Glyceollin I
Chemical compound
From Wikipedia, the free encyclopedia
Glyceollin I is a glyceollin, a type of prenylated pterocarpan. It is a phytoalexin found in the soybean.[1]
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| Names | |
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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 | |
| Identifiers | |
3D model (JSmol) |
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| ChEBI | |
| ChemSpider | |
| ECHA InfoCard | 100.222.666 |
| KEGG | |
PubChem CID |
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| UNII | |
CompTox Dashboard (EPA) |
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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).
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In in vitro studies, this molecule has been shown to exhibit antiestrogenic properties.[2]
Biosynthesis
All the glyceollins are products of a pathway in soybean which starts from the amino acid L-phenylalanine. This is converted in a series of steps to the flavanone, liquiritigenin, and then by the action of isoflavonoid synthase (IFS) to the isoflavone, daidzein.[3][4]: Supplement 1
A further sequence of four enzyme-catalysed reactions creates the pterocarpan ring system of the compound glycinol. The prenylation enzyme trihydroxypterocarpan dimethylallyltransferase (G4DT) and then glyceollin synthase (GS) complete the biosynthesis of glyceollin I.[4]
Chemical synthesis
Glyceollin I has been synthesized in the laboratory at a multigram scale.[5]