铁线莲属植物成分的研究。VI. 直立铁线莲的成分

Studies on the constituents of Clematis species. VI. The constituents of Clematis stans Sieb. et Zucc.

作者信息

Kizu H, Shimana H, Tomimori T

机构信息

Faculty of Pharmaceutical Sciences, Hokuriku University, Kanazawa, Japan.

出版信息

Chem Pharm Bull (Tokyo). 1995 Dec;43(12):2187-94. doi: 10.1248/cpb.43.2187.

DOI:10.1248/cpb.43.2187

PMID:8582022

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.

摘要

从毛蕊铁线莲的根部分离出了三种新的齐墩果烷型三萜皂苷，分别命名为铁线莲皂苷A、B和C，以及两种新的木脂糖苷，命名为铁线莲素A和B，同时还分离出了三种已知的三萜皂苷，虎杖苷B、C和D，以及三种已知的木脂糖苷，(+)-落叶松脂醇4-O-β-D-吡喃葡萄糖苷、(+)-落叶松脂醇4'-O-β-D-吡喃葡萄糖苷和(+)-松脂醇4,4'-O-双-β-D-吡喃葡萄糖苷。此外，从叶部分离出了四种新的齐墩果烷型三萜皂苷，命名为铁线莲皂苷D、E、F和G，同时还分离出了五种已知的三萜皂苷，常春藤皂苷B、木立皂苷K12、虎杖苷B、七叶皂苷B和虎杖苷D，以及三种已知的黄酮类化合物，异槲皮苷、芦丁和槲皮素3-O-β-D-葡萄糖醛酸苷。基于化学和物理化学证据，新化合物的结构如下：铁线莲皂苷A，3-O-β-D-吡喃核糖基-(1→3)-α-L-吡喃鼠李糖基-(1→2)-α-L-吡喃阿拉伯糖基齐墩果酸28-O-(4-O-乙酰基)-α-L-吡喃鼠李糖基-(1→4)-β-D-吡喃葡萄糖基-(1→6)-β-D-吡喃葡萄糖基酯（虎杖苷B的末端鼠李糖基4-O-乙酸酯）；铁线莲皂苷B和C，分别为3-O-β-D-吡喃木糖基和3-O-β-D-吡喃核糖基-(1→3)-α-L-吡喃鼠李糖基-(1→2)-β-D-吡喃半乳糖基齐墩果酸28-O-α-L-吡喃鼠李糖基-(1→4)-β-D-吡喃葡萄糖基-(1→6)-β-D-吡喃葡萄糖基酯；铁线莲皂苷D，3-O-β-D-吡喃核糖基-(1→3)-α-L-吡喃鼠李糖基-(1→2)-α-L-吡喃阿拉伯糖基常春藤皂苷元28-O-β-D-吡喃葡萄糖基酯；铁线莲皂苷E、F和G，分别为3-O-β-D-吡喃核糖基-(1→3)-α-L-吡喃鼠李糖基-(1→2)-α-L-吡喃阿拉伯糖基常春藤皂苷元28-O-α-L-吡喃鼠李糖基-(1→4)-β-D-吡喃葡萄糖基-(1→6)-β-D-吡喃葡萄糖基酯的末端鼠李糖基4-O-、3-O-和2-O-乙酸酯；铁线莲素A，(7S,8R)-3-甲氧基-3',4,9,9'-四羟基-4',7-环氧-5',8-木脂素3'-O-β-D-吡喃葡萄糖苷；铁线莲素B，(+)-落叶松脂醇4,4'-O-双-β-D-吡喃葡萄糖苷。