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.

Characterization of Antioxidant Capacity from Fruits with Distinct Anthocyanin Biosynthetic Pathways

“…The standard AACI was consistently lower than the range of ORAC values obtained for the anthocyanin extracts from each blackcurrant and grape cultivar. Others have reported a similar result with a standardized extract resembling bilberry which was 5-times weaker than the actual bilberry extract [35]. Thus, a potential synergy between anthocyanin components in a complex mixture along with the total anthocyanin content together contribute to the total antioxidant capacity of the fruit.…”

“…Our results showed delphinidin, a trihydroxy anthocyanin at positions 3',4',5'-B ring had relatively lower ORAC activity than cyanidin which has two hydroxyl groups at positions 3' and 4' on the B ring. Our finding agrees with other studies that have used the ORAC assay [5] and the in vitro Cu 2 + -mediated LDL oxidation assay [14], but is in contrast to studies that have shown delphinidin to possess greater activity at scavenging both superoxide and peroxynitrite radicals than cyanidin [35]. Malvidin, which contains O-methyl group on 4' position on the B-ring, was also lower in activity than cyanidin, which has two hydroxyl groups attached.…”

“…The apparent importance of extra hydroxyl groups associated with the B-ring for eliciting high antioxidant activity does not hold true for delphinidin 3-glucoside, which possesses an extra hydroxyl group in C-5' position, but had a relatively lower ORAC value compared to cyanidin 3-glucoside. Methoxylation of cyanidin and delphinidin did not have a significant effect on ORAC antioxidant capacity, but does adversely affect the scavenging activity of superoxide radicals [35]. It was also of particular interest that the attached sugar moiety did not affect the ORAC antioxidant capacity of same aglycon, as 3-glucoside and 3-rutionoside were similar for both cyanidin and delphinidin anthocyanins.…”

Antioxidant Small Phenolic Ingredients in Inonotus obliquus (persoon) Pilat (Chaga)

“…17) Hypoxanthin/xanthine oxdase system was used as O 2 Ϫ generator. To pH 7.4 PBS buffer (170 ml), 2 mM hypoxanthine (160 ml), 10 mM DTPA (60 ml), 9.2 M DMPO (20 ml) and various concentration of the sample solution was added under stirring condition and then followed by the addition of 0.4 U/ml xanthine oxidase (160 ml).…”

Differential Effects of Cyanidin and Cyanidin-3-glucoside on Human Cell Lines

“…Anthocyanins and their aglycons, anthocyanidins, have various biological effects, such as antioxidative activity (Cao et al, 1997;Kahkonen and Heinonen, 2003;Rahman et al, 2006;Tsuda et al, 1999a), anti-hyperglycemic activity (Matsui et al, 2002), anti-inflammatory activity (Karlsen et al, 2007;Wang et al, 2008b), cell protective activity (Elisia and Kitts, 2008;Tarozzi et al, 2007) and antitumor activity (Hou, 2003;Lala et al, 2006;Kang et al, 2003). One major anthocyanidin is cyanidin, and the effects of cyanidin and cyanin, its glycoside, have been investigated, but the biological effects of these compounds are not fully understood.…”