title: The antioxidant activity of phloretin: the disclosure of a new antioxidant pharmacophore in flavonoids.
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.
authors.affiliation: Department of Pharmacology and Toxicology, Faculty of Medicine, Universiteit Maastricht P.O. Box 616, 6200 MD Maastricht, The Netherlands.
authors.forename: Bashir M
authors.initials: BM
authors.lastname: Rezk
authors.forename: Guido R M M
authors.initials: GR
authors.lastname: Haenen
authors.forename: Wim J F
authors.initials: WJ
authors.lastname: van der Vijgh
authors.forename: Aalt
authors.initials: A
authors.lastname: Bast
mesh_terms: 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
chemical_list: 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