The convergent evolution of defensive polyacetylenic fatty acid biosynthesis genes in soldier beetles

Nature Communications

Volumn 3, Issue , 2012, Pages

  Haritos, Victoria S ^a   Horne, Irene ^a   Damcevski, Katherine ^a   Glover, Karen ^a   Gibb, Nerida ^a   Okada, Shoko ^a   Hamberg, Mats ^b  

^a CSIRO   (Australia)

^b KAROLINSKA INSTITUTE   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

ACETYLENASE; ACYL COENZYME A DESATURASE; COMPLEMENTARY DNA; DIHYDROMATRICARIA ACID; FATTY ACID; POLYACETYLENIC FATTY ACID; RNA; UNCLASSIFIED DRUG;

BEETLE; BIOCHEMISTRY; CATALYSIS; CONVERGENT EVOLUTION; ENZYME ACTIVITY; FATTY ACID; GENE EXPRESSION; PHYLOGENETICS; PREDATION; SOLDIER CASTE; YEAST;

ARTICLE; AUSTRALIA; BEETLE; BIOSYNTHESIS; CATALYSIS; CHEMICAL STRUCTURE; ENZYME ACTIVITY; EVOLUTION; FATTY ACID SYNTHESIS; FUNGUS; GAS CHROMATOGRAPHY; GENE EXPRESSION; GENE SEQUENCE; HOST RESISTANCE; MOLECULAR CLONING; NONHUMAN; NUCLEOTIDE SEQUENCE; PHYLOGENY; PREDATOR; SOLDIER (INSECT); YEAST;

ALKYNES; ANIMALS; BEETLES; BIOLOGICAL EVOLUTION; CLONING, MOLECULAR; EVOLUTION, MOLECULAR; FATTY ACID DESATURASES; FATTY ACIDS; FATTY ACIDS, UNSATURATED; GENES, INSECT; INSECTS; MALE; PHYLOGENY; POLYACETYLENES;

AVES; CANTHARIDAE; EUKARYOTA; FUNGI;

EID: 84869464204     PISSN: None     EISSN: 20411723     Source Type: Journal    
DOI: 10.1038/ncomms2147     Document Type: Article

References (41)

1. Meinwald, J., Meinwald, Y. C., Chalmers, A. M. & Eisner, T. Dihydromatricaria acid: acetylenic acid secreted by soldier beetle. Science 160, 890-892 (1968).
2. Brown, W. V., Lacey, M. J. & Moore, B. P. Dihydromatricariate-based triglycerides, glyceride ethers, and waxes in the Australian soldier beetle, Chauliognathus lugubris (Coleoptera:Cantharidae). J. Chem. Ecol. 14, 411-423 (1988).
3. Eisner, T. et al. Antifeedant action of Z-dihydromatricaria acid from soldier beetles. J. Chem. Ecol. 7, 1149-1158 (1981).
4. Sörensen, N. A. Some naturally occurring acetylene compounds. Proc. Chem. Soc. (London) 98-110 (1961).
5. Jones, E. R. H. & Thaller, V. in The Chemistry of the Carbon-Carbon Triple Bond Part 2, (ed Patai, S.) 621-633 (John Wiley and Sons, 1978).
6. Duffey, S. S. Sequestration of plant natural products by insects. Annu. Rev. Entomol. 25, 447-477 (1980).
7. Lee, M. et al. Identification of non-heme diiron proteins that catalyze triple bond and epoxy group formation. Science 280, 915-918 (1998). (Pubitemid 28215604)
8. Blacklock, B. J., Scheffler, B. E., Shepard, M. R., Jayasuriya, N. & Minto, R. E. Functional diversity in fungal fatty acid synthesis. The first acetylenase from the pacific golden chanterelle, Cantharellus formosus. J. Biol. Chem. 285, 28442-28449 (2010).
9. Reed, D. W. et al. Mechanistic study of an improbable reaction: alkene dehydrogenation by the Δ12 acetylenase of Crepis alpina. J. Am. Chem. Soc. 125, 10635-10640 (2003). (Pubitemid 37055916)
10. Sperling, P., Ternes, P., Zank, T. K. & Heinz, E. The evolution of desaturases. Prostaglandins Leukot. Essent. Fatty Acids 68, 73-95 (2003). (Pubitemid 36216472)
11. Vanhercke, T., Shrestha, P., Green, A. G. & Singh, S. P. Mechanistic and structural insights into the regioselectivity of an acyl-CoA fatty acid desaturase via directed molecular evolution. J Biol. Chem. 286, 12860-12869 (2011).
12. Christensen, L. P. Biological activities of naturally occurring acetylenes and related compounds from higher plants. Recent Res. Dev. Phytochem. 2, 227-257 (1998).
13. Liu, W., Christenson, S. D., Standage, S. & Shen, B. Biosynthesis of the enediyne antitumor antibiotic C-1027. Science 297, 1170-1173 (2002). (Pubitemid 36193350)
14. Carballeira, N. M. et al. New advances in fatty acids as antimalarial, antimycobacterial and antifungal agents. Lipids 41, 507-511 (2006). (Pubitemid 44204873)
15. Christensen, L. P. & Brandt, K. Bioactive polyacetylenes in food plants of the Apiaceae family: occurrence, bioactivity and analysis. J. Pharma. Biomed. Anal. 41, 683-693 (2006).
16. Dembitsky, V. M. Anticancer activity of natural and synthetic acetylenic lipids. Lipids 41, 883-924 (2006). (Pubitemid 44871578)
17. Shi Shun, A. L. K. & Tykwinski, R. R. Synthesis of naturally occurring polyynes. Angew. Chem. Int. Ed. Engl. 45, 1034-1057 (2006). (Pubitemid 44104884)
18. Li, X.-C. et al. Potent in vitro antifungal activities of naturally occurring acetylenic acids. Antimicrob. Agents Chemother. 52, 2442-2448 (2008). (Pubitemid 351915674)
19. Minto, R. E. & Blacklock, B. J. Biosynthesis and function of polyacetylenes and allied natural products. Prog. Lipid Res. 47, 233-306 (2008).
20. Van Lanen, S. G. & Shen, B. Biosynthesis of enediyne antitumor antibiotics. Curr. Top. Med. Chem. 8, 448-459 (2008). (Pubitemid 351982587)
21. Shanklin, J., Whittle, E. & Fox, B. G. Eight histidine residues are catalytically essential in a membrane-associated iron enzyme, stearoyl-CoA desaturase, and are conserved in alkane hydroxylase and xylene monooxygenase. Biochemistry 33, 12787-12794 (1994). (Pubitemid 24352868)
22. Horne, I., Gibb, N., Damcevski, K., Glover, K. & Haritos, V. Two conserved Z9-octadecanoic acid desaturases in the red flour beetle, Tribolium castaneum. Gene 468, 41-47 (2010).
23. Serra, M., Pina, B., Abadm, J. L., Camps, F. & Fabrias, G. A multifunctional desaturase involved in the biosynthesis of the processionary moth sex pheromone. Proc. Natl Acad. Sci. USA 104, 16444-16449 (2007). (Pubitemid 350211039)
24. Zhou, X. R. et al. Isolation and functional characterization of two independently-evolved acyl-CoA Δ12-desaturase genes from insects. Insect Mol. Biol. 17, 667-676 (2008).
25. Bu'lock, J. D. & Smith, G. N. The origin of naturally-occurring acetylenes. J. Chem. Soc (C) 332-336 (1967).
26. Christensen, L. P. & Lam, J. Acetylenes and related compounds in Astereae. Phytochemistry 30, 2453-2476 (1991).
27. Bohlmann, F. & Burkhardt, T. Zur Biogenese des Matricaria esters. Chem. Ber. 105, 521-528 (1972).
28. Hughes, A. L. The evolution of functionally novel proteins after gene duplication. Proc. Biol. Sci. 256, 119-124 (1994). (Pubitemid 24168165)
29. Force, A. et al. Preservation of duplicate genes by complementary, degenerative mutations. Genetics 151, 1531-1545 (1999). (Pubitemid 29177561)
30. He, X. & Zhang, J. Rapid subfunctionalization accompanied by prolonged and substantial neofunctionalization in duplicate gene evolution. Genetics 169, 1157-1164 (2005). (Pubitemid 40404340)
31. Avato, P., Vitali, C., Mongelli, P. & Tava, A. Antimicrobial activity of polyacetylenes from Bellis perennis and their synthetic derivatives. Planta Med. 63:503-507 (1997). (Pubitemid 28035443)
32. Luo, L. H. et al. Depigmentation of melanocytes by (2Z,8Z)-matricaria acid methyl ester isolated from Erigeron breviscapus. Biol. Pharm. Bull. 32, 1091-1094 (2009).
33. Matsunaga, H. et al. Inhibitory effect of cis-dehydromatricaria ester isolated from Solidago altissima on the growth of mammalian cells. Chem. Pharm. Bull. (Tokyo) 38, 3483-34844 (1990).
34. Kagan, J., Kolyvas, C. P. & Lam, J. The ovicidal activity of cis-dehydromatricaria ester: time-dependance of its enhancement by UV light. Experientia 40, 1396-1397 (1984). (Pubitemid 15179233)
35. Cahoon, E. B., Schnurr, J. A., Huffman, E. A. & Minto, R. E. Fungal responsive fatty acid acetylenases occur widely in evolutionarily distant plant families. Plant J. 34, 671-683 (2003). (Pubitemid 36720201)
36. Fallis, A. G., Hearn, M. T. W., Jones, E. R. H., Thaller, V. & Turner, J. L. Natural acetylenes. Part XL. Synthesis of polyacetylenic C18 and C16 esters with 9-ene-12,14-diyne unsaturation, and their labeling. J. Chem. Soc. Perkin Trans. 1, 743-749 (1973).
37. Lie Ken Jie, M. S. F. & Cheung, Y. K. Synthesis and physical properties of some unsaturated and hydroxyl alkyseleno fatty acid derivatives. Chem. Phys. Lipids 75, 71-80 (1995).
38. Fiandanese, V., Bottalico, D., Marchese, G. & Punzi, A. New stereoselective methodology for the synthesis of dihydroxerulin and xerulin, potent inhibitors of the biosynthesis of cholesterol. Tetrahedron 60, 11421-11425 (2004). (Pubitemid 39505307)
39. Thompson, J. D., Higgins, D. G. & Gibson, T. J. CLUSTAL W: improving the sensitivity of progressive multiple sequence alignment through sequence weighting, position-specific gap penalties and weight matrix choice. Nucleic Acids Res. 22, 4673-4680 (1994). (Pubitemid 24354800)
40. Saitou, N. & Nei, M. The neighbor-joining method: a new method for reconstructing phylogenetic trees. Mol. Biol. Evol. 4, 406-425 (1987).
41. Tamura, K., Dudley, J., Neim, M. & Kumar, S. Mega4: molecular evolutionary genetics analysis (MEGA) software version 4.0. Mol. Biol. Evol. 24, 1596-1599 (2007). (Pubitemid 47236692)