Jump to content

Glyceollin I

From Wikipedia, the free encyclopedia
Glyceollin I
Names
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)
ChEBI
ChemSpider
ECHA InfoCard 100.222.666 Edit this at Wikidata
KEGG
UNII
  • InChI=1S/C20H18O5/c1-19(2)8-7-12-15(25-19)6-4-13-17(12)23-10-20(22)14-5-3-11(21)9-16(14)24-18(13)20/h3-9,18,21-22H,10H2,1-2H3/t18-,20+/m0/s1 X markN
    Key: YIFYYPKWOQSCRI-AZUAARDMSA-N checkY
  • CC1(C=Cc2c(ccc3c2OC[C@@]4([C@H]3Oc5c4ccc(c5)O)O)O1)C
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).

Glyceollin I is a glyceollin, a type of prenylated pterocarpan. It is a phytoalexin found in the soybean.[1]

In in vitro studies, this molecule has been shown to exhibit antiestrogenic properties.[2]

Biosynthesis

[edit]

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 

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 I.[4]

2D representation of the chemical structure of glycinol (pterocarpan).
glycinol
G4DT
 
 
Rightward reaction arrow
 
 
 
2D representation of the chemical structure of Q27121834.
4-glyceollidin
GS
 
 
Rightward reaction arrow
 
 
 
2D representation of the chemical structure of glyceollin I .
glyceollin I

Chemical synthesis

[edit]

Glyceollin I has been synthesized in the laboratory at a multigram scale.[5]

References

[edit]
  1. ↑ Zimmermann, M. C.; Tilghman, S. L.; Boué, S. M.; et al. (2009). "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. ↑ Payton-Stewart, F.; Khupse, R. S.; Boué, S. M.; Elliott, S.; Zimmermann, M. C.; Skripnikova, E. V.; Ashe, H.; Tilghman, S. L.; Beckman, B. S.; Cleveland, T. E.; McLachlan, J. A.; Bhatnagar, D.; Wiese, T. E.; Erhardt, P.; Burow, M. E. (2010). "Glyceollin I enantiomers distinctly regulate ER-mediated gene expression". Steroids. 75 (12): 870–878. doi:10.1016/j.steroids.2010.05.007. hdl:11336/58472. PMID 20493896. S2CID 14878980.[dead link]
  3. ↑ Lygin, Anatoliy V.; Zernova, Olga V.; Hill, Curtis B.; Kholina, Nadegda A.; Widholm, Jack M.; Hartman, Glen L.; Lozovaya, Vera V. (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.
  4. 1 2 Khatri, Praveen; Kuflu, Kuflom; McDowell, Tim; Lin, Jie; Kovinich, Nikola; Dhaubhadel, Sangeeta (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.
  5. ↑ Luniwal, Amarjit; Khupse, Rahul; Reese, Michael; et al. (2011-09-16). "Multigram Synthesis of Glyceollin I". Organic Process Research & Development. 15 (5): 1149–1162. doi:10.1021/op200112g. ISSN 1083-6160.
Retrieved from "https://en.wikipedia.org/w/index.php?title=Glyceollin_I&oldid=1346903002"