Structure-activity relationship in the ability of flavonols to inhibit chemiluminescence

J Ethnopharmacol. 1994 Jan;41(1-2):121-6. doi: 10.1016/0378-8741(94)90066-3.

Abstract

Fourteen flavonoids were evaluated for their ability to inhibit chemiluminescence, either of neutrophils that had been briefly exposed to both luminol and phorbol-myristate acetate or to an enzymatic system with H2O2, luminol and horseradish peroxidase. Using chemiluminescence as the quantitative parameter, it can be concluded that the hydroxyl group in position 3 of the flavonols is vital for their inhibitory effect, and that two hydroxyl groups on the phenyl ring are optimal for such an effect. It was also noted that the C2-C3 double bond is essential for the flavonols' anti-oxidative effect. It is suggested that the ability of flavonols to suppress chemiluminescence is reciprocally correlated with their lipophilicity.

MeSH terms

  • Animals
  • Antioxidants / chemistry
  • Antioxidants / pharmacology*
  • Flavonoids / chemistry
  • Flavonoids / pharmacology*
  • Flavonols
  • Free Radical Scavengers*
  • Guinea Pigs
  • Horseradish Peroxidase / metabolism
  • Luminescent Measurements
  • Male
  • Neutrophils / drug effects*
  • Neutrophils / metabolism
  • Structure-Activity Relationship

Substances

  • Antioxidants
  • Flavonoids
  • Flavonols
  • Free Radical Scavengers
  • Horseradish Peroxidase