Laboratory of Microbiology and Host Defenses, School of Food and Nutritional Sciences, University of Shizuoka, 52-1 Yada, Suruga-ku, Shizuoka 422-8526, Japan.
Environ Toxicol Pharmacol. 2007 Jan;23(1):121-8. doi: 10.1016/j.etap.2006.07.011. Epub 2006 Aug 4.
Estrogenic chemicals are widely reported to be present in the environment. Their chlorinated derivatives are considered to be produced through the chlorination process in water purification and sewage treatment plants. In this study, several chlorinated derivatives of estrogens and flavonoids, including phytoestrogens, were synthesized by the reaction with hypochlorous acid, and their estrogenic activities were investigated using a devised GFP expression system in human breast carcinoma MCF7 cells. The chlorinated derivatives were less estrogenic than the parent compounds. The EC(50) ranking of estrogen-related compounds was 17β-estradiol (E2)>4-ClE2>estrone (E1)>4-ClE1>10-Cl-1,4-estradiene-3,17-dione (10-Cl-3,17-dione)>2-ClE2>2-ClE1. 2,4-diClE2, 2,4-diClE1, and 2,4,16,16-tetraClE1 showed lower or no estrogenic activity. Genistein and daidzein are well known as phytoestrogens. 6,8-diCl-genistein, 3',8-diCl-daidzein, (+)-6,8-diCl-naringenin, and 6,8-diCl-apigenin showed lower estrogenic activity than their parent compounds. 3',5',8-triCl-daidzein exhibited no estrogenic activity. No activity was detected in chrysin, (+)-catechin, and their chlorinated derivatives. Similar results were obtained in a cell proliferation assay using MCF7 cells.
环境中广泛存在着具有雌激素性质的化学物质。其氯化衍生物被认为是通过水净化和污水处理厂的氯化过程产生的。在这项研究中，通过与次氯酸反应，合成了几种雌激素和类黄酮的氯化衍生物，包括植物雌激素，并在人乳腺癌 MCF7 细胞中使用设计的 GFP 表达系统研究了它们的雌激素活性。氯化衍生物的雌激素活性低于母体化合物。与雌激素相关的化合物的 EC50 排序为 17β-雌二醇（E2）>4-ClE2>雌酮（E1）>4-ClE1>10-Cl-1,4-雌二烯-3,17-二酮（10-Cl-3,17-二酮）>2-ClE2>2-ClE1。2,4-二 ClE2、2,4-二 ClE1 和 2,4,16,16-四 ClE1 表现出较低或没有雌激素活性。染料木黄酮和大豆黄素是众所周知的植物雌激素。6,8-二 Cl-染料木黄酮、3',8-二 Cl-大豆黄素、（+）-6,8-二 Cl-柚皮素和 6,8-二 Cl-芹菜素的雌激素活性低于其母体化合物。3',5',8-三 Cl-大豆黄素没有雌激素活性。在白杨素、（+）-儿茶素及其氯化衍生物中没有检测到活性。在使用 MCF7 细胞的细胞增殖测定中也得到了类似的结果。
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