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山楂叶中的萜类化合物和己烯。

Terpenoids and hexenes from the leaves of Crataegus pinnatifida.

机构信息

School of Traditional Chinese Materia Medica, Key Laboratory of Structure-Based Drug Design and Discovery, Ministry of Education, Shenyang Pharmaceutical University, Shenyang 110016, PR China.

School of Traditional Chinese Materia Medica, Key Laboratory of Structure-Based Drug Design and Discovery, Ministry of Education, Shenyang Pharmaceutical University, Shenyang 110016, PR China.

出版信息

Food Chem. 2011 Dec 1;129(3):933-9. doi: 10.1016/j.foodchem.2011.05.049. Epub 2011 May 14.

Abstract

Crataegus pinnatifida have long been used in traditional Chinese medicine and European herbal medicine, and are widely consumed as food, in the form of juice, drink, jam and canned fruit. Four new compounds, a sesquiterpene and its glycoside (1-2), two monoterpene glycosides (3-4), together with eight known compounds (5-12), were isolated from the leaves of C. pinnatifida. Their structures were elucidated as (5Z)-6-[5-(2-hydroxypropan-2-yl)-2-methyltetrahydrofuran-2-yl]-3-methylhexa-1,5-dien-3-ol (1), (5Z)-6-[5-(2-O-β-d-glucopyranosyl-propan-2-yl)-2-methyl tetrahydrofuran-2-yl]-3-methylhexa-1,5-dien-3-ol (2), 5-ethenyl-2-[2-O-β-d-glucopyranosyl-(1″→6')-β-d-glucopyranosyl-propan-2-yl]-5-methyltetrahydrofuran-2-ol (3), 4-[4β-O-β-d-xylopyranosyl-(1″→6')-β-d-glucopyranosyl-2,6,6-trimethyl-1-cyclohexen-1-yl]-butan-2-one (4), (Z)-3-hexenyl O-β-d-glucopyranosyl-(1″→6')-β-d-glucopyranoside (5), (Z)-3-hexenyl O-β-d-xylopyranosyl-(1″→6')-β-d-glucopyranoside (6), (Z)-3-hexenyl O-β-d-rhamnopyranosyl-(1″→6')-β-d-glucopyranoside (7), (3R,5S,6S,7E,9S)-megastiman-7-ene-3,5,6,9-tetrol (8), (3R,5S,6S,7E,9S)-megastigman-7-ene-3,5,6,9-tetrol9-O-β-d-glucopyranoside (9), (6S,7E,9R)-6,9-dihydroxy-4,7-megastigmadien-3-one 9-O-[β-d-xylopyranosyl-(1″→6')-β-d-glucopyranoside] (10), Linarionoside C (11), and (3S,9R)-3,9-dihydroxy-megastigman-5-ene 3-O-primeveroside (12), using a combination of mass spectroscopy, 1D and 2D NMR spectroscopy and chemical analysis. Cytotoxicity of the new compounds was assayed against selected human glioma (U87) cell lines.

摘要

山茱萸在传统中药和欧洲草药中应用已久,作为食品广泛消费,有果汁、饮料、果酱和罐装水果等形式。从山茱萸叶中分离得到了四个新化合物,一个倍半萜及其糖苷(1-2),两个单萜糖苷(3-4),以及八个已知化合物(5-12)。它们的结构分别鉴定为(5Z)-6-[5-(2-羟基-2-甲基丙烷-2-基)-2-甲基四氢呋喃-2-基]-3-甲基己-1,5-二烯-3-醇(1)、(5Z)-6-[5-(2-O-β-D-吡喃葡萄糖基-2-甲基四氢呋喃-2-基)-2-甲基己-1,5-二烯-3-基]-3-甲基己-1,5-二烯-3-醇(2)、5-乙烯基-2-[2-O-β-D-吡喃葡萄糖基-(1″→6′)-β-D-吡喃葡萄糖基-2-甲基丙烷-2-基]-5-甲基四氢呋喃-2-醇(3)、4-[4β-O-β-D-木吡喃糖基-(1″→6′)-β-D-吡喃葡萄糖基-2,6,6-三甲基-1-环己烯-1-基]-丁-2-酮(4)、(Z)-3-己烯基 O-β-D-吡喃葡萄糖基-(1″→6′)-β-D-吡喃葡萄糖苷(5)、(Z)-3-己烯基 O-β-D-木吡喃糖基-(1″→6′)-β-D-吡喃葡萄糖苷(6)、(Z)-3-己烯基 O-β-D-鼠李吡喃糖基-(1″→6′)-β-D-吡喃葡萄糖苷(7)、(3R,5S,6S,7E,9S)-megastiman-7-ene-3,5,6,9-tetrol(8)、(3R,5S,6S,7E,9S)-megastigman-7-ene-3,5,6,9-tetrol9-O-β-D-吡喃葡萄糖苷(9)、(6S,7E,9R)-6,9-二羟基-4,7-巨麦甾二烯-3-酮 9-O-[β-D-木吡喃糖基-(1″→6′)-β-D-吡喃葡萄糖苷](10)、Linarionoside C(11)和(3S,9R)-3,9-二羟基-巨麦甾烷-5-烯 3-O-primveroside(12),采用质谱、1D 和 2D NMR 光谱和化学分析相结合的方法。对新化合物进行了对选定的人神经胶质瘤(U87)细胞系的细胞毒性测定。

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