Glyceollin III

Glyceollin III
Names
	Preferred IUPAC name (2S,6aS,11aS)-2-(Prop-1-en-2-yl)-1,2-dihydro-6H-[1]benzofuro[3,2-c]furo[3,2-g][1]benzopyran-6a,9(11aH)-diol
Identifiers
CAS Number	61080-23-7 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:52086 ;
ChEMBL	ChEMBL2229450 ;
ChemSpider	10128488 ;
KEGG	C15511 ;
PubChem CID	11954193;
UNII	629FG6XLLL ;
CompTox Dashboard (EPA)	DTXSID20976571 ;
	InChI InChI=1S/C20H18O5/c1-10(2)15-6-11-5-13-17(8-16(11)24-15)23-9-20(22)14-4-3-12(21)7-18(14)25-19(13)20/h3-5,7-8,15,19,21-22H,1,6,9H2,2H3/t15-,19-,20+/m0/s1 Key: MIYTVBARXCVVHZ-RYGJVYDSSA-N;
	SMILES CC(=C)[C@@H]1Cc2cc3c(cc2O1)OC[C@@]4([C@H]3Oc5c4ccc(c5)O)O;
Properties
Chemical formula	C20H18O5
Molar mass	338.35 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 ?) Infobox references

Glyceollin III is a glyceollin, a type of pterocarpan, found in the soybean (Glycine max).^[1]^[2] It has an antiestrogenic effect.^[3] In soil, it has an antifungal activity against Aspergillus sojae.^[4]

^ Zimmermann, M. Carla; Tilghman, Syreeta L.; Boué, Stephen M.; Salvo, Virgilio A.; Elliott, Steven; Williams, K. Y.; Skripnikova, Elena V.; Ashe, Hasina; Payton-Stewart, Florastina; Vanhoy-Rhodes, Lyndsay; Fonseca, Juan Pablo; Corbitt, Cynthia; Collins-Burow, Bridgette M.; Howell, Melanie H.; Lacey, Michelle; Shih, Betty Y.; Carter-Wientjes, Carol; Cleveland, Thomas E.; McLachlan, John A.; Wiese, Thomas E.; Beckman, Barbara S.; Burow, Matthew E. (2010). "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.
^ Banks, Stephen W.; Dewick, Paul M. (1983). "Biosynthesis of glyceollins I, II and III in soybean". Phytochemistry. 22 (12): 2729–2733. doi:10.1016/S0031-9422(00)97682-9.
^ Salvo Virgilo A., Boue Stephen M., Fonseca Juan P., Elliott Steven, Corbitt Cynthia, Collins-Burow Bridgette M., Curiel Tyler J., Srivastav Sudesh K., Shih Betty Y., Carter-Wientjes Carol, Wood Charles E., Erhardt Paulw., Beckman Barbara S., McLachlan John A., Cleveland Thomas E. and Burow Matthew E. (2006). "Antiestrogenic glyceollins suppress human breast and ovarian carcinoma tumorigenesis". Clinical Cancer Research. 12 (23): 7159–7164. doi:10.1158/1078-0432.CCR-06-1426. PMID 17145841.{{cite journal}}: CS1 maint: multiple names: authors list (link)
^ Kim, Hyo Jung; Suh, Hwa-Jin; Lee, Choong Hwan; Kim, Jeong Hwan; Kang, Sun Chul; Park, Sunmin; Kim, Jong-Sang (2010). "Antifungal Activity of Glyceollins Isolated from Soybean Elicited with Aspergillus sojae". Journal of Agricultural and Food Chemistry. 58 (17): 9483–9487. doi:10.1021/jf101694t. PMID 20666365.

[1] Zimmermann, M. Carla; Tilghman, Syreeta L.; Boué, Stephen M.; Salvo, Virgilio A.; Elliott, Steven; Williams, K. Y.; Skripnikova, Elena V.; Ashe, Hasina; Payton-Stewart, Florastina; Vanhoy-Rhodes, Lyndsay; Fonseca, Juan Pablo; Corbitt, Cynthia; Collins-Burow, Bridgette M.; Howell, Melanie H.; Lacey, Michelle; Shih, Betty Y.; Carter-Wientjes, Carol; Cleveland, Thomas E.; McLachlan, John A.; Wiese, Thomas E.; Beckman, Barbara S.; Burow, Matthew E. (2010). "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] Banks, Stephen W.; Dewick, Paul M. (1983). "Biosynthesis of glyceollins I, II and III in soybean". Phytochemistry. 22 (12): 2729–2733. doi:10.1016/S0031-9422(00)97682-9.

[3] Salvo Virgilo A., Boue Stephen M., Fonseca Juan P., Elliott Steven, Corbitt Cynthia, Collins-Burow Bridgette M., Curiel Tyler J., Srivastav Sudesh K., Shih Betty Y., Carter-Wientjes Carol, Wood Charles E., Erhardt Paulw., Beckman Barbara S., McLachlan John A., Cleveland Thomas E. and Burow Matthew E. (2006). "Antiestrogenic glyceollins suppress human breast and ovarian carcinoma tumorigenesis". Clinical Cancer Research. 12 (23): 7159–7164. doi:10.1158/1078-0432.CCR-06-1426. PMID 17145841.{{cite journal}}: CS1 maint: multiple names: authors list (link)

[4] Kim, Hyo Jung; Suh, Hwa-Jin; Lee, Choong Hwan; Kim, Jeong Hwan; Kang, Sun Chul; Park, Sunmin; Kim, Jong-Sang (2010). "Antifungal Activity of Glyceollins Isolated from Soybean Elicited with Aspergillus sojae". Journal of Agricultural and Food Chemistry. 58 (17): 9483–9487. doi:10.1021/jf101694t. PMID 20666365.

[1]

[2]

[3]

[4]