The Scavenging of DPPH, Galvinoxyl and ABTS Radicals by Imine Analogs of Resveratrol

Molecules. 2016 Jan 21;21(1):E127. doi: 10.3390/molecules21010127.

Abstract

Resveratrol (3,5,4'-trihydroxystilbene) is a phytoalexin produced by plants. Resveratrol is known for its anti-cancer, antiviral and antioxidant properties. We prepared imine analogs of resveratrol ((hydroxyphenyliminomethyl)phenols) and tested their antioxidant activity. All prepared resveratrol analogs were able to scavenge 2,2-diphenyl-1-picrylhydrazyl (DPPH), galvinoxyl radical (GOR) and 2,2'-azino-bis(3-ethylbenzothiazoline)-6-sulphonic acid (ABTS) radicals. The antioxidant activity efficiency correlated with the number and position of hydroxyl groups. The most effective antioxidants were resveratrol analogs containing three hydroxyl groups in the benzylidene part of their molecules. These results provide new insights into the relationship between the chemical structure and biological activity of resveratrol analogs.

Keywords: antioxidant activity; iminophenols; resveratrol analogs.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Benzhydryl Compounds / antagonists & inhibitors*
  • Benzothiazoles / antagonists & inhibitors*
  • Biphenyl Compounds / antagonists & inhibitors*
  • Free Radical Scavengers / chemistry*
  • Free Radical Scavengers / pharmacology*
  • Molecular Structure
  • Picrates / antagonists & inhibitors*
  • Resveratrol
  • Stilbenes / chemistry*
  • Stilbenes / pharmacology*
  • Sulfonic Acids / antagonists & inhibitors*

Substances

  • Benzhydryl Compounds
  • Benzothiazoles
  • Biphenyl Compounds
  • Free Radical Scavengers
  • Picrates
  • Stilbenes
  • Sulfonic Acids
  • 2,2'-azino-di-(3-ethylbenzothiazoline)-6-sulfonic acid
  • 1,1-diphenyl-2-picrylhydrazyl
  • Resveratrol
  • galvinoxyl