Genistein

Last updated
Genistein
Genistein.svg
Genistein-3D-balls.png
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 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 207-174-9
KEGG
PubChem CID
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 Yes check.svgY
    Key: TZBJGXHYKVUXJN-UHFFFAOYSA-N Yes check.svgY
  • 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).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

Genistein (C15H10O5) 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. [1]

Contents

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] It has been shown to be the primary secondary metabolite of the Trifolium species and Glycine max . [3]

Natural occurrences

Isoflavones such as genistein and daidzein are found in a number of plants including lupin, fava beans, soybeans, kudzu, and psoralea being the primary food source, [4] [5] also in the medicinal plants, Flemingia vestita [6] and F. macrophylla , [7] [8] and coffee. [9] It can also be found in Maackia amurensis cell cultures. [10]

Biological effects

Besides functioning as an antioxidant and anthelmintic, many isoflavones have been shown to interact with animal and human estrogen receptors, causing effects in the body similar to those caused by the hormone estrogen. Isoflavones also produce non-hormonal effects.[ citation needed ]

Molecular function

Genistein influences multiple biochemical functions in living cells:

Activation of PPARs

Isoflavones genistein and daidzein bind to and transactivate all three PPAR isoforms, α, δ, and γ. [20] For example, membrane-bound PPARγ-binding assay showed that genistein can directly interact with the PPARγ ligand binding domain and has a measurable Ki of 5.7 mM. [21] Gene reporter assays showed that genistein at concentrations between 1 and 100 uM activated PPARs in a dose dependent way in KS483 mesenchymal progenitor cells, breast cancer MCF-7 cells, T47D cells and MDA-MD-231 cells, murine macrophage-like RAW 264.7 cells, endothelial cells and in Hela cells. Several studies have shown that both ERs and PPARs influenced each other and therefore induce differential effects in a dose-dependent way. The final biological effects of genistein are determined by the balance among these pleiotrophic actions. [20] [22] [23]

Tyrosine kinase inhibitor

The main known activity of genistein is tyrosine kinase inhibitor, mostly of epidermal growth factor receptor (EGFR). Tyrosine kinases are less widespread than their ser/thr counterparts but implicated in almost all cell growth and proliferation signal cascades.[ citation needed ]

Redox-active—not only antioxidant

Genistein may act as direct antioxidant, similar to many other isoflavones, and thus may alleviate damaging effects of free radicals in tissues. [24] [25]

The same molecule of genistein, similar to many other isoflavones, by generation of free radicals poison topoisomerase II, an enzyme important for maintaining DNA stability. [26] [27] [28]

Human cells turn on beneficial, detoxifying Nrf2 factor in response to genistein insult. This pathway may be responsible for observed health maintaining properties of small doses of genistein. [29]

Anthelmintic

The root-tuber peel extract of the leguminous plant Flemingia vestita is the traditional anthelmintic of the Khasi tribes of India. While investigating its anthelmintic activity, genistein was found to be the major isoflavone responsible for the deworming property. [6] [30] Genistein was subsequently demonstrated to be highly effective against intestinal parasites such as the poultry cestode Raillietina echinobothrida , [30] the pork trematode Fasciolopsis buski , [31] and the sheep liver fluke Fasciola hepatica. [32] It exerts its anthelmintic activity by inhibiting the enzymes of glycolysis and glycogenolysis, [33] [34] and disturbing the Ca2+ homeostasis and NO activity in the parasites. [35] [36] It has also been investigated in human tapeworms such as Echinococcus multilocularis and E. granulosus metacestodes that genistein and its derivatives, Rm6423 and Rm6426, are potent cestocides. [37]

Atherosclerosis

Genistein protects against pro-inflammatory factor-induced vascular endothelial barrier dysfunction and inhibits leukocyte-endothelium interaction, thereby modulating vascular inflammation, a major event in the pathogenesis of atherosclerosis. [38]

Genistein and other isoflavones have been identified as angiogenesis inhibitors, and found to inhibit the uncontrolled cell growth of cancer, most likely by inhibiting the activity of substances in the body that regulate cell division and cell survival (growth factors). Various studies have found that moderate doses of genistein have inhibitory effects on cancers of the prostate, [39] [40] cervix, [41] brain, [42] breast [39] [43] [44] and colon. [17] It has also been shown that genistein makes some cells more sensitive to radio-therapy.

  1. ↑ Sail, Vibhavari; Hadden, M. Kyle (2012-01-01), "Notch Pathway Modulators as Anticancer Chemotherapeutics", in Desai, Manoj C. (ed.), Chapter Eighteen - Notch Pathway Modulators as Anticancer Chemotherapeutics, Annual Reports in Medicinal Chemistry, vol. 47, Academic Press, pp. 267–280, doi:10.1016/B978-0-12-396492-2.00018-7, ISBN   978-0-12-396492-2 , retrieved 2020-09-14
  2. ↑ Walter, E. D. (1941). "Genistin (an Isoflavone Glucoside) and its Aglucone, Genistein, from Soybeans". Journal of the American Chemical Society. 63 (12): 3273–76. doi:10.1021/ja01857a013.
  3. ↑ Popiołkiewicz, Joanna; Polkowski, Krzysztof; Skierski, Janusz S.; Mazurek, Aleksander P. (November 2005). "In vitro toxicity evaluation in the development of new anticancer drugs—genistein glycosides". Cancer Letters. 229 (1): 67–75. doi:10.1016/j.canlet.2005.01.014. ISSN   0304-3835. PMID   16157220.
  4. ↑ Coward, Lori; Barnes, Neil C.; Setchell, Kenneth D. R.; Barnes, Stephen (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. doi:10.1021/jf00035a027.
  5. ↑ Kaufman, Peter B.; Duke, James A.; Brielmann, Harry; Boik, John; Hoyt, James E. (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.
  6. 1 2 Rao, H. S. P.; Reddy, K. S. (1991). "Isoflavones from Flemingia vestita". Fitoterapia. 62 (5): 458.
  7. ↑ Rao, K.Nageswara; Srimannarayana, G. (1983). "Fleminone, a flavanone from the stems of Flemingia macrophylla". Phytochemistry. 22 (10): 2287–90. Bibcode:1983PChem..22.2287R. doi:10.1016/S0031-9422(00)80163-6.
  8. ↑ Wang, Bor-Sen; Juang, Lih-Jeng; Yang, Jeng-Jer; Chen, Li-Ying; Tai, Huo-Mu; Huang, Ming-Hsing (2012). "Antioxidant and Antityrosinase Activity of Flemingia macrophylla and Glycine tomentella Roots". Evidence-Based Complementary and Alternative Medicine. 2012: 1–7. doi: 10.1155/2012/431081 . PMC   3444970 . PMID   22997529.
  9. ↑ Alves, Rita C.; Almeida, Ivone M. C.; Casal, Susana; Oliveira, M. Beatriz P. P. (2010). "Isoflavones in Coffee: Influence of Species, Roast Degree, and Brewing Method". Journal of Agricultural and Food Chemistry. 58 (5): 3002–7. doi:10.1021/jf9039205. PMID   20131840.
  10. ↑ Fedoreyev, S.A; Pokushalova, T.V; Veselova, M.V; Glebko, L.I; Kulesh, N.I; Muzarok, T.I; Seletskaya, L.D; Bulgakov, V.P; Zhuravlev, Yu.N (2000). "Isoflavonoid production by callus cultures of Maackia amurensis". Fitoterapia. 71 (4): 365–72. doi:10.1016/S0367-326X(00)00129-5. PMID   10925005.
  11. ↑ Patisaul, Heather B.; Melby, Melissa; Whitten, Patricia L.; Young, Larry J. (2002). "Genistein Affects ERβ- But Not ERα-Dependent Gene Expression in the Hypothalamus". Endocrinology. 143 (6): 2189–2197. doi: 10.1210/endo.143.6.8843 . ISSN   0013-7227. PMID   12021182.
  12. ↑ Green, Sarah E (2015), In Vitro Comparison of Estrogenic Activities of Popular Women's Health Botanicals, archived from the original on 2016-02-22, retrieved 2016-01-01
  13. ↑ 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.
  14. ↑ Prossnitz, Eric R.; Barton, Matthias (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.
  15. ↑ Gossner, G; Choi, M; Tan, L; Fogoros, S; Griffith, K; Kuenker, M; Liu, J (2007). "Genistein-induced apoptosis and autophagocytosis in ovarian cancer cells". Gynecologic Oncology. 105 (1): 23–30. doi:10.1016/j.ygyno.2006.11.009. PMID   17234261.
  16. ↑ Singletary, K.; Milner, J. (2008). "Diet, Autophagy, and Cancer: A Review". Cancer Epidemiology, Biomarkers & Prevention. 17 (7): 1596–610. doi: 10.1158/1055-9965.EPI-07-2917 . PMID   18628411.
  17. 1 2 Nakamura, Yoshitaka; Yogosawa, Shingo; Izutani, Yasuyuki; Watanabe, Hirotsuna; Otsuji, Eigo; Sakai, Tosiyuki (2009). "A combination of indol-3-carbinol and genistein synergistically induces apoptosis in human colon cancer HT-29 cells by inhibiting Akt phosphorylation and progression of autophagy". Molecular Cancer. 8: 100. doi: 10.1186/1476-4598-8-100 . PMC   2784428 . PMID   19909554.
  18. ↑ Fang, Mingzhu; Chen, Dapeng; Yang, Chung S. (January 2007). "Dietary polyphenols may affect DNA methylation". The Journal of Nutrition. 137 (1 Suppl): 223S–228S. doi: 10.1093/jn/137.1.223S . PMID   17182830.
  19. ↑ Glushakov, A. V.; Glushakova, H. Y.; Skok, V. I. (1999-01-15). "Modulation of nicotinic acetylcholine receptor activity in submucous neurons by intracellular messengers". Journal of the Autonomic Nervous System. 75 (1): 16–22. doi:10.1016/S0165-1838(98)00165-9. ISSN   0165-1838. PMID   9935265.
  20. 1 2 Wang, Limei; Waltenberger, Birgit; Pferschy-Wenzig, Eva-Maria; Blunder, Martina; Liu, Xin; Malainer, Clemens; Blazevic, Tina; Schwaiger, Stefan; Rollinger, Judith M.; Heiss, Elke H.; Schuster, Daniela; Kopp, Brigitte; Bauer, Rudolf; Stuppner, Hermann; Dirsch, Verena M.; Atanasov, Atanas G. (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.
  21. ↑ Dang, Zhi-Chao; Audinot, Valérie; Papapoulos, Socrates E.; Boutin, Jean A.; Löwik, Clemens W. G. M. (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.
  22. ↑ Dang, Zhi Chao; Lowik, Clemens (2005). "Dose-dependent effects of phytoestrogens on bone". Trends in Endocrinology and Metabolism. 16 (5): 207–13. doi:10.1016/j.tem.2005.05.001. PMID   15922618. S2CID   35366615.
  23. ↑ Dang, Z. C. (2009). "Dose-dependent effects of soy phyto-oestrogen genistein on adipocytes: Mechanisms of action". Obesity Reviews. 10 (3): 342–9. doi:10.1111/j.1467-789X.2008.00554.x. PMID   19207876. S2CID   13804244.
  24. ↑ Han, Rui-Min; Tian, Yu-Xi; Liu, Yin; Chen, Chang-Hui; Ai, Xi-Cheng; Zhang, Jian-Ping; Skibsted, Leif H. (2009). "Comparison of Flavonoids and Isoflavonoids as Antioxidants". Journal of Agricultural and Food Chemistry. 57 (9): 3780–5. doi:10.1021/jf803850p. PMID   19296660.
  25. ↑ Borrás, Consuelo; Gambini, Juan; López-Grueso, Raúl; Pallardó, Federico V.; Viña, Jose (2010). "Direct antioxidant and protective effect of estradiol on isolated mitochondria" (PDF). Biochimica et Biophysica Acta (BBA) - Molecular Basis of Disease. 1802 (1): 205–11. doi:10.1016/j.bbadis.2009.09.007. PMID   19751829.
  26. ↑ Bandele, Omari J.; Osheroff, Neil (2007). "Bioflavonoids as Poisons of Human Topoisomerase IIα and IIβ". Biochemistry. 46 (20): 6097–108. doi:10.1021/bi7000664. PMC   2893030 . PMID   17458941.
  27. ↑ Markovits, Judith; Linassier, Claude; Fossé, Philippe; Couprie, Jeanine; Pierre, Josiane; Jacquemin-Sablon, Alain; Saucier, Jean-Marie; Le Pecq, Jean-Bernard; Larsen, Annette K. (September 1989). "Inhibitory effects of the tyrosine kinase inhibitor genistein on mammalian DNA topoisomerase II". Cancer Research. 49 (18): 5111–7. PMID   2548712.
  28. ↑ López-Lázaro, Miguel; Willmore, Elaine; Austin, Caroline A. (2007). "Cells Lacking DNA Topoisomerase IIβ are Resistant to Genistein". Journal of Natural Products. 70 (5): 763–7. doi:10.1021/np060609z. PMID   17411092.
  29. ↑ Mann, Giovanni E; Bonacasa, Barbara; Ishii, Tetsuro; Siow, Richard CM (2009). "Targeting the redox sensitive Nrf2–Keap1 defense pathway in cardiovascular disease: Protection afforded by dietary isoflavones". Current Opinion in Pharmacology. 9 (2): 139–45. doi:10.1016/j.coph.2008.12.012. PMID   19157984.
  30. 1 2 Tandon, V.; Pal, P.; Roy, B.; Rao, H. S. P.; Reddy, K. S. (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.
  31. ↑ Kar, Pradip K; Tandon, Veena; Saha, Nirmalendu (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.
  32. ↑ Toner, E.; Brennan, G. P.; Wells, K.; McGeown, J. G.; Fairweather, I. (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.
  33. ↑ Tandon, Veena; Das, Bidyadhar; Saha, Nirmalendu (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.
  34. ↑ 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.
  35. ↑ Das, Bidyadhar; Tandon, Veena; Saha, Nirmalendu (2006). "Effect of isoflavone from Flemingia vestita (Fabaceae) on the Ca2+ homeostasis in Raillietina echinobothrida, the cestode of domestic fowl". Parasitology International. 55 (1): 17–21. doi:10.1016/j.parint.2005.08.002. PMID   16198617.
  36. ↑ Das, Bidyadhar; Tandon, Veena; Lyndem, Larisha M.; Gray, Alexander I.; Ferro, Valerie A. (2009). "Phytochemicals from Flemingia vestita (Fabaceae) and Stephania glabra (Menispermeaceae) alter cGMP concentration in the cestode Raillietina echinobothrida". Comparative Biochemistry and Physiology C. 149 (3): 397–403. doi:10.1016/j.cbpc.2008.09.012. PMID   18854226.
  37. ↑ Naguleswaran, Arunasalam; Spicher, Martin; Vonlaufen, Nathalie; Ortega-Mora, Luis M.; Torgerson, Paul; Gottstein, Bruno; Hemphill, Andrew (2006). "In Vitro Metacestodicidal Activities of Genistein and Other Isoflavones against Echinococcus multilocularis and Echinococcus granulosus". Antimicrobial Agents and Chemotherapy. 50 (11): 3770–8. doi:10.1128/AAC.00578-06. PMC   1635224 . PMID   16954323.
  38. ↑ Si, Hongwei; Liu, Dongmin; Si, Hongwei; Liu, Dongmin (2007). "Phytochemical Genistein in the Regulation of Vascular Function: New Insights". Current Medicinal Chemistry. 14 (24): 2581–9. doi:10.2174/092986707782023325. PMID   17979711.
  39. 1 2 Morito, Keiko; Hirose, Toshiharu; Kinjo, Junei; Hirakawa, Tomoki; Okawa, Masafumi; Nohara, Toshihiro; Ogawa, Sumito; Inoue, Satoshi; Muramatsu, Masami; Masamune, Yukito (2001). "Interaction of Phytoestrogens with Estrogen Receptors α and β". Biological & Pharmaceutical Bulletin. 24 (4): 351–6. doi: 10.1248/bpb.24.351 . PMID   11305594.
  40. ↑ Hwang, Ye Won; Kim, Soo Young; Jee, Sun Ha; Kim, Youn Nam; Nam, Chung Mo (2009). "Soy Food Consumption and Risk of Prostate Cancer: A Meta-Analysis of Observational Studies". Nutrition and Cancer. 61 (5): 598–606. doi:10.1080/01635580902825639. PMID   19838933. S2CID   19719873.
  41. ↑ Kim, Su-Hyeon; Kim, Su-Hyeong; Kim, Yong-Beom; Jeon, Yong-Tark; Lee, Sang-Chul; Song, Yong-Sang (2009). "Genistein Inhibits Cell Growth by Modulating Various Mitogen-Activated Protein Kinases and AKT in Cervical Cancer Cells". Annals of the New York Academy of Sciences. 1171 (1): 495–500. Bibcode:2009NYASA1171..495K. doi:10.1111/j.1749-6632.2009.04899.x. PMID   19723095. S2CID   26111697.
  42. ↑ Das, Arabinda; Banik, Naren L.; Ray, Swapan K. (2009). "Flavonoids activated caspases for apoptosis in human glioblastoma T98G and U87MG cells but not in human normal astrocytes". Cancer. 116 (1): 164–76. doi:10.1002/cncr.24699. PMC   3159962 . PMID   19894226.
  43. ↑ Sakamoto, Takako; Horiguchi, Hyogo; Oguma, Etsuko; Kayama, Fujio (2010). "Effects of diverse dietary phytoestrogens on cell growth, cell cycle and apoptosis in estrogen-receptor-positive breast cancer cells". The Journal of Nutritional Biochemistry. 21 (9): 856–64. doi:10.1016/j.jnutbio.2009.06.010. PMID   19800779.
  44. ↑ de Lemos, Mário L (2001). "Effects of Soy Phytoestrogens Genistein and Daidzein on Breast Cancer Growth". The Annals of Pharmacotherapy. 35 (9): 1118–21. doi:10.1345/aph.10257. PMID   11573864. S2CID   208876381.

Related Research Articles

Hot flashes are a form of flushing, often caused by the changing hormone levels that are characteristic of menopause. They are typically experienced as a feeling of intense heat with sweating and rapid heartbeat, and may typically last from two to 30 minutes for each occurrence.

<span class="mw-page-title-main">Phytoestrogen</span> Plant-derived xenoestrogen

A phytoestrogen is a plant-derived xenoestrogen not generated within the endocrine system, but consumed by eating plants or manufactured foods. Also called a "dietary estrogen", it is a diverse group of naturally occurring nonsteroidal plant compounds that, because of its structural similarity to estradiol (17-β-estradiol), have the ability to cause estrogenic or antiestrogenic effects. Phytoestrogens are not essential nutrients because their absence from the diet does not cause a disease, nor are they known to participate in any normal biological function. Common foods containing phytoestrogens are soy protein, beans, oats, barley, rice, coffee, apples, carrots.

<span class="mw-page-title-main">Mixed inhibition</span>

Mixed inhibition is a type of enzyme inhibition in which the inhibitor may bind to the enzyme whether or not the enzyme has already bound the substrate but has a greater affinity for one state or the other. It is called "mixed" because it can be seen as a conceptual "mixture" of competitive inhibition, in which the inhibitor can only bind the enzyme if the substrate has not already bound, and uncompetitive inhibition, in which the inhibitor can only bind the enzyme if the substrate has already bound. If the ability of the inhibitor to bind the enzyme is exactly the same whether or not the enzyme has already bound the substrate, it is known as a non-competitive inhibitor. Non-competitive inhibition is sometimes thought of as a special case of mixed inhibition.

<span class="mw-page-title-main">Equol</span> Isoflavandiol estrogen metabolized from daidzein

Equol (4',7-isoflavandiol) is an isoflavandiol estrogen metabolized from daidzein, a type of isoflavone found in soybeans and other plant sources, by bacterial flora in the intestines. While endogenous estrogenic hormones such as estradiol are steroids, equol is a nonsteroidal estrogen. Only about 30–50% of people have intestinal bacteria that make equol.

<span class="mw-page-title-main">Estrogen receptor</span> Proteins activated by the hormone estrogen

Estrogen receptors (ERs) are proteins found in cells that function as receptors for the hormone estrogen (17β-estradiol). There are two main classes of ERs. The first includes the intracellular estrogen receptors, namely ERα and ERβ, which belong to the nuclear receptor family. The second class consists of membrane estrogen receptors (mERs), such as GPER (GPR30), ER-X, and Gq-mER, which are primarily G protein-coupled receptors. This article focuses on the nuclear estrogen receptors.

Isoflavones are substituted derivatives of isoflavone, a type of naturally occurring isoflavonoids, many of which act as phytoestrogens in mammals. Isoflavones occur in many plant species, but are especially high in soybeans.

<span class="mw-page-title-main">Daidzein</span> Chemical compound

Daidzein is a naturally occurring compound found exclusively in soybeans and other legumes and structurally belongs to a class of compounds known as isoflavones. Daidzein and other isoflavones are produced in plants through the phenylpropanoid pathway of secondary metabolism and are used as signal carriers, and defense responses to pathogenic attacks. In humans, recent research has shown the viability of using daidzein in medicine for menopausal relief, osteoporosis, blood cholesterol, and lowering the risk of some hormone-related cancers, and heart disease. Despite the known health benefits, the use of both puerarin and daidzein is limited by their poor bioavailability and low water solubility.

<span class="mw-page-title-main">Emodepside</span> Chemical compound

Emodepside is an anthelmintic drug that is effective against a number of gastrointestinal nematodes, is licensed for use in cats and belongs to the class of drugs known as the octadepsipeptides, a relatively new class of anthelmintic, which are suspected to achieve their anti-parasitic effect by a novel mechanism of action due to their ability to kill nematodes resistant to other anthelmintics.

<span class="mw-page-title-main">Isoflavonoid</span> Class of chemical compound

Isoflavonoids are a class of flavonoid phenolic compounds, many of which are biologically active. Isoflavonoids and their derivatives are sometimes referred to as phytoestrogens, as many isoflavonoid compounds have biological effects via the estrogen receptor.

<span class="mw-page-title-main">Estrogen receptor beta</span> Protein-coding gene in the species Homo sapiens

Estrogen receptor beta (ERβ) also known as NR3A2 is one of two main types of estrogen receptor—a nuclear receptor which is activated by the sex hormone estrogen. In humans ERβ is encoded by the ESR2 gene.

<span class="mw-page-title-main">Estrogen-related receptor alpha</span> Protein-coding gene in the species Homo sapiens

Estrogen-related receptor alpha (ERRα), also known as NR3B1, is a nuclear receptor that in humans is encoded by the ESRRA gene. ERRα was originally cloned by DNA sequence homology to the estrogen receptor alpha, but subsequent ligand binding and reporter-gene transfection experiments demonstrated that estrogens did not regulate ERRα. Currently, ERRα is considered an orphan nuclear receptor.

<span class="mw-page-title-main">Coumestrol</span> Chemical compound

Coumestrol is a natural organic compound in the class of phytochemicals known as coumestans. Coumestrol was first identified as a compound with estrogenic properties by E. M. Bickoff in ladino clover and alfalfa in 1957. It has garnered research interest because of its estrogenic activity and prevalence in some foods, including soybeans, brussels sprouts, spinach and a variety of legumes. The highest concentrations of coumestrol are found in clover, Kala Chana, and Alfalfa sprouts.

<span class="mw-page-title-main">Genistin</span> Chemical compound

Genistin is an isoflavone found in a number of dietary plants like soy and kudzu. It was first isolated in 1931 from the 90% methanol extract of a soybean meal, when it was found that hydrolysis with hydrochloric acid produced 1 mole each of genistein and glucose. Chemically it is the 7-O-beta-D-glucoside form of genistein and is the predominant form of the isoflavone naturally occurring in plants. In fact, studies in the 1970s revealed that 99% of the isoflavonoid compounds in soy are present as their glucosides. The glucosides are converted by digestive enzymes in the digestive system to exert their biological effects. Genistin is also converted to a more familiar genistein, thus, the biological activities including antiatherosclerotic, estrogenic and anticancer effects are analogous.

<i>Raillietina</i> Genus of flatworms

Raillietina is a genus of tapeworms that includes helminth parasites of vertebrates, mostly of birds. The genus was named in 1920 in honour of a French veterinarian and helminthologist, Louis-Joseph Alcide Railliet. Of the 37 species recorded under the genus, Raillietina demerariensis, R. asiatica, and R. formsana are the only species reported from humans, while the rest are found in birds. R. echinobothrida, R. tetragona, and R. cesticillus are the most important species in terms of prevalence and pathogenicity among wild and domestic birds.

<i>Raillietina echinobothrida</i> Species of flatworm

Raillietina echinobothrida is a parasitic tapeworm belonging to the class Cestoda. It is the most prevalent and pathogenic helminth parasite in birds, particularly in domestic fowl, Gallus domesticus Linnaeus, 1758. It requires two hosts, birds and ants, for completion of its life cycle. It is a hermaphrodite worm having both the male and female reproductive organs in its body. The parasite is responsible for 'nodular tapeworm disease' in poultry.

<i>Flemingia vestita</i> Species of legume

Flemingia vestita, famously known as sohphlang, is a nitrogen fixing herb with characteristic tuberous root, belonging to the genus Flemingia. The root is edible and is a common vegetable in some Asian tribal communities. In addition, it has been traditionally used as an anthelmintic, the basis of which is scientifically validated.

Antineoplastic resistance, often used interchangeably with chemotherapy resistance, is the resistance of neoplastic (cancerous) cells, or the ability of cancer cells to survive and grow despite anti-cancer therapies. In some cases, cancers can evolve resistance to multiple drugs, called multiple drug resistance.

<span class="mw-page-title-main">Nonsteroidal estrogen</span> Class of drugs

A nonsteroidal estrogen is an estrogen with a nonsteroidal chemical structure. The most well-known example is the stilbestrol estrogen diethylstilbestrol (DES). Although nonsteroidal estrogens formerly had an important place in medicine, they have gradually fallen out of favor following the discovery of toxicities associated with high-dose DES starting in the early 1970s, and are now almost never used. On the other hand, virtually all selective estrogen receptor modulators (SERMs) are nonsteroidal, with triphenylethylenes like tamoxifen and clomifene having been derived from DES, and these drugs remain widely used in medicine for the treatment of breast cancer among other indications. In addition to pharmaceutical drugs, many xenoestrogens, including phytoestrogens, mycoestrogens, and synthetic endocrine disruptors like bisphenol A, are nonsteroidal substances with estrogenic activity.

<span class="mw-page-title-main">Rimostil</span> Dietary supplement

Rimostil is a dietary supplement and extract of isoflavones from red clover which was under development by Kazia Therapeutics for the prevention of postmenopausal osteoporosis and cardiovascular disease and for the treatment of menopausal symptoms and hyperlipidemia but was never approved for medical use. It is enriched with isoflavone phytoestrogens such as formononetin, biochanin A, daidzein, and genistein, and is proposed to act as a selective estrogen receptor modulator, with both estrogenic and antiestrogenic effects in different tissues. The extract reached phase II clinical trials for cardiovascular disorders, hyperlipidemia, and postmenopausal osteoporosis prior to the discontinuation of its development in 2007.

<i>Soy boy</i> Pejorative term for men perceived as non-masculine

Soy boy is a pejorative term sometimes used in online communities to describe men perceived to be lacking masculine characteristics. The term bears many similarities and has been compared to the slang terms cuck, nu-male and low-T – terms sometimes used as insults for male femininity by online communities.

This page is based on this Wikipedia article
Text is available under the CC BY-SA 4.0 license; additional terms may apply.
Images, videos and audio are available under their respective licenses.