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Chemical Compound Review

Biochanin     5,7-dihydroxy-3-(4- methoxyphenyl)chromen-4...

Synonyms: Pratensol, olmelin, Biochanin-A, Biochanine A, biochanin A, ...
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Disease relevance of Biochanin-A


High impact information on Biochanin-A


Chemical compound and disease context of Biochanin-A


Biological context of Biochanin-A


Anatomical context of Biochanin-A

  • These data show that isoflavone metabolism by transformed breast epithelial cells modulates the growth inhibitory effects of genistein and biochanin A [17].
  • We now extend these studies by examining the effects of a novel carboxy-derivative of biochanin A, 6-carboxy-biochanin A (cBA) in VSMC and human osteoblasts in culture. cBA increased DNA synthesis in VSMC in a dose-dependent manner and was able to maintain this effect when linked to a cell membrane impermeable protein [18].
  • RESULTS: The 1.5-h accumulation of digoxin and vinblastine in Caco-2 cells was significantly increased by 50 microM biochanin A or silymarin, and this effect was flavonoid-concentration dependent [19].
  • When genital skin fibroblast homogenates were used, biochanin A was found to inhibit 5 alpha-reductase isozymes 1 and 2 to differing extents (30% and 75% respectively) [20].
  • Various concentrations (0.37-3700 nmol/1) of biochanin A, genistein or oestradiol were added to cultures of bovine granulosa cells and the consequent changes in progesterone synthesis were measured [21].

Associations of Biochanin-A with other chemical compounds


Gene context of Biochanin-A


Analytical, diagnostic and therapeutic context of Biochanin-A


  1. Increased UDP-glucuronosyltransferase activity and decreased prostate specific antigen production by biochanin A in prostate cancer cells. Sun, X.Y., Plouzek, C.A., Henry, J.P., Wang, T.T., Phang, J.M. Cancer Res. (1998) [Pubmed]
  2. Antiproliferative effects of isoflavones on human cancer cell lines established from the gastrointestinal tract. Yanagihara, K., Ito, A., Toge, T., Numoto, M. Cancer Res. (1993) [Pubmed]
  3. Anticarcinogenic effects of isoflavones may be mediated by genistein in mouse mammary tumor virus-induced breast cancer. Mizunuma, H., Kanazawa, K., Ogura, S., Otsuka, S., Nagai, H. Oncology (2002) [Pubmed]
  4. The selective estrogen receptor-beta agonist biochanin A shows vasculoprotective effects without uterotrophic activity. Schrepfer, S., Deuse, T., Münzel, T., Schäfer, H., Braendle, W., Reichenspurner, H. Menopause (New York, N.Y.) (2006) [Pubmed]
  5. Attenuation of mitogen- and stress-activated protein kinase-1-driven nuclear factor-kappaB gene expression by soy isoflavones does not require estrogenic activity. Vanden Berghe, W., Dijsselbloem, N., Vermeulen, L., Ndlovu, N., Boone, E., Haegeman, G. Cancer Res. (2006) [Pubmed]
  6. Use of a mammalian cell culture benzo(a)pyrene metabolism assay for the detection of potential anticarcinogens from natural products: inhibition of metabolism by biochanin A, an isoflavone from Trifolium pratense L. Cassady, J.M., Zennie, T.M., Chae, Y.H., Ferin, M.A., Portuondo, N.E., Baird, W.M. Cancer Res. (1988) [Pubmed]
  7. Plant-derived estrogens relax coronary arteries in vitro by a calcium antagonistic mechanism. Figtree, G.A., Griffiths, H., Lu, Y.Q., Webb, C.M., MacLeod, K., Collins, P. J. Am. Coll. Cardiol. (2000) [Pubmed]
  8. Isoflavones in human breast milk and other biological fluids. Franke, A.A., Custer, L.J., Tanaka, Y. Am. J. Clin. Nutr. (1998) [Pubmed]
  9. Infection of human T lymphoid cells by human herpesvirus 6 is blocked by two unrelated protein tyrosine kinase inhibitors, biochanin A and herbimycin. Cirone, M., Zompetta, C., Tarasi, D., Frati, L., Faggioni, A. AIDS Res. Hum. Retroviruses (1996) [Pubmed]
  10. Biotransformation of the isoflavonoids biochanin A, formononetin, and glycitein by Eubacterium limosum. Hur, H., Rafii, F. FEMS Microbiol. Lett. (2000) [Pubmed]
  11. Suppression of arachidonic acid metabolism and nitric oxide formation by kudzu isoflavones in murine macrophages. Jun, M., Hong, J., Jeong, W.S., Ho, C.T. Molecular nutrition & food research. (2005) [Pubmed]
  12. Inverse association of antioxidant and phytoestrogen nutrient intake with adult glioma in the San Francisco Bay Area: a case-control study. Tedeschi-Blok, N., Lee, M., Sison, J.D., Miike, R., Wrensch, M. BMC Cancer (2006) [Pubmed]
  13. Effects of biochanin A on metabolism, DNA binding and mutagenicity of benzo[a]pyrene in mammalian cell cultures. Chae, Y.H., Coffing, S.L., Cook, V.M., Ho, D.K., Cassady, J.M., Baird, W.M. Carcinogenesis (1991) [Pubmed]
  14. Cell-transforming activity and mutagenicity of 5 phytoestrogens in cultured mammalian cells. Tsutsui, T., Tamura, Y., Yagi, E., Someya, H., Hori, I., Metzler, M., Barrett, J.C. Int. J. Cancer (2003) [Pubmed]
  15. Mechanisms of the growth inhibitory effects of the isoflavonoid biochanin A on LNCaP cells and xenografts. Rice, L., Samedi, V.G., Medrano, T.A., Sweeney, C.A., Baker, H.V., Stenstrom, A., Furman, J., Shiverick, K.T. Prostate (2002) [Pubmed]
  16. Genistein and biochanin A inhibit the growth of human prostate cancer cells but not epidermal growth factor receptor tyrosine autophosphorylation. Peterson, G., Barnes, S. Prostate (1993) [Pubmed]
  17. The role of metabolism in mammary epithelial cell growth inhibition by the isoflavones genistein and biochanin A. Peterson, T.G., Coward, L., Kirk, M., Falany, C.N., Barnes, S. Carcinogenesis (1996) [Pubmed]
  18. Membranal effects of phytoestrogens and carboxy derivatives of phytoestrogens on human vascular and bone cells: new insights based on studies with carboxy-biochanin A. Somjen, D., Kohen, F., Lieberherr, M., Gayer, B., Schejter, E., Katzburg, S., Limor, R., Sharon, O., Knoll, E., Posner, G.H., Kaye, A.M., Stern, N. J. Steroid Biochem. Mol. Biol. (2005) [Pubmed]
  19. Effect of the flavonoids biochanin A and silymarin on the P-glycoprotein-mediated transport of digoxin and vinblastine in human intestinal Caco-2 cells. Zhang, S., Morris, M.E. Pharm. Res. (2003) [Pubmed]
  20. Inhibition of 5 alpha-reductase in genital skin fibroblasts and prostate tissue by dietary lignans and isoflavonoids. Evans, B.A., Griffiths, K., Morton, M.S. J. Endocrinol. (1995) [Pubmed]
  21. Effects of phyto-oestrogens on progesterone synthesis by isolated bovine granulosa cells. Kaplanski, O., Shemesh, M., Berman, A. J. Endocrinol. (1981) [Pubmed]
  22. Phytoestrogen content and estrogenic effect of legume fodder. Saloniemi, H., Wähälä, K., Nykänen-Kurki, P., Kallela, K., Saastamoinen, I. Proc. Soc. Exp. Biol. Med. (1995) [Pubmed]
  23. Differential effects of natural and environmental estrogens on endothelin synthesis in bovine oviduct cells. Reinhart, K.C., Dubey, R.K., Cometti, B., Keller, P.J., Rosselli, M. Biol. Reprod. (2003) [Pubmed]
  24. Effect of various isoflavones on lipid levels in triton-treated rats. Sharma, R.D. Atherosclerosis (1979) [Pubmed]
  25. Up-regulation of interleukin-4 production via NF-AT/AP-1 activation in T cells by biochanin A, a phytoestrogen and its metabolites. Park, J., Chung, S.W., Kim, S.H., Kim, T.S. Toxicol. Appl. Pharmacol. (2006) [Pubmed]
  26. Inhibition of extrahepatic human cytochromes P450 1A1 and 1B1 by metabolism of isoflavones found in Trifolium pratense (red clover). Roberts, D.W., Doerge, D.R., Churchwell, M.I., Gamboa da Costa, G., Marques, M.M., Tolleson, W.H. J. Agric. Food Chem. (2004) [Pubmed]
  27. Effect of biochanin A on the aryl hydrocarbon receptor and cytochrome P450 1A1 in MCF-7 human breast carcinoma cells. Han, E.H., Kim, J.Y., Jeong, H.G. Arch. Pharm. Res. (2006) [Pubmed]
  28. Growth inhibitory effects of flavonoids in human thyroid cancer cell lines. Yin, F., Giuliano, A.E., Van Herle, A.J. Thyroid (1999) [Pubmed]
  29. The isoflavonoids genistein and quercetin activate different stress signaling pathways as shown by analysis of site-specific phosphorylation of ATM, p53 and histone H2AX. Ye, R., Goodarzi, A.A., Kurz, E.U., Saito, S., Higashimoto, Y., Lavin, M.F., Appella, E., Anderson, C.W., Lees-Miller, S.P. DNA Repair (Amst.) (2004) [Pubmed]
  30. Disposition of flavonoids via enteric recycling: enzyme-transporter coupling affects metabolism of biochanin A and formononetin and excretion of their phase II conjugates. Jia, X., Chen, J., Lin, H., Hu, M. J. Pharmacol. Exp. Ther. (2004) [Pubmed]
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