Studies on the constituents of Clematis species. VI. The constituents of Clematis stans SIEB et ZUCC

Article abstract of DOI:10.1248/cpb.43.2187

From the roots of Clematis stans three new oleanane-type triterpenoid saponins named clemastanoside A, B and C, and two new lignan glycosides named clemastanin A and B, have been isolated together with three known triterpenoid saponins, huzhangoside B, C and D, and three known lignan glycosides, (+)-lariciresinol 4-O-β-D-glucopyranoside, (+)-lariciresinol 4'- O-β-D-glucopyranoside and (+)-pinoresinol 4,4'-O-bis-β-D-glucopyranoside. In addition, from the leaves, four new oleanane-type triterpenoid saponins, named clemastanoside D, E, F and G, have been isolated together with five known triterpenoid saponins, hederasaponin B, kizutasaponin K₁₂, huzhangoside B, sieboldianoside B and huzhangoside D, and three known flavonoids, isoquercitrin, ratin and quercetin 3-O-β-D-glucuronopyranoside. The structures of the new compounds were elucidated based on chemical and physicochemical evidence as follows: clemastanoside A, 3-O-β-D- ribopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→2)-α-L-arabinopyranosyl oleanolic acid 28-O-(4-O-acetyl)-α-L-rhamnopyranosyl-(1→4)-β-D- glucopyranosyl-(1→6)-β-D-glucopyranosyl ester (terminal rhamnosyl 4-O- acetate of huzhangoside B); clemastanoside B and C, 3-O-β-D-xylopyranosyl- and 3-O-β-D-ribopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→2)-β-D- galactopyranosyl oleanolic acid 28-O-α-L-rhamnopyranosyl-(1→4)-β-D- glucopyranosyl-(1→6)-β-D-glucopyranosyl ester, respectively; clemastanoside D, 3-O-β-D-ribopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→2)-α-L- arabinopyranosyl hederagenin 28-O-β-D-glucopyranosyl ester; clemastanoside E, F and G, terminal rhamnosyl 4-O-, 3-O- and 2-O-acetate of 3-O-β-D- ribopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→2)-α-L-arabinopyranosyl hederagenin 28-O-α-L-rhamno-pyranosyl-(1→4)-β-D-glucopyranosyl-(1→6]-β- D-glucopyranosyl ester, respectively; clemastanin A, (7S,8R)-3-methoxy- 3',4,9,9'-tetrahydroxy-4',7-epoxy-5',8-lignan 3'-O-β-D-glucopyranoside; clemastanin B, (+)-lariciresinol 4,4'-O-bis-β-D-glucopyranoside.

Full text of DOI:10.1248/cpb.43.2187

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