Skip to main content

Chemistry and Biological Activity of AAL Toxins

  • Chapter
Fumonisins in Food

Part of the book series: Advances in Experimental medicine and Biology ((AEMB,volume 392))

Abstract

AAL toxins and fumonisins comprise a family of highly reactive, chemically related mycotoxins that disrupt cellular homeostasis in both plant and animal tissues. Two critical issues to resolve are the detection of the entire family in food matricies and the mode of cellular disruption. Analysis of the entire set of chemical congeners in food matrices is difficult but has been achieved by a combination of different HPLC and mass spectrometry strategies. The mode of cellular disruption is unknown but likely involves changes associated with the inhibition of ceramide synthase in both plants and animals. Toxin treated cells exhibit morphological and biochemical changes characteristic of apoptosis. Further evaluation of the specific genetic and biochemical changes that occur during toxin-induced cell death may aid in understanding the mole of the action of these mycotoxins.

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

Access this chapter

Chapter
USD 29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 129.00
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 169.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info
Hardcover Book
USD 169.99
Price excludes VAT (USA)
  • Durable hardcover 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

  • Abbas, H.K.; Tanaka, T.; Duke, S.O.; Porter, J.K.; Wray, E.M.; Hodges, L.; Sessions, A.E.; Wang, E.; Merrill, A.H.; Riley, R.T. Fumonisin and AAL-toxin induced disruption of sphingolipid metabolism with accumulation of free sphingoid bases. Plant Physiology 1994, 106, 1085–93.

    CAS  Google Scholar 

  • Abouzied, M.M.; Pestka, J.J. Simultaneous screening of fumonisin FB1 aflatoxin Bb and zearalenone by line immunoblot: A computer-assisted multianalyte assay system. JAOAC International 1994, 77, 495–500.

    CAS  Google Scholar 

  • Azcona-Olivera, J.I.; Abouzied, M.M.; Plattner, R.D.; Norred, W.P.; Pestka, J.J. Generation of antibodies reactive with fumonisins B1, B2, and B3 by using cholera toxin as the carrier-adjuvant. App. Environ. Microbiol. 1992a, 58, 169–173.

    CAS  Google Scholar 

  • Azcona-Olivera, J.I.; Abouzied, M.M.; Plattner, R.D.; Norred, W.P.; Pestka, J.J. Production of monoclonal antibodies to the mycotoxins fumonisins B1 B2, and B3. J. Agric. Food Chem. 1992b, 40, 531–534.

    Article  CAS  Google Scholar 

  • Barr, P.J.; Tornei, L.D. Apoptosis and its role in human disease. Biotechnology 1994, 12, 487–493.

    Article  CAS  Google Scholar 

  • Bezuidenhout, C.S.; Gelderblom, W.C.A.; Gorstallman, C.P.; Horak, R.M.; Marasas, W.F.O.; Spiteller, G.; Vleggaar, R. Structure elucidation of the fumonisins, mycotoxins from Fusarium moniliforme. J. Chem. Soc. Commun. 1988, 743-745.

    Google Scholar 

  • Bottini, A.T.; Bowen, J.R.; Gilchrist, D.G. Phytotoxins. II. Characterization of a phytotoxic fraction from Alternaria alternata f. sp. lycopercici. Tetrahedron Letters 1981, 22, 2723–2726.

    Article  CAS  Google Scholar 

  • Bottini, A.T.; Gilchrist, D.G. Phytotoxins. I. A 1-aminodimethylheptadecapentol from Alternaria alternata f. sp. lycopercici. Tetrahedron Letters 1981, 22, 2719–2722.

    Article  CAS  Google Scholar 

  • Boyle, C.D.; Harmange, J.-C.; Kishi, Y. Novel structure elucidation of AAL toxin TA backbone. J. Am. Chem. Soc. 1994, 775, 4995–4996.

    Article  Google Scholar 

  • Caldas, E.D.; Jones, A.D.; Ward, B.; Winter, C.K.; Gilchrist, D.G. Structural characterization of three new AAL toxins produced by Alternaria alternata f. sp. lycopercici. J. Agric. Food Chem. 1994, 42, 327–333.

    Article  CAS  Google Scholar 

  • Caldas, E.D.; Jones, A.D.; Winter, C.K.; Ward, B.; Gilchrist, D.G. Electrospray ionization mass spectrometry of sphinganine analog mycotoxins. Anal. Chem. 1995, 67, 196–207.

    Article  CAS  Google Scholar 

  • Clouse, S.D.; Gilchrist, D.G. Interaction of the asc locus in F8 paired lines of tomato with Alternaria alternata f. sp. lycopercici and AAL toxin. Phytopathology 1986, 77, 80–82.

    Article  Google Scholar 

  • Gelderblom, W.C.A.; Marasas, W.F.O.; Jaskiewicz, K.; Combrinck, S.; van Schalkwyk, D.J. Cancer promoting otential of different strains of Fusarium moniliforme in a short-term cancer initiation/promotion assay. Carcinogenesis 1988, 9, 1405–1409.

    Article  CAS  Google Scholar 

  • Gerschenson, L. E.; Totello, R. J. Apoptosis: a different type of cell death. The FASEB Journal 1992, 6, 2450–2455.

    CAS  Google Scholar 

  • Gilchrist, D.G; Grogan R.G. Production and nature of a host-specific toxin from Alternaria alternata f. sp. lycopersici. Phytopathology 1976, 66, 165–171.

    Article  Google Scholar 

  • Gilchrist, D.G.; Ward, B.; Moussatos, V.; Mirocha C.J. Genetic and physiological response to fumonisins and AAL-toxin by intact tissue of a higher plant. Mycopathologia 1992, 777, 57–64.

    Article  Google Scholar 

  • Grogan, R.G.; Kimble, K.A.; Misaghi, I. A stem canker disease of tomato caused by, Alternaria alternata f. sp. lycopersici. Phytopathology 1975, 65, 880–886.

    Article  Google Scholar 

  • Lamb, C.J. Plant disease resistance genes in signal perception and transduction Cell 1994, 76, 419–22.

    Article  CAS  Google Scholar 

  • Maragos, C.M.; Richard, J.L. Quantitation and stability of fumonisins B1 and B2 in milk. JAOAC International 1994, 77, 1162–1167.

    CAS  Google Scholar 

  • Marasas, W.F.O.; Kellerman, T.S.; Gelderblom, W.C.A.; Coetzer, J.A.W.; Thiel, P.G.; van der Lugt, J.J. Leukoencephalomacia in a horse induced by fumonisin B1, isolated from Fusarium moniliforme. Onderstepoort J. Vet. Res. 1988a, 55, 197–203.

    CAS  Google Scholar 

  • Marasas, W.F.O.; Jaskiewicz, K.; Venter, F.S.; van Schalkwyk, D.J. Fusarium moniliforme contamination of maize in esophageal cancer areas in Transkei. S. Afr. Med. J. 1988b, 74, 110–114.

    CAS  Google Scholar 

  • Martin, S.J. Apoptosis: suicide, execution or murder? Trends in Cell Biology 1993, 3, 141–144.

    Article  CAS  Google Scholar 

  • Meir, S.; Philosoph-Hadas, S.; Epstein, E.; Aharoni, N. Role of sucrose in the metabolism of IAA-conjugates as related to ethylene production by tobacco leaf discs. In: Ethylene: Biochemical, Physiological and Applied Aspects. Fuchs, Y.; Chalutz, E, eds. Martinus Nijhoff/Dr. W. Junk, publishers, Boston. 1984, pp 97–98.

    Google Scholar 

  • Merrill, A. H.; Wang, E.; Gilchrist, D. G.; Riley, R. T. Fumonisins and other inhibitors of de nova sphingolipid biosynthesis. Advances in Lipid Research 1993, 26, 215–234.

    CAS  Google Scholar 

  • Mirocha, C.J.; Gilchrist, D.G.; Shier, W.T.; Abbas, H.K.; Wen, Y.J.; Vesonder, R.F. AAL toxins, fumonisin (biology and chemistry) and host-specificity concepts. Mycopathologia 1992, 117, 47–56.

    Article  CAS  Google Scholar 

  • Moussatos, V.V.; Witsenboer H.; Hille J.; and Gilchrist D. Behavior of the disease resistance gene Asc in protoplasts of Lycopersicon esculentum Mill. Physiological and Molecular Plant Pathology 1993a, 43, 255–263.

    Article  CAS  Google Scholar 

  • Moussatos, V.V.; Lucas, W.J.; Gilchrist, D.G. AAL-toxin-induced physiological changes in Lycopersicon esculentum Mill: Differential sucrose transport in tomato lines isogenic for the Asc locus. Physiological and Molecular Plant Pathology 1993b, 42, 359–371.

    Article  CAS  Google Scholar 

  • Moussatos, V.V.; Yang, S.F.; Ward, B.W.; Gilchrist, D.G. AAL-toxin induced physiological changes in Lycopersicum esculentum Mill: Roles of ethylene and pyrimidine biosynthesis intermediates in the necrosis response. Physiological and Molecular Plant Pathology 1994, 44, 455–468.

    Article  CAS  Google Scholar 

  • Oikawa, H.; Matsuda, I.; Ichihara, A.; Kohmoto, K. Absolute configuration of C(1)-C(5) fragment of AAL-toxin: Conformationally rigid acyclic aminotriol moiety. Tetrahedron Letters 1994a, 35, 1223–1226.

    Article  CAS  Google Scholar 

  • Oikawa, H.; Matsuda, I.; Kagawa, T.; Ichihara, A.; Kohmoto, K. Absolute configuration of main chain of AAL-toxins. Tetrahedron 1994b, 50, 13347–13368.

    Article  CAS  Google Scholar 

  • Schroeder, J.J.; Crane, H.M.; Xia, J.; Liotta, D.C.; Merrill, A.H. Disruption of sphingolipid metabolism and stimulation of DNA synthesis by fumonisin B1. A molecular mechanism for carcinogenesis associated with Fusarium moniliforme. J. Biol Chem. 1994, 269(5), 3475–81.

    CAS  Google Scholar 

  • Scott, P.M.; Lawrence, G.A. Liquid Chromatographic determination of fumonisins with 4-fluoro-7-nitrobenzofuran. JAOAC International 1992, 75, 829–834.

    CAS  Google Scholar 

  • Shelby, R.A.; Rottinghaus, G.E.; Minor, H.C. Comparison of thin-layer chromatography and competitive immunoassay for detecting fumonisin on maize. J. Agric. Food Chem. 1994, 42, 2064–2067.

    Article  CAS  Google Scholar 

  • Shephard, G.S.; Thiel, P.G.; Marasas, W.F.O.; Sydenham, E.W.; Vleggaar, R. Isolation and determination of the AAL phytotoxins from corn cultures of the fungus Alternaria alternata f. sp. lycopercici. J. Chromatogr. 1993, 641(1), 95–100.

    Article  CAS  Google Scholar 

  • Shier, W.T.; Abbas, H.K.; Badria, F.A. Complete structures of the sphingosine analog mycotoxins fumonisin B1 and AAL toxin TA: Absolute configuration of the side chains. Tetrahedron Letters 1995, 36, 1571–1574.

    Article  CAS  Google Scholar 

  • Siler, D.J.; Gilchrist, D.G. Determination of host-selective phytotoxins from Alternaria alternata f. sp. lycopercici as their maleyl derivatives by high-performance liquid chromatography. J. Chromatogr. 1982, 255, 167–173.

    Google Scholar 

  • Sydenham, E.W.; Thiel, P.G.; Marasas, W.F.O.; Shephard, G.S.; van Schalkwyk, D.J.; Koch, K.R. Natural occurrence of some Fusarium mycotoxins in corn from low and high esophageal cancer prevalence areas of the Transkei southern Africa. J. Agric. Food Chem. 1990, 38, 1900–1903.

    Article  CAS  Google Scholar 

  • Thiel, P.G.; Sydenham, E.W.; Shephard, G.S.; van Schalkwyk, D.J. Study of the reproducibility characteristics of a liquid Chromatographie method for the determination of fumonisins B1 and B2 in corn: IUPAC collaborative study. JAOAC International 1993, 76, 361–366.

    CAS  Google Scholar 

  • Tomei, L.D.; Cope, F.O., eds. Apoptosis: The Molecular Basis of Cell Death. Current Communications in Cell and Molecular Biology. Cold Spring Harbor Laboratory Press. Cold Spring Harbor, NY. 1991, 246 pp.

    Google Scholar 

  • Usleber, E., Straka, M., Terplan, G. Enzyme immunoassay for fumonisin B1 applied to corn-based food. J. Agric. Food Chem. 1994, 42, 1392–96.

    Article  CAS  Google Scholar 

  • Wang, E.; Norred, W.P.; Bacon, C.W.; Riley, R.T.; Merrill, A.H. Inhibition of sphingolipid biosynthesis by fumonisins. J. Biol. Chem. 1990, 266, 14486–90.

    Google Scholar 

  • Wang, E.; Ross, P.E.; Wilson, T.M.; Riley, R.T.; Merrill, A.H. Alteration of serum sphingolipids upon exposure of ponies to feed containing fumonisins, mycotoxins produced by Fusarium moniliforme. J. Nutr. 1992, 122, 1706–16.

    CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Editor information

Editors and Affiliations

Rights and permissions

Reprints and permissions

Copyright information

© 1996 Springer Science+Business Media New York

About this chapter

Cite this chapter

Winter, C.K., Gilchrist, D.G., Dickman, M.B., Jones, C. (1996). Chemistry and Biological Activity of AAL Toxins. In: Jackson, L.S., DeVries, J.W., Bullerman, L.B. (eds) Fumonisins in Food. Advances in Experimental medicine and Biology, vol 392. Springer, Boston, MA. https://doi.org/10.1007/978-1-4899-1379-1_26

Download citation

  • DOI: https://doi.org/10.1007/978-1-4899-1379-1_26

  • Publisher Name: Springer, Boston, MA

  • Print ISBN: 978-1-4899-1381-4

  • Online ISBN: 978-1-4899-1379-1

  • eBook Packages: Springer Book Archive

Publish with us

Policies and ethics