Skip to main content
SpringerLink
Log in

Bisfuranoid Mycotoxins: Their Genotoxicity and Carcinogenicity

  • Chapter
Biological Reactive Intermediates IV

Part of the book series: Advances in Experimental Medicine and Biology ((AEMB,volume 283))

Abstract

Bisfuranoid mycotoxins are a family of fungal metabolites that contain in their molecules a characteristic dihydrobisfuran ring structure. Some representative bisfuranoid mycotoxins are aflatoxins B1, Gl, M1, sterigmatocystin, O- methylsterigmatocystin, and versicolorin A (See Figure 1 & 2).

This is a preview of subscription content, log in via an institution to check access.

Access this chapter

Log in via an institution
eBook
USD 16.99
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 109.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  • Baertschi, S. W., Raney, K. D., Stone, M. P., and Harris, T. M. (1988). Preparation of the 8,9-epoxide of the mycotoxin aflatoxin Bp the ultimate carcinogenic species. J. Am. Chem. Soc. 110, 7929–7931.

    Article  CAS  Google Scholar 

  • Beasley, R. P., and Hwang, L. (1984). Epidemiology of hepatocellular carcinoma. In Viral Hepatitis and Liver Disease ( G. N. Vyas, J. L. Dienstag, and J. H. Hoffnagle, eds.), pp. 209–224. New York: Grune & Stratton.

    Google Scholar 

  • Bechtel, D. H. (1989). Molecular dosimetry of hepatic aflatoxin BI-DNA adducts: linear correlation with hepatic cancer risk. Regul. Toxicol. Pharmacol. 10, 7481.

    Article  Google Scholar 

  • Buss, P. and Lutz, W. K. (1988). Steady-state DNA adduct level in rat liver after chronic exposure to low doses of aflatoxin Bi and 2-acetylaminofluorine. Abstract. Proc. Amer. Assoc. Cancer Res. 29, 380.

    Google Scholar 

  • Cole, R. J., and Cox, R. H. (1981). Handbook of Toxic Fungal Metabolites. New York: Academic Press.

    Google Scholar 

  • Croy, R. G. and Wogan, G. N. (1981). Temporal patterns of covalent DNA adducts in rat liver after single and multiple doses of aflatoxin Bi. Cancer Res. 41, 197–203.

    CAS  PubMed  Google Scholar 

  • Essigmann, J. M., Croy, R. G., Bennett, R. A., and Wogan, G. N. (1982). Metabolic activation of aflatoxin Bi: patterns of DNA adduct formation, removal, and excretions in relation to carcinogenesis. Drug Metab. Rev. 13, 581–602.

    CAS  Google Scholar 

  • Essigmann, J. M., Croy, R. G., Nadzan, A. M., Busby, W. F., Reinhold, V. N., Buchi, G., and Wogan, G. N. (1977). Structural identification of the major DNA adduct formed by aflatoxin Bi in vitro. Proc. Natl. Acad. Sci. USA 74, 1870–1874.

    Article  CAS  Google Scholar 

  • Foster, P. L., Eisenstadt, E., and Miller, J. H. (1983). Base substitution mutations induced by metabolically activated AFB1. Proc. Natl. Acad. USA 80, 2695–2698.

    Article  Google Scholar 

  • Gan, S., Skipper, P. L., Peng, X., Groopman, J. D., Chen, J., Wogan, G. N., and Tannenbaum, S. R. (1988). Serum albumin adducts in the molecular epidemiology of aflatoxin carcinogenesis: correlation with aflatoxin Bi intake and urinary excretion of aflatoxin Mi. Carcinogenesis 9, 1323–1325.

    Article  CAS  PubMed  Google Scholar 

  • Garner, R. C., Dvorackova, I., and Tursi, F. (1988). Immunoassay procedures to detect exposure to aflatoxin Bi and benzo(a)pyrene in animals and man at the DNA level. Int. Arch. Occup. Environ. Health 60, 145–150.

    CAS  Google Scholar 

  • Hendricks J.D., Sinnhuber R.O., Wales J.H., Stack M.E., and Hsieh D.P.H. (1980). Hepatocarcinogenicity of sterigmatocystin and versicolorin A to rainbow trout (Salmo gairdneri) embryos. J. Natl. Cancer Inst. 64, 1503–1509.

    CAS  PubMed  Google Scholar 

  • Hsieh, D. P. H., Wan, C. C., and Billington, J. A. (1989). A versiconal hemiacetal acetate converting enzyme in aflatoxin biosynthesis. Mycopathologia 107, 121–126.

    Article  CAS  PubMed  Google Scholar 

  • 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, Ed.). pp. 37–50. Park Forest South, IL: Pathotox Publishers.

    Google Scholar 

  • Hsieh, L., Hsu, S., Chen, D., and Santella, R. M. (1988). Immunological detection of aflatoxin Bi-DNA adducts formed in vivo. Cancer Res. 48, 6328–6331.

    CAS  Google Scholar 

  • IARC. (1987a). IARC monographs on the evaluation of carcinogenic risks to humans–overall evaluations of carcinogenicity: an updating of IARC Monographs volumes to 42. Suppl. 7, 56–75.

    Google Scholar 

  • IARC. (1987b). IARC monographs on the evaluation of carcinogenic risks to humans–overall evaluations of carcinogenicity: an updating of IARC Monographs volumes 1 to 42. Suppl. 7, 82–87.

    Google Scholar 

  • Irvin, T. R., and Wogan, G. N. (1984). Quantitation of aflatoxin Bi adduction within the ribosomal RNA gene sequences of rat liver DNA. Proc. Natl. Acad. Sci. USA 81, 664–668.

    Article  CAS  PubMed  Google Scholar 

  • Lin, J., Miller, J. A., and Miller, E. C. (1977). 2, 3-Dihydro-2-(guan-7-yl)-3-hydroxyaflatoxin Bi, a major acid hydrolysis product of aflatoxin Bi-DNA or -ribosomal RNA adducts formed in hepatic microsome-mediated reactions and in rat liver in vivo. Cancer Res. 37 4430–4438.

    Google Scholar 

  • Loechler, E. L., Teeter, M. M., and Whitlow, M. D. (1988). Mapping the binding site of aflatoxin Bi in DNA: molecular modeling of the binding sites for the N(7)-guanine adduct of aflatoxin Bi in different DNA sequences. J. Biomol. Struct. Dyn. 5, 1237–1257.

    Article  CAS  PubMed  Google Scholar 

  • Lutz, W. K. (1987). Quantitative evaluation of DNA-binding data in vivo for low-dose extrapolations. Arch. Toxicol. Suppl. 11, 66–74.

    CAS  PubMed  Google Scholar 

  • Martin, C. N., and Garner, R. C. (1977). Aflatoxin B-oxide generated by chemical or enzymic oxidation of aflatoxin Bi causes guanine substitution in nucleic acids. Nature 267, 863–865.

    Article  CAS  PubMed  Google Scholar 

  • Modali, R. and Yang, S. S. (1986). Specificity of aflatoxin Bi binding on human proto-oncogene nucleotide sequence. In Monitoring of Occupational Genotoxicants ( M. Sorsa and H. Norppa, ed.), pp. 147–158. Alan R. Liss.

    Google Scholar 

  • Niranjan, B. G., Bhat, N. K., and Avadhani, N. G. (1982). Preferential attack of mitochondrial DNA by aflatoxin Bi during hepato-carcinogenesis. Science 215, 73–75.

    Article  CAS  PubMed  Google Scholar 

  • Peers, F., Bosch, X., Kaldor, J., Linsell, A., and Pluumen, M. (1987). Aflatoxin exposure, hepatitis B virus infection and liver cancer in Swaziland. Int. J. Cancer 39, 545–553.

    CAS  Google Scholar 

  • Pohland, A. E. and Wood, G. E. (1987). Occurrence of mycotoxins in food. In Mycotoxins in Food ( P. Krogh, ed.), pp. 35–64. London: Academic Press.

    Google Scholar 

  • Reddy, M. B., Irvin, T. R., and Randerath, K. (1985). Formation and persistence of sterigmatocystin-DNA adducts in rat liver determined via 32P-postlabeling analysis. Mutat. Res. 152, 85–96.

    Article  CAS  PubMed  Google Scholar 

  • Sabbioni, G., Skipper, P. L., Buchi, G., and Tannenbaum, S. R. (1987). Isolation and characterization of the major serum albumin adduct formed by aflatoxin Bi in vivo in rats. Carcinogenesis 8, 819–824.

    Article  CAS  PubMed  Google Scholar 

  • 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, 487–491.

    Article  CAS  PubMed  Google Scholar 

  • Shimada, T., and Guengerich, F. P. (1989). Evidence for cytochrome P-45ONF, the nifedipine oxidase, being the principal enzyme involved in the bioactivation of aflatoxins in human liver. Proc. Nat/. Acad. Sci. USA 86, 462–465.

    CAS  Google Scholar 

  • Shimada, T., Nakamura, S., Imaoka, S., and Funae, Y. (1987). Genotoxic and mutagenic activation of aflatoxin Bi by constitutive forms of cytochrome P-450 in rat liver microsomes. Toxicol. Appl. Pharmacol. 91, 13–21.

    Article  CAS  PubMed  Google Scholar 

  • Sun, T. and Chu, Y. (1984). Carcinogenesis and prevention strategy of liver cancer in areas of prevalence. J. Cell Physiol. Supp/. 3, 39–44.

    CAS  Google Scholar 

  • Swenson D.H., Miller J.A., and Miller E.C. (1975). The reactivity and carcinogenicity of aflatoxin Bi-2,3-dichloride, a model for the putative 2,3-oxide metabolite of aflatoxin Bi. Cancer Res. 35, 3811–3823.

    CAS  Google Scholar 

  • Takayama, K., Wakabayashi, K. L., Hsieh, D. P. H., Sugimura, T., and Nagao, M. (1989). Detection of aflatoxin-DNA adducts in liver of humans in Taiwan and Japan. Abstract. The 1989 International Chemical Congress of Pacific Basin Societies, Honolulu, Hawaii, December, 1989.

    Google Scholar 

  • Ueno Y., Ishii K., Omata Y., Kamataki T., and Kato R. (1983). Specificity of hepatic cytochrome P-450 isoenzymes from PCB-treated rats and participation of cytochrome b5 in the activation of aflatoxin Bi. Carcinogenesis 4, 1071–1077.

    Article  CAS  PubMed  Google Scholar 

  • Van Rensburg, S. J., Cook-Mozaffari, P., Van Schakkwyk, D. J., Van Der Watt, J. J., Vincent, T. J., and Purchase, I. F. (1985). Hepatocellular carcinoma and dietary aflatoxin in Mozambique and Transkei. Br. J. Cancer 51, 713–726.

    Article  PubMed  Google Scholar 

  • Wogan, G. N. (1989). Molecular and cellular events associated with aflatoxin-induced hepatocarcinogenesis. Pure Appl. Chem. 61, 1–6.

    Article  CAS  Google Scholar 

  • 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, 2241–2244.

    Article  CAS  PubMed  Google Scholar 

  • Wong J.J., Singh R., and Hsieh D.P.H. (1977). Mutagenicity of fungal metabolites related to aflatoxin biosynthesis. Mutat. Res. 44, 447–450.

    CAS  Google Scholar 

  • Yang, S. S., Taub, J. V., Modsli, R., Vieira, W., Yasei, P., and Yang, G. C. (1985). Dose dependency of aflatoxin Bi binding on human high molecular weight DNA in the activation of Proto-Oncogene. Environ. Health Perspect. 62, 231–238.

    CAS  Google Scholar 

  • Yu, F. (1983). Preferential binding of aflatoxin Bi to the transcriptionally active regions of rat liver nucleolar chromatin in vivo and in vitro. Carcinogenesis 4, 889–893.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Department of Environmental Toxicology, University of California at Davis, Davis, CA, 95616, USA

    Dennis P. H. Hsieh & David N. Atkinson

Authors
  1. Dennis P. H. Hsieh
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. David N. Atkinson
    View author publications

    You can also search for this author in PubMed Google Scholar

Editor information

Editors and Affiliations

  1. Rutgers University, Piscataway, New Jersey, USA

    Charlotte M. Witmer  & Robert R. Snyder  & 

  2. Medical University of South Carolina, Charleston, South Carolina, USA

    David J. Jollow

  3. Thomas Jefferson University, Philadelphia, Pennsylvania, USA

    George F. Kalf  & James J. Kocsis  & 

  4. University of Arizona, Tucson, Arizona, USA

    I. Glenn Sipes

Rights and permissions

Reprints and permissions

Copyright information

© 1991 Plenum Press, New York

About this chapter

Cite this chapter

Hsieh, D.P.H., Atkinson, D.N. (1991). Bisfuranoid Mycotoxins: Their Genotoxicity and Carcinogenicity. In: Witmer, C.M., Snyder, R.R., Jollow, D.J., Kalf, G.F., Kocsis, J.J., Sipes, I.G. (eds) Biological Reactive Intermediates IV. Advances in Experimental Medicine and Biology, vol 283. Springer, Boston, MA. https://doi.org/10.1007/978-1-4684-5877-0_69

Download citation

  • DOI: https://doi.org/10.1007/978-1-4684-5877-0_69

  • Publisher Name: Springer, Boston, MA

  • Print ISBN: 978-1-4684-5879-4

  • Online ISBN: 978-1-4684-5877-0

  • eBook Packages: Springer Book Archive

Publish with us

Policies and ethics

Search

Navigation