title: Superoxide radical- and peroxynitrite-scavenging activity of anthocyanins; structure-activity relationship and their synergism.
abstract: Antioxidant activities of 15 purified bilberry anthocyanins together with pelargonidin 3-O-beta-D-glucopyranoside and 4'-O-methyl delphinidin 3-O-beta-D-glucopyranoside (MDp 3-glc), the major metabolite of delphinidin 3-O-beta-D-glucopyranoside (Dp 3-glc), were evaluated in order to study the structure-antioxidant activity relationship and any synergism among them in the mixture. Both aglycone structure and the attached sugar moiety affected the O*2- and ONOO- -scavenging activities, although the effect of the attached sugar moiety was smaller than that of the aglycone structure. The potency of activity toward the superoxide radical was in the following order: delphinidin > petunidin > malvidin =approximately cyanidin>(+)-catechin > peonidin > pelargonidin. The activity toward ONOO- was: delphinidin > cyanidin =approximately petunidin > malvidin =approximately (+)-catechin > peonidin > pelargonidin. It was confirmed that methylation of 4'-OH markedly reduced the antioxidant activity of anthocyanin. Further, it was revealed that synergism occurred in both - and ONOO- -scavenging activities among the anthocyanins in the mixture.
authors.affiliation: Niigata University of Pharmacy and Applied Life Sciences, Faculty of Applied Life Sciences, 265-1 Higashijima, Niigata, Japan.
authors.forename: M Mamunur
authors.initials: MM
authors.lastname: Rahman
authors.forename: Takashi
authors.initials: T
authors.lastname: Ichiyanagi
authors.forename: Tadazumi
authors.initials: T
authors.lastname: Komiyama
authors.forename: Yoshihiko
authors.initials: Y
authors.lastname: Hatano
authors.forename: Tetsuya
authors.initials: T
authors.lastname: Konishi
mesh_terms: D000818:Animals; D000872:Anthocyanins / Q000737:chemistry* / Q000302:isolation & purification / Q000493:pharmacokinetics; D004357:Drug Synergism; D016166:Free Radical Scavengers / Q000737:chemistry* / Q000302:isolation & purification / Q000493:pharmacokinetics; D008297:Male; D015394:Molecular Structure; D030421:Peroxynitrous Acid / Q000138:chemical synthesis / Q000737:chemistry* / Q000378:metabolism; D051381:Rats; D017208:Rats, Wistar; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D013481:Superoxides / Q000037:antagonists & inhibitors / Q000737:chemistry*; D014443:Tyrosine / Q000031:analogs & derivatives / Q000737:chemistry / Q000187:drug effects; D029800:Vaccinium myrtillus / Q000737:chemistry
chemical_list: D000872:Anthocyanins; D016166:Free Radical Scavengers; D013481:Superoxides; D030421:Peroxynitrous Acid; D014443:Tyrosine