Structural characterization of red wine rhamnogalacturonan II

Pellerin, Patrice; Doco, Thierry; Vidal, Sergi; Williams, Pascale; Brillouet, Jean‐Marc; O’Neill, Malcolm A.

doi:10.1016/0008-6215(96)00139-5

Cited by 205 publications

(152 citation statements)

References 27 publications

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“…Wall-bound mRG-II molecules inserted within homogalacturonan chains may be structurally constrained in a manner that favors borate ester formation, and the cross-link, once formed, may be stabilized by the interaction of Ca 2ϩ ions with both dRG-II-B and homogalacturonan. Soluble mRG-II has a backbone composed of between eight and 15 1,4-linked ␣-dgalacturonosyl residues (Whitcombe et al, 1995;Pellerin et al, 1996). Consequently, soluble dimer formation and stability are in large part promoted by the interaction of divalent cations with RG-II .…”

Section: The Stability and Function Of Drg-ii-b In Muromentioning

confidence: 99%

“…RG-II is present in the wall predominantly as a dimer (dRG-II-B) that is cross-linked by a 1:2 borate:diol ester (Ishii and Matsunaga, 1996;Kobayashi et al, 1996;O'Neill et al, 1996;Kaneko et al, 1997). A single borate ester is believed to cross-link two of the four apiosyl residues present in dRG-II-B (Ishii and Matsunaga, 1996;O'Neill et al, 1996;Pellerin et al, 1996). These studies have led to the suggestion that a physiologically important role of B is to covalently crosslink wall pectins Brown and Hu, 1997;Kobayashi et al, 1997;Matoh, 1997), since the B requirement and wall pectin content are correlated in many plants (Hu and Brown, 1994;Hu et al, 1996;Matoh et al, 1996).…”

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The Pore Size of Non-Graminaceous Plant Cell Walls Is Rapidly Decreased by Borate Ester Cross-Linking of the Pectic Polysaccharide Rhamnogalacturonan II

1999

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The walls of suspension-cultured Chenopodium album L. cells grown continually for more than 1 year on B-deficient medium contained monomeric rhamnogalacturonan II (mRG-II) but not the borate ester cross-linked RG II dimer (dRG-II-B). The walls of these cells had an increased size limit for dextran permeation, which is a measure of wall pore size. Adding boric acid to growing B-deficient cells resulted in B binding to the wall, the formation of dRG-II-B from mRG-II, and a reduction in wall pore size within 10 min. The wall pore size of denatured B-grown cells was increased by treatment at pH < 2.0 or by treatment with Ca 2؉ -chelating agents. The acid-mediated increase in wall pore size was prevented by boric acid alone at pH 2.0 and by boric acid together with Ca 2؉ , but not by Na ؉ or Mg 2؉ ions at pH 1.5. The Ca 2؉ -chelator-mediated increase in pore size was partially reduced by boric acid. Our results suggest that B-mediated cross-linking of RG-II in the walls of living plant cells generates a pectin network with a decreased size exclusion limit for polymers. The formation, stability, and possible functions of a borate ester cross-linked pectic network in the primary walls of nongraminaceous plant cells are discussed.

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Section: The Stability and Function Of Drg-ii-b In Muromentioning

confidence: 99%

mentioning

confidence: 99%

The Pore Size of Non-Graminaceous Plant Cell Walls Is Rapidly Decreased by Borate Ester Cross-Linking of the Pectic Polysaccharide Rhamnogalacturonan II

1999

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“…16 Red wine was purchased from a local store. One bottle of red wine (760 ml) was concentrated to about 50 ml by a rotary evaporator at 40˚C.…”

Section: Methodsmentioning

confidence: 99%

11B Solid-state NMR Investigation of the Rhamnogalacturonan II-borate Complex in Plant Cell Walls

et al. 2006

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IntroductionBoron (B) is an essential trace element for vascular plants. 1,2 We have been studying the chemical form and function of B in plants. [3][4][5][6][7][8][9] Our in vivo solution state 11 B NMR study revealed that B in plant tissues exists in two forms, that is, water-soluble and water-insoluble, which is in vivo NMR observable and unobservable, respectively, and that the water-soluble B is a borate ester with low-molecular-weight diol compounds (1:1 and 1:2) as well as boric acid (Fig. 1). 3,4 Matoh's group reported that water-insoluble B is located in the cell walls 10 and that a dimeric rhamnogalacturonan II-borate (dRG-II-B) complex, in which two monomeric RG-IIs are cross-linked by borate-diol (1:2) esterification, was isolated and identified from enzymatic digests of radish cell walls. 11 Recently, we showed that RG-II is covalently linked to homogalacturonan, a major component of pectin in plant cell walls, 7 and that dRG-II-B formation in cell walls contributes to wall stabilization.8 From these studies, we have concluded that the primary function of B in plants is to covalently cross-link wall pectin by dRG-II-B formation, and thereby to contribute to the strength and integrity of cell walls. 2,8 Solution NMR studies have proven that enzymatically solubilized dRG-II-B from cell walls has the borate-diol (1:2) structure; 5,6,9,11,12 however, there is no direct evidence that water-insoluble and solid state B in the cell walls is present as a borate-diol ester (1:2) that cross-links pectin molecules. Thus, a nondestructive analysis of the chemical form of B in plant cell walls is needed to confirm our conclusions regarding the function of B in these walls.Solid-state NMR is an emerging analytical methodology for molecular structure, which is not limited by either insolubility or difficulty in crystallization, and makes it possible to address a variety of structural and dynamic questions at atomic-level resolution. 13,14 The 11 B nucleus has an electric quadrupole moment (I = 3/2), which frequently gives rise to a characteristic asymmetric NMR line shape and difficulty in observing the isotropic chemical shift. 15 However, in a tetrahedral B environment the local electric field gradient (EFG) is small. Moreover, the quadrupole interaction is inversely proportional to the applied magnetic field. Therefore, we would be able to observe the isotropic chemical shift of 11 B in a tetrahedral configuration by using high-magnetic field NMR with magic angle spinning (MAS). Consequently, to clarify the chemical form of B in plant cell walls, we performed 192-and 96-MHz 11 B MAS NMR measurements for solid state dRG-II-B and plant cell wall (sugar beet fiber). The boron in plant cell walls, which is water-insoluble and in the solid state, is solubilized by pectinase digestion to give a dimeric rhamnogalacturonan II-borate (dRG-II-B) complex. To clarify the nondestructive structure of boron present in plant cell walls (as represented by sugar beet fiber), we performed 192-and 96-MHz 11 B solid state NMR measur...

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“…Polysaccharides are an important group of macromolecules in grapes and include: arabinogalactan-proteins (AGPs) (Saulnier and Article available at http://www.ctv-jve-journal.org or http://dx.doi.org/10.1051/ctv/20142901016 Brillouet, 1989;Brillouet et al, 1990;Saulnier et al, 1992;Pellerin et al, 1995;Pellerin and Cabanis, 1998;Doco et al, 2000;Vidal et al, 2001;Vidal et al, 2003), arabinans (Villetaz et al, 1981;Belleville et al, 1993), and rhamnogalacturonan type II (RG-II) (Belleville et al, 1993;Doco and Brillouet, 1993;Pellerin et al, 1996;Doco et al, 1997;O'Neill et al, 2004).…”

Section: Introductionmentioning

confidence: 99%

“…RG-II consists of a main chain of seven to nine galacturonic acids units with four lateral oligosaccharide chains (Doco et al, 1993;O'Neill et al, 2004). These chains contain arabinose, rhamnose, fucose, galactose, galacturonic and glucuronic acids and also rare sugars as 2-O-methyl-fucose, apiose, 2-O-methyl-xylose, KDO (2-Keto-3-deoxy-D-mannooctulosonic acid), DHA (3-deoxy-D-lyxohepyulosaric acid) and aceric acid (3-C-carboxy-5-deoxy-L-xylose) (Doco et al, 1993;Pellerin et al, 1996;Ridley et al, 2001;O'Neill et al, 2004). RG-II is resistant to pectolytic enzymes and is found in fruit juice and wine obtained by total liquefaction with pectinases (Doco et al, 1997).…”

Section: Introductionmentioning

confidence: 99%

The role of polysaccharides on the grape must ultrafiltration performance

Sousa

Pinho

Santos

2014

Ciência Téc. Vitiv.

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SUMMARYThis work addresses ultrafiltration of grape must and the understanding of the membrane/polysaccharides interactions due to the chemical composition of the soluble grape must polysaccharides. The performance of two laboratory-made cellulose acetate membranes was investigated. The membranes have molecular weight cut-off of 96 kDa (CA-400-32) and 31 kDa (CA-400-28). To identify the different polysaccharides in the fractions obtained by ultrafiltration, these molecules were isolated by dialysis, then concentrated, freeze-dried and the polysaccharide composition analysed by Gas-Chromatography with flame ionization detector after acid hydrolysis, reduction and acetylation. Polysaccharides adsorbed on the membranes were also identified and quantified by Gas-Chromatography, after hydrolysis, reduction and acetylation of the known mass of dehydrated membrane. The analysis of the membrane matrix, give evidence that mannoproteins were adsorbed on the matrix of CA-400-32 membrane, which has originated, in some extension, the clogging of the pores. It was concluded that the ramnogalacturonan type II crossed the CA-400-32 membrane easily, however its depletion in the retentate and permeate streams over time may be due to its accumulation on the membrane surface, probably caused by adsorption. Arabinogalactan-proteins and mannoproteins were found in the permeate stream of the CA-400-32 membrane, whilst in the CA-400-28 membrane, ramnogalacturonan type II and the majority of arabinogalactan-proteins and mannoproteins remained in the retentate. RESUMOEste trabalho visa a ultrafiltração do mosto e o estudo das interações membrana/polissacáridos devido à composição química dos polissacáridos do mosto. Foi investigado o desempenho de duas membranas de acetato de celulose feitas em laboratório. As membranas têm um limite de exclusão molecular de 96 kDa (CA-400-32) e 31 kDa (CA-400-28). Para identificar os diferentes polissacáridos nas frações obtidas por ultrafiltração, as moléculas foram isoladas por diálise, concentradas, liofilizadas e a composição em polissacáridos analisada por cromatografia gasosa com detector de ionização de chama, após hidrólise ácida, redução e acetilação. Os polissacáridos adsorvidos nas membranas foram também identificados e quantificados por cromatografia gasosa, após hidrólise, redução e acetilação duma massa conhecida de membrana desidratada. A análise da matriz da membrana, mostrou que manoproteínas foram adsorvidas na matriz da membrana CA-400-32, o que originou, em alguma extensão, o entupimento dos poros. Concluiu-se que a ramnogalacturonana tipo II atravessou a membrana CA-400-32 facilmente, no entanto a sua diminuição ao longo do tempo no retentado e permeado pode ser devido à sua acumulação na superfície da membrana, provavelmente causada por adsorção. As arabinogalactanas-proteínas e as manoproteínas foram encontrados no fluxo do permeado da membrana CA-400-32, enquanto na membrana CA-400-28, a ramnogalacturonana tipo II e a maioria das arabinogalactanas-proteínas e manoproteínas perman...

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Structural characterization of red wine rhamnogalacturonan II

Cited by 205 publications

References 27 publications

The Pore Size of Non-Graminaceous Plant Cell Walls Is Rapidly Decreased by Borate Ester Cross-Linking of the Pectic Polysaccharide Rhamnogalacturonan II

The Pore Size of Non-Graminaceous Plant Cell Walls Is Rapidly Decreased by Borate Ester Cross-Linking of the Pectic Polysaccharide Rhamnogalacturonan II

11B Solid-state NMR Investigation of the Rhamnogalacturonan II-borate Complex in Plant Cell Walls

The role of polysaccharides on the grape must ultrafiltration performance

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