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Biological Reactive Intermediates of Mycotoxins

  • Dennis P. H. Hsieh
Part of the Advances in Experimental Medicine and Biology book series (AEMB, volume 197)

Abstract

Mycotoxins are a variety of highly toxic small molecules produced by many fungi growing in nature or under laboratory conditions. In a handbook compiled by Cole and Cox (1981), more than 200 of these toxic fungal products and their metabolites were described.

Keywords

Cyclohexene Oxide Carcinogenic Potency Schiff Base Formation Molecular Receptor Biochemical Lesion 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

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References

  1. Buchi, G. H., Muller, P. M., Roebuck, B. D., and Wogan, G. N., 1974, Aflatoxin Q1: a major metabolite of aflatoxin B1 produced by human liver, Res. Commun. Chem. Pathol. Pharmacol, 8: 585.PubMedGoogle Scholar
  2. Ch’ih, J. J., Lin T. and Devlin, T. M., 1983, Activation and deactivation of aflatoxin B1 in isolated rat hepatocytes, Biochem. Biophys. Res. Comm, 110: 668.PubMedCrossRefGoogle Scholar
  3. Cole, R. J. and Cox, R. H., 1981, “Handbook of Toxic Fungal Metabolites”, Academic Press, New York.Google Scholar
  4. Coles, B. F., Welch, A. M., Hertzog, P. J., Lindsay Smith, J. R. and Garner, R. C., 1980, Biological and chemical studies on 8,9dihdroxy-8,9-dihydro aflatoxin B1 and some of its esters, Carcinogene, 1: 79.CrossRefGoogle Scholar
  5. Croy, R. G. and Wogan, G. N., 1981a, Temporal patterns of covalent DNA adducts in rat liver after single and multiple doses of aflatoxin B1, Cancer Res, 41: 197.PubMedGoogle Scholar
  6. Croy, R. G. and Wogan, G. N., 1981b, Quantitative comparison of covalent aflatoxin-DNA adducts formed in rat and mouse livers and kidneys, J. Natl. Canc. Inst, 66: 761.Google Scholar
  7. Croy, R. G., Essigman, J. M., Reinhold, V. N. and Wogan, G. N., 1978, Identification of the principal aflatoxin 81-DNA adduct formed in vitro in rat liver, Proc. Natl. Acad. Sci., USA, 75: 1745.PubMedCrossRefGoogle Scholar
  8. Dalezios, J. I., Hsieh, D. P. H. and Wogan, G. N., 1973, Excretion and metabolism of orally administered aflatoxin B1 by rhesus monkeys, Fd Cosmet. Toxicol, 11: 605.CrossRefGoogle Scholar
  9. D’Andrea, A. D. and Haseltine, W. H., 1978, Modification of DNA by AFB1 creates alkali-labile lesions in DNA at positions of guanine and adenine, Proc. Natl. Acad. Sci. USA, 75: 4120.PubMedCrossRefGoogle Scholar
  10. Decad, G. M., Dougherty, K. K., Hsieh, D. P. H. and Byard, J. L., 1979, Metabolism of aflatoxin 81 in cultured mouse hepatocytes: Comparison with rat and effects of cyclohexene oxide and diethyl maleate, Toxicol. Appl. Pharmacol, 50: 429.PubMedCrossRefGoogle Scholar
  11. Degen, G. H. and Neumann, H.-G., 1978, The major metabolite of aflatoxin 81 in the rat is a glutathione conjugate, Chem-Biol. Interact, 22: 239.PubMedCrossRefGoogle Scholar
  12. Degen, G. H. and Neumann, H.-G., 1981, Differences in aflatoxin B1-susceptibility of rat and mouse are correlated with the capability in vitro to inactivate aflatoxin B1-epoxide, Carcinogene, 2: 299.CrossRefGoogle Scholar
  13. Doherty, W. P. and Campbell, T. C., 1972, Inhibition of rat liver mitochondria electron transport flow by aflatoxin 81, Res. Commun. Chem. Pathol. Pharmacol, 3: 601.PubMedGoogle Scholar
  14. Doherty, W. P. and Campbell, T. C., 1973, Aflatoxin inhibition of rat liver mitochondria, Chem-Biol Interact, 7: 63.PubMedCrossRefGoogle Scholar
  15. Edwards, G. S. and Wogan, G. N., 1970, Aflatoxin inhibition of template activity of rat liver chromation, Biochem. Biophys. Acta, 224: 597.PubMedGoogle Scholar
  16. Essigmann, J. M., Croy, R. J., Nadzan, A. M., Busby, W. F., Reinhold, Jr., V. N., Buchi, G. and Wogan, G. N., 1977, Structural identification of the major DNA adduct formed by aflatoxin 81 in vitro, Proc. Natl. Acad. Sci., USA, 74: 1870.PubMedCrossRefGoogle Scholar
  17. Foster, P. L., Eisenstadt, E., and Miller, J. H., 1983, Base substitution mutations induced by metabolically activated AFB1, Proc. Natl. Acad. Sci. U. S., 80: 2695.CrossRefGoogle Scholar
  18. Fukayama, M. Y. and Hsieh, D. P. H. 1984, Effects of butylated hydroxytoluene on the in vitro metabolism, DNA binding and mutagenicity of aflatoxin 81 in the rat, Fd. Chem. Toxicol, 22: 355.CrossRefGoogle Scholar
  19. Green, C. E., Rice, D. W., Hsieh, D. P. H. and Byard, J. L., 1982, The comparative metabolisim and toxic potency of aflatoxin 81 and aflatoxin M1 in primary cultures of adult-rat hepatocytes, Fd. Chem. Toxicol, 20: 53.CrossRefGoogle Scholar
  20. Groopman, J. D., Croy, R. G. and Wogan, G. N., 1981, In vitro reactions of aflatoxin B1-adducted DNA, Proc. Natl. Acad. Sci, USA, 78:5445.PubMedCrossRefGoogle Scholar
  21. Hendricks, J. D., Sinnhuber, R. O., Wales, J. H., Stack, M. E. and Hsieh, D. P. H., 1980a, Carcinogenic response of rainbow trout (Salmo gairdineri) to aflatoxin Q1 and synergistic effect of cyclopropenoid fatty acids, J. Natl. Canc. Inst, 64: 1503.Google Scholar
  22. Hendricks, J. D., Sinnhuber, R. O., Wales, J. H., Stack, M. E., and Hsieh, D. P. H., 1980b, Hepatocarcinogenicity of sterigmatocystin and versicolorin A to rainbow trout (Salmo gairdneri) embryos, J. Natl. Canc. Inst, 64: 1503.Google Scholar
  23. Hsieh, D. P. H., 1979, Basic metabolic effects of Mycotoxins, in: “Interactions of Mycotoxins in Animal Production”, National Academy of Sciences, Washington, D. C.Google Scholar
  24. Hsieh, D. P. H., Dalezios, J. I., Krieger, R. I., Masri, M. S. and Haddon, W. F., 1974, Use of monkey liver microsomes in production of aflatoxin Q1, J. Agric. Fd. Chem, 22: 515.CrossRefGoogle Scholar
  25. Hsieh, D. P. H., Wong, Z. A., Wong, J. J., Michas, C. and Ruebner, B. H., 1977, Comparative metabolism of aflatoxin, in: “Mycotoxins in Human and Animal Health”, J. V. Rodricks, C. W. Hesseltine and M. A. Mehlman, eds., Pathotox, Park Forest South, IL.Google Scholar
  26. Hsieh, D. P. H., Cullen, J. M., and Ruebner, B. H., 1984, Comparative hepatocarcinogenicity of aflatoxins B1 and M1 in the rat, Fd. Chem. Toxicol, 22: 1027.CrossRefGoogle Scholar
  27. Kawabata, Y. Tashiro, F. and Ueno, Y., 1982, Synthesis of a specific protein induced by zearalenone and its derivatives in rat uterus, J. Biochem. (Tokyo), 91: 801.Google Scholar
  28. Kitagawa, M., Tashiro, F. and Ueno. Y., 1982, Interaction between zearalenone, an estrogenic mycotoxin, and the estrogen receptor of the rat brain, Proc. Jpn. Assoc. Mycotoxicol, 15: 28.Google Scholar
  29. Krogh, P., 1977, Ochratoxins, in: “Mycotoxins in Human and Animal Health”, J. V. Rodricks, C. W. Hesseltine and M. A. Mehlman, eds., Pathotox, Park Forest South, IL.Google Scholar
  30. Lin, J., Miller, J. A. and Miller, E. C., 1977, 2,3-Dihydro-2-(guan-7-yl)-3-hydroxy-aflatoxin 81, a major acid hydrolysis product of aflatoxin B1-DNA or ribosomal RNA adducts formed in hepatic microsome-mediated reactions and in rat liver in vivo, Cancer Res, 37: 4430.Google Scholar
  31. Masri, M. S., Haddon, W. F., Lundin, R. E. and Hsieh, D. P. H., 1974, Aflatoxin Q1. A newly identified major metabolite of aflatoxin 81 in monkey liver, J. Agric. Fd. Chem, 22: 512.CrossRefGoogle Scholar
  32. Mirocha, C. J., Pathre, S. V., Christensen, C. M., 1977, Zearalenone, in: “Mycotoxins in Human and Animal Health”, J. V. Rodricks, C. W. Hesseltine and M. A. Mehlman, eds., Pathotox, Park Forest South, IL.Google Scholar
  33. Neal, G. E. and Colley, P. J., 1979, The formation of 2,3-dihydro-2,3dihydroxy aflatoxin 81 by the metabolism of aflatoxin B1 in vitro by rat liver microsomes, FEBS Lett, 101: 382.PubMedCrossRefGoogle Scholar
  34. Newberne, P. M. and Rogers, A. E., 1981, Animal toxicity of major environmental mycotoxins, in: “Mycotoxins and N-Nitroso Compounds: Environmental Risk”, R. C. Shank, ed., CRC Press, Boca Raton, Florida.Google Scholar
  35. Obidoa, O. and Siddiqui, H. T., 1978, Aflatoxin inhibition of avian hepatic mitochondria, Biochem. Pharmacol, 27: 547.PubMedCrossRefGoogle Scholar
  36. Patterson, D. S. P., 1973, Metabolism as a factor in determining the toxic action of the aflatoxins in different animal species, Fd. Cosmet. Toxicol, 11: 287.CrossRefGoogle Scholar
  37. Patterson, D. S. P. and Roberts, B. A., 1971, The in vitro reduction of aflatoxins 81 and B2 by soluble avian liver enzymes, Fd. Cosmet. Toxicol, 9: 829.CrossRefGoogle Scholar
  38. Pier, A. C., Richard, J. L., and Thurston, J. R., 1979, The influences of mycotoxins on resistance and immunity, in: “Interactions of Mycotoxins in Animal Production”, National Academy of Sciences, Washington, D. C.Google Scholar
  39. Pier, A. C., Varman, M. J., and Belden, E. L., 1985, Aflatoxin suppression of cell mediated immune responses and interaction with T-2 toxin, in: “6th International Symposium on Mycotoxins and Phytotoxins”, Abstract, S 27, IUPAC, Pretoria, Republic of South Africa.Google Scholar
  40. Raina, V., Williams, C. J. and Gurtoo, H. L., 1983, Genetic expression of aflatoxin metabolism. Effects of 3-methylcholanthrene and ßnaphtoflavone on hepatic microsomal metabolism and mutagenic activities of aflatoxins, Biochem. Pharmacol, 32: 3755.PubMedCrossRefGoogle Scholar
  41. Rice, D. W. and Hsieh, D. P. H., 1982, Aflatoxin M1: Mn vitro preparation and comparative in vitro metabolism versus aflatoxin 131 in the rat and mouse, Res. Comm. Chem. Path. Pharmacol, 35: 467.Google Scholar
  42. Rodricks, J. V., Hesseltine, C. W., and Mehlman, M. A., 1977, “Mycotoxins in Human and Animal Health”, Pathotox, Park Forest South, Illinois.Google Scholar
  43. Salhab, A. S. and Edwards, G. S., 1977, Comparative in vitro metabolism of aflatoxicol by liver preparations from animals and humans, Cancer Res, 37: 1016.PubMedGoogle Scholar
  44. Salocks, C. B., Hsieh, D. P. H. and Byard, J. L., 1981, Butylated hydroxytoluene pretreatment protects against cytotoxicity and reduces covalent binding of aflatoxin B1 in primary hepatocyte cultures, Toxicol. Apl. Pharmacol, 59: 331.CrossRefGoogle Scholar
  45. Schaaper, R. M., Kunkel, T. A. and Loeb, L. A., 1983, Infidelity of DNA synthesis associated with bypass of apurinic sites, Proc. Natl. Acad. Sci, USA, 80: 487.PubMedCrossRefGoogle Scholar
  46. Stark, A. A., 1980, Mutagenicity and Carcinogenicity of mycotoxins: DNA binding as a possible mode of action, Ann. Rev. Microbiol, 34: 235.CrossRefGoogle Scholar
  47. Stoloff, L., 1977, Aflatoxins-An overview, in: “Mycotoxins in Human and Animal Health”, J. V. Rodricks, C. W. Hesseltine and M. A. Mehlman, eds., Pathotox, Park Forest South, IL.Google Scholar
  48. Stoloff, L., 1980, Aflatoxin M1 in perspective, J. Fd. Prot, 43: 226.Google Scholar
  49. Swenson, D. H., Miller, J. A. and Miller, E. C.,1974, Aflatoxin B1–2,3-oxide: Evidence for its formation in rat liver in vivo and by human liver microsomes in vitro., Biochem. and Biophys., Res. Comm, 60: 1036.Google Scholar
  50. Swenson, D. H., Miller, J. A. and Miller, E. C., 1975, The reactivity and carcinogenicity of aflatoxin B1–2,3-dichloride, a model for the putative 2,3-oxide metabolite of aflatoxin B1, Cancer Res, 35: 3811.PubMedGoogle Scholar
  51. Swenson, D. H., Lin, J., Miller, E. C., and Miller, J. A., 1977, Aflatoxin 2,3-oxide as a probable intermediate in the covalent binding of AFB1 and AFB2 to rat liver DNA and ribosomal RNA in vivo, Cancer Res, 37: 172.PubMedGoogle Scholar
  52. Tashiro, F., Kawabata, Y., Naoi, M. and Ueno, Y., 1980, Zearalenone estrogen receptor interaction and RNA synthesis in rat uterus. in: “Medical Mycology”, H. L. Preusser, ed., Gustav Fisher Verlag, New York.Google Scholar
  53. Tashiro, F., Shihata, A., Nishimura, N. and Ueno, Y., 1983, Zearalenone reductase from rat liver. J. Biochem. (Tokyo), 93: 1557.Google Scholar
  54. Ueno, Y., 1983, “Trichothecenes: Chemical, Biological and Toxicological Aspects”, Elsevier, New York.Google Scholar
  55. Ueno, Y., Ishii, K., Onata, Y., Kamataki, T. and Kato, R., 1983a, Specificity of hepatic cytochrome P-450 isoenzymes from PCB-treated rats and participation of cytochrome b5 in the activation of aflatoxin B1, Carcinogene, 4: 1071.CrossRefGoogle Scholar
  56. Ueno, Y., Tashiro, F. and Kobayashi, T., 1983b, Species difference on zearalenone-reductase activity, Fd. Chem. Toxicol, 21: 167.CrossRefGoogle Scholar
  57. Watson, S. A., Mirocha, C. J. and Hayes, A. W., 1984, Analysis for trichothecenes in samples from Southeast Asia associated with “yellow rain”, Fund. Appl. Toxicol, 4: 700.CrossRefGoogle Scholar
  58. Wells, J. M., Cole, R. J. and Kirskey, J. W., 1975, Emodin, a toxic metabolite of Aspergillus wentii isolated from weevil-damaged chestnuts, Appl. Microbiol, 30: 26.PubMedGoogle Scholar
  59. Wogan, G. N., 1973, Aflatoxin carcinogenesis, in: “Methods in Cancer Research”, H. Busch, ed., Academic Press, New York.Google Scholar
  60. Wong, J. J. and Hsieh, D. P. H., 1976, Mutagenicity of aflatoxins related to their metabolism and carcinogenic potential, Proc. Natl. Acad. Sci, USA, 73: 2241.PubMedCrossRefGoogle Scholar
  61. Wong, J. J., Singh, R. and Hsieh, D. P. H., 1977, Mutagenicity of fungal metabolites related to aflatoxin biosynthesis, Mutat. Res, 44: 447.PubMedCrossRefGoogle Scholar
  62. Wong, Z. A. and Hsieh, D. P. H., 1978, Aflatoxicol: major aflatoxin Almetabolite in rat plasma, Science, 200: 325.PubMedCrossRefGoogle Scholar
  63. Wong, 2. A. and Hsieh, D. P. H., 1980, The comparative toxicokinetics of aflatoxin B1 in the monkey, rat and mouse, Toxicol. Appl . Pharmacol, 55: 115.CrossRefGoogle Scholar
  64. Yoshizawa, H., Uchimaru, R. and Ueno, Y., 1981, Metabolism of aflatoxin B1 in the nuclei isolated from rat liver, J. Biochem., Tokyo, 89: 443.Google Scholar
  65. Yu, F.-L., 1977, Mechanism of aflatoxin B1 inhibition of rat hepatic nuclear RNA synthesis. J. Biol. Chem, 252: 3245.PubMedGoogle Scholar

Copyright information

© Plenum Press, New York 1986

Authors and Affiliations

  • Dennis P. H. Hsieh
    • 1
  1. 1.Department of Environmental ToxicologyUniversity of CaliforniaDavisUSA

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