Isolation and partial characterization of feruloylated oligosaccharides from maize bran

Carbohydr Res. 1995 Aug 11;272(2):241-53. doi: 10.1016/0008-6215(95)00053-v.

Abstract

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.

MeSH terms

  • Acetylation
  • Carbohydrate Conformation
  • Carbohydrate Sequence
  • Chromatography, Gel
  • Chromatography, Ion Exchange
  • Coumaric Acids / analysis*
  • Hydrolysis
  • Hydroxybenzoates
  • Magnetic Resonance Spectroscopy
  • Methylation
  • Molecular Sequence Data
  • Monosaccharides / analysis
  • Oligosaccharides / chemistry*
  • Oligosaccharides / isolation & purification
  • Trifluoroacetic Acid
  • Xylans / chemistry*
  • Xylans / isolation & purification
  • Zea mays / chemistry*

Substances

  • Coumaric Acids
  • Hydroxybenzoates
  • Monosaccharides
  • Oligosaccharides
  • Xylans
  • ferulic acid
  • Trifluoroacetic Acid