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{{Chembox
{{Chembox
| Verifiedfields = changed
| Watchedfields = changed
| Watchedfields = changed
| verifiedrevid = 417636943
| verifiedrevid = 423639166
| ImageFile = Glyceollin I.svg
| ImageFile = Glyceollin I.svg
| ImageSize =
| ImageSize =
| ImageAlt =
| ImageAlt =
| IUPACName = (6a''S'',11a''S'')-2,2-dimethyl-2''H'',6''H''-[1]benzofuro[3,2&#8209;c]pyrano[2,3&#8209;h]<br>chromene-6a,9(11a''H'')-diol
| PIN = (6a''S'',11a''S'')-2,2-Dimethyl-2''H'',6''H''-[1]benzofuro[3,2-''c'']pyrano[2,3-''h''][1]benzopyran-6a,9(11a''H'')-diol
| OtherNames = (−)-Glyceollin I
| OtherNames = (−)-Glyceollin I
| Section1 = {{Chembox Identifiers
|Section1={{Chembox Identifiers
| CASNo_Ref = {{cascite|correct|??}}
| CASNo = 57103-57-8
| PubChem = 162807
| CASNo = 57103-57-8
| UNII_Ref = {{fdacite|correct|FDA}}
⚫
| SMILES = }}
| UNII = 6461TV6UCH
⚫
| Section2 = {{Chembox Properties
| PubChem = 162807
⚫
| Formula = C<sub>20</sub>H<sub>18</sub>O<sub>5</sub>
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
⚫
| MolarMass =
| ChemSpiderID = 142931
| ExactMass = 338.11542 u
| SMILES = CC1(C=Cc2c(ccc3c2OC[C@@]4([C@H]3Oc5c4ccc(c5)O)O)O1)C
⚫
| Appearance =
| 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
⚫
| Density =
| InChIKey = YIFYYPKWOQSCRI-AZUAARDMBS
⚫
| MeltingPt =
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
⚫
| BoilingPt =
| StdInChI = 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
| Solubility = }}
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
⚫
| Section3 = {{Chembox Hazards
| StdInChIKey = YIFYYPKWOQSCRI-AZUAARDMSA-N
⚫
| MainHazards =
| FlashPt =
| RTECS =
| Autoignition = }}
| MeSHName =
| ChEBI_Ref = {{ebicite|changed|EBI}}
| ChEBI = 16470
| KEGG_Ref = {{keggcite|changed|kegg}}
| KEGG = C01701 }}
⚫
|Section2={{Chembox Properties
⚫
| Formula = C<sub>20</sub>H<sub>18</sub>O<sub>5</sub>
⚫
| MolarMass = 338 g/mol
⚫
| Appearance =
⚫
| Density =
⚫
| MeltingPt =
⚫
| BoilingPt =
⚫
| Solubility = }}
⚫
|Section3={{Chembox Hazards
⚫
| MainHazards =
| FlashPt =
| AutoignitionPt = }}
}}
}}
'''Glyceollin I''' is a [[glyceollin]], a type of [[prenylated]] [[pterocarpan]]. It is a [[phytoalexin]] found in the [[soybean]].<ref>Glyceollin I, a Novel Antiestrogenic Phytoalexin Isolated from Activated Soy. M. Carla Zimmermann, Syreeta L. Tilghman, Stephen M. Boué, Virgilio A. Salvo, Steven Elliott, K. Y. Williams, Elena V. Skripnikova, Hasina Ashe, Florastina Payton-Stewart, Lyndsay Vanhoy-Rhodes, Juan Pablo Fonseca, Cynthia Corbitt, Bridgette M. Collins-Burow, Melanie H. Howell, Michelle Lacey, Betty Y. Shih, Carol Carter-Wientjes, Thomas E. Cleveland, John A. McLachlan, Thomas E. Wiese, Barbara S. Beckman and Matthew E. Burow, JPET January 2010 vol. 332 no. 1, {{doi|10.1124/jpet.109.160382}}</ref>
'''Glyceollin I''' is a [[glyceollin]], a type of [[prenylated]] [[pterocarpan]]. It is a [[phytoalexin]] found in the [[soybean]].<ref>{{Cite journal | last1 = Zimmermann | first1 = M. C. | last2 = Tilghman | first2 = S. L. | last3 = Boué | first3 = S. M. | last4 = Salvo | first4 = V. A. | last5 = Elliott | first5 = S. | last6 = Williams | first6 = K. Y. | last7 = Skripnikova | first7 = E. V. | last8 = Ashe | first8 = H. | last9 = Payton-Stewart | first9 = F. | doi = 10.1124/jpet.109.160382 | last10 = Vanhoy-Rhodes | first10 = L. | last11 = Fonseca | first11 = J. P. | last12 = Corbitt | first12 = C. | last13 = Collins-Burow | first13 = B. M. | last14 = Howell | first14 = M. H. | last15 = Lacey | first15 = M. | last16 = Shih | first16 = B. Y. | last17 = Carter-Wientjes | first17 = C. | last18 = Cleveland | first18 = T. E. | last19 = McLachlan | first19 = J. A. | last20 = Wiese | first20 = T. E. | last21 = Beckman | first21 = B. S. | last22 = Burow | first22 = M. E. | title = Glyceollin I, a Novel Antiestrogenic Phytoalexin Isolated from Activated Soy | journal = Journal of Pharmacology and Experimental Therapeutics | volume = 332 | issue = 1 | pages = 35–45 | year = 2009 | pmid = 19797619| pmc =2802480 }}</ref>


[[Glyceollin synthase]] is an enzyme responsible for the production of glyceollin.<ref>{{cite journal | author = Welle R, Grisebach H | date = 1988 | title = Induction of phytoalexin synthesis in soybean: enzymatic cyclization of prenylated pterocarpans to glyceollin isomers | journal = Arch. Biochem. Biophys. | volume = 263 | pages = 191&ndash;8 | pmid = 3369863 | doi = 10.1016/0003-9861(88)90627-3 | issue = 1 }}</ref> The five substrates of this enzyme are [[2-dimethylallyl-(6aS,11aS)-3,6a,9-trihydroxypterocarpan]], [[4-dimethylallyl-(6aS,11aS)-3,6a,9-trihydroxypterocarpan]], [[nicotinamide adenine dinucleotide phosphate|NADPH]], [[hydrogen ion|H<sup>+</sup>]], and [[oxygen|O<sub>2</sub>]], whereas its three products are glyceollin, [[nicotinamide adenine dinucleotide phosphate|NADP<sup>+</sup>]], and [[water|H<sub>2</sub>O]].
[[Glyceollin synthase]] is an enzyme responsible for the production of glyceollin.<ref>{{Cite journal | last1 = Welle | first1 = R. | last2 = Grisebach | first2 = H. | doi = 10.1016/0003-9861(88)90627-3 | title = Induction of phytoalexin synthesis in soybean: Enzymatic cyclization of prenylated pterocarpans to glyceollin isomers | journal = Archives of Biochemistry and Biophysics | volume = 263 | issue = 1 | pages = 191–198 | year = 1988 | pmid = 3369863}}</ref> The five substrates of this enzyme are 2-dimethylallyl-(6aS,11aS)-3,6a,9-trihydroxypterocarpan, 4-dimethylallyl-(6aS,11aS)-3,6a,9-trihydroxypterocarpan, [[nicotinamide adenine dinucleotide phosphate|NADPH]], [[hydrogen ion|H<sup>+</sup>]], and [[oxygen|O<sub>2</sub>]], whereas its three products are glyceollin, [[nicotinamide adenine dinucleotide phosphate|NADP<sup>+</sup>]], and [[water|H<sub>2</sub>O]].


In in vitro studies, this molecule has been shown to exhibit [[antiestrogenic]] properties.<ref>{{Cite journal | last1 = Payton-Stewart | first1 = F. | last2 = Khupse | first2 = R. S. | last3 = Boué | first3 = S. M. | last4 = Elliott | first4 = S. | last5 = Zimmermann | first5 = M. C. | last6 = Skripnikova | first6 = E. V. | last7 = Ashe | first7 = H. | last8 = Tilghman | first8 = S. L. | last9 = Beckman | first9 = B. S. | doi = 10.1016/j.steroids.2010.05.007 | last10 = Cleveland | first10 = T. E. | last11 = McLachlan | first11 = J. A. | last12 = Bhatnagar | first12 = D. | last13 = Wiese | first13 = T. E. | last14 = Erhardt | first14 = P. | last15 = Burow | first15 = M. E. | title = Glyceollin I enantiomers distinctly regulate ER-mediated gene expression | journal = Steroids | volume = 75 | issue = 12 | pages = 870–878 | year = 2010 | pmid = 20493896 | s2cid = 14878980 | url = https://naldc-legacy.nal.usda.gov/naldc/download.xhtml?id=44156&content=PDF | hdl = 11336/58472 | hdl-access = free }}{{Dead link|date=June 2024 |bot=InternetArchiveBot |fix-attempted=yes }}</ref>
This molecule exhibits [[antiestrogenic]] properties.<ref>Glyceollin I enantiomers distinctly regulate ER-mediated gene expression. Florastina Payton-Stewart, Rahul S. Khupse, Stephen M. Boué, Steven Elliott, M. Carla Zimmermann, Elena V. Skripnikova, Hasina Ashe, Syreeta L. Tilghman, Barbara S. Beckman, Thomas E. Cleveland, John A. McLachlan, Deepak Bhatnagar, Thomas E. Wiese, Paul Erhardt and Matthew E. Burow, Steroids, Volume 75, Issue 12, December 2010, Pages 870-878, {{doi|10.1016/j.steroids.2010.05.007}}, {{PMID|20493896}}</ref>


==References==
== References ==
{{reflist}}
{{Reflist}}


<!-- ==External links== -->
<!-- ==External links== -->


{{Pterocarpan}}
{{Pterocarpan}}
{{Estrogen receptor modulators}}

[[Category:Antiestrogens]]


[[Category:Pterocarpans]]
[[Category:Pterocarpans]]
[[Category:Phytoalexins]]
[[Category:Heterocyclic compounds with 5 rings]]


{{natural-phenol-stub}}
{{aromatic-stub}}

Latest revision as of 19:15, 8 June 2024

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 ☒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
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 ?)

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

[edit]
  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.[permanent dead link‍]


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