Comparison of ceramide synthase inhibitors with other phytotoxins produced by Fusarium species

Journal of Natural Toxins

Volumn 6, Issue 2, 1997, Pages 163-181

  Abbas, H K ^a   Duke, S O ^a   Shier, W T ^b   Badria, F A ^b   Ocamb, C M ^c   Woodward, R P ^c   Xie, W ^b   Mirocha, C J ^b  

^a AGRICULTURAL RESEARCH SERVICE   (United States)

^b UNIVERSITY OF MINNESOTA   (United States)

^c USDA FOREST SERVICE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALTERNARIA; ALTERNARIA ALTERNATA; ANIMALIA; FUSARIUM; LYCOPERSICON ESCULENTUM; MAMMALIA; PREUSSIA AUSTRALIS; SOLANUM NIGRUM;

EID: 0030979821     PISSN: 10588108     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (71)

1. 1 on weed and crop species. Weed Tech. 6, 548-552.
2. Abbas, H. K., and Duke, S. O. (1995). Phytotoxins from plant pathogens as potential herbicides. J. Toxicol. - Toxin Rev. 14, 523-543.
3. Abbas, H. K., and Mirocha, C. J. (1985). Production of moniliformin by Fusarium moniliforme var. subglutinans isolated from wheat kernels originating in Minnesota. Microbiol. Aliment. Natr. 3, 223-227.
4. Abbas, H. K., and Mulrooney, J. E. (1994). Effect of some phytopathogenic fungi and their metabolites on growth of Heliothis virescens (F.) and its host plants. Biocontrol Sci. Tech. 4, 77-87.
5. 1 by Fusarium polyphialidicum collected from seeds of Pinus strobus. Plant Dis. 79, 642.
6. 3 production by Fusarium oxysporum var. redolens. Plant Dis. 78, 968.
7. Abbas, H. K., and Riley, R. T. (1996). The presence and phytotoxicity of the fumonisins and AAL-toxin in Alternaria alternata. Toxicon 34, 133-136.
8. Abbas, H. K., and Vesonder, R. F. (1993). Isolation and purification of AAL-toxin from Alternaria alternata grown on rice. Toxicon 31, 355-358.
9. Abbas, H. K., Boyette, C. P., and Hoagland, R. E. (1995a). Phytotoxicity of Fusarium, other fungal isolates, and of the phytotoxins fumonisin, fusaric acid, and moniliformin to jimsonweed. Phytoprotection 76, 17-25.
10. Abbas, H. K., Boyette, C. P., and Vesonder, R. F. (1993a). Biological control of weeds using AAL-toxin. United States Patent Number 5,256,628; Pate of patent: October 26, 1993, pp. 1-10.
11. Abbas, H. K., Boyette, C. D. Hoagland, R. E., and Vesonder, R. F. (1991). Bioherbicidal potential of Fusarium moniliforme and its phytotoxin, fumonisin. Weed Sci. 39, 673-677.
12. Abbas, H. K., Cartwright, R. P., Shier, W. T., Johnson, B. J. Sciumbato, G. L., and Krick, T. (1996a). The natural occurrence of fumonisins in rice infected with Fusarium sheath rot disease. Phytopathology 86, 42.
13. 1. Phytopathology 86, 26.
14. Abbas, H. K., Duke, S. O., Shier, W. T., Riley, R. T., and Kraus, G. A. (1996c). The chemistry and biological activities of the natural products AAL-toxin and the fumonisins. In: Natural Toxins II, B. R. Singh and A. T. Tu (Eds.), Chapter 23, pp. 293-308. Plenum Press, New York.
15. 1 on tomato cultivars. J. Phytopath. 143, 329-334.
16. Abbas, H. K., Tanaka, T., Duke, S. O., and Boyette, C. D. (1995c). Susceptibility of various crop and weed species to AAL-toxin, a natural herbicide. Weed Technol. 9, 125-130.
17. Abbas, H. K., Tanaka, T., Duke, S. O., Porter, J. K., Wray, E. M., Hodges, L., Sessions, A. E., Wang, E., Merrill, Jr., A. H., and Riley, R. T. (1994). Fumonisin- and AAL-toxin-induced disruption of sphingolipid metabolism with accumulation of free sphingoid bases. Plant Physiol. 106, 1085-1093.
18. Abbas, H. K., Tanaka, T., and Shier, W. T. (1995d). Biological activities of synthetic analogs of Alternaria alternata AAL-toxin and fumonisin in plants and mammalian cell cultures. Phytochemistry 6, 1681-1589.
19. Abbas, H. K., Vesonder, R. F., Boyette, C. D., Hoagland, R. F., and Krick, T. (1992). Production of fumonisins by Fusarium moniliforme cultures isolated from jimsonweed in Mississippi. J. Phytopath. 136, 199-203.
20. Abbas, H. K., Vesonder, R. F., Boyette, C. D., and Peterson, S. W. (1993b). Phytotoxicity of AAL-toxin and other compounds produced by Alternaria alternata to jimsonweed (Datura stramonium). Can. J. Bot. 71, 155-160.
21. Allen, N. K., Burmeister, H. R., Weaver, G. A., and Mirocha, C. J. (1981). Toxicity of dietary and intravenously administered moniliformin to broiler chickens. Poultry Sci. 60, 1415-1417.
22. Bottini, A. T., and Gilchrist, D. G. (1981). Phytotoxins I. A. 1-aminodimethylhepta-decapentol from Alternaria alternata f. sp. lycopersici. Tetrahedron Lett. 22, 2719-2722.
23. 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. Commun. 1984, 743-745.
24. Borrow, A., Brian, P. W., Chester, V. E., Curtis, P. J., Hemming, H. G., Henehan, C., Jeffreys, E. G., Lloyd, P. B., Nixon, I. S., Noris, G. L. F., and Radley, M. (1955). Gibberellic acid, a metabolic product of the fungus Gibberella fujikuroi: Some observations on its production and isolation. J. Sci. Food Agric. 6, 340-348.
25. Bottini, A. T., Bowen, J. R., and Gilchrist, D. G. (1981). Phytotoxins II. Characterization of a phytotoxic fraction from Altemaria alternata f. SP. lycopersici. Tetrahedron Lett. 22, 2723-2726.
26. Brian, P. W., Elson, G. W., Hemming, H. G., and Radley, M. (1954). The plant-growth promoting properties of gibberellic acid, a metabolic product of the fungus Gibberella fujikuroi. J. Sci. Food Agric. 5, 602-612.
27. Burmeister, H. R., Grove, M. D., and Kwolek, W. F. (1980). Moniliformin and butenolide: Effect on mice of high-level, long-term oral intake. Appl. Environ. Microbiol. 40, 1142-1144.
28. Caldas, E. D., Jones, A. D., Ward, B., Winter, C., and Gilchrist, D. G., Jr. (1994). Structural characterization of three new AAL-toxins produced by Altemaria alternata f. sp. lycopersici. J. Agric. Food Chem. 42, 327-333.
29. Chen, J. (1996). Identification and characterization of fumonisin and AAL toxins and their derivatives produced by Fusarium moniliforme and Altemaria alternata f.sp. lycopersici. Ph.D. Thesis, Department of Plant Pathology, University of Minnesota, St. Paul, Minnesota 55108.
30. 1 by Altemaria alternata f. sp. lycopersici. Appl. Environ. Microbiol. 58, 3928-3931.
31. 6 paired lines of tomato wilt Alternaria alternata f. sp. lycopersici and AAL-toxin. Phytopathology 77, 80-82.
32. Cole, R. J., Kirksey, J. W., Cutler, H. G., Doupnik, B. L., and Peckham, J. C. (1973). Toxin from Fusarium moniliforme: effects on plants and animals. Science 179, 1324-1326.
33. Davis, D. (1969). Fusaric acid in selective pathogenicity of Fusarium oxysporum. Phytopathology 59, 1391-1395.
34. Duke, S. O., and Abbas, H. K. (1995). Natural products with use as herbicides. In: Allelopathy, Organisms, Processes, and Applications, Interjit, K. M. M. Dakshini, and F. A. Einhellig (Eds.). Am. Chem. Soc. Symp. Ser. No. 582, Chapter 25, pp. 348-362. ACS Books, Washington, DC
35. Duke, S. O., Abbas, H. K., Boyette, C. D., and Gohbara, M. (1990). Microbial compounds with the potential for herbicidal use. Proc. Brighton Crop Prot. Conf. - Weeds 3b-2, 155-164.
36. Duke, S. O., Gohbara, M., Paul, R. N., and Duke, M. V. (1992). Colletotrichin causes rapid membrane damage to plants. J. Phytopath. 134, 289-305.
37. Duke, S. O., Paul, R. N., and Wickliff, J. L. (1980). Tentoxin effects on ultrastructure and greening of ivyleaf morningglory Ipomoea hederacea (L.) var. hederacea cotyledons. Physiol. Plant 49, 27-36.
38. Durbin, R. D. (Ed.) (1981). Toxin in Plant Disease. Physiological Ecology Series. Academic Press, a subsidiary of Harcourt Brace Jovanovich, Publishers. 515 pp.
39. Gelderblom, W. C. A., Jaskiewicz, K., Marasas, W. F. O., Theil, P.G., Horak, R. M., Vleggaar, R., and Kreik, N. P. (1988). Fumonisins-novel mycotoxins with cancer-promoting activity produced by Fusarium moniliforme. Appl. Environ. Microbiol. 54, 1806-1811.
40. Gloer, J. B. (1995). The chemistry of fungal antagonism and defense. Can. J. Bot. 73, S1265-S1274.
41. 1, a toxic metabolite of Fusarium moniliforme. J. Vet. Diagn. Invest. 2, 217-221.
42. Hensens, O. D., Helms, G. L., Turner Jones, E. T., and Harris, G. H. (1995). Structure elucidation of australifungin, a potent inhibitor of spinganine N-acyltransferase in sphingolipid biosynthesis from Sporormiella australis. J. Org. Chem. 60, 1772-1776.
43. Hoagland, R. E. (Ed.) (1990). Microbes and microbial products as herbicides. Am. Chem. Soc. Symp. Ser. No. 439. ACS Books, Washington, DC. 347 pp.
44. Koerner, T. A. W., Jr., Voll, R. J., and Younathan, E. S. (1977). Isolation of 2,5-anhydro-1,3-O-isopropylidene-6-O-trityl-D-glucitol and conformations of its 4-O-substituted and deprotected, acetylated derivatives. Carbohydrate Res. 59, 403-416.
45. Kuo, M. S., and Scheffer, R. P. (1964). Evaluation of fusaric acid as a factor in development of Fusarium wilt. Phytopathology 54, 1041-1044.
46. Mandala, S. M., Thornton, R. A., Frommer, B. R., Curotto, J. E., Rozdilsky, W., Kurtz, M. B., Giacobbe, R. A., Bills, G. F., Cabello, M. A., Martin, I., Pelaez, F., and Harris, G. H. (1995). The discovery of australifungin, a novel inhibitor of sphinganine N-acyltransferase from Sporormiella australis, producing organism, fermentation, isolation, and biological activity. J. Antibiotics 48, 349-356.
47. 1 isolated from Fusarium moniliforme. Onderstepoort. J. Vet. Res. 55, 197-203.
48. Merrill, A. H. (1992). Ceramide: A new lipid "second messenger"? Nutrition Rev. 50, 78-80.
49. Mirocha, C. J., Gilchrist, G. D., Shier, W. T., Abbas, H. K., Wen, Y., and Vesonder, R. F. (1992). AAL-toxins, fumonisins (biology and chemistry) and host-specificity concepts. Mycopathologia 117, 47-56.
50. Mirocha, C. J., Chen, J., Xie, W., Xu, Y., Abbas, H. K., and Hogge, L. H. (1996). Biosynthesis of fumonisin and AAL derivatives by Alternaria and Fusarium in laboratory culture. In: Fumonisin in Food, L. S. Jackson, J. W. DeVries, and L. B. Bullerman (Eds.), Vol. 19, pp. 213-224. Plenum Press, New York.
51. 1 production by Fusarium species other than F. moniliforme in section Liseola and by some related species. Appl. Environ. Microbiol. 58, 984-989.
52. Nelson, P. E., Toussoun, T. A., and Marasas, W. F. O. (1983). Fusarium Species: An Illustrated Guide for Identification. The Pennsylvania State University Press, University Park, Pennsylvania, USA. 193 pp.
53. Nishimura, S., and Kohmoto, K. (1993). Host-specific toxins and chemical structures from Alternaria species. Annu. Rev. Phytopathol. 21, 87-116.
54. Norred, W. P. (1993). Fumonisins-mycotoxins produced by Fusarium moniliforme. J. Toxicol. Environ. Health 38, 309-328.
55. Ocamb, C. M., and Juzwik, J. (1995). Fusarium species isolated from diseased roots and soil of eastern white pine nursery seedlings. Can. J. Plant Pathol. 17, 325-330.
56. Ocamb, C. M., and Kommedahl, T. (1994). Growth of rhizosphere competent and incompetent Fusarium species from corn on carbon substrates. Phytopathology 84, 508-514.
57. Porter, J. K., Bacon, C. W., Wray, E. M., and Hagler, W. M., Jr. (1995). Fusaric acid in Fusarium moniliforme cultures, corn, and feeds toxic to livestock and the neurochemical effects in the brain and pineal gland of rats. Natural Toxins 3, 91-100.
58. Riley, R. T., Wang, E., Schroeder, J. J., Smith, E. R., Plattner, R. D., Abbas, H. K., Yoo, H-S, and Merrill, A. H., Jr. (1996). Evidence for disruption of sphingolipid metabolism as a contributing factor in the toxicity and carcinogenicity of fumonisins. Natural Toxins 4, 3-15.
59. Shamil, S., and Birch, G. G. (1989). Structural functions of taste in 5-membered ring structures. Food Chem. 32, 171-188.
60. Shier, W. T. (1992). Sphingosine analogues: An emerging new class of toxins that includes the fumonisins. J. Toxicol. - Toxin Rev. 11, 141-257.
61. Siler, D. J., and Gilchrist, D. G. (1983). Properties of host specific toxins produced by Alternaria alternata f. sp. lycopersici in culture and in tomato plants. Physiological Plant Pathology 23, 265-274.
62. Smith, T. K., and Sousadias, G. (1993). Fusaric acid content of swine feedstuffs. J. Agric. Food Chem. 41, 2296-2298.
63. Tanaka, T., Abbas, H. K., and Duke, S. O. (1993). Structure-dependent phytotoxicity of fumonisins, and related compound in a duckweed bioassay. Phytochemistry 33, 779-785.
64. Tanaka, T., Hatano, K., Watanabe, M., and Abbas, H. K. (1996). Isolation, purification of 2,5-anhydro-D-glucitol as a phytotoxin from Fusarium solani. J. Natural Tox. (in press).
65. Thalmann, A., Matzenauer, S., and Gruber-Schley, S. (1985). Survey on the occurrence of fusariotoxins in cereals. Ber. Landwirtsch. 63, 257-272 (in German).
66. Thiel, P. G., Marasas, W. F. O., Sydenham, E. W., Shephard, G. S., Gelderblom, W. C. A., and Nieuwenhuis, J. J. (1991). Survey of fumonisin production by Fusarium species. Appl. Environ. Microbiol. 57, 1089-1093.
67. Thiel, P. G., Marasas, W. F. O., Sydenham, E. W., Shephard, G. S., and Gelderblom, W. C. A. (1992). The implications of naturally occurring levels of fumonisins for human and health. Mycpathologia 117, 3-9.
68. Thiel, P. G., Meyer, C. J., and Marasas, W. F. O. (1982). Natural occurrence of moniliformin together with deoxynivalenol and zearalenone in Transkeian corn. J. Agric. Food Chem. 30, 308-312.
69. 1: Isolation from corn culture, and purification by high performance liquid chromatography. Mycotoxin Res. 6, 85-88.
70. Wang, E., Norred, W. P., Bacon, C. W., Riley, R. T., and Merrill, Jr., A. H. (1991). Inhibition of sphingolipid biosynthesis by fumonisins. J. Biol. Chem. 266, 14486-14490.
71. Windels, C. E., Burnes, P. M., and Kommedahl, T. (1988). Five-year preservation of Fusarium species on silica gel and soil. Phytopathology 78, 107-109.