Journal
PHYTOCHEMISTRY
Volume 60, Issue 4, Pages 323-327Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/S0031-9422(02)00112-7
Keywords
Lupinus angustifolius; Leguminosae; triterpenoid saponin; antifungal activity; soyasapogenol glycosides; Candida albicans
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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-->3)-[alpha-L-rhamnopyranosyl-(1-->2)]-beta-D-galactopyranosyl-(1-->2)-beta-D-glucuronopyranoside (3) and 3beta,21beta,22beta,24-tetrahydroxyolean-12-en-3-O-alpha-L-rhamnopyranosyl-(1-->3)-[alpha-L-rhamnopyranosyl-(1-->2)]-beta-D-galactopyranosyl-(1-->2)-beta-D-glucuronopyranosyl-21-O-alpha-L-rhamnopyranoside (4) along with the known compounds soyasaponin 1 (1) and 3beta,21beta,22beta,24-tetrahydroxyolean-12-en-3-O-alpha-L-rhamnopyranosyl-(1-->2)-beta-D-galactopyranosyl-(1-->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 mug/ml, respectively. Only soyasaponin I was found weakly hemolytic (HC50 > 500 mug/ml). (C) 2002 Elsevier Science Ltd. All rights reserved.
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