The antioxidant activity of phloretin: the disclosure of a new antioxidant pharmacophore in flavonoids |
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Authors: | Rezk Bashir M Haenen Guido R M M van der Vijgh Wim J F Bast Aalt |
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Affiliation: | Department of Pharmacology and Toxicology, Faculty of Medicine, Universiteit Maastricht P.O. Box 616, 6200 MD Maastricht, The Netherlands. |
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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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Keywords: | Phloretin Dihydrochalcone Flavonoid Peroxynitrite Lipid peroxidation |
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