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Studies on the constituents of Clematis species. VI. The constituents of Clematis stans Sieb. et Zucc.
Chem Pharm Bull (Tokyo). 1995 Dec; 43(12):2187-94.CP

Abstract

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-beta-D-glucopyranoside, (+)-lariciresinol 4'-O-beta-D-glucopyranoside and (+)-pinoresinol 4,4'-O-bis-beta-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, rutin and quercetin 3-O-beta-D-glucuronopyranoside. The structures of the new compounds were elucidated based on chemical and physicochemical evidence as follows: clemastanoside A, 3-O-beta-D-ribopyranosyl-(1-->3)-alpha-L-rhamnopyranosyl-(1-->2)-a lpha-L- arabinopyranosyl oleanolic acid 28-O-(4-O-acetyl)-alpha-L-rhamnopyranosyl-(1-->4)-beta-D- glucopyranosyl-(1-->6)-beta-D-glucopyranosyl ester (terminal rhamnosyl 4-O-acetate of huzhangoside B); clemastanoside B and C, 3-O-beta-D-xylopyranosyl- and 3-O-beta-D-ribopyranosyl-(1-->3)-alpha-L- rhamnopyranosyl-(1-->2)-beta-D-galactopyranosyl oleanolic acid 28-O-alpha-L-rhamnopyranosyl-(1-->4)-beta-D-glucopyranosyl- (1-->6)-beta-D-glucopyranosyl ester, respectively; clemastanoside D, 3-O-beta-D-ribopyranosyl-(1-->3)-alpha-L-rhamnopyranosyl- (1-->2)-alpha-L-arabinopyranosyl hederagenin 28-O-beta-D-glucopyranosyl ester; clemastanoside E, F and G, terminal rhamnosyl 4-O-, 3-O- and 2-O-acetate of 3-O-beta-D-ribopyranosyl-(1-->3)-alpha-L-rhamnopyranosyl-(1-->2)-a lpha-L- arabinopyranosyl hederagenin 28-O-alpha-L-rhamnopyranosyl-(1-->4)-beta-D-glucopyranosyl-(1-->6)-beta- D- glucopyranosyl ester, respectively; clemastanin A, (7S,8R)-3-methoxy-3',4,9,9'-tetrahydroxy-4',7-epoxy-5',8-lignan 3'-O-beta-D-glucopyranoside; clemastanin B, (+)-lariciresinol 4,4'-O-bis-beta-D-glucopyranoside.

Authors+Show Affiliations

Kizu H
Faculty of Pharmaceutical Sciences, Hokuriku University, Kanazawa, Japan.
Shimana H
No affiliation info available
Tomimori T
No affiliation info available

MeSH

Carbohydrate SequenceFlavonoidsHydrolysisLignansMagnetic Resonance SpectroscopyMolecular Sequence DataPlant RootsPlants, MedicinalSaponins

Pub Type(s)

Journal Article

Language

eng

PubMed ID

8582022

Citation

Kizu, H, et al. "Studies On the Constituents of Clematis Species. VI. the Constituents of Clematis Stans Sieb. Et Zucc." Chemical & Pharmaceutical Bulletin, vol. 43, no. 12, 1995, pp. 2187-94.
Kizu H, Shimana H, Tomimori T. Studies on the constituents of Clematis species. VI. The constituents of Clematis stans Sieb. et Zucc. Chem Pharm Bull (Tokyo). 1995;43(12):2187-94.
Kizu, H., Shimana, H., & Tomimori, T. (1995). Studies on the constituents of Clematis species. VI. The constituents of Clematis stans Sieb. et Zucc. Chemical & Pharmaceutical Bulletin, 43(12), 2187-94.
Kizu H, Shimana H, Tomimori T. Studies On the Constituents of Clematis Species. VI. the Constituents of Clematis Stans Sieb. Et Zucc. Chem Pharm Bull (Tokyo). 1995;43(12):2187-94. PubMed PMID: 8582022.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Studies on the constituents of Clematis species. VI. The constituents of Clematis stans Sieb. et Zucc. AU - Kizu,H, AU - Shimana,H, AU - Tomimori,T, PY - 1995/12/1/pubmed PY - 1995/12/1/medline PY - 1995/12/1/entrez SP - 2187 EP - 94 JF - Chemical & pharmaceutical bulletin JO - Chem Pharm Bull (Tokyo) VL - 43 IS - 12 N2 - 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-beta-D-glucopyranoside, (+)-lariciresinol 4'-O-beta-D-glucopyranoside and (+)-pinoresinol 4,4'-O-bis-beta-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, rutin and quercetin 3-O-beta-D-glucuronopyranoside. The structures of the new compounds were elucidated based on chemical and physicochemical evidence as follows: clemastanoside A, 3-O-beta-D-ribopyranosyl-(1-->3)-alpha-L-rhamnopyranosyl-(1-->2)-a lpha-L- arabinopyranosyl oleanolic acid 28-O-(4-O-acetyl)-alpha-L-rhamnopyranosyl-(1-->4)-beta-D- glucopyranosyl-(1-->6)-beta-D-glucopyranosyl ester (terminal rhamnosyl 4-O-acetate of huzhangoside B); clemastanoside B and C, 3-O-beta-D-xylopyranosyl- and 3-O-beta-D-ribopyranosyl-(1-->3)-alpha-L- rhamnopyranosyl-(1-->2)-beta-D-galactopyranosyl oleanolic acid 28-O-alpha-L-rhamnopyranosyl-(1-->4)-beta-D-glucopyranosyl- (1-->6)-beta-D-glucopyranosyl ester, respectively; clemastanoside D, 3-O-beta-D-ribopyranosyl-(1-->3)-alpha-L-rhamnopyranosyl- (1-->2)-alpha-L-arabinopyranosyl hederagenin 28-O-beta-D-glucopyranosyl ester; clemastanoside E, F and G, terminal rhamnosyl 4-O-, 3-O- and 2-O-acetate of 3-O-beta-D-ribopyranosyl-(1-->3)-alpha-L-rhamnopyranosyl-(1-->2)-a lpha-L- arabinopyranosyl hederagenin 28-O-alpha-L-rhamnopyranosyl-(1-->4)-beta-D-glucopyranosyl-(1-->6)-beta- D- glucopyranosyl ester, respectively; clemastanin A, (7S,8R)-3-methoxy-3',4,9,9'-tetrahydroxy-4',7-epoxy-5',8-lignan 3'-O-beta-D-glucopyranoside; clemastanin B, (+)-lariciresinol 4,4'-O-bis-beta-D-glucopyranoside. SN - 0009-2363 UR - https://www.unboundmedicine.com/medline/citation/8582022/Studies_on_the_constituents_of_Clematis_species__VI__The_constituents_of_Clematis_stans_Sieb__et_Zucc_ DB - PRIME DP - Unbound Medicine ER -