Molecular structure of fagopyritol A1 (O-alpha-D-galactopyranosyl-(1 --> 3)-D-chiro-inositol) by NMR.

The molecular structure of fagopyritol A1, a novel galactopyranosyl cyclitol from buckwheat seeds, was determined to be O-alpha-D-galactopyranosyl-(1 --> 3)-D-chiro-inositol by 1H and 13C NMR. Fagopyritol A1 is a positional isomer of fagopyritol B1 (O-alpha-D-galactopyranosyl-(1 --> 2)-D-chiro-inositol), representing a different series of fagopyritol oligomers. Trimethylsilyl derivatives of both compounds have similar mass spectra, but each may be identified by different abundance ratios of fragments with m/z 305/318 and 318/319.