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)-beta-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)-beta-d-glucopyranosyl)-beta-d-glucopyranoside), in addition to peonidin 3-O-(6-O-(E)-caffeoyl-(2-O-(6-O-acyl)-beta-d-glucopyranosyl)-beta-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 alpha-glucosidase inhibition study, the diacylated sophoroses preferably inhibited maltase rather than sucrase with an IC(50) value of <300 microM, indicating a potential role as antidiabetic phytochemicals. These acylated polyphenols in a red vinegar were expected to play important functional roles for health.