Isolation of novel glucosides related to gingerdiol from ginger and their antioxidative activities

J Agric Food Chem. 2000 Feb;48(2):373-7. doi: 10.1021/jf990674x.

Abstract

Two novel glucosides of 6-gingerdiol were isolated from fresh ginger (Zingiber officinale Roscoe). Their structures were determined as 1-(4-O-beta-D-glucopyranosyl-3-methoxyphenyl)-3,5-dihydroxydecane (1) and 5-O-beta-D-glucopyranosyl-3-hydroxy-1-(4-hydroxy-3-methoxyphenyl)deca ne (2) by HRFAB-MS and NMR analyses, and the absolute configurations of both aglycons were identified as (3S,5S) by a comparison with synthetic compounds. After incubating these glucosides with acetone powder prepared from fresh ginger, they were confirmed to have been hydrolyzed to 6-gingerdiol by HPLC. This result suggests that these glucosides are the precursors or intermediates of 6-gingerdiol. To recognize their function, their antioxidative activities were investigated and compared to that of their aglycon, 6-gingerdiol, by a linoleic acid model system and by their DPPH radical-scavenging ability. Although 1 did not indicate any activity, 2 had as strong activity as the aglycon in both measurements.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetone
  • Antioxidants / isolation & purification*
  • Catechols
  • Fatty Alcohols / chemistry*
  • Free Radicals
  • Ginger / chemistry*
  • Glucosides / chemistry*
  • Glucosides / isolation & purification*
  • Linoleic Acid / analysis
  • Plants, Medicinal*

Substances

  • 1-(4-O-glucopyranosyl-3-methoxyphenyl)-3,5-dihydroxydecane
  • 5-O-glucopyranosyl-3-hydroxy-1-(4-hydroxy-3-methoxyphenyl)decane
  • Antioxidants
  • Catechols
  • Fatty Alcohols
  • Free Radicals
  • Glucosides
  • Acetone
  • gingerol
  • Linoleic Acid