Saikosaponin homologues from Clinopodium spp. The structures of clinoposaponins XII-XX.
Nine new saikosaponin homologues, called clinoposaponins XII-XX, were isolated from the aerial parts of Clinopodium vulgare, C. chinense and C. chinense var. parviflorum together with nine known saikosaponin homologues. On the basis of spectral and chemical evidence, the structures of clinoposaponins XII-XX were determined to be 3-O-[beta-D-glucopyranosyl-(1-->2)-beta-D-glucopyranosyl] saikogenin F, 3-O-beta-D-fucopyranosyl-21 beta- hydroxysaikogenin F, 3-O-[beta-D-glucopyranosyl-(1--> 3)-beta-D-fucopyranosyl]-21 beta-hydroxysaikogenin F, 3-O-[beta-D- glucopyranosyl-(1-->2)-beta-D-glucopyranosyl]saikogenin F, 3-O-[beta-D-glucopyranosyl-(1-->2)-[beta-D-glucopyranosyl- (1-->3)]-beta-D-fucopyranosyl]-21 beta-hydroxysaikogenin F, 3-O-[beta-D-glucopyranosyl-(1-->2)-[beta-D-glucopyranosyl- (1-->3)]-beta-D-fucopyranosyl]-23-oxosaikogenin E, 3-O- [beta-D-glucopyranosyl-(1-->2)-[beta-D-glucopyranosyl-(1-->3)]-beta- D-fucopyranosyl]-16-ketosaikogenin F, 3-O-[beta-D-glucopyranosyl-(1--> 2)-[beta-D-glucopyranosyl-(1-->3)]-beta-D-fucopyranosyl]-30-hydroxysa ikogenin F, 3-O-[beta-D-glucopyranosyl-(1-->2)-[beta-D-glucopyranosyl-(1-->3)] -beta-D-fucopyranosyl]-30-oxo-saikogenin F, respectively. The known saponins were assigned to be clinoposaponins III, V, IX, X, XI, buddlejasaponins I, IV, 3-O-beta-D-fucopyranosylsaikogenin F and saikosaponin a.
Miyase
T
T
School of Pharmaceutical Sciences, University of Shizuoka, Japan.
Matsushima
Y
Y
D002236:Carbohydrate Conformation; D009682:Magnetic Resonance Spectroscopy; D009828:Oleanolic Acid / Q000031:analogs & derivatives*; D012502:Sapogenins / Q000737:chemistry*; D012503:Saponins; D016339:Spectrometry, Mass, Fast Atom Bombardment
D012502:Sapogenins; D012503:Saponins; D009828:Oleanolic Acid; C025759:saikosaponin D