Isolation and partial characterization of feruloylated oligosaccharides from maize bran

Saulnier, Luc; Vigouroux, Jacqueline; Thibault, Jean‐François

doi:10.1016/0008-6215(95)00053-v

Cited by 286 publications

(197 citation statements)

References 24 publications

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“…One study has found that xylan from maize bran contains Gal-Xyl-Ara trisaccharide substituents. 25 To investigate what structure the observed 5.42-ppm proton resonance in Arabidopsis acetylated xylan is attributed to, we employed 2-dimensional (2D) total correlation NMR spectroscopy (TOCSY) to analyze the structural units of wildtype Arabidopsis xylan. It has previously been shown that in the 2D 1 H-1 H TOCSY spectrum of E. globulus xylan, the H-1 signal of the Gal-MeGlcA disaccharide substituents at 5.42 ppm has correlation cross peaks with H-2 proton at 3.77 ppm.…”

Section: 23mentioning

confidence: 99%

Identification of a disaccharide side chain 2-O-α-D-galactopyranosyl-α-D-glucuronic acid inArabidopsisxylan

Zhong

Teng

Lee

et al. 2014

Plant Signaling & Behavior

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Section: 23mentioning

confidence: 99%

Identification of a disaccharide side chain 2-O-α-D-galactopyranosyl-α-D-glucuronic acid inArabidopsisxylan

Zhong

Teng

Lee

et al. 2014

Plant Signaling & Behavior

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“…A common feature of grass xylans is the further substitution of the feruloyl-α-L-arabinofuranosyl residues with β-D-xylose linked to O-2 of the arabinose (13)(14)(15)(16)(17). Some of these xylosyl residues can be further substituted with β-1,4-linked D-galactose (18). Among these ferulate-containing xylan sidechain variants, 2-O-β-D-xylopyranosyl-(5-O-feruloyl)-L-arabinose has been found to be the most abundant, and in some cases is as abundant as 5-O-feruloyl-Larabinofuranose (13,15,19).…”

mentioning

confidence: 99%

XAX1 from glycosyltransferase family 61 mediates xylosyltransfer to rice xylan

Chiniquy

Sharma

Schultink

et al. 2012

Proc. Natl. Acad. Sci. U.S.A.

176

161

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Xylan is the second most abundant polysaccharide on Earth and represents an immense quantity of stored energy for biofuel production. Despite its importance, most of the enzymes that synthesize xylan have yet to be identified. Xylans have a backbone of β-1,4–linked xylose residues with substitutions that include α-(1→2)–linked glucuronosyl, 4- O -methyl glucuronosyl, and α-1,2- and α-1,3-arabinofuranosyl residues. The substitutions are structurally diverse and vary by taxonomy, with grass xylan representing a unique composition distinct from dicots and other monocots. To date, no enzyme has yet been identified that is specific to grass xylan synthesis. We identified a xylose-deficient loss-of-function rice mutant in Os02g22380, a putative glycosyltransferase in a grass-specific subfamily of family GT61. We designate the mutant xax1 for x ylosyl a rabinosyl substitution of x ylan 1. Enzymatic fingerprinting of xylan showed the specific absence in the mutant of a peak, which was isolated and determined by 1 H-NMR to be (β-1,4-Xyl) 4 with a β-Xyl p -(1→2)-α-Ara f -(1→3). Rice xax1 mutant plants are deficient in ferulic and coumaric acid, aromatic compounds known to be attached to arabinosyl residues in xylan substituted with xylosyl residues. The xax1 mutant plants exhibit an increased extractability of xylan and increased saccharification, probably reflecting a lower degree of diferulic cross-links. Activity assays with microsomes isolated from tobacco plants transiently expressing XAX1 demonstrated xylosyltransferase activity onto endogenous acceptors. Our results provide insight into grass xylan synthesis and how substitutions may be modified for increased saccharification for biofuel generation.

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“…Ferulic acids have been found in the cell walls of many plant products including maize bran, 1) sugar cane bagasse, 2) wheat bran, 3) sugar beet pulp, 4,5) and spinach. 6) In the three former tissues, ferulic acid is esterified to the C 5 of arabinose in arabinoxylan, a 1,4 D xylan to which L arabinofuranosyl residues are attached at position 2 or 3.…”

mentioning

confidence: 99%

Efficient Extraction of Ferulic Acid from Sugar Beet Pulp Using the Culture Supernatant of Penicillium chrysogenum

et al. 2005

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Ferulic acids have been found in the cell walls of many plant products including maize bran, 1) sugar cane bagasse,2) wheat bran, 3) sugar beet pulp, 4,5) and spinach. 6) In the three former tissues, ferulic acid is esterified to the C 5 of arabinose in arabinoxylan, a 1,4 D xylan to which L arabinofuranosyl residues are attached at position 2 or 3. In contrast, ferulic acids mainly attach to the C 2 position of 1,5 linked arabinofuranose residues or the C 6 of 1,4 linked galactopyranose residues in the hairy region of pectins of sugar beet and spinach. 7,8) Recently, Levigne et al. demonstrated that ferulic acid is also linked to the C 5 position of arabinofuranose residues in sugar beet pectin by analysis of the structures of feruloylated oligosaccharides obtained by treating sugar beets with a commercial enzyme preparation (Driselase). 9) Furthermore, some ferulic acids exist as dehydrodimers (e.g. 5 5 dehydrodiferulic acid) in the cell walls of several plant species, which are formed through an oxidation reaction catalyzed by peroxidases.10,11) Possible roles of ferulic acid in plant cell walls are to decrease the digestibility of the cell wall by microorganisms 12) and to regulate cell growth 13) by cross linking cell wall polysaccharides.Ferulic acid esterases (FAEs) are enzymes that catalyze the hydrolysis of ester linkages between ferulic acids and sugars or alcohols. The number of studies concerning microbial FAEs has been increasing in the last ten years and many FAEs have been isolated and characterized. In the utilization of agro industrial wastes such as sugar beet pulp, effective degradation of plant cell walls requires FAEs for the release of ferulic acid as well as polysaccharidases such as xylanases 14) and arabinanases. 15) Moreover, ferulic acid has several potential applications: it may be useful as an anti oxidizing agent, 16,17) an anti inflammatory drug, 18,19) and a food preservative that inhibits microbial growth. 20,21) Enzymatic extraction of ferulic acid from industrial wastes has been studied. Penicillium funiculosum FAEB releases 98% of esterified ferulic acid from wheat bran in the presence of xylanase and releases 35% of esterified ferulic acid from sugar beet pulp in the presence of a mixture of endo arabinanase and L arabinofuranosidase. 22) To the best of our knowledge, that releases more ferulic acid from sugar beet pulp than any other enzyme.In this paper we describe the screening of microorganisms that can achieve high yield extraction of free ferulic acid from sugar beet pulp. In addition, we describe the isolation and some of the characteristics of a novel FAE, termed FAE 1, produced by P. chrysogenum 31B. MATERIALS AND METHODS Chemicals and reagents.ResourceQ 6 mL, ResourceS 6 mL, MonoQ HR 5 5, MonoS HR 5 5 and HiLoad 16 60 Superdex 75 columns were purchased from Amersham Biosciences. All other chemicals were from Wako Pure Chemical Industries, Ltd. (Osaka) unless otherwise stated, and were of certified reagent grade.Organism and cultivation conditions. The microorganisms...

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Isolation and partial characterization of feruloylated oligosaccharides from maize bran

Cited by 286 publications

References 24 publications

Identification of a disaccharide side chain 2-O-α-D-galactopyranosyl-α-D-glucuronic acid inArabidopsisxylan

Identification of a disaccharide side chain 2-O-α-D-galactopyranosyl-α-D-glucuronic acid inArabidopsisxylan

XAX1 from glycosyltransferase family 61 mediates xylosyltransfer to rice xylan

Efficient Extraction of Ferulic Acid from Sugar Beet Pulp Using the Culture Supernatant of Penicillium chrysogenum

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