Flavan and procyanidin glycosides from the bark of blackjack oak.

The bark of blackjack oak contains (+)-catechin, (-)-epicatechin, (+)-3-O-[beta-D-glucopyranosyl]-catechin, catechin-(4 alpha-->8)-catechin, epicatechin-(4 beta-->8)-catechin as well as the novel 3-O-[beta-D-glucopyranosyl]-catechin-(4 alpha-->8)-catechin and 3-O-[alpha-L-rhamnopyranosyl-(1-->6)-beta-D-glucopyranosyl]-catechin, as major components. The latter rutinoside of catechin is especially interesting because of the exceptionally small J2,3 C-ring coupling. The glucoside of catechin-(4 alpha-->8)-catechin is only the second proanthocyanidin found in nature in which a 3-O-glycoside is present in the upper 'extender unit' of a dimer.