Abstract
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.
References
May 1, 1988·Chemical & Pharmaceutical Bulletin·F KiuchiG Nonaka
Oct 1, 1986·Parasitology·J L Bennett, R A Pax
Jan 1, 1995·Methods in Cell Biology·J B Rand, C D Johnson
Aug 24, 1999·Veterinary Parasitology·T G GearyD P Thompson
Feb 26, 2000·Journal of Natural Products·C MaH Yu
Feb 24, 2001·Phytochemistry·A L BarreirosJ M David
Sep 6, 2003·Trends in Parasitology·John Horton
Citations
Apr 12, 2008·Journal of Natural Medicines·Masashi SatoKen Izumori
Jan 5, 2010·Chemical & Pharmaceutical Bulletin·Masashi SatoToru Yamasaki
Mar 15, 2014·PloS One·Yan QiaoDayong Wang
Feb 2, 2012·Drug and Chemical Toxicology·Sean D StoweJohn Cavanagh
Mar 5, 2013·Journal of Hazardous Materials·ZhenYang YuHuiPing Deng
Apr 27, 2011·Journal of Environmental Sciences (China)·Zhenyang YuDaqiang Yin
Jun 9, 2009·Mechanisms of Ageing and Development·Nadine SaulChristian E W Steinberg
Jul 9, 2010·Acta Tropica·V LakshmiP K Murthy
Dec 3, 2014·Ecotoxicology and Environmental Safety·ZhenYang YuHuiPing Deng
Oct 30, 2012·Veterinary Parasitology·Luciana M KatikiAlessandro F T Amarante
May 4, 2015·Journal of Invertebrate Pathology·Itamar GlazerSergeYan Landau
Jun 16, 2015·Oxidative Medicine and Cellular Longevity·Christian BüchterWim Wätjen
Apr 21, 2017·Natural Product Reports·V SpieglerA Hensel
May 10, 2017·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Jacqueline Dikti VildinaDieudonne Ndjonka
Mar 26, 2014·Blood·Luisa DiomedeGiampaolo Merlini
Mar 19, 2020·Biomolecules·Maoxuan LiuWalter Luyten
Mar 23, 2017·Evidence-based Complementary and Alternative Medicine : ECAM·Hong-Fang JiangWei-Ming Zhang