Expression and evolution of Δ 9 and Δ 11 desaturase genes in the moth Spodoptera littoralis

Insect Biochemistry and Molecular Biology

Volumn 34, Issue 12, 2004, Pages 1315-1328

  Rodríguez, Sergio ^a   Hao, Guixia ^b   Liu, Weitian ^b   Piña, Benjamín ^c   Rooney, Alejandro P ^d   Camps, Francisco ^a   Roelofs, Wendell L ^b   Fabriàs, Gemma ^a  

^a DEPARTMENT OF ENVIRONMENTAL CHEMISTRY   (Spain)

^b Department of Molecular Biology and Genetics   (United States)

^c INSTITUT DE BIOLOGIA MOLECULAR DE BARCELONA   (Spain)

^d NATIONAL CENTER FOR AGRICULTURAL UTILIZATION RESEARCH   (United States)

Author keywords

cDNA; Cloning; Desaturase; Fatty acid; Pheromone; Unsaturation

Indexed keywords

LEPIDOPTERA; MYTHIMNA UNIPUNCTA; SPODOPTERA LITTORALIS;

ACYL COENZYME A DESATURASE; COMPLEMENTARY DNA; FATTY ACID; RECOMBINANT PROTEIN; SEX PHEROMONE;

AMINO ACID SEQUENCE; ANIMAL; ARMYWORM; ARTICLE; BIOSYNTHESIS; ENZYMOLOGY; FAT BODY; GENETICS; METABOLISM; MOLECULAR CLONING; MOLECULAR EVOLUTION; MOLECULAR GENETICS;

AMINO ACID SEQUENCE; ANIMALS; CLONING, MOLECULAR; DNA, COMPLEMENTARY; EVOLUTION, MOLECULAR; FAT BODY; FATTY ACID DESATURASES; FATTY ACIDS; MOLECULAR SEQUENCE DATA; RECOMBINANT PROTEINS; SEX ATTRACTANTS; SPODOPTERA; STEAROYL-COA DESATURASE;

EID: 8644261002     PISSN: 09651748     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.ibmb.2004.09.003     Document Type: Article

References (56)

1. J.L. Abad, F. Camps, and G. Fabrias Is hydrogen tunneling involved in acylCoA desaturase reactions? The case of a delta(9) desaturase that transforms (E)-11-tetradecenoic acid into (Z,E)-9,11-tetradecadienoic acid Angew. Chem. Int. Ed. Engl. 39 2000 3279 3281
2. J.L. Abad, F. Camps, and G. Fabrias Stereospecificity of the (Z)-9 desaturase that converts (E)-11-tetradecenoic acid into (Z,E)-9,11- tetradecadienoic acid in the biosynthesis of Spodoptera littoralis sex pheromone Insect Biochem. Mol. Biol. 31 2001 799 803
3. L.B. Bjostad, and W.L. Roelofs Sex pheromone biosynthesis from radiolabeled fatty acids in the redbanded leafroller moth J. Biol. Chem. 256 1981 7936 7940
4. L.D. Bjostad, and W.L. Roelofs Sex pheromone biosynthesis in Trichoplusia ni key steps involve delta-11 desaturation and chain shortening Science 220 1983 1387 1389
5. J.A. Broadwater, E. Whittle, and J. Shanklin Desaturation and hydroxylation. Residues 148 and 324 of Arabidopsis FAD2, in addition to substrate chain length, exert a major influence in partitioning of catalytic specificity J. Biol. Chem. 277 2002 15613 15620
6. H.R. Buser, H. Arn, P. Guerin, and S. Rauscher Determination of double bond position in mono unsaturated acetates by mass spectrometry of dimethyl disulfide adducts Anal. Chem. 55 1983 818 822
7. D.G. Campion, P. Hunter-Jones, L.J. McVeigh, D.R. Hall, R. Lester, and B.F. Nesbitt Modification of attractiveness of the primary pheromone component of the Egyptian cotton leafworm, Spodoptera littoralis (Boisduval) (Lepidoptera Noctuidae), by secondary pheromone components and related chemicals Bull. Entomol. Res. 70 1980 417 434
8. Y. Choi, Y. Park, M.W. Pariza, and J.M. Ntambi Regulation of stearoyl-CoA desaturase activity by the trans-10,cis-12 isomer of conjugated linoleic acid in HepG2 cells Biochem. Biophys. Res. Commun. 284 2001 689 693
9. E. Dunkelblum, M. Kehat, S. Gothilf, S. Greenberg, and B. Sklarsz Optimized mixture of sex pheromonal components for trapping of male Spodoptera littoralis in Israel Phytoparasitica 10 1982 21 26
10. K. Eder, N. Slomma, and K. Becker Trans-10,cis-12 conjugated linoleic acid suppresses the desaturation of linoleic and alpha-linolenic acids in HepG2 cells J. Nutr. 132 2002 1115 1121
11. 11 desaturation Experientia 46 1990 269 273
12. G. Hao, W. Liu, M. O'Connor, and W.L. Roelofs Acyl-CoA Z9- and Z10-desaturase genes from a New Zealand leafroller moth species, Planotortrix octo Insect Biochem. Mol. Biol. 32 2002 961 966
13. G. Hao, M. O'Connor, W. Liu, and W.L. Roelofs Characterization of Z/E11- and Z9-desaturases from the obliquebanded leafroller moth, Choristoneura rosaceana J. Insect Sci. 2 2002 26 online: insectscience.org/2.26
14. H. Ito, Y. Fukuda, K. Murata, and A. Kimura Transformation of intact yeast cells treated with alkali cations J. Bacteriol. 153 1983 163 168
15. J.G. Jaworski P.K. Stumpf E.E. Conn The Biochemistry of Plants vol. 9 1987 Academic Press Orlando, FL 159 174
16. S.E. Jeong, C.L. Rosenfield, P. Marsella-Herrick, K.M. You, and D.C. Knipple Multiple acyl-CoA desaturase-encoding transcripts in pheromone glands of Helicoverpa assulta, the oriental tobacco budworm Insect Biochem. Mol. Biol. 33 2003 609 622
17. R.A. Jurenka, E. Jacquin, and W.L. Roelofs Control of pheromone biosynthetic pathways in Helicoverpa zea by the pheromone biosynthesis activating neuropeptide Arch. Insect Biochem. Physiol. 17 1991 81 91
18. D.C. Knipple, C.L. Rosenfield, S.J. Miller, W. Liu, J. Tang, P.W. Ma, and W.L. Roelofs Cloning and functional expression of a cDNA encoding a pheromone gland-specific acyl-CoA Delta11-desaturase of the cabbage looper moth, Trichoplusia ni Proc. Natl. Acad. Sci. USA 95 1998 15287 15292
19. D.C. Knipple, C.-L. Rosenfield, K.M. You, and S.E. Jeong Evolution of the integral membrane desaturase gene family in moths and flies Genetics 162 2002 1737 1752
20. S. Kumar, K. Tamura, I.B. Jakobsen, and M. Nei MEGA2 molecular evolutionary genetics analysis software Bioinformatics 17 2001 1244 1245
21. W. Liu, P.W.K. Ma, P. Marsella-Herrick, C.L. Rosenfield, D.C. Knipple, and W.L. Roelofs Cloning and functional expression of a cDNA encoding a metabolic acyl-CoA delta 9-desaturase of the cabbage looper moth, Trichoplusia ni Insect Biochem. Mol. Biol. 29 1999 435 443
22. W. Liu, H. Jiao, N.C. Murray, M. O'Connor, and W.L. Roelofs Gene characterized for membrane desaturase that produces (E)-11 isomers of mono- and diunsaturated fatty acids Proc. Natl. Acad. Sci. USA 99 2002 620 624
23. W. Liu, H. Jiao, M. O'Connor, and W.L. Roelofs Moth desaturase characterized that produces both Z and E isomers of delta 11-tetradecenoic acids Insect Biochem. Mol. Biol. 32 2002 1489 1495
24. C. Lofstedt, and M. Bengtsson Sex pheromone biosynthesis of (E, E)-8, 10-dodecadienol in codling moth Cydia pomonella involves E-9 desaturation J. Chem. Ecol. 14 1988 903 914
25. A. Macartney, B. Maresca, and A.R. Cossins A.R. Cossins Temperature Adaptation of Biological Membranes 1994 Portland Press London 129 139
26. C.E. Martin, C.S. Oh, P. Kandasamy, R. Chellapa, and M. Vemula Yeast desaturases Biochem. Soc. Trans. 30 2002 1080 1082
27. T. Martinez, G. Fabrias, and F. Camps Sex pheromone biosynthetic pathway in Spodoptera littoralis and its activation by a neurohormone J. Biol. Chem. 265 1990 1381 1387
28. J.S. McElfresh, and J.G. Millar Sex pheromone of the common sheep moth, Hemileuca eglanterina, from the San Gabriel Mountains of California J. Chem. Ecol. 25 1999 687 710
29. T.A. McKeon, and P.K. Stumpf Purification and characterization of the stearoyl-acyl carrier protein desaturase and the acyl-acyl carrier protein thioesterase from maturing seeds of safflower J. Biol. Chem. 257 1982 12141 12147
30. N. Murata, and H. Wada Acyl-lipid desaturases and their importance in the tolerance and acclimatization to cold of cyanobacteria Biochem. J. 308 1995 1 8
31. I. Navarro, E. Mas, G. Fabrias, and F. Camps Identification and biosynthesis of (E,E)-10,12-tetradecadienyl acetate in Spodoptera littoralis female sex pheromone gland Bioorg. Med. Chem. 5 1997 1267 1274
32. I. Navarro, I. Font, G. Fabrias, and F. Camps Stereospecificity of the (E) and (Z)-11 myristoyl CoA desaturase in the biosynthesis of Spodoptera littoralis sex pheromone J. Am. Chem. Soc. 119 1997 11335 11336
33. B.F. Nesbitt, P.S. Beevor, R.A. Cole, R. Lester, and R.G. Poppi Sex pheromones of two noctuid moths Nat. N. Biol. 244 1973 208 209
34. J.M. Ntambi, and H. Bene Polyunsaturated fatty acid regulation of gene expression J. Mol. Neurosci. 16 2001 273 284
35. Y. Park, J.M. Storkson, J.M. Ntambi, M.E. Cook, C.J. Sih, and M.W. Pariza Inhibition of hepatic stearoyl-CoA desaturase activity by trans-10, cis-12 conjugated linoleic acid and its derivatives Biochim. Biophys. Acta, 1486 2000 285 292
36. A. Pinilla, F. Camps, and G. Fabrias Cryptoregiochemistry of the delta11-myristoyl-CoA desaturase involved in the biosynthesis of Spodoptera littoralis sex pheromone Biochemistry 38 1999 15272 15277
37. F. Rodríguez, D.L. Hallahan, J.A. Pickett, and F. Camps Characterization of the Δ11-palmitoyl-CoA desaturase from Spodoptera littoralis (Lepidoptera: Noctuidae) Insect Biochem. Mol. Biol. 22 1992 143 148
38. S. Rodríguez, F. Camps, and G. Fabrias Synthesis of gem-dideuterated tetradecanoic acids and their use in investigating the enzymatic transformation of (Z)-11-tetradecenoic acid into (E,E)-10,12- tetradecadienoic acid J. Org. Chem. 66 2001 8052 8058
39. S. Rodríguez, P. Clapes, F. Camps, and G. Fabrias Stereospecificity of an enzymatic monoene 1,4-dehydrogenation reaction conversion of (Z)-11-tetradecenoic acid into (E,E)-10,12-tetradecadienoic acid J. Org. Chem. 67 2002 2228 2233
40. W.L. Roelofs, and L. Bjostad Biosynthesis of lepidopteran pheromones Bioorg. Chem. 12 1984 279 298
41. W.L. Roelofs, and A.P. Rooney Molecular genetics and evolution of pheromone biosynthesis in Lepidoptera Proc. Natl. Acad. Sci. USA 100 2003 9179 9184
42. W.L. Roelofs, W. Liu, G. Hao, H. Jiao, A.P. Rooney, and C.E. Linn Jr. Evolution of moth sex pheromones via ancestral genes Proc. Natl. Acad. Sci. USA 99 2002 13621 13626
43. C.L. Rosenfield, K.M. You, P. Marsella-Herrick, W.L. Roelofs, and D.C. Knipple Structural and functional conservation and divergence among acyl-CoA desaturases of two noctuid species, the corn earworm, Helicoverpa zea, and the cabbage looper, Trichoplusia ni Insect Biochem. Mol. Biol. 31 2001 949 964
44. N. Saitou, and M. Nei The neighbor-joining method a new method for reconstructing phylogenetic trees Mol. Biol. Evol. 4 1987 406 425
45. R. Schneiter, V. Tatzer, G. Gogg, E. Leitner, and S.D. Kohlwein Elo1p-dependent carboxy-terminal elongation of C14 1Delta(9) to C16:1Delta(11) fatty acids in Saccharomyces cerevisiae J. Bacteriol. 182 2000 3655 3660
46. J. Shanklin, and E.B. Cahoon Desaturation and related modifications of fatty acids Annu. Rev. Plant Physiol. Plant Mol. Biol. 49 1998 611 641
47. J. Shanklin, and E. Whittle Evidence linking the Pseudomonas oleovorans alkane omega-hydroxylase, an integral membrane diiron enzyme, and the fatty acid desaturase family FEBS Lett 545 2003 188 192
48. J. Shanklin, J. Achim, H. Schmidt, B.G. Fox, and E. Munck Mossbauer studies of alkane omega-hydroxylase evidence for a diiron cluster in an integral-membrane enzyme Proc. Natl. Acad. Sci. USA 94 1997 2981 2986
49. J.E. Stukey, V.M. McDonough, and C.E. Martin The OLE1 gene of Saccharomyces cerevisiae encodes the delta 9 fatty acid desaturase and can be functionally replaced by the rat stearoyl-CoA desaturase gene J. Biol. Chem. 265 1990 20144 20149
50. Y. Tamaki, and T. Yushima Sex pheromone of the cotton leafworm, Spodoptera littoralis J. Insect Physiol. 20 1974 1005 1014
51. J.D. Thompson, T.J. Gibson, F. Plewniak, F. Jeanmougin, and D.G. Higgins The CLUSTAL_X windows interface flexible strategies for multiple sequence alignment aided by quality analysis tools Nucleic Acids Res 25 1997 4876 4882
52. J.A. Tillman, S.J. Seybold, R.A. Jurenka, and G.J. Blomquist Insect pheromones an overview of biosynthesis and endocrine regulation Insect Biochem. Mol. Biol. 29 1999 481 514
53. D.R. Tocher, M.J. Leaver, and P.A. Hodgson Recent advances in the biochemistry and molecular biology of fatty acyl desaturases Prog. Lipid Res. 37 1998 73 117
54. H. Wada, H. Schmidt, E. Heinz, and N. Murata In vitro ferredoxin-dependent desaturation of fatty acids in cyanobacterial thylakoid membranes J. Bacteriol. 175 1993 544 547
55. W.A. Wolf, and W.L. Roelofs Properties of the Δ11-desaturase enzyme used in cabbage looper moth sex pheromone biosynthesis Arch. Insect Biochem. Physiol. 3 1986 45 52
56. C. Zhao, C. Lofstedt, and X. Wang Sex pheromone biosynthesis in the Asian corn borer Ostrinia furnacalis. (II). Biosynthesis of (E)- and (Z)-12-tetradecenyl acetate involves delta 14 desaturation Arch. Insect Biochem. Physiol. 15 1990 57 65