Isolation and structural elucidation of some glycosides from the rhizomes of smaller galanga (Alpinia officinarum Hance)

J Agric Food Chem. 2002 Aug 14;50(17):4919-24. doi: 10.1021/jf025529p.

Abstract

Glycosidically bound compounds were isolated from the methanol extract of fresh rhizomes of smaller galanga (Alpinia officinarum Hance). Nine glycosides (1-9) were finally obtained by reversed-phase HPLC and their structures were elucidated by MS and NMR analyses. They were the three known glycosides, (1R,3S,4S)-trans-3-hydroxy-1,8-cineole beta-D-glucopyranoside (1), benzyl beta-D-glucopyranoside (3), and 1-O-beta-D-glucopyranosyl-4-allylbenzene (chavicol beta-D-glucopyranoside, 4); and the six novel glycosides, 3-methyl-but-2-en-1-yl beta-D-glucopyranoside (2), 1-hydroxy-2-O-beta-D-glucopyranosyl-4-allylbenzene (5), 1-O-beta-D-glucopyranosyl-2-hydroxy-4-allylbenzene (demethyleugenol beta-D-glucopyranoside, 6), 1-O-(6-O-alpha-L-rhamnopyranosyl-beta-D-glucopyranosyl)-2-hydroxy-4-allylbenzene (demethyleugenol beta-rutinoside, 7), 1-O-(6-O-alpha-L-rhamnopyranosyl-beta-D-glucopyranosyl)-4-allylbenzene (chavicol beta-rutinoside, 8), and 1,2-di-O-beta-D-glucopyranosyl-4-allylbenzene (9). Compounds 2-9 were detected for the first time as constituents of galanga rhizomes.

MeSH terms

  • Carbohydrate Conformation
  • Chromatography, High Pressure Liquid
  • Glycosides / chemistry*
  • Glycosides / isolation & purification*
  • Magnetic Resonance Spectroscopy
  • Mass Spectrometry
  • Molecular Structure
  • Plant Extracts / chemistry
  • Rhizome / chemistry*
  • Zingiberaceae / chemistry*

Substances

  • Glycosides
  • Plant Extracts