<?xml version="1.0" encoding="UTF-8"?><xml><records><record><source-app name="Biblio" version="7.x">Drupal-Biblio</source-app><ref-type>17</ref-type><contributors><authors><author><style face="normal" font="default" size="100%">Brennan, J.C.a</style></author><author><style face="normal" font="default" size="100%">Denison, M.S.a</style></author><author><style face="normal" font="default" size="100%">Holstege, D.M.b</style></author><author><style face="normal" font="default" size="100%">Magiatis, P.c</style></author><author><style face="normal" font="default" size="100%">Dallas, J.L.d</style></author><author><style face="normal" font="default" size="100%">Gutierrez, E.G.e</style></author><author><style face="normal" font="default" size="100%">Soshilov, A.A.a</style></author><author><style face="normal" font="default" size="100%">Millam, J.R.f</style></author></authors></contributors><titles><title><style face="normal" font="default" size="100%">2,3-cis-2R,3R-(-)-epiafzelechin-3-O-p-coumarate, a novel flavan-3-ol isolated from Fallopia convolvulus seed, is an estrogen receptor agonist in human cell lines</style></title><secondary-title><style face="normal" font="default" size="100%">BMC Complementary and Alternative Medicine</style></secondary-title></titles><keywords><keyword><style  face="normal" font="default" size="100%">2</style></keyword><keyword><style  face="normal" font="default" size="100%">3 epiafzelechin 3 o 4 coumarate</style></keyword><keyword><style  face="normal" font="default" size="100%">article</style></keyword><keyword><style  face="normal" font="default" size="100%">biological activity</style></keyword><keyword><style  face="normal" font="default" size="100%">Breast Carcinoma</style></keyword><keyword><style  face="normal" font="default" size="100%">cancer cell culture</style></keyword><keyword><style  face="normal" font="default" size="100%">carcinoma cell</style></keyword><keyword><style  face="normal" font="default" size="100%">Cell Line</style></keyword><keyword><style  face="normal" font="default" size="100%">chemical analysis</style></keyword><keyword><style  face="normal" font="default" size="100%">Chinese Herbal</style></keyword><keyword><style  face="normal" font="default" size="100%">circular dichroism</style></keyword><keyword><style  face="normal" font="default" size="100%">controlled study</style></keyword><keyword><style  face="normal" font="default" size="100%">drug identification</style></keyword><keyword><style  face="normal" font="default" size="100%">drug isolation</style></keyword><keyword><style  face="normal" font="default" size="100%">drug potency</style></keyword><keyword><style  face="normal" font="default" size="100%">Drugs</style></keyword><keyword><style  face="normal" font="default" size="100%">emodin</style></keyword><keyword><style  face="normal" font="default" size="100%">Estradiol</style></keyword><keyword><style  face="normal" font="default" size="100%">estrogen activity</style></keyword><keyword><style  face="normal" font="default" size="100%">estrogen receptor</style></keyword><keyword><style  face="normal" font="default" size="100%">estrogen receptor alpha</style></keyword><keyword><style  face="normal" font="default" size="100%">estrogen receptor beta</style></keyword><keyword><style  face="normal" font="default" size="100%">Fallopia</style></keyword><keyword><style  face="normal" font="default" size="100%">Fallopia convolvulus</style></keyword><keyword><style  face="normal" font="default" size="100%">Female</style></keyword><keyword><style  face="normal" font="default" size="100%">flavan derivative</style></keyword><keyword><style  face="normal" font="default" size="100%">Flavonoids</style></keyword><keyword><style  face="normal" font="default" size="100%">gene activity</style></keyword><keyword><style  face="normal" font="default" size="100%">gene induction</style></keyword><keyword><style  face="normal" font="default" size="100%">genetic transfection</style></keyword><keyword><style  face="normal" font="default" size="100%">genistein</style></keyword><keyword><style  face="normal" font="default" size="100%">high performance liquid chromatography</style></keyword><keyword><style  face="normal" font="default" size="100%">human</style></keyword><keyword><style  face="normal" font="default" size="100%">human cell</style></keyword><keyword><style  face="normal" font="default" size="100%">human cell culture</style></keyword><keyword><style  face="normal" font="default" size="100%">Humans</style></keyword><keyword><style  face="normal" font="default" size="100%">in vitro study</style></keyword><keyword><style  face="normal" font="default" size="100%">ion cyclotron resonance mass spectrometry</style></keyword><keyword><style  face="normal" font="default" size="100%">liquid chromatography</style></keyword><keyword><style  face="normal" font="default" size="100%">Molecular Structure</style></keyword><keyword><style  face="normal" font="default" size="100%">Nuclear magnetic resonance spectroscopy</style></keyword><keyword><style  face="normal" font="default" size="100%">optical rotation</style></keyword><keyword><style  face="normal" font="default" size="100%">ovary carcinoma</style></keyword><keyword><style  face="normal" font="default" size="100%">phytochemistry</style></keyword><keyword><style  face="normal" font="default" size="100%">phytoestrogen</style></keyword><keyword><style  face="normal" font="default" size="100%">Phytoestrogens</style></keyword><keyword><style  face="normal" font="default" size="100%">plant seed</style></keyword><keyword><style  face="normal" font="default" size="100%">Polygonaceae</style></keyword><keyword><style  face="normal" font="default" size="100%">Protein Binding</style></keyword><keyword><style  face="normal" font="default" size="100%">reporter gene</style></keyword><keyword><style  face="normal" font="default" size="100%">Seeds</style></keyword><keyword><style  face="normal" font="default" size="100%">stereochemistry</style></keyword><keyword><style  face="normal" font="default" size="100%">tandem mass spectrometry</style></keyword><keyword><style  face="normal" font="default" size="100%">Tumor</style></keyword><keyword><style  face="normal" font="default" size="100%">unclassified drug</style></keyword></keywords><dates><year><style  face="normal" font="default" size="100%">2013</style></year></dates><urls><web-urls><url><style face="normal" font="default" size="100%">http://www.scopus.com/inward/record.url?eid=2-s2.0-84878894926&amp;partnerID=40&amp;md5=6a252a5013347ea23868213aa22f4b59</style></url></web-urls></urls><volume><style face="normal" font="default" size="100%">13</style></volume><language><style face="normal" font="default" size="100%">eng</style></language><abstract><style face="normal" font="default" size="100%">Background: The plant genus Fallopia is well-known in Chinese traditional medicine and includes many species that contain bioactive compounds, namely phytoestrogens. Consumption of phytoestrogens may be linked to decreased incidence of breast and prostate cancers therefore discovery of novel phytoestrogens and novel sources of phytoestrogens is of interest. Although phytoestrogen content has been analyzed in the rhizomes of various Fallopia sp., seeds of a Fallopia sp. have never been examined for phytoestrogen presence.Methods: Analytical chemistry techniques were used with guidance from an in vitro estrogen receptor bioassay (a stably transfected human ovarian carcinoma cell line) to isolate and identify estrogenic components from seeds of Fallopia convolvulus. A transiently transfected human breast carcinoma cell line was used to characterize the biological activity of the isolated compounds on estrogen receptors (ER) α and β.Results: Two compounds, emodin and the novel flavan-3-ol, (-)-epiafzelechin-3-O-p-coumarate (rhodoeosein), were identified to be responsible for estrogenic activity of F. convolvulus seed extract. Absolute stereochemistry of rhodoeosein was determined by 1 and 2D NMR, optical rotation and circular dichroism. Emodin was identified by HPLC/DAD, LC/MS/MS, and FT/ICR-MS. When characterizing the ER specificity in biological activity of rhodoeosein and emodin, rhodoeosein was able to exhibit a four-fold greater relative estrogenic potency (REP) in breast cells transiently-transfected with ERβ as compared to those transfected with ERα, and emodin exhibited a six-fold greater REP in ERβ-transfected breast cells. Cell type-specific differences were observed with rhodoeosein but not emodin; rhodoeosein produced superinduction of reporter gene activity in the human ovarian cell line (&gt; 400% of maximum estradiol [E2] induction) but not in the breast cell line.Conclusion: This study is the first to characterize the novel flavan-3-ol compound, rhodoeosein, and its ability to induce estrogenic activity in human cell lines. Rhodoeosein and emodin may have potential therapeutic applications as natural products activating ERβ, and further characterization of rhodoeosein is necessary to evaluate its selectivity as a cell type-specific ER agonist. © 2013 Brennan et al.; licensee BioMed Central Ltd.</style></abstract><notes><style face="normal" font="default" size="100%">cited By (since 1996)0</style></notes></record></records></xml>