Jump to content

Genistein

From Wikipedia, the free encyclopedia
Not to be confused with Genistin.

Genistein
Genistein molecule
Names
IUPAC name
4′,5,7-Trihydroxyisoflavone
Systematic IUPAC name
5,7-Dihydroxy-3-(4-hydroxyphenyl)-4H-1-benzopyran-4-one
Identifiers
3D model (JSmol)
263823
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.006.524 Edit this at Wikidata
EC Number
  • 207-174-9
KEGG
UNII
  • InChI=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 checkY
    Key: TZBJGXHYKVUXJN-UHFFFAOYSA-N checkY
  • 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
    Key: TZBJGXHYKVUXJN-UHFFFAOYAH
  • Oc1ccc(cc1)C\3=C\Oc2cc(O)cc(O)c2C/3=O
Properties
C15H10O5
Molar mass 270.240 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

Genistein (C15H10O5) is a plant-derived, aglycone isoflavone.[1] Genistein has the highest content of all isoflavones in soybeans and soy products, such as tempeh. As a type of phytoestrogen, genistein has estrogenic activity in vitro; consequently, its long-term intake by consuming soy products may affect reproductive organs, such as the uterus and breast.[1]

It was first isolated in 1899 from the 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.[2] Genistein is a primary secondary metabolite of the Trifolium species and Glycine max.

Natural occurrences

[edit]

Isoflavones, such as genistein and daidzein, occur in soybeans and various other plants, including lupin, fava beans, kudzu, psoralea,[3][4] Flemingia vestita,[5] and coffee.[6] It is present in red clover.[7]

In soybean products

[edit]

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.[1] Genistein has the highest percentage among isoflavones in various soy foods, such as protein concentrate, mature soybeans, and tempeh.[1]

Dietary supplements and infant formulas containing isoflavone extracts are marketed in some countries.[1]

Metabolism, bioavailability, and safety

[edit]

Pharmacokinetics studies indicate that genistein blood concentrations peak about 6 hours after a meal containing isoflavones, which are hydrolized in the small intestine and colon.[1]

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.[1]

Although soy products are generally recognized as safe (GRAS),[8] a GRAS determination specifically for genistein has not been reported.

Potential for estrogenic activity

[edit]

Because soy isoflavones have similar chemical structure to 17-β-estradiol, the potential for genistein as an estrogenic (hormone-like) 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.[1]

Human research

[edit]

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.[8]

In a 2011-12 analysis, a scientific panel for the European Food Safety Authority found that there was no evidence for a cause-and-effect relationship between the consumption of genistein with other soy isoflavones and 1) protection of DNA, proteins and lipids from oxidative damage, 2) maintenance of normal blood LDL-cholesterol concentrations, 3) changes in vascular function associated with menopause, 4) normal hair growth or 5) bone mineral density.[9][10] The panel further concluded that there was insufficient evidence that soy isoflavones could affect normal skin tone, respiratory functions, cardiovascular health, or prostate cancer.[9]

There is preliminary evidence that consuming soy foods rich in genistein and isoflavones may improve cardiovascular function in postmenopausal women[1] and lower the risk of breast cancer in premenopausal and postmenopausal women.[11] Some studies indicate that supplementation with genistein and soy isoflavones may reduce hot flashes and night sweats during menopause, while there is insufficient evidence for an effect on osteoporosis and cognitive function.[1]

Laboratory research

[edit]

In vitro, genistein is an agonist of the G protein-coupled estrogen receptor,[12][13] and binds to and activates all three peroxisome proliferator-activated receptor isoforms, α, δ, and γ.[14][15] Genistein is a tyrosine kinase inhibitor, mostly of epidermal growth factor receptors.[1]

Anthelmintic

[edit]

The root-tuber peel extract of Flemingia vestita is a traditional medicine anthelmintic of the Khasi tribes of India. In research, genistein was found to be the major isoflavone responsible for a deworming property.[5][16] Genistein was subsequently demonstrated to be effective against intestinal parasites, such as the poultry cestode Raillietina echinobothrida,[16] the pork trematode Fasciolopsis buski,[17] and the sheep liver fluke Fasciola hepatica.[18] It exerts its anthelmintic activity by inhibiting enzymes of glycolysis and glycogenolysis in the parasites.[19][20]

[edit]

See also

[edit]

References

[edit]
  1. ^ a b c d e f g h i j k l "Soy isoflavones". Micronutrient Information Center, Linus Pauling Institute, Oregon State University. 2025. Retrieved 9 April 2025.
  2. ^ Walter ED (1941). "Genistin (an Isoflavone Glucoside) and its Aglucone, Genistein, from Soybeans". Journal of the American Chemical Society. 63 (12): 3273–76. Bibcode:1941JAChS..63.3273W. doi:10.1021/ja01857a013.
  3. ^ Coward L, Barnes NC, Setchell KD, et al. (1993). "Genistein, daidzein, and their β-glycoside conjugates: Antitumor isoflavones in soybean foods from American and Asian diets". Journal of Agricultural and Food Chemistry. 41 (11): 1961–7. Bibcode:1993JAFC...41.1961C. doi:10.1021/jf00035a027.
  4. ^ Kaufman PB, Duke JA, Brielmann H, et al. (1997). "A Comparative Survey of Leguminous Plants as Sources of the Isoflavones, Genistein and Daidzein: Implications for Human Nutrition and Health". The Journal of Alternative and Complementary Medicine. 3 (1): 7–12. CiteSeerX 10.1.1.320.9747. doi:10.1089/acm.1997.3.7. PMID 9395689.
  5. ^ a b Rao HS, Reddy KS (1991). "Isoflavones from Flemingia vestita". Fitoterapia. 62 (5): 458.
  6. ^ Alves RC, Almeida IM, Casal S, et al. (2010). "Isoflavones in Coffee: Influence of Species, Roast Degree, and Brewing Method". Journal of Agricultural and Food Chemistry. 58 (5): 3002–7. Bibcode:2010JAFC...58.3002A. doi:10.1021/jf9039205. PMID 20131840.
  7. ^ "Genistein". Global Substance Registration System, US Food and Drug Administration. 2024. Retrieved 11 April 2025.
  8. ^ a b "Soy". Drugs.com. 12 November 2024. Retrieved 11 April 2025.
  9. ^ a b EFSA Panel on Dietetic Products, Nutrition and Allergies (2011). "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". EFSA Journal. 9 (7): 2264. doi:10.2903/j.efsa.2011.2264.
  10. ^ EFSA Panel on Dietetic Products, Nutrition and Allergies (2012). "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". EFSA Journal. 10 (8): 2847. doi:10.2903/j.efsa.2012.2847.
  11. ^ Boutas I, Kontogeorgi A, Dimitrakakis C, et al. (2022). "Soy Isoflavones and Breast Cancer Risk: A Meta-analysis". In Vivo. 36 (2): 556–562. doi:10.21873/invivo.12737. PMC 8931889. PMID 35241506.
  12. ^ Prossnitz ER, Arterburn JB (July 2015). "International Union of Basic and Clinical Pharmacology. XCVII. G Protein-Coupled Estrogen Receptor and Its Pharmacologic Modulators". Pharmacol. Rev. 67 (3): 505–40. doi:10.1124/pr.114.009712. PMC 4485017. PMID 26023144.
  13. ^ Prossnitz ER, Barton M (2014). "Estrogen biology: New insights into GPER function and clinical opportunities". Molecular and Cellular Endocrinology. 389 (1–2): 71–83. doi:10.1016/j.mce.2014.02.002. ISSN 0303-7207. PMC 4040308. PMID 24530924.
  14. ^ Wang L, Waltenberger B, Pferschy-Wenzig EM, et al. (2014). "Natural product agonists of peroxisome proliferator-activated receptor gamma (PPARγ): A review". Biochemical Pharmacology. 92 (1): 73–89. doi:10.1016/j.bcp.2014.07.018. PMC 4212005. PMID 25083916.
  15. ^ Dang ZC, Audinot V, Papapoulos SE, et al. (2002). "Peroxisome Proliferator-activated Receptor γ (PPARγ) as a Molecular Target for the Soy Phytoestrogen Genistein". Journal of Biological Chemistry. 278 (2): 962–7. doi:10.1074/jbc.M209483200. PMID 12421816.
  16. ^ a b Tandon V, Pal P, Roy B, et al. (1997). "In vitro anthelmintic activity of root-tuber extract of Flemingia vestita, an indigenous plant in Shillong, India". Parasitology Research. 83 (5): 492–8. doi:10.1007/s004360050286. PMID 9197399. S2CID 25086153.
  17. ^ Kar PK, Tandon V, Saha N (2002). "Anthelmintic efficacy of Flemingia vestita: Genistein-induced effect on the activity of nitric oxide synthase and nitric oxide in the trematode parasite, Fasciolopsis buski". Parasitology International. 51 (3): 249–57. doi:10.1016/S1383-5769(02)00032-6. PMID 12243779.
  18. ^ Toner E, Brennan GP, Wells K, et al. (2008). "Physiological and morphological effects of genistein against the liver fluke, Fasciola hepatica". Parasitology. 135 (10): 1189–203. doi:10.1017/S0031182008004630. PMID 18771609. S2CID 6525410.
  19. ^ Tandon V, Das B, Saha N (2003). "Anthelmintic efficacy of Flemingia vestita (Fabaceae): Effect of genistein on glycogen metabolism in the cestode, Raillietina echinobothrida". Parasitology International. 52 (2): 179–86. doi:10.1016/S1383-5769(03)00006-0. PMID 12798931.
  20. ^ Das B, Tandon V, Saha N (2004). "Anthelmintic efficacy of Flemingia vestita (Fabaceae): Alteration in the activities of some glycolytic enzymes in the cestode, Raillietina echinobothrida". Parasitology Research. 93 (4): 253–61. doi:10.1007/s00436-004-1122-8. PMID 15138892. S2CID 9491127.
Wikimedia Commons has media related to Genistein.
Retrieved from "https://en.wikipedia.org/w/index.php?title=Genistein&oldid=1285505649"