Triterpene glycosides of Lupinus angustifolius.
Investigation of whole seeds of Lupinus angustifolius L. (Leguminosae) yielded the two triterpenoid saponins with branched monosaccharide chain 3 beta,21 beta,22 beta,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 3 beta,21 beta,22 beta,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 I (1) and 3 beta,21 beta,22 beta,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 microg/ml, respectively. Only soyasaponin I was found weakly hemolytic (HC(50) >500 microg/ml).
Woldemichael
Girma M
GM
Institut für Pharmazeutische Biologie, Universität Heidelberg, Im Neuenheimer Feld 364, 69120 Heidelberg, Germany.
Wink
Michael
M
D000818:Animals; D000935:Antifungal Agents / Q000737:chemistry / Q000494:pharmacology; D002176:Candida albicans / Q000187:drug effects; D004912:Erythrocytes / Q000187:drug effects; D005858:Germany; D006027:Glycosides / Q000737:chemistry* / Q000494:pharmacology; D006461:Hemolysis / Q000187:drug effects; D031297:Lupinus / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy / Q000379:methods; D008826:Microbial Sensitivity Tests / Q000379:methods; D010936:Plant Extracts; D010946:Plants, Medicinal / Q000737:chemistry; D012503:Saponins / Q000737:chemistry* / Q000494:pharmacology; D012639:Seeds / Q000737:chemistry; D012756:Sheep; D016339:Spectrometry, Mass, Fast Atom Bombardment; D014315:Triterpenes / Q000737:chemistry* / Q000494:pharmacology
D000935:Antifungal Agents; D006027:Glycosides; D010936:Plant Extracts; D012503:Saponins; D014315:Triterpenes