New dammarane-type saponins from the galls of Sapindus mukorossi

Five new dammarane-type saponins, 3 beta,7 beta,20(S),22-tetrahydroxydammar-24-ene-3-O-alpha-L-rhamnopyranosyl-(1 -> 2)-beta-D-glucopyranoside, 3 beta,7 beta,20(S),22,23-pentahydroxydammar-24-ene-3-O-alpha-L-rhamnopyranosyl-(1 -> 2)-beta-D-glucopyranoside, 3 beta,7 beta,20(S),22,25-pentahydroxydammar-23-ene-3-O-alpha-L-rhamnopyranosyl-(1 -> 2)-beta-D-glucopyranoside, 25-methoxy-3 beta,7 beta,20(S),22-tetrahydroxydam mar23-ene-3-O-alpha-L-rhamnopyranosyl-(1 -> 2)-beta-D-glucopyranoside, and 25-methoxy-3 beta,7 beta,20(R)-trihydroxydam mar-23-ene-3-O-alpha-L- rhamnopyranosyl-(l -2) -beta-D-gl ucopyranoside, named sapinmusaponins A (1), B (2), C (3), D (4), and E (5), respectively, together with three known phenylpropanoid glycosides (6-8), were isolated from the galls of Sapindus mukorossi. The structures of these saponins were elucidated on the basis of spectroscopic analyses and chemical methods. Preliminary bioassay data revealed that saponins 1 and 3-5 showed moderate cytotoxic activity (ED50 - 9-18,mu g/mL) against human tumor cell lines (Hepa59TNGH, NCl, HeLa, and Med) and that 1-5 were inactive in vitro against HIV replication in H9 lymphocytes.