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Functional New Acylated Sophoroses and Deglucosylated Anthocyanins in a Fermented Red Vinegar
- Terahara, Norihiko, Matsui, Toshiro, Minoda, Kanako, Nasu, Kanae, Kikuchi, Risa, Fukui, Keiichi, Ono, Hiroshi, Matsumoto, Kiyoshi
- Journal of agricultural and food chemistry 2009 v.57 no.18 pp. 8331–8338
- functional properties, acylation, polyphenols, fermented foods, vinegars, food analysis, food composition
- The new acylated polyphenols were isolated from a red-colored vinegar produced via fermentation with purple-fleshed sweet potato storage roots, and identified mainly by MS and NMR. The three acylated sophoroses were determined as 6-O-(E)-caffeoyl-(2-O-(6-O-acyl)-β-d-glucopyranosyl)-d-glucopyranoses, where acyl was (E)-caffeoyl, p-hydroxybenzoyl, and (E)-feruloyl, respectively. The four acylated anthocyanins were also determined as cyanidin 3-O-(6-O-(E)-caffeoyl-(2-O-(6-O-(E)-feruloyl)-β-d-glucopyranosyl)-β-d-glucopyranoside), in addition to peonidin 3-O-(6-O-(E)-caffeoyl-(2-O-(6-O-acyl)-β-d-glucopyranosyl)-β-d-glucopyranosides), where acyl was (E)-caffeoyl, p-hydroxybenzoyl, and (E)-feruloyl, respectively. The diacylated sophoroses showed higher antioxidant capacity than that of monoacylated analogue 6-caffeoylsophorose, so the multiacylation established to enhance their antioxidant capacity. Similarly, 5-deglucosylated anthocyanins also gave somewhat stronger antioxidation than corresponding sweet potato anthocyanins. In rat intestinal α-glucosidase inhibition study, the diacylated sophoroses preferably inhibited maltase rather than sucrase with an IC50 value of <300 μM, indicating a potential role as antidiabetic phytochemicals. These acylated polyphenols in a red vinegar were expected to play important functional roles for health.