Flavonol glycosides and lignans from the leaves of Opilia amentacea

Two previously undescribed flavonol tetraglycosides, isorhamnetin-3-O-a-L-rhamnopyranosyl-(1 degrees 6)-beta-D-galactopyranosyl-(1 -> 4)-alpha-L-rhamnopyranosyl-(1 -> 6)-beta-D-glucopyranoside (1) and isorhamnetin-3-O-alpha-L-rhamnopyranosyl-(1 ->)-beta-D-galactopyranosyl-(1 -> 4)-alpha-L-rhamnopyranosyl-(1 -> 6)-beta-D-galactopyranoside (2), along with nine known compounds including seven flavonoids and two lignans, were isolated from the leaves of Opilia amentacea Roxb (Opiliaceae). Their structures were established on the basis of spectroscopic analysis. The DPPH radical scavenging activity of compounds 1-11 was evaluated. In addition, all compounds were evaluated for their tyrosinase inhibitions by using in vitro mushroom tyrosinase assay. Only 5,5-dimethoxylariciresinol-4-O-beta D- glucopyranoside (10) and eleutheroside E1 (11) exhibited significant tyrosinase inhibition (IC50 42.1 and 28 mu M, respectively) and DPPH radical scavenging activity (IC50 85.1 and 42.1 mu M, respectively) compared with the positive controls.