Effects of flavonoids on nonenzymatic lipid peroxidation: structure-activity relationship.
The in vitro effects of several flavonoids on nonenzymatic lipid peroxidation in the rat brain mitochondria was studied. The lipid peroxidation was indexed by measuring the MDA production using the 2-thiobarbituric acid TBA test. The flavonoids, apigenin, flavone, flavanone, hesperidin, naringin, and tangeretin promoted the ascorbic acid-induced lipid peroxidation, the extent of which depended upon the concentration of the flavonoid and ascorbic acid. The other flavonoids studied, viz., quercetin, quercetrin, rutin, taxifolin, myricetin, myricetrin, phloretin, phloridzin, diosmetin, diosmin, apiin, hesperetin, naringenin, (+)-catechin, morin, fisetin, chrysin, and 3-hydroxyflavone, all showed varying extents of inhibition of the nonenzymatic lipid peroxidation, induced by either ascorbic acid or ferrous sulfate. The flavonoid aglycones were more potent in their antiperoxidative action than their corresponding glycosides. Structure-activity analysis revealed that the flavonoid molecule with polyhydroxylated substitutions on rings A and B, a 2,3-double bond, a free 3-hydroxyl substitution and a 4-keto moiety, would confer upon the compound potent antiperoxidative properties.
Ratty
A K
AK
Department of Biochemistry, Faculty of Medicine, National University of Singapore.
Das
N P
NP
D000818:Animals; D001205:Ascorbic Acid / Q000494:pharmacology; D001921:Brain / Q000187:drug effects / Q000378:metabolism*; D005296:Ferrous Compounds / Q000494:pharmacology; D005419:Flavonoids / Q000494:pharmacology*; D066298:In Vitro Techniques; D008054:Lipid Peroxides / Q000096:biosynthesis*; D008297:Male; D008315:Malondialdehyde / Q000096:biosynthesis; D008928:Mitochondria / Q000187:drug effects / Q000378:metabolism; D051381:Rats; D011919:Rats, Inbred Strains; D013329:Structure-Activity Relationship
D005296:Ferrous Compounds; D005419:Flavonoids; D008054:Lipid Peroxides; C020748:ferrous sulfate; D008315:Malondialdehyde; D001205:Ascorbic Acid