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Chemical Compound Review

Genestein     5,7-dihydroxy-3-(4- hydroxyphenyl)chromen-4...

Synonyms: Prunetol, Bonistein, Genisteol, genistein, Genisterin, ...
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Disease relevance of genistein


Psychiatry related information on genistein

  • These data suggest that genistein is carcinogenic if exposure occurs during critical periods of differentiation [6].
  • OBJECTIVE: The objective was to investigate the bioavailability of the soy isoflavones daidzein and genistein in American women with typical American dietary habits after ingestion of the aglycone or glucoside form of isoflavones [7].
  • Furthermore, genistein, a specific inhibitor of tyrosine kinases, blocked recovery from scopolamine-induced amnesia by S14G-HN, suggesting that certain tyrosine kinase(s) are involved in the inhibitory function of S14G-HN in vivo [8].
  • Since maternal care may affect offspring behaviors in adulthood, it is important to determine the potential for genistein to affect maternal behavior [9].
  • Genistein significantly increased tumor cross-sectional area and tumor multiplicity but not the tumor incidence and latency period when compared with the vehicle treated group [10].

High impact information on genistein


Chemical compound and disease context of genistein


Biological context of genistein

  • Inhibition of PLD activity by genistein or herbimycin A was associated with inhibition of phagocytosis of M. tuberculosis and OZ [21].
  • BACKGROUND: Soy products contain high levels of genistein, a phytoestrogen that is a potent inhibitor of cell proliferation and angiogenesis [22].
  • Third, internalization of lipase-enriched lipoproteins via syndecan-1 and of clustered IgGs via the chimera showed identical kinetics (t1/2 = 1 h) and identical dose-response sensitivities to cytochalasin B, which disrupts microfilaments, and to genistein, which inhibits tyrosine kinases [23].
  • The regulation of secretion by cell volume is not mediated via changes in CCK receptor binding or protein kinase C. The increase of amylase release caused by hypotonicity was completely inhibited by cytochalasin B, colchicine, and genistein [24].
  • The tyrosine kinase inhibitors herbimycin A or genistein blocked both the accumulation of 19 out of 20 signal transduction molecules and JNK- and ERK-mediated signaling [25].

Anatomical context of genistein


Associations of genistein with other chemical compounds


Gene context of genistein


Analytical, diagnostic and therapeutic context of genistein

  • During stimulation with secretagogues, apical extension of CFTR immunofluorescence into the cell was reduced significantly to 3.24+/-0.08 micron by VIP, 4.08+/-0.13 by forskolin, and 3.19+/-0.1 by genistein (P < 0.001) [28].
  • The GM-CSF production by the coculture was markedly inhibited by genistein and partially inhibited by Abs against interleukin-1 and tumor necrosis factor-alpha [42].
  • Herbimycin and genistein reduced by 30% and 50%, respectively, the rise in [Ca2+]i caused by optimal ligation of mIgM, and they abolished it in cells activated by suboptimal ligation of mIgM [43].
  • Isothermal titration calorimetry shows that genistein binds to TTR with negative cooperativity (K(d1) = 40 nM, K(d2) = 1.4 microM) [3].
  • Analysis of individual colonies by cytogenetics and RT-PCR confirmed that genistein-induced increase in the percentage of nonleukemic progenitors was not due to suppression of BCR/ABL transcription [44].


  1. Involvement of p38MAPK in the regulation of proteolysis by liver cell hydration. Häussinger, D., Schliess, F., Dombrowski, F., Vom Dahl, S. Gastroenterology (1999) [Pubmed]
  2. Genistein, a dietary-derived inhibitor of in vitro angiogenesis. Fotsis, T., Pepper, M., Adlercreutz, H., Fleischmann, G., Hase, T., Montesano, R., Schweigerer, L. Proc. Natl. Acad. Sci. U.S.A. (1993) [Pubmed]
  3. Genistein, a natural product from soy, is a potent inhibitor of transthyretin amyloidosis. Green, N.S., Foss, T.R., Kelly, J.W. Proc. Natl. Acad. Sci. U.S.A. (2005) [Pubmed]
  4. Genistein attenuates the hypertensive effects of dietary NaCl in hypertensive male rats. Cho, T.M., Peng, N., Clark, J.T., Novak, L., Roysommuti, S., Prasain, J., Wyss, J.M. Endocrinology (2007) [Pubmed]
  5. Low concentrations of the soy phytoestrogen genistein induce proteinase inhibitor 9 and block killing of breast cancer cells by immune cells. Jiang, X., Patterson, N.M., Ling, Y., Xie, J., Helferich, W.G., Shapiro, D.J. Endocrinology (2008) [Pubmed]
  6. Uterine adenocarcinoma in mice treated neonatally with genistein. Newbold, R.R., Banks, E.P., Bullock, B., Jefferson, W.N. Cancer Res. (2001) [Pubmed]
  7. Bioavailability of soybean isoflavones from aglycone and glucoside forms in American women. Zubik, L., Meydani, M. Am. J. Clin. Nutr. (2003) [Pubmed]
  8. A humanin derivative, S14G-HN, prevents amyloid-beta-induced memory impairment in mice. Tajima, H., Kawasumi, M., Chiba, T., Yamada, M., Yamashita, K., Nawa, M., Kita, Y., Kouyama, K., Aiso, S., Matsuoka, M., Niikura, T., Nishimoto, I. J. Neurosci. Res. (2005) [Pubmed]
  9. Multigenerational exposure to dietary genistein has no severe effects on nursing behavior in rats. Flynn, K.M., Ferguson, S.A., Delclos, K.B., Newbold, R.R. Neurotoxicology (2000) [Pubmed]
  10. Genistein enhances N-nitrosomethylurea-induced rat mammary tumorigenesis. Kijkuokool, P., Parhar, I.S., Malaivijitnond, S. Cancer Lett. (2006) [Pubmed]
  11. A transcription factor with SH2 and SH3 domains is directly activated by an interferon alpha-induced cytoplasmic protein tyrosine kinase(s). Fu, X.Y. Cell (1992) [Pubmed]
  12. Active movement of T cells away from a chemokine. Poznansky, M.C., Olszak, I.T., Foxall, R., Evans, R.H., Luster, A.D., Scadden, D.T. Nat. Med. (2000) [Pubmed]
  13. Hypoxic induction of human vascular endothelial growth factor expression through c-Src activation. Mukhopadhyay, D., Tsiokas, L., Zhou, X.M., Foster, D., Brugge, J.S., Sukhatme, V.P. Nature (1995) [Pubmed]
  14. No requirement for p56lck in the antigen-stimulated clonal deletion of thymocytes. Nakayama, K., Loh, D.Y. Science (1992) [Pubmed]
  15. PDGF-induced activation of phospholipase C is not required for induction of DNA synthesis. Hill, T.D., Dean, N.M., Mordan, L.J., Lau, A.F., Kanemitsu, M.Y., Boynton, A.L. Science (1990) [Pubmed]
  16. Epidermal growth factor inhibits carbachol-stimulated canine parietal cell function via protein kinase C. Wang, L., Wilson, E.J., Osburn, J., DelValle, J. Gastroenterology (1996) [Pubmed]
  17. Angiogenic factors stimulate mast-cell migration. Gruber, B.L., Marchese, M.J., Kew, R. Blood (1995) [Pubmed]
  18. Molecular evidence for increased antitumor activity of gemcitabine by genistein in vitro and in vivo using an orthotopic model of pancreatic cancer. Banerjee, S., Zhang, Y., Ali, S., Bhuiyan, M., Wang, Z., Chiao, P.J., Philip, P.A., Abbruzzese, J., Sarkar, F.H. Cancer Res. (2005) [Pubmed]
  19. Estrogenic effects of genistein on the growth of estrogen receptor-positive human breast cancer (MCF-7) cells in vitro and in vivo. Hsieh, C.Y., Santell, R.C., Haslam, S.Z., Helferich, W.G. Cancer Res. (1998) [Pubmed]
  20. Inactivation of nuclear factor kappaB by soy isoflavone genistein contributes to increased apoptosis induced by chemotherapeutic agents in human cancer cells. Li, Y., Ahmed, F., Ali, S., Philip, P.A., Kucuk, O., Sarkar, F.H. Cancer Res. (2005) [Pubmed]
  21. Activation of phospholipase D is tightly coupled to the phagocytosis of Mycobacterium tuberculosis or opsonized zymosan by human macrophages. Kusner, D.J., Hall, C.F., Schlesinger, L.S. J. Exp. Med. (1996) [Pubmed]
  22. Mechanism for the suppression of the mammalian stress response by genistein, an anticancer phytoestrogen from soy. Zhou, Y., Lee, A.S. J. Natl. Cancer Inst. (1998) [Pubmed]
  23. The syndecan family of proteoglycans. Novel receptors mediating internalization of atherogenic lipoproteins in vitro. Fuki, I.V., Kuhn, K.M., Lomazov, I.R., Rothman, V.L., Tuszynski, G.P., Iozzo, R.V., Swenson, T.L., Fisher, E.A., Williams, K.J. J. Clin. Invest. (1997) [Pubmed]
  24. Cell volume changes modulate cholecystokinin- and carbachol-stimulated amylase release in isolated rat pancreatic acini. Han, B., Klonowski-Stumpe, H., Schliess, F., Meereis-Schwanke, K., Lüthen, R., Sata, N., Häussinger, D., Niederau, C. Gastroenterology (1997) [Pubmed]
  25. Integrin function: molecular hierarchies of cytoskeletal and signaling molecules. Miyamoto, S., Teramoto, H., Coso, O.A., Gutkind, J.S., Burbelo, P.D., Akiyama, S.K., Yamada, K.M. J. Cell Biol. (1995) [Pubmed]
  26. Influence of genistein and daidzein on Brca1 protein levels in human breast cell lines. Bernard-Gallon, D.J., Maurizis, J.C., Rio, P.G., Bignon, Y.J. J. Natl. Cancer Inst. (1998) [Pubmed]
  27. Characterization of vascular endothelial growth factor's effect on the activation of protein kinase C, its isoforms, and endothelial cell growth. Xia, P., Aiello, L.P., Ishii, H., Jiang, Z.Y., Park, D.J., Robinson, G.S., Takagi, H., Newsome, W.P., Jirousek, M.R., King, G.L. J. Clin. Invest. (1996) [Pubmed]
  28. Vasoactive intestinal peptide, forskolin, and genistein increase apical CFTR trafficking in the rectal gland of the spiny dogfish, Squalus acanthias. Acute regulation of CFTR trafficking in an intact epithelium. Lehrich, R.W., Aller, S.G., Webster, P., Marino, C.R., Forrest, J.N. J. Clin. Invest. (1998) [Pubmed]
  29. Tyrosine phosphorylation of membrane proteins mediates cellular invasion by transformed cells. Mueller, S.C., Yeh, Y., Chen, W.T. J. Cell Biol. (1992) [Pubmed]
  30. Growth inhibition with reversible cell cycle arrest of carcinoma cells by flavone L86-8275. Kaur, G., Stetler-Stevenson, M., Sebers, S., Worland, P., Sedlacek, H., Myers, C., Czech, J., Naik, R., Sausville, E. J. Natl. Cancer Inst. (1992) [Pubmed]
  31. Macrophage role in the anti-prostate cancer response to one class of antiangiogenic agents. Joseph, I.B., Isaacs, J.T. J. Natl. Cancer Inst. (1998) [Pubmed]
  32. Bile salt-induced hepatocyte apoptosis involves epidermal growth factor receptor-dependent CD95 tyrosine phosphorylation. Reinehr, R., Graf, D., Häussinger, D. Gastroenterology (2003) [Pubmed]
  33. Structure of the ligand-binding domain of oestrogen receptor beta in the presence of a partial agonist and a full antagonist. Pike, A.C., Brzozowski, A.M., Hubbard, R.E., Bonn, T., Thorsell, A.G., Engström, O., Ljunggren, J., Gustafsson, J.A., Carlquist, M. EMBO J. (1999) [Pubmed]
  34. Effects of the phytoestrogen genistein on some predictors of cardiovascular risk in osteopenic, postmenopausal women: a two-year randomized, double-blind, placebo-controlled study. Atteritano, M., Marini, H., Minutoli, L., Polito, F., Bitto, A., Altavilla, D., Mazzaferro, S., D'Anna, R., Cannata, M.L., Gaudio, A., Frisina, A., Frisina, N., Corrado, F., Cancellieri, F., Lubrano, C., Bonaiuto, M., Adamo, E.B., Squadrito, F. J. Clin. Endocrinol. Metab. (2007) [Pubmed]
  35. Involvement of a soybean ATP-binding cassette-type transporter in the secretion of genistein, a signal flavonoid in legume-Rhizobium symbiosis. Sugiyama, A., Shitan, N., Yazaki, K. Plant Physiol. (2007) [Pubmed]
  36. ERK1 and ERK2, two microtubule-associated protein 2 kinases, mediate the phosphorylation of tyrosine hydroxylase at serine-31 in situ. Haycock, J.W., Ahn, N.G., Cobb, M.H., Krebs, E.G. Proc. Natl. Acad. Sci. U.S.A. (1992) [Pubmed]
  37. Genistein reduces tumor necrosis factor alpha-induced plasminogen activator inhibitor-1 transcription but not urokinase expression in human endothelial cells. van Hinsbergh, V.W., Vermeer, M., Koolwijk, P., Grimbergen, J., Kooistra, T. Blood (1994) [Pubmed]
  38. Arachidonic acid induces c-jun gene expression in stromal cells stimulated by interleukin-1 and tumor necrosis factor-alpha: evidence for a tyrosine-kinase-dependent process. Rizzo, M.T., Boswell, H.S., Mangoni, L., Carlo-Stella, C., Rizzoli, V. Blood (1995) [Pubmed]
  39. Activation of pp125FAK by type 2B recombinant von Willebrand factor binding to platelet GPIb at a high shear rate occurs independently of alpha IIb beta 3 engagement. Mekrache, M., Bachelot-Loza, C., Ajzenberg, N., Saci, A., Legendre, P., Baruch, D. Blood (2003) [Pubmed]
  40. The C-class chemokine, lymphotactin, impairs the induction of Th1-type lymphokines in human CD4(+) T cells. Cerdan, C., Serfling, E., Olive, D. Blood (2000) [Pubmed]
  41. Genistein inhibits Brca1 mutant tumor growth through activation of DNA damage checkpoints, cell cycle arrest, and mitotic catastrophe. Tominaga, Y., Wang, A., Wang, R.H., Wang, X., Cao, L., Deng, C.X. Cell Death Differ. (2007) [Pubmed]
  42. Human monocyte-endothelial cell interaction induces synthesis of granulocyte-macrophage colony-stimulating factor. Takahashi, M., Kitagawa, S., Masuyama, J.I., Ikeda, U., Kasahara, T., Takahashi, Y.I., Furukawa, Y., Kano, S., Shimada, K. Circulation (1996) [Pubmed]
  43. Tyrosine phosphorylation of phospholipase C induced by membrane immunoglobulin in B lymphocytes. Carter, R.H., Park, D.J., Rhee, S.G., Fearon, D.T. Proc. Natl. Acad. Sci. U.S.A. (1991) [Pubmed]
  44. Selection of myeloid progenitors lacking BCR/ABL mRNA in chronic myelogenous leukemia patients after in vitro treatment with the tyrosine kinase inhibitor genistein. Carlo-Stella, C., Dotti, G., Mangoni, L., Regazzi, E., Garau, D., Bonati, A., Almici, C., Sammarelli, G., Savoldo, B., Rizzo, M.T., Rizzoli, V. Blood (1996) [Pubmed]
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