Characterisation by 1H NMR spectroscopy of enzymically derived oligosaccharides from alkali-extractable wheat-flour arabinoxylan

Gruppen, Harry; Hoffmaann, Rainer A.; Kormelink, F.J.M.; Voragen, A.G.J.; Kamerlin, Johannis P.; Vliegenthart, Johannes F.G.

doi:10.1016/s0008-6215(00)90919-4

Cited by 124 publications

(61 citation statements)

References 17 publications

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“…The signals obtained form 13 C and 1 H NMR are assigned by comparing with previously reported data (Hoffmann et al 1991;Gruppen et al 1992Gruppen et al , 1993 WO-IV: In 13 C NMR the anomeric carbons of β-xylopyranoside gave signals at δ 96.2 ppm and δ 101.5 ppm which are assigned to reducing β-xylopyranoside and nonreducing β-xylopyranoside respectively and the resonance in the region of δ 107.3 is assigned to the anomeric carbon atoms of α-L-arabinofuranoside. The α-L-arabinofuranoside linked to O-3 of the second β-xylopyranoside from the reducing end position were characterized by the signals δ 107.3 ppm (C1), δ 80.4 ppm (C2), δ 76.9 ppm (C3), δ 84.5 ppm (C4) and δ 61.0 ppm (C5) respectively (Table 3).…”

Section: Nmr Spectramentioning

confidence: 56%

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Antioxidant property of synbiotic combination of Lactobacillus sp. and wheat bran xylo-oligosaccharides

Lasrado

Muralikrishna

2014

J Food Sci Technol

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Wheat bran water unextractable portion (WB-WUP) was subjected to xylanase treatment to obtain a mixture of xylo-oligosaccharides (XOS). XOS mixture was purified on charcoal-celite column and the individual oligosaccharides were separated on a Bio-Gel P-2 column. The sugar composition of the purified oligosaccharides was determined by GLC and their structure was deduced by ESI-MS and 1 H and 13 C NMR. The major oligosaccharides identified were xylobiose and xylotriose (consisting of arabinose). Five strains of lactobacilli (probiotics), XOS (prebiotics) and a combination of both (synbiotics) in milk (as medium) were monitored for antioxidant activity. DPPH radical scavenging activity (~70 %) as well as ferric reducing power (~80 mg/ 100 ml FeSO 4 eq) were significantly higher (p<0.05) in all the synbiotic preparations compared to that of control. The present study indicated that the synbiotic preparations consisting of XOS and lactobacilli can be effectively used as dietary supplement.

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Section: Nmr Spectramentioning

confidence: 56%

“…The 1 H NMR spectrum signal around δ 5.30 ppm (H1), δ 4.15 ppm (H2). δ 3.92 ppm (H3), δ 4.30 ppm(H4) and δ 3.80 ppm (H5) indicated that arabinofuranoside residue is linked to the O-3 position of the second β-xylopyranose residue (Gruppen et al 1992).…”

Section: Nmr Spectramentioning

confidence: 99%

Antioxidant property of synbiotic combination of Lactobacillus sp. and wheat bran xylo-oligosaccharides

Lasrado

Muralikrishna

2014

J Food Sci Technol

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“…Arabinoxylan oligosaccharide 6.1, isolated from arabinoxylan hydrolyzates according to Gruppen et al [33] and used as a substrate for the B. adolescentis AXH-d, was a gift from Ms. Katrien Van Laere of this laboratory. All other substrates used were from sources previously specified [22].…”

Section: Substrates and Other Chemicalsmentioning

confidence: 99%

Stereochemical course of hydrolysis catalyzed by arabinofuranosyl hydrolases

Pitson¹,

Voragen²,

Beldman³

1996

FEBS Letters

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1~ IntroductionEnzymic hydrolysis of glycosidic linkages occurs via two m ~jor mechanisms, which result in either net retention or inversion of anomeric configuration [1]. Both hydrolytic mechmisms involve general acid catalysis and require two critical reddues (a proton donor and a nucleophile/base), which in m 9st glycosyl hydrolases are aspartate and/or glutamate resid~es 2.1.99)hydrolyse the (1 ~ 5)-C~-L-arabinofuranosyl linkages in linear arabinan in a random pattern, initially releasing arabinotriose and larger arabino-oligosaccharides as the major hydrolysis products [22]. In contrast, C~-L-arabinofuranosidases (a-L-arabinofuranoside arabinofuranohydrolase, EC 3.2.1.55) hydrolyse nonreducing C~-L-arabinofuranosyl residues from arabinofuranosecontaining substrates, releasing arabinose as the only hydrolysis product [21]. Two major types of C~-L-arabinofuranosidases can be classified according to substrate specificity, and are typified by the two enzymes isolated from Aspergillus niger [21,24]. Arabinofuranosidase A is only active against small substrates, like 4-nitrophenyl a-L-arabinofuranoside (pNPA) and short-chain arabino-oligosaccharides, while arabinofuranosidase B has similar activity on these substrates, but is also able to hydrolyse polymeric substrates like branched arabinan and arabinoxylan. Recently, other enzymes have been isolated [25,26] that are specific for arabinofuranosyl residues in arabinoxylan, and are termed arabinoxylan arabinohydrolases ((1 ~4)-[3-D-arabinoxylan arabinofuranohydrolase, EC 3.2.1.) (AXH). The AXH from Aspergillus awamori has been studied in some detail [23,25,27] and found to only cleave arabinofuranose from single-substituted xylopyranosyl residues in the xylan backbone, and has only low activity against substrates like pNPA or branched arabinan. Similar enzymes from B/fidobacterium adolescentis [26] and Trichoderma reesei (R. Kavitha, H. Gruppen and A.G.J. Voragen, unpublished) have also been recently isolated that appear to have a slightly different specificity since they are active against arabinofuranosyl groups linked to double-substituted xylopyranosyl residues, and are therefore termed AXH-d.Apart from studies with the c~-e-arabinofuranosidases from Monilinia fructigena [28,29], there has been little work examining the mechanisms by which these enzymes cleave arabinofuranosyl linkages. In this current study the stereochemical course of hydrolysis catalyzed by endo-(l ~5)-Ot-L-arabina-

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“…Its structure was recently intensively studied using 'H-NMR spectroscopy and methylation analysis (Hoffmann et al, 1991(Hoffmann et al, , 1992a(Hoffmann et al, , 1992bGruppen, 1992aGruppen, , 1992bGruppen, , 1993Cleemput et al, 1993Cleemput et al, , 1995a.…”

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confidence: 99%

Identification and Characterization of a Novel Arabinoxylanase from Wheat Flour

et al. 1997

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An endogenous wheat (Triticum aestivum) flour endoxylanase was purified t o homogeneity from a crude wheat flour extract by ammonium sulfate precipitation and cation-exchange chromatography. The 30-kD protein had an isoelectric point of 9.3 or higher. A sequence of 19 amino acids at the NH, terminus showed 84.2% identity with an interna1 sequence of the 15-kD grain-softness protein, friabilin. High-performance anion-exchange chromatography and gel-permeation analysis of the hydrolysis products indicated the preferential hydrolysis of highly branched structures by the enzyme; wheat arabinoxylan and rye (Secale cereale) arabinoxylan (high arabinose to xylose ratios) were hydrolyzed more efficiently by this enzyme than oat (Avena safiva) spelt xylan (low arabinose to xylose ratios). The release of the hydrolysis products as a function of time suggested that the endoxylanolytic activity was associated with the release of arabinose units from the polysaccharides, suggesting that the enzyme action i s similar to that by endoxylanases from Ceratocystis paradoxa, Aspergillus niger, and Neurospora crassa. Although the enzyme released arabinose from arabinoxylan, it did not hydrolyze pnitrophenyl-a-i-arabinofuranoside. From the above, it follows that the enzyme, called arabinoxylanase, differs from most microbial endoxylanases and from an endoxylanase purified earlier from wheat flour.AX, the main NSP in wheat (Triticum uestivum) endosperm, consists of a linear backbone of 1P-linked 6-Dxylopyranose units with L-arabinofuranosyl residues attached to the main chain by 1,3-and/or 1,2-cu-glycosidic linkages. Its structure was recently intensively studied using 'H-NMR spectroscopy and methylation analysis (Hoffmann et al., 1991(Hoffmann et al., , 1992a(Hoffmann et al., , 1992bGruppen, 1992aGruppen, , 1992bGruppen, , 1993Cleemput et al., 1993Cleemput et al., , 1995a.NSP-hydrolyzing enzymes are found in wheat grain (Preece and MacDougall, 1958;Kulp, 1968;Lee and Ronalds, 1972;Schmitz et al., 1974;Bremen, 1981; Adlung, 1985;Moore and Hoseney, 1990), in germinated wheat and wheat bran (Beldman et al., 1996), in barley (Hordeum vulgure) aleurone layers (Taiz and Honigman, 1976;Dashek

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Characterisation by 1H NMR spectroscopy of enzymically derived oligosaccharides from alkali-extractable wheat-flour arabinoxylan

Cited by 124 publications

References 17 publications

Antioxidant property of synbiotic combination of Lactobacillus sp. and wheat bran xylo-oligosaccharides

Antioxidant property of synbiotic combination of Lactobacillus sp. and wheat bran xylo-oligosaccharides

Stereochemical course of hydrolysis catalyzed by arabinofuranosyl hydrolases

Identification and Characterization of a Novel Arabinoxylanase from Wheat Flour

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