Functional new acylated sophoroses and deglucosylated anthocyanins in a fermented red vinegar.
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.
Terahara
Norihiko
N
Department of Food Science for Health, Faculty of Health and Nutrition, Minami-Kyushu University, 5-1-2 Kirishima, Miyazaki 880-0032, Japan. terahara@nankyudai.ac.jp
Matsui
Toshiro
T
Minoda
Kanako
K
Nasu
Kanae
K
Kikuchi
Risa
R
Fukui
Keiichi
K
Ono
Hiroshi
H
Matsumoto
Kiyoshi
K
D019342:Acetic Acid / Q000737:chemistry*; D000215:Acylation; D000872:Anthocyanins / Q000032:analysis* / Q000737:chemistry; D000975:Antioxidants / Q000737:chemistry / Q000494:pharmacology; D004791:Enzyme Inhibitors / Q000494:pharmacology; D005285:Fermentation; D005419:Flavonoids / Q000032:analysis / Q000737:chemistry / Q000494:pharmacology; D005936:Glucans / Q000032:analysis* / Q000737:chemistry; D065089:Glycoside Hydrolase Inhibitors; D006031:Glycosylation; D027723:Ipomoea batatas / Q000737:chemistry; D010636:Phenols / Q000032:analysis / Q000737:chemistry / Q000494:pharmacology; D018517:Plant Roots / Q000737:chemistry; D059808:Polyphenols; D013329:Structure-Activity Relationship
D000872:Anthocyanins; D000975:Antioxidants; D004791:Enzyme Inhibitors; D005419:Flavonoids; D005936:Glucans; D065089:Glycoside Hydrolase Inhibitors; D010636:Phenols; D059808:Polyphenols; D019342:Acetic Acid; C003328:sophorose