Plant Cell Wall Polymers: Function, Structure and Biological Activity of Their Derivatives

8/10/2019 Plant Cell Wall Polymers: Function, Structure and Biological Activity of Their Derivatives

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Chapter 4

Plant Cell Wall Polymers: Function, Structure

and Biological Activity of Their erivatives

Marisol Ochoa-Villarreal, Emmanuel Aispuro-Hernndez, Irasema Vargas-Arispuro and Miguelngel Martnez-Tllez

Additional in!ormation is a"aila#le at the end o! the chapter

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1. Introduction

Plant cell walls represent the most abundant renewable resource on this planet. They arerich in mixed complex and simple biopolymers, which has opened the door to thedevelopment of w ide applications in different technologic elds. In this regard thepolymerization processes that allow the syn thesis of t he cel l wall and their components in

living models ar e rel evant, as w ell as t he p roperties o f the p olymers and their d erivatives.Therefore t his chapter ou tlines t he b asis of polymerization with a b iological approach in theplant cell wall, highlighting the biological effects of plant cell wall derivatives a nd theircurrent applications.

Plant cell wall is a d ynamic net work h ighly organized which ch anges t hroughout the life ofthe cel l. The new primary cell wall is born in the cel l during cell division and rapidlyincreases in surface area during cell expansion. The middle lamella forms t he interface

between the primary walls of neighboring cellselaborate with the primary wall a secondary cell wall, building a complex structure

uniquely suited to the function of the cel l. The functions of the plant cell wall may begrouped by its con tribution to the st ructural integrity supporting the cel l membrane, senseextracellular i nformation and mediate si gnaling processes [ 1]. The m ain components of theplant cell wall involve different po lymers including polysaccharides, proteins, arom aticsubstances, and also w ater an d ions. Particularly, the d ifferent biomechanical properties o fthe plant cell wall are mainly dened by the content of the polymers cellulose,hemicelulloses an d pectins an d their i nteractions [ 2].

The rapid progress on plant cell wall research has allowed the comprehension of thedifferent structures, their biosynthesis an d functions. Nevertheless, there i s a n ew prominent

and worth line of research, the biological activity of some molecules d erived from the

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primary cell wall po lysaccharides. These active molecules named oligosaccharins byAlbersheim in the mid 70s, include the biologically active oligosaccharides that areproduced by partial hydrolysis of polymers of the cel l wall. The main biologically activecomponents of the cel l wall are t he p ectin-derived oligosaccharides, and the hemicellulosic-derived oligosaccharides. The biological r esponses of plants to oligosaccharins can bedivided into two broad categories: as m odulators of plant defense, and plant growth anddevelopment.

This information has p ermitted the use o f oligosaccharins as an alternative to improvedifferent aspects such a s yield and fruit quality, and may reach a h igher impact in the studyof the resi stance o f vegetable crop s.

2. Plant cell wall polymers

Plant cell wall is a co mplex matrix of polysaccharides t hat provides su pport and strengthessen tial for p lant cell survival. Properties co nferred by the ce ll wall are c rucial to the formand function of plants. The m ain functions of t he cel l wall comprise t he co nfer of resistance,rigidity and protect ion to the cell against differen t biotic o r ab iotic st resses, but still al lowingnutrients, gases and various intercellular s ignals to reach the plasma membrane. The wallprovides e nough rigidity to support the h eavy weight of high trees as l arge as 100 m height,

but also is exible and growth, cell turgor pressure provides high tensile stress to the wall, enabling itsenlargement due to the accum ulation of polymers d uring a com bination of stress relaxationcycles. The p rimary cell wall surrounds an d protects the inner c ell; it lies d own the middlelamella d uring growth and expansion [2]. The p rimary w all is thought to contribute to thewall structural integrity, cell adhesion, and signal transduction. In this ch apter w e focus onthe primary cell walls because it has been noted that m ost of t heir d erivatives exert a

biological function.

Plant cell wall is a d ynamic and highly specialized network formed by a heterogeneousmixture of cellulose, hemicelluloses and pectins, and in some ex tent proteins an d phenoliccompounds. Wall composition in vascular plants is approximately 30% cellulose, 30%hemicellulose an d 35% of pectin, with certain 1-5% structural proteins on dry weight basis.Cellulose an d hemicelluloses p olymers bring rigidity to the wall and pectin providesuidity throw the gelatinous polysaccharides m atrix. Cellulose and hemicelluloses areembedded in the amorphous pectin polymers and stabilized by proteins and phenoliccompounds. Hemicelluloses b ind to the surface of cellulose network preventing directcontact among m icrobrils, and pectin are linked to h emicelluloses forming a gel phase.

3. Components an d function of t he p rimary constituents of plant cell wall

3.1. Cellulose

Cellulose i s t he m ain cell wall polymer t hat brings s upport to the p lant. Cellulose i s a linearinsoluble u nbranched polymer of -(1,4)-D-Glucose r esidues as sociated with other cellulose


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chains by hydrogen bonding and Van der Waals forces. Cellulose chai ns agg regate togetherto form microbrils, which are h ighly crystalline a nd insoluble st ructures, each one a bout 3nm in diameter, chemically stable an d resistant to enzymatic at tack. Cellulose m icrobrils

comprise t he co re o f the p lant cell wall; one t hird of the total mass o f wall is cel lulose. Thevariation of dry w eight of cellulose i n a d icot such as Arabidopsis thaliana ranges from 15% ofleaf to 33% of stem walls. The walls of monocot grass species have a pproximately 610%cellulose i n leaves an d 2040% in stems [ 3].

Microbrils com prise t wo types of c ellulose cal led cellulose I and I. The I has a si ngle-chain triclinic unit cell, whereas cel lulose I has t wo chain monoclinic unit cell. In bothforms cel lulose in parallel and the terminal glucose res idues r otated 180 forming a atribbon in which cellobiose ( two glucose m olecules l inked by a -(1,4) bond) is t he repeatingunit [4]. Cellulose ch ains m ay align in paral lel (Type I) or an tiparallel (Type II ) orientation to

each other. Only the Type I conformation is kn own to naturally occur in plants; however,concentrated alkaline treatments may cause Type II cellulose to form during harshextraction procedures. The cel lulose chai ns may form the Type I or Typ e I conformationdepending on the ex tent of staggering of the ch ains in relation to each other. Probably theinteraction of cellulose m icrobrils with hemicelluloses m ay affect the ratio of Type I toType I cellulose [5]. The microbrilar d isposition allows the existence of micro spaces

between the microbrils that arand tissue t ype.

3.2. Hemicelluloses

Hemicelluloses ar e low molecular w eight polysaccharides as sociated in plant cell walls withlignin and cellulose. These h eterogenous gro up of polysaccharides t hat have -(1,4)-linked

backbones with an equatorial conguration astructural s imilarity [6]. Hemicelluloses i n dicotyledonous p lants comprise xyloglucans,xilans, mannans and glucomannans, while the -(1,3;1,4)-glucans are r estricted to Poalesand a few other groups. In addition, arabinoxylans are the main hemicellulosicpolisaccharides i n graminaceous s pecies s uch as w heat and barley, and in grasses [ 7].

3.2.1. Xyloglucan

Xyloglucan (XyG) is the most abundant hemicellulose i n primary cel l walls found in everyland plant species t hat has been analyzed. XyG are b ranched with -D-xylose l inked to C-6of the backbone. The most frequently xyloglucan structure in dicotyledonous oweringplants is the repeating heptamer integrated by four glucans residues w ith -D-xylosesubstituents in three constitutive glucans of the backbone, followed by a singleunsubstituted glucan residue (Figure 1) . The p resence o f this r epeating heptamer bl ock is anindicator of t he presence of XyG polysaccharides in dicots sp ecies [8]. Beside the XyGresidues, it may contain -D-galactose an d in less p roportion L-fucose--(1,2)-D-galactose;in all cas es the galactose residues are acetylated. The fact t hat al l t he substituents ofxyloglucans are con served denotes a h ighly biosynthesis control. On the other hand, in


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graminaceous monocots, XyG consist of 1 or 2 ad jacent -(1-6)-linked xylose r esidues w ithapproximately 3 unsubstituted -(1-4)-linked glucose b ackbone [9]. Despite the structuralvariability found in the sp ecies, the functions of the XyG in plants grow th and development

are hy pothesized to be conserved among all species of owering plants [ 10].

Figure !" Structure o f xyloglucan; principal component of t he h emicelluloses. The h eptamer bl ock is shown (glucan 4-xylose 3). In blue b ackbone -D-glucans; in red -D-xylose; in black -D-galactose a nd in

brown -L-fucose residues.

In dicotyledonous p lants exc ept for g raminaceous, the cel lulose an d xyloglucan are i n equalproportions. Some XyG chains are linked to the cellulose microbrils supporting theimportant role o f rigidity and maintenance o f the cel l, the res t XyG chains ar e cross- linked tocellulose m icrobrils and pectic polymers, and altogether integrate the complex cel l wallmatrix. In addition XyG is t hought to control cell wall enlargement potentially through theaction of -expansin, XyG endotransglucosylase or -(1,4)-endoglucanases [11]. Sever al

authors have revealed the XyG function by means of XyG-decient mutants of Arabidopsisthaliana , whereas t rying to elucidate t he rol of xyloglucan in cell wall biomechanics an d cellenlargement. More rec ently, mutations i n two xylosyltransferase g enes ( xx1/xx2) involved inXyG synthesis in Arabidopsis thaliana resulted in a X yG-decient mutant apparently normal

but reduced in size. Hypocotyl wall xx1/xx2 seedlings, suggestingthat XyG plays a s trengthening role in the cel l wall [12]. It was al so con rmed that whenXyG is missing, pectins an d xylans replace i ts role in cell wall biomechanics. The growthreduction in xx1/xx2 plants may stem from the reduced effectiveness of -expansin in theabsence of XyG [13]. These results represent t he complexity of t he study of individualcomponents in a p lant cell wall matrix, it is necessar y to point out the ad vantage of usingmultiple a ssays f or a b etter com prehension in the w all extensibility function.


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3.2.2. Xylans

Xylans are a d iverse group of polysaccharides with the com mon backbone of -(1,4)- linkedxylose residues, with side chains of -(1,2) linked glucuronic acid and 4- O-methylglucuronic aci d residues. Composition and distribution of the su bstitutions is w ide variableaccording to the p lant cell species. Xylans u sually co ntain many arabinose r esidues attachedto the backbone which are known as arabinoxylans and glucuronoarabinoxylans; hi ghamounts of arabinoxylans are present in the endosperm of cereals [14]. In graminaceousspecies xylans may be linked to the cellulose microbrils as the xyloglucan does indicotyledonous p lants, but the si de ch ain branches are no t attached; besides, the co ntent oflateral substituents d ecrease g radually during cell growth.

3.2.3. Mannans and glucomannans

The -(1,4)-linked polysaccharides rich in mannose or with mannose an d glucose i n a non-repeating pattern are the glucomannans and galactoglucomannans. Even though theirpresence i n primary cel l wall is low, mannans hav e been studied in their role as s eed storagecompounds, as evidenced by the embryo lethal phenotype in an Arabidopsis mutant that islacking the m ajor ( gluco) mannan synthase i n seeds [ 15].

3.3. Pectins

Pectins rep resent an outstanding family of cell wall polysaccharides w ith extraordinary

versatile, but not yet fully known structures and functions. In plants t he f unctions o f pectinsfullls important biological functions such as: growth, development, morphogenesis,defense, cellcell adhesion, wall structure, signaling, cell expansion, wall porosity, bindingof ions, growth regulators and enzymes modulation, pollen tube grow th, seed hydration,leaf ab scission, and fruit development [16]. The ex tracted pectins o f citrus p eel and applesare u sed as a g elling and stabilizing agent in food and cosmetic industries. Pectins w ithinthe fruits an d vegetables ar e p art of the d aily dietary ber and have m ultiple p ositive effectson human health including lowering cholesterol, serum glucose l evels, decrease occurrenceof diabetes an d cancer [17-19]. This p oints t he rel evance o f pectins i n diverse em erging eldsof study, even in human health.

Pectins ar e t he m ost wide com plex family of po lysaccharides i n nature. They are p resent inprimary walls of dicots and non-graminaceous m onocots w ith approximately 35%; in grassand other commelinoid primary walls 2-10% and up to 5% in walls of woody tissues [20].Pectins are formed with -(1,4)-D-galacturonic acid residues. Galacturonic acid (GalA)comprises ap proximately 70% of pectin linked at the O-1 and the O-4 positions [16]. Thestructural classes of the pectic polysaccharides include homogalacturonan (HG),rhamnogalacturonan I (RG-I), and rhamnogalacturonan II (RG-II). Also xylogalacturonan(XGA) and apiogalacturonan (AGA) have been d etermined. AGA is found in the walls ofaquatic plants such duckweeds ( Lemnaceae ) and marine seagrases ( Zosteraceae ) with apiose

residues 2,3-linked to homogalacturonan. The XGA is more abu ndant, has H G substituted


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by D-xylose residues which has been determined in multiple seagrasses, pea, apple, Arabidopsis , soybean with O-3 xylose an d xylose bran ches at O-2 byanother xyl ose r esidue [ 10].

3.3.1. Homogalacturonan

Homogalacturonan (HG) is the most abundant polymer of the pectins, it comprises near lythe 60 % of pectins i n plant cell wall [20]. HG is formed by long chains of linear 1, 4-linked -D-galacturonic aci d, some o f the carbo xyl groups ar e p artially methyl-esteried at C-6 andacetyl-esteried at p ositions O-2 and/or O-3 (Figure 2), depending on plant species.The linear units of HG in which more than 50% of the GalA are esteried withmethyl (or m ethoxy) groups at t he C-6 position are conventionally called high methyl-esteried HGs; otherwise they are referred as to low methyl-esteried HGs. The

unmethylated HG is negatively charged and may ionically interact with Ca 2+ to form astable gel w ith other pectin m olecules if 10> consecutive u nmethyl-esteried GalA residuesare coordinated; this is cal led the eg g box (Figure 3). The eg g box model can occur u ponCa 2+ inducing gelling approximately in 70% of the p ectin in plant cell walls [ 21].

Figure #" Homogalacturonan structure. Homogalacturonan is a linear polymer of -(1,4)-Dgalacturonic acid with methyl-esteried at C-6 an d acetyl-esteried at positions O -2 an d/or O -3.


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Figure $" The egg -box m odel of calcium crosslinking in homogalacuronan polysaccharides.These properties f avor t he g ellication process, therefore h ave been used by food technologists f or t he preparation of j ams, candies an d processed fruits p roducts. The g els ob tained using highly methyl- esteried HGs have a s hort and compact structure, are transparent and achieve a go od preservation of original avors; such g els are t hermo-reversible. On the op posite, the low methyl-esteried HGs ar e thermally irreversible g els an d only gell in the p resen ce of multivalent ions (Ca 2+ , Mg 2+ ).

3.3.2. Pectic br anched polymers: Rhamnogalacturonans-Iand Rhamnogalacturonans-II

Rhamnogalacturonan-I (RG-I) is a family of pectic polysaccharides t hat represent 20-35% ofpectin. It contain a b ackbone of the r epeating disaccharide galacturonic aci d and rhamnose:[-(1,2)-D-GalA--(1,4)-L-Rha] n partially substituted O-4 and/or O-3 positions of -Lrhamnose residues with single neutral glucosyl residues and with polymeric side chains predominantly of -(1,5)-L arabinans an d -(1,4)-D galactans, arabinogalactans-I (AG-

I), arabinogalactans-II (AG-II) and possibly galacto-arabinans [ 22]. The b ackbone may be O-acetylated on C-2 an d/or C -3 by -L-rhamnose r esidues. In contrast, there is no compellingevidence that t he residues are methyl-esteried, however, an enriched RG-I like wallfraction from ax has been reported to contain methyl esters [23]. The predominant sidechains contain linear and branched -L-arabinose and/or -D-galactose residues [20]these two are linked to approximately half of the rhamnose r esidues of the RG-I backbone(Figure 4) . The si de ch ains s howed a g reat heterogeneity according to the p lant sources; the-L-fucose, -D-glucuronic acid and 4- O-methyl -D-glucuronic acid, as ferulic andcoumaric aci d may b e p resent [24]. The core of the p olymeric s ide ch ains d oes n ot generallyexceed 50 GalA residues al though there are s ome excep tions like the galactan isolated from

tobacco cell walls, with 370 units [25]. RG-I side chains are d evelopmental and tissue-


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+)

specic d ifferentially regulated in the type of terminal sugars and oligosaccharides attachedto the backbone, it is not w ell understood but suggests d iverse functional specialization.Besides, the rhamnose residues may range from 20 to 80% depending on the pectin, plant

source an d extraction method [24]. It was s uggested the RG-I functions as a l inkage supportto other pect ic polysaccharides such as H G and Rhamnogalacturonans-II (RG-II), that arecovalently attached as si de ch ains [ 10].

Figure 4" Major s tructural features of Rhamnogalacturonan I. The ba ckbone is composed o f the disacchari de repeating u nit of -(1,2)-D-Galacturonic Acid--(1,4)-L-Rhamnose. Branched oligosaccharidescomposed predominantly of -L arabinose, in blue; and/or - D-galactose r esidues, in red.

Rhamnogalacturonans-II are the most complex an d branched polysaccharides of pectin. RG-II is a m inor pectic com ponent of plant cell walls with between 0.5 to 8% in dicots, non-graminaceous, monocots, and gymnosperms, and less than 0.1% in primary walls of


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commelinoid monocots [26]. The RG-II has a characteristic structure of seven to nineresidues of -D-galacturonic acid backbone with four branches clearly differentiateddesignated A, B, C and D (Figure 5).

RG-II has several kinds of substituents including 11 t o 12 d ifferent glycosyl residues, someof them rare su gars i n nature, like 2- O-methyl xylose, 2- O-methyl fucose, aceric aci d, 2- keto-3-deoxy-D-lyxo heptulosaric acid (Dha) and 2-keto-3-deoxy-D-manno octulosonic acid(Kdo) [27-30]. About 28-36 individual sugars, interconnected by more t han 20 differentglycosidic linkages that makes a highly complex polymer w ith an -D-galacturonic acid

backbone partially methyl esteried aoligosaccharide cha ins [31]. Despite the com plex st ructure an d low amount of the RG-II, it

r e %" Structure of Rhamnogalacturonan II. The backbone of RG-II is composed of -(1,4)-D- Galacturonic Acid residues. Four structu


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has been related with important and specic roles in cell walls. RG-II polymers are s elf-associated with borate forming borate-cross-linked RG-II dimers rstly demonstrated incomplexes d erived from sugar-beet [32], which contributes t o the mechanical properties ofthe p rimary w all with the three-dimensional pectic net work in muro [33]. Nearly 95% of t heRG-II polymers are in the dimmer complex form (dRG-II). The combination of the covalentcrosslinking among the pectic polymers HG, RG-I and RG-II sets the network of the plantcell wall, bringing together st rength, exibility and functionality to the c ells.

4. Biosynthesis of the p lant cell wall polymers

Cell wall biosynthesis b egins d uring cell division in the cytokinesis p hase through theformation of the cel l plate in the middle of the cel l. Eventually, the primary cell wall isassembled by the deposition of polymers of cellulose, hemicelluloses an d pectin. The

biosynthesis of wall polymers wall-related proteins and enzymes. Individual elements are channeled into theendomembrane system of endoplasmic reticulum and Golgi apparatus where they arepolymerized and modied. The former polymers are then transported through vesicles an dsecreted outside p lasma m embrane for s ubsequent assembling and linkage to the wall. Thismechanism is hi ghly regulated along the process and depends on the physiological state ofthe cel l and the i nterplay of signals g oing in and out of the cel l [34].

Specically, the long and rigid cellulose m icrobrils of plant walls ar e sy nthesized fromthe inner face of the plasma membrane by cellulose synthase (CESA) complexes, whichcomprise m ultiple subunits forming a rosette structure of s ix globular C ESA-containingcomplexes each of which synthesizes growing cellulose chains of 610 cellulosemolecules (For review, see [ 4]). Newly synthesized microbril is propelled by the act ionof the CESA, w hich polymerize the glucan chains in the specic positions driven bycortical microtubules [35]. Afterwards, microbril is linked with xyloglucans (XyG) andpectic polysaccharides to form the cell wall complex network. Matrix polysaccharidesnot only cross-link microbrils but also p revent the sel f association of new microbrilsinto larger ag gregates. XyG interacts with the formed microbrils in the surface an dalso may be trapped inside them [36]. It has been observed that in primary walls,microbrils linked to xyloglucan are smaller in diameter (less chain per ber) than

those in secondary w alls. Besides, the binding between XyG and cellulose is known toweaken cel lulose networks but increase their expansibility. The XyG is bound differentlyto three cellulose microbrils domains. The rst i s available to endoglucanases, t hesecond has to be solubilized by concentrated alkali and a third XyG is neither enzy meaccessible n or chemical [36]. According to this, the type of hydrolysis used to obtain thefractions of polysaccharides (oligosaccharides) in some assays results in products ofdifferent degree o f polymerization, which is related to some sp ecic biological functionsin the cell.

In contrast to cellulose, pectic p olysaccharides are syn thesized in the G olgi apparatus o f theplant cell, and then are s ecreted to the ap oplastic spa ce through vesicular com partment.


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Polysaccharides are t ransported from cis-face t o trans-face o f the Golgi w here they aresorted and packaged into vesicles of the trans-Golgi network for transport to the plasmamembrane. The movement of the vesicles containing the polymers is presumably along

actin laments that have myosin motors. It is no clear, how the synthesis of the pectinpolysaccharides i s initiated or w hether l ipid or p rotein donors are i nvolved. The possiblemodication of the p ectic g lycosyl residues m ay be est erication, O-mehtylation, acetylationand feruloylation by feruloyltransferases i n some Chemopodiaceae species [16 ].

To complete t he b iosynthesis o f polysaccharides, it is n ecessary the assem bly of the transportedelements t o form the functional matrix. This event involves bo th enzymatic an d non-enzymaticmechanisms in the apoplast [ 37]. The physicochemical proper ties exi sting in the wall aredependent on the hydrophobic and hydrophilic domains given by the water and solutes. Thehydrophobic domain is formed by the link of cellulose m icrobrils to the hy drogen bonds thatlead the excl usion of water from the interacting chains. The hydrophobic interactions m ay also

be controlled by enzymes that diminimicrobrils s uch as xy losidases and glucanases [38]. Meanwhile, the h ydrophilic d omain of thewall is gi ven by pectin polymers. Together, both domains con tribute to the protoplast matrixmedium leading the rearrangement of some polymers as the homogalacturonan. Linearhomogalacturonans are synthesized in a highly methyl-esteried form in the Golgi andtransported to the wall i n membrane vesicles to be desesteried by wall l ocalized pectinmethylesterases. The conversion of t he HG from the methylesteried form to the negativelycharged form has been associated with the d ecrease of growth [39].

The glycosiltransferases and hydrolases ar e enzymes localized in the Golgi apparatus an d

work together to produce the xyloglucan precursors. Some changes take place af ter thesynthesis of hemicelulloses i n the Golgi. It h as been shown that a specic apoplasticglycosidases are re sponsible for t he t rimming of new xyloglycan chains an d this determinesthe heterogeneity of t he polymer i n the cell wall [6]. Hydrolases ar e likely to play animportant role in determining hemicelluloses structures in the cel l wall, and are co expressedwith polysaccharide biosynthetic enzymes. For detailed information about the cell wallrelated enzymes see [ 4,6,10,16,40].

In the last decades m any biochemical approaches h ave enabled the identication andcharacterization of the structure of cell wall polymers and the enzymes involved in their

biosynthesis. Beside classi Arabidopsis thalianamutants ha s been a breakthrough to reveal specic functions of certain components of thewall. The ad vances in the d etermination of the st ructures of polymers through microscopyprovide o ne of the b est views of the o rganization and structure al lowing the d evelopment ofdifferent plant cell wall models. Immunolocalization studies also h ave sh own the location ofsome polysaccharides w ithin the cel l wall and in the ap oplastic region. For instance, lowmethyl-esteried HGs ar e located in the middle lamella at the cel l corners and around airspaces, whereas h igh methyl-esteried HGs are present t hroughout the cell wall [20].Therefore, non-destructive methodologies such as NMR have been key techniques forelucidating the t opology, dynamic an d tridimensional arrangement of s ome cel l st ructures,contributing to the cel l wall knowledge.


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5. Biological activity of p lant cell wall derivatives

Exhaustive studies on the structure an d function of the plant cell wall have led to the

discovery of biologically active molecules derived from its polymeric carbohydratecomponents. These molecules are found in nature and can be released by acid, basic orenzymatic hydrolysis of the primary cell wall polysaccharides. Due to the complexcombination of carbohydrate p olymers in the cel l wall of plants, there are vari ations amongthe p hysicochemical structure of hydrolyzed fragments, which exerts striking differences onactivity and specicity to regulate some physiological proces ses in plants. These plantoligosaccharides w ith regulatory properties w ere called oligosaccharins and have beenextensively studied by the workgroup of Albersheim since the mid-70s (reviewed in [41]).Among the oligosaccharins derived from plants, the most active and therefore the moststudied are t hose d erived from pectins and hemicelluloses, whose m ain regulatory functions

depend on the degree of polymerization, chemical composition and structure, and can bedivided in two broad categories: activation of plant defense mechanisms an d plant growthand development.

In order to exert their regulatory p roperties, oigosaccharins must be rst recognized byspecic plant cell receptors which may be lectin-type proteins cap able of transmitting thesignal into the cell [42]. Even when the complete recognition mechanisms and signalingpathway for plant-derived oligosaccharins is far from being fully understood, proteinreceptors that recognize these molecules have been characterized in the model p lant

Arabidopsis thaliana [43-44] and its believed the downstream processes may occur vi a MAPkinases activity [45] (For review about the detailed perception mechanisms ofoligosaccharines b y plants, see [46]).

5.1. Pectin-derived oligosaccharins

Even when the most abundant component of pec tins is the galacturonic acid, partialdepolymerization of the pectic polysaccharides generates fragments that m ay (or not)contain other residues such as rhamnose, galactose, arabinose, xylose, glucose an dmannose [20]. This combination confers variability to the structure, and thereby to the

biological activity of the oligosaccharins. The oligosachomogalacturonan are called oligogalacturonides (OGAs), which are linear ol igomers ofgalacturonic acid, where some residues may be methyl-esteried or acet ylated. OGAs areelicitors of defense responses in plants, triggering the synthesis and accumulation ofphytoalexins (antimicrobial compounds) and other m olecular i ndicators of the act ivation ofdefensive patterns, such as the induction of pathogenesis related proteins and genesrelated to the hypersensitive reaction [47]. OGA-induced defense response patterns aresummarized in Table 1.

OGAs trigger t he rapid accumulation of reactive oxygen species (ROS) in plants, which isnecessary for the deposition of callose, polysaccharide produced in response to woundingand pathogen infection. Furthermore, ROS are si gnaling molecules o f several intracellularevents. Therefore it was proposed ROS were involved in the OGA-induced resistance


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against fungal pathogens in three d ifferent ways: (1) d irectly exerting a cytotoxic effect tothe invading pathogen, (2) inducing callose d eposition for r einforcing the p lant cell wall,and (3) mediating the signals leading to the expression of defense related genes an d

defensive metabolites [ 48]. Nevertheless, recent ndings in Arabidopsis thaliana showed thatthe d efensive gene act ivation was n ot directly correlated to the accu mulation of hydrogenperoxide, and that OGA-induced resistance agai nst the fungal pathogen Botryti s cinerea wasindependent of both the o xidative burst and callose d eposition [49].

BIOLOGICAL ACTIVITY PD ORGANISM REFERENCEDefense ResponsesPhytoalexin synthesis 8-13 Glycine max [77]

3-12 Glycine max [78] 3 Petroselinum sativum [79]

9-15 Phaseolus vulgaris [80,81]Induction of phenylalanine am monia-lyase > 9 Daucus ca rota [82]9-15 Phaseolus vulgaris [80,81]

Induction of chalcone synthase 9-15 Phaseolus vulgaris [81]Induction of -(1,3)-glucanase 3 Petroselinum sativum [79]Lignin synthesis 8-11 Cucumis sativus [83]

9-15 Phaseolus vulgaris [81]

Protease inhibitors synthesis 2-3Lycopersicumesculentum [84]

Growth and Development

Induction of et hylene production5-19

Lycopersicum

esculentum

[85]

5-19 Pyrus communis [86]Steem growth inhibition > 8 Pisum sativum [87]

Protease inhibitors synthesis 10-14 Nicotiana tabacum [88,89] Quality Parameters

Increase of the col or an d anthocyanin content 3-20 Vitis vinifera [91]

Ta&le !" Biological activity exerted by oligogalacturonides w ith respect to the d egree o f polymerization

Plants treated with OGAs exhibit an enhanced resistance to pathogen infections. Theinduction of the defensive genes, peroxidase an d -(1,3)-glucanase h as b een related to theenhanced resistance of OGA-treated Arabidopsis thaliana against Botryti s cinerea [50-51].Peroxidases are a ssociated to the p lant cell wall reinforcement by the sy nthesis of lignin,while -(1,3)-glucanase could affect mycelium growth by hydrolyzing glucan chains fromthe w all of fungi [50]. In grapevine ( Vitis v inifera L.), OGAs hi ghly stimulated the enzymaticactivity of chitinase a nd -(1,3)-glucanase a nd induced the expression of defense r elatedgenes i n different extent, which also l ed to a p rotection against Botryti s cinerea [47]. Somegenes related to the formation of phytoalexins from the phenylpropanoid pathway wereexpressed rapidly and transient, various ch itinase i soforms w ere ex pressed rapidly but theirinduction was m ore sustained, and some inhibitors of fungal hydrolytic enzy mes were up-regulated later.


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The degree of acetylation and methylation of OGAs has been less add ressed but emergingresearch showed the inuence of these functional group substituents on plant defenseresponses. The effect of the d egree of acetylation of OGAs on the el icitation of defenses inwheat ( Triticum aestivum L.) was studied by Randoux and coworkers [52]. It was found bothacetylated and unacetylated OGAs induced accumulation of hydrogen peroxide at the siteof fungal penetration, through activation of oxalate oxidase, which is also rel ated to theenhanced peroxidase a ctivity. Besides, the induction of lipoxigenase a ctivity demonstratedthe st imulation of the octadecanoid pathaway. Moreover, transgenic strawberries ( Fragariavesca L.) producing partially demethylated OGAs displayed an enhanced resistance ag ainstBotryti s ci nerea [53].

Table 1 show s that OGAs modulate diverse grow th and developmental processes in plants.Early responses related to the signaling transduction pathways comprise membranedepolarization, cytosolic aci dication, apoplast alkalinization and calcium mobilization at

the plasma membrane level, due to the activity of Ca2+

channels. Calcium ions are veryimportant second messengers in plants and its level in intracellular compartments isdeterminant for t he k ind of physiological response. In tobacco cells O GAs induced differentpatterns of Ca 2+ inux into cytosol, mitochondria and chloroplasts [54]. The increase incytosolic free C a 2+ has been proposed to mediate the regulation of stomatal aperture andproduction of hydrogen peroxide in the guard cells of tomato ( Licopersicon esculentum L.)and Commelina communis L. [55]. Calcium may also d irectly interact with long-sized OGAspromoting the formation of structures with an egg-box conformation, which maypotentiate their biological activity [56]. Nevertheless t he promotion of veg etative shootformation in Nicotiana tabacum explants has been observed to be independent of exogenous

Ca2+

[57].OGAs regulate morphogenesis in plant tissues i n a process associated with the act ion ofauxins, which are growth-regulating phytohormones. Particularly, OGAs and auxinsappear to play an antagonist role; since OGAs inhibit the expression of some auxin-inducible genes steps downstream of the auxin perception [58]. In this sense, rootdifferentiation induced by OGAs was studied in Arabidopsis thaliana seedlings, wheretreatments decreased trichoblasts length but increased the number and length of roothairs [59]. Similar results were found in maize ( Zea mays L.) seedlings where OGAsinhibited coleoptile growth and modied root architecture by inducing lateral rootformation [59]. The growth inhibitory a ctivity exerted by OGAs seems to be cau sed by (1)inhibition of cell elongation; since cel l division in the p rimary root meristem is n ot altered[59] and (2) inactivation of a ki nase en zyme implicated in the TOR signaling pathway,which integrates nutrient and growth factor signals in eukaryotic cells [60]. On thecontrary OGAs induced primary root length growth in alfalfa ( Medicago sativa L.)seedlings [61], which conrms that OGA-inducing activities are dependent on the plantspecies perceiving the signal.

Interestingly, the structure and stimulating activity of a rhamnogalacturonan I-derivedoligosaccharide ( RG-IO) isolated from owers o f Nerium indicum Mill. was i nvestigated [62].The st ructural features of the oligomer consisted in a rham nogalacturonan backbone w ith


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several branches O-4 linked to L-rhamnose residues. To determine the structure of the branches the oligomer was partialy hid

MS). Branches w ere found to be m ainly composed by -(1,4)-D-galactan, a h ighly branchedarabino -(1,3;1,6)-D-galactan, and -(1,5)-L-arabinan. Fu rthermore, R G-IO stimulated invitro the production of nitric oxide in macrophage cel ls. Removal of some side ch ains fromRG-IO reduced nitric oxide production, pointing out the rel evance of the branches for its

biological activity.

5.2. Hemicellulose-derived oligosaccharins

Xyloglucan is t he m ain hemicellulosic com ponent of t he p lant cell wall. Biological effects ofxyloglucan derivatives are related to the intrinsic physiological f unction of polymericxyloglucan in plant cells, comprising the co ntrol of extensibility and mechanics of t he cel l

wall and cell expansion. Most research in this eld highlights t heir r egulatory activity oncell growth and elongation, which relies i n the molecular si ze, distribution, and levels ofsubstituted xylosyl units with galactosyl and fucosyl residues [63]. It has b een observedactive xyloglucan oligomers (XGOs) accelerate cel l elongation in peeled stem segments ofPisum sativum [64], and in suspension-cultured cells of Nicotiana t abacum , expansion led tocell division [65]. On the con trary, treatments with polymeric xyloglucan suppressed cellelongation [64-65], indicating that m olecular size is a determinant factor of responsespecicity.

Xyloglucan-derived octasaccharides promoted growth of coleoptiles in wheat seedlingsand induced a rap id increase o f -L-fucosidase act ivity in Rubus fruticosus protoplasts [63].In wheat immature embryos a xyl oglucan-derived pentasaccharide induced rhizogenesisand stimulated the formation of callus an d meristematic zo nes [66]. A fucose-galactose-xylose trisaccharide fragment of xyloglucan inhibited ethylene biosynthesis, stimulatedembryogenesis in cell cultures of cotton ( Gossypium hirsutum L.) and formation of callus[67]. In contrast, a mixture of XGOs induced ethylene production in whole fruits ofpersimmon ( Diospyros kaki L.). Interestingly, non-fucosylated XGOs augmented ethylenelevels in a greater extent t han fucosylated XGOs [68]. Also, XGOs lacking the fucosylresidue were inactive to modulate potato resistance to disease [69], and to inhibitgibberellic acid-induced elongation of pea ( Pisum sativum L.) epicotyls [70], when

compared to fucosylated XGOs. These observations altogether may provide a clue to a better understanding of the re

the sen sitivity of the response.

On the other hand, galactoglucomannan is composed by a backbone of glucose andmannose residues w ith side chains of galactose. More rec ent r esearch about cell walloligosaccharides derivatives has demonstrated a growth-regulating activity ofgalactoglucomannan-derived oligosaccharins at very low concentrations.Galactoglucomannan oligosaccharides (GGMOs) modulate root morphology in mung

bean ( Vigna radi ata L.) [71] and Karwinskia humboldtiana [72] by a respective induction or

inhibition of adventitious root formation. More recent re search found GGMOs inhibitedlateral roots formation but stimulated


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their elongation, without any effect on adventitious root elongation in mung beanseed lings [73].

Furthermore, GGMOs inhibited the elongation induced by exogen ous phytohormones of

pea stem segments [74], root and hypocotyl growth of mung bean [71, 73] and K.humboldtiana roots [72], indicating an antagonist activity of GGMOs against growthregulators, such as 2, 4-dichlorophenoxyacetic aci d, indole-3-acetic aci d, indole-3-butyricacid, 1-naphthaleneacetic acid and gibberellic acid, at d ifferent extent. In addition, anincrease i n the act ivity of cell wall associated peroxidases h as b een reported during theGGMO-mediated inhibition of the elongation of hypocotyls in mung bean plants [73] andepicotyls in peas [75]. Which suggests the growth inhibition caused b y GGMOs may bethe r esult of processes cat alyzed by plant cell wall peroxidases.

5.3.Cellulose-derived oligosaccharins

During many years it was thought that only non-cellulosic oligosaccharides derivedfrom plant cell wall were biologically active. Surprisingly, i t has been recentlydemonstrated that fragments of oligosaccharides released during cellulose d egradation,called cellodextrins (CD), induce a variety of defense res ponses i n grapevine cel ls. CDare ol igomers of linear -(1,4)-linked glucose res idues. The induction of oxidative burst,transient elevation of cytosolic Ca 2+ , expression of defense-related genes, andstimulation of chitinase and -1,3-glucanase activities were triggered by CD ingrapevine cells. Also, CD oligomers with a degree of polymerization 7 enhanced

protection in detached leaves of grapevine against Botryti s cinerea , suggesting CD areimportant elicitors of defense react ions [76]. These res ults have opened the door to thestudy of many other biological processes where CD may be involved and to elucidatetheir action mechanisms in plants.

6. Current applications o f plant cell wall-derived oligosaccharins

Increasing knowledge of the factors that modulate the biological activity of cell wall-derived oligosaccharides h as n aturally led to the development of technologies ai med toexploit the p otential of these m olecules i n different elds. The rst successful applications

occurred in agriculture, where different crops can now be treated with commerciallyavailable preparations of pectin-derived-oligosaccharins in order to enhance the basalresistance o f plants, and decrease t he possible losses related to phytopatogenic infections.Another alternative is the use of oligosaccharins to improve t he yield, as seen in tomato(Lycopersicum esculentum Mill.), where f oliar t reatments increased fruit yield by up to 40%with respect to the non-treated controls, and improved parameters of qu ality such assoluble sol ids con tent (SSC), acidity and rmness [ 90]. Encouraging results were found inVitis vinifera L., since preharvest treatments of clusters with pectin-derivedoligosaccharides enhanced the red color of table grapes cv. Flame Seedless withoutaffecting berry rmness neither SSC. Berry color enhancement was achieved due to a


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higher an thocyanin content in berry skin, given by the st imulation of t he p henylpropanoidpathway [91]. Recent n dings showed an increase in the antioxidant capacity of OGA-treated table g rapes cv. Red Globe and Flame Seedless, as a consequence o f the i nduction

of anthocyanins, avonoids and phenolic compounds (non-published data). As a result ofthis r esearch it was g enerated a reg ister m ethod for con trolling coloration in table g rapes based on oligogalacturonide (92)

industry of cosmetics. This emerging trend is based on the ability of OGAs to stimulateadhesion of keratinocytes t o proteins o f the d ermoepidermal junction. This b iological effectis ap parently exerted by OGAs with a d egree of polymerization 5 as i ndicated in the USpatent [93]. However, further research is necess ary t o continue with the development ofreliable applications.

Author d etails

Marisol Ochoa-Villarreal, Emmanuel Aispuro-Hernndez an d Miguel A. Martnez-Tllez*Laboratorio d e Fi siologa V egetal Molecular. Tecnologa d e A limentos de O rigen Vegetal, Centro d e I nvestigacin en Alimentacin y Desarrollo, A.C., Hermosillo, Sonora, Mxico

Irasema Vargas-ArispuroLaboratorio de Ecologa Q umica. Ciencia d e los A limentos, Centro de Investigacin enCentro d e I nvestigacin en Alimentacin y Desarrollo, A.C., Hermosillo, Sonora, Mxico

Acknowledgement

The au thors appreciate the support of Juan Reyes C aldern with the ed ition of the guresshown in this c hapter.

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Plant Cell Wall Polymers: Function, Structure and Biological Activity of Their Derivatives

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