:Glyceollin I

{{Chembox

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| Watchedfields = changed

| verifiedrevid = 423639166

| ImageFile = Glyceollin I.svg

| ImageSize =

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| PIN = (6aS,11aS)-2,2-Dimethyl-2H,6H-[1]benzofuro[3,2-c]pyrano[2,3-h][1]benzopyran-6a,9(11aH)-diol

| OtherNames = (−)-Glyceollin I

|Section1={{Chembox Identifiers

| CASNo_Ref = {{cascite|correct|??}}

| CASNo = 57103-57-8

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 6461TV6UCH

| PubChem = 162807

| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}

| ChemSpiderID = 142931

| SMILES = CC1(C=Cc2c(ccc3c2OC[C@@]4([C@H]3Oc5c4ccc(c5)O)O)O1)C

| 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

| InChIKey = YIFYYPKWOQSCRI-AZUAARDMBS

| StdInChI_Ref = {{stdinchicite|changed|chemspider}}

| 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

| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}

| StdInChIKey = YIFYYPKWOQSCRI-AZUAARDMSA-N

| RTECS =

| MeSHName =

| ChEBI_Ref = {{ebicite|changed|EBI}}

| ChEBI = 16470

| KEGG_Ref = {{keggcite|changed|kegg}}

| KEGG = C01701 }}

|Section2={{Chembox Properties

| Formula = C₂₀H₁₈O₅

| MolarMass = 338 g/mol

| Appearance =

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|Section3={{Chembox Hazards

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Glyceollin I is a glyceollin, a type of prenylated pterocarpan. It is a phytoalexin found in the soybean.{{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 }}

Glyceollin synthase is an enzyme responsible for the production of glyceollin.{{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}} 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.{{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 }}