The antioxidant activity of phloretin: the disclosure of a new antioxidant pharmacophore in flavonoids

  • Biochem Biophys Res Commun. 2002 Jul 5;295(1):9-13. doi: 10.1016/s0006-291x(02)00618-6.
Bashir M Rezk  1 ,  Guido R M M Haenen ,  Wim J F van der Vijgh ,  Aalt Bast
Affiliations
  • 1. Department of Pharmacology and Toxicology, Faculty of Medicine, Universiteit Maastricht P.O. Box 616, 6200 MD Maastricht, The Netherlands.
PMID: 12083758 DOI: 10.1016/s0006-291x(02)00618-6
Abstract

Phloretin is a dihydrochalcone flavonoid that displays a potent antioxidant activity in peroxynitrite scavenging and the inhibition of lipid peroxidation. Comparison with structurally related compounds revealed that the antioxidant pharmacophore of phloretin is 2,6-dihydroxyacetophenone. The potent activity of 2,6-dihydroxyacetophenone is due to stabilisation of its radical via tautomerisation. The antioxidant pharmacophore in the dihydrochalcone phloretin, i.e., the 2,6-dihydroxyacetophenone group, is different from the antioxidant pharmacophores previously reported in Flavonoids.

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