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Molecules 2013, 18(1), 1122-1127; doi:10.3390/molecules18011122
Communication

Ligand Binding Affinities of Arctigenin and Its Demethylated Metabolites to Estrogen Receptor Alpha

1, 2 and 1,*
Received: 8 October 2012 / Revised: 10 January 2013 / Accepted: 14 January 2013 / Published: 16 January 2013
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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 arctigenin; estrogen receptor alpha; demethylation; ligand binding affinity
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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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.

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