Twelve different seed coat color genotypes of Phaseolus vulgaris L. were extracted and pure flavonoids isolated from 10 of these. The seed coat methanol extracts, tannin fractions, and pure flavonoids all displayed antioxidant activity in a fluorescence-based liposome assay. The relatively high activity of the condensed tannin (proanthocyanidin) fractions indicates that these may play an important role in the overall activity of the extracts. This activity also indicates that although these polyphenols cause problems in digestibility, they may be important dietary supplements with beneficial health effects. The pure anthocyanins delphinidin 3-O-glucoside (1), petunidin 3-O-glucoside (2), and malvidin 3-O-glucoside (3) and the flavonol quercetin 3-O-glucoside (4) isolated from seed coats also had significantly higher antioxidant activity than the Fe(2+) control. The activity of kaempferol 3-O-glucoside (5) was not different from that of the Fe(2+) control. These findings suggest that variously colored dry beans may be an important source of dietary antioxidants.
Proanthocyanidins and flavonoids were isolated and identified from seed coats of two aged and nonaged pinto bean lines: 1533-15 and CDC Pintium. The seed coat of 1533-15 darkens slowly and never darkens to the same extent as CDC Pintium. Analysis of the overall level of proanthocyanidins using a vanillin assay demonstrated that aged and nonaged seed coats of CDC Pintium had significantly higher levels of proanthocyanidins than aged and nonaged 1533-15 seed coats. Aged and nonaged seed coats of both lines were found to contain one main flavonol monomer, kaempferol, and three minor flavonols, kaempferol 3-O-glucoside, kaempferol 3-O-glucosylxylose, and kaempferol 3-O-acetylglucoside. These compounds were identified by NMR and ESI-MS analysis (except for kaempferol 3-O-acetylglucoside, which was tentatively identified only by ESI-MS analysis) and quantified using HPLC-DAD. The combined concentrations of all the kaempferol compounds in seed coats of CDC Pintium were significantly higher than in seed coats of 1533-15, and the combined contents did not change after aging. The content of kaempferol decreased nearly by half in the seed coats of CDC Pintium after aging, whereas no significant change was observed in the seed coats of 1533-15. Proanthocyanidin fractions from both lines, aged and nonaged, were subjected to LC-MS/MS analysis and found to be composed primarily of procyanidins. Procyanidins in the seed coats were predominantly polymers with the degree of polymers higher than 10. The proportion of these polymers decreased after aging, while that of the low-molecular-weight procyanidins increased. A catechin-kaempferol adduct was tentatively identified in both lines by LC-MS/MS, and the concentration increased in the seed coats after aging.
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