Glyceollin I

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
CAS Number
  • 57103-57-8 checkY
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:16470 ☒N
ChemSpider
  • 142931 ☒N
ECHA InfoCard 100.222.666 Edit this at Wikidata
KEGG
  • C01701 ☒N
PubChem CID
  • 162807
UNII
  • 6461TV6UCH checkY
CompTox Dashboard (EPA)
  • DTXSID10205726 Edit this at Wikidata
InChI
  • 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 ☒N
    Key: YIFYYPKWOQSCRI-AZUAARDMSA-N ☒N
  • InChI=1/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
    Key: YIFYYPKWOQSCRI-AZUAARDMBS
  • CC1(C=Cc2c(ccc3c2OC[C@@]4([C@H]3Oc5c4ccc(c5)O)O)O1)C
Properties
Chemical formula
 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).
☒N verify (what is checkY☒N ?)
Infobox references
Chemical compound

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

Glyceollin synthase is an enzyme responsible for the production of glyceollin.[2] The five substrates of this enzyme are 2-dimethylallyl-(6aS,11aS)-3,6a,9-trihydroxypterocarpan, 4-dimethylallyl-(6aS,11aS)-3,6a,9-trihydroxypterocarpan, NADPH, H+, and O2, whereas its three products are glyceollin, NADP+, and H2O.

In in vitro studies, this molecule has been shown to exhibit antiestrogenic properties.[3]

References

  1. ^ Zimmermann, M. C.; Tilghman, S. L.; Boué, S. M.; Salvo, V. A.; Elliott, S.; Williams, K. Y.; Skripnikova, E. V.; Ashe, H.; Payton-Stewart, F.; Vanhoy-Rhodes, L.; Fonseca, J. P.; Corbitt, C.; Collins-Burow, B. M.; Howell, M. H.; Lacey, M.; Shih, B. Y.; Carter-Wientjes, C.; Cleveland, T. E.; McLachlan, J. A.; Wiese, T. E.; Beckman, B. S.; Burow, M. E. (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. ^ Welle, R.; Grisebach, H. (1988). "Induction of phytoalexin synthesis in soybean: Enzymatic cyclization of prenylated pterocarpans to glyceollin isomers". Archives of Biochemistry and Biophysics. 263 (1): 191–198. doi:10.1016/0003-9861(88)90627-3. PMID 3369863.
  3. ^ 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.


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Types of pterocarpans
Pterocarpans:
  • Erybraedin C
  • Erythrabyssin II
  • Folitenol
  • Glycinol
  • Maackiain
  • Orientanol A, B and C
  • Pisatin
  • Sophorol
  • Trifolirhizin
O-methylatedPrenylated
  • Bitucarpin A and B
  • Glyceollidin I and II
  • Glyceollins (Glyceollin I, II, III and IV)
  • Glycyrrhizol A
  • Morisianine
  • Phaseolin
  • Striatine
  • v
  • t
  • e
ERTooltip Estrogen receptor
Agonists
Mixed
(SERMsTooltip Selective estrogen receptor modulators)
Antagonists
  • Coregulator-binding modulators: ERX-11
GPERTooltip G protein-coupled estrogen receptor
Agonists
Antagonists
Unknown
See also
Receptor/signaling modulators
Estrogens and antiestrogens
Androgen receptor modulators
Progesterone receptor modulators
List of estrogens
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