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  • Title: Isolation and structural identification of complex feruloylated heteroxylan side-chains from maize bran.
    Author: Allerdings E, Ralph J, Steinhart H, Bunzel M.
    Journal: Phytochemistry; 2006 Jun; 67(12):1276-86. PubMed ID: 16777153.
    Abstract:
    Three complex heteroxylan side-chains acylated with ferulate and one arabinosyl ester of p-coumaric acid have been isolated from maize bran insoluble fibre after acidic hydrolysis and fractionation by gel permeation chromatography and semi-preparative RP-HPLC. The complete structural elucidation of all isolated compounds was achieved by 1D/2D NMR spectroscopy and HPLC-MS in combination with methylation analysis. The absolute configuration of the carbohydrate constituents was determined by chiral GC after acidic hydrolysis and trifluoroacetylation. The identified feruloylated tetrasaccharides alpha-d-xylopyranosyl-(1-->3)-alpha-l-galactopyranosyl-(1-->2)-beta-d-xylopyranosyl-(1-->2)-5-O-trans-feruloyl-l-arabinofuranose (FAXGX) and alpha-d-galactopyranosyl-(1-->3)-alpha-l-galactopyranosyl-(1-->2)-beta-d-xylopyranosyl-(1-->2)-5-O-trans-feruloyl-l-arabinofuranose (FAXGG) are the most complex heteroxylan side-chains from maize bran that have been isolated to date. The isolated trisaccharide alpha-l-galactopyranosyl-(1-->2)-beta-d-xylopyranosyl-(1-->2)-5-O-trans-feruloyl-l-arabinofuranose (FAXG) contributes to the complexity of heteroxylan side-chains from maize bran and 5-O-trans-p-coumaroyl-l-arabinofuranose represents the first p-coumaroylated heteroxylan side-chain isolated from cereal grains. Complex feruloylated heteroxylan side-chains are possibly, like ferulate cross-linking of the heteroxylans and binding of heteroxylans to lignin, a factor contributing to limited enzymatic degradation of fibre.
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