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Abstract
Four saponins were isolated from the methanol extract of the pericarps of Guaiacum officinale using a bioassay with the snail Biomphalaria glabrata. Their structures were established as 3-O-(ß-D-glucopyranosyluronic acid)-oleanolic acid (1), 3-O-{[a-L-rhamnopyranosyl(1?3)-a-L-rhamnopyranosyl(1?2)]-a-L-arabinopyranosyl (3?1) [-ß-D-glucopyranosyl]}-30-norolean-12,20(29)dien-28-oic acid (2, guaianin D), a-D-glucopyranosyl 3-O-[a-L-rhamnopyranosyl (1?3)-ß-D-glucopyranosyl(1?3)-a-L-arabinopyranosyl]-30-norolean-12,20-(29) dienoate (3, guaianin B) and ß-D-glucopyranosyl 3-O-[a-L-rhamnopyranosyl (1?3)-ß-D-glucopyranosyl(1?3)-a-L-arabinopyranosyl]-oleanolate (4, guaianin C). The LC 100 /24h of monodesmosidic saponins 1 and 2 were 2.5 and 10 ppm, respectively, while the bidesmosidic saponins 3 and 4 were inactive at 10 ppm. Basic hydrolysis of 3 and 4 produced the corresponding monodesmosidic saponins 5 (guaianin) and 6 (guaianin H). These saponins were active at 2.5 and 5 ppm, respectively.