Biosynthesis of the trichothecene 3-acetyldeoxynivalenol: Cell-free hydroxylations of isotrichodermin

Canadian Journal of Microbiology

Volumn 42, Issue 8, 1996, Pages 828-834

  Zamir, L O ^a,b   Devor, K A ^a   Nikolakakis, A ^a   Sauriol, F ^b  

^a UNIVERSITÉ LAVAL   (Canada)

^b MCGILL UNIVERSITY   (Canada)

Author keywords

15 Deacetylcalonectrin; Cell free system; Fusarium culmorum; Isotrichodermin; Trichothecene

Indexed keywords

3 ACETYLDEOXYNIVALENOL; ISOTRICHODERMIN; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE PHOSPHATE; UNCLASSIFIED DRUG;

ARTICLE; BIOSYNTHESIS; CONTROLLED STUDY; FUSARIUM; HYDROXYLATION; NONHUMAN; PRIORITY JOURNAL;

EID: 0029761309     PISSN: 00084166     EISSN: None     Source Type: Journal    
DOI: 10.1139/m96-104     Document Type: Article

References (21)

1. Anders, M.W., and Mannering, G.J. 1966. Inhibition of drug metabolism. I. Kinetics of the inhibition of the N-demethylation of ethylmorphine by 2-diethylaminoethyl-2,2-diphenylvalerate HCL (SKF-525-A) and related compounds. Mol. Pharmacol. 2: 319-327.
2. Boeynaems, J.M., Demolle, D., and Van Coevorden, A. 1986. Prostacyclinstimulating drugs: new prospects. Prostaglandins, 32: 145-149.
3. Coolbaugh, R.C. Hirano, S.S., and West, C.A. 1978. Studies on the specificity and site of action of a-cyclopropyl-a-[p-thoxyphenyl]-5-pyrimidine methyl alcohol (ancymidol), a plant growth regulator. Plant Physiol. 62: 571-576.
4. Gledhill, L., Hesketh, A.R., Bycroft, B.W., Dewick, P.M., and Gilbert, J. 1991. Biosynthesis of trichothecene mycotoxins: cell-free epoxidation of a trichodiene derivative. FEMS Microbiol. Lett. 81: 241-246.
5. Grasdalen, H., Bäckstrom, D., Eriksson, L.E.G., Ehrenberg, A., Moldeus, P., von Bahr, C., and Orrenius, S. 1975. Heterogeneity of cytochrome P-450 in rat liver microsomes; selective interaction of metyrapone and SKF-525-A with different fractions of microsomal cytrochrome P-450 FEBS Lett. 60: 294-299.
6. Hesketh, A.R., Gledhill, L., Marsh, D.C., Bycroft, B.W., Dewick, P.M., and Gilbert, J. 1990. Isotriochodiol; a post-trichodiene intermediate in the biosynthesis of trichothecene mycotoxins. J. Chem. Soc. Chem. Commun.: 1184-1186.
7. Hohn, T.M., Desjardins, A.E., and McCormick, S.P. 1995. The Tri4 gene of Fusarium sporotrichioides encodes a cytochrome P450 monooxygenase involved in trichothecene biosynthesis. Mol. Gen. Genet. 248: 95-102.
8. Lowry, O.H., Rosebrough, N.J., Fair, A.L., and Randall, R.J. 1951. Protein measurement with the Folin phenol reagent. J. Biol. Chem. 193: 265-275.
9. Omura, T., and Sato, R. 1964. Carbon monoxide-binding pigment of liver microsomes. I. Evidence for its hemoprotein nature. J. Biol. Chem. 239: 2379-2385.
10. Pascal, S., Taton, M., and Rahier, A. 1990. Oxidative C4-demethylation of 24-methylene-cycloartanol by a cyanide-sensitive enzymatic system from higher plant microsomes. Biochem. Biophys. Res. Commun. 172: 98-106.
11. Schellenberg, K.H., and Hellerman, L. 1958. Oxidation of reduced diphosphopyridine nucleotide. J. Biol. Chem. 231: 547-556.
12. Schenkman, J.B., and Cinti, D.L. 1978. Preparation of microsomes with calcium. In Methods in enzymology. Vol. 52. Edited by S. Fleischer and L. Packer. Academic Press, New York. pp. 83-89.
13. 12-desaturase) in microsomal preparations from developing safflower (Carthamus tinctorius L.) cotyledons. Biochem. J. 272: 23-29.
14. VanMiddlesworth, F., Desjardins, A.E., Taylor, S.L., and Plattner, R.D. 1986. Trichodiene accumulation by ancymidol treatment of Gibberella pulcaris. J. Chem. Soc. Chem. Commun.: 1156-1158.
15. Williams, C.H., and Kamin, H. 1962. Microsomal triphosphopyridine nucleotide-cytrochrome c reductase of liver. J. Biol. Chem. 237: 587-595.
16. Zamir, L.O. 1989. Biosynthesis of 3-acetyldeoxynivalenol and sambucinol. Tetrahedron, 45: 227-2305.
17. Zamir, L.O., and Devor, K.A. 1987. Kinetic pulse-labelling study of Fusarium culmorum. Biosynthetic intermediates and dead-end metabolites. J. Biol. Chem. 262: 15 348-15 353.
18. Zamir, L.O., Devor, K.A., Nadeau, Y., and Sauriol, F. 1987. Structure determination and biosynthesis of a novel metabolite of Fusarium culmorum, apotrichodiol. J. Biol. Chem. 262: 15 354-15 358.
19. Zamir, L.O., Devor, K.A., Nikolakakis, A., and Sauriol, F. 1990. Biosynthesis of Fusarium culmorum trichothecenes. The roles of isotrichodermin and 12,13-epoxytrichothec-9-ene. J. Biol. Chem. 265: 6713-6725.
20. Zamir, L.O., Devor, K.A., Morin, N., and Sauriol, F. 1991a. Biosynthesis of trichothecenes: oxygenation steps posi-trichodiene. J. Chem. Soc. Chem. Commun.: 1033-1034.
21. Zamir, L.O., Devor, K.A., and Sauriol, F. 1991b. Biosynthesis of the trichothecene 3-acetyldeoxynivalenol: identification of the oxygenation steps after isotrichodermin. J. Biol. Chem. 266: 14 992-15 000.