The promiscuous estrogen receptor: Evolution of physiological estrogens and response to phytochemicals and endocrine disruptors

The Journal of Steroid Biochemistry and Molecular Biology
Michael E Baker, Richard Lathe

Abstract

Many actions of estradiol (E2), the principal physiological estrogen in vertebrates, are mediated by estrogen receptor-α (ERα) and ERβ. An important physiological feature of vertebrate ERs is their promiscuous response to several physiological steroids, including estradiol (E2), Δ5-androstenediol, 5α-androstanediol, and 27-hydroxycholesterol. A novel structural characteristic of Δ5-androstenediol, 5α-androstanediol, and 27-hydroxycholesterol is the presence of a C19 methyl group, which precludes the presence of an aromatic A ring with a C3 phenolic group that is a defining property of E2. The structural diversity of these estrogens can explain the response of the ER to synthetic chemicals such as bisphenol A and DDT, which disrupt estrogen physiology in vertebrates, and the estrogenic activity of a variety of plant-derived chemicals such as genistein, coumestrol, and resveratrol. Diversity in the A ring of physiological estrogens also expands potential structures of industrial chemicals that can act as endocrine disruptors. Compared to E2, synthesis of 27-hydroxycholesterol and Δ5-androstenediol is simpler, leading us, based on parsimony, to propose that one or both of these steroids or a related metabolite was a physiological ...Continue Reading

Citations

May 28, 2019·Toxicological Sciences : an Official Journal of the Society of Toxicology·Kim M TruongIsaac N Pessah
Apr 21, 2020·Endocrine Reviews·Elisabet Stener-VictorinDavid H Abbott
Aug 23, 2019·Molecular Medicine Reports·Guangrun LiZuofu Zhang
Mar 11, 2020·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Ting WangM Natália D S Cordeiro
Dec 14, 2018·Clinical Science·Luis MolinaPamela Ehrenfeld
Mar 6, 2019·International Journal of Molecular Sciences·Francesca De AmicisVincenzo Pezzi
Oct 9, 2020·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Rolando PasquarielloMargherita Maranesi
Mar 7, 2021·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Ana BornadiegoCarlos F Marcos
Nov 25, 2019·Molecular and Cellular Endocrinology·Lucia Toporova, Patrick Balaguer
Jan 22, 2020·Molecular and Cellular Endocrinology·Virginie Cuvillier-Hot, Alain Lenoir
May 15, 2020·Molecular and Cellular Endocrinology·Laura N VandenbergJoshua P Mogus
Jun 14, 2021·Comparative Biochemistry and Physiology. Toxicology & Pharmacology : CBP·Yuyang Wang, Hong-Sheng Wang
Jul 3, 2021·Pharmaceuticals·Xia CaiShi-Wen Jiang

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