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[来自密花羊蹄甲亚种的酚酸衍生物]

[Phenolic acid derivatives from Bauhinia glauca subsp. pernervosa].

作者信息

Zhao Qiao-Li, Wu Zeng-Bao, Zheng Zhi-Hui, Lu Xin-Hua, Liang Hong, Cheng Wei, Zhang Qing-Ying, Zhao Yu-Ying

机构信息

State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Beijing 100191, China.

出版信息

Yao Xue Xue Bao. 2011 Aug;46(8):946-50.

PMID:22007520
Abstract

To study the chemical constituents of Bauhinia glauca subsp. pernervosa, eleven phenolic acids were isolated from a 95% ethanol extract by using a combination of various chromatographic techniques including column chromatography over silica gel, ODS, MCI, Sephadex LH-20, and semi-preparative HPLC. By spectroscopic techniques including 1H NMR, 13C NMR, 2D NMR, and HR-ESI-MS, these compounds were identified as isopropyl O-beta-(6'-O-galloyl)-glucopyranoside (1), ethyl O-beta-(6'-O-galloyl)-glucopyranoside (2), 3, 4, 5-trimethoxyphenyl-(6'-O-galloyl)-O-beta-D-glucopyranoside (3), 3, 4, 5-trimethoxyphenyl-beta-D-glucopyranoside (4), gallic acid (5), methyl gallate (6), ethyl gallate (7), protocatechuic acid (8), 3, 5-dimethoxy-4-hydroxybenzoic acid (9), erigeside C (10) and glucosyringic acid (11). Among them, compound 1 is a new polyhydroxyl compound; compounds 2, 10, and 11 were isolated from the genus Bauhinia for the first time, and the other compounds were isolated from the plant for the first time. Compounds 6 and 8 showed significant protein tyrosine phosphatase1B (PTP1B) inhibitory activity in vitro with the IC50 values of 72.3 and 54.1 micromol x L(-1), respectively.

摘要

为研究光叶羊蹄甲亚种显脉羊蹄甲的化学成分,采用硅胶柱色谱、ODS柱色谱、MCI柱色谱、葡聚糖凝胶LH - 20柱色谱及半制备高效液相色谱等多种色谱技术相结合的方法,从95%乙醇提取物中分离得到11种酚酸。通过¹H NMR、¹³C NMR、二维核磁共振及高分辨电喷雾电离质谱等光谱技术,将这些化合物鉴定为异丙基O - β - (6'-O - 没食子酰基)-吡喃葡萄糖苷(1)、乙基O - β - (6'-O - 没食子酰基)-吡喃葡萄糖苷(2)、3,4,5 - 三甲氧基苯基-(6'-O - 没食子酰基)-O - β - D - 吡喃葡萄糖苷(3)、3,4,5 - 三甲氧基苯基-β - D - 吡喃葡萄糖苷(4)没食子酸(5)、没食子酸甲酯(6)、没食子酸乙酯(7)、原儿茶酸(8)、3,5 - 二甲氧基-4 - 羟基苯甲酸(9)、毛地黄糖苷C(10)和葡萄糖基紫丁香酸(11)。其中,化合物1是一种新的多羟基化合物;化合物2、10和11首次从羊蹄甲属植物中分离得到,其他化合物首次从该植物中分离得到。化合物6和8在体外显示出显著的蛋白酪氨酸磷酸酶1B(PTP1B)抑制活性,IC50值分别为72.3和54.1 μmol·L⁻¹。

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