title: Ligand binding affinities of arctigenin and its demethylated metabolites to estrogen receptor alpha.
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 IC(50) value of (2R,3R)-2-(4-hydroxy-3-methoxybenzyl)-3-(3,4-dihydroxybenzyl)-butyrolactone was 7.9 × 10⁻⁴ M.
authors: Institute of Natural Medicine, University of Toyama, 2630 Sugitani, Toyama 930-0194, Japan.
authors: Jong-Sik
authors: JS
authors: Jin
authors: Jong-Hyun
authors: JH
authors: Lee
authors: Masao
authors: M
authors: Hattori
mesh_terms: D015107:4-Butyrolactone / Q000031:analogs & derivatives* / Q000737:chemistry; D001667:Binding, Competitive; D004958:Estradiol / Q000737:chemistry; D047628:Estrogen Receptor alpha / Q000737:chemistry*; D005663:Furans / Q000737:chemistry*; D006801:Humans; D055767:Immobilized Proteins / Q000737:chemistry; D008024:Ligands; D017705:Lignans / Q000737:chemistry*; D008745:Methylation; D048789:Phytoestrogens / Q000737:chemistry*
chemical_list: D047628:Estrogen Receptor alpha; D005663:Furans; D055767:Immobilized Proteins; D008024:Ligands; D017705:Lignans; D048789:Phytoestrogens; C581691:dihydroxyenterolactone; D004958:Estradiol; D015107:4-Butyrolactone; C071942:arctigenin