@article {Brennan2013,
	title = {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},
	journal = {BMC Complementary and Alternative Medicine},
	volume = {13},
	year = {2013},
	note = {cited By (since 1996)0},
	abstract = {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 (> 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. {\textcopyright} 2013 Brennan et al.; licensee BioMed Central Ltd.},
	keywords = {2, 3 epiafzelechin 3 o 4 coumarate, article, biological activity, Breast Carcinoma, cancer cell culture, carcinoma cell, Cell Line, chemical analysis, Chinese Herbal, circular dichroism, controlled study, drug identification, drug isolation, drug potency, Drugs, emodin, Estradiol, estrogen activity, estrogen receptor, estrogen receptor alpha, estrogen receptor beta, Fallopia, Fallopia convolvulus, Female, flavan derivative, Flavonoids, gene activity, gene induction, genetic transfection, genistein, high performance liquid chromatography, human, human cell, human cell culture, Humans, in vitro study, ion cyclotron resonance mass spectrometry, liquid chromatography, Molecular Structure, Nuclear magnetic resonance spectroscopy, optical rotation, ovary carcinoma, phytochemistry, phytoestrogen, Phytoestrogens, plant seed, Polygonaceae, Protein Binding, reporter gene, Seeds, stereochemistry, tandem mass spectrometry, Tumor, unclassified drug},
	issn = {14726882},
	doi = {10.1186/1472-6882-13-133},
	url = {http://www.scopus.com/inward/record.url?eid=2-s2.0-84878894926\&partnerID=40\&md5=6a252a5013347ea23868213aa22f4b59},
	author = {Brennan, J.C.a and Denison, M.S.a and Holstege, D.M.b and Magiatis, P.c and Dallas, J.L.d and Gutierrez, E.G.e and Soshilov, A.A.a and Millam, J.R.f}
}
