Purification and molecular structure of two digalactosyl D-chiro-inositols and two trigalactosyl D-chiro-inositols from buckwheat seeds

Carbohydr Res. 2001 Mar 9;331(1):19-25. doi: 10.1016/s0008-6215(00)00320-7.

Abstract

Two digalactosyl D-chiro-inositols and two trigalactosyl D-chiro-inositols, members of the fagopyritol A series and fagopyritol B series, were isolated from buckwheat (Fagopyrum esculentum Moench) seeds. Structures of the first three were determined by 1H and 13C NMR. Fagopyritol B2 is alpha-D-galactopyranosyl-(1-->6)-alpha-D-galactopyranosyl-(1-->2) -1D-chiro-inositol, and fagopyritol A2 is alpha-D-galactopyranosyl-(1-->6)-alpha-D-galactopyranosyl-(1-->3)- 1D-chiro-inositol. Fagopyritol A3, a trigalactosyl D-chiro-inositol, is alpha-D-galactopyranosyl-(1-->6)-alpha-D-galactopyranosyl-(1 -->6) -alpha-D-galactopyranosyl-(1-->3)- 1 D-chiro-inositol. From analysis of hydrolysis products, the second trigalactosyl D-chiro-inositol, fagopyritol B3, isalpha-D-galactopyranosyl-(1-->6)-alpha-D-galactopyranosyl-(1-->6) -alpha-D-galactopyranosyl-(1-->2)-1D-chiro-inositol.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Carbohydrate Conformation
  • Carbohydrate Sequence
  • Disaccharides / chemistry*
  • Disaccharides / isolation & purification
  • Fagopyrum / chemistry*
  • Indicators and Reagents
  • Inositol / analogs & derivatives*
  • Inositol / chemistry*
  • Inositol / isolation & purification
  • Models, Molecular
  • Molecular Sequence Data
  • Nuclear Magnetic Resonance, Biomolecular
  • Oligosaccharides / chemistry*
  • Seeds / chemistry*

Substances

  • Disaccharides
  • Indicators and Reagents
  • Oligosaccharides
  • fagopyritol A1
  • fagopyritol B1
  • Inositol