The biosynthesis of mycotoxins

Revue de Medecine Veterinaire

Volumn 149, Issue 6, 1998, Pages 469-478

  Steyn, P S ^a  

^a NORTH WEST UNIVERSITY   (South Africa)

Author keywords

Aflatoxin B1; Aflatoxin progenitors; Aurovertin B; Biosynthesis; Citreoviridin; Diplosporin; Fumonisin B1; NMR spectroscopy; Ochratoxin A; Penitrem A; Phomopsin A; Polyketide synthase; PR toxin; Roquefortine; T2; Terpenes; Toxin

Indexed keywords

EID: 0040179570     PISSN: 00351555     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (59)

1. BENNETT J.W., BHATNAGAR D. and CHANG P.K. : The molecular genetics of aflatoxin biosynthesis. In POWELL K.A. et al., eds 1994. The Genus Aspergillus, Plenum Press, New York, 51-58.
2. BENNETT J.W. : From molecular genetics and secondary metabolism to molecular metabolites and secondary genetics. Can. J. Bot., 1994, 73 (Suppl.) l, S914-S924.
3. BEZUIDENHOUT S.C., GELDERBLOM W.C.A., GORST-ALLMAN C.P., HORAK R.M., MARASAS W.F.O., SPITELLER G. and VLEGGAAR R. : Structure elucidation of the fumonisins, mycotoxins from Fusarium moniliforme. J. Chem. Soc., Chem. Commun., 1988, 743-745.
4. BIOLLAZ M., BÜCHI G. and MILNE G. : The biosynthesis of the aflatoxins. J. Am. Chem. Soc., 1970, 92, 1035-1043.
5. BLACKWELL B.A., MILLER J.D. and SAVARD M.E. : Production of carbon-4 labelled fumonisin in liquid culture. J. AOAC International, 1994, 77, 506-511.
6. 1 by Fusarium moniliforme. Myco-pathologia, 1993, 124, 99-104.
7. 1 Can. J. Chem., 1994, 72, 200-207.
8. CARY J.F., WRIGHT M., BHATNAGAR D., LEE R. and CHU F.S. : Molecular characterization of an Aspergillus paraciticus dehydrogenase gene, nor A, located on the aflatoxin biosynthesis gene cluster. Appl. Environ. Microbiol., 1996, 62, 360-366.
9. CHALMERS A.C., GORST-ALLMAN C.P., STEYN P.S., VLEGGAAR R., and SCOTT D.B. : Biosynthesis of diplosporin by Diplodia macrospora. Ring formation involving methionine-derived carbon atoms J. Chem. Soc. Perkin Trans, I, 1979, 1481-1484
10. CHALMERS A.A., DE JESUS A.E., GORST-ALLMAN C.P. and STEYN P.S. : Biosynthesis of PR toxin by Penicillium roqueforti. J. Chem. Soc., Perkin Trans I, 1981, 2899-2903.
11. COLE R.J., DORNER J.W. and HOLBROOK C.C. : Advances in mycotoxin elimination and resistance. In : Advances in Peanut Science. H.E PATTEE and H.T. STALKER (eds.), American Peanut Research and Educational Society, Stillwater, USA, 1995, p. 459.
12. COTTY P.J. : Influence of field applications of an atoxigenic strain of Aspergillus flavus on the populations of Aspergillus flavus infecting cotton balls and on the aflatoxin content of cottonseed. Phytopathology, 1994, 84, 1270-1277.
13. CULVERNOR C.C.J., EDGAR J.A., MACKAY MF, GORST-ALLMAN C.P., MARASAS W.F.O., STEYN P.S., VLEGGAAR R. and WESSELS P.L. : Structure elucidation and absolute configuration of phomopsin A, a hexapeptide mycotoxin produced by Phomopsis leptostromiformis. Tetrahedron, 1989, 45, 2351-2372.
14. DE JESUS A.E., STEYN P.S., VLEGGAAR R. and WESSELS P.L. : Carbon-13 nuclear magnetic resonance assignments and biosynthesis of the mycotoxin ochratoxin A. J. Chem. Soc., Perkin Trans I, 1980, 52-54.
15. DE JESUS A.E., GORST-ALLMAN C.P., STEYN P.S., VAN HEERDEN F.R., VLEGGAAR R., WESSELS P.L. and HULL W.E. : Tremorgenic mycotoxins from Penicillium crustosum. Biosynthesis of penitrem A. J. Chem. Soc., Perkin Trans I., 1983, 1863-1868.
16. DOEHLERT D.C., WICKLOW D.T. and GARDNER H.W. : Evidence implicating the lipoxygenase pathway in building resistance to soybean against Aspergillus flavus. Phytopathology, 1993, 183, 1473-1477.
17. DORNER J.W., COLE R.J., SANDERS T.H. and BLANKENSHIP P.D. : Interrelationship of kernel water activity, soil temperature, maturity and phytoalexin production in preharvest aflatoxin contamination of drought-stressed peanuts. Mycopathologia, 1989, 105, 117-128.
18. DUTTON M.F. : Enzymes and aflatoxin biosynthesis. Microbiol. Rev., 1988, 52, 274-295.
19. FANELLI C. and FABBRI A.A. : Relationship between lipids and aflatoxin biosynthesis. Mycopathologia, 1989, 107, 115-120.
20. FANELLI C., FABBRI A.A., PANFILI G., CASTORIA R., DE LUCA C. and PASSI S. : Aflatoxin congener biosynthesis induced by lipoperoxidation. Exp. Mycology, 1989, 13, 61-68.
21. FARAG R.S., EL-LEITHY M.A., BASYONY A.E. and DAW Z.Y. : Growth and aflatoxin production by Aspergillus parasitus in a medium containing plant hormones, herbicides or insecticides. J. Food Protection, 1987, 50, 1044-1047.
22. GOODRICH-TANRIKULU M., MAHONEY N.E. and RODRIQUES S.B. : The plant growth regulator methyl jasmonate inhibits aflatoxin production by Aspergillus flavus. Microbiology, 1995, 141, 2831-2837.
23. GORST-ALLMAN C.P., STEYN P.S., WESSELS P.L., and SCOTT D.B. : Carbon-13 nuclear magnetic resonance assignments and biosynthesis of versicolorin A in Aspergillus parasiticus. J. Chem. Soc., Perkin Trans. I, 1978, 961-964.
24. 2H N.M.R. spectroscopy. Tetrahedron Letters, 1982, 23, 5359-5362
25. GORST-ALLMAN C.P., STEYN P.S. and VLEGGAAR R. : The biosynthesis of roquefortine. An investigation of acetate and mevalonate incorporation using high field NMR spectroscopy. J. Chem. Soc., Commun., 1982, 652-653.
26. GORST-ALLMAN C.P., STEYN P.S. and VLEGGAAR R. : Biosynthesis of diplosporin by Diplodia macrospora. Part 2. Investigation of ring formation using stable isotopes. J. Chem. Soc., Perkin Trans I., 1983, 1357-1359.
27. GOTO T., WICKLOW D.T., ITO Y. : Aflatoxin and cyclopiazonic acid production by a sclerotium-producing Aspergillus tamarii strain. Appl. Environ. Microbiol., 1996, 62, 4036-4038.
28. HERBERT R.B. : The biosynthesis of secondary metabolites, 231 pages, CHAPMAN & HALL, London, 1989.
29. HOPWOOD D.A. and SHERMAN D.H. : Molecular genetics of polyketides and its comparison to fatty acid biosynthesis. Ann. Rev. Genet., 1990, 24, 37-66.
30. HUTCHISON C.R. and FUJII I. : Polyketide synthase gene manipulation : a structure function approach in engineering novel antibiotics. Ann. Rev. Microbiol., 1995, 49, 201-238.
31. KATE S.P., CARY T.W., BHATNAGAR D., and BENNETT J.W. : Characterization of experimentally induced, non-aflatoxigenic variant strains of Aspergillus parasiticus. Appl. Environ. Microbiol, 1996, 62, 3399-3404.
32. LUCHESE R.H. and HARRIGAN W.F. : Biosynthesis of aflatoxin the role of nutritional factors. J. Appl. Bacterial., 1993, 74, 5-14.
33. MANTLE P.O. and PENN J. : A role for paxilline in the biosynthesis of indole -diterpenoid penitrem mycotoxins. J. Chem. Soc., Perkin Trans. 7, 1989, 1539-1540.
34. PASTER N. : Prevention of aflatoxin formation by natural products. Israel Agreresearch, 1994, 7, 123-131.
35. 1 containing stable isotopes. J. AOAC. Int., 1994, 77, 525-532.
36. REDDY M.J., SHETTY H.S., FANELLI C. and LACEY J. : Role of seed lipids in Aspergillus parasiticus growth and aflatoxin production. J. Sci. Food Agric., 1992, 59, 177-181.
37. SHAPIRA R., PASTER N., EYAL O., MENASHEROV M., METT A. and SALOMON R. : Detection of aflatoxigenic molds in grain by PCR. Appl. Environ. Microbiol. 1996, 62, 3270-3273.
38. 3] acetate into averufin. J. Chem. Soc., Chem. Commun., 1982, 632-634.
39. 1 by Aspergillus flavus. J. Chem. Soc., Chem Commun., 1983, 338-340.
40. STEYN P.S., VLEGGAAR R., WESSELS P.L. and SCOTT D.B. : Biosynthesis of versiconal acetate, versiconol acetate, metabolites from cultures of Aspergillus parasiticus treated with dichlorvos. The role of versiconal acetate in aflatoxin biosynthesis. J. Chem, Soc., Perkin Trans. I, 1979, 460-463.
41. STEYN P.S. : The biosynthesis of mycotoxins : A study in secondary metabolism. P.S. STEYN (ed.), 432 pages, Academic Press, New York, 1980.
42. STEYN P.S., VLEGGAAR R., and WESSELS P.L. : The biosynthesis of aflatoxin and its congeners. Academic Press, New York, 1980, 105-155.
43. 13C n.m.r. study of the biosynthesis of norsolorinic acid. S. Afr. J. Chem., 1981, 34, 12-17.
44. STEYN P.S., VLEGGAAR R. and WESSELS P.L. : Biosynthesis of the aurovertins B and D. The role of methionine and propionate in the simultaneous operation of two independent biosynthetic pathways. J. Chem. Soc., Perkin Trans I, 1981, 1298-1308.
45. STEYN P.S. and VLEGGAAR R., WESSELS P.L. and WOUDENBERG M. : Biosynthesis of citreoviridin. A carbon-13 NMR study. J. Chem. Soc., Perkin Trans I, 1982, 2175-2178.
46. STEYN P.S. and VLEGGAAR R. : Roquefortine, an intermediate in the biosynthesis of oxaline in cultures of Penicillium oxalicum. J. Chem. Soc., Chem. Commun., 1983, 560-561.
47. STEYN P.S. and VLEGGAAR R. : Oxygen-18 labelling studies on the biosynthesis of citreoviridin. J. Chem. Soc., Chem. Commun., 1985, 1531-1532.
48. STEYN P.S. and VLEGGAAR R. : Tremorgenic Mycotoxins. Fortschcrit. Chem. Org. Naturstof., 1985, 48, 1-80.
49. STEYN P.S. and VLEGGAAR R. : Application of biosynthetic techniques in the structural studies of mycotoxins. «Modern Methods in the Analysis and Structural Elucidation of Mycotoxins». Ed. R.J. COLE, Academic Press, 1986, 177-206.
50. TOWNSEND C.A., CHRISTENSEN S.B. and TRAUTWEIN K. : Hexanoate as a starter in polyketide biosynthesis. J. Am. Chem. Soc., 1984, 106, 3868-3869.
51. TOWNSEND C.A. : Progress toward a biosynthetic rationale of the aflatoxin pathway. Pure and Appl. Chem., 1986, 58, 227-238.
52. TOWNSEND C.A., ISOMURA Y., DAVIS S.G. and HODGE J.A. : Reaction models of the oxidative rearrangement of averufin to 1'- hydroxyversicolorone : the first step in dihydrobiofuran formation in aflatoxins biosynthesis. Tetrahedron, 1989, 45, 2263-2276.
53. TOWNSEND C.A., McGUIRE S.M., BROBST S.W., GRAYBILL T.L., PAL K. and BARRY C.E. : Examination of tetrahydro- and dihydrobisfuran formation in aflatoxin biosynthesis : from whole cells to purified enzymes. In Secondary-Metabolite Biosynthesis and Metabolism (PETROSKI R.J. and McCORMICK S.P., eds). 1992, 141-153, Plenum Press, New York.
54. VLEGGAAR R. and STEYN P.S. : The biosynthesis of some miscellaneous mycotoxins. Academic Press, New York, 1980, 395-422.
55. VLEGGAAR R. : Biosynthetic studies on some polyene mycotoxins. Pure Appl. Chem., 1986, 58, 239-256.
56. VLEGGAAR R. : Personal Communication. 1998
57. WANG L.-Y., HATCH M., CHEN C.-J., LEVIN B., YOU S.-L., LU S.-N., WU M.-H., WU W.-P, WANG L.-W., WANG Q., HUANG G.T., YANG P.-M., LEE H.-S. and SANTELLA R.M. : Aflatoxin exposure and risk of hepatocellular carcinoma in Taiwan. Int. J. Cancer., 1996, 76, 620-625.
58. 1. Chem. and Biol., 1996, 3, 463-469.
59. ZAMIR L.O. : Biosynthesis of 3-acetyldeoxynivalenol and sambucinol. Tetrahedron, 1989, 45, 2277-2305.