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Chemical Compound Review

SureCN33755     (4S)-16,18-dihydroxy-4- methyl-3...

Synonyms: SPBio_000697, KBio3_002986, HMS2233L07, SMP1_000322, AC1L9D25, ...
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Disease relevance of ZEARALENONE


Psychiatry related information on ZEARALENONE


High impact information on ZEARALENONE

  • Precocious sexual development in Puerto Rico and oestrogenic mycotoxins (zearalenone) [4].
  • In this review we report the use of mass spectrometry in connection with chromatographic techniques for mycotoxin determination by considering separately the most diffuse class of mycotoxins: patulin, aflatoxins, ochratoxin A, zearalenone, trichothecenes, and fumonisins [5].
  • The estrogenic effect of zearalenone derivatives was investigated for their binding characteristics to cytosol and nuclear receptors in the uterus [6].
  • In particular, two inhibitors of the plasma membrane proton pump, diethylstilbestrol and zearalenone, had been shown to be stalk cell inducers [7].
  • Antiestrogenic activity of the phytoestrogens could not be detected, except for zearalenone which is a full agonist for ER alpha and a mixed agonist-antagonist for ER beta [8].

Chemical compound and disease context of ZEARALENONE


Biological context of ZEARALENONE


Anatomical context of ZEARALENONE

  • Due to the high sensitivity of these cell lines for zearalenone both test systems are proposed as assays for a quantitative estimation of the biological (estrogenic) activity of this widespread mycotoxin [17].
  • Due to the unavailability of an analytical standard, the ZON-4-O-Glc is not measured in routine analytical procedures, even though it can be converted back to active zearalenone in the digestive tracts of animals [18].
  • The concentration of oestrogen receptor (ER) binding sites after the DMBA treatment was low in the mammary glands of all groups but a significantly higher proportion of the glands in the zearalenone exposed rats were ER-positive (i.e. ER levels > or = 5 fmol mg(-1) protein) than the glands of the vehicle controls [19].
  • 3H- and 14C-labeled zearalenone were found to bind preferentially to one of two peaks containing uncharacterized proteins obtained from the cytosol of young mycelium and resolved by gel column chromatography [20].
  • We have investigated interactions between five mycotoxin species (Trichothecenes, Fumonisins, and Zearalenone) using the DNA synthesis inhibition assay in L929 fibroblasts [21].

Associations of ZEARALENONE with other chemical compounds


Gene context of ZEARALENONE

  • Cdk inhibitory activity in lysates of zearalenone-treated cells was depleted by anti-p27(KIP1) and anti-Cdc2 interacting protein (p21(CIP1)) antibodies [16].
  • Treatment of hPXR-transduced cultured hepatocytes isolated from PXR-knockout mice with zearalenone induces the expression of Cyp3a11, the prototypical murine hepatic PXR-target gene [26].
  • We demonstrated that zearalenone could stimulate the growth of estrogen receptor-positive human breast carcinoma cell line MCF-7 [14].
  • At sub-micromolar concentrations genistein, daidzein, and zearalenone stimulated ERalpha and ERbeta-dependent transcription in Neuro2A cells co-transfected with ERs and simple and complex estrogen-response-element (ERE) containing promoters, although compounds were more active in the presence of ERbeta [27].
  • Cell walls of strains wt292 and mnn9, which have higher levels of beta-D-glucans, were able to complex larger amounts of zearalenone, with higher association constants and higher affinity rates than those of the fks1 and sc1026 strains [28].

Analytical, diagnostic and therapeutic context of ZEARALENONE


  1. Genotoxicity of zearalenone, an estrogenic mycotoxin: DNA adduct formation in female mouse tissues. Pfohl-Leszkowicz, A., Chekir-Ghedira, L., Bacha, H. Carcinogenesis (1995) [Pubmed]
  2. Lack of mutagenicity to Salmonella typhimurium of some Fusarium mycotoxins. Wehner, F.C., Marasas, W.F., Thiel, P.G. Appl. Environ. Microbiol. (1978) [Pubmed]
  3. Mycotoxins and reproduction in domestic livestock. Diekman, M.A., Green, M.L. J. Anim. Sci. (1992) [Pubmed]
  4. Precocious sexual development in Puerto Rico and oestrogenic mycotoxins (zearalenone). Schoental, R. Lancet (1983) [Pubmed]
  5. Recent advances in mycotoxin determination in food and feed by hyphenated chromatographic techniques/mass spectrometry. Sforza, S., Dall'asta, C., Marchelli, R. Mass spectrometry reviews. (2006) [Pubmed]
  6. Binding characteristics of zearalenone analogs to estrogen receptors. Kiang, D.T., Kennedy, B.J., Pathre, S.V., Mirocha, C.J. Cancer Res. (1978) [Pubmed]
  7. Intracellular pH in Dictyostelium: a 31P nuclear magnetic resonance study of its regulation and possible role in controlling cell differentiation. Kay, R.R., Gadian, D.G., Williams, S.R. J. Cell. Sci. (1986) [Pubmed]
  8. Interaction of estrogenic chemicals and phytoestrogens with estrogen receptor beta. Kuiper, G.G., Lemmen, J.G., Carlsson, B., Corton, J.C., Safe, S.H., van der Saag, P.T., van der Burg, B., Gustafsson, J.A. Endocrinology (1998) [Pubmed]
  9. Dietary estrogens stimulate human breast cells to enter the cell cycle. Dees, C., Foster, J.S., Ahamed, S., Wimalasena, J. Environ. Health Perspect. (1997) [Pubmed]
  10. Role of Zearalenone Lactonase in Protection of Gliocladium roseum from Fungitoxic Effects of the Mycotoxin Zearalenone. Utermark, J., Karlovsky, P. Appl. Environ. Microbiol. (2007) [Pubmed]
  11. Ochratoxin A and zearalenone: a comparative study on genotoxic effects and cell death induced in bovine lymphocytes. Lioi, M.B., Santoro, A., Barbieri, R., Salzano, S., Ursini, M.V. Mutat. Res. (2004) [Pubmed]
  12. Toxic effects of mycotoxins in humans. Peraica, M., Radić, B., Lucić, A., Pavlović, M. Bull. World Health Organ. (1999) [Pubmed]
  13. Induction of Hsp 70 in Vero cells in response to mycotoxins Cytoprotection by sub-lethal heat shock and by Vitamin E. El Golli, E., Hassen, W., Bouslimi, A., Bouaziz, C., Ladjimi, M.M., Bacha, H. Toxicol. Lett. (2006) [Pubmed]
  14. Signal transduction through the Ras/Erk pathway is essential for the mycoestrogen zearalenone-induced cell-cycle progression in MCF-7 cells. Ahamed, S., Foster, J.S., Bukovsky, A., Wimalasena, J. Mol. Carcinog. (2001) [Pubmed]
  15. Isolation and characterization of zearalenone sulfate produced by Fusarium spp. Plasencia, J., Mirocha, C.J. Appl. Environ. Microbiol. (1991) [Pubmed]
  16. Removal of Cdk inhibitors through both sequestration and downregulation in zearalenone-treated MCF-7 breast cancer cells. Ahamed, S., Foster, J.S., Bukovsky, A., Diehl, J.A., Wimalasena, J. Mol. Carcinog. (2002) [Pubmed]
  17. Estrogen-controlled gene expression in tissue culture cells by zearalenone. Mayr, U.E. FEBS Lett. (1988) [Pubmed]
  18. Heterologous expression of Arabidopsis UDP-glucosyltransferases in Saccharomyces cerevisiae for production of zearalenone-4-O-glucoside. Poppenberger, B., Berthiller, F., Bachmann, H., Lucyshyn, D., Peterbauer, C., Mitterbauer, R., Schuhmacher, R., Krska, R., Glössl, J., Adam, G. Appl. Environ. Microbiol. (2006) [Pubmed]
  19. Prepubertal exposure to zearalenone or genistein reduces mammary tumorigenesis. Hilakivi-Clarke, L., Onojafe, I., Raygada, M., Cho, E., Skaar, T., Russo, I., Clarke, R. Br. J. Cancer (1999) [Pubmed]
  20. Preferential binding of radiolabeled zearalenone to a protein fraction of Fusarium roseum graminearum. Inaba, T., Mirocha, C.J. Appl. Environ. Microbiol. (1979) [Pubmed]
  21. Statistically designed experiments to screen chemical mixtures for possible interactions. Groten, J.P., Tajima, O., Feron, V.J., Schoen, E.D. Environ. Health Perspect. (1998) [Pubmed]
  22. Metabolism of aflatoxin, ochratoxin, zearalenone, and three trichothecenes by intact rumen fluid, rumen protozoa, and rumen bacteria. Kiessling, K.H., Pettersson, H., Sandholm, K., Olsen, M. Appl. Environ. Microbiol. (1984) [Pubmed]
  23. Incidence of zearalenol (Fusarium mycotoxin) in animal feed. Mirocha, C.J., Schauerhamer, B., Christensen, C.M., Niku-Paavola, M.L., Nummi, M. Appl. Environ. Microbiol. (1979) [Pubmed]
  24. A sensitive zonagenetic assay for rapid in vitro assessment of estrogenic potency of xenobiotics and mycotoxins. Celius, T., Haugen, T.B., Grotmol, T., Walther, B.T. Environ. Health Perspect. (1999) [Pubmed]
  25. Radioimmunoassay for zearalenone and zearalanol in human serum: production, properties, and use of porcine antibodies. Thouvenot, D., Morfin, R.F. Appl. Environ. Microbiol. (1983) [Pubmed]
  26. The mycoestrogen zearalenone induces CYP3A through activation of the pregnane X receptor. Ding, X., Lichti, K., Staudinger, J.L. Toxicol. Sci. (2006) [Pubmed]
  27. Transcriptional regulation by phytoestrogens in neuronal cell lines. Schreihofer, D.A. Mol. Cell. Endocrinol. (2005) [Pubmed]
  28. Adsorption of Zearalenone by beta-D-glucans in the Saccharomyces cerevisiae cell wall. Yiannikouris, A., François, J., Poughon, L., Dussap, C.G., Bertin, G., Jeminet, G., Jouany, J.P. J. Food Prot. (2004) [Pubmed]
  29. Determination of zearalenone in corn by laser fluorimetry. Diebold, G.J., Karny, N., Zare, R.N. Anal. Chem. (1979) [Pubmed]
  30. Indirect enzyme-linked immunosorbent assay for the mycotoxin zearalenone. Liu, M.T., Ram, B.P., Hart, L.P., Pestka, J.J. Appl. Environ. Microbiol. (1985) [Pubmed]
  31. Elaboration of vomitoxin and zearalenone by Fusarium isolates and the biological activity of Fusarium-produced toxins. Vesonder, R.F., Ellis, J.J., Rohwedder, W.K. Appl. Environ. Microbiol. (1981) [Pubmed]
  32. A sensitive and inexpensive yeast bioassay for the mycotoxin zearalenone and other compounds with estrogenic activity. Mitterbauer, R., Weindorfer, H., Safaie, N., Krska, R., Lemmens, M., Ruckenbauer, P., Kuchler, K., Adam, G. Appl. Environ. Microbiol. (2003) [Pubmed]
  33. Relation of 8-ketotrichothecene and zearalenone analog structure to inhibition of mitogen-induced human lymphocyte blastogenesis. Forsell, J.H., Pestka, J.J. Appl. Environ. Microbiol. (1985) [Pubmed]
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