HR4= OCH




1= R3= OH R

2= R5= OCH

3 R4= H(A)

R1= R4= R5= OH R

2= H R

3= OCH

3(B) R

1= R5=

OH R2= R3= OCH

3 R4= H(C) R

1= R2= OCH

3 R3=

R5= OH R

4= H(D) R

1= H R

2= R3= OH(E) R

1= H

R2= OH R

3= OCH

3(F) R

1= OCH

3 R2= R4= OH R

3

= R5= H(G) R

1= R3= OH R

2= OCH

3(H) R

1= R5=

OH R2= R4= H R

3= OCH

3(I) R1= R3= OCH

3 R2=

R5= OH R

4= H(J) R

1= R2= R4= OH R

3= OCH

3 R5=

H(K) R1= OCH

3 R2= R4= H R

3= R5= OH(L) and

R1= R2= R3= OH R







Dloddigesii


Dnobile










50values




Polysaccharide

HPS-IB23



OAc3 120572-D-Gal 120572-D-Gal



GM-CSFuarr












T cell B cell

D nobile


D moniliforme


































Table 7 Continued







[58]











4 Conclusion






Acknowledgments


References












































































































of






Disease Markers



OncologyJournal of





PPAR Research



Journal of

ObesityJournal of

















Table1Th

ecom

poun

dsof

vario

usDendrobium

species

Species

Con

stituent

Chem

icalform

ula

Structures

ofcompo

und

Reference

Da

moenu

mBibenzylsd

erivatives

Amoenylin

R 1=R 3

=MeR 2

=OHR

4=HR

5=OMe

1

23

456

AB

120572

120572998400

1998400

2998400

3998400

4998400

5998400

6998400

OR 1

R 2

OR 3

R 4

R 5[19

]

Isoamoenylin

R 1=R 3

=MeR 2

=OMeR 4

=OHR

5=H

Moscatilin

(analogues)

mdash341015840-D

ihydroxy-5-m

etho

xybibenzyl

mdashmdash

R 1=R 2

=R 4

=HR

3=MeR 5

=OH

mdashR 1

=R 3

=MeR 2

=OHR

4=HR

5=OMe

mdashR 1

=R 3

=MeR 2

=OAc

R4=HR

5=OMe

mdashR 1

=R 3

=MeR 2

=OMeR 4

=OAc

R5=H

mdashR 1

=Ac

R2=R 4

=HR

3=MeR 5

=OAc

mdashR 1

=R 3

=MeR 2

=R 5

=OHR

4=OMe

mdashR 1

=R 3

=MeR 2

=R 4

=OMeR 5

=OH

mdashR 1

=R 3

=MeR 2

=R 5

=OMeR 4

=OAc

mdashR 1

=R 2

=R 5

=HR

3=MeR 4

=OH

mdashR 1

=Ac

R2=R 5

=HR

3=MeR 4

=OAc

mdashR 1

=R 2

=R 3

=R 4

=HR

5=OH

Dc

andidu

mBibenzylsd

erivatives

DendrocandinC

((S)-344-tr


etho

xybibenzyl)

DendrocandinD

((S)-344-tr

ihydroxy-5-m

etho


DendrocandinE

(3344-te

trahydroxy-5-m

etho

xybibenzyl)

R 1=R 2

=R 5

=OHR

3=R 6

=OCH

3R 4

=H

R 1=R 2

=R 5

=OHR

3=OCH

3R 6

=OCH

2CH

3R 4

=H

R 1=R 2

=R 4

=R 5

=OHR

3=OCH

3R 6

=H

1

23

4

56

120572

120572998400

1998400

2998400

3998400

4998400

5998400

6998400

R 1

R 2

R 3

R 4

R 5

R 6

[20]

Amotin

(type

1sesquiterpenoids)

mdash

HO

OH

O

O

OO

Me

HH

[19]


Table1Con

tinued

Species

Con

stituent

Chem

icalform

ula

Structures

ofcompo

und

Reference

Amoenin(ty


mdash

HO HO

OH

O Me

H

OO

[19]

Flaccidin(910

-dihydroph

enanthropyran)

mdash

O

HO

OM

e

OH

[19]

Bibenzylsd

erivatives

44-Dihydroxy-35-dim

etho

xybibenzyl


xybibenzyl

3-O-M

ethylgigantol

Dendrop

heno

lGigantol

New

compo

unds

DendrocandinA


imetho

xybibenzyl)

R 2=R 5

=OHR

1=R 3

=OCH

3R 4

=R 6

=OH

R 1=R 2

=OHR

3=R 5

=OCH

3R 4

=R 6

=OH

R 1=OHR

3=R 4

=R 5

=OCH

3R 2

=R 6

=H

R 2=R 4

=R 5

=OHR

1=R 3

=OCH

3R 6

=H

R 1=R 5

=OHR

3=R 4

=OCH

3R 2

=R 6

=H

R 1=R 2

=OHR

3=R 5

=R 6

=OCH

3R 4

=H

1

23

4

56

120572

120572998400

1998400

2998400

3998400

4998400

5998400

6998400

R 1

R 2

R 3

R 4

R 5

R 6

[21]

DendrocandinB


xyph

enyl)-2-

hydroxym

ethyl-8

-metho

xy-23-

dihydrob


etho

xyl

benzene)

mdashOO

12

345

6

120572120572998400

1998400

2998400

3998400 4998400

5998400

6998400

1998400998400

2998400998400

3998400998400 4998400998400

5998400998400

6998400998400

7998400998400

8998400998400

9998400998400

H3CO

OCH

3

OCH

3

OCH

3

OH

OH

[21]


Table1Con

tinued

Species

Con

stituent

Chem

icalform

ula

Structures

ofcompo

und

Reference

Da

phyllum

Aromaticcompo

unds

Flavanthrin

mdash

OCH

3

OCH

3

OH

OH

HO

HO

[22]

Coelonin

Iusia

nthridin

R 1=OHR

2=OMe

R 1=OMeR 2

=OH

HO

R 1

R 2

[22]

Moscatin

mdashO

H

OH

OM

e

[22]

Gigantol

Batatasin

III

R 1=R 3

=OMeR 2

=OH

R 1=OHR

2=HR

3=OMe

HO

R 1

R 2

R 3

[22]


Table1Con

tinued

Species

Con

stituent

Chem

icalform

ula

Structures

ofcompo

und

Reference

Dibutylph

thalate

Diisob

utylph

thalate

R=CH

2CH

2CH

2CH

3R=CH

2CH(C

H3)

2

CCO

R

OR

O O

[22]


icmethyleste

rmdash

COO

Me

OH

[22]

Dc

ariniferum

Phenanthrenequ

inon

e

Dendron


xy-910

-dihydro-14-

phenanthrenequ

inon

e)mdash

O

MeO

OH

2

34

110

a8a

87

65

4b4a

109

O

[23]

Dc

hrysotoxum

Aromaticorganicc

ompo

unds

(Fluorenon

es)

Dendrofl

orin

DenchrysanA

R 1=HR

2=OH

R 1=OHR

2=H

O

OCH

3

OH

OH

R 1R 2

[24]

145-tr

ihydroxy-7-m

etho

xy-9H-fluo

ren-9-on

emdash

OCH

3

OH

OH 4

56 7

89

123

8a9a4a

4b

OH

O

[24]


Table1Con

tinued

Species

Con

stituent

Chem

icalform

ula

Structures

ofcompo

und

Reference

(Fluorenol)

(9R)-4metho

xy-9H-fluo

rene-259-tr

iol

R=H

OR

OR

RO

OM

e

[25]

Phenanthrene

27-dihydroxy-8m

etho

xyph


5(5H

)-on

emdash

O

O

OH

OH

OM

e

[25]

Dd

ensifl

orum

Bibenzyl

Densifl

orolA

mdash

O

MeO

O

OH

1

2

33

a4

5

6

77

a

1998400

2998400

1998400998400

2998400998400

3998400998400

49984009984005998400998400

6998400998400

7998400998400

[26]

Phenanthrenedion

e

Densifl

orolB

R=H

HO

1

2

3

4a 10

a8

a

4b

45

6

910

7

8

OM

e

O

O

R

[26]


Table1Con

tinued

Species

Con

stituent

Chem

icalform

ula

Structures

ofcompo

und

Reference

Dendrofl

orin

R=OH

OH

OH

OR1

234

a

9a

8a

4b

45

6

9

7

8OM

e

[26]

Know

nas

oleano

licacid

andb-sitosterolcom

poun

ds

(A)D

engibsin

R=H

OH

OH

OR1

23

9a

8a

4a

4b

45

6

9

7

8OM

e

[26]

(B)C

yprip

edin

R=OMe

O

RO

HO

OM

e1

2

3

8a

4a

4b

45

6

910

10a

7

8

[26]

(C)G

igantol

(D)M

oscatilin

(E)T

ristin

R=OHR

=HR

=OMe

R=R=OMeR=OH

R=R=OHR

=H

R

OH

OM

e

R998400 R998400998400

[26]

(F)N

aringenin

(G)H

omoerio

dictyol

R=H

R=OMe

OOO

H

OH

HO

R[26]


Table1Con

tinued

Species

Con

stituent

Chem

icalform

ula

Structures

ofcompo

und

Reference

(H)M

oscatin

mdashO

H

HO

OM

e

[26]

(I)2


etho

xyph

enanthrene

mdashO

H

HO

OM

e

OM

e

MeO

[26]

(J)4

7-dihydroxy-2-metho

xy-910

-dihydroph

enanthrene

mdash

OH

HO

OM

e[26]

(K)S

coparone

(L)S

copo

letin

(M)A

yapin

R=R=OMe

R=OMeR=OH

R+R=OCH

2OO

O

R R998400[26]

Dlongicornu

Mon

oaromatic

compo

unds


Dibutylph

thalate

CH2C

H(C

2H5)(C

H2)

3CH

3(C

H2)

3CH

3

O O

OR

OR

[27]

Ethylh

aematom

mate

C 11H

12O

5

HO

CHO

OH

COO

C 2H5

CH3

[27]


Table1Con

tinued

Species

Con

stituent

Chem

icalform

ula

Structures

ofcompo

und

Reference

MethylB

-orcinolcarboxylate

C 10H

12O

4

HO

OH

CH3

H3C

COO

CH3

[27]

N-D

ocosyltra

ns-fe

rulate

Ferulaldehyde

R=CO

OCH

2(CH

2)20CH

3R=CH

O

R

HH

OH

OCH

3

[27]

Dn

obile

Sesquiterpenes

(Dendron

obilins

A)

Cop

acam

phane-type

(1R2R

4S5S6S8S9R)-28-

Dihydroxycopacamph

an-15-on

eH H

H

H

H

O

HO

OH

(R)

11 109

7

15

1214

13

16 5

(R) (R)

(S)

(S)

(S)

(S)

[28]

Picrotoxane-type


-3(15)-lacton

e

H

H H

H

H

O O

HO

OH

OH

1214

15

133

11

110

9

6[28]


Table1Con

tinued

Species

Con

stituent

Chem

icalform

ula

Structures

ofcompo

und

Reference

Picrotoxane-type

(2b3b5b9a11b)-211-Epo

xy-91113


cton

e

H

HHH

H H

OO O

HO H

O

OH

123

14

15

56

9 1

11 10 13

[28]

Picrotoxane-type

(2b3b5b12Rlowast

)-21113

-Trih

ydroxy-


e

H

HHH

H H

O O

HO H

O

OH

1214

15

567

91

11

10 13(R

lowast)

[28]

Picrotoxane-type


-Trih

ydroxy-


eO O

H HH

HH

H

HO H

O

OH

1215569

110

11

7

1314

(Slowast

)

[28]


Table1Con

tinued

Species

Con

stituent

Chem

icalform

ula

Structures

ofcompo

und

Reference

Picrotoxane-type

(2b3b5b9a)-10

-Cyclo-21113

-trihydroxy-


eO O

H HH

H H HO

HO

OH

121556

9 110

11

7

1314

[28]

Muu

rolene-ty

pe(9b10a)-M

uurol-4

-ene-910

11-tr

iol

H

HHH

HO

OH

OH

12

15 69

110

11

4

2

1314

[28]

Allo

arom

adendrene-type

(10a)-A

lloarom

adendrene-1012

14-tr

iol

H

H

HH

H

HO

OH

OH 12

15

6

91

10

1142

1314

5[28]

Cyclo

copacamph

ane-type

(5b)-C

yclocopacamph

ane-51215

-triol

H

1

14

10

7 24

35

6

1512

1311 H

HH

H

H

HO

OH

OH

[28]


ble1Con

tinued

Species

Con

stituent

Chem

icalform

ula

Structures

ofcompo

und

Reference

Bibenzylderiv

atives

Dendron

opheno

lA221015840991015840-Tetrametho

xy131015840141015840-peroxy-111015840-


OO

MeO

MeO

OM

e

OM

eHO

OH

12

3 4

56

7

8

9

10

1112

13

14

15

161998400

2998400

3998400

4998400

5998400

6998400

7998400

8998400

9998400

10998400

11998400

12998400

13998400

14998400

15998400

16998400

[29]

Dendron

opheno

lB1-(2101584061015840-D

imetho


prop

yl)-29-dimetho


O

OH

OH

OM

eO

MeO

OM

e

OM

e 12

3 4

56

7

8

9

10

1112

13

14

15

161998400

2998400

3998400

4998400

5998400

6998400

7998400

8998400 9998400

10998400

11998400

[29]

Dthyrsiflorum

Bi-bicyclic

andbi-tr

icyclic

compo

unds

Denthyrsin

[3-(5101584061015840-D

imetho


dimetho

xy-2H-chrom

en-2-one

O

OO 1

23

45

678

9 10

1998400

2998400

3998400

4998400

59984006998400

7998400

8998400

9998400

H3CO

H3CO

OCH

3

OCH

3

[30]

Denthyrsin

ol(451015840-D

imetho


25410158407-tetraol

OCH

3

OCH

3

OH

OH

OH

OH

1

2

34

4a

4b

56

7

88

a

910

10a

1998400 3998400

2998400

49984004

a9984004

b998400

5998400

6998400

7998400

8998400

8a998400

9998400

10998400

10a998400

[30]


Table1Con

tinued

Species

Con

stituent

Chem

icalform

ula

Structures

ofcompo

und

Reference

Denthyrsin

one

(74101584071015840-Trih

ydroxy-22101584081015840-tr

imetho

xy-


OCH

3

O

O

OH

OH

OH

12

34

4a

4b

56

7

88

a910 10

a

1998400

2998400 3998400

49984004

a9984004

b998400

5998400

69984007998400

8998400

8a9984009998400

10998400

10a998400

H3CO

H3CO

[30]

Denthyrsin

in15

7-Trim

etho

xyph

enanthrene-26-diol

OCH

3

OH

H3CO

H3CO

HO

[30]

Scop

aron

emdash

OO

H3CO

H3CO

[30]

b-Sitoste

rol

mdash

OCH

3

OH

OH

[30]

Daucoste

rol

mdash

OCH

3

OH

OH

[30]



ABTSradicals

Hydroxylradicals

DPPHradicals






50
































1= R2=

OCH3R3= OH R

4= H (4) R

1= R2= R3= OCH

3R4= H

(5) R1= R2= OH R

3= R4= H (6) R

1= R3= OCH

3R2

= OH R4= H (7) R

1= OCH

3R2= R3= OH R

4= H (8)

R1= R3= OH R

2= R4= H (9) and R

1= R3= OH R

2=

HR4= OCH




1= R3= OH R

2= R5= OCH

3 R4= H(A)

R1= R4= R5= OH R

2= H R

3= OCH

3(B) R

1= R5=

OH R2= R3= OCH

3 R4= H(C) R

1= R2= OCH

3 R3=

R5= OH R

4= H(D) R

1= H R

2= R3= OH(E) R

1= H

R2= OH R

3= OCH

3(F) R

1= OCH

3 R2= R4= OH R

3

= R5= H(G) R

1= R3= OH R

2= OCH

3(H) R

1= R5=

OH R2= R4= H R

3= OCH

3(I) R1= R3= OCH

3 R2=

R5= OH R

4= H(J) R

1= R2= R4= OH R

3= OCH

3 R5=

H(K) R1= OCH

3 R2= R4= H R

3= R5= OH(L) and

R1= R2= R3= OH R







Dloddigesii


Dnobile










50values




Polysaccharide

HPS-IB23



OAc3 120572-D-Gal 120572-D-Gal



GM-CSFuarr












T cell B cell

D nobile


D moniliforme


































Table 7 Continued







[58]











4 Conclusion






Acknowledgments


References












































































































of






Disease Markers



OncologyJournal of





PPAR Research



Journal of

ObesityJournal of

















Table1Con

tinued

Species

Con

stituent

Chem

icalform

ula

Structures

ofcompo

und

Reference

Amoenin(ty


mdash

HO HO

OH

O Me

H

OO

[19]

Flaccidin(910

-dihydroph

enanthropyran)

mdash

O

HO

OM

e

OH

[19]

Bibenzylsd

erivatives

44-Dihydroxy-35-dim

etho

xybibenzyl


xybibenzyl

3-O-M

ethylgigantol

Dendrop

heno

lGigantol

New

compo

unds

DendrocandinA


imetho

xybibenzyl)

R 2=R 5

=OHR

1=R 3

=OCH

3R 4

=R 6

=OH

R 1=R 2

=OHR

3=R 5

=OCH

3R 4

=R 6

=OH

R 1=OHR

3=R 4

=R 5

=OCH

3R 2

=R 6

=H

R 2=R 4

=R 5

=OHR

1=R 3

=OCH

3R 6

=H

R 1=R 5

=OHR

3=R 4

=OCH

3R 2

=R 6

=H

R 1=R 2

=OHR

3=R 5

=R 6

=OCH

3R 4

=H

1

23

4

56

120572

120572998400

1998400

2998400

3998400

4998400

5998400

6998400

R 1

R 2

R 3

R 4

R 5

R 6

[21]

DendrocandinB


xyph

enyl)-2-

hydroxym

ethyl-8

-metho

xy-23-

dihydrob


etho

xyl

benzene)

mdashOO

12

345

6

120572120572998400

1998400

2998400

3998400 4998400

5998400

6998400

1998400998400

2998400998400

3998400998400 4998400998400

5998400998400

6998400998400

7998400998400

8998400998400

9998400998400

H3CO

OCH

3

OCH

3

OCH

3

OH

OH

[21]


Table1Con

tinued

Species

Con

stituent

Chem

icalform

ula

Structures

ofcompo

und

Reference

Da

phyllum

Aromaticcompo

unds

Flavanthrin

mdash

OCH

3

OCH

3

OH

OH

HO

HO

[22]

Coelonin

Iusia

nthridin

R 1=OHR

2=OMe

R 1=OMeR 2

=OH

HO

R 1

R 2

[22]

Moscatin

mdashO

H

OH

OM

e

[22]

Gigantol

Batatasin

III

R 1=R 3

=OMeR 2

=OH

R 1=OHR

2=HR

3=OMe

HO

R 1

R 2

R 3

[22]


Table1Con

tinued

Species

Con

stituent

Chem

icalform

ula

Structures

ofcompo

und

Reference

Dibutylph

thalate

Diisob

utylph

thalate

R=CH

2CH

2CH

2CH

3R=CH

2CH(C

H3)

2

CCO

R

OR

O O

[22]


icmethyleste

rmdash

COO

Me

OH

[22]

Dc

ariniferum

Phenanthrenequ

inon

e

Dendron


xy-910

-dihydro-14-

phenanthrenequ

inon

e)mdash

O

MeO

OH

2

34

110

a8a

87

65

4b4a

109

O

[23]

Dc

hrysotoxum

Aromaticorganicc

ompo

unds

(Fluorenon

es)

Dendrofl

orin

DenchrysanA

R 1=HR

2=OH

R 1=OHR

2=H

O

OCH

3

OH

OH

R 1R 2

[24]

145-tr

ihydroxy-7-m

etho

xy-9H-fluo

ren-9-on

emdash

OCH

3

OH

OH 4

56 7

89

123

8a9a4a

4b

OH

O

[24]


Table1Con

tinued

Species

Con

stituent

Chem

icalform

ula

Structures

ofcompo

und

Reference

(Fluorenol)

(9R)-4metho

xy-9H-fluo

rene-259-tr

iol

R=H

OR

OR

RO

OM

e

[25]

Phenanthrene

27-dihydroxy-8m

etho

xyph


5(5H

)-on

emdash

O

O

OH

OH

OM

e

[25]

Dd

ensifl

orum

Bibenzyl

Densifl

orolA

mdash

O

MeO

O

OH

1

2

33

a4

5

6

77

a

1998400

2998400

1998400998400

2998400998400

3998400998400

49984009984005998400998400

6998400998400

7998400998400

[26]

Phenanthrenedion

e

Densifl

orolB

R=H

HO

1

2

3

4a 10

a8

a

4b

45

6

910

7

8

OM

e

O

O

R

[26]


Table1Con

tinued

Species

Con

stituent

Chem

icalform

ula

Structures

ofcompo

und

Reference

Dendrofl

orin

R=OH

OH

OH

OR1

234

a

9a

8a

4b

45

6

9

7

8OM

e

[26]

Know

nas

oleano

licacid

andb-sitosterolcom

poun

ds

(A)D

engibsin

R=H

OH

OH

OR1

23

9a

8a

4a

4b

45

6

9

7

8OM

e

[26]

(B)C

yprip

edin

R=OMe

O

RO

HO

OM

e1

2

3

8a

4a

4b

45

6

910

10a

7

8

[26]

(C)G

igantol

(D)M

oscatilin

(E)T

ristin

R=OHR

=HR

=OMe

R=R=OMeR=OH

R=R=OHR

=H

R

OH

OM

e

R998400 R998400998400

[26]

(F)N

aringenin

(G)H

omoerio

dictyol

R=H

R=OMe

OOO

H

OH

HO

R[26]


Table1Con

tinued

Species

Con

stituent

Chem

icalform

ula

Structures

ofcompo

und

Reference

(H)M

oscatin

mdashO

H

HO

OM

e

[26]

(I)2


etho

xyph

enanthrene

mdashO

H

HO

OM

e

OM

e

MeO

[26]

(J)4

7-dihydroxy-2-metho

xy-910

-dihydroph

enanthrene

mdash

OH

HO

OM

e[26]

(K)S

coparone

(L)S

copo

letin

(M)A

yapin

R=R=OMe

R=OMeR=OH

R+R=OCH

2OO

O

R R998400[26]

Dlongicornu

Mon

oaromatic

compo

unds


Dibutylph

thalate

CH2C

H(C

2H5)(C

H2)

3CH

3(C

H2)

3CH

3

O O

OR

OR

[27]

Ethylh

aematom

mate

C 11H

12O

5

HO

CHO

OH

COO

C 2H5

CH3

[27]


Table1Con

tinued

Species

Con

stituent

Chem

icalform

ula

Structures

ofcompo

und

Reference

MethylB

-orcinolcarboxylate

C 10H

12O

4

HO

OH

CH3

H3C

COO

CH3

[27]

N-D

ocosyltra

ns-fe

rulate

Ferulaldehyde

R=CO

OCH

2(CH

2)20CH

3R=CH

O

R

HH

OH

OCH

3

[27]

Dn

obile

Sesquiterpenes

(Dendron

obilins

A)

Cop

acam

phane-type

(1R2R

4S5S6S8S9R)-28-

Dihydroxycopacamph

an-15-on

eH H

H

H

H

O

HO

OH

(R)

11 109

7

15

1214

13

16 5

(R) (R)

(S)

(S)

(S)

(S)

[28]

Picrotoxane-type


-3(15)-lacton

e

H

H H

H

H

O O

HO

OH

OH

1214

15

133

11

110

9

6[28]


Table1Con

tinued

Species

Con

stituent

Chem

icalform

ula

Structures

ofcompo

und

Reference

Picrotoxane-type

(2b3b5b9a11b)-211-Epo

xy-91113


cton

e

H

HHH

H H

OO O

HO H

O

OH

123

14

15

56

9 1

11 10 13

[28]

Picrotoxane-type

(2b3b5b12Rlowast

)-21113

-Trih

ydroxy-


e

H

HHH

H H

O O

HO H

O

OH

1214

15

567

91

11

10 13(R

lowast)

[28]

Picrotoxane-type


-Trih

ydroxy-


eO O

H HH

HH

H

HO H

O

OH

1215569

110

11

7

1314

(Slowast

)

[28]


Table1Con

tinued

Species

Con

stituent

Chem

icalform

ula

Structures

ofcompo

und

Reference

Picrotoxane-type

(2b3b5b9a)-10

-Cyclo-21113

-trihydroxy-


eO O

H HH

H H HO

HO

OH

121556

9 110

11

7

1314

[28]

Muu

rolene-ty

pe(9b10a)-M

uurol-4

-ene-910

11-tr

iol

H

HHH

HO

OH

OH

12

15 69

110

11

4

2

1314

[28]

Allo

arom

adendrene-type

(10a)-A

lloarom

adendrene-1012

14-tr

iol

H

H

HH

H

HO

OH

OH 12

15

6

91

10

1142

1314

5[28]

Cyclo

copacamph

ane-type

(5b)-C

yclocopacamph

ane-51215

-triol

H

1

14

10

7 24

35

6

1512

1311 H

HH

H

H

HO

OH

OH

[28]


ble1Con

tinued

Species

Con

stituent

Chem

icalform

ula

Structures

ofcompo

und

Reference

Bibenzylderiv

atives

Dendron

opheno

lA221015840991015840-Tetrametho

xy131015840141015840-peroxy-111015840-


OO

MeO

MeO

OM

e

OM

eHO

OH

12

3 4

56

7

8

9

10

1112

13

14

15

161998400

2998400

3998400

4998400

5998400

6998400

7998400

8998400

9998400

10998400

11998400

12998400

13998400

14998400

15998400

16998400

[29]

Dendron

opheno

lB1-(2101584061015840-D

imetho


prop

yl)-29-dimetho


O

OH

OH

OM

eO

MeO

OM

e

OM

e 12

3 4

56

7

8

9

10

1112

13

14

15

161998400

2998400

3998400

4998400

5998400

6998400

7998400

8998400 9998400

10998400

11998400

[29]

Dthyrsiflorum

Bi-bicyclic

andbi-tr

icyclic

compo

unds

Denthyrsin

[3-(5101584061015840-D

imetho


dimetho

xy-2H-chrom

en-2-one

O

OO 1

23

45

678

9 10

1998400

2998400

3998400

4998400

59984006998400

7998400

8998400

9998400

H3CO

H3CO

OCH

3

OCH

3

[30]

Denthyrsin

ol(451015840-D

imetho


25410158407-tetraol

OCH

3

OCH

3

OH

OH

OH

OH

1

2

34

4a

4b

56

7

88

a

910

10a

1998400 3998400

2998400

49984004

a9984004

b998400

5998400

6998400

7998400

8998400

8a998400

9998400

10998400

10a998400

[30]


Table1Con

tinued

Species

Con

stituent

Chem

icalform

ula

Structures

ofcompo

und

Reference

Denthyrsin

one

(74101584071015840-Trih

ydroxy-22101584081015840-tr

imetho

xy-


OCH

3

O

O

OH

OH

OH

12

34

4a

4b

56

7

88

a910 10

a

1998400

2998400 3998400

49984004

a9984004

b998400

5998400

69984007998400

8998400

8a9984009998400

10998400

10a998400

H3CO

H3CO

[30]

Denthyrsin

in15

7-Trim

etho

xyph

enanthrene-26-diol

OCH

3

OH

H3CO

H3CO

HO

[30]

Scop

aron

emdash

OO

H3CO

H3CO

[30]

b-Sitoste

rol

mdash

OCH

3

OH

OH

[30]

Daucoste

rol

mdash

OCH

3

OH

OH

[30]



ABTSradicals

Hydroxylradicals

DPPHradicals






50
































1= R2=

OCH3R3= OH R

4= H (4) R

1= R2= R3= OCH

3R4= H

(5) R1= R2= OH R

3= R4= H (6) R

1= R3= OCH

3R2

= OH R4= H (7) R

1= OCH

3R2= R3= OH R

4= H (8)

R1= R3= OH R

2= R4= H (9) and R

1= R3= OH R

2=

HR4= OCH




1= R3= OH R

2= R5= OCH

3 R4= H(A)

R1= R4= R5= OH R

2= H R

3= OCH

3(B) R

1= R5=

OH R2= R3= OCH

3 R4= H(C) R

1= R2= OCH

3 R3=

R5= OH R

4= H(D) R

1= H R

2= R3= OH(E) R

1= H

R2= OH R

3= OCH

3(F) R

1= OCH

3 R2= R4= OH R

3

= R5= H(G) R

1= R3= OH R

2= OCH

3(H) R

1= R5=

OH R2= R4= H R

3= OCH

3(I) R1= R3= OCH

3 R2=

R5= OH R

4= H(J) R

1= R2= R4= OH R

3= OCH

3 R5=

H(K) R1= OCH

3 R2= R4= H R

3= R5= OH(L) and

R1= R2= R3= OH R







Dloddigesii


Dnobile










50values




Polysaccharide

HPS-IB23



OAc3 120572-D-Gal 120572-D-Gal



GM-CSFuarr












T cell B cell

D nobile


D moniliforme


































Table 7 Continued







[58]











4 Conclusion






Acknowledgments


References












































































































of






Disease Markers



OncologyJournal of





PPAR Research



Journal of

ObesityJournal of

















Table1Con

tinued

Species

Con

stituent

Chem

icalform

ula

Structures

ofcompo

und

Reference

Da

phyllum

Aromaticcompo

unds

Flavanthrin

mdash

OCH

3

OCH

3

OH

OH

HO

HO

[22]

Coelonin

Iusia

nthridin

R 1=OHR

2=OMe

R 1=OMeR 2

=OH

HO

R 1

R 2

[22]

Moscatin

mdashO

H

OH

OM

e

[22]

Gigantol

Batatasin

III

R 1=R 3

=OMeR 2

=OH

R 1=OHR

2=HR

3=OMe

HO

R 1

R 2

R 3

[22]


Table1Con

tinued

Species

Con

stituent

Chem

icalform

ula

Structures

ofcompo

und

Reference

Dibutylph

thalate

Diisob

utylph

thalate

R=CH

2CH

2CH

2CH

3R=CH

2CH(C

H3)

2

CCO

R

OR

O O

[22]


icmethyleste

rmdash

COO

Me

OH

[22]

Dc

ariniferum

Phenanthrenequ

inon

e

Dendron


xy-910

-dihydro-14-

phenanthrenequ

inon

e)mdash

O

MeO

OH

2

34

110

a8a

87

65

4b4a

109

O

[23]

Dc

hrysotoxum

Aromaticorganicc

ompo

unds

(Fluorenon

es)

Dendrofl

orin

DenchrysanA

R 1=HR

2=OH

R 1=OHR

2=H

O

OCH

3

OH

OH

R 1R 2

[24]

145-tr

ihydroxy-7-m

etho

xy-9H-fluo

ren-9-on

emdash

OCH

3

OH

OH 4

56 7

89

123

8a9a4a

4b

OH

O

[24]


Table1Con

tinued

Species

Con

stituent

Chem

icalform

ula

Structures

ofcompo

und

Reference

(Fluorenol)

(9R)-4metho

xy-9H-fluo

rene-259-tr

iol

R=H

OR

OR

RO

OM

e

[25]

Phenanthrene

27-dihydroxy-8m

etho

xyph


5(5H

)-on

emdash

O

O

OH

OH

OM

e

[25]

Dd

ensifl

orum

Bibenzyl

Densifl

orolA

mdash

O

MeO

O

OH

1

2

33

a4

5

6

77

a

1998400

2998400

1998400998400

2998400998400

3998400998400

49984009984005998400998400

6998400998400

7998400998400

[26]

Phenanthrenedion

e

Densifl

orolB

R=H

HO

1

2

3

4a 10

a8

a

4b

45

6

910

7

8

OM

e

O

O

R

[26]


Table1Con

tinued

Species

Con

stituent

Chem

icalform

ula

Structures

ofcompo

und

Reference

Dendrofl

orin

R=OH

OH

OH

OR1

234

a

9a

8a

4b

45

6

9

7

8OM

e

[26]

Know

nas

oleano

licacid

andb-sitosterolcom

poun

ds

(A)D

engibsin

R=H

OH

OH

OR1

23

9a

8a

4a

4b

45

6

9

7

8OM

e

[26]

(B)C

yprip

edin

R=OMe

O

RO

HO

OM

e1

2

3

8a

4a

4b

45

6

910

10a

7

8

[26]

(C)G

igantol

(D)M

oscatilin

(E)T

ristin

R=OHR

=HR

=OMe

R=R=OMeR=OH

R=R=OHR

=H

R

OH

OM

e

R998400 R998400998400

[26]

(F)N

aringenin

(G)H

omoerio

dictyol

R=H

R=OMe

OOO

H

OH

HO

R[26]


Table1Con

tinued

Species

Con

stituent

Chem

icalform

ula

Structures

ofcompo

und

Reference

(H)M

oscatin

mdashO

H

HO

OM

e

[26]

(I)2


etho

xyph

enanthrene

mdashO

H

HO

OM

e

OM

e

MeO

[26]

(J)4

7-dihydroxy-2-metho

xy-910

-dihydroph

enanthrene

mdash

OH

HO

OM

e[26]

(K)S

coparone

(L)S

copo

letin

(M)A

yapin

R=R=OMe

R=OMeR=OH

R+R=OCH

2OO

O

R R998400[26]

Dlongicornu

Mon

oaromatic

compo

unds


Dibutylph

thalate

CH2C

H(C

2H5)(C

H2)

3CH

3(C

H2)

3CH

3

O O

OR

OR

[27]

Ethylh

aematom

mate

C 11H

12O

5

HO

CHO

OH

COO

C 2H5

CH3

[27]


Table1Con

tinued

Species

Con

stituent

Chem

icalform

ula

Structures

ofcompo

und

Reference

MethylB

-orcinolcarboxylate

C 10H

12O

4

HO

OH

CH3

H3C

COO

CH3

[27]

N-D

ocosyltra

ns-fe

rulate

Ferulaldehyde

R=CO

OCH

2(CH

2)20CH

3R=CH

O

R

HH

OH

OCH

3

[27]

Dn

obile

Sesquiterpenes

(Dendron

obilins

A)

Cop

acam

phane-type

(1R2R

4S5S6S8S9R)-28-

Dihydroxycopacamph

an-15-on

eH H

H

H

H

O

HO

OH

(R)

11 109

7

15

1214

13

16 5

(R) (R)

(S)

(S)

(S)

(S)

[28]

Picrotoxane-type


-3(15)-lacton

e

H

H H

H

H

O O

HO

OH

OH

1214

15

133

11

110

9

6[28]


Table1Con

tinued

Species

Con

stituent

Chem

icalform

ula

Structures

ofcompo

und

Reference

Picrotoxane-type

(2b3b5b9a11b)-211-Epo

xy-91113


cton

e

H

HHH

H H

OO O

HO H

O

OH

123

14

15

56

9 1

11 10 13

[28]

Picrotoxane-type

(2b3b5b12Rlowast

)-21113

-Trih

ydroxy-


e

H

HHH

H H

O O

HO H

O

OH

1214

15

567

91

11

10 13(R

lowast)

[28]

Picrotoxane-type


-Trih

ydroxy-


eO O

H HH

HH

H

HO H

O

OH

1215569

110

11

7

1314

(Slowast

)

[28]


Table1Con

tinued

Species

Con

stituent

Chem

icalform

ula

Structures

ofcompo

und

Reference

Picrotoxane-type

(2b3b5b9a)-10

-Cyclo-21113

-trihydroxy-


eO O

H HH

H H HO

HO

OH

121556

9 110

11

7

1314

[28]

Muu

rolene-ty

pe(9b10a)-M

uurol-4

-ene-910

11-tr

iol

H

HHH

HO

OH

OH

12

15 69

110

11

4

2

1314

[28]

Allo

arom

adendrene-type

(10a)-A

lloarom

adendrene-1012

14-tr

iol

H

H

HH

H

HO

OH

OH 12

15

6

91

10

1142

1314

5[28]

Cyclo

copacamph

ane-type

(5b)-C

yclocopacamph

ane-51215

-triol

H

1

14

10

7 24

35

6

1512

1311 H

HH

H

H

HO

OH

OH

[28]


ble1Con

tinued

Species

Con

stituent

Chem

icalform

ula

Structures

ofcompo

und

Reference

Bibenzylderiv

atives

Dendron

opheno

lA221015840991015840-Tetrametho

xy131015840141015840-peroxy-111015840-


OO

MeO

MeO

OM

e

OM

eHO

OH

12

3 4

56

7

8

9

10

1112

13

14

15

161998400

2998400

3998400

4998400

5998400

6998400

7998400

8998400

9998400

10998400

11998400

12998400

13998400

14998400

15998400

16998400

[29]

Dendron

opheno

lB1-(2101584061015840-D

imetho


prop

yl)-29-dimetho


O

OH

OH

OM

eO

MeO

OM

e

OM

e 12

3 4

56

7

8

9

10

1112

13

14

15

161998400

2998400

3998400

4998400

5998400

6998400

7998400

8998400 9998400

10998400

11998400

[29]

Dthyrsiflorum

Bi-bicyclic

andbi-tr

icyclic

compo

unds

Denthyrsin

[3-(5101584061015840-D

imetho


dimetho

xy-2H-chrom

en-2-one

O

OO 1

23

45

678

9 10

1998400

2998400

3998400

4998400

59984006998400

7998400

8998400

9998400

H3CO

H3CO

OCH

3

OCH

3

[30]

Denthyrsin

ol(451015840-D

imetho


25410158407-tetraol

OCH

3

OCH

3

OH

OH

OH

OH

1

2

34

4a

4b

56

7

88

a

910

10a

1998400 3998400

2998400

49984004

a9984004

b998400

5998400

6998400

7998400

8998400

8a998400

9998400

10998400

10a998400

[30]


Table1Con

tinued

Species

Con

stituent

Chem

icalform

ula

Structures

ofcompo

und

Reference

Denthyrsin

one

(74101584071015840-Trih

ydroxy-22101584081015840-tr

imetho

xy-


OCH

3

O

O

OH

OH

OH

12

34

4a

4b

56

7

88

a910 10

a

1998400

2998400 3998400

49984004

a9984004

b998400

5998400

69984007998400

8998400

8a9984009998400

10998400

10a998400

H3CO

H3CO

[30]

Denthyrsin

in15

7-Trim

etho

xyph

enanthrene-26-diol

OCH

3

OH

H3CO

H3CO

HO

[30]

Scop

aron

emdash

OO

H3CO

H3CO

[30]

b-Sitoste

rol

mdash

OCH

3

OH

OH

[30]

Daucoste

rol

mdash

OCH

3

OH

OH

[30]



ABTSradicals

Hydroxylradicals

DPPHradicals






50
































1= R2=

OCH3R3= OH R

4= H (4) R

1= R2= R3= OCH

3R4= H

(5) R1= R2= OH R

3= R4= H (6) R

1= R3= OCH

3R2

= OH R4= H (7) R

1= OCH

3R2= R3= OH R

4= H (8)

R1= R3= OH R

2= R4= H (9) and R

1= R3= OH R

2=

HR4= OCH




1= R3= OH R

2= R5= OCH

3 R4= H(A)

R1= R4= R5= OH R

2= H R

3= OCH

3(B) R

1= R5=

OH R2= R3= OCH

3 R4= H(C) R

1= R2= OCH

3 R3=

R5= OH R

4= H(D) R

1= H R

2= R3= OH(E) R

1= H

R2= OH R

3= OCH

3(F) R

1= OCH

3 R2= R4= OH R

3

= R5= H(G) R

1= R3= OH R

2= OCH

3(H) R

1= R5=

OH R2= R4= H R

3= OCH

3(I) R1= R3= OCH

3 R2=

R5= OH R

4= H(J) R

1= R2= R4= OH R

3= OCH

3 R5=

H(K) R1= OCH

3 R2= R4= H R

3= R5= OH(L) and

R1= R2= R3= OH R







Dloddigesii


Dnobile










50values




Polysaccharide

HPS-IB23



OAc3 120572-D-Gal 120572-D-Gal



GM-CSFuarr












T cell B cell

D nobile


D moniliforme


































Table 7 Continued







[58]











4 Conclusion






Acknowledgments


References












































































































of






Disease Markers



OncologyJournal of





PPAR Research



Journal of

ObesityJournal of

















Table1Con

tinued

Species

Con

stituent

Chem

icalform

ula

Structures

ofcompo

und

Reference

Dibutylph

thalate

Diisob

utylph

thalate

R=CH

2CH

2CH

2CH

3R=CH

2CH(C

H3)

2

CCO

R

OR

O O

[22]


icmethyleste

rmdash

COO

Me

OH

[22]

Dc

ariniferum

Phenanthrenequ

inon

e

Dendron


xy-910

-dihydro-14-

phenanthrenequ

inon

e)mdash

O

MeO

OH

2

34

110

a8a

87

65

4b4a

109

O

[23]

Dc

hrysotoxum

Aromaticorganicc

ompo

unds

(Fluorenon

es)

Dendrofl

orin

DenchrysanA

R 1=HR

2=OH

R 1=OHR

2=H

O

OCH

3

OH

OH

R 1R 2

[24]

145-tr

ihydroxy-7-m

etho

xy-9H-fluo

ren-9-on

emdash

OCH

3

OH

OH 4

56 7

89

123

8a9a4a

4b

OH

O

[24]


Table1Con

tinued

Species

Con

stituent

Chem

icalform

ula

Structures

ofcompo

und

Reference

(Fluorenol)

(9R)-4metho

xy-9H-fluo

rene-259-tr

iol

R=H

OR

OR

RO

OM

e

[25]

Phenanthrene

27-dihydroxy-8m

etho

xyph


5(5H

)-on

emdash

O

O

OH

OH

OM

e

[25]

Dd

ensifl

orum

Bibenzyl

Densifl

orolA

mdash

O

MeO

O

OH

1

2

33

a4

5

6

77

a

1998400

2998400

1998400998400

2998400998400

3998400998400

49984009984005998400998400

6998400998400

7998400998400

[26]

Phenanthrenedion

e

Densifl

orolB

R=H

HO

1

2

3

4a 10

a8

a

4b

45

6

910

7

8

OM

e

O

O

R

[26]


Table1Con

tinued

Species

Con

stituent

Chem

icalform

ula

Structures

ofcompo

und

Reference

Dendrofl

orin

R=OH

OH

OH

OR1

234

a

9a

8a

4b

45

6

9

7

8OM

e

[26]

Know

nas

oleano

licacid

andb-sitosterolcom

poun

ds

(A)D

engibsin

R=H

OH

OH

OR1

23

9a

8a

4a

4b

45

6

9

7

8OM

e

[26]

(B)C

yprip

edin

R=OMe

O

RO

HO

OM

e1

2

3

8a

4a

4b

45

6

910

10a

7

8

[26]

(C)G

igantol

(D)M

oscatilin

(E)T

ristin

R=OHR

=HR

=OMe

R=R=OMeR=OH

R=R=OHR

=H

R

OH

OM

e

R998400 R998400998400

[26]

(F)N

aringenin

(G)H

omoerio

dictyol

R=H

R=OMe

OOO

H

OH

HO

R[26]


Table1Con

tinued

Species

Con

stituent

Chem

icalform

ula

Structures

ofcompo

und

Reference

(H)M

oscatin

mdashO

H

HO

OM

e

[26]

(I)2


etho

xyph

enanthrene

mdashO

H

HO

OM

e

OM

e

MeO

[26]

(J)4

7-dihydroxy-2-metho

xy-910

-dihydroph

enanthrene

mdash

OH

HO

OM

e[26]

(K)S

coparone

(L)S

copo

letin

(M)A

yapin

R=R=OMe

R=OMeR=OH

R+R=OCH

2OO

O

R R998400[26]

Dlongicornu

Mon

oaromatic

compo

unds


Dibutylph

thalate

CH2C

H(C

2H5)(C

H2)

3CH

3(C

H2)

3CH

3

O O

OR

OR

[27]

Ethylh

aematom

mate

C 11H

12O

5

HO

CHO

OH

COO

C 2H5

CH3

[27]


Table1Con

tinued

Species

Con

stituent

Chem

icalform

ula

Structures

ofcompo

und

Reference

MethylB

-orcinolcarboxylate

C 10H

12O

4

HO

OH

CH3

H3C

COO

CH3

[27]

N-D

ocosyltra

ns-fe

rulate

Ferulaldehyde

R=CO

OCH

2(CH

2)20CH

3R=CH

O

R

HH

OH

OCH

3

[27]

Dn

obile

Sesquiterpenes

(Dendron

obilins

A)

Cop

acam

phane-type

(1R2R

4S5S6S8S9R)-28-

Dihydroxycopacamph

an-15-on

eH H

H

H

H

O

HO

OH

(R)

11 109

7

15

1214

13

16 5

(R) (R)

(S)

(S)

(S)

(S)

[28]

Picrotoxane-type


-3(15)-lacton

e

H

H H

H

H

O O

HO

OH

OH

1214

15

133

11

110

9

6[28]


Table1Con

tinued

Species

Con

stituent

Chem

icalform

ula

Structures

ofcompo

und

Reference

Picrotoxane-type

(2b3b5b9a11b)-211-Epo

xy-91113


cton

e

H

HHH

H H

OO O

HO H

O

OH

123

14

15

56

9 1

11 10 13

[28]

Picrotoxane-type

(2b3b5b12Rlowast

)-21113

-Trih

ydroxy-


e

H

HHH

H H

O O

HO H

O

OH

1214

15

567

91

11

10 13(R

lowast)

[28]

Picrotoxane-type


-Trih

ydroxy-


eO O

H HH

HH

H

HO H

O

OH

1215569

110

11

7

1314

(Slowast

)

[28]


Table1Con

tinued

Species

Con

stituent

Chem

icalform

ula

Structures

ofcompo

und

Reference

Picrotoxane-type

(2b3b5b9a)-10

-Cyclo-21113

-trihydroxy-


eO O

H HH

H H HO

HO

OH

121556

9 110

11

7

1314

[28]

Muu

rolene-ty

pe(9b10a)-M

uurol-4

-ene-910

11-tr

iol

H

HHH

HO

OH

OH

12

15 69

110

11

4

2

1314

[28]

Allo

arom

adendrene-type

(10a)-A

lloarom

adendrene-1012

14-tr

iol

H

H

HH

H

HO

OH

OH 12

15

6

91

10

1142

1314

5[28]

Cyclo

copacamph

ane-type

(5b)-C

yclocopacamph

ane-51215

-triol

H

1

14

10

7 24

35

6

1512

1311 H

HH

H

H

HO

OH

OH

[28]


ble1Con

tinued

Species

Con

stituent

Chem

icalform

ula

Structures

ofcompo

und

Reference

Bibenzylderiv

atives

Dendron

opheno

lA221015840991015840-Tetrametho

xy131015840141015840-peroxy-111015840-


OO

MeO

MeO

OM

e

OM

eHO

OH

12

3 4

56

7

8

9

10

1112

13

14

15

161998400

2998400

3998400

4998400

5998400

6998400

7998400

8998400

9998400

10998400

11998400

12998400

13998400

14998400

15998400

16998400

[29]

Dendron

opheno

lB1-(2101584061015840-D

imetho


prop

yl)-29-dimetho


O

OH

OH

OM

eO

MeO

OM

e

OM

e 12

3 4

56

7

8

9

10

1112

13

14

15

161998400

2998400

3998400

4998400

5998400

6998400

7998400

8998400 9998400

10998400

11998400

[29]

Dthyrsiflorum

Bi-bicyclic

andbi-tr

icyclic

compo

unds

Denthyrsin

[3-(5101584061015840-D

imetho


dimetho

xy-2H-chrom

en-2-one

O

OO 1

23

45

678

9 10

1998400

2998400

3998400

4998400

59984006998400

7998400

8998400

9998400

H3CO

H3CO

OCH

3

OCH

3

[30]

Denthyrsin

ol(451015840-D

imetho


25410158407-tetraol

OCH

3

OCH

3

OH

OH

OH

OH

1

2

34

4a

4b

56

7

88

a

910

10a

1998400 3998400

2998400

49984004

a9984004

b998400

5998400

6998400

7998400

8998400

8a998400

9998400

10998400

10a998400

[30]


Table1Con

tinued

Species

Con

stituent

Chem

icalform

ula

Structures

ofcompo

und

Reference

Denthyrsin

one

(74101584071015840-Trih

ydroxy-22101584081015840-tr

imetho

xy-


OCH

3

O

O

OH

OH

OH

12

34

4a

4b

56

7

88

a910 10

a

1998400

2998400 3998400

49984004

a9984004

b998400

5998400

69984007998400

8998400

8a9984009998400

10998400

10a998400

H3CO

H3CO

[30]

Denthyrsin

in15

7-Trim

etho

xyph

enanthrene-26-diol

OCH

3

OH

H3CO

H3CO

HO

[30]

Scop

aron

emdash

OO

H3CO

H3CO

[30]

b-Sitoste

rol

mdash

OCH

3

OH

OH

[30]

Daucoste

rol

mdash

OCH

3

OH

OH

[30]



ABTSradicals

Hydroxylradicals

DPPHradicals






50
































1= R2=

OCH3R3= OH R

4= H (4) R

1= R2= R3= OCH

3R4= H

(5) R1= R2= OH R

3= R4= H (6) R

1= R3= OCH

3R2

= OH R4= H (7) R

1= OCH

3R2= R3= OH R

4= H (8)

R1= R3= OH R

2= R4= H (9) and R

1= R3= OH R

2=

HR4= OCH




1= R3= OH R

2= R5= OCH

3 R4= H(A)

R1= R4= R5= OH R

2= H R

3= OCH

3(B) R

1= R5=

OH R2= R3= OCH

3 R4= H(C) R

1= R2= OCH

3 R3=

R5= OH R

4= H(D) R

1= H R

2= R3= OH(E) R

1= H

R2= OH R

3= OCH

3(F) R

1= OCH

3 R2= R4= OH R

3

= R5= H(G) R

1= R3= OH R

2= OCH

3(H) R

1= R5=

OH R2= R4= H R

3= OCH

3(I) R1= R3= OCH

3 R2=

R5= OH R

4= H(J) R

1= R2= R4= OH R

3= OCH

3 R5=

H(K) R1= OCH

3 R2= R4= H R

3= R5= OH(L) and

R1= R2= R3= OH R







Dloddigesii


Dnobile










50values




Polysaccharide

HPS-IB23



OAc3 120572-D-Gal 120572-D-Gal



GM-CSFuarr












T cell B cell

D nobile


D moniliforme


































Table 7 Continued







[58]











4 Conclusion






Acknowledgments


References












































































































of






Disease Markers



OncologyJournal of





PPAR Research



Journal of

ObesityJournal of

















Table1Con

tinued

Species

Con

stituent

Chem

icalform

ula

Structures

ofcompo

und

Reference

(Fluorenol)

(9R)-4metho

xy-9H-fluo

rene-259-tr

iol

R=H

OR

OR

RO

OM

e

[25]

Phenanthrene

27-dihydroxy-8m

etho

xyph


5(5H

)-on

emdash

O

O

OH

OH

OM

e

[25]

Dd

ensifl

orum

Bibenzyl

Densifl

orolA

mdash

O

MeO

O

OH

1

2

33

a4

5

6

77

a

1998400

2998400

1998400998400

2998400998400

3998400998400

49984009984005998400998400

6998400998400

7998400998400

[26]

Phenanthrenedion

e

Densifl

orolB

R=H

HO

1

2

3

4a 10

a8

a

4b

45

6

910

7

8

OM

e

O

O

R

[26]


Table1Con

tinued

Species

Con

stituent

Chem

icalform

ula

Structures

ofcompo

und

Reference

Dendrofl

orin

R=OH

OH

OH

OR1

234

a

9a

8a

4b

45

6

9

7

8OM

e

[26]

Know

nas

oleano

licacid

andb-sitosterolcom

poun

ds

(A)D

engibsin

R=H

OH

OH

OR1

23

9a

8a

4a

4b

45

6

9

7

8OM

e

[26]

(B)C

yprip

edin

R=OMe

O

RO

HO

OM

e1

2

3

8a

4a

4b

45

6

910

10a

7

8

[26]

(C)G

igantol

(D)M

oscatilin

(E)T

ristin

R=OHR

=HR

=OMe

R=R=OMeR=OH

R=R=OHR

=H

R

OH

OM

e

R998400 R998400998400

[26]

(F)N

aringenin

(G)H

omoerio

dictyol

R=H

R=OMe

OOO

H

OH

HO

R[26]


Table1Con

tinued

Species

Con

stituent

Chem

icalform

ula

Structures

ofcompo

und

Reference

(H)M

oscatin

mdashO

H

HO

OM

e

[26]

(I)2


etho

xyph

enanthrene

mdashO

H

HO

OM

e

OM

e

MeO

[26]

(J)4

7-dihydroxy-2-metho

xy-910

-dihydroph

enanthrene

mdash

OH

HO

OM

e[26]

(K)S

coparone

(L)S

copo

letin

(M)A

yapin

R=R=OMe

R=OMeR=OH

R+R=OCH

2OO

O

R R998400[26]

Dlongicornu

Mon

oaromatic

compo

unds


Dibutylph

thalate

CH2C

H(C

2H5)(C

H2)

3CH

3(C

H2)

3CH

3

O O

OR

OR

[27]

Ethylh

aematom

mate

C 11H

12O

5

HO

CHO

OH

COO

C 2H5

CH3

[27]


Table1Con

tinued

Species

Con

stituent

Chem

icalform

ula

Structures

ofcompo

und

Reference

MethylB

-orcinolcarboxylate

C 10H

12O

4

HO

OH

CH3

H3C

COO

CH3

[27]

N-D

ocosyltra

ns-fe

rulate

Ferulaldehyde

R=CO

OCH

2(CH

2)20CH

3R=CH

O

R

HH

OH

OCH

3

[27]

Dn

obile

Sesquiterpenes

(Dendron

obilins

A)

Cop

acam

phane-type

(1R2R

4S5S6S8S9R)-28-

Dihydroxycopacamph

an-15-on

eH H

H

H

H

O

HO

OH

(R)

11 109

7

15

1214

13

16 5

(R) (R)

(S)

(S)

(S)

(S)

[28]

Picrotoxane-type


-3(15)-lacton

e

H

H H

H

H

O O

HO

OH

OH

1214

15

133

11

110

9

6[28]


Table1Con

tinued

Species

Con

stituent

Chem

icalform

ula

Structures

ofcompo

und

Reference

Picrotoxane-type

(2b3b5b9a11b)-211-Epo

xy-91113


cton

e

H

HHH

H H

OO O

HO H

O

OH

123

14

15

56

9 1

11 10 13

[28]

Picrotoxane-type

(2b3b5b12Rlowast

)-21113

-Trih

ydroxy-


e

H

HHH

H H

O O

HO H

O

OH

1214

15

567

91

11

10 13(R

lowast)

[28]

Picrotoxane-type


-Trih

ydroxy-


eO O

H HH

HH

H

HO H

O

OH

1215569

110

11

7

1314

(Slowast

)

[28]


Table1Con

tinued

Species

Con

stituent

Chem

icalform

ula

Structures

ofcompo

und

Reference

Picrotoxane-type

(2b3b5b9a)-10

-Cyclo-21113

-trihydroxy-


eO O

H HH

H H HO

HO

OH

121556

9 110

11

7

1314

[28]

Muu

rolene-ty

pe(9b10a)-M

uurol-4

-ene-910

11-tr

iol

H

HHH

HO

OH

OH

12

15 69

110

11

4

2

1314

[28]

Allo

arom

adendrene-type

(10a)-A

lloarom

adendrene-1012

14-tr

iol

H

H

HH

H

HO

OH

OH 12

15

6

91

10

1142

1314

5[28]

Cyclo

copacamph

ane-type

(5b)-C

yclocopacamph

ane-51215

-triol

H

1

14

10

7 24

35

6

1512

1311 H

HH

H

H

HO

OH

OH

[28]


ble1Con

tinued

Species

Con

stituent

Chem

icalform

ula

Structures

ofcompo

und

Reference

Bibenzylderiv

atives

Dendron

opheno

lA221015840991015840-Tetrametho

xy131015840141015840-peroxy-111015840-


OO

MeO

MeO

OM

e

OM

eHO

OH

12

3 4

56

7

8

9

10

1112

13

14

15

161998400

2998400

3998400

4998400

5998400

6998400

7998400

8998400

9998400

10998400

11998400

12998400

13998400

14998400

15998400

16998400

[29]

Dendron

opheno

lB1-(2101584061015840-D

imetho


prop

yl)-29-dimetho


O

OH

OH

OM

eO

MeO

OM

e

OM

e 12

3 4

56

7

8

9

10

1112

13

14

15

161998400

2998400

3998400

4998400

5998400

6998400

7998400

8998400 9998400

10998400

11998400

[29]

Dthyrsiflorum

Bi-bicyclic

andbi-tr

icyclic

compo

unds

Denthyrsin

[3-(5101584061015840-D

imetho


dimetho

xy-2H-chrom

en-2-one

O

OO 1

23

45

678

9 10

1998400

2998400

3998400

4998400

59984006998400

7998400

8998400

9998400

H3CO

H3CO

OCH

3

OCH

3

[30]

Denthyrsin

ol(451015840-D

imetho


25410158407-tetraol

OCH

3

OCH

3

OH

OH

OH

OH

1

2

34

4a

4b

56

7

88

a

910

10a

1998400 3998400

2998400

49984004

a9984004

b998400

5998400

6998400

7998400

8998400

8a998400

9998400

10998400

10a998400

[30]


Table1Con

tinued

Species

Con

stituent

Chem

icalform

ula

Structures

ofcompo

und

Reference

Denthyrsin

one

(74101584071015840-Trih

ydroxy-22101584081015840-tr

imetho

xy-


OCH

3

O

O

OH

OH

OH

12

34

4a

4b

56

7

88

a910 10

a

1998400

2998400 3998400

49984004

a9984004

b998400

5998400

69984007998400

8998400

8a9984009998400

10998400

10a998400

H3CO

H3CO

[30]

Denthyrsin

in15

7-Trim

etho

xyph

enanthrene-26-diol

OCH

3

OH

H3CO

H3CO

HO

[30]

Scop

aron

emdash

OO

H3CO

H3CO

[30]

b-Sitoste

rol

mdash

OCH

3

OH

OH

[30]

Daucoste

rol

mdash

OCH

3

OH

OH

[30]



ABTSradicals

Hydroxylradicals

DPPHradicals






50
































1= R2=

OCH3R3= OH R

4= H (4) R

1= R2= R3= OCH

3R4= H

(5) R1= R2= OH R

3= R4= H (6) R

1= R3= OCH

3R2

= OH R4= H (7) R

1= OCH

3R2= R3= OH R

4= H (8)

R1= R3= OH R

2= R4= H (9) and R

1= R3= OH R

2=

HR4= OCH




1= R3= OH R

2= R5= OCH

3 R4= H(A)

R1= R4= R5= OH R

2= H R

3= OCH

3(B) R

1= R5=

OH R2= R3= OCH

3 R4= H(C) R

1= R2= OCH

3 R3=

R5= OH R

4= H(D) R

1= H R

2= R3= OH(E) R

1= H

R2= OH R

3= OCH

3(F) R

1= OCH

3 R2= R4= OH R

3

= R5= H(G) R

1= R3= OH R

2= OCH

3(H) R

1= R5=

OH R2= R4= H R

3= OCH

3(I) R1= R3= OCH

3 R2=

R5= OH R

4= H(J) R

1= R2= R4= OH R

3= OCH

3 R5=

H(K) R1= OCH

3 R2= R4= H R

3= R5= OH(L) and

R1= R2= R3= OH R







Dloddigesii


Dnobile










50values




Polysaccharide

HPS-IB23



OAc3 120572-D-Gal 120572-D-Gal



GM-CSFuarr












T cell B cell

D nobile


D moniliforme


































Table 7 Continued







[58]











4 Conclusion






Acknowledgments


References












































































































of






Disease Markers



OncologyJournal of





PPAR Research



Journal of

ObesityJournal of

















Table1Con

tinued

Species

Con

stituent

Chem

icalform

ula

Structures

ofcompo

und

Reference

Dendrofl

orin

R=OH

OH

OH

OR1

234

a

9a

8a

4b

45

6

9

7

8OM

e

[26]

Know

nas

oleano

licacid

andb-sitosterolcom

poun

ds

(A)D

engibsin

R=H

OH

OH

OR1

23

9a

8a

4a

4b

45

6

9

7

8OM

e

[26]

(B)C

yprip

edin

R=OMe

O

RO

HO

OM

e1

2

3

8a

4a

4b

45

6

910

10a

7

8

[26]

(C)G

igantol

(D)M

oscatilin

(E)T

ristin

R=OHR

=HR

=OMe

R=R=OMeR=OH

R=R=OHR

=H

R

OH

OM

e

R998400 R998400998400

[26]

(F)N

aringenin

(G)H

omoerio

dictyol

R=H

R=OMe

OOO

H

OH

HO

R[26]


Table1Con

tinued

Species

Con

stituent

Chem

icalform

ula

Structures

ofcompo

und

Reference

(H)M

oscatin

mdashO

H

HO

OM

e

[26]

(I)2


etho

xyph

enanthrene

mdashO

H

HO

OM

e

OM

e

MeO

[26]

(J)4

7-dihydroxy-2-metho

xy-910

-dihydroph

enanthrene

mdash

OH

HO

OM

e[26]

(K)S

coparone

(L)S

copo

letin

(M)A

yapin

R=R=OMe

R=OMeR=OH

R+R=OCH

2OO

O

R R998400[26]

Dlongicornu

Mon

oaromatic

compo

unds


Dibutylph

thalate

CH2C

H(C

2H5)(C

H2)

3CH

3(C

H2)

3CH

3

O O

OR

OR

[27]

Ethylh

aematom

mate

C 11H

12O

5

HO

CHO

OH

COO

C 2H5

CH3

[27]


Table1Con

tinued

Species

Con

stituent

Chem

icalform

ula

Structures

ofcompo

und

Reference

MethylB

-orcinolcarboxylate

C 10H

12O

4

HO

OH

CH3

H3C

COO

CH3

[27]

N-D

ocosyltra

ns-fe

rulate

Ferulaldehyde

R=CO

OCH

2(CH

2)20CH

3R=CH

O

R

HH

OH

OCH

3

[27]

Dn

obile

Sesquiterpenes

(Dendron

obilins

A)

Cop

acam

phane-type

(1R2R

4S5S6S8S9R)-28-

Dihydroxycopacamph

an-15-on

eH H

H

H

H

O

HO

OH

(R)

11 109

7

15

1214

13

16 5

(R) (R)

(S)

(S)

(S)

(S)

[28]

Picrotoxane-type


-3(15)-lacton

e

H

H H

H

H

O O

HO

OH

OH

1214

15

133

11

110

9

6[28]


Table1Con

tinued

Species

Con

stituent

Chem

icalform

ula

Structures

ofcompo

und

Reference

Picrotoxane-type

(2b3b5b9a11b)-211-Epo

xy-91113


cton

e

H

HHH

H H

OO O

HO H

O

OH

123

14

15

56

9 1

11 10 13

[28]

Picrotoxane-type

(2b3b5b12Rlowast

)-21113

-Trih

ydroxy-


e

H

HHH

H H

O O

HO H

O

OH

1214

15

567

91

11

10 13(R

lowast)

[28]

Picrotoxane-type


-Trih

ydroxy-


eO O

H HH

HH

H

HO H

O

OH

1215569

110

11

7

1314

(Slowast

)

[28]


Table1Con

tinued

Species

Con

stituent

Chem

icalform

ula

Structures

ofcompo

und

Reference

Picrotoxane-type

(2b3b5b9a)-10

-Cyclo-21113

-trihydroxy-


eO O

H HH

H H HO

HO

OH

121556

9 110

11

7

1314

[28]

Muu

rolene-ty

pe(9b10a)-M

uurol-4

-ene-910

11-tr

iol

H

HHH

HO

OH

OH

12

15 69

110

11

4

2

1314

[28]

Allo

arom

adendrene-type

(10a)-A

lloarom

adendrene-1012

14-tr

iol

H

H

HH

H

HO

OH

OH 12

15

6

91

10

1142

1314

5[28]

Cyclo

copacamph

ane-type

(5b)-C

yclocopacamph

ane-51215

-triol

H

1

14

10

7 24

35

6

1512

1311 H

HH

H

H

HO

OH

OH

[28]


ble1Con

tinued

Species

Con

stituent

Chem

icalform

ula

Structures

ofcompo

und

Reference

Bibenzylderiv

atives

Dendron

opheno

lA221015840991015840-Tetrametho

xy131015840141015840-peroxy-111015840-


OO

MeO

MeO

OM

e

OM

eHO

OH

12

3 4

56

7

8

9

10

1112

13

14

15

161998400

2998400

3998400

4998400

5998400

6998400

7998400

8998400

9998400

10998400

11998400

12998400

13998400

14998400

15998400

16998400

[29]

Dendron

opheno

lB1-(2101584061015840-D

imetho


prop

yl)-29-dimetho


O

OH

OH

OM

eO

MeO

OM

e

OM

e 12

3 4

56

7

8

9

10

1112

13

14

15

161998400

2998400

3998400

4998400

5998400

6998400

7998400

8998400 9998400

10998400

11998400

[29]

Dthyrsiflorum

Bi-bicyclic

andbi-tr

icyclic

compo

unds

Denthyrsin

[3-(5101584061015840-D

imetho


dimetho

xy-2H-chrom

en-2-one

O

OO 1

23

45

678

9 10

1998400

2998400

3998400

4998400

59984006998400

7998400

8998400

9998400

H3CO

H3CO

OCH

3

OCH

3

[30]

Denthyrsin

ol(451015840-D

imetho


25410158407-tetraol

OCH

3

OCH

3

OH

OH

OH

OH

1

2

34

4a

4b

56

7

88

a

910

10a

1998400 3998400

2998400

49984004

a9984004

b998400

5998400

6998400

7998400

8998400

8a998400

9998400

10998400

10a998400

[30]


Table1Con

tinued

Species

Con

stituent

Chem

icalform

ula

Structures

ofcompo

und

Reference

Denthyrsin

one

(74101584071015840-Trih

ydroxy-22101584081015840-tr

imetho

xy-


OCH

3

O

O

OH

OH

OH

12

34

4a

4b

56

7

88

a910 10

a

1998400

2998400 3998400

49984004

a9984004

b998400

5998400

69984007998400

8998400

8a9984009998400

10998400

10a998400

H3CO

H3CO

[30]

Denthyrsin

in15

7-Trim

etho

xyph

enanthrene-26-diol

OCH

3

OH

H3CO

H3CO

HO

[30]

Scop

aron

emdash

OO

H3CO

H3CO

[30]

b-Sitoste

rol

mdash

OCH

3

OH

OH

[30]

Daucoste

rol

mdash

OCH

3

OH

OH

[30]



ABTSradicals

Hydroxylradicals

DPPHradicals






50
































1= R2=

OCH3R3= OH R

4= H (4) R

1= R2= R3= OCH

3R4= H

(5) R1= R2= OH R

3= R4= H (6) R

1= R3= OCH

3R2

= OH R4= H (7) R

1= OCH

3R2= R3= OH R

4= H (8)

R1= R3= OH R

2= R4= H (9) and R

1= R3= OH R

2=

HR4= OCH




1= R3= OH R

2= R5= OCH

3 R4= H(A)

R1= R4= R5= OH R

2= H R

3= OCH

3(B) R

1= R5=

OH R2= R3= OCH

3 R4= H(C) R

1= R2= OCH

3 R3=

R5= OH R

4= H(D) R

1= H R

2= R3= OH(E) R

1= H

R2= OH R

3= OCH

3(F) R

1= OCH

3 R2= R4= OH R

3

= R5= H(G) R

1= R3= OH R

2= OCH

3(H) R

1= R5=

OH R2= R4= H R

3= OCH

3(I) R1= R3= OCH

3 R2=

R5= OH R

4= H(J) R

1= R2= R4= OH R

3= OCH

3 R5=

H(K) R1= OCH

3 R2= R4= H R

3= R5= OH(L) and

R1= R2= R3= OH R







Dloddigesii


Dnobile










50values




Polysaccharide

HPS-IB23



OAc3 120572-D-Gal 120572-D-Gal



GM-CSFuarr












T cell B cell

D nobile


D moniliforme


































Table 7 Continued







[58]











4 Conclusion






Acknowledgments


References












































































































of






Disease Markers



OncologyJournal of





PPAR Research



Journal of

ObesityJournal of

















Table1Con

tinued

Species

Con

stituent

Chem

icalform

ula

Structures

ofcompo

und

Reference

(H)M

oscatin

mdashO

H

HO

OM

e

[26]

(I)2


etho

xyph

enanthrene

mdashO

H

HO

OM

e

OM

e

MeO

[26]

(J)4

7-dihydroxy-2-metho

xy-910

-dihydroph

enanthrene

mdash

OH

HO

OM

e[26]

(K)S

coparone

(L)S

copo

letin

(M)A

yapin

R=R=OMe

R=OMeR=OH

R+R=OCH

2OO

O

R R998400[26]

Dlongicornu

Mon

oaromatic

compo

unds


Dibutylph

thalate

CH2C

H(C

2H5)(C

H2)

3CH

3(C

H2)

3CH

3

O O

OR

OR

[27]

Ethylh

aematom

mate

C 11H

12O

5

HO

CHO

OH

COO

C 2H5

CH3

[27]


Table1Con

tinued

Species

Con

stituent

Chem

icalform

ula

Structures

ofcompo

und

Reference

MethylB

-orcinolcarboxylate

C 10H

12O

4

HO

OH

CH3

H3C

COO

CH3

[27]

N-D

ocosyltra

ns-fe

rulate

Ferulaldehyde

R=CO

OCH

2(CH

2)20CH

3R=CH

O

R

HH

OH

OCH

3

[27]

Dn

obile

Sesquiterpenes

(Dendron

obilins

A)

Cop

acam

phane-type

(1R2R

4S5S6S8S9R)-28-

Dihydroxycopacamph

an-15-on

eH H

H

H

H

O

HO

OH

(R)

11 109

7

15

1214

13

16 5

(R) (R)

(S)

(S)

(S)

(S)

[28]

Picrotoxane-type


-3(15)-lacton

e

H

H H

H

H

O O

HO

OH

OH

1214

15

133

11

110

9

6[28]


Table1Con

tinued

Species

Con

stituent

Chem

icalform

ula

Structures

ofcompo

und

Reference

Picrotoxane-type

(2b3b5b9a11b)-211-Epo

xy-91113


cton

e

H

HHH

H H

OO O

HO H

O

OH

123

14

15

56

9 1

11 10 13

[28]

Picrotoxane-type

(2b3b5b12Rlowast

)-21113

-Trih

ydroxy-


e

H

HHH

H H

O O

HO H

O

OH

1214

15

567

91

11

10 13(R

lowast)

[28]

Picrotoxane-type


-Trih

ydroxy-


eO O

H HH

HH

H

HO H

O

OH

1215569

110

11

7

1314

(Slowast

)

[28]


Table1Con

tinued

Species

Con

stituent

Chem

icalform

ula

Structures

ofcompo

und

Reference

Picrotoxane-type

(2b3b5b9a)-10

-Cyclo-21113

-trihydroxy-


eO O

H HH

H H HO

HO

OH

121556

9 110

11

7

1314

[28]

Muu

rolene-ty

pe(9b10a)-M

uurol-4

-ene-910

11-tr

iol

H

HHH

HO

OH

OH

12

15 69

110

11

4

2

1314

[28]

Allo

arom

adendrene-type

(10a)-A

lloarom

adendrene-1012

14-tr

iol

H

H

HH

H

HO

OH

OH 12

15

6

91

10

1142

1314

5[28]

Cyclo

copacamph

ane-type

(5b)-C

yclocopacamph

ane-51215

-triol

H

1

14

10

7 24

35

6

1512

1311 H

HH

H

H

HO

OH

OH

[28]


ble1Con

tinued

Species

Con

stituent

Chem

icalform

ula

Structures

ofcompo

und

Reference

Bibenzylderiv

atives

Dendron

opheno

lA221015840991015840-Tetrametho

xy131015840141015840-peroxy-111015840-


OO

MeO

MeO

OM

e

OM

eHO

OH

12

3 4

56

7

8

9

10

1112

13

14

15

161998400

2998400

3998400

4998400

5998400

6998400

7998400

8998400

9998400

10998400

11998400

12998400

13998400

14998400

15998400

16998400

[29]

Dendron

opheno

lB1-(2101584061015840-D

imetho


prop

yl)-29-dimetho


O

OH

OH

OM

eO

MeO

OM

e

OM

e 12

3 4

56

7

8

9

10

1112

13

14

15

161998400

2998400

3998400

4998400

5998400

6998400

7998400

8998400 9998400

10998400

11998400

[29]

Dthyrsiflorum

Bi-bicyclic

andbi-tr

icyclic

compo

unds

Denthyrsin

[3-(5101584061015840-D

imetho


dimetho

xy-2H-chrom

en-2-one

O

OO 1

23

45

678

9 10

1998400

2998400

3998400

4998400

59984006998400

7998400

8998400

9998400

H3CO

H3CO

OCH

3

OCH

3

[30]

Denthyrsin

ol(451015840-D

imetho


25410158407-tetraol

OCH

3

OCH

3

OH

OH

OH

OH

1

2

34

4a

4b

56

7

88

a

910

10a

1998400 3998400

2998400

49984004

a9984004

b998400

5998400

6998400

7998400

8998400

8a998400

9998400

10998400

10a998400

[30]


Table1Con

tinued

Species

Con

stituent

Chem

icalform

ula

Structures

ofcompo

und

Reference

Denthyrsin

one

(74101584071015840-Trih

ydroxy-22101584081015840-tr

imetho

xy-


OCH

3

O

O

OH

OH

OH

12

34

4a

4b

56

7

88

a910 10

a

1998400

2998400 3998400

49984004

a9984004

b998400

5998400

69984007998400

8998400

8a9984009998400

10998400

10a998400

H3CO

H3CO

[30]

Denthyrsin

in15

7-Trim

etho

xyph

enanthrene-26-diol

OCH

3

OH

H3CO

H3CO

HO

[30]

Scop

aron

emdash

OO

H3CO

H3CO

[30]

b-Sitoste

rol

mdash

OCH

3

OH

OH

[30]

Daucoste

rol

mdash

OCH

3

OH

OH

[30]



ABTSradicals

Hydroxylradicals

DPPHradicals






50
































1= R2=

OCH3R3= OH R

4= H (4) R

1= R2= R3= OCH

3R4= H

(5) R1= R2= OH R

3= R4= H (6) R

1= R3= OCH

3R2

= OH R4= H (7) R

1= OCH

3R2= R3= OH R

4= H (8)

R1= R3= OH R

2= R4= H (9) and R

1= R3= OH R

2=

HR4= OCH




1= R3= OH R

2= R5= OCH

3 R4= H(A)

R1= R4= R5= OH R

2= H R

3= OCH

3(B) R

1= R5=

OH R2= R3= OCH

3 R4= H(C) R

1= R2= OCH

3 R3=

R5= OH R

4= H(D) R

1= H R

2= R3= OH(E) R

1= H

R2= OH R

3= OCH

3(F) R

1= OCH

3 R2= R4= OH R

3

= R5= H(G) R

1= R3= OH R

2= OCH

3(H) R

1= R5=

OH R2= R4= H R

3= OCH

3(I) R1= R3= OCH

3 R2=

R5= OH R

4= H(J) R

1= R2= R4= OH R

3= OCH

3 R5=

H(K) R1= OCH

3 R2= R4= H R

3= R5= OH(L) and

R1= R2= R3= OH R







Dloddigesii


Dnobile










50values




Polysaccharide

HPS-IB23



OAc3 120572-D-Gal 120572-D-Gal



GM-CSFuarr












T cell B cell

D nobile


D moniliforme


































Table 7 Continued







[58]











4 Conclusion






Acknowledgments


References












































































































of






Disease Markers



OncologyJournal of





PPAR Research



Journal of

ObesityJournal of

















Table1Con

tinued

Species

Con

stituent

Chem

icalform

ula

Structures

ofcompo

und

Reference

MethylB

-orcinolcarboxylate

C 10H

12O

4

HO

OH

CH3

H3C

COO

CH3

[27]

N-D

ocosyltra

ns-fe

rulate

Ferulaldehyde

R=CO

OCH

2(CH

2)20CH

3R=CH

O

R

HH

OH

OCH

3

[27]

Dn

obile

Sesquiterpenes

(Dendron

obilins

A)

Cop

acam

phane-type

(1R2R

4S5S6S8S9R)-28-

Dihydroxycopacamph

an-15-on

eH H

H

H

H

O

HO

OH

(R)

11 109

7

15

1214

13

16 5

(R) (R)

(S)

(S)

(S)

(S)

[28]

Picrotoxane-type


-3(15)-lacton

e

H

H H

H

H

O O

HO

OH

OH

1214

15

133

11

110

9

6[28]


Table1Con

tinued

Species

Con

stituent

Chem

icalform

ula

Structures

ofcompo

und

Reference

Picrotoxane-type

(2b3b5b9a11b)-211-Epo

xy-91113


cton

e

H

HHH

H H

OO O

HO H

O

OH

123

14

15

56

9 1

11 10 13

[28]

Picrotoxane-type

(2b3b5b12Rlowast

)-21113

-Trih

ydroxy-


e

H

HHH

H H

O O

HO H

O

OH

1214

15

567

91

11

10 13(R

lowast)

[28]

Picrotoxane-type


-Trih

ydroxy-


eO O

H HH

HH

H

HO H

O

OH

1215569

110

11

7

1314

(Slowast

)

[28]


Table1Con

tinued

Species

Con

stituent

Chem

icalform

ula

Structures

ofcompo

und

Reference

Picrotoxane-type

(2b3b5b9a)-10

-Cyclo-21113

-trihydroxy-


eO O

H HH

H H HO

HO

OH

121556

9 110

11

7

1314

[28]

Muu

rolene-ty

pe(9b10a)-M

uurol-4

-ene-910

11-tr

iol

H

HHH

HO

OH

OH

12

15 69

110

11

4

2

1314

[28]

Allo

arom

adendrene-type

(10a)-A

lloarom

adendrene-1012

14-tr

iol

H

H

HH

H

HO

OH

OH 12

15

6

91

10

1142

1314

5[28]

Cyclo

copacamph

ane-type

(5b)-C

yclocopacamph

ane-51215

-triol

H

1

14

10

7 24

35

6

1512

1311 H

HH

H

H

HO

OH

OH

[28]


ble1Con

tinued

Species

Con

stituent

Chem

icalform

ula

Structures

ofcompo

und

Reference

Bibenzylderiv

atives

Dendron

opheno

lA221015840991015840-Tetrametho

xy131015840141015840-peroxy-111015840-


OO

MeO

MeO

OM

e

OM

eHO

OH

12

3 4

56

7

8

9

10

1112

13

14

15

161998400

2998400

3998400

4998400

5998400

6998400

7998400

8998400

9998400

10998400

11998400

12998400

13998400

14998400

15998400

16998400

[29]

Dendron

opheno

lB1-(2101584061015840-D

imetho


prop

yl)-29-dimetho


O

OH

OH

OM

eO

MeO

OM

e

OM

e 12

3 4

56

7

8

9

10

1112

13

14

15

161998400

2998400

3998400

4998400

5998400

6998400

7998400

8998400 9998400

10998400

11998400

[29]

Dthyrsiflorum

Bi-bicyclic

andbi-tr

icyclic

compo

unds

Denthyrsin

[3-(5101584061015840-D

imetho


dimetho

xy-2H-chrom

en-2-one

O

OO 1

23

45

678

9 10

1998400

2998400

3998400

4998400

59984006998400

7998400

8998400

9998400

H3CO

H3CO

OCH

3

OCH

3

[30]

Denthyrsin

ol(451015840-D

imetho


25410158407-tetraol

OCH

3

OCH

3

OH

OH

OH

OH

1

2

34

4a

4b

56

7

88

a

910

10a

1998400 3998400

2998400

49984004

a9984004

b998400

5998400

6998400

7998400

8998400

8a998400

9998400

10998400

10a998400

[30]


Table1Con

tinued

Species

Con

stituent

Chem

icalform

ula

Structures

ofcompo

und

Reference

Denthyrsin

one

(74101584071015840-Trih

ydroxy-22101584081015840-tr

imetho

xy-


OCH

3

O

O

OH

OH

OH

12

34

4a

4b

56

7

88

a910 10

a

1998400

2998400 3998400

49984004

a9984004

b998400

5998400

69984007998400

8998400

8a9984009998400

10998400

10a998400

H3CO

H3CO

[30]

Denthyrsin

in15

7-Trim

etho

xyph

enanthrene-26-diol

OCH

3

OH

H3CO

H3CO

HO

[30]

Scop

aron

emdash

OO

H3CO

H3CO

[30]

b-Sitoste

rol

mdash

OCH

3

OH

OH

[30]

Daucoste

rol

mdash

OCH

3

OH

OH

[30]



ABTSradicals

Hydroxylradicals

DPPHradicals






50
































1= R2=

OCH3R3= OH R

4= H (4) R

1= R2= R3= OCH

3R4= H

(5) R1= R2= OH R

3= R4= H (6) R

1= R3= OCH

3R2

= OH R4= H (7) R

1= OCH

3R2= R3= OH R

4= H (8)

R1= R3= OH R

2= R4= H (9) and R

1= R3= OH R

2=

HR4= OCH




1= R3= OH R

2= R5= OCH

3 R4= H(A)

R1= R4= R5= OH R

2= H R

3= OCH

3(B) R

1= R5=

OH R2= R3= OCH

3 R4= H(C) R

1= R2= OCH

3 R3=

R5= OH R

4= H(D) R

1= H R

2= R3= OH(E) R

1= H

R2= OH R

3= OCH

3(F) R

1= OCH

3 R2= R4= OH R

3

= R5= H(G) R

1= R3= OH R

2= OCH

3(H) R

1= R5=

OH R2= R4= H R

3= OCH

3(I) R1= R3= OCH

3 R2=

R5= OH R

4= H(J) R

1= R2= R4= OH R

3= OCH

3 R5=

H(K) R1= OCH

3 R2= R4= H R

3= R5= OH(L) and

R1= R2= R3= OH R







Dloddigesii


Dnobile










50values




Polysaccharide

HPS-IB23



OAc3 120572-D-Gal 120572-D-Gal



GM-CSFuarr












T cell B cell

D nobile


D moniliforme


































Table 7 Continued







[58]











4 Conclusion






Acknowledgments


References












































































































of






Disease Markers



OncologyJournal of





PPAR Research



Journal of

ObesityJournal of

















Table1Con

tinued

Species

Con

stituent

Chem

icalform

ula

Structures

ofcompo

und

Reference

Picrotoxane-type

(2b3b5b9a11b)-211-Epo

xy-91113


cton

e

H

HHH

H H

OO O

HO H

O

OH

123

14

15

56

9 1

11 10 13

[28]

Picrotoxane-type

(2b3b5b12Rlowast

)-21113

-Trih

ydroxy-


e

H

HHH

H H

O O

HO H

O

OH

1214

15

567

91

11

10 13(R

lowast)

[28]

Picrotoxane-type


-Trih

ydroxy-


eO O

H HH

HH

H

HO H

O

OH

1215569

110

11

7

1314

(Slowast

)

[28]


Table1Con

tinued

Species

Con

stituent

Chem

icalform

ula

Structures

ofcompo

und

Reference

Picrotoxane-type

(2b3b5b9a)-10

-Cyclo-21113

-trihydroxy-


eO O

H HH

H H HO

HO

OH

121556

9 110

11

7

1314

[28]

Muu

rolene-ty

pe(9b10a)-M

uurol-4

-ene-910

11-tr

iol

H

HHH

HO

OH

OH

12

15 69

110

11

4

2

1314

[28]

Allo

arom

adendrene-type

(10a)-A

lloarom

adendrene-1012

14-tr

iol

H

H

HH

H

HO

OH

OH 12

15

6

91

10

1142

1314

5[28]

Cyclo

copacamph

ane-type

(5b)-C

yclocopacamph

ane-51215

-triol

H

1

14

10

7 24

35

6

1512

1311 H

HH

H

H

HO

OH

OH

[28]


ble1Con

tinued

Species

Con

stituent

Chem

icalform

ula

Structures

ofcompo

und

Reference

Bibenzylderiv

atives

Dendron

opheno

lA221015840991015840-Tetrametho

xy131015840141015840-peroxy-111015840-


OO

MeO

MeO

OM

e

OM

eHO

OH

12

3 4

56

7

8

9

10

1112

13

14

15

161998400

2998400

3998400

4998400

5998400

6998400

7998400

8998400

9998400

10998400

11998400

12998400

13998400

14998400

15998400

16998400

[29]

Dendron

opheno

lB1-(2101584061015840-D

imetho


prop

yl)-29-dimetho


O

OH

OH

OM

eO

MeO

OM

e

OM

e 12

3 4

56

7

8

9

10

1112

13

14

15

161998400

2998400

3998400

4998400

5998400

6998400

7998400

8998400 9998400

10998400

11998400

[29]

Dthyrsiflorum

Bi-bicyclic

andbi-tr

icyclic

compo

unds

Denthyrsin

[3-(5101584061015840-D

imetho


dimetho

xy-2H-chrom

en-2-one

O

OO 1

23

45

678

9 10

1998400

2998400

3998400

4998400

59984006998400

7998400

8998400

9998400

H3CO

H3CO

OCH

3

OCH

3

[30]

Denthyrsin

ol(451015840-D

imetho


25410158407-tetraol

OCH

3

OCH

3

OH

OH

OH

OH

1

2

34

4a

4b

56

7

88

a

910

10a

1998400 3998400

2998400

49984004

a9984004

b998400

5998400

6998400

7998400

8998400

8a998400

9998400

10998400

10a998400

[30]


Table1Con

tinued

Species

Con

stituent

Chem

icalform

ula

Structures

ofcompo

und

Reference

Denthyrsin

one

(74101584071015840-Trih

ydroxy-22101584081015840-tr

imetho

xy-


OCH

3

O

O

OH

OH

OH

12

34

4a

4b

56

7

88

a910 10

a

1998400

2998400 3998400

49984004

a9984004

b998400

5998400

69984007998400

8998400

8a9984009998400

10998400

10a998400

H3CO

H3CO

[30]

Denthyrsin

in15

7-Trim

etho

xyph

enanthrene-26-diol

OCH

3

OH

H3CO

H3CO

HO

[30]

Scop

aron

emdash

OO

H3CO

H3CO

[30]

b-Sitoste

rol

mdash

OCH

3

OH

OH

[30]

Daucoste

rol

mdash

OCH

3

OH

OH

[30]



ABTSradicals

Hydroxylradicals

DPPHradicals






50
































1= R2=

OCH3R3= OH R

4= H (4) R

1= R2= R3= OCH

3R4= H

(5) R1= R2= OH R

3= R4= H (6) R

1= R3= OCH

3R2

= OH R4= H (7) R

1= OCH

3R2= R3= OH R

4= H (8)

R1= R3= OH R

2= R4= H (9) and R

1= R3= OH R

2=

HR4= OCH




1= R3= OH R

2= R5= OCH

3 R4= H(A)

R1= R4= R5= OH R

2= H R

3= OCH

3(B) R

1= R5=

OH R2= R3= OCH

3 R4= H(C) R

1= R2= OCH

3 R3=

R5= OH R

4= H(D) R

1= H R

2= R3= OH(E) R

1= H

R2= OH R

3= OCH

3(F) R

1= OCH

3 R2= R4= OH R

3

= R5= H(G) R

1= R3= OH R

2= OCH

3(H) R

1= R5=

OH R2= R4= H R

3= OCH

3(I) R1= R3= OCH

3 R2=

R5= OH R

4= H(J) R

1= R2= R4= OH R

3= OCH

3 R5=

H(K) R1= OCH

3 R2= R4= H R

3= R5= OH(L) and

R1= R2= R3= OH R







Dloddigesii


Dnobile










50values




Polysaccharide

HPS-IB23



OAc3 120572-D-Gal 120572-D-Gal



GM-CSFuarr












T cell B cell

D nobile


D moniliforme


































Table 7 Continued







[58]











4 Conclusion






Acknowledgments


References












































































































of






Disease Markers



OncologyJournal of





PPAR Research



Journal of

ObesityJournal of

















Table1Con

tinued

Species

Con

stituent

Chem

icalform

ula

Structures

ofcompo

und

Reference

Picrotoxane-type

(2b3b5b9a)-10

-Cyclo-21113

-trihydroxy-


eO O

H HH

H H HO

HO

OH

121556

9 110

11

7

1314

[28]

Muu

rolene-ty

pe(9b10a)-M

uurol-4

-ene-910

11-tr

iol

H

HHH

HO

OH

OH

12

15 69

110

11

4

2

1314

[28]

Allo

arom

adendrene-type

(10a)-A

lloarom

adendrene-1012

14-tr

iol

H

H

HH

H

HO

OH

OH 12

15

6

91

10

1142

1314

5[28]

Cyclo

copacamph

ane-type

(5b)-C

yclocopacamph

ane-51215

-triol

H

1

14

10

7 24

35

6

1512

1311 H

HH

H

H

HO

OH

OH

[28]


ble1Con

tinued

Species

Con

stituent

Chem

icalform

ula

Structures

ofcompo

und

Reference

Bibenzylderiv

atives

Dendron

opheno

lA221015840991015840-Tetrametho

xy131015840141015840-peroxy-111015840-


OO

MeO

MeO

OM

e

OM

eHO

OH

12

3 4

56

7

8

9

10

1112

13

14

15

161998400

2998400

3998400

4998400

5998400

6998400

7998400

8998400

9998400

10998400

11998400

12998400

13998400

14998400

15998400

16998400

[29]

Dendron

opheno

lB1-(2101584061015840-D

imetho


prop

yl)-29-dimetho


O

OH

OH

OM

eO

MeO

OM

e

OM

e 12

3 4

56

7

8

9

10

1112

13

14

15

161998400

2998400

3998400

4998400

5998400

6998400

7998400

8998400 9998400

10998400

11998400

[29]

Dthyrsiflorum

Bi-bicyclic

andbi-tr

icyclic

compo

unds

Denthyrsin

[3-(5101584061015840-D

imetho


dimetho

xy-2H-chrom

en-2-one

O

OO 1

23

45

678

9 10

1998400

2998400

3998400

4998400

59984006998400

7998400

8998400

9998400

H3CO

H3CO

OCH

3

OCH

3

[30]

Denthyrsin

ol(451015840-D

imetho


25410158407-tetraol

OCH

3

OCH

3

OH

OH

OH

OH

1

2

34

4a

4b

56

7

88

a

910

10a

1998400 3998400

2998400

49984004

a9984004

b998400

5998400

6998400

7998400

8998400

8a998400

9998400

10998400

10a998400

[30]


Table1Con

tinued

Species

Con

stituent

Chem

icalform

ula

Structures

ofcompo

und

Reference

Denthyrsin

one

(74101584071015840-Trih

ydroxy-22101584081015840-tr

imetho

xy-


OCH

3

O

O

OH

OH

OH

12

34

4a

4b

56

7

88

a910 10

a

1998400

2998400 3998400

49984004

a9984004

b998400

5998400

69984007998400

8998400

8a9984009998400

10998400

10a998400

H3CO

H3CO

[30]

Denthyrsin

in15

7-Trim

etho

xyph

enanthrene-26-diol

OCH

3

OH

H3CO

H3CO

HO

[30]

Scop

aron

emdash

OO

H3CO

H3CO

[30]

b-Sitoste

rol

mdash

OCH

3

OH

OH

[30]

Daucoste

rol

mdash

OCH

3

OH

OH

[30]



ABTSradicals

Hydroxylradicals

DPPHradicals






50
































1= R2=

OCH3R3= OH R

4= H (4) R

1= R2= R3= OCH

3R4= H

(5) R1= R2= OH R

3= R4= H (6) R

1= R3= OCH

3R2

= OH R4= H (7) R

1= OCH

3R2= R3= OH R

4= H (8)

R1= R3= OH R

2= R4= H (9) and R

1= R3= OH R

2=

HR4= OCH




1= R3= OH R

2= R5= OCH

3 R4= H(A)

R1= R4= R5= OH R

2= H R

3= OCH

3(B) R

1= R5=

OH R2= R3= OCH

3 R4= H(C) R

1= R2= OCH

3 R3=

R5= OH R

4= H(D) R

1= H R

2= R3= OH(E) R

1= H

R2= OH R

3= OCH

3(F) R

1= OCH

3 R2= R4= OH R

3

= R5= H(G) R

1= R3= OH R

2= OCH

3(H) R

1= R5=

OH R2= R4= H R

3= OCH

3(I) R1= R3= OCH

3 R2=

R5= OH R

4= H(J) R

1= R2= R4= OH R

3= OCH

3 R5=

H(K) R1= OCH

3 R2= R4= H R

3= R5= OH(L) and

R1= R2= R3= OH R







Dloddigesii


Dnobile










50values




Polysaccharide

HPS-IB23



OAc3 120572-D-Gal 120572-D-Gal



GM-CSFuarr












T cell B cell

D nobile


D moniliforme


































Table 7 Continued







[58]











4 Conclusion






Acknowledgments


References












































































































of






Disease Markers



OncologyJournal of





PPAR Research



Journal of

ObesityJournal of

















ble1Con

tinued

Species

Con

stituent

Chem

icalform

ula

Structures

ofcompo

und

Reference

Bibenzylderiv

atives

Dendron

opheno

lA221015840991015840-Tetrametho

xy131015840141015840-peroxy-111015840-


OO

MeO

MeO

OM

e

OM

eHO

OH

12

3 4

56

7

8

9

10

1112

13

14

15

161998400

2998400

3998400

4998400

5998400

6998400

7998400

8998400

9998400

10998400

11998400

12998400

13998400

14998400

15998400

16998400

[29]

Dendron

opheno

lB1-(2101584061015840-D

imetho


prop

yl)-29-dimetho


O

OH

OH

OM

eO

MeO

OM

e

OM

e 12

3 4

56

7

8

9

10

1112

13

14

15

161998400

2998400

3998400

4998400

5998400

6998400

7998400

8998400 9998400

10998400

11998400

[29]

Dthyrsiflorum

Bi-bicyclic

andbi-tr

icyclic

compo

unds

Denthyrsin

[3-(5101584061015840-D

imetho


dimetho

xy-2H-chrom

en-2-one

O

OO 1

23

45

678

9 10

1998400

2998400

3998400

4998400

59984006998400

7998400

8998400

9998400

H3CO

H3CO

OCH

3

OCH

3

[30]

Denthyrsin

ol(451015840-D

imetho


25410158407-tetraol

OCH

3

OCH

3

OH

OH

OH

OH

1

2

34

4a

4b

56

7

88

a

910

10a

1998400 3998400

2998400

49984004

a9984004

b998400

5998400

6998400

7998400

8998400

8a998400

9998400

10998400

10a998400

[30]


Table1Con

tinued

Species

Con

stituent

Chem

icalform

ula

Structures

ofcompo

und

Reference

Denthyrsin

one

(74101584071015840-Trih

ydroxy-22101584081015840-tr

imetho

xy-


OCH

3

O

O

OH

OH

OH

12

34

4a

4b

56

7

88

a910 10

a

1998400

2998400 3998400

49984004

a9984004

b998400

5998400

69984007998400

8998400

8a9984009998400

10998400

10a998400

H3CO

H3CO

[30]

Denthyrsin

in15

7-Trim

etho

xyph

enanthrene-26-diol

OCH

3

OH

H3CO

H3CO

HO

[30]

Scop

aron

emdash

OO

H3CO

H3CO

[30]

b-Sitoste

rol

mdash

OCH

3

OH

OH

[30]

Daucoste

rol

mdash

OCH

3

OH

OH

[30]



ABTSradicals

Hydroxylradicals

DPPHradicals






50
































1= R2=

OCH3R3= OH R

4= H (4) R

1= R2= R3= OCH

3R4= H

(5) R1= R2= OH R

3= R4= H (6) R

1= R3= OCH

3R2

= OH R4= H (7) R

1= OCH

3R2= R3= OH R

4= H (8)

R1= R3= OH R

2= R4= H (9) and R

1= R3= OH R

2=

HR4= OCH




1= R3= OH R

2= R5= OCH

3 R4= H(A)

R1= R4= R5= OH R

2= H R

3= OCH

3(B) R

1= R5=

OH R2= R3= OCH

3 R4= H(C) R

1= R2= OCH

3 R3=

R5= OH R

4= H(D) R

1= H R

2= R3= OH(E) R

1= H

R2= OH R

3= OCH

3(F) R

1= OCH

3 R2= R4= OH R

3

= R5= H(G) R

1= R3= OH R

2= OCH

3(H) R

1= R5=

OH R2= R4= H R

3= OCH

3(I) R1= R3= OCH

3 R2=

R5= OH R

4= H(J) R

1= R2= R4= OH R

3= OCH

3 R5=

H(K) R1= OCH

3 R2= R4= H R

3= R5= OH(L) and

R1= R2= R3= OH R







Dloddigesii


Dnobile










50values




Polysaccharide

HPS-IB23



OAc3 120572-D-Gal 120572-D-Gal



GM-CSFuarr












T cell B cell

D nobile


D moniliforme


































Table 7 Continued







[58]











4 Conclusion






Acknowledgments


References












































































































of






Disease Markers



OncologyJournal of





PPAR Research



Journal of

ObesityJournal of

















Table1Con

tinued

Species

Con

stituent

Chem

icalform

ula

Structures

ofcompo

und

Reference

Denthyrsin

one

(74101584071015840-Trih

ydroxy-22101584081015840-tr

imetho

xy-


OCH

3

O

O

OH

OH

OH

12

34

4a

4b

56

7

88

a910 10

a

1998400

2998400 3998400

49984004

a9984004

b998400

5998400

69984007998400

8998400

8a9984009998400

10998400

10a998400

H3CO

H3CO

[30]

Denthyrsin

in15

7-Trim

etho

xyph

enanthrene-26-diol

OCH

3

OH

H3CO

H3CO

HO

[30]

Scop

aron

emdash

OO

H3CO

H3CO

[30]

b-Sitoste

rol

mdash

OCH

3

OH

OH

[30]

Daucoste

rol

mdash

OCH

3

OH

OH

[30]



ABTSradicals

Hydroxylradicals

DPPHradicals






50
































1= R2=

OCH3R3= OH R

4= H (4) R

1= R2= R3= OCH

3R4= H

(5) R1= R2= OH R

3= R4= H (6) R

1= R3= OCH

3R2

= OH R4= H (7) R

1= OCH

3R2= R3= OH R

4= H (8)

R1= R3= OH R

2= R4= H (9) and R

1= R3= OH R

2=

HR4= OCH




1= R3= OH R

2= R5= OCH

3 R4= H(A)

R1= R4= R5= OH R

2= H R

3= OCH

3(B) R

1= R5=

OH R2= R3= OCH

3 R4= H(C) R

1= R2= OCH

3 R3=

R5= OH R

4= H(D) R

1= H R

2= R3= OH(E) R

1= H

R2= OH R

3= OCH

3(F) R

1= OCH

3 R2= R4= OH R

3

= R5= H(G) R

1= R3= OH R

2= OCH

3(H) R

1= R5=

OH R2= R4= H R

3= OCH

3(I) R1= R3= OCH

3 R2=

R5= OH R

4= H(J) R

1= R2= R4= OH R

3= OCH

3 R5=

H(K) R1= OCH

3 R2= R4= H R

3= R5= OH(L) and

R1= R2= R3= OH R







Dloddigesii


Dnobile










50values




Polysaccharide

HPS-IB23



OAc3 120572-D-Gal 120572-D-Gal



GM-CSFuarr












T cell B cell

D nobile


D moniliforme


































Table 7 Continued







[58]











4 Conclusion






Acknowledgments


References












































































































of






Disease Markers



OncologyJournal of





PPAR Research



Journal of

ObesityJournal of


















ABTSradicals

Hydroxylradicals

DPPHradicals






50
































1= R2=

OCH3R3= OH R

4= H (4) R

1= R2= R3= OCH

3R4= H

(5) R1= R2= OH R

3= R4= H (6) R

1= R3= OCH

3R2

= OH R4= H (7) R

1= OCH

3R2= R3= OH R

4= H (8)

R1= R3= OH R

2= R4= H (9) and R

1= R3= OH R

2=

HR4= OCH




1= R3= OH R

2= R5= OCH

3 R4= H(A)

R1= R4= R5= OH R

2= H R

3= OCH

3(B) R

1= R5=

OH R2= R3= OCH

3 R4= H(C) R

1= R2= OCH

3 R3=

R5= OH R

4= H(D) R

1= H R

2= R3= OH(E) R

1= H

R2= OH R

3= OCH

3(F) R

1= OCH

3 R2= R4= OH R

3

= R5= H(G) R

1= R3= OH R

2= OCH

3(H) R

1= R5=

OH R2= R4= H R

3= OCH

3(I) R1= R3= OCH

3 R2=

R5= OH R

4= H(J) R

1= R2= R4= OH R

3= OCH

3 R5=

H(K) R1= OCH

3 R2= R4= H R

3= R5= OH(L) and

R1= R2= R3= OH R







Dloddigesii


Dnobile










50values




Polysaccharide

HPS-IB23



OAc3 120572-D-Gal 120572-D-Gal



GM-CSFuarr












T cell B cell

D nobile


D moniliforme


































Table 7 Continued







[58]











4 Conclusion






Acknowledgments


References












































































































of






Disease Markers



OncologyJournal of





PPAR Research



Journal of

ObesityJournal of




























1= R2=

OCH3R3= OH R

4= H (4) R

1= R2= R3= OCH

3R4= H

(5) R1= R2= OH R

3= R4= H (6) R

1= R3= OCH

3R2

= OH R4= H (7) R

1= OCH

3R2= R3= OH R

4= H (8)

R1= R3= OH R

2= R4= H (9) and R

1= R3= OH R

2=

HR4= OCH




1= R3= OH R

2= R5= OCH

3 R4= H(A)

R1= R4= R5= OH R

2= H R

3= OCH

3(B) R

1= R5=

OH R2= R3= OCH

3 R4= H(C) R

1= R2= OCH

3 R3=

R5= OH R

4= H(D) R

1= H R

2= R3= OH(E) R

1= H

R2= OH R

3= OCH

3(F) R

1= OCH

3 R2= R4= OH R

3

= R5= H(G) R

1= R3= OH R

2= OCH

3(H) R

1= R5=

OH R2= R4= H R

3= OCH

3(I) R1= R3= OCH

3 R2=

R5= OH R

4= H(J) R

1= R2= R4= OH R

3= OCH

3 R5=

H(K) R1= OCH

3 R2= R4= H R

3= R5= OH(L) and

R1= R2= R3= OH R







Dloddigesii


Dnobile










50values




Polysaccharide

HPS-IB23



OAc3 120572-D-Gal 120572-D-Gal



GM-CSFuarr












T cell B cell

D nobile


D moniliforme


































Table 7 Continued







[58]











4 Conclusion






Acknowledgments


References












































































































of






Disease Markers



OncologyJournal of





PPAR Research



Journal of

ObesityJournal of



















Dloddigesii


Dnobile










50values




Polysaccharide

HPS-IB23



OAc3 120572-D-Gal 120572-D-Gal



GM-CSFuarr












T cell B cell

D nobile


D moniliforme


































Table 7 Continued







[58]











4 Conclusion






Acknowledgments


References












































































































of






Disease Markers



OncologyJournal of





PPAR Research



Journal of

ObesityJournal of

















Polysaccharide

HPS-IB23



OAc3 120572-D-Gal 120572-D-Gal



GM-CSFuarr












T cell B cell

D nobile


D moniliforme


































Table 7 Continued







[58]











4 Conclusion






Acknowledgments


References












































































































of






Disease Markers



OncologyJournal of





PPAR Research



Journal of

ObesityJournal of



















T cell B cell

D nobile


D moniliforme


































Table 7 Continued







[58]











4 Conclusion






Acknowledgments


References












































































































of






Disease Markers



OncologyJournal of





PPAR Research



Journal of

ObesityJournal of



































Table 7 Continued







[58]











4 Conclusion






Acknowledgments


References












































































































of






Disease Markers



OncologyJournal of





PPAR Research



Journal of

ObesityJournal of




















Acknowledgments


References












































































































of






Disease Markers



OncologyJournal of





PPAR Research



Journal of

ObesityJournal of






























































































of






Disease Markers



OncologyJournal of





PPAR Research



Journal of

ObesityJournal of
















Evaluation of Chemical Constituents and Important ...ReviewArticle Evaluation of Chemical...

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