Antioxidant properties of hydroxy-flavones.
The antioxidant properties of 24 hydroxy-flavones were evaluated. Results show that 2',3',4'-OH substitution on the B ring plays a crucial role in radical scavenger activity in the DPPH assay and in the inhibitory effect on pereoxydation of tissue lipids in the MDA test. The formation of stable radicals for this type of compounds has been studied by ESR. In addition, it has been found that 7-hydroxy-flavones are potent competitive inhibitors of xanthine oxidase. It is proposed that the C-7 OH of flavones may take the place of the C-2 or C-6 OH of xanthine in the active site of the enzyme. A C-4' OH or C-4' OMe substitution on the 7-hydroxy flavones is not favourable to a fit in the active site. The 2',3',4'-trihydroxy-flavones inhibited XO by another process, which remains to be determined. In summary, this study provides evidence that hydroxy-flavones exhibit interesting antioxidant properties expressed either by the capacity to scavenge free radicals (for 2',3',4'-trihydroxy-flavones) or to competitively inhibit xanthine oxidase (for 7-hydroxy-flavones). These compounds may be drug candidates for treating pathologies related to free radical oxidation.
Laboratoire de Chimie Organique Physique, Villeneuve d'Ascq. Cedex, France.
N
N
Cotelle
J L
JL
Bernier
J P
JP
Catteau
J
J
Pommery
J C
JC
Wallet
E M
EM
Gaydou
D000975:Antioxidants / Q000378:metabolism / Q000494:pharmacology*; D016227:Benzoquinones / Q000737:chemistry / Q000378:metabolism; D015764:Bepridil / Q000031:analogs & derivatives / Q000378:metabolism; D001665:Binding Sites; D001713:Biphenyl Compounds; D004578:Electron Spin Resonance Spectroscopy; D005419:Flavonoids / Q000737:chemistry / Q000378:metabolism / Q000494:pharmacology*; D016166:Free Radical Scavengers / Q000378:metabolism / Q000494:pharmacology*; D005609:Free Radicals / Q000378:metabolism; D007700:Kinetics; D015227:Lipid Peroxidation / Q000187:drug effects; D008163:Luminescent Measurements; D015394:Molecular Structure; D010851:Picrates; D013056:Spectrophotometry, Ultraviolet; D017392:Thiobarbituric Acid Reactive Substances; D014969:Xanthine Oxidase / Q000037:antagonists & inhibitors / Q000378:metabolism
D000975:Antioxidants; D016227:Benzoquinones; D001713:Biphenyl Compounds; D005419:Flavonoids; D016166:Free Radical Scavengers; D005609:Free Radicals; D010851:Picrates; D017392:Thiobarbituric Acid Reactive Substances; C025232:semiquinone radicals; D015764:Bepridil; C004931:1,1-diphenyl-2-picrylhydrazyl; D014969:Xanthine Oxidase