Mukai Daisuke, Matsuda Noriko, Yoshioka Yu, Sato Masashi, Yamasaki Toru
Department of Applied Biological Science, Kagawa University, 2393 Miki-Ikenobe, Kagawa, 761-0795, Japan.
J Nat Med. 2008 Apr;62(2):155-9. doi: 10.1007/s11418-007-0201-4. Epub 2008 Jan 18.
A novel gallate of tannin, (-)-epigallocatechin-(2 beta-->O-->7',4 beta-->8')-epicatechin-3'-O-gallate (8), together with (-)-epicatechin-3-O-gallate (4), (-)-epigallocatechin (5), (-)-epigallocatechin-3-O-gallate (6), and (+)-gallocatechin-(4 alpha-->8')-epigallocatechin (7), were isolated from the tea plant Camellia sinensis (L.) O. Kuntze var. sinensis (cv., Yabukita). The structure of 8, including stereochemistry, was elucidated by spectroscopic methods and hydrolysis. The compounds, along with commercially available pyrogallol (1), (+)-catechin (2), and (-)-epicatechin (3), were examined for toxicity towards egg-bearing adults of Caenorhabditis elegans. The anthelmintic mebendazole (9) was used as a positive control. Neither 2 nor 3 were toxic but the other compounds were toxic in the descending order 8, 7 approximately 6, 9, 4, 5, 1. The LC(50) (96 h) values of 8 and 9 were evaluated as 49 and 334 micromol L(-1), respectively. These data show that many green tea polyphenols may be potential anthelmintics.
从茶树中华变种(品种:薮北茶)中分离出一种新型单宁没食子酸盐,即(-)-表没食子儿茶素-(2β→O→7',4β→8')-表儿茶素-3'-O-没食子酸盐(8),以及(-)-表儿茶素-3-O-没食子酸盐(4)、(-)-表没食子儿茶素(5)、(-)-表没食子儿茶素-3-O-没食子酸盐(6)和(+)-没食子儿茶素-(4α→8')-表没食子儿茶素(7)。通过光谱法和水解法阐明了8的结构,包括立体化学结构。研究了这些化合物以及市售的连苯三酚(1)、(+)-儿茶素(2)和(-)-表儿茶素(3)对秀丽隐杆线虫成虫的毒性。以驱虫药甲苯达唑(9)作为阳性对照。2和3均无毒,但其他化合物有毒,毒性从高到低依次为8、7≈6、9、4、5、1。8和9的LC(50)(96小时)值分别评估为49和334微摩尔/升。这些数据表明,许多绿茶多酚可能是潜在的驱虫剂。