Genisteinのソースを表示

{{Distinguish|Genistin}}
{{multiple issues|
{{Primary sources|date=February 2020}}
{{More medical citations needed|date=June 2012}}
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{{Chembox
| Watchedfields = changed
| verifiedrevid = 443833756
| ImageFile = Genistein.svg
| ImageClass = skin-invert-image
| ImageSize = 220px
| ImageFile1 = Genistein-3D-balls.png
| ImageSize1 = 220
| ImageAlt1 = Genistein molecule
| IUPACName = 4′,5,7-Trihydroxyisoflavone
| SystematicName = 5,7-Dihydroxy-3-(4-hydroxyphenyl)-4''H''-1-benzopyran-4-one
| OtherNames = 
| Section1 = {{Chembox Identifiers
| IUPHAR_ligand = 2826
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 4444448
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = DH2M523P0H
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D11680
| KEGG2 = C06563
| InChI = 1/C15H10O5/c16-9-3-1-8(2-4-9)11-7-20-13-6-10(17)5-12(18)14(13)15(11)19/h1-7,16-18H
| InChIKey = TZBJGXHYKVUXJN-UHFFFAOYAH
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 44
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C15H10O5/c16-9-3-1-8(2-4-9)11-7-20-13-6-10(17)5-12(18)14(13)15(11)19/h1-7,16-18H
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = TZBJGXHYKVUXJN-UHFFFAOYSA-N
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 446-72-0
| PubChem = 5280961
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB01645
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 28088
| EINECS =  207-174-9
| Beilstein = 263823
| SMILES = Oc1ccc(cc1)C\3=C\Oc2cc(O)cc(O)c2C/3=O
}}
| Section2 = {{Chembox Properties
| C=15 | H=10 | O=5
| Appearance =
| Density =
| MeltingPt =
| BoilingPt =
| Solubility =
}}
| Section3 = {{Chembox Hazards
| MainHazards =
| FlashPt =
| AutoignitionPt =
}}
}}

'''Genistein''' (C<sub>15</sub>H<sub>10</sub>O<sub>5</sub>) is a naturally occurring compound that structurally belongs to a class of compounds known as [[isoflavones]]. It is described as an [[angiogenesis inhibitor]] and a [[phytoestrogen]].<ref>{{Citation |last1=Sail |first1=Vibhavari |title=Chapter Eighteen - Notch Pathway Modulators as Anticancer Chemotherapeutics |date=2012-01-01 |url=http://www.sciencedirect.com/science/article/pii/B9780123964922000187 |volume=47 |pages=267–280 |editor-last=Desai |editor-first=Manoj C. |series=Annual Reports in Medicinal Chemistry |publisher=Academic Press |language=en |access-date=2020-09-14 |last2=Hadden |first2=M. Kyle |chapter=Notch Pathway Modulators as Anticancer Chemotherapeutics |doi=10.1016/B978-0-12-396492-2.00018-7|isbn=978-0-12-396492-2 }}</ref>

It was first isolated in 1899 from the [[Genista tinctoria|dyer's broom, ''Genista tinctoria'']]; hence, the chemical name. The compound structure was established in 1926, when it was found to be identical with that of '''prunetol'''. It was chemically synthesized in 1928.<ref>{{cite journal |last1=Walter |first1=E. D. |title=Genistin (an Isoflavone Glucoside) and its Aglucone, Genistein, from Soybeans |journal=Journal of the American Chemical Society |volume=63 |issue=12 |pages=3273–76 |year=1941 |doi=10.1021/ja01857a013|bibcode=1941JAChS..63.3273W }}</ref> It has been shown to be the primary secondary metabolite of the ''[[Trifolium]]'' species and ''[[Glycine max]]''.<ref>{{Cite journal |last1=Popiołkiewicz |first1=Joanna |last2=Polkowski |first2=Krzysztof |last3=Skierski |first3=Janusz S. |last4=Mazurek |first4=Aleksander P. |date=November 2005 |title=In vitro toxicity evaluation in the development of new anticancer drugs—genistein glycosides |url=http://dx.doi.org/10.1016/j.canlet.2005.01.014 |journal=Cancer Letters |volume=229 |issue=1 |pages=67–75 |doi=10.1016/j.canlet.2005.01.014 |pmid=16157220 |issn=0304-3835}}</ref>