Triterpene glycosides of Lupinus angustifolius

• Verfasst von: Woldemichael, Girma Moges [VerfasserIn]
• Verfasst von: Wink, Michael [VerfasserIn]
• Titel: Triterpene glycosides of Lupinus angustifolius
• Verf.angabe: Girma M. Woldemichael, Michael Wink
• Jahr: 2002
• Umfang: 5 S.
• Fussnoten: Gesehen am 06.10.2017
• Titel Quelle: Enthalten in: Phytochemistry reviews
• Ort Quelle: Dordrecht : Springer Science + Business Media B.V., 2002
• Jahr Quelle: 2002
• Band/Heft Quelle: 60(2002), 4, Seite 323-327
• ISSN Quelle: 1572-980X
• DOI: doi:10.1016/S0031-9422(02)00112-7
• Datenträger: Online-Ressource
• Sprache: eng
• Sach-SW: Leguminosae
• Sach-SW: Antifungal activity
• Sach-SW: Soyasapogenol glycosides
• Sach-SW: Triterpenoid saponin
• K10plus-PPN: 1564128164

Abstract

Investigation of whole seeds of Lupinus angustifolius L. (Leguminosae) yielded the two triterpenoid saponins with branched monosaccharide chain 3β,21β,22β,24-tetrahydroxyolean-12-en-3-O-α-l-rhamnopyranosyl-(1→3)-[α-l-rhamnopyranosyl-(1→2)]-β-d-galactopyranosyl-(1→2)-β-d-glucuronopyranoside (3) and 3β,21β,22β,24-tetrahydroxyolean-12-en-3-O-α-l-rhamnopyranosyl-(1→3)-[α-l-rhamnopyranosyl-(1→2)]-β-d-galactopyranosyl-(1→2)-β-d-glucuronopyranosyl-21-O-α-l-rhamnopyranoside (4) along with the known compounds soyasaponin I (1) and 3β,21β,22β,24-tetrahydroxyolean-12-en-3-O-α-l-rhamnopyranosyl-(1→2)-β-d-galactopyranosyl-(1→2)-β-d-glucuronopyranosyl-21-O-α-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 μg/ml, respectively. Only soyasaponin I was found weakly hemolytic (HC50 >500 μg/ml).