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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.
Sources of Endocrine Disrupters
Published in Jason W. Birkett, John N. Lester, Endocrine Disrupters in Wastewater and Sludge Treatment Processes, 2002
Phytoestrogens are plant-derived compounds that possess estrogenic activity. The term phytoestrogen is used to define a class of compounds that are nonsteroidal and are generally of plant origin, or are produced by the in vivo metabolism of precursors that are present in several plants consumed by humans.32 This metabolism process results in the production of heterocyclic phenols, with a structure similar to the steroid estrogens.33 Isoflavones and lignans are the two main classes of these compounds. The main source of phytoestrogens is food. Isoflavones are found in a variety of plants, including fruits and vegetables, and are especially abundant in soy products.34 Lignans are present in whole grains, legumes, vegetables, and seeds, with high concentrations of lignans found in flaxseed. Table 2.4 indicates the main food sources for both these phytoestrogens.
Steroid hormones in surface water resources in China: systematic review and meta-analysis and probabilistic ecological risk assessment
Published in International Journal of Environmental Health Research, 2023
Xiaomei Hui, Yadolah Fakhri, Zoha Heidarinejad, Vahid Ranaei, Hasti Daraei, Fereshteh Mehri, Intissar Limam, Van Nam Thai
Natural endocrine hormones of estrone (E1), 17β-estradiol (17β-E2), estriol (E3), and several metabolites are sorted as animal estrogens. These estrogens are excreted by mammals and control many physiological processes (Bhandari et al. 2019; Deli et al. 2020). Plants also produce estrogens like isoflavone, coumarol and lignin, which are phytoestrogens. Hormones, including androgens, estrogens, and its main representatives of ethinylestradiol and levonorgestrel, are synthetically produced for human and veterinary pharmaceuticals. For example, testosterone, as an androgen is used to promote strength and muscle mass, and estrogens, are used as contraceptives, multiple pesticides, industrial additives, and in hormone replacement therapy (menopausal hormone therapy) for cancers (Bhandari et al. 2019; Deli et al. 2020). It is worth mentioning that many chemically synthesized medicines (ethinylestradiol, diethylstilbestrol, etc.), chemically synthesized pesticides (dichlorodiphenyltrichloroethane, alachlor, benomyl, endosulfan, carbofuran, linuron, etc.) chemical raw materials and products (polychlorinated biphenyls, nonylphenol, octylphenol, etc.) and environmental pollutants (mycotoxins, dioxins, polycyclic aromatic hydrocarbons, etc.) exhibit estrogenic activities (Ghaffari et al. 2021; Nematollahi et al. 2021; Zoghi et al. 2022).
Urinary Isoflavones Levels in Relation to Serum Thyroid Hormone Concentrations in Female and Male Adults in the U.S. General Population
Published in International Journal of Environmental Health Research, 2021
Patricia A. Janulewicz, Jeffrey M. Carlson, Amelia K. Wesselink, Lauren A. Wise, Elizabeth E. Hatch, Lariah M. Edwards, Junenette L. Peters
Phytoestrogens are plant-derived compounds primarily found in soy products, and at lower levels in legumes, fruits, vegetables, nuts, and coffee. They are also consumed as over-the-counter supplements (Alves et al. 2010; Patisaul and Jefferson 2010). Phytoestrogens belong to a class of compounds known as endocrine-disrupting compounds (EDC), which are natural or synthetic compounds that interfere with the normal function of the endocrine system (US EPA 2015 Aug 10). There are several classes of phytoestrogens, including isoflavones, coumestans, and lignans. Of the isoflavone class, the two most extensively-studied are daidzein and genistein (Adlercreutz and Mazur 1997). These phytoestrogens are also the most biologically-active and estrogenic phytochemicals (Soni et al. 2016). The production of metabolites of daidzein, O-desmethylangolensin (O-DMA) and/or equol, vary by individual (Patisaul and Jefferson 2010). Approximately 80-90% of individuals metabolize daidzein to O-DMA, whereas 30-50% metabolize daidzein to equol (Atkinson et al. 2005).
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 a comprehensive review, Rietjens, Louisse, and Beekmann (2017) evaluated the potential health effects of dietary phytoestrogens. The structural similarity to 17β-estradiol enables phytoestrogens to induce (anti)estrogenic effects by binding to the estrogen receptors (vide supra). Various beneficial health effects have been ascribed to phytoestrogen intake, e.g., a lowered risk of menopausal symptoms like hot flushes and osteoporosis, lowered risks of cardiovascular disease, obesity, metabolic syndrome and type 2 diabetes, brain function disorders, breast cancer, prostate cancer, bowel cancer, and other cancers. However, the (anti)estrogenic properties of phytoestrogens also raised concerns that they might act as N-EDCs, thus having a potential to cause adverse health effects. The latter is somewhat of a misconception as the beneficial effects of phytoestrogens noted can clearly be ascribed to their endocrine activity, meaning that their beneficial effects should be considered as a consequence of their capabilities to affect the endocrine system. The literature overview presented illustrates that several potential health benefits of phytoestrogens have been reported but that, given the data on potential adverse health effects, the current evidence on these beneficial health effects is so obvious that they clearly outweigh the possible health risks. Furthermore, the data currently available are not sufficient to support a more refined (semi) quantitative risk-benefit analysis.