Triterpene glycosides of Lupinus angustifolius
2002
Woldemichael, G.M. | Wink, M.
Investigation of whole seeds of Lupinus angustifolius L. (Leguminosae) yielded the two triterpenoid saponins with branched monosaccharide chain 3beta,21beta,22beta, 24-tetrahydroxyolean-12-en-3-O-alpha-L-rhamnopyranosyl- (1 leads to 3)-[alpha-L-rhamnopyranosyl-(1 leads to 2)]-beta-D-galactopyranosyl-(1 leads to 2)-beta-D-glucuronopyranoside (3) and 3beta,21beta,22beta, 24-tetrahydroxyolean-12-en-3-O-alpha-L-rhamnopyranosyl- (1 leads to 3)-[alpha-L-rhamnopyranosyl-(1 leads to 2)]-beta-D-galactopyranosyl-(1 leads to 2)-beta-D-glucuronopyranosyl-21-O-alpha-L- rhamnopyranoside (4) along with the known compounds soyasaponin I (1) and 3beta,21beta,22beta, 24-tetrahydroxyolean-12-en-3-O-alpha-L-rhamnopyranosyl- (1 leads to 2)-beta-D-galactopyranosyl-(1 leads to 2)-beta-D-glucuronopyranosyl-21-O-alpha-L- rhamnopyranoside (2). The structures of the compounds were elucidated using hydrolysis, FAB-MS and extensive NMR experiments. Compounds 2-4 showed moderate antifungal activity against Candida albicans with MIC values of 25, 25 and 30 microgram/ml, respectively. Only soyasaponin I was found weakly hemolytic (HC50 > 500 microgram/ml).
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