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. 2013 Jan 16;18(1):1122-7.
doi: 10.3390/molecules18011122.

Ligand binding affinities of arctigenin and its demethylated metabolites to estrogen receptor alpha

Jong-Sik Jin  1 , Jong-Hyun Lee, Masao Hattori
Affiliations

Ligand binding affinities of arctigenin and its demethylated metabolites to estrogen receptor alpha

Jong-Sik Jin et al. Molecules. .

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.

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Figures

Figure 1
Figure 1
Arctigenin and its metabolites by E. sp. ARC-2.
See this image and copyright information in PMC

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