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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
ChEBI
ChEMBL
ChemSpider
KEGG
UNII
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
CC(=C)[C@@H]1Cc2cc3c(cc2O1)OC[C@@]4([C@H]3Oc5c4ccc(c5)O)O
Properties
C20 H18 O5
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).
Chemical compound
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 .
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Lavender oil
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Agonists Antagonists Unknown