Matsuda H, Shimoda H, Morikawa T, Yoshikawa M
Kyoto Pharmaceutical University, Misasagi, Yamashina-ku, 607-8412, Kyoto, Japan.
Bioorg Med Chem Lett. 2001 Jul 23;11(14):1839-42. doi: 10.1016/s0960-894x(01)00318-3.
The methanolic extract from the roots of Polygonum (P.) cuspidatum was found to enhance cell proliferation at 30 or 100 microg/mL in MCF-7, an estrogen-sensitive cell line. By bioassay-guided separation from P. cuspidatum with the most potent activity, emodin and emodin 8-O-beta-D-glucopyranoside were isolated as active principles. The methanolic extracts from Polygonum, Cassia, Aloe, and Rheum species, which were known to contain anthraquinones, also showed the MCF-7 proliferation. As a result of the evaluation of various anthraquinones from plant sources and synthetic anthraquinones, aloe-emodin, chrysophanol, chrysophanol 8-O-beta-D-glucopyranoside, and 1,8-dihydroxyanthraquinone showed weak activity. On the other hand, alizalin and 2,6-dihydroxyanthraquinone as well as emodin having the 2- and/or 6-hydroxyl groups showed potent activity. These results show that the unchelated hydroxyl group is essential for strong activity. Emodin and 2,6-dihydroxyanthraquinone also inhibited 17beta-estradiol binding to human estrogen receptors (ERs) with K(i) values of 0.77 and 0.31microM for ERalpha and 1.5 and 0.69 microM for ERbeta. These findings indicate that hydroxyanthraquinones such as emodin are phytoestrogens with an affinity to human estrogen receptors.
虎杖根的甲醇提取物在雌激素敏感细胞系MCF-7中，于30或100微克/毫升时可增强细胞增殖。通过对活性最强的虎杖进行生物测定导向分离，大黄素和大黄素8-O-β-D-吡喃葡萄糖苷被分离为活性成分。已知含有蒽醌类化合物的蓼属、决明属、芦荟属和大黄属植物的甲醇提取物，也显示出对MCF-7的增殖作用。对来自植物来源的各种蒽醌类化合物和合成蒽醌类化合物进行评估的结果表明，芦荟大黄素、大黄酚、大黄酚8-O-β-D-吡喃葡萄糖苷和1,8-二羟基蒽醌显示出较弱的活性。另一方面，具有2-和/或6-羟基的茜草素、2,6-二羟基蒽醌以及大黄素显示出较强的活性。这些结果表明，未螯合的羟基对于强活性至关重要。大黄素和2,6-二羟基蒽醌还抑制17β-雌二醇与人雌激素受体（ERs）的结合，对于ERα，其K(i)值分别为0.77和0.31微摩尔，对于ERβ，其K(i)值分别为1.5和0.69微摩尔。这些发现表明，大黄素等羟基蒽醌类化合物是对人雌激素受体具有亲和力的植物雌激素。
