The inhibitory effect of luteolin-7-O-glucoside on the formation of pentyl and 7-carboxyheptyl radicals from 13-hydroperoxy-9,11-octadecadienoic acid in the presence of iron(II) ions

Free Radic Res. 2004 Aug;38(8):869-76. doi: 10.1080/10715760410001722033.

Abstract

A flavone glucoside, luteolin-7-O-glucoside (luteolin-7-G) inhibited the formation of pentyl and 7-carboxyheptyl radicals in the reaction of 13-hydroperoxy-9,11-octadecadienoic (13-HPODE) acid with iron(II) ions. The inhibitory effect of luteolin-7-G was diminished in the presence of EDTA. These results indicated that the inhibitory effects of luteolin-7-G occur partly through the chelation of iron ions. Measurement of visible spectra also showed that luteolin-7-G chelates iron ions. On the other hand, luteolin-7-G did not inhibit the reaction under anaerobic conditions, suggesting that oxygen molecules participate in the inhibition. Oxygen consumption measurements showed that the luteolin-7-G/iron ion complexes react with oxygen molecules in competition with 13-HPODE acid, and free iron ions exclusively react with 13-HPODE acid. The reaction of luteolin-7-G/iron ion complexes with oxygen molecules possibly diminishes the formation of pentyl and 7-carboxyheptyl radicals.

MeSH terms

  • Chromatography, High Pressure Liquid
  • Fatty Acids, Unsaturated / chemistry
  • Free Radicals / chemistry*
  • Glucosides / chemistry*
  • Glucosides / pharmacology
  • Iron / chemistry*
  • Iron / pharmacology
  • Linoleic Acids / chemistry*
  • Lipid Peroxides / chemistry*
  • Luteolin / chemistry*
  • Luteolin / pharmacology
  • Molecular Structure
  • Oxygen / chemistry
  • Spectrum Analysis

Substances

  • 13-oxotrideca-9,11-dienoic acid
  • Fatty Acids, Unsaturated
  • Free Radicals
  • Glucosides
  • Linoleic Acids
  • Lipid Peroxides
  • 13-hydroperoxy-9,11-octadecadienoic acid
  • luteolin-7-glucoside
  • Iron
  • Luteolin
  • Oxygen