Structure-antioxidant activity relationships of flavonoids: a re-examination

Free Radic Res. 2002 Nov;36(11):1219-27. doi: 10.1080/198-1071576021000016472.

Abstract

The antioxidant and prooxidant activities of flavonoids belonging to several classes were studied to establish their structure-activity relationships against different oxidants. Special attention was paid to the flavonoids quercetin (flavone), taxifolin (flavanone) and catechin (flavanol), which possess different basic structures but the same hydroxylation pattern (3,5,7,3'4'-OH). It was found that these three flavonoids exhibited comparable antioxidant activities against different oxidants leading to the conclusion that the presence of ortho-catechol group (3',4'-OH) in the B-ring is determinant for a high antioxidant capacity. The flavone kaempferol (3,5,7,4'-OH), however, in spite of bearing no catechol group, also presents a high antioxidant activity against some oxidants. This fact can be attributed to the presence of both 2,3-double bond and the 3-hydroxyl group, meaning that the basic structure of flavonoids becomes important when the antioxidant activity of B-ring is small.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amidines / metabolism
  • Antioxidants / pharmacology*
  • Ascorbic Acid / pharmacology
  • Biphenyl Compounds
  • Catechin / pharmacology*
  • Edetic Acid / pharmacology
  • Flavonoids / pharmacology
  • Flavonols
  • Free Radicals / metabolism
  • Iron / pharmacology
  • Kaempferols*
  • Liposomes / metabolism
  • Metmyoglobin / metabolism
  • Picrates / metabolism
  • Quercetin / analogs & derivatives*
  • Quercetin / pharmacology*
  • Structure-Activity Relationship

Substances

  • Amidines
  • Antioxidants
  • Biphenyl Compounds
  • Flavonoids
  • Flavonols
  • Free Radicals
  • Kaempferols
  • Liposomes
  • Picrates
  • Metmyoglobin
  • kaempferol
  • 2,2'-azobis(2-amidinopropane)
  • Catechin
  • Edetic Acid
  • Quercetin
  • taxifolin
  • 1,1-diphenyl-2-picrylhydrazyl
  • Iron
  • Ascorbic Acid