Inhibition of the acyl-CoA desaturases involved in the biosynthesis of Spodoptera littoralis sex pheromone by analogs of 10,11-methylene-10- tetradecenoic acid

Insect Biochemistry and Molecular Biology

Volumn 34, Issue 3, 2004, Pages 283-289

  Rodríguez, Sergio ^a   Camps, Francisco ^a   Fabriàs, Gemma ^a  

^a DEPARTMENT OF ENVIRONMENTAL CHEMISTRY   (Spain)

Author keywords

Biosynthesis; Cyclopropene fatty acid; Cyclopropenol; Desaturase; Lepidoptera; Sex pheromone

Indexed keywords

LEPIDOPTERA; SPODOPTERA LITTORALIS;

EID: 1242344709     PISSN: 09651748     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.ibmb.2003.11.003     Document Type: Article

References (20)

1. Al-Dulayymi J.R., Baird M.S., Simpson M.J., Nyman S. Structure based interference with insect behaviour. Cyclopropene analogues of pheromones containing Z-alkenes. Tetrahedron. 52:1996;12509-12520.
2. Allen E., Johnson A.R., Fogerty A.C., Pearson J.A., Shenstone F.S. Inhibition by cyclopropene fatty acids of the desaturation of stearic acid in hen liver. Lipids. 2:1967;419-423.
3. Ando T., Ohno R., Ikemoto K., Yajima Y. Cyclopropene fatty acid and amide: inhibitors of the sex pheromone biosynthesis in Bombyx mori. J. Pesticide Sci. 20:1995;25-32.
4. Ando T., Ikemoto K., Ohno R., Yamamoto M. Stereochemistry of delta 11-desaturation and inhibitors of delta 10,12-desaturation in the biosynthesis of bombykol, sex pheromone of the female silkworm moth, examined with deuterated precursors. Arch. Insect Biochem. Physiol. 37:1998;8-16.
5. Arsequell G., Fabriàs G., Camps F. Inhibition of a delta-11 desaturase in Spodoptera littoralis by 12,13-methylenehexadec-12-enoic acid. Insect Biochem. 19:1989;623-627.
6. Cao J., Blond J.P., Bézard J. Inhibition of fatty acid delta-6 and delta-5 desaturation by cyclopropene fatty acids in rat liver microsomes. Biochim. Biophys. Acta. 1210:1993;27-34.
7. Clark J.R., Kircher H.W. Synthesis and biological characterization of 10,11-methylene-9-nonadecene; an analog of sterculic acid. Lipids. 7:1972;769-772.
8. Fabriàs G., Barrot M., Camps F. Control of the sex pheromone biosynthetic pathway in Thaumetopoea pityocampa by the pheromone biosynthesis activating neuropeptide. Insect Biochem. Molec. Biol. 25:1995;655-660.
9. Fabriàs G., Gosalbo L., Quintana J., Camps F. Direct inhibition of (Z)-9 desaturation of (E)-11-tetradecenoic acid by methylenehexadecenoic acids in the biosynthesis of Spodoptera littoralis sex pheromone. J. Lipid Res. 37:1996;1503-1509.
10. Fogerty A.C., Johnson A.R., Pearson J.A. Ring position in cyclopropene fatty acids and stearic acid desaturation in hen liver. Lipids. 7:1972;335-338.
11. Gosalbo L., Fabriàs G., Arsequell G., Camps F. Inhibition of sex pheromone biosynthesis in Spodoptera littoralis by cyclopropene fatty acids. Insect Biochem. Molec. Biol. 22:1992;687-690.
12. Gosalbo L., Fabriàs G., Camps F. Inhibitory effect of 10,11-methylenetetradec-10-enoic acid on a Z9-desaturase in the sex pheromone biosynthesis of Spodoptera littoralis. Arch. Insect Biochem. Physiol. 26:1994;279-286.
13. Jeffcoat R., Pollard M.R. Studies on the inhibition of the desaturases by cyclopropenoid fatty acids. Lipids. 12:1977;480-485.
14. Johnson A.R., Pearson J.A., Shenstone F.S., Fogerty A.C. Inhibition of the desaturation of stearic to oleic acid by cyclopropene fatty acids. Nature. 214:1967;1244-1245.
15. Nordby H.E., Heywang B.W., Kircher H.W., Kemmerer A.R. Sterculic derivatives and pink egg formation. J. Am. Oil Chem. Soc. 39:1962;183-185.
16. Ory R.L., Altschul A.M. Cyclopropenyl compounds as sulfhydryl reagents. Biochem. Biophys. Res. Commun. 17:1964;12-16.
17. Quintana J., Barrot M., Fabriàs G., Camps F. A model study on the mechanism of inhibition of fatty acyl desaturases by cyclopropene fatty acids. Tetrahedron. 54:1998;10187-10198.
18. Raju P.K., Reiser R. Inhibition of fatty acyl desaturase by cyclopropene fatty acids. J. Biol. Chem. 242:1967;379-384.
19. Reiser R., Raju P.K. The inhibition of saturated fatty acid dehydrogenation of dietary fat containing sterculic and malvalic acids. Biochem. Biophys. Res. Commun. 17:1964;8-11.
20. Salaün J., Baird M.S. Biologically active cyclopropanes and cyclopropenes. Curr. Med. Chem. 2:1995;511-542.