Structural studies of an arabinoxylan isolated from the leaves of neolitsea cassia

doi:10.1016/S0008-6215(00)90302-1

Carbohydrate Research

Volume 152, 1 September 1986, Pages 229-236

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Abstract

A water-soluble arabinoxylan giving highly viscous solutions was isolated from the leaves of Neolitsea cassia (L.). The molar ratio of d-xylose to l-arabinose was 1:2.7, but small proportions of other sugars were also present. Linkage analysis, partial acid hydrolysis, and ¹H- and ¹³C-n.m.r. spectroscopy revealed that the polysaccharide was highly branched with a backbone of (1→4)-linked β-d-xylopyranosyl residues each of which was substituted at both O-2 and O-3 with short side-chains composed of terminal α- and β-l-arabinofuranosyl groups and (1→3)-linked α-l-arabinofuranosyl residues.

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Citation Excerpt :
Neolitsea, a member of the family Lauraceae is an evergreen shrub which comprises of approximately 100 species especially in tropical regions of Asia particularly in the East, South and Southwest China (Cao et al., 2015; Wang et al., 2014). Few species from this genus such as N. cambodiana (leaves) are applied externally to treat furuncles and carbuncles; the barks and roots of N. aurata have been used to alleviate edema by inducing diuresis (Wang et al., 2014); and the barks and leaves of N. cassia are used in treating fractures (de Silva et al., 1986). Apart from essential oils, Neolitsea species also rich in alkaloids and terpenoids as well as flavonoids, ferulates, lignans, benzoids and paraquinones (Cao et al., 2015; Wang et al., 2014).
Two new β-carboline alkaloids, daibucarbolines D (1) and E (2) and one new sesquiterpene dilactone, pseudovillosine (3), together with five known compounds, taraxerone, taraxerol, pseudoneoliacine, daibucarboline A and linderaggrine A were isolated from the stems of Neolitsea kedahensis (Lauraceae). The structures were confirmed through extensive spectroscopic analysis, while the relative configuration of compound (3) was determined by a single crystal X-ray diffraction.
A water-soluble polysaccharide from the leaves of Litsea gardneri (Lauraceae)
1995, Carbohydrate Polymers
A neutral polysaccharide isolated from the water extract of the leaves of Litsea gardneri was composed mainly of xylose (70%) and small, approximately equimolar amounts of arabinose, mannose, galactose and glucose. Methylation analysis combined with GLC-MS, ¹[H] and ¹³[C]NMR spectroscopy of the native and degraded polysaccharides indicated the presence of a 1 → 4 linked β-d-xylopyranosyl backbone. It is possible that some arabinofuranosyl residues were incorporated in the backbone of the polymer. Side chains were attached to O-2 of some of the xylopyranosyl residues in the polymer chain. The available evidence suggests that the side chains may be either single units of terminal arabinofuranosyl/xylopyranosyl residues or multiple unit side chains containing both arabinosyl and xylosyl residues.
Mode of action of (1→4)-β-d-arabinoxylan arabinofuranohydrolase (AXH) and |ga=l-arabinofuranosidases on alkali-extractable wheat-flour arabinoxylan
1993, Carbohydrate Research
Arabinoxylan-derived oligosaccharides were treated with (1→4)-β-d-arabinoxylan arabinofuranohydrolase (AXH) and two types of α-l-arabinofuranosidase, A and B. Analysis of reaction products by high performance anion-exchange chromatography indicated the removal of arabinofuranosyl groups from singly substituted xylopyranosyl residues. In addition, differences in the specificity of these enzymes towards the various differently substituted oligosaccharides were observed. ¹H NMR spectroscopy and methylation analysis of alakli-extractable wheat-flour arabinoxylan treated with AXH confirmed the specificity of AXH towards (1→3)-linked arabinofuranosyl groups on singly substituted xylopyranosyl residues. With these techniques, α-l-arabinofuranosidase B was found to cause minor changes in (1→2)- and (1→3)- linked arabinofuranosyl groups on substituted xylopyranosyl residues.
Raw and extruded fibre from pea hulls. Part II: Structural study of the water-soluble polysaccharides
1993, Carbohydrate Polymers
The soluble fraction (9%) obtained by aqueous extraction of an extruded pea hull fibre gave 3 peaks on DEAE-Sepharose-6B. The first population (25%) was not bound to the gel and contained xylose, arabinose and glucose (15:6:1), the second one (12%), eluted for an ionic strength of 0·08 m, contained xylose, arabinose and glucuronic acid (18:1:1), and the third one (63%), eluted for an ionic strength between 0·3 m and 0·8 m, contained galacturonic acid, arabinose, xylose, rhamnose and galactose (5·3:3:1·8:1·7:1). The structure of these fractions was studied through enzymic degradation, methylation, ¹H-NMR and ¹³C-NMR. The first one was composed mainly of a heteroxylan having a (1 → 4)-β-d-xylan backbone (average d.p. 103) with only very few branching points at O-2, and of a slightly branched arabinan. The second one was an acidic xylan. Both heteroxylans were acetylated. The third one was pectic in nature with a main chain consisting of (1 → 4) linked galacturonic acid, partly substituted at the O-2 and O-3 positions, and (1 → 2) linked rhamnose residues which were mainly substituted at the O-4 position. This acidic fraction was appreciably hydrolyzed by an endopolygalacturonase, indicating the presence of homogalacturonan regions in the molecules. Arabinose, galactose and xylose were present as side-chains.
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The major water-soluble arabinoxylan fraction from rye grain, containing 4-linked β-d-xylopyranosyl residues of which about 43% were substituted solely at O-3 and 7% at both O-2 and O-3 with terminal α-l-arabinofuranosyl units, was hydrolysed to different extents using semi-purified xylanase from Trichoderma reesei. Products were fractionated on Biogel P-2 and structurally elucidated by sugar, methylation and high-field ¹H-NMR analysis. Moderate hydrolysis released arabinose, xylose, xylobiose, xylotriose and xylotetraose together with xylo-oligosaccharides (DP ≥ 4) in which one or more of the residues were substituted at O-3 with a terminal arabinose unit. The xylose residues substituted with arabinose units at both O-2 and O-3 became enriched in the remaining polymeric fraction. Extensive hydrolysis with the enzyme released arabinose, xylose and xylobiose as major products together with small amounts of two oligosaccharides and a polymeric fraction. One of the oligosaccharides was identified as xylotriose in which the non-reducing end was substituted at O-2 and O-3 with terminal arabinose units and the other as xylotetraose in which one of the interjacent residues was substituted with arabinose units in the same way. The polymeric fraction contained a main chain of 4-linked xylose residues in which 60–70% of the residues were substituted at both O-2 and O-3 with arabinose units.
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1990, Carbohydrate Research
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Structural studies of an arabinoxylan isolated from the leaves of neolitsea cassia

Abstract

Carbohydr. Res.

Carbohydr. Res.

Carbohydr. Res.

Carbohydr. Res.

Carbohydr. Res.

Carbohydr. Res.

Swed. J. Agric. Rec.