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Ligand Binding Affinities of Arctigenin and Its Demethylated Metabolites to Estrogen Receptor Alpha
Institute of Natural Medicine, University of Toyama, 2630 Sugitani, Toyama 930-0194, Japan
College of Pharmacy, Dongduk Women's University, 23-1 Wolgok-Dong, Sungbuk-Gu, Seoul 136-714, Korea
* Author to whom correspondence should be addressed.
Received: 8 October 2012; in revised form: 10 January 2013 / Accepted: 14 January 2013 / Published: 16 January 2013
Abstract: Phytoestrogens are defined as plant-derived compounds with estrogen-like activities according to their chemical structures and activities. Plant lignans are generally categorized as phytoestrogens. It was reported that (−)-arctigenin, the aglycone of arctiin, was demethylated to (−)-dihydroxyenterolactone (DHENL) by Eubacterium (E.) sp. ARC-2. Through stepwise demethylation, E. sp. ARC-2 produced six intermediates, three mono-desmethylarctigenins and three di-desmethylarctigenins. In the present study, ligand binding affinities of (−)-arctigenin and its seven metabolites, including DHENL, were investigated for an estrogen receptor alpha, and found that demethylated metabolites had stronger binding affinities than (−)-arctigenin using a ligand binding screen assay method. The IC50 value of (2R,3R)-2-(4-hydroxy-3-methoxybenzyl)-3-(3,4-dihydroxybenzyl)-butyrolactone was 7.9 × 10−4 M.
Keywords: arctigenin; estrogen receptor alpha; demethylation; ligand binding affinity
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Jin, J.-S.; Lee, J.-H.; Hattori, M. Ligand Binding Affinities of Arctigenin and Its Demethylated Metabolites to Estrogen Receptor Alpha. Molecules 2013, 18, 1122-1127.
Jin J-S, Lee J-H, Hattori M. Ligand Binding Affinities of Arctigenin and Its Demethylated Metabolites to Estrogen Receptor Alpha. Molecules. 2013; 18(1):1122-1127.
Jin, Jong-Sik; Lee, Jong-Hyun; Hattori, Masao. 2013. "Ligand Binding Affinities of Arctigenin and Its Demethylated Metabolites to Estrogen Receptor Alpha." Molecules 18, no. 1: 1122-1127.