title: Oxidation products of cyanidin 3-O-beta-D-glucoside with a free radical initiator.
abstract: Recently, we have reported that anthocyanins show strong antioxidative activity, but no attention has been paid to anthocyanins from the viewpoint of the reaction mechanism of alkylperoxyl radicals; therefore, we investigated the reaction products of antioxidative anthocyanins (cyanidin 3-O-beta-D-glucoside). Cyanidin 3-O-beta-D-glucoside was reacted with 2,2'-azobis(2,4-dimet hylvaleronitrile) to generate the alkylperoxyl radicals, and the reaction products were isolated by high-performance liquid chromatography. The products were identified as 4,6-dihydroxy-2-O-beta-D-glucosyl-3-oxo-2,3-dihydroben-zofuran+ ++ and protocatechuic acid. Based on reaction products, the antioxidative mechanism of cyanidin 3-O-beta-D-glucoside may be different from that of alpha-tocopherol; cyanidin 3-O-beta-D-glucoside would produce another radical scavenger, as it would break down the structure and scavenge the radicals.
authors.affiliation: Tokaigakuen Women's College, Nagoya, Japan.
authors.forename: T
authors.initials: T
authors.lastname: Tsuda
authors.forename: K
authors.initials: K
authors.lastname: Ohshima
authors.forename: S
authors.initials: S
authors.lastname: Kawakishi
authors.forename: T
authors.initials: T
authors.lastname: Osawa
mesh_terms: D000872:Anthocyanins / Q000737:chemistry / Q000378:metabolism; D001391:Azo Compounds / Q000737:chemistry / Q000378:metabolism; D001578:Benzopyrans / Q000737:chemistry* / Q000378:metabolism*; D016166:Free Radical Scavengers / Q000737:chemistry / Q000378:metabolism; D005609:Free Radicals / Q000737:chemistry / Q000378:metabolism; D006031:Glycosylation; D066298:In Vitro Techniques; D007700:Kinetics; D008956:Models, Chemical; D015394:Molecular Structure; D009570:Nitriles / Q000737:chemistry / Q000378:metabolism; D010084:Oxidation-Reduction
chemical_list: D000872:Anthocyanins; D001391:Azo Compounds; D001578:Benzopyrans; D016166:Free Radical Scavengers; D005609:Free Radicals; D009570:Nitriles; C055792:2,2'-azobis(2,4-dimethylvaleronitrile); C017154:cyanidin