Structure and natural occurrence of stereoisomers of the fumonisin B series mycotoxins

Journal of Agricultural and Food Chemistry

Volumn 55, Issue 11, 2007, Pages 4388-4394

  Gelderblom, Wentzel C A ^a,b   Sewram, Vikash ^a   Shephard, Gordon S ^a   Snijman, Petra W ^a   Tenza, Kenny ^c   Van Der Westhuizen, Liana ^a   Vleggaar, Robert ^c  

^a SOUTH AFRICAN MEDICAL RESEARCH COUNCIL   (South Africa)

^b STELLENBOSCH UNIVERSITY   (South Africa)

^c UNIVERSITY OF PRETORIA   (South Africa)

Author keywords

Biosynthesis; Corn; Fumonisins; LC MS; NMR

Indexed keywords

FUMONISIN; FUMONISIN B3; FUMONISIN B4; MYCOTOXIN; UNCLASSIFIED DRUG;

ARTICLE; CHEMISTRY; FUSARIUM; ISOLATION AND PURIFICATION; MAIZE; MICROBIOLOGY; STEREOISOMERISM; TANDEM MASS SPECTROMETRY;

FUMONISINS; FUSARIUM; MYCOTOXINS; STEREOISOMERISM; TANDEM MASS SPECTROMETRY; ZEA MAYS;

ZEA MAYS;

EID: 34250636403     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf070061h     Document Type: Article

References (48)

1. Bezuidenhout, S. C.; Gelderblom, W. C. A.; Gorst-Allman, 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., Chem. Commun. 1988, 743-745.
2. Cawood, M. E.; Gelderblom, W. C. A.; Vleggaar, R.; Behrend, Y.; Thiel, P. G.; Marasas, W. F. O. Isolation of the fumonisin mycotoxins: A quantitative approach. J. Agric. Food Chem. 1991, 39, 1958-1962.
3. Shephard, G. S.; Thiel, P. G.; Stockenström, S.; Sydenham, E. W. Worldwide survey of fumonisin contamination of corn and corn-based products. J. AOAC Int. 1996, 79, 671-687.
4. 1. Onderstepoort J. Vet. Res. 1990, 57, 269-275.
5. Harrison, L. R.; Colvin, B. M.; Green, J. T.; Newman, L. E.; Cole, J. R. Pulmonary edema and hydrothorax in swine produced by fumonisin Bi, a toxic metabolite of Fusarium moniliforme. J. Vet. Diagn. Invest. 1990, 2, 217-221.
6. 1, in rats. Carcinogenesis 1991, 12, 1247-1251.
7. 1 mice. Environ. Health Perspect. 2001, 109, 277-282.
8. Rheeder, J. P.; Marasas, W. F. O.; Thiel, P. G.; Sydenham, E. W.; Shephard, G. S.; Van Schalkwyk, D. J. Fusarium moniforme and fumonisins in corn in relation to human esophageal cancer in Transkei. Phytopathology 1992, 82, 353-357.
9. 1-induced neural tube defects by folic acid. Teratology 2002, 66, 169-176.
10. Hendricks, K. Fumonisins and neural tube defects in south Texas. Epidemiology 1999, 10, 198-200.
11. 1. IARC Monographs on the Evaluation of Carcinogenic Risks to Humans, Some Traditional Medicines, Some Mycotoxins, Naphthalene and Styrene; IARC: Lyon, France, 2002; Vol. 82, pp 301-366.
12. Rheeder, J. P.; Marasas, W. F. O.; Vismer, H. F. Production of fumonisin analogs by Fusarium species. Appl. Environ. Microbiol. 2002, 68, 2101-2105.
13. Food and Drug Administration, 2000; http://vm.cfsan.fda.gov/ %7Edms/fumongui.html.
14. World Health Organization. Evaluation of Certain Mycotoxins in Food; WHO Technical Report Series 906; 56th Report of the Joint FAO/WHO Expert Committee on Food Additives; WHO: Geneva, Switzerland, 2002.
15. 3 in corn: AOAC-IUPAC collaborative study. J. AOAC Int. 1996, 79, 688-696.
16. Gulavita, N. K.; Scheuer, P. J. Two epimeric aliphatic amino alcohols from a sponge, Xestospongia sp. J. Org. Chem. 1989, 54, 366-389.
17. Mori, K.; Matsuda, H. Synthesis of sphingosine relatives. XII. Synthesis and absolute configuration of the two epimeric aliphatic amino alcohols [(5E,7E)-2-amino-5,7-tetra-decadien-3-ols] isolated from a sponge, Xestospongia sp. Liebigs Ann. Chem. 1992, 131-137.
18. Jiménez, C.; Crews, P. Novel marine sponge amino acids, 10. Xestoaminols from Xestospongia sp. J. Nat. Prod. 1990, 53, 978-982.
19. Garrido, L.; Zubía, E.; Ortega, M. J.; Naranjo, S.; Salvá, J. Obscuraminols, new unsaturated amino alcohols from the tunicate Pseudodistoma obscurum: Structure and absolute configuration. Tetrahedron 2001, 57, 4579-4588.
20. Sata, N. U.; Fusetani, N. Amaminols A and B, new bicyclic amino alcohols from an unidentified tunicate of the family Polyclinidae. Tetrahedron Lett. 2000, 41, 489-492.
21. Dale, J. A.; Mosher, H. S. Nuclear magnetic resonance enantiomer reagents. Configurational correlations via nuclear magnetic resonance chemical shifts of diastereomeric mandelate, O- methylmandelate, and α-methoxy-α-trifluoromethylphenylacetate (MTPA) esters. J. Am. Chem. Soc. 1973, 95, 512-519.
22. 19F chemical shifts of α-methoxy-α- trifluoromethylphenylacetate derivatives. J. Org. Chem. 1973, 38, 2143-2147.
23. Ohtani, I.; Kusumi, T.; Kashman, Y.; Kakisawa, H. High-field FT NMR application of Mosher's method. The absolute configurations of marine terpenoids. J. Am. Chem. Soc. 1991, 113, 4092-4096.
24. Jares-Erijman, E. A.; Bapat, C. P.; Lithgow-Bertolloni, A.; Rinehart, K. L.; Sakai, R. Crucigasterins, new polyunsaturated amino alcohols from the Mediterranean tunicate Pseudodistoma crucigaster. J. Org. Chem. 1993, 58, 5732-5737.
25. Kong, F., Faulkner, D. J. Leuettamols A and B, two antimicrobial lipids from the calcareous sponge Leucetta microraphis. J. Org. Chem. 1993, 58, 970-971.
26. Boer, A. Stereochemical studies on the fumonisins, metabolites of Fusarium moniliforme, M.Sc. Dissertation, University of Pretoria, 1992.
27. 1. Tetrahedron Lett. 1994, 35, 7703-7706.
28. 1 at C-2 and C-3. Tetrahedron Lett. 1994, 35, 7707-7710.
29. 1. Tetrahedron Lett. 1995, 36, 1973-1976.
30. 1 backbone. J. Am. Chem. Soc. 1994, 116, 9409-9410.
31. 2 backbone. Tetrahedron Lett. 1994, 35, 6819-6822.
32. Hartl, M.; Humpf, H.-U. Assigning the absolute configuration of fumonisins by the circular dichroism exciton chirality method. Tetrahedron: Asymmetry 1998, 9, 1549-1556.
33. Ward, D. E.; Rhee, C. K. A simple method for the microscale preparation of Mosher's acid chloride. Tetrahedron Lett. 1991, 32, 7165-7166.
34. 1 by Fusarium moniliforme MRC 826 in corn cultures. Appl. Environ. Microbiol. 1993, 59, 2673-2677.
35. 1 by Fusarium moniliforme. Mycopathologia 1993, 124, 99-104.
36. Blackwell, B. A.; Miller, J. D.; Savard, M. E. Production of carbon-14 labelled fumonisin in liquid culture. J. AOAC Int. 1994, 77, 506-511.
37. 1 and related compounds from Fusarium moniliforme. Adv. Exp. Med. Biol. 1996, 392, 75-91.
38. Plattner, R. D.; Shackleford, D. D. Biosynthesis of labeled fumonisins in liquid cultures of Fusarium moniliforme. Mycologia 1992, 117, 17-22.
39. Caldas, E. D.; Sadilkova, K.; Ward, B. L.; Jones, A. D.; Winter, C. K.; Gilchrist, D. G. Biosynthetic studies of fumonisin B1 and AAL toxins. J. Agric. Food Chem. 1998, 46, 4734-4743.
40. Proctor, R. H.; Desjardins, A. E.; Plattner, R. D.; Hohn, T. M. A polyketide synthase gene required for biosynthesis of fumonisin mycotoxins in Gibberella fujikuroi mating population A. Fungal Genet. Biol. 1999, 27, 100-112.
41. Proctor, R. D.; Brown, D. W.; Plattner, R. D.; Desjardins, A. E. Co-expression of 15 contigous genes delineates a fumonisin biosynthetic gene cluster in Gibberella moniliformis. Fungal Genet. Biol. 2003, 38, 237-249.
42. Seo, J. A.; Proctor, R. H.; Plattner, R. D. Characterization of four clustered and coregulated genes associated with fumonisin biosynthesis in Fusarium verticillioides. Fungal Genet. Biol. 2001, 34, 155-165.
43. Butchko, R. A.; Plattner, R. D.; Proctor, R. H. Fum13 encodes a short chain dehydrogenase/reductase required for C-3 carbonyl reduction during fumonisin biosynthesis in Gibberella moniliformis. J. Agric. Food Chem. 2003, 51, 3000-3006.
44. Butchko, R. A.; Plattner, R. D.; Proctor, R. H. FUM9 is required for C-5 hydroxylation of fumonisins and complements the mitotically defined Fum3 locus in Gibberella moniliformis. Appl. Environ. Microbiol. 2003, 69, 6935-6937.
45. Ding, Y.; Bojja, R. S.; Du, L. Fum3p is a 2-ketoglutarate dependent dioxygenase required for C-5 hydroxylation of fumonisins in Fusarium verticillioides. Appl. Environ. Microbiol. 2004, 70, 1931-1934.
46. Bojja, R. S.; Cerny, R. L.; Proctor, R. H.; Du, L. Determining the biosynthetic sequence in the early steps of the fumonisin pathway by use of three gene-disruption mutants of Fusarium verticillioides. J. Agric. Food Chem. 2004, 52, 2855-2860.
47. Yi, H.; Bojja, R. S.; Fu, J.; Du, L. Direct evidence for the function of FUM13 in 3-ketoreduction of mycotoxin fumonisins in Fusarium verticillioides. J. Agric. Food Chem. 2005, 53, 5456-5460.
48. Butchko, R. A.; Plattner, R. D.; Proctor, R. H. Deletion analysis of FUM genes involved in tricarballylic ester formation during fumonisin biosynthesis. J. Agric. Food Chem. 2006, 54, 9398-9404.