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

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.[4][5]: Supplement 1 

2D representation of the chemical structure of phenylalanine .
phenylalanine
Steps
 
 
Rightward reaction arrow
 
 
 
2D representation of the chemical structure of liquiritigenin.
liquiritigenin
IFS
 
 
Rightward reaction arrow
 
 
 
2D representation of the chemical structure of daidzein.
daidzein

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.[5]

2D representation of the chemical structure of glycinol (pterocarpan).
glycinol
G4DT
 
 
Rightward reaction arrow
 
 
 
2D representation of the chemical structure of Q27121915.
glyceocarpin
GS
 
 
Rightward reaction arrow
 
 
 
2D representation of the chemical structure of Q5572524.
glyceollin III


References

  1. ↑ 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.
  2. ↑ Salvo, Virgilo A.; Boué, Stephen M.; Fonseca, Juan P.; et al. (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.
  3. ↑ Kim, Hyo Jung; Suh, Hwa-Jin; Lee, Choong Hwan; et al. (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.
  4. ↑ Lygin, Anatoliy V.; Zernova, Olga V.; Hill, Curtis B.; et al. (2013). "Glyceollin is an Important Component of Soybean Plant Defense Against Phytophthora sojae and Macrophomina phaseolina". Phytopathology. 103 (10). American Phytopathological Society: 984–994. doi:10.1094/phyto-12-12-0328-r. ISSN 0031-949X. PMID 23617338. S2CID 12170923.
  5. 1 2 Khatri, Praveen; Kuflu, Kuflom; McDowell, Tim; et al. (2025). "Discovery of three cytochrome P450 monooxygenase prenyl cyclases that catalyze the final step of glyceollin biosynthesis in soybean". Molecular Plant. 18 (5): 721–724. doi:10.1016/j.molp.2025.01.022. PMID 39891385.
source: https://en.wikipedia.org/wiki/Glyceollin_III