Glyceollin I Explained

Glyceollin I is a glyceollin, a type of prenylated pterocarpan. It is a phytoalexin found in the soybean.^[1]

Glyceollin synthase is an enzyme responsible for the production of glyceollin.^[2] The five substrates of this enzyme are 2-dimethylallyl-(6aS,11aS)-3,6a,9-trihydroxypterocarpan, 4-dimethylallyl-(6aS,11aS)-3,6a,9-trihydroxypterocarpan, NADPH, H⁺, and O₂, whereas its three products are glyceollin, NADP⁺, and H₂O.

In in vitro studies, this molecule has been shown to exhibit antiestrogenic properties.^[3]

Notes and References

1. Zimmermann . M. C. . Tilghman . S. L. . Boué . S. M. . Salvo . V. A. . Elliott . S. . Williams . K. Y. . Skripnikova . E. V. . Ashe . H. . Payton-Stewart . F. . 10.1124/jpet.109.160382 . Vanhoy-Rhodes . L. . Fonseca . J. P. . Corbitt . C. . Collins-Burow . B. M. . Howell . M. H. . Lacey . M. . Shih . B. Y. . Carter-Wientjes . C. . Cleveland . T. E. . McLachlan . J. A. . Wiese . T. E. . Beckman . B. S. . Burow . M. E. . Glyceollin I, a Novel Antiestrogenic Phytoalexin Isolated from Activated Soy . Journal of Pharmacology and Experimental Therapeutics . 332 . 1 . 35–45 . 2009 . 19797619. 2802480 .
2. Welle . R. . Grisebach . H. . 10.1016/0003-9861(88)90627-3 . Induction of phytoalexin synthesis in soybean: Enzymatic cyclization of prenylated pterocarpans to glyceollin isomers . Archives of Biochemistry and Biophysics . 263 . 1 . 191–198 . 1988 . 3369863.
3. Payton-Stewart . F. . Khupse . R. S. . Boué . S. M. . Elliott . S. . Zimmermann . M. C. . Skripnikova . E. V. . Ashe . H. . Tilghman . S. L. . Beckman . B. S. . 10.1016/j.steroids.2010.05.007 . Cleveland . T. E. . McLachlan . J. A. . Bhatnagar . D. . Wiese . T. E. . Erhardt . P. . Burow . M. E. . Glyceollin I enantiomers distinctly regulate ER-mediated gene expression . Steroids . 75 . 12 . 870–878 . 2010 . 20493896 . 14878980 . 11336/58472 . free .