Superoxide radical- and peroxynitrite-scavenging activity of anthocyanins; structure-activity relationship and their synergism.
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.
Rahman
M Mamunur
MM
Niigata University of Pharmacy and Applied Life Sciences, Faculty of Applied Life Sciences, 265-1 Higashijima, Niigata, Japan.
Ichiyanagi
Takashi
T
Komiyama
Tadazumi
T
Hatano
Yoshihiko
Y
Konishi
Tetsuya
T
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
D000872:Anthocyanins; D016166:Free Radical Scavengers; D013481:Superoxides; D030421:Peroxynitrous Acid; D014443:Tyrosine