Antioxidative activities of galloyl glucopyranosides from the stem-bark of Juglans mandshurica

Biosci Biotechnol Biochem. 2008 Aug;72(8):2158-63. doi: 10.1271/bbb.80222. Epub 2008 Aug 7.

Abstract

Two phenolics, 1,2,6-trigalloylglucose (1) and 1,2,3,6-tetragalloylglucose (2), isolated from the stem-bark of Juglans mandshurica were evaluated for their antioxidative activities. The results showed that compounds 1 and 2 exhibited strong scavenging activities against 1,1'-diphenyl-1-picrylhydrazyl (DPPH), 2,2'-azino-bis-(3-ethylbenzenthiazoline-6-sulphonic) acid (ABTS(*+)), and superoxide radicals (O(2)(*-)), and also had a significant inhibitory effect on lipid peroxidation and low-density lipoprotein (LDL) oxidation. The strong superoxide radical scavenging of 1 and 2 resulted from the potential competitive inhibition with xanthine at the active site of xanthine oxidase (OX). In addition, compounds 1 and 2 displayed significant lipoxygenase inhibitory activity, the mode of inhibition also being identified as competitive. In comparison, the antioxidative activities of compounds 1 and 2, together with gallic acid, indicated that the number of galloyl moieties could play an important role in the antioxidative activity.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antioxidants / chemistry*
  • Antioxidants / pharmacology*
  • Enzyme Inhibitors / chemistry
  • Enzyme Inhibitors / pharmacology
  • Glucosides / chemistry*
  • Glucosides / isolation & purification
  • Glucosides / pharmacology*
  • Glycine max / enzymology
  • Humans
  • Juglans / chemistry*
  • Lipid Peroxidation / drug effects
  • Lipoxygenase / metabolism
  • Molecular Structure
  • Plant Bark / chemistry*
  • Substrate Specificity
  • Xanthine Oxidase / antagonists & inhibitors
  • Xanthine Oxidase / metabolism

Substances

  • Antioxidants
  • Enzyme Inhibitors
  • Glucosides
  • Lipoxygenase
  • Xanthine Oxidase