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Chemical Compound Review

isoflavon     3-phenylchromen-4-one

Synonyms: Isoflavone, iso-flavone, SureCN8028, CHEMBL366460, CHEBI:18220, ...
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Disease relevance of C00799


Psychiatry related information on C00799


High impact information on C00799

  • We expressed soybean isoflavone synthase in Arabidopsis thaliana, which led to production of the isoflavone genistein in this nonlegume plant [11].
  • However, isoflavone O-methyltransferase (IOMT) from alfalfa converts the isoflavone daidzein to 7-O-methyl daidzein (isoformononetin) in vitro as well as in vivo in unchallenged leaves of transgenic alfalfa ectopically expressing IOMT [12].
  • Genetic manipulation of isoflavone 7-O-methyltransferase enhances biosynthesis of 4'-O-methylated isoflavonoid phytoalexins and disease resistance in alfalfa [12].
  • The predicted polypeptide is highly homologous ( > 70%) to leguminous isoflavone reductases (IFRs), but the maize protein (IRL for isoflavone reductase-like) belongs to a novel family of proteins present in a variety of plants [13].
  • A maize gene encoding an NADPH binding enzyme highly homologous to isoflavone reductases is activated in response to sulfur starvation [13].

Chemical compound and disease context of C00799


Biological context of C00799


Anatomical context of C00799

  • Here we report that the isoflavone compound genistein prevents the increase in synthesis of PAI-1 induced by these inflammatory mediators in human endothelial cells in vitro, and partially reduces the basal PAI-1 production by these cells [22].
  • Plasma isoflavone concentrations reported previously for 4-mo-old infants fed soy-based formula were 654-1775 microg/L (mean: 979.7 microg/L: Lancet 1997:350;23-7), significantly higher than plasma concentrations of infants fed either cow-milk formula (mean +/- SD: 9.4 +/- 1.2 microg/L) or human breast milk (4.7 +/- 1.3 microg/L) [23].
  • The recombinant enzymes in yeast microsomes utilized the same isoflavone substrates, but produced different products hydroxylated at the 2' and/or 3' positions of the B-ring [24].
  • Soy isoflavone supplementation in healthy men prevents NF-kappa B activation by TNF-alpha in blood lymphocytes [25].
  • The possibility that the heightened cardiovascular risk associated with the menopause can be reduced by increasing dietary isoflavone intake was tested in 17 women by measuring arterial compliance, an index of the elasticity of large arteries such as the thoracic aorta [26].

Associations of C00799 with other chemical compounds


Gene context of C00799

  • Both inhibitors decreased basal production of prostacyclin, but only COX-2 inhibition completely abolished the isoflavone-stimulated prostacyclin production [32].
  • These data suggest an important interplay between the p38 pathway and G2 cell cycle checkpoint control and provide insights into possible mechanisms whereby this isoflavone may inhibit early events in mammary carcinogenesis [33].
  • Thus, high levels of isoflavone intake appear to increase serum concentrations of IL-6 in women [34].
  • CYP1A1 catalyzed isoflavone 4'-O-demethylation and hydroxylations with similar efficiency, whereas CYP1B1 favored 4'-O-demethylation over hydroxylations [35].
  • In the present study, genistein was found to be an effective inhibitor of recombinant human CYP1A1 and CYP1B1 with Ki of 15.35 and 0.68 micromol/l. The other soya isoflavone daidzein, on the other hand, did not demonstrate any significant inhibition of the enzyme activities [36].

Analytical, diagnostic and therapeutic context of C00799

  • The HPLC conditions for soy isoflavone analysis were improved, leading to good separation with a short analysis time (60 min/sample) [37].
  • In 2 randomized, cross-over studies, 14 pre- and 17 postmenopausal women were given 3 soy protein isolates containing different amounts of isoflavones [control, 0.13; low isoflavone (low-iso), 1.00; and high-iso, 2.01 mg/kg body wt/day, averaging 8, 65, and 130 mg/day, respectively], for over 3 months each [38].
  • BACKGROUND: Isoflavone phytoestrogen therapy has been proposed as a natural alternative to hormone replacement therapy (HRT) [39].
  • DESIGN: In this cross-sectional study, soy isoflavone intake and plasma isoflavone concentration were analyzed in 96 postmenopausal women aged 50-79 y; the data were obtained at 2 visits that were 1 wk apart [7].
  • OBJECTIVE: To assess the biological activity of isoflavone phytoestrogens, we analyzed the effect of dietary soy isoflavone supplementation on in vivo bioassays of estrogenicity [40].


  1. Gene expression in tobacco low-nicotine mutants. Hibi, N., Higashiguchi, S., Hashimoto, T., Yamada, Y. Plant Cell (1994) [Pubmed]
  2. Dietary genistein negates the inhibitory effect of tamoxifen on growth of estrogen-dependent human breast cancer (MCF-7) cells implanted in athymic mice. Ju, Y.H., Doerge, D.R., Allred, K.F., Allred, C.D., Helferich, W.G. Cancer Res. (2002) [Pubmed]
  3. Genistein represses telomerase activity via both transcriptional and posttranslational mechanisms in human prostate cancer cells. Jagadeesh, S., Kyo, S., Banerjee, P.P. Cancer Res. (2006) [Pubmed]
  4. Soy phytochemicals prevent orthotopic growth and metastasis of bladder cancer in mice by alterations of cancer cell proliferation and apoptosis and tumor angiogenesis. Singh, A.V., Franke, A.A., Blackburn, G.L., Zhou, J.R. Cancer Res. (2006) [Pubmed]
  5. 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]
  6. Evolution of plant defense mechanisms. Relationships of phenylcoumaran benzylic ether reductases to pinoresinol-lariciresinol and isoflavone reductases. Gang, D.R., Kasahara, H., Xia, Z.Q., Vander Mijnsbrugge, K., Bauw, G., Boerjan, W., Van Montagu, M., Davin, L.B., Lewis, N.G. J. Biol. Chem. (1999) [Pubmed]
  7. Validation of a soy food-frequency questionnaire and evaluation of correlates of plasma isoflavone concentrations in postmenopausal women. Frankenfeld, C.L., Patterson, R.E., Horner, N.K., Neuhouser, M.L., Skor, H.E., Kalhorn, T.F., Howald, W.N., Lampe, J.W. Am. J. Clin. Nutr. (2003) [Pubmed]
  8. Long-term dietary habits affect soy isoflavone metabolism and accumulation in prostatic fluid in caucasian men. Hedlund, T.E., Maroni, P.D., Ferucci, P.G., Dayton, R., Barnes, S., Jones, K., Moore, R., Ogden, L.G., Wähälä, K., Sackett, H.M., Gray, K.J. J. Nutr. (2005) [Pubmed]
  9. Soy isoflavone conjugation differs in fed and food-deprived rats. Piskula, M.K. J. Nutr. (2000) [Pubmed]
  10. Premenopausal equol excretors show plasma hormone profiles associated with lowered risk of breast cancer. Duncan, A.M., Merz-Demlow, B.E., Xu, X., Phipps, W.R., Kurzer, M.S. Cancer Epidemiol. Biomarkers Prev. (2000) [Pubmed]
  11. Identification and expression of isoflavone synthase, the key enzyme for biosynthesis of isoflavones in legumes. Jung, W., Yu, O., Lau, S.M., O'Keefe, D.P., Odell, J., Fader, G., McGonigle, B. Nat. Biotechnol. (2000) [Pubmed]
  12. Genetic manipulation of isoflavone 7-O-methyltransferase enhances biosynthesis of 4'-O-methylated isoflavonoid phytoalexins and disease resistance in alfalfa. He, X.Z., Dixon, R.A. Plant Cell (2000) [Pubmed]
  13. A maize gene encoding an NADPH binding enzyme highly homologous to isoflavone reductases is activated in response to sulfur starvation. Petrucco, S., Bolchi, A., Foroni, C., Percudani, R., Rossi, G.L., Ottonello, S. Plant Cell (1996) [Pubmed]
  14. Soy diets containing varying amounts of genistein stimulate growth of estrogen-dependent (MCF-7) tumors in a dose-dependent manner. Allred, C.D., Allred, K.F., Ju, Y.H., Virant, S.M., Helferich, W.G. Cancer Res. (2001) [Pubmed]
  15. Effects of ipriflavone and its metabolites on a clonal osteoblastic cell line. Benvenuti, S., Tanini, A., Frediani, U., Bianchi, S., Masi, L., Casano, R., Bufalino, L., Serio, M., Brandi, M.L. J. Bone Miner. Res. (1991) [Pubmed]
  16. Dietary phytoestrogens and breast cancer risk. Keinan-Boker, L., van Der Schouw, Y.T., Grobbee, D.E., Peeters, P.H. Am. J. Clin. Nutr. (2004) [Pubmed]
  17. 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]
  18. Decreased ovarian hormones during a soya diet: implications for breast cancer prevention. Lu, L.J., Anderson, K.E., Grady, J.J., Kohen, F., Nagamani, M. Cancer Res. (2000) [Pubmed]
  19. Genistein, a dietary isoflavone, down-regulates the MDM2 oncogene at both transcriptional and posttranslational levels. Li, M., Zhang, Z., Hill, D.L., Chen, X., Wang, H., Zhang, R. Cancer Res. (2005) [Pubmed]
  20. (+)-Pinoresinol/(+)-lariciresinol reductase from Forsythia intermedia. Protein purification, cDNA cloning, heterologous expression and comparison to isoflavone reductase. Dinkova-Kostova, A.T., Gang, D.R., Davin, L.B., Bedgar, D.L., Chu, A., Lewis, N.G. J. Biol. Chem. (1996) [Pubmed]
  21. The Isoflavone Equol Mediates Rapid Vascular Relaxation: Ca2+-INDEPENDENT ACTIVATION OF ENDOTHELIAL NITRIC-OXIDE SYNTHASE/Hsp90 INVOLVING ERK1/2 AND Akt PHOSPHORYLATION IN HUMAN ENDOTHELIAL CELL. Joy, S., Siow, R.C., Rowlands, D.J., Becker, M., Wyatt, A.W., Aaronson, P.I., Coen, C.W., Kallo, I., Jacob, R., Mann, G.E. J. Biol. Chem. (2006) [Pubmed]
  22. 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]
  23. Isoflavone content of infant formulas and the metabolic fate of these phytoestrogens in early life. Setchell, K.D., Zimmer-Nechemias, L., Cai, J., Heubi, J.E. Am. J. Clin. Nutr. (1998) [Pubmed]
  24. Regiospecific hydroxylation of isoflavones by cytochrome p450 81E enzymes from Medicago truncatula. Liu, C.J., Huhman, D., Sumner, L.W., Dixon, R.A. Plant J. (2003) [Pubmed]
  25. Soy isoflavone supplementation in healthy men prevents NF-kappa B activation by TNF-alpha in blood lymphocytes. Davis, J.N., Kucuk, O., Djuric, Z., Sarkar, F.H. Free Radic. Biol. Med. (2001) [Pubmed]
  26. Isoflavones from red clover improve systemic arterial compliance but not plasma lipids in menopausal women. Nestel, P.J., Pomeroy, S., Kay, S., Komesaroff, P., Behrsing, J., Cameron, J.D., West, L. J. Clin. Endocrinol. Metab. (1999) [Pubmed]
  27. Bottlenecks for metabolic engineering of isoflavone glycoconjugates in Arabidopsis. Liu, C.J., Blount, J.W., Steele, C.L., Dixon, R.A. Proc. Natl. Acad. Sci. U.S.A. (2002) [Pubmed]
  28. 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]
  29. Phenoxodiol, a novel isoflavone, induces G1 arrest by specific loss in cyclin-dependent kinase 2 activity by p53-independent induction of p21WAF1/CIP1. Aguero, M.F., Facchinetti, M.M., Sheleg, Z., Senderowicz, A.M. Cancer Res. (2005) [Pubmed]
  30. Low-dose dietary phytoestrogen abrogates tamoxifen-associated mammary tumor prevention. Liu, B., Edgerton, S., Yang, X., Kim, A., Ordonez-Ercan, D., Mason, T., Alvarez, K., McKimmey, C., Liu, N., Thor, A. Cancer Res. (2005) [Pubmed]
  31. Effects of mammalian and plant estrogens on mammary glands and uteri of macaques. Foth, D., Cline, J.M. Am. J. Clin. Nutr. (1998) [Pubmed]
  32. Effects of phytoestrogens genistein and daidzein on prostacyclin production by human endothelial cells. Hermenegildo, C., Oviedo, P.J., García-Pérez, M.A., Tarín, J.J., Cano, A. J. Pharmacol. Exp. Ther. (2005) [Pubmed]
  33. Genistein activates p38 mitogen-activated protein kinase, inactivates ERK1/ERK2 and decreases Cdc25C expression in immortalized human mammary epithelial cells. Frey, R.S., Singletary, K.W. J. Nutr. (2003) [Pubmed]
  34. Effects of high- and low-isoflavone (phytoestrogen) soy foods on inflammatory biomarkers and proinflammatory cytokines in middle-aged men and women. Jenkins, D.J., Kendall, C.W., Connelly, P.W., Jackson, C.J., Parker, T., Faulkner, D., Vidgen, E. Metab. Clin. Exp. (2002) [Pubmed]
  35. 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]
  36. A potential protective mechanism of soya isoflavones against 7,12-dimethylbenz[a]anthracene tumour initiation. Chan, H.Y., Leung, L.K. Br. J. Nutr. (2003) [Pubmed]
  37. Soy isoflavone analysis: quality control and a new internal standard. Song, T., Barua, K., Buseman, G., Murphy, P.A. Am. J. Clin. Nutr. (1998) [Pubmed]
  38. Effects of soy isoflavones on markers of bone turnover in premenopausal and postmenopausal women. Wangen, K.E., Duncan, A.M., Merz-Demlow, B.E., Xu, X., Marcus, R., Phipps, W.R., Kurzer, M.S. J. Clin. Endocrinol. Metab. (2000) [Pubmed]
  39. The effects of phytoestrogen isoflavones on bone density in women: a double-blind, randomized, placebo-controlled trial. Atkinson, C., Compston, J.E., Day, N.E., Dowsett, M., Bingham, S.A. Am. J. Clin. Nutr. (2004) [Pubmed]
  40. Dietary soy containing phytoestrogens does not have detectable estrogenic effects on hepatic protein synthesis in postmenopausal women. Teede, H.J., Dalais, F.S., McGrath, B.P. Am. J. Clin. Nutr. (2004) [Pubmed]
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