Glyceollin I

Glyceollin I

Names
IUPAC names (6aS,11aS)-2,2-dimethyl-2H,6H-[1]benzofuro[3,2‑c]pyrano[2,3‑h] chromene-6a,9(11aH)-diol
Other names (−)-Glyceollin I
Identifiers
CAS Number	57103-57-8
3D model (Jmol)	Interactive image
ChEBI	CHEBI:16470
ChemSpider	142931
ECHA InfoCard	100.222.666
KEGG	C01701
PubChem	162807
InChI InChI=1S/C20H18O5/c1-19(2)8-7-12-15(25-19)6-4-13-17(12)23-10-20(22)14-5-3-11(21)9-16(14)24-18(13)20/h3-9,18,21-22H,10H2,1-2H3/t18-,20+/m0/s1 Key: YIFYYPKWOQSCRI-AZUAARDMSA-N InChI=1/C20H18O5/c1-19(2)8-7-12-15(25-19)6-4-13-17(12)23-10-20(22)14-5-3-11(21)9-16(14)24-18(13)20/h3-9,18,21-22H,10H2,1-2H3/t18-,20+/m0/s1 Key: YIFYYPKWOQSCRI-AZUAARDMBS
SMILES CC1(C=Cc2c(ccc3c2OC[C@@]4([C@H]3Oc5c4ccc(c5)O)O)O1)C
Properties
Chemical formula	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).
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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

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.; 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. (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. PMC 2802480. PMID 19797619.
2. 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.
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.; Cleveland, T. E.; McLachlan, J. A.; Bhatnagar, D.; Wiese, T. E.; Erhardt, P.; Burow, M. E. (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.