View source for Genistein

{{Distinguish|Genistin}}
{{More medical citations needed|date=June 2012}}
{{Use American English|date=April 2025}}
{{Use dmy dates|date=April 2025}}
{{cs1 config|name-list-style=vanc|display-authors=3}}
{{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 plant-derived, [[aglycone]] [[isoflavone]].<ref name="lpi">{{Cite web|title=Soy isoflavones|date=2025 |url=https://lpi.oregonstate.edu/mic/dietary-factors/phytochemicals/soy-isoflavones |publisher=Micronutrient Information Center, Linus Pauling Institute, Oregon State University |access-date=9 April 2025}}</ref> Genistein has the highest content of all isoflavones in [[soybean|soybeans and soy products]], such as [[tempeh]]. As a type of [[phytoestrogen]], genistein has [[estrogen|estrogenic]] activity in vitro; consequently, its long-term intake by consuming soy products may affect reproductive organs, such as the [[uterus]] and [[breast]].<ref name=lpi/>

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> Genistein is a primary secondary metabolite of the ''[[Trifolium]]'' species and ''[[Glycine max]]'' (soy).

==Natural occurrences==
Isoflavones, such as genistein and [[daidzein]], occur in soybeans and various other plants, including [[lupin]], [[fava bean]]s, [[kudzu]], [[psoralea]],<ref>{{cite journal |last1=Coward |first1=Lori |last2=Barnes |first2=Neil C. |last3=Setchell |first3=Kenneth D. R. |last4=Barnes |first4=Stephen |year=1993 |title=Genistein, daidzein, and their β-glycoside conjugates: Antitumor isoflavones in soybean foods from American and Asian diets |journal=Journal of Agricultural and Food Chemistry |volume=41 |issue=11 |pages=1961–7 |doi=10.1021/jf00035a027|bibcode=1993JAFC...41.1961C }}</ref><ref>{{cite journal |last1=Kaufman |first1=Peter B. |last2=Duke |first2=James A. |last3=Brielmann |first3=Harry |last4=Boik |first4=John |last5=Hoyt |first5=James E. |year=1997 |title=A Comparative Survey of Leguminous Plants as Sources of the Isoflavones, Genistein and Daidzein: Implications for Human Nutrition and Health |journal=The Journal of Alternative and Complementary Medicine |volume=3 |issue=1 |pages=7–12 |pmid=9395689 |doi=10.1089/acm.1997.3.7 |citeseerx=10.1.1.320.9747}}</ref> ''[[Flemingia vestita]]'',<ref name="Rao">{{cite journal |last1=Rao |first1=H. S. P. |last2=Reddy |first2=K. S. |year=1991 |title=Isoflavones from ''Flemingia vestita'' |journal=Fitoterapia |volume=62 |issue=5 |pages=458}}</ref> and [[coffee]].<ref>{{cite journal |last1=Alves |first1=Rita C. |last2=Almeida |first2=Ivone M. C. |last3=Casal |first3=Susana |last4=Oliveira |first4=M. Beatriz P. P. |year=2010 |title=Isoflavones in Coffee: Influence of Species, Roast Degree, and Brewing Method |journal=Journal of Agricultural and Food Chemistry |volume=58 |issue=5 |pages=3002–7 |pmid=20131840 |doi=10.1021/jf9039205|bibcode=2010JAFC...58.3002A }}</ref> It is present in [[Trifolium pratense|red clover]].<ref name="fda-gsrs">{{cite web |title=Genistein |url=https://precision.fda.gov/uniisearch/srs/unii/dh2m523p0h |publisher=Global Substance Registration System, US Food and Drug Administration |access-date=11 April 2025 |date=2024}}</ref>

==In soybean products==
Isoflavone intake from consuming soy products may be as high as 50 mg per day in Asian cuisines, although it is considerably lower in Western diets.<ref name=lpi/> Genistein has the highest percentage among isoflavones in various soy foods, such as protein concentrate, mature soybeans, and tempeh.<ref name=lpi/>

[[Dietary supplement]]s and [[infant formula]]s containing isoflavone [[extract]]s are marketed in some countries.<ref name=lpi/>

==Metabolism, bioavailability, and safety==
[[Pharmacokinetics]] studies indicate that genistein blood concentrations peak about 6 hours after a meal containing isoflavones, which are [[hydrolysis|hydrolized]] in the [[small intestine]] and [[colon (anatomy)|colon]].<ref name=lpi/>

The colonic [[microbiota]] during [[digestion]] influences the [[metabolism]] of genistein and other isoflavones, converting them to metabolites having potential biological effects, such as the extent of  estrogenic activity.<ref name=lpi/>

Although soy products are [[generally recognized as safe]] (GRAS),<ref name="drugs">{{cite web |title=Soy |url=https://www.drugs.com/npp/soy.html |publisher=Drugs.com |access-date=11 April 2025 |date=12 November 2024}}</ref> a GRAS determination specifically for genistein has not been reported.

==Potential for estrogenic activity==

Because soy isoflavones have similar chemical structure to [[Estradiol|17-β-estradiol]], the potential for genistein as an estrogenic ([[hormone]]-like) [[Cell signaling|signaling molecule]] that binds to estrogen receptors within cells, mimicking the action of [[estrogen]], has been the subject of research. Estrogenic effects by genistein may affect the risk of hormone-associated cancers in reproductive tissues, such as the breast, [[uterus]] or [[prostate gland]], while it may also influence [[bone density]] and levels of [[blood lipids]].<ref name=lpi/>

==Human research==
Although the potential for genistein to have diverse biological activity in humans has been extensively studied, there is only limited evidence of its specific effects.<ref name=drugs/>

In a 2011-12 analysis, a scientific panel for the [[European Food Safety Authority]] found that there was no evidence for a [[causality|cause-and-effect relationship]] between the consumption of genistein with other soy isoflavones and 1) protection of [[DNA]], [[protein]]s and lipids from [[Redox|oxidative]] damage, 2) maintenance of normal blood [[Low-density lipoprotein|LDL-cholesterol]] concentrations, 3) changes in vascular function associated with menopause, 4) normal hair growth or 5) bone mineral density.<ref name="efsa-2011">{{cite journal |author=EFSA Panel on Dietetic Products, Nutrition and Allergies |title=Scientific Opinion on the substantiation of health claims related to soy isoflavones and protection of DNA, proteins and lipids from oxidative damage (ID 1286, 4245), maintenance of normal blood LDL-cholesterol concentrations (ID 1135, 1704a, 3093a), reduction of vasomotor symptoms associated with menopause (ID 1654, 1704b, 2140, 3093b, 3154, 3590), maintenance of normal skin tonicity (ID 1704a), contribution to normal hair growth (ID 1704a, 4254), "cardiovascular health" (ID 3587), treatment of prostate cancer (ID 3588), and "upper respiratory tract" (ID 3589) pursuant to Article 13(1) of Regulation (EC) No 1924/2006 |journal=EFSA Journal |date=2011 |volume=9 |issue=7 |page=2264 |doi=10.2903/j.efsa.2011.2264 |doi-access=free }}</ref><ref name="efsa-2012">{{cite journal |author=EFSA Panel on Dietetic Products, Nutrition and Allergies |title=Scientific Opinion on the substantiation of health claims related to soy isoflavones and maintenance of bone mineral density (ID 1655) and reduction of vasomotor symptoms associated with menopause (ID 1654, 1704, 2140, 3093, 3154, 3590) (further assessment) pursuant toArticle 13(1) of Regulation (EC) No 1924/2006|journal=EFSA Journal |date=2012 |volume=10 |issue=8 |page=2847 |doi=10.2903/j.efsa.2012.2847 |doi-access=free }}</ref> The panel further concluded that there was insufficient evidence that soy isoflavones could affect normal skin tone, respiratory functions, cardiovascular health, or prostate cancer.<ref name=efsa-2011/>

There is preliminary evidence that consuming soy foods rich in genistein and isoflavones may improve [[Cardiovascular physiology|cardiovascular function]] in [[Menopause|postmenopausal]] women<ref name=lpi/> and lower the risk of [[breast cancer]] in premenopausal and postmenopausal women.<ref name="boutas">{{cite journal |vauthors=Boutas I, Kontogeorgi A, Dimitrakakis C, Kalantaridou SN |title=Soy Isoflavones and Breast Cancer Risk: A Meta-analysis |journal=In Vivo |volume=36 |issue=2 |pages=556–562 |date=2022 |pmid=35241506 |pmc=8931889 |doi=10.21873/invivo.12737}}</ref> Some studies indicate that supplementation with genistein and soy isoflavones may reduce [[hot flash]]es and [[night sweats]] during menopause, while there is insufficient evidence for an effect on [[osteoporosis]] and [[cognition|cognitive function]].<ref name=lpi/>

==Laboratory research==

In vitro, genistein is an [[Agonist-antagonist|agonist]] of the [[G protein-coupled estrogen receptor]],<ref name="pmid26023144">{{cite journal |vauthors=Prossnitz ER, Arterburn JB |title=International Union of Basic and Clinical Pharmacology. XCVII. G Protein-Coupled Estrogen Receptor and Its Pharmacologic Modulators |journal=Pharmacol. Rev. |volume=67 |issue=3 |pages=505–40 |date=July 2015 |pmid=26023144 |pmc=4485017 |doi=10.1124/pr.114.009712}}</ref><ref name="ProssnitzBarton2014">{{cite journal |last1=Prossnitz |first1=Eric R. |last2=Barton |first2=Matthias |title=Estrogen biology: New insights into GPER function and clinical opportunities |journal=Molecular and Cellular Endocrinology |volume=389 |issue=1–2 |year=2014 |pages=71–83 |issn=0303-7207 |doi=10.1016/j.mce.2014.02.002 |pmid=24530924 |pmc=4040308}}</ref> and binds to and activates all three [[peroxisome proliferator-activated receptor]] isoforms, α, δ, and γ.<ref name=pmid25083916>{{cite journal |last1=Wang |first1=Limei |last2=Waltenberger |first2=Birgit |last3=Pferschy-Wenzig |first3=Eva-Maria |last4=Blunder |first4=Martina |last5=Liu |first5=Xin |last6=Malainer |first6=Clemens |last7=Blazevic |first7=Tina |last8=Schwaiger |first8=Stefan |last9=Rollinger |first9=Judith M. |last10=Heiss |first10=Elke H. |last11=Schuster |first11=Daniela |last12=Kopp |first12=Brigitte |last13=Bauer |first13=Rudolf |last14=Stuppner |first14=Hermann |last15=Dirsch |first15=Verena M. |last16=Atanasov |first16=Atanas G. |year=2014 |title=Natural product agonists of peroxisome proliferator-activated receptor gamma (PPARγ): A review |journal=Biochemical Pharmacology |pmid=25083916 |doi=10.1016/j.bcp.2014.07.018 |pmc=4212005 |volume=92 |issue=1 |pages=73–89}}</ref><ref>{{cite journal |last1=Dang |first1=Zhi-Chao |last2=Audinot |first2=Valérie |last3=Papapoulos |first3=Socrates E. |last4=Boutin |first4=Jean A. |last5=Löwik |first5=Clemens W. G. M. |year=2002 |title=Peroxisome Proliferator-activated Receptor γ (PPARγ) as a Molecular Target for the Soy Phytoestrogen Genistein |journal=Journal of Biological Chemistry |volume=278 |issue=2 |pages=962–7 |pmid=12421816 |doi=10.1074/jbc.M209483200 |doi-access=free}}</ref> Genistein is a [[tyrosine kinase inhibitor]], mostly of [[epidermal growth factor receptor]]s.<ref name=lpi/>

===Anthelmintic===
The root-tuber peel extract of ''Flemingia vestita'' is a [[traditional medicine]] [[anthelmintics|anthelmintic]] of the [[Khasi people|Khasi tribes]] of India. In research, genistein was found to be the major isoflavone responsible for a [[deworming]] property.<ref name="Rao"/><ref name="Tan">{{cite journal |last1=Tandon |first1=V. |author-link1=Vibha Tandon|last2=Pal |first2=P. |last3=Roy |first3=B. |last4=Rao |first4=H. S. P. |last5=Reddy |first5=K. S. |year=1997 |title=In vitro anthelmintic activity of root-tuber extract of ''Flemingia vestita'', an indigenous plant in Shillong, India |journal=Parasitology Research |volume=83 |issue=5 |pages=492–8 |pmid=9197399 |doi=10.1007/s004360050286 |s2cid=25086153 |url=http://dspace.nehu.ac.in/handle/1/1464|url-access=subscription }}</ref> Genistein was subsequently demonstrated to be effective against [[intestinal parasite]]s, such as the [[poultry]] [[tapeworm|cestode]] ''[[Raillietina echinobothrida]]'',<ref name="Tan"/> the [[pig|pork]] [[trematode]] '' [[Fasciolopsis|Fasciolopsis buski]]'',<ref>{{cite journal |last1=Kar |first1=Pradip K |last2=Tandon |first2=Veena |last3=Saha |first3=Nirmalendu |year=2002 |title=Anthelmintic efficacy of ''Flemingia vestita'': Genistein-induced effect on the activity of nitric oxide synthase and nitric oxide in the trematode parasite, ''Fasciolopsis buski'' |journal=Parasitology International |volume=51 |issue=3 |pages=249–57 |pmid=12243779 |doi=10.1016/S1383-5769(02)00032-6 |url=http://dspace.nehu.ac.in/handle/1/3556|url-access=subscription }}</ref> and the [[Fasciola hepatica|sheep liver fluke ''Fasciola hepatica'']].<ref>{{cite journal |last1=Toner |first1=E. |last2=Brennan |first2=G. P. |last3=Wells |first3=K. |last4=McGeown |first4=J. G. |last5=Fairweather |first5=I. |year=2008 |title=Physiological and morphological effects of genistein against the liver fluke, ''Fasciola hepatica'' |journal=Parasitology |volume=135 |issue=10 |pages=1189–203 |pmid=18771609 |doi=10.1017/S0031182008004630 |s2cid=6525410}}</ref> It exerts its anthelmintic activity by inhibiting [[enzyme]]s of [[glycolysis]] and [[glycogenolysis]] in the parasites.<ref>{{cite journal |last1=Tandon |first1=Veena |last2=Das |first2=Bidyadhar |last3=Saha |first3=Nirmalendu |year=2003 |title=Anthelmintic efficacy of ''Flemingia vestita'' (Fabaceae): Effect of genistein on glycogen metabolism in the cestode, ''Raillietina echinobothrida'' |journal=Parasitology International |volume=52 |issue=2 |pages=179–86 |pmid=12798931 |doi=10.1016/S1383-5769(03)00006-0}}</ref><ref>{{cite journal |last1=Das |first1=B. |last2=Tandon |first2=V. |last3=Saha |first3=N. |year=2004 |title=Anthelmintic efficacy of ''Flemingia vestita'' (Fabaceae): Alteration in the activities of some glycolytic enzymes in the cestode, ''Raillietina echinobothrida'' |journal=Parasitology Research |volume=93 |issue=4 |pages=253–61 |pmid=15138892 |doi=10.1007/s00436-004-1122-8 |s2cid=9491127 |url=http://dspace.nehu.ac.in/handle/1/3458|url-access=subscription }}</ref>

==Related compounds==
* [[Genistin]] is the 7-O-beta-D-[[glucoside]] of genistein.<ref name=lpi/>
* [[Wighteone]] can be described as 6-[[isopentenyl]] genistein

==See also==
* [[(S)-Equol]]
* [[Liquiritigenin]]
* [[Menerba]]

==References==
{{Reflist}}
{{Commons category}}
{{Phytoestrogens}}
{{Isoflavones}}
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[[Category:3α-Hydroxysteroid dehydrogenase inhibitors]]
[[Category:21-Hydroxylase inhibitors]]
[[Category:Dietary supplements]]
[[Category:Flavonoid antioxidants]]
[[Category:GPER agonists]]
[[Category:Isoflavones]]
[[Category:Protein kinase inhibitors]]
[[Category:Phytoestrogens]]
[[Category:Glycine receptor antagonists]]
[[Category:Selective ERβ agonists]]
[[Category:Steroid sulfotransferase inhibitors]]