NMR structural studies of fumonisin B1 and related compounds from Fusarium moniliforme

Advances in Experimental Medicine and Biology

Volumn 392, Issue , 1996, Pages 75-91

  Blackwell, B A ^a   Edwards, O E ^b   Fruchier, A ^c   ApSimon, J W ^b   Miller, J D ^a  

^a AGRICULTURE AND AGRI FOOD CANADA   (Canada)

^b CARLETON UNIVERSITY   (Canada)

^c Ecole Normale Superieure de Chimie   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ACETIC ACID; AMINO ACID; CARBON 13; FUMONISIN B1; MYCOTOXIN;

CARBON NUCLEAR MAGNETIC RESONANCE; CONFERENCE PAPER; FUNGUS CULTURE; FUSARIUM MONILIFORME; NONHUMAN; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; TOXIN STRUCTURE; TOXIN SYNTHESIS;

EID: 0029939996     PISSN: 00652598     EISSN: None     Source Type: Book Series    
DOI: 10.1007/978-1-4899-1379-1_7     Document Type: Conference Paper

References (35)

1. 1 by Fusarium moniliforme on rice medium. 106th Annu. Assoc. Off. Anal. Chem. Meeting. Cinncinnati, 1992; p. 234 (Abstr.)
2. ApSimon, J.W.; Blackwell, B.A.; Edwards, O.E.; Fruchier, A.; Miller, J.D.; Savard, M.E.; Young, J.C. The chemistry of fumonisins and related compounds. Fumonisins from Fusarium moniliforme, chemistry, structure and biosynthesis. Pure and Appl. Chem. 1994a, 66, 2315-2318.
3. 1. Tetrahedron Letts. 1994b, 35, 7703-7706.
4. 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 fumonisins, mycotoxins from Fusarium moniliforme. J. Chem. Soc. Chem. Commun. 1988, 743-745.
5. Blackwell, B.A.; Miller, J.D.; Savard, M.E. Production of carbon 14-labelled fumonisin in liquid culture. J. A.O.A.C. International 1994, 77, 506-511.
6. 1. Tetrahedron Letts. 1995, 36, 1973-1976.
7. A backbone. J. Amer. Chem. Soc. 1994, 116, 4995-4996.
8. 2. Tetrahedron Letts. 1995, 36, 4579-4582.
9. 1 by Fusarium moniliforme. Mycopathologia 1993a, 124, 99-104.
10. Branham, B.E.; Plattner, R.D. Isolation and characterization of a new fumonisin from liquid cultures of Fusurium moniliforme. J. Nat. Prod. 1993b, 56, 1630-1633.
11. 2 backbone. Tetrahedron Letts. 1994, 35, 6819-6822.
12. 1 backbone. J. Amer. Chem. Soc. 1994, 116, 9409-9410.
13. 13C do la macrofusine, toxine isolée des mais infesté par Fusarium moniliforme sheld. Analusis 1990, 18, 172-179.
14. Merrill, A.H. Jr.; Wang, E.; Gilchrist, D.G.; Riley, R.T. Fumonisins and other inhibitors of de novo sphingolipid biosynthesis. Adv. Lipid Res. 1993a, 26, 215-234.
15. 1 inhibits sphingosine (sphinganine) N-acyltransferase and de novo sphingolipid biosynthesis in cultured neurons in situ. J. Biol. Chem. 1993b, 268, 27299-27306.
16. Miller, J.D.; Blackwell, B.A. Biosynthesis of 3-acetyldeoxynivalenol and other metabolites by Fusarium culmorum HLX1503 in a stirred jar fermentor. Canadian J. Bot. 1986, 64, 1-5.
17. Miller, J.D.; Savard, M.E.; Rapior, S. Production and purification of fumonisins from a stirred jar fermenter. Natural Toxins 1994, 2, 354-359.
18. Nelson, P.E.; Desjardins, A.E.; Plattner, R.D. Fumonisins, mycotoxins produced by Fusarium species - biology, chemistry and significance. Annu. Rev. Phytopathol. 1993, 31, 233-252.
19. Nelson, P.E.; Dignani, M.E.; Anaissie, E.J. Taxonomy, biology and clinical aspects of Fusarium species. Clinical Microbiol. Rev. 1994, 7(4), 479-504.
20. Norred, W.P. Fumonisins, mycotoxins produced by Fusarium moniliforme. J. Toxic and Environ. Health 1993, 38, 309-328.
21. Ohtani, I.; Kusumi, T; Kashna, Y.; Kakisawa, H. High field FTNMR application of Mosher's method. The absolute configurations of marine terpenoids. J. Amer. Chem. Soc. 1991, 113, 4092-4098.
22. Plattner, R.D.; Shackelford, D.D. Biosynthesis of labelled fumonisins in lipid cultures of Fusarium moniliforme. Mycopathologia 1992, 117, 17-22.
23. Plattner, R.D.; Weislander, D.; Shackelford, D.D.; Peterson, R.; Powel, R.G. A new fumonisin from solid cultures of Fusarium moniliforme. Mycopathologia 1992, 117, 23-28.
24. 1 containing stable isotopes. J. A.O.A.C. International 1994, 77, 525-532.
25. 1 at C-2 and C-3. Tetrahedron Letts. 1994, 35, 7707-7710.
26. Powell, R.G.; Plattner, R.D. Fumonisins, In Alkaloids, Chemical and Biological Perspectives, Vol. 9, S. William Pelletier (Ed.); Pergamon Press: NY, 1995, In Press.
27. 1 in swine. Natural Toxins 1994, 2, 73-80.
28. Riley, R.T.; Wang, E.; Merrill, A.H. Jr. Liquid chromatographic determination of sphinganine and sphingosine: Use of the free sphinganine to sphingosine ratio as a biomarker for consumption of fumonisins. J. A.O.A.C. International 1994a, 77, 533-540.
29. Riley, R.T.; Voss, K.A.; Yool, H.S.; Gelderblom, W.C.A.; Merrill, A.F., Jr. Mechanism of fumonisin toxicity and carcinogenesis. J. Food Protection 1994b, 57, 528-535.
30. Riley, R.T.; Norred, W.P.; Bacon, C.N. Fungal toxins in food - recent concerns. Ann. Rev. Nutrition 1993, 13, 167-189.
31. Savard, M.E.; Blackwell, B.A. Spectral characteristics of secondary metabolites from Fusarium fungi, In Mycotoxins in Grain, Compounds Other Than Aflatoxin, J.D. Miller and H.L. Trenholm (Eds.); Eagan Press: St. Paul, MN, 1994, pp. 59-257.
32. 2 and Alternaria alternata f. sp. lycopersici toxin (AAL) in cultured mammalian cells. Mycopathologia 1991, 116, 97-104.
33. A: Absolute configuration of the side chains. Tetrahedron Letts. 1995, 36, 1571-1574.
34. Van Middlesworth, F.; Dufresne, C.; Wincott, F.F.; Mosley, R.P.; Wilson, K.F. Determination of the relative and absolute stereochemistry of sphingofungins A, B, C, D. Tetrahedron Letts. 1992, 33, 297-300.
35. Wang, E.; Norred, W.P.; Bacon, C.W.; Riley, R.T.; Merrill, A.H., Jr. Inhibition of sphingolipid biosynthesis by fumonisins, implications for diseases associated with Fusarium moniliforme. J. Biol Chem. 1991, 266, 14486-14490.