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

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...

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Bibliographic Details
Published in:Biochemical and biophysical research communications 2002-07, Vol.295 (1), p.9-13
Main Authors: Rezk, Bashir M, Haenen, Guido R.M.M, van der Vijgh, Wim J.F, Bast, Aalt
Format: Article
Language:English
Subjects:
Acetophenones - chemistry
Acetophenones - pharmacology
Antioxidants - chemistry
Antioxidants - pharmacology
Chalcone - analogs & derivatives
Chalcone - chemistry
Chalcone - pharmacology
Chalcones
Dihydrochalcone
Flavonoid
Flavonoids - chemistry
Flavonoids - pharmacology
Free Radical Scavengers - chemistry
Free Radical Scavengers - pharmacology
Inhibitory Concentration 50
Lipid peroxidation
Lipid Peroxidation - drug effects
Models, Chemical
Peroxynitrite
Peroxynitrous Acid - metabolism
Phloretin
Phloretin - chemistry
Phloretin - pharmacology
Phlorhizin - chemistry
Phlorhizin - pharmacology
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Summary: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.
ISSN:0006-291X
1090-2104
DOI:10.1016/S0006-291X(02)00618-6