Chemistry:Glyceollin I
From HandWiki
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| Preferred IUPAC name
(6aS,11aS)-2,2-Dimethyl-2H,6H-[1]benzofuro[3,2-c]pyrano[2,3-h][1]benzopyran-6a,9(11aH)-diol | |
| Other names
(−)-Glyceollin I
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3D model (JSmol)
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| Properties | |
| C20H18O5 | |
| Molar mass | 338 g/mol |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
 verify (what is   ?)
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| Infobox references | |
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]
References
- ↑ Zimmermann, M. C.; Tilghman, S. L.; Boué, S. M.; Salvo, V. A.; Elliott, S.; Williams, K. Y.; Skripnikova, E. V.; Ashe, H. et al. (2009). "Glyceollin I, a Novel Antiestrogenic Phytoalexin Isolated from Activated Soy". Journal of Pharmacology and Experimental Therapeutics 332 (1): 35–45. doi:10.1124/jpet.109.160382. PMID 19797619.
- ↑ Welle, R.; Grisebach, H. (1988). "Induction of phytoalexin synthesis in soybean: Enzymatic cyclization of prenylated pterocarpans to glyceollin isomers". Archives of Biochemistry and Biophysics 263 (1): 191–198. doi:10.1016/0003-9861(88)90627-3. PMID 3369863.
- ↑ Payton-Stewart, F.; Khupse, R. S.; Boué, S. M.; Elliott, S.; Zimmermann, M. C.; Skripnikova, E. V.; Ashe, H.; Tilghman, S. L. et al. (2010). "Glyceollin I enantiomers distinctly regulate ER-mediated gene expression". Steroids 75 (12): 870–878. doi:10.1016/j.steroids.2010.05.007. PMID 20493896. https://naldc-legacy.nal.usda.gov/naldc/download.xhtml?id=44156&content=PDF.
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