Chemistry:Glyceollin III

Short description: Type of pterocarpan found in the soybean

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 Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:52086 Y
ChEMBL	ChEMBL2229450 Y
ChemSpider	10128488 Y
KEGG	C15511 Y
PubChem CID	11954193
UNII	629FG6XLLL Y
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).
Infobox references

Tracking categories (test):

• SizeSet

Glyceollin III is a glyceollin, a type of pterocarpan, found in the soybean (Glycine max). It has an antiestrogenic effect in vivo. In soil, it has an antifungal activity against Aspergillus sojae.

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.

1. REDIRECT Template:Chemical reaction

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 III.

1. REDIRECT Template:Chemical reaction