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| 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]<wbr>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_Ref = {{cascite|correct|??}}
| CASNo = 57103-57-8
| CASNo = 57103-57-8
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 6461TV6UCH
| PubChem = 162807
| PubChem = 162807
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
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'''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 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 | 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| pmc = }}</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| pmc = | url = https://naldc.nal.usda.gov/naldc/download.xhtml?id=44156&content=PDF }}</ref>
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>


== References ==
== References ==
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[[Category:Pterocarpans]]
[[Category:Pterocarpans]]
[[Category:Phytoalexins]]
[[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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