Identification of the potent phytoestrogen glycinol in elicited soybean (Glycine max).

Endocrinology
Stephen M BouéMatthew E Burow

Abstract

The primary induced isoflavones in soybean, the glyceollins, have been shown to be potent estrogen antagonists in vitro and in vivo. The discovery of the glyceollins' ability to inhibit cancer cell proliferation has led to the analysis of estrogenic activities of other induced isoflavones. In this study, we investigated a novel isoflavone, glycinol, a precursor to glyceollin that is produced in elicited soy. Sensitive and specific in vitro bioassays were used to determine that glycinol exhibits potent estrogenic activity. Estrogen-based reporter assays were performed, and glycinol displayed a marked estrogenic effect on estrogen receptor (ER) signaling between 1 and 10 microM, which correlated with comparable colony formation of MCF-7 cells at 10 microM. Glycinol also induced the expression of estrogen-responsive genes (progesterone receptor and stromal-cell-derived factor-1). Competitive binding assays revealed a high affinity of glycinol for both ER alpha (IC(50) = 13.8 nM) and ER beta (IC(50) = 9.1 nM). In addition, ligand receptor modeling (docking) studies were performed and glycinol was shown to bind similarly to both ER alpha and ER beta. Taken together, these results suggest for the first time that glycinol is estrogeni...Continue Reading

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Citations

Nov 8, 2011·The Proceedings of the Nutrition Society·Hyo Jung KimJong-Sang Kim
Jun 15, 2011·Organic Letters·Michael A Calter, Na Li
Oct 3, 2009·The Journal of Pharmacology and Experimental Therapeutics·M Carla ZimmermannMatthew E Burow
Dec 25, 2012·BMC Complementary and Alternative Medicine·Young Min LeeHaeng Ran Kim
Sep 24, 2010·Endocrinology·James W AntoonBarbara S Beckman
Mar 10, 2012·PloS One·Syreeta L TilghmanMatthew E Burow
Feb 16, 2011·Journal of Molecular Endocrinology·James W AntoonBarbara S Beckman
Jun 15, 2011·Inflammation Research : Official Journal of the European Histamine Research Society ... [et Al.]·Hyo Jung KimJong-Sang Kim
Feb 22, 2011·Applied Microbiology and Biotechnology·Tzi Bun NgHe Xiang Wang
Sep 24, 2015·Molecular Nutrition & Food Research·Naoki NanashimaYoji Kato
May 29, 2012·The Journal of Steroid Biochemistry and Molecular Biology·Bridgette M Collins-BurowMatthew E Burow
Jun 16, 2015·Environment International·Ryoiti Kiyama, Yuko Wada-Kiyama
Mar 25, 2010·Food and Chemical Toxicology : an International Journal Published for the British Industrial Biological Research Association·Rajeev MishraP S R Murthy
Apr 26, 2011·Journal of Medicinal Chemistry·Rahul S KhupsePaul W Erhardt
Jun 5, 2012·Journal of Agricultural and Food Chemistry·Stephen M BouéMark L Heiman
Aug 4, 2012·Experimental Biology and Medicine·James W AntoonBarbara S Beckman
Sep 9, 2018·The Plant Journal : for Cell and Molecular Biology·Arjun SukumaranSangeeta Dhaubhadel
Aug 5, 2017·BMC Complementary and Alternative Medicine·Stéphane ZingueDieudonné Njamen
Dec 5, 2018·Experimental Biology and Medicine·Gismar Mc RodriguesSuzelei de Castro Franca
Dec 1, 2009·Journal of Natural Products·Amarjit LuniwalPaul W Erhardt

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