Isolation and partial characterization of feruloylated oligosaccharides from maize bran.
Maize bran contains phenolic acids [approximately 4% dry matter; mainly ferulic acid (Fe) and also diferulic acid], heteroxylans (approximately 50%), and cellulose (approximately 20%), but is devoid of lignin. Treatment of maize pericarp with 0.05 M trifluoroacetic acid at 100 degrees C for 2 h released approximately 90% of the heteroxylans and approximately 90% of the ferulic acid and its esters. After fractionation of the products with Amberlite XAD-2 and Sephadex LH-20 three main feruloylated oligosaccharides (F3-F7) were isolated. They represented approximately 30% of the ferulic acid, and approximately 2% of the neutral sugars contained in the hydrolysis supernatant. The compositions of F7, F6, and F3 were Fe-Ara (1:1), Fe-Ara-Xyl (1:1:1), and Fe-Ara-Xyl-Gal (1:1:1:1), respectively. The structures of the three oligomers were determined using chemical methods (methylation, acetalation, reduction) and 13C NMR spectroscopy: F7 was 5-O-(trans-feruloyl)-L-Araf;F6 was O-beta-D-Xyl p-(1-->2)-[5-O-(trans-feruloyl)-L-Araf]; and F3 was O-L-Gal p-(1-->4)-O-D-Xyl p-(1-->2)-[5-O-(trans-feruloyl)-L- Araf]. F7 has been previously isolated from other monocots especially from wheat bran and soluble arabinoxylans from wheat flour; this is the first report of feruloylated oligosaccharides F6 and F3. Our results suggest that these oligomers are side-chain constituents of heteroxylans in maize bran. Ferulic acid is probably partly responsible for the insolubility of heteroxylans by coupling polysaccharide chains through ferulic acid dimers.
D000107:Acetylation; D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D002850:Chromatography, Gel; D002852:Chromatography, Ion Exchange; D003373:Coumaric Acids / Q000032:analysis*; D006868:Hydrolysis; D062385:Hydroxybenzoates; D009682:Magnetic Resonance Spectroscopy; D008745:Methylation; D008969:Molecular Sequence Data; D009005:Monosaccharides / Q000032:analysis; D009844:Oligosaccharides / Q000737:chemistry* / Q000302:isolation & purification; D014269:Trifluoroacetic Acid; D014990:Xylans / Q000737:chemistry* / Q000302:isolation & purification; D003313:Zea mays / Q000737:chemistry*
D003373:Coumaric Acids; D062385:Hydroxybenzoates; D009005:Monosaccharides; D009844:Oligosaccharides; D014990:Xylans; C004999:ferulic acid; D014269:Trifluoroacetic Acid