从圣草中合成新型儿茶素（2R，3R）-表没食子儿茶素-3-O-（4-羟基苯甲酸酯）及其蛋白酶体抑制活性评估
Synthesis of (2R, 3R)-epigallocatechin-3-O-(4-hydroxybenzoate), a novel catechin from Cistus salvifolius, and evaluation of its proteasome inhibitory activities.
作者信息
Osanai Kumi, Huo Congde, Landis-Piwowar Kristin R, Dou Q Ping, Chan Tak Hang
机构信息
Department of Applied Biology and Chemical Technology and the Open Laboratory for Chiral Technology, the Institute of Molecular Technology for Drug Discovery and Synthesis, The Hong Kong Polytechnic University, Hung Hom, Kowloon, Hong Kong SAR, China.
出版信息
Tetrahedron. 2007 Aug 6;63(32):7565-7570. doi: 10.1016/j.tet.2007.05.043.
Abstract
The total and semi syntheses of (2R, 3R)-epigallocatechin-3-O-(4-hydroxybenzoate), a novel catechin from Cistus salvifolius, was accomplished. The proteasome inhibition and cytotoxic activities of the synthetic compound and its acetyl derivative were studied and compared with (2R, 3R)-epigallocatechin-3-gallate (EGCG), the active component from green tea.
摘要
完成了来自圣栎叶石蚕的新型儿茶素（2R，3R）-表没食子儿茶素-3-O-（4-羟基苯甲酸酯）的全合成和半合成。研究了合成化合物及其乙酰衍生物的蛋白酶体抑制活性和细胞毒性，并与绿茶中的活性成分（2R，3R）-表没食子儿茶素-3-没食子酸酯（EGCG）进行了比较。
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2
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Drug Metab Dispos. 2006 Dec;34(12):2111-6. doi: 10.1124/dmd.106.011460. Epub 2006 Sep 22.
3
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