Identification of reaction products of acylated anthocyanins from red radish with peroxyl radicals.
Red radish anthocyanin extract, which consists of 12 known acylated anthocyanins, was reacted with 2,2'-azobis(2-amidinopropane) dihydrochloride (AAPH) to generate peroxyl radicals under acidic pH conditions at 37 degrees C. The reaction products were isolated using preparative HPLC, and their chemical structures were determined to be p-hydroxybenzoic acid (1), 6-O-(E)-p-coumaroyl-2-O-beta-d- glucopyranosyl-alpha-d-glucopyranoside (3), p-coumaric acid (4), 6-O-(E)-feruloyl-2-O-beta-d-glucopyranosyl-alpha-d-glucopyranoside (5), and ferulic acid (6). Some products were not identified. HPLC analyses of the mixture of acylated pelargonidin isolated from red radish and AAPH revealed that the acylated pelargonidins possess the radical scavenging ability on some common sites even if the characteristics of the intramolecular acyl units are different. Degradation rates of acylated pelargonidins and the formation rates of the resulting reaction products were found to be quite different.
Matsufuji
Hiroshi
H
Department of Food Science and Technology, College of Bioresource Sciences, Nihon University, 1866 Kameino, Fujisawa, Kanagawa 252-8510, Japan. hmatsufu@brs.nihon-u.ac.jp
Otsuki
Takashi
T
Takeda
Toshiyuki
T
Chino
Makoto
M
Takeda
Mitsuharu
M
D000215:Acylation; D000872:Anthocyanins / Q000032:analysis* / Q000737:chemistry*; D002851:Chromatography, High Pressure Liquid; D003373:Coumaric Acids / Q000737:chemistry / Q000302:isolation & purification; D062385:Hydroxybenzoates / Q000737:chemistry / Q000302:isolation & purification; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D010545:Peroxides / Q000737:chemistry*; D011422:Propionates; D031224:Raphanus / Q000737:chemistry*; D014675:Vegetables / Q000737:chemistry
D000872:Anthocyanins; D003373:Coumaric Acids; D062385:Hydroxybenzoates; D010545:Peroxides; D011422:Propionates; C049375:perhydroxyl radical; C004999:ferulic acid; C495469:p-coumaric acid