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A Computational Modeling of the Structure, Frontier Molecular Orbital (FMO) Analysis, and Global and Local Reactive Descriptors of a Phytochemical ‘Coumestrol’
Published in Nazmul Islam, Satya Bir Singh, Prabhat Ranjan, A. K. Haghi, Mathematics Applied to Engineering in Action, 2021
P. Vinduja, Vijisha K. Rajan, Swathi Krishna, K. Muraleedharan
Structurally similar groups like isoflavones, isoflavanones, isoflavans, pterocarpans, rotenoids come under the class of isoflavanoids [2]. Coumestrol is an important member of the family of natural compounds namely phytoestrogens [3]. Phytoestrogens are the compounds with estrogenic activity which are derived from plants which consist of compounds such as Isoflavones (genistein and diadzein), Coumestans (Coumestrol), lignans (enterolactone and enterodiol), and stilbenes (resveratrol). Coumestans are the phytochemical from where the Coumestrol can be derived. Coumestrol is mostly found in leguminous plants such as Alfalfas [4], ladino clover [5, 6] Chinese herb such as Radix Puerariae and also in plants such as Soybean [7], Brussels, sprouts, spinach, peas, and beans [8], strawberry [9], etc. It has same structure as that of isoflavones and estradiol. Based on the estrogen levels in the body, it shows different estrogenic and anti-estrogenic activities. Estrogenic activity of Coumestrol is due to its stilbene like structure analogs to that of diethylstilbestrol [10].
Steroids: Arthritis, Fertility, Heart Attacks, And Home Run Records
Published in Richard J. Sundberg, The Chemical Century, 2017
There are also plant sources of estrogens, the so-called phytoestrogens such as genistein, daidzein, and coumestrol. These are present mainly in legumes and are found in various soy products. Genistein and daidzein are called isoflavones. Coumestrol is a coumestan and is present in soybean and alfalfa sprouts. Among the soy phytoestrogens, the estrogenic activity of daidzein is about 5 × 10−2 relative to estradiol. At the present time, there is little direct evidence as to whether these substances cause any beneficial or harmful effects.20 There are related compounds known as lignans such as matairesinol and lariciresinol. Typical structures are shown in Scheme 15.4. These compounds have general structural similarity to estradiol and exhibit in vitro binding to estrogen receptors. Humans can be exposed to these compounds through food sources. In particular, it is suggested that infants fed on soy formula milk may be exposed to significant levels.21 Reputed beneficial effects of soy-rich diets have also fueled interest in dietary supplements containing these compounds.
Human exposure to synthetic endocrine disrupting chemicals (S-EDCs) is generally negligible as compared to natural compounds with higher or comparable endocrine activity. How to evaluate the risk of the S-EDCs?
Published in Journal of Toxicology and Environmental Health, Part A, 2020
Herman Autrup, Frank A. Barile, Sir Colin Berry, Bas J. Blaauboer, Alan Boobis, Herrmann Bolt, Christopher J. Borgert, Wolfgang Dekant, Daniel Dietrich, Jose L. Domingo, Gio Batta Gori, Helmut Greim, Jan Hengstler, Sam Kacew, Hans Marquardt, Olavi Pelkonen, Kai Savolainen, Pat Heslop-Harrison, Nico P. Vermeulen
In addition to the studies of Golden, Gandy, and Vollmer (2005), Witorsch (2002), Witorsch and Thomas (2010) who demonstrated that natural or synthetic hormones such as ethinyl estradiol are 10,000 to 1,000,000 fold more potent than S-EDCs, Nohynek et al. (2013) compared the estrogenic potencies of ethinyl estradiol (1,000,000), coumestrol (10,000), genistein (37), butylparaben (0.5), and benzylpareben (0.1) in the rodent uterotrophic assay (Table 1) (Golden, Gandy, and Vollmer 2005; Nilsson 2000; Witorsch and Thomas 2010).