Comparative Studies on the Constituents of Ophiopogonis Tuber and Its Congeners. III. Studies on the Constituents of the Subterranean Part of Ophiopogon ohwii OKUYAMA and O. jaburan (KUNTH) LODD.

抄録

Six steroidal glycosides, tentatively named glycosides O-1, O-2 (1), O-3 (2), O-4 (3), O-5 (4) and O-6 (5), were isolated from the subterranean part of Ophiopogon ohwii OKUYAMA (Liliaceae) and another six steroidal glycosides, tentatively named glycosides J-1, J-2 (6), J-3 (7), J-4 (8), J-5 (9) and J-6 (10), were isolated from the subterranean part of O. jaburan (KUNTH) LODD. Glycosides O-1 and J-1 were identified as so-called β-sitosterol β-D-glucopyranoside. The structures of 1-10 were established as ophiopogonin B (1), ophiopogonin D (2), ruscogenin 1-O-α-L-rhamnopyranosyl(1→2)-4-O-sulfo-β-D-fucopyranoside (3), ruscogenin 1-O-α-L-rhamnopyranosyl(1→2)-4-O-sulfo-α-L-arabinopyranoside (=glycoside E of O. planiscapus NAKAI) (4), 26-O-β-D-glucopyranosyl 22-hydroxy-25(R)-furost-5-en-1β, 3β, 26-triol 1-O-α-L-rhamnopyranosyl(1→2)-4-O-sulfo-β-D-fucopyranoside (5), ophiopogonin D (=glycoside O-3 (2)) (6), a mixture of 1-O-α-L-rhamnopyranosyl(1→2)-4-O-sulfo-β-D-fucopyranosido-3-O-β-D-glucopyranosides of ruscogenin and neoruscogenin (7), neoruscogenin 1-O-α-L-rhamnopyranosyl(1→2)-4-O-sulfo-α-L-arabinopyranosido-3-O-β-D-glucopyranoside (8), a mixture of 26-O-β-D-glucopyranosyl 22-hydroxy-25(R)-furost-5-en-1β, 3β, 26-triol 1-O-α-L-rhamnopyranosyl(1→2)-4-O-sulfo-β-D-fucopyranosido-3-O-β-D-glucopyranoside and 26-O-β-D-glucopyranosyl 22-hydroxyfurost-5, 25(27)-dien-1β, 3β, 26-triol 1-O-α-L-rhamnopyranosyl(1→2)-4-O-sulfo-β-D-fucopyranosido-3-O-β-D-glucopyranoside (9), and 26-O-β-D-glucopyranosyl 22-hydroxyfurost-5, 25(27)-dien-1β, 3β, 26-triol 1-O-α-L-rhamnopyranosyl(1→2)-4-O-sulfo-α-L-arabinopyranosido-3-O-β-D-glucopyranoside (10). It is interesting that the main saponins, ophiopogonins B and D, found in Ophiopogonis Tuber (obtained from O. japonicus KER-GAWLER) were also found in O. ohwii OKUYAMA and the latter saponin was also found in O. jaburan (KUNTH) LODD. Further, several steroidal glycosides carrying sulfate on the sugar moiety were found in Liliaceous plants belonging to the genus Ophiopogon.