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Paper | Regular issue | Vol 48, No. 4, 1998, pp.703-710
Published online, 1st January, 1970
DOI: 10.3987/COM-97-8095
Medicinal Foodstuffs. XIII. Saponin Constituents with Adjuvant Activity from Hyacinth Bean, the Seeds of Dolichos lablab L. (2): Structures of Lablabosides D, E, and F

Hajime Komatsu, Toshiyuki Murakami, Hisashi Matsuda, and Masayuki Yoshikawa*

*Kyoto Pharmaceutical University, Misasagi, Yamashina-ku, Kyoto 607-8412, Japan


Following the characterization of lablabosides A, B, and C, new oleanan-type triterpene bisdesmosides, lablabosides D, E, and F, were isolated from the glycosidic fraction with adjuvant activity obtained from the seeds of Dolichos lablab L. (Leguminosae). Their chemical structures were elucidated on the basis of chemical and physicochemical evidence as follows: 3-O-[α-L-rhamnopyranosyl (1→2)-β-D-galactopyranosyl (1→2)-β-D-glucopyranosiduronic acid]-28-O-[6-O-(3-hydroxy-3-methylglutaroyl)-β-D-glucopyranosyl] 24-epi-hederagenin(lablabside D), 3-O-[α-L-rhamnopyranosyl (1→2)-β-D-glucopyranosyl (1→2)-β-D-glucopyranosiduronic acid]-28-O-[α-L-rhamnopyranosyl (1→4)-α-L-rhamnopyranosyl (1→2)-β-D-glucopyranosyl] 24-epi-hederagenin (lablabside E), 3-O-[α-L-rhamnopyranosyl (1→2)-β-D-glucopyranosyl (1→2)-β-D-glucopyranosiduronic acid]-28-O-[α-L-rhamnopyranosyl (1→4)-α-L-rhamnopyranosyl (1→2)-β-D-glucopyranosyl] oleanolic acid (lablabside F).