Abstract
Mycotoxins are a sub-set of the vast array of natural products referred to as secondary metabolites. The evolutionary origin and the role of secondary metabolites for the producing organisms are still areas of vigorous debate but there is a growing concensus that secondary metabolism will benefit the organism and this benefit will usually reflect the nature of the metabolites themselves (Vining, 1992).
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References
Anderegg, R.J., Biemann, K., Büchi, G. and Cushman, M. (1976) Malformin C., a new metabolite of Aspergillus niger. J. Amer. C.em. Soc. 98, 3365–3370.
Assante, G., Merlini, L. and Nasini, G. (1977) (+)-Abscisic acid, a metabolite of the fungus Cercospora rosicola. Experientia 33, 1556–1557.
Beck, J., Ripka, S., Siegner, A., Schütz, E. and Schweize, E. (1990) The multifunctional 6-methyl-salicylic acid synthase gene of Penicillium patulum: its gene structure relative to that of other polyketide synthases. Eur. J. Biochem. 192, 487–498.
Bezuidenhout, S.C., Gelderblom, W.C.A., Gorst-Allman, C.P., Horak, R.M., Marasas, W.F.O., Spiteller, G. and Vleggaar, R. (1988) Structure elucidation of the fumonisins, mycotoxins from Fusarium moniliforme. J. Chem. Soc, Chem. Comm., 743–745.
Birch, A.J. and Donovan, F.W. (1953) Studies in relation to biosynthesis I. Some possible routes to derivatives of orcinol and phloroglucinol. Aust. J. Chem. 6, 360–368.
Birch, A.J. and Hussain, S.F. (1969) Studies in relation to biosynthesis. Part XXXVIII. A preliminary study of fumagillin. J. Chem Soc (C), 1473–1474.
Birch, A.J., Massey-Westrop, R.A. and Moye, C.J. (1955) Studies in relation to biosynthesis VII. 2-hydroxy-6-methyl benzoic acid in Penicillium griseofulvum Dierckx. Aust. J. Chem. 8, 539–544.
Büchi, G., Kitaura, Y., Yuan, S.-S., Wright, H.E., Clardy, J., Demain, A.L., Glinsukar, T., Hunt, N., and Wogan, G.N. (1973) Structure of cytochalasin E, a toxic metabolite of Aspergillus clavatus. J. Amer. Chem. Soc. 95, 5423–5425.
Bu’Lock, J.D. and Ryles, A.P. (1970) The biogenesis of the fungal toxin gliotoxin: the origin of the “extra” hydrogens as established by heavy isotope labelling and mass spectrometry. J. Chem. Soc. Chem. Comm. 1404–1406
Campbell, I.M. (1983) Correlation of secondary metabolism and differentiation, in “Secondary Metabolism and Differentiation in Fungi” (Bennett, J.W. and Ciegler, A., Eds.) pp. 55–72. Marcel Dekker, New York.
Cane, D.E. and Levin, R.H. (1976) Application of Carbon-13 magnetic resonance to isoprenoid biosynthesis. II Ovalicin and the use of doubly labelled mevalonate. J. Amer. Chem. Soc. 98, 1183–1188.
Clardy, J., Springer, J.P., Büchi, G., Matsuo, K. and Wightman, R. (1975). Tryptoquivaline and tryptoquivalone, two tremorgenic metabolites of Aspergillus clavatus. J. Amer. Chem. Soc. 97, 663–665.
Cole, R.J., Dorner, J.W., Springer, J.P. and Cox, R.H. (1981) Indole metabolites from a strain of Aspergillus flavus. J. Agric. Fd. Chem. 29, 293–295.
Cundliffe, E. (1992) Self-protection mechanisms in antibiotic producers, in “Secondary Metabolites: Their Function and Evolution, Ciba Foundation Symposium 171”, (Chadwick, DJ. and Whelan, J.E., Eds.), pp. 198–208. John Wiley, Chichester.
Fennell, D.I. (1977) Aspergillus taxonomy, in “Genetics and Physiology of Aspergillus” (Smith, J.E. and Pateman, J.A., Eds.), pp 1–22. Academic Press, London.
Frisvad, J.C. and Samson, A. (1990) Chemotaxonomy and morphology of Aspergillus fumigatus and related taxa, in “Modem Concepts in Penicillium and Aspergillus Classification” (Samson, R.A. and Pitt, J.I., Eds.) pp 201–208. Plenum Press, New York.
Gallagher, R.T., Clardy, J. and Wilson, B.J. (1980) Aflatrem, a tremorgenic toxin from Aspergillus flavus. Tet. Lett. 21, 239–242.
Gallagher, R.T., Finer, J., Clardy, J., Leutwiler, A., Weibel, F., Acklin, W. and Arigoni, D. (1980) Paspalinine, a tremorgenic metabolite from Claviceps paspali Stevens and Hall. Tet. Lett. 21, 235–238.
Gallagher, R.T., Richard, J.L., Stahr, H.M. and Cole, R.J. (1978) Cyclopiazonic acid production by aflatoxigenic and non-aflatoxigenic strains of Aspergillus flavus. Mycopathologia 66, 31–36.
Gallagher, R.T. and Wilson, B.J. (1978) Aflatrem, the tremorgenic mycotoxin from Aspergillus flavus. Mycopathologia 66, 183–185.
Hamasaki, T., Matsui, K., Isano, K. and Hatsuda, Y. (1973). A new metabolite from Aspergillus versicolor. Agr. Biol. Chem. 37, 1769–1770.
Hopwood, D.A. and Khosha, C. (1992) Genes for polyketide secondary metabolic pathways in microorganisms and plants, in “Secondary Metabolites: Their Function and Evolution, Ciba Foundation Symposium 171”, (Chadwick, D.J. and Whelan, J.E., Eds.), pp. 88–106. John Wiley, Chichester.
de Jesus, A.E., Steyn, P.S., Vleggaar, R., Kirby, G.W., Varley, M.J. and Ferreira, N.P. (1981) Biosynthesis of α-cyclopiazonic acid. Steric course of proton removal during cyclisation of β-cyclopiazonic acid in Penicillium griseofulvum. J. Chem. Soc. Perkin I, 3292–3294.
Keller-Schierlein, W. and Kupfer, E. (1979) Stoffwechselprodukte von Mikroorganismen. Uber die Aspochalasine A, B, C und D. Helv. Chim. Acta 62, 1501–1524.
Kirby, G.W. and Robins, D.J. (1980) The biosynthesis of gliotoxin and related epipolythiodioxo piperazines, in “The Biosynthesis of Mycotoxins: a Study in Secondary Metabolism” (Steyn, P.S., Ed.) pp 301–326. Academic Press, New York.
Kruger, G.J., Steyn, P.S., Vleggaar, R. and Rabie, C.J. (1979) X-ray crystal structure of asteltoxin, a novel mycotoxin from Aspergillus stellatus Curzi. J. Chem. Soc. Chem. Comm. 441–442.
Kurtzman, C.P., Horn, B.W. and Hesseltine, C.W. (1987) Aspergillus nomius, a new aflatoxin-producing species related to Aspergillus flavus and Aspergillus tamarii. Ant. van Leeuwenhoek 53, 147–158.
Ling, K.H., Liou, H.-H., Yang, C.-M. and Yang, C.-K. (1984) Isolation, chemical structure, acute toxicity, and some physicochemical properties of territrem C from Aspergillus terreus. Appl. Environ. Microbiol. 47, 98–100.
Ling, K.-H., Peng, F.-C., Chen, B.J., Wang, Y. and Lee, G.H. (1986) Isolation, physicochemical properties and toxicities of territrems A’ and B’. Saengyak Hakhoechi 17, 153–160.
Ling, K.H., Yang, C.-K. and Peng, F.-T. (1979) Territrems, tremorgenic mycotoxins of Aspergillus terreus. Appl. Environ. Microbiol. 37, 355–357.
McIntyre, C.R. and Simpson, T.J. (1981) Biosynthesis of terretonin, a polyketide-terpenoid metabolite of Aspergillus terreus. J.Chem.Soc. Chem. Comm. 1043–1044.
Moore, R.N., Bigam, G., Chan, J.K., Hogg, A.M., Nakashima, T.T. and Vederas, J.C. (1985) Biosynthesis of the hypocholesterolemic agent mevinolin by Aspergillus terreus. Determination of the origin ofcarbon, hydrogen and oxygen atoms by carbon-13 NMR and mass spectrometry. J. Amer. Chem. Soc. 107, 3694–3671.
Moss, M.O. (1977) Aspergillus mycotoxins, in “Genetics and Physiology of Aspergillus” (Smith, J.E. and Pateman, J.A., Eds.), pp 499–524. Academic Press, London.
Moss, M.O. (1984) The mycelial habit and secondary metabolite production, in “The Ecology and Physiology of the Fungal Mycelium” (Jennings, D.H. and Rayner, A.D.M., Eds.) pp 127–142. C.U.P., Cambridge.
Nozoe, S., Kobayashi, H. and Marisaki, N. (1976) Isolation of β-trans bergamotene from Aspergillus fumigatus, a fumagillin producing fungus. Tet. Lett., 4625–4626.
Peng, F.-C., Ling, K.H., Wang, Y. and Lee, G.-H. (1985) Isolation, chemical structure, acute toxicity, and some physicochemical properties of territrem B’ from Aspergillus terreus. Appl. Environ. Microbiol 49, 721–723.
Rademacher, W. and Graebe, J.E. (1979) Gibberellin A4 produced by Sphaceloma manihoticola, the cause of superelongation disease of cassava. Biochem. Biophys. Res. Comm. 91, 35–40.
Richard, J.L. and Gallagher, R.T. (1979) Multiple toxin production by an isolate of Aspergillus flavus. Mycopathologia 67, 161–163.
Riley, R.T. and Goeger, D.E. (1992) Cyclopiazonic acid: speculation on its function in fungi, in “Mycotoxins in Ecological Systems” (Bhatnagar, D., Lillehoj, E.B. and Arora, D.K., Eds.) pp 385–402. Marcel Dekker, New York.
Simpson, T.J. and Stenzel, D.J. (1981) Biosynthesis of austin, a polyketide-terpenoid metabolite of Aspergillus ustus. J. Chem. Soc. Chem. Comm. 1042–1043.
Steenkamp, D.J., Schabort, J.C. and Ferreira, N.P. (1973) β-cyclopiazonate oxidocyclase from Penicillium cyclopium III Preliminary studies on the mechanism of action. Biochim. et Biophys. acta 309, 440–456.
Tamm, Ch. (1980) The biosynthesis of the cytochalasins, in “The Biosynthesis of Mycotoxins: a Study in Secondary Metabolism” (Steyn, P.S., Ed.) pp 269–299. Academic Press, New York.
Townsend, C.A., Christensen, S.B. and Trautwein, K. (1984) Hexanoate as a starter unit in polyketide biosynthesis. J. Amer. Chem. Soc. 106, 3868–3869.
Turner, W.B. and Aldridge, D.C. (1983) “Fungal metabolites II, ” pp 1–631. Academic Press, London.
Van Middlesworth, F., Dufresne, C., Wincoth, F.E., Mosley, R.T. and Wilson, K.E. (1992b) Determination of the relative and absolute stereochemistry of sphingofungins A, B, C and D. Tet. Lett. 33, 297–300.
Van Middlesworth, F., Giacoble, R.A., Lopez, M., Garrity, G., Bland, J.A., Bartizal, K., Fromtling, R.A., Polshook, J., Zweerink, M., Edison, A.M., Rozdilsky, W., Wilson, K.E. and Monaghan, R.L. (1992a) Sphingofungins A, B, C and D; a new family of antifungal agents 1. Fermentation, isolation and biological activity. J. Antibiot. 45, 861–867.
Vederas, J.C. (1986) Biosynthetic studies on mycotoxins using multiple stable isotope labelling and NMR spectroscopy, in “Mycotoxins and Phycotoxins” (Steyn, P.S. and Vleggaar, R., Eds.) pp 97–108. Elsevier, Amsterdam.
Vining, L.C. (1992) Role of secondary metabolites from microbes, in “Secondary Metabolites: Their Function and Evolution, Ciba Foundation Symposium 171”, (Chadwick, D.J. and Whelan, J.E., Eds.), pp. 184–194. John Wiley, Chichester.
Webster, J. and Lomas, L. (1964) Does Trichoderma viride produce gliotoxin and viridin? Trans. Brit. Mycol. Soc. 47, 535–540.
Wilson, B.J. and Wilson, C.H. (1964) Toxin from Aspergillus flavus: production on food materials of a substance causing tremors in mice. Science 144, 177–178.
Yamazaki, M. (1980) The biosynthesis of neurotropic mycotoxins, in “The Biosynthesis of Mycotoxins: a Study in Secondary Metabolism” (Steyn, P.S., Ed.) pp 193–222. Academic Press, New York.
Zamir, L.O. (1980) The biosynthesis of patulin and penicillic acid, in “The Biosynthesis of Mycotoxins: a Study in Secondary Metabolism” (Steyn, P.S., Ed.) pp 223–268. Academic Press, New York.
Zweerink, M.M., Edison, A.M., Wells, G.B., Pinto, W. and Lester, R.L. (1992) Characterisation of a novel, potent, and specific inhibitor of serine palmitoyltransferase. J. Biol. Chem. 267, 25032–25038.
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Moss, M.O. (1994). Biosynthesis of Aspergillus Toxins — Non-Aflatoxins. In: Powell, K.A., Renwick, A., Peberdy, J.F. (eds) The Genus Aspergillus . Federation of European Microbiological Societies Symposium Series, vol 69. Springer, Boston, MA. https://doi.org/10.1007/978-1-4899-0981-7_2
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