Next Article in Journal
Effects of Protein Supplementation Combined with Exercise Intervention on Frailty Indices, Body Composition, and Physical Function in Frail Older Adults
Previous Article in Journal
Three-Year Chronic Consumption of Low-Carbohydrate Diet Impairs Exercise Performance and Has a Small Unfavorable Effect on Lipid Profile in Middle-Aged Men
Open AccessCommunication

Isoamericanoic Acid B from Acer tegmentosum as a Potential Phytoestrogen

School of Pharmacy, Sungkyunkwan University, Suwon 16419, Korea
Department of Food and Nutrition, Gachon University, Seongnam 13120, Korea
Authors to whom correspondence should be addressed.
Nutrients 2018, 10(12), 1915;
Received: 15 September 2018 / Revised: 20 November 2018 / Accepted: 28 November 2018 / Published: 4 December 2018
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
Show Figures

Graphical abstract

MDPI and ACS Style

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.

Show more citation formats Show less citations formats
Note that from the first issue of 2016, MDPI journals use article numbers instead of page numbers. See further details here.

Article Access Map by Country/Region

Back to TopTop