Evidence that (+)-endo-brevicomin is a male-produced component of the southern pine beetle aggregation pheromone

Journal of Chemical Ecology

Volumn 33, Issue 8, 2007, Pages 1510-1527

  Sullivan, Brian T ^a   Shepherd, William P ^a   Pureswaran, Deepa S ^b   Tashiro, Takuya ^c   Mori, Kenji ^d  

^a USDA FOREST SERVICE   (United States)

^b MICHIGAN STATE UNIVERSITY   (United States)

^c RIKEN   (Japan)

^d UNIVERSITY OF TOKYO   (Japan)

Author keywords

Aggregation pheromone; Attractant; Bark beetle; Coleoptera; GC EAD; Scolytinae; Semiochemical; Sexual dimorphism; Synergist

Indexed keywords

BREVICOMIN; FUSED HETEROCYCLIC RINGS; PHEROMONE;

AGGREGATION PHEROMONE; ATTRACTANT; BEETLE; BIOASSAY; PEST CONTROL; SEMIOCHEMICAL; SEXUAL DIMORPHISM;

ANIMAL; ARTICLE; BEETLE; CHEMISTRY; FEMALE; GAS CHROMATOGRAPHY; MALE; METABOLISM; STEREOISOMERISM;

ANIMALS; BEETLES; BICYCLO COMPOUNDS, HETEROCYCLIC; CHROMATOGRAPHY, GAS; FEMALE; MALE; PHEROMONES; STEREOISOMERISM;

COLEOPTERA; DENDROCTONUS FRONTALIS; SCOLYTINAE;

EID: 34547470999     PISSN: 00980331     EISSN: 15731561     Source Type: Journal    
DOI: 10.1007/s10886-007-9336-8     Document Type: Article

References (49)

1. Bhattacharyya, G. K., and Johnson, R. A. 1977. Statistical Concepts and Methods. Wiley, New York.
2. Billings, R. F. 1985. Southern pine bark beetles and associated insects: effects of rapidly-released host volatiles on response to aggregation pheromones. J. Appl. Entomol. 99:483-491.
3. Borden, J. H., Ryker, L. C., Chong, L. J., Pierce, H. D. Jr., Johnston, B. D., and Oehlschlager, A. C. 1987. Response of the mountain pine beetle, Dendroctonus ponderosae Hopkins (Coleoptera: Scolytidae), to five semiochemicals in British Columbia lodgepole pine forests. Can. J. For. Res. 17:118-128.
4. Borden, J. H., CHong, L. J., and LIndgren, B. S. 1990. Redundancy in the semiochemical message required to induce attack on lodgepole pines by the mountain pine beetle Dendroctonus ponderosae Hopkins (Coleoptera: Scolytidae). Can. Entomol. 122:769-777.
5. Bridges, J. R. 1982. Effects of juvenile hormone on pheromone synthesis in Dendroctonus frontalis. Environ. Entomol. 11:417-420.
6. Browne, L. E. 1972. An emergence cage and refrigerated collector for wood-boring insects and their associates. J. Econ. Entomol. 65:1499-1501.
7. Coster, J. E., and Vité, J. P. 1965. Effects of feeding and mating on pheromone release in the southern pine beetle. Ann. Entomol. Soc. Am. 65:263-266.
8. Coster, J. E., Payne, T. L., Hart, E. R., and Edson, L. J. 1977. Aggregation of the southern pine beetle in response to attractive host trees. Environ. Entomol. 6:725-731.
9. Dickens, J. C. 1979. Electrophysiological investigations of olfaction in bark beetles. Bull. Soc. Entomol. Suisse 52:203-216.
10. Dickens, J. C., and Payne, T. L. 1977. Bark beetle olfaction: pheromone receptor system in Dendroctonus frontalis. J. Insect Physiol. 23:481-489.
11. Grosman, D. M., Salom, S. M., Ravlin, F. W., and Young, R. W. 1997. Geographic and gender differences in semiochemicals in emerging adult southern pine beetle (Coleoptera: Scolytidae). Ann. Entomol. Soc. Am. 90:438-446.
12. Hughes, P. R. 1973. Dendroctonus: production of pheromones and related compounds in response to host monoterpenes. Z. Angew. Enomol. 73:294-312.
13. Hughes, P. R., Renwick, J. A. A., and Vité, J. P. 1976. The identification and field bioassay of chemical attractants in the roundheaded pine beetle. Environ. Entomol. 5:1165-1168.
14. Mori, K., and Kiyota, H. 1992. A new synthesis of (3S,4R)-8-nonene-3,4- diol, the key intermediate for the synthesis of (+)-endo-brevicomin. Liebigs Ann. Chem. 989-992.
15. Mori, K., and Seu, Y. B. 1985. Synthesis of both the enantiomers of endo-brevicomin, the aggregation pheromone of Dryocoetes autographus. Tetrahedron 41:3429-3431.
16. Moser, J. C., Sommers, R. A., Lorio, P. L. Jr., Bridges, J. R., and Witcosky, J. J. 1987. Southern pine beetles attack felled green timber. USDA Forest Service Research Note SO-342. U.S. Department of Agriculture, Forest Service, Southern Forest Experiment Station, New Orleans, LA.
17. Payne, T. L. 1980. Life history and habits. pp. 31-54, in R. C. Thatcher, J. L. Searcy, J. E. Coster, and G. D. Hertel (eds.). The Southern Pine Beetle, U.S.D.A. Forest Service Science and Education Administration Technical Bulletin 1631. U.S. Department of Agriculture, Forest Service, Southern Forest Experiment Station, New Orleans, LA
18. Payne, T. L., and Richerson, J. V. 1979. Management implications of inhibitors for Dendroctonus frontalis (Col. Scolytidae). Bull. Soc. Entomol. Suisse 52:323-331.
19. Payne, T. L., Coster, J. E., and Johnson, P. C. 1977. Effects of slow-release formulation of synthetic endo- and exo-brevicomin on southern pine beetle flight and landing behavior. J. Chem. Ecol. 3:133-141.
20. Payne, T. L., Coster, J. E., Richerson, J. V., Edson, L. J., and Hart, E. R. 1978. Field response of the southern pine beetle to behavioral chemicals. Environ. Entomol. 7:578-582.
21. Payne, T. L., Richerson, J. V., Dickens, J. C., West J. R., Mori, K., Berisford, C. W., Hedden, R. L., Vité, J. P., and Blum, M. S. 1982. Southern pine beetle: olfactory receptor and behavior discrimination of enantiomers of the attractant pheromone frontalin. J. Chem. Ecol. 8:873-881.
22. Payne, T. L., Billings, R. F., Delorme, J. D., Andryszak, N. A., Bartels, J., Francke, W., and Vité, J. P. 1987. Kairomonal-pheromonal system in the black turpentine beetle, Dendroctonus terebrans (Ol.). J. Appl. Entomol.103:15-22.
23. Payne, T. L., Billings, R. F., Berisford, C. W., Salom, S. M., Grosman, D. M., Dalusky, M. J., and Upton, W. W. 1992. Disruption of Dendroctonus frontalis (Col. Scolytidae) infestations with an inhibitor pheromone. J. Appl. Entomol. 114:341-347.
24. Phillips, T. W., Nation, J. L., Wilkinson, R. C., Foltz, J. L., Pierce, H. D. Jr., and Oehlschlager, A. C. 1990. Response specificity of Dendroctonus terebrans (Coleoptera: Scolytidae) to enantiomers of its sex pheromones. Ann. Entomol. Soc. Am. 83:251-257.
25. Pitman, G. B., Vité, J. P., Kinzer, G. W., and Fentiman, A. F. Jr. 1969. Specificity of population-aggregating pheromones in Dendroctonus. J. Insect Physiol. 15:363-366.
26. Pureswaran, D. S., Sullivan, B. T., and Ayres, M. P. 2006. Fitness consequences of pheromone production and host selection strategies in a tree-killing bark beetle (Coleoptera: Curculionidae: Scolytinae). Oecologia 148:720-728.
27. Redlich, H., Bruns, W., Francke, W., Schurig, V., Payne, T. L., and Vité, J. P. 1987. Chiral building units from carbohydrates. XIII. Identification of the absolute configuration of endo-brevicomin from Dendroctonus frontalis and synthesis of both enantiomers from d-ribose. Tetrahedron 43:2029-2034.
28. Renwick, J. A. A., and Vité, J. P. 1969. Bark beetle attractants: mechanism of colonization by Dendroctonus frontalis. Nature 224:1222-1223.
29. Renwick, J. A. A., and Vité, J. P. 1970. Systems of chemical communication in Dendroctonus. Contrib. Boyce Thompson Inst. 24:283-292.
30. Richerson, J. V., and Payne, T. L. 1979. Effects of bark beetle inhibitors on landing and attack behavior of the southern pine beetle associates. Environ. Entomol. 8:360-364.
31. Salom, S. M., Billings, R. F., Upton, W. W., Dalusky, M. J., Grosman, D. M., Payne, T. L., Berisford, C. W., and Shaver, T. N. 1992. Effect of verbenone enantiomers and racemic endo-brevicomin on response of Dendroctonus frontalis (Coleoptera: Scolytidae) to attractant-baited traps. Can. J. For. Res. 22:925-931.
32. Seybold, S. J., and Tittiger, C. 2003. Biochemistry and molecular biology of de novo ispoprenoid pheromone production in the Scolytidae. Annu. Rev. Entomol. 48:425-53.
33. Skillen, E. L., Berisford, C. W., Camaan, M. A., and Reardon, R. C. 1997. Semiochemicals of forest and shade tree insects in North America and management applications. USDA Forest Service Forest Health Technology Enterprise Team Publication FHTET-96-15. U.S. Department of Agriculture, Forest Service, Southern Forest Experiment Station, New Orleans, LA
34. Smith, M. T., Busch, G. R., Payne, T. L., and Dickens, J. C. 1988. Antennal olfactory responsiveness of three sympatric Ips species [Ips avulsus (Eichhoff), Ips calligraphus (Germar), Ips grandicollis (Eichhoff)], to intra- and interspecific behavioral chemicals. J. Chem. Ecol. 14:1289-1304.
35. Smith, M. T., Salom, S. M., and Payne, T. L. 1993. The southern pine bark beetle guild: a historical review of the research on the semiochemical-based communication system of the five principal species. Virginia Agricultural Experiment Station Bulletin 93-4. Virginia Agricultural Experiment Station, Blacksburg, VA.
36. spss. 1997. SigmaStat® 2.0 for Windows® User's Manual. SPSS Inc., Chicago, IL.
37. Sullivan, B. T. 2005. Electrophysiological and behavioral responses of Dendroctonus frontalis (Coleoptera: Curculionidae) to volatiles isolated from conspecifics. J. Econ. Entomol. 98:2067-2078.
38. Sullivan, B. T., Dalusky, M. J., Wakarchuk, D., and Berisford, C. W. 2007. Field evaluations of potential aggregation inhibitors for the southern pine beetle, Dendroctonus frontalis (Coleoptera: Curculionidae). J. Entomol. Sci. 42:139-149.
39. Svihra, P. 1982. Influence of opposite sex on attraction produced by pioneer sex of four bark beetles species cohabiting pine in the southern United States. J. Chem. Ecol. 8:373-378.
40. Tisdale, R. A., Nebeker, T. E., and Hodges, J. D. 2003. Role of oleoresin flow in initial colonization of loblolly pine by southern pine beetle. J. Entol. Sci. 38:576-582.
41. Vité, J. P., and Pitman, G. B. 1968. Bark beetle aggregation: effects of feeding on the release of pheromones in Dendroctonus and Ips. Nature 218:169-170.
42. Vité, J. P., and Renwick, J. A. A. 1968. Insect and host factors in the aggregation of the southern pine beetle. Contrib. Boyce Thompson Inst. 24:61-63.
43. Vité, J. P., and Pitman, G. B. 1969. Aggregation behavior of Dendrocotnus brevicomis in response to synthetic pheromones. J. Insect Phyiol. 15:1617-1622.
44. Vité, J. P., and Renwick, J. A. A. 1971. Inhibition of Dendroctonus frontalis response to frontalin by isomers of brevicomin. Naturwissenschaften 8:418-419.
45. Vité, J. P., and Francke, W. 1976. The aggregation pheromones of bark beetles: Progress and problems. Naturwissenschaften 63:550-555.
46. Vité, J. P., Billings, R. F., Ware, C. W., and Mori, K. 1985. Southern pine beetle: enhancement or inhibition of aggregation response mediated by enantiomers of endo-brevicomin. Naturwissenschaften 72:99.
47. Whitehead, A. T. 1986. Electroantennogram responses by mountain pine beetles, Dendroctonus ponderosae Hopkins, exposed to selected semiochemicals. J. Chem. Ecol. 12:1603-1621.
48. Wood, D. L., and Bedard, W. D. 1977. The role of pheromones in the population dynamics of the western pine beetle. Proc. Int. Congr. Entomol. 15:643-652.
49. Wood, S. L. 1982. The bark and ambrosia beetles of North and Central America (Coleoptera: Scolytidae), a taxonomic monograph. Gt. Basin Nat. Mem. 6:1359.