Inhibition of lipid peroxidation and structure-activity-related studies of the dietary constituents anthocyanins, anthocyanidins, and catechins

J Agric Food Chem. 2002 Sep 11;50(19):5308-12. doi: 10.1021/jf025671q.


The antioxidant activities of a series of commonly consumed and biogenetically related plant phenolics, namely, anthocyanidins, anthocyanins, and catechins, in a liposomal model system have been investigated. The antioxidant efficacies of the compounds were evaluated on their abilities to inhibit the fluorescence intensity decay of an extrinsic probe, 3-[p-(6-phenyl)-1,3,5-hexatrienyl]phenylpropionic acid, caused by free radicals generated during metal ion-induced peroxidation. Distinct structure-activity relationships were revealed for the antioxidant abilities of these structurally related compounds. Whereas antioxidant activity increased with an increasing number of hydroxyl substituents present on the B-ring for anthocyanidins, the converse was observed for catechins. However, substitution by methoxyl groups diminished the antioxidant activity of the anthocyanidins. Substitution at position 3 of ring C played a major role in determining the antioxidant activity of these classes of compounds. The anthocyanidins, which possess a hydroxyl group at position 3, demonstrated potent antioxidant activities. For the cyanidins, an increasing number of glycosyl units at position 3 resulted in decreased antioxidant activity. Similarly, the substitution of a galloyl group at position 3 of the flavonoid moiety resulted in significantly decreased antioxidant activity for the catechins. Among catechins, cis-trans isomerism, epimerization, and racemization did not play a role in overall antioxidant activity. The antioxidant activities of test compounds (at 40 microM concentrations) were compared to the commercial antioxidants tert-butylhydroquinone, butylated hydroxytoluene, butylated hydroxyanisole, and vitamin E (all at 10 microM concentrations).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anthocyanins / chemistry
  • Anthocyanins / pharmacology*
  • Antioxidants / chemistry
  • Antioxidants / pharmacology*
  • Catechin / chemistry
  • Catechin / pharmacology*
  • Diet
  • Ferrous Compounds / pharmacology
  • Lipid Peroxidation / drug effects*
  • Molecular Structure
  • Structure-Activity Relationship*
  • Vitamin E / pharmacology


  • Anthocyanins
  • Antioxidants
  • Ferrous Compounds
  • Vitamin E
  • Catechin