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 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.
Rezk
Bashir M
BM
Department of Pharmacology and Toxicology, Faculty of Medicine, Universiteit Maastricht P.O. Box 616, 6200 MD Maastricht, The Netherlands.
Haenen
Guido R M M
GR
van der Vijgh
Wim J F
WJ
Bast
Aalt
A
D000098:Acetophenones / Q000737:chemistry / Q000494:pharmacology; D000975:Antioxidants / Q000737:chemistry / Q000494:pharmacology*; D002599:Chalcone / Q000031:analogs & derivatives* / Q000737:chemistry / Q000494:pharmacology; D047188:Chalcones; D005419:Flavonoids / Q000737:chemistry / Q000494:pharmacology; D016166:Free Radical Scavengers / Q000737:chemistry / Q000494:pharmacology; D020128:Inhibitory Concentration 50; D015227:Lipid Peroxidation / Q000187:drug effects; D008956:Models, Chemical; D030421:Peroxynitrous Acid / Q000378:metabolism; D010693:Phloretin / Q000737:chemistry / Q000494:pharmacology*; D010695:Phlorhizin / Q000737:chemistry / Q000494:pharmacology
D000098:Acetophenones; D000975:Antioxidants; D047188:Chalcones; D005419:Flavonoids; D016166:Free Radical Scavengers; D030421:Peroxynitrous Acid; D002599:Chalcone; C019339:2,6-dihydroxyacetophenone; D010695:Phlorhizin; C015812:dihydrochalcone; D010693:Phloretin