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Nutrients 2018, 10(12), 1915; https://doi.org/10.3390/nu10121915

Isoamericanoic Acid B from Acer tegmentosum as a Potential Phytoestrogen

1
School of Pharmacy, Sungkyunkwan University, Suwon 16419, Korea
2
Department of Food and Nutrition, Gachon University, Seongnam 13120, Korea
*
Authors to whom correspondence should be addressed.
Received: 15 September 2018 / Revised: 20 November 2018 / Accepted: 28 November 2018 / Published: 4 December 2018
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Abstract

Phytoestrogens derived from plants have attracted the attention of the general public and the medical community due to their potentially beneficial role in relieving menopausal symptoms. The deciduous tree Acer tegmentosum Maxim (Aceraceae) has long been utilized in Korean folk medicine to alleviate many physiological disorders, including abscesses, surgical bleeding, and liver diseases. In order to explore structurally and/or biologically new constituents from Korean medicinal plants, a comprehensive phytochemical study was carried out on the bark of A. tegmentosum. One new phenolic compound with a 1,4-benzodioxane scaffold, isoamericanoic acid B (1), as well as with nine known phenolic compounds (210), were successfully isolated from the aqueous extracts of the bark of A. tegmentosum. A detailed analysis using 1D and 2D NMR spectroscopy, electronic circular dichroism (ECD) spectral data, and LC/MS afforded the unambiguous structural determination of all isolated compounds, including the new compound 1. In addition, compounds 2, 4, 5, and 9 were isolated and identified from the bark of A. tegmentosum for the first time. All isolated compounds were tested for their estrogenic activities using an MCF-7 BUS cell proliferation assay, which revealed that compounds 1, 2, and 10 showed moderate estrogenic activity. To study the mechanism of this estrogenic effect, a docking simulation of compound 1, which showed the best estrogenic activity, was conducted with estrogen receptor (ER) -α and ER-β, which revealed that it interacts with the key residues of ER-α and ER-β. In addition, compound 1 had slightly higher affinity for ER-β than ER-α in the calculated Gibbs free energy for 1:ER-α and 1:ER-β. Thus, the present experimental evidence demonstrated that active compound 1 from A. tegmentosum could be a promising phytoestrogen for the development of natural estrogen supplements. View Full-Text
Keywords: Acer tegmentosum; phenolic compounds; 1,4-benzodioxane scaffold; estrogen; phytoestrogens; molecular docking Acer tegmentosum; phenolic compounds; 1,4-benzodioxane scaffold; estrogen; phytoestrogens; molecular docking
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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 (CC BY 4.0).

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Lee, S.R.; Park, Y.J.; Han, Y.B.; Lee, J.C.; Lee, S.; Park, H.-J.; Lee, H.-J.; Kim, K.H. Isoamericanoic Acid B from Acer tegmentosum as a Potential Phytoestrogen. Nutrients 2018, 10, 1915.

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