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ARS Home » Southeast Area » New Orleans, Louisiana » Southern Regional Research Center » Food and Feed Safety Research » Research » Publications at this Location » Publication #241732
Title: Identification of the Potent Phytoestrogen Glycinol in Elicited Soybean (Glycine max)

Author
item Boue, Stephen
item TILGHMAN, SYREETA - Tulane University Medical Center
item ELLIOTT, STEVEN - Tulane University Medical Center
item ZIMMERMAN, M. CARLA - Tulane University Medical Center
item WILLIAMS, K. - Tulane University Medical Center
item PAYTON-STEWART, FLORASTINA - Tulane University Medical Center
item MIRAFLOR, ALLEN - Tulane University Medical Center
item HOWELL, MELANIE - Tulane University Medical Center
item Shih, Betty
item Carter-Wientjes, Carol
item SEGAR, CHRIS - Xavier University
item BECKMAN, BARBARA - Tulane University Medical Center
item WIESE, THOMAS - Xavier University
item Cleveland, Thomas
item MCLACHLAN, JOHN - Tulane University Medical Center
item BUROW, MATTHEW - Tulane University Medical Center

Submitted to: Endocrinology
Publication Type: Peer Reviewed Journal
Publication Acceptance Date: 12/19/2008
Publication Date: 12/30/2008
Citation: Boue, S.M., Tilghman, S.L., Elliott, S., Zimmerman, M., Williams, K.Y., Payton-Stewart, F., Miraflor, A.P., Howell, M.H., Shih, B.Y., Carter Wientjes, C.H., Segar, C., Beckman, B.S., Wiese, T.E., Cleveland, T.E., Mclachlan, J.A., Burow, M.E. 2009. Identification of the Potent Phytoestrogen Glycinol in Elicited Soybean (Glycine max). Endocrinology. 150(5):2446-2453.

Interpretive Summary: 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. Glycinol also induced the expression of estrogen responsive genes. Binding assays revealed a high affinity of glycinol for both estrogen receptors. In addition,computer modeling studies were performed and glycinol was shown to bind similarly to both estrogen receptors. Taken together, these results suggest for the first time that glycinol is estrogenic and may represent an important component of the health effects of soybased foods.

Technical 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 ER signaling between 1-10 µM, which correlated with comparable colony formation of MCF-7 cells at 10 µM. Glycinol also induced the expression of estrogen responsive genes (PgR and SDF-1). Competitive binding assays revealed a high affinity of glycinol for both ERa ('C50=13.8 nM) and ERß ('C50=9.1 nM). In addition,ligand receptor modeling (docking) studies were performed and glycinol was shown to bind similarly to both ERa and ERß. Taken together, these results suggest for the first time that glycinol is estrogenic and may represent an important component of the health effects of soybased foods.