Genistein: Wikis

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Genistein
Identifiers
CAS number 446-72-0 Yes check.svgY
PubChem 5280961
SMILES
Properties
Molecular formula C15H10O5
Molar mass 270.24 g mol−1
Exact mass 270.052823
 Yes check.svgY (what is this?)  (verify)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Genistein is one of several known isoflavones. Isoflavones, such as genistein and daidzein, are found in a number of plants, with lupin, fava beans, soybeans, kudzu, and psoralea being the primary food source[1]. Besides functioning as antioxidants, 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.

Contents

Biological effects

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Antioxidant

Genistein acts as antioxidant, similar to many other isoflavones, counteracting damaging effects of free radicals in tissues.[2][3]

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.[4]

Cancer links

Genistein and other isoflavones have been found to have antiangiogenic effects (blocking formation of new blood vessels), and may block the uncontrolled cell growth associated with 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 moderate doses of genistein to have inhibitory effects on prostate[5][6], cervical[7], brain[8], and breast[9][10][11] cancers. Some studies have found genistein to increase the rate of proliferation of estrogen-dependent breast cancer when not cotreated with an estrogen antagonist[12][13]. Additionally it has been shown that genistein makes some cells more sensitive to radio-therapy[14]; although, timing of phytoestrogen use is also important.[14]

Studies have also found genistein to be useful in combating leukemia and that it can be used in combination with certain other leukemia combating drugs to improve their efficacy[15].

Genistein's chief method of activity is as a tyrosine kinase inhibitor. Tyrosine kinases are less widespread than their ser/thr counterparts but implicated in almost all cell growth and proliferation signal cascades. Inhibition of DNA topoisomerase II also plays an important role in the cytotoxic activity of genistein. [16][17] Genistein has been used to selectively target pre B-cells via conjugation with an antibody. This highly successful study in mice has promising benefits for future chemotherapy

Effects in males

Isoflavones can act like estrogen, stimulating development and maintenance of female characteristics or they can block cells from using cousins of estrogen. In vitro studies have proven genistein to induce apoptosis of testicular cells at certain levels, thus raising concerns about effects it could have on male fertility[18]; however, a recent study found that isoflavones had "no observable effect on endocrine measurements, testicular volume or semen parameters over the study period." in healthy males given isoflavone supplements daily over a 2 month period.[19]

Molecular function

Genistein influences several targets in living cells. One important function is the inhibition of several tyrosine kinases. Genistein also inhibits the mammalian hexose transporter GLUT1 and contraction of several types of smooth muscles. Genistein can bind to the CFTR channel, potentiating its opening at low concentration and inhibiting it a higher doses.

Related compound

Glycosides

Genistin is the 7-O-beta-D-glucoside of genistein.

Acetylated compounds

Wighteone is the 6-isopentenyl genistein (6-prenyl-5,7,4'-trihydroxyisoflavone)

References

  1. ^ Kaufman PB, Duke JA, Brielmann H, Boik J, Hoyt JE (1997). "A comparative survey of leguminous plants as sources of the isoflavones, genistein and daidzein: implications for human nutrition and health.". J Altern Complement Med 3 (1): 7-12. PMID 9395689. 
  2. ^ Han RM, Tian YX, Liu Y, Chen CH, Ai XC, Zhang JP, Skibsted LH (2009). "Comparison of flavonoids and isoflavonoids as antioxidants". J Agric Food Chem 57 (9): 3780-5. PMID 19296660. 
  3. ^ Borrás C, Gambini J, López-Grueso R, Pallardó FV, Viña J (2009). "Direct antioxidant and protective effect of estradiol on isolated mitochondria.". Biochim Biophys Acta. PMID 19751829. 
  4. ^ Si H, Liu D (2007). "Phytochemical genistein in the regulation of vascular function: new insights". Curr. Med. Chem. 14 (24): 2581–9. doi:10.2174/092986707782023325. PMID 17979711. http://www.bentham-direct.org/pages/content.php?CMC/2007/00000014/00000024/0007C.SGM. 
  5. ^ Keiko MORITO, Toshiharu HIROSE, Junei KINJO, Tomoki HIRAKAWA, Masafumi OKAWA, Toshihiro NOHARA, Sumito OGAWA, Satoshi INOUE, Masami MURAMATSU, and Yukito MASAMUNE (April 2001). "Interaction of Phytoestrogens with Estrogen Receptors a and b". Biol. Pharm. Bull. 24(4) 351—356. http://www.jstage.jst.go.jp/article/bpb/24/4/351/_pdf. 
  6. ^ Hwang YW, Kim SY, Jee SH, Kim YN, Nam CM (2009). "Soy food consumption and risk of prostate cancer: a meta-analysis of observational studies.". Nutr Cancer 61 (5): 598-606. PMID 19838933. 
  7. ^ Kim SH, Kim SH, Kim YB, Jeon YT, Lee SC, Song YS (2009). "Genistein inhibits cell growth by modulating various mitogen-activated protein kinases and AKT in cervical cancer cells.". Ann N Y Acad Sci. 1171: 495-500. PMID 19723095. 
  8. ^ Arabina DAS, Naren L. BANIK, and Swapan K. RAY (2009). "Flavoniods Activated Caspases for Apoptosis in Human Glioblastoma T98G and U87MG Cells But Not in Human Normal Astrocytes". Cancer. PMID 19894226. 
  9. ^ Keiko MORITO, Toshiharu HIROSE, Junei KINJO, Tomoki HIRAKAWA, Masafumi OKAWA, Toshihiro NOHARA, Sumito OGAWA, Satoshi INOUE, Masami MURAMATSU, and Yukito MASAMUNE (April 2001). "Interaction of Phytoestrogens with Estrogen Receptors a and b". Biol. Pharm. Bull. 24(4) 351—356. http://www.jstage.jst.go.jp/article/bpb/24/4/351/_pdf. 
  10. ^ Sakamoto T, Horiguchi H, Oguma E, Kayama F (2009). "Effects of diverse dietary phytoestrogens on cell growth, cell cycle and apoptosis in estrogen-receptor-positive breast cancer cells.". J Nutr Biochem. PMID 19800779. 
  11. ^ de Lemos ML (2001). "Effects of soy phytoestrogens genistein and daidzein on breast cancer growth". Ann Pharmacother 35 (9): 1118-21. PMID 11573864. 
  12. ^ Ju YH, Allred KF, Allred CD, Helferich WG (June 2006). "Genistein stimulates growth of human breast cancer cells in a novel, postmenopausal animal model, with low plasma estradiol concentrations". Carcinogenesis 27 (6): 1292–9. doi:10.1093/carcin/bgi370. PMID 16537557. "Results from this study suggest that consumption of products containing GEN may not be safe for postmenopausal women with estrogen-dependent breast cancer.". 
  13. ^ Chen WF, Wong MS (May 2004). "Genistein enhances insulin-like growth factor signaling pathway in human breast cancer (MCF-7) cells". J. Clin. Endocrinol. Metab. 89 (5): 2351–9. doi:10.1210/jc.2003-032065. PMID 15126563. http://jcem.endojournals.org/cgi/pmidlookup?view=long&pmid=15126563. "These effects could be completely abolished by cotreatment of MCF-7 cells with estrogen antagonist ICI 182780 (1 microM) and tamoxifen (0.1 microM).". 
  14. ^ a b De Assis S, Hilakivi-Clarke L (November 2006). "Timing of dietary estrogenic exposures and breast cancer risk". Ann. N. Y. Acad. Sci. 1089: 14–35. doi:10.1196/annals.1386.039. PMID 17261753. "The viability was decreased by co-treatment with genistein and irradiation compared with irradiation treatment alone.". 
  15. ^ Raynal NJ, Charbonneau M, Momparler LF, Momparler RL (2008). "Synergistic effect of 5-Aza-2'-deoxycytidine and genistein in combination against leukemia". Oncol Res 17 (5): 223-30. PMID 18980019. 
  16. ^ Markovits J, Linassier C, Fossé P, Couprie J, Pierre J, Jacquemin-Sablon A, Saucier JM, Le Pecq JB, Larsen AK (1989). "Inhibitory effects of the tyrosine kinase inhibitor genistein on mammalian DNA topoisomerase II". Cancer Res. 49 (18): 5111–7. PMID 2548712. 
  17. ^ López-Lazaro M, Willmore E, Austin CA. (2007). "Cells lacking DNA topoisomerase II beta are resistant to genistein". J Nat Prod. 70 (5): 763–7. PMID 17411092. 
  18. ^ Kumi-Diaka J, Rodriguez R, Goudaze G (1998). "Influence of genistein (4',5,7-trihydroxyisoflavone) on the growth and proliferation of testicular cell lines". Biol. Cell 90 (4): 349–54. doi:10.1016/S0248-4900(98)80015-4. PMID 9800352. "Genistein-induced apoptosis identifies genistein as a potential diagnostic and therapeutic tool in testicular pathophysiological research.". 
  19. ^ Mitchell JH, Cawood E, Kinniburgh D, Provan A, Collins AR, Irvine DS (2001). "Effect of a phytoestrogen food supplement on reproductive health in normal males.". Clin Sci (Lond) 100 (6): 613-8. PMID 11352776. 

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