Medicinal foodstuffs. XII. Saponin constituents with adjuvant activity from hyacinth bean, the seeds of Dolichos lablab L. (1): Structures of lablabosides A, B, and C.
From the glycoside mixture with adjuvant activity obtained from the hyacinth bean, the seeds of Dolichos lablab L., six new oleanane-type triterpene bisdesmosides, lablabosides A, B, C, D, E, and F, were isolated together with chikusetsusaponin IVa. The structures of lablabosides A, B, and C were determined on the basis of chemical and physicochemical evidence as follows: 3-O-[alpha-L-rhamnopyranosyl (1-->2)-beta-D-galactopyranosyl (1-->2)-beta-D-glucopyranosiduronic acid]-28-O-(beta-D-glucopyranosyl) oleanolic acid (lablaboside A), 3-O-[alpha-L-rhamnopyranosyl (1-->2)-beta-D-galactopyranosyl (1-->2)-beta-D-glucopyranosiduronic acid]-28-O-(beta-D-glucopyranosyl) 24-epi-hederagenin (lablaboside B), 3-O-[alpha-L-rhamnopyranosyl (1-->2)-beta-D- galactopyranosyl (1-->2)-beta-D-glucopyranosiduronic acid]-28-O-[alpha-L-rhamnopyranosyl (1-->2)-beta-D-glucopyranosyl] 24-epi-hederagenin (lablaboside C).
Yoshikawa
M
M
Kyoto Pharmaceutical University, Japan.
Murakami
T
T
Komatsu
H
H
Matsuda
H
H
D000276:Adjuvants, Immunologic / Q000737:chemistry / Q000302:isolation & purification*; D002240:Carbohydrate Sequence; D006868:Hydrolysis; D009682:Magnetic Resonance Spectroscopy; D008969:Molecular Sequence Data; D009828:Oleanolic Acid / Q000031:analogs & derivatives*; D010946:Plants, Medicinal / Q000737:chemistry*; D012503:Saponins / Q000737:chemistry / Q000302:isolation & purification*; D012639:Seeds / Q000737:chemistry; D016339:Spectrometry, Mass, Fast Atom Bombardment; D013055:Spectrophotometry, Infrared; D013056:Spectrophotometry, Ultraviolet
D000276:Adjuvants, Immunologic; D012503:Saponins; C112902:lablaboside A; C112903:lablaboside B; C112905:lablaboside C; D009828:Oleanolic Acid