Anticomplement activities of oleanolic acid monodesmosides and bisdesmosides isolated from tiarella polyphylla

Abstract

Seven known oleanolic acid glycosides (1-7) were isolated from the MeOH extract of Tiarella polyphylla. The structures were identified to be 3-O-(β-D-glucopyranosyl) oleanolic acid (1), 3-O-[β-D-glucopyranosyl-(1→3)-β-D-glucopyranosyl] oleanolic acid (2), 3-O-[β-D-glucopyranosyl-(1→2)-β-D-glucopyranosyl] oleanolic acid (3), 3-O-[β-D-glucopyranosyl-(1→3)-β-D-glucopyranosyl] oleanolic acid 28-O-β-D-glucopyranosyl ester (4), 3-O-[β-D-glucopyranosyl-(1→2)-β-D-glucopyranosyl] oleanolic acid 28-O-β-D-glucopyranosyl ester (5), 3-O-[a-L-rhamnopyranosyl-(1→3)-β-D-glucuronopyranosyl] oleanolic acid (6), and 3-O-[α-L-rhamnopyranosyl-(1→3)-β-D-glucuronopyranosyl] oleanolic acid 28-O-β-D-glucopyranosyl ester (7) on the basis of physicochemical and spectral data. These triterpene glycosides were tested for the anticomplement activity and hemolytic activity. Bisdesmosidic saponins, 4, 5, and 7, showed anticomplement activity; in contrast, monodesmosidic saponins, 1-3, and 6, showed direct hemolytic activity. Methyl esterified monodesmosidic saponins showed anticomplement activity at a low concentration and hemolytic activity at a high concentration.