Trans-Bergamotenes - Male pheromone of the ectoparasitoid Melittobia digitata

Journal of Chemical Ecology

Volumn 28, Issue 8, 2002, Pages 1675-1689

  Cônsoli, Fernando L ^a   Williams, Howard J ^b   Vinson, S Bradleigh ^a   Matthews, Robert W ^c   Cooperband, Miriam F ^a  

^a Department of Entomology ^*  (United States)

^b TEXAS A AND M UNIVERSITY   (United States)

^c UNIVERSITY OF GEORGIA   (United States)

Author keywords

Courtship; Parasitoid; Sesquiterpene; Sex pheromone; Sex recognition

Indexed keywords

ALPHA BERGAMOTENE; BETA BERGAMOTENE; SESQUITERPENE; SESQUITERPENE DERIVATIVE; SEX PHEROMONE; UNCLASSIFIED DRUG;

ATTRACTANT; COURTSHIP; ECTOPARASITE; PARASITE; PHEROMONE;

AGING; ANIMAL; ARTICLE; CHEMISTRY; COURTSHIP; ECTOPARASITE; FEMALE; FLY; MALE; MASS SPECTROMETRY; MELITTOBIA DIGITATA; METABOLISM; NONHUMAN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SEXUAL BEHAVIOR; SEXUAL SELECTION;

ANIMALS; DIPTERA; FEMALE; MAGNETIC RESONANCE SPECTROSCOPY; MALE; MASS SPECTROMETRY; SESQUITERPENES; SEX ATTRACTANTS;

ANIMALIA; APOIDEA; HYMENOPTERA; MELITTOBIA; MELITTOBIA DIGITATA; VESPIDAE;

EID: 0036694667     PISSN: 00980331     EISSN: None     Source Type: Journal    
DOI: 10.1023/A:1019940932605     Document Type: Article

References (39)

1. Asekun, O. T. and Ekundayo, O. 2000. Essential oil constituents of Hyptis suaveolens (L.) Poit. (Bush tea) leaves from Nigeria. J. Essent. Oil Res. 12:227-230.
2. Assem, J. van den 1986. Parasitoid mating behavior, pp. 137-163, in J. Waage and D. Greathead (eds.). Insect Parasitoids. Academic Press, New York.
3. Assem, J. van den and Jackmann, F. 1982. The coevolution of receptivity signaling and body size in the Chalcidoidea. Behaviour 80:96-105.
4. Assem, J. van den and Povel, G. D. E. 1973. Courtship behaviour of some Muscidifurax species (Hym., Pteromalidae): a possible example of a recently evolved ethological isolating mechanism. Neth. J. Zool. 23:465-487.
5. Assem, J. van den, Bosch, H. A. J., and Prooy, E. 1982. Melittobia courtship behaviour: a comparative study of evolution of a display. Neth. J. Zool. 32:427-471.
6. Ayasse, M., Paxton, R. J., and Tengö, J. 2001. Mating behavior and chemical communication in the order Hymenoptera. Annu. Rev. Entomol. 46:31-78.
7. Benedict, C. R., Lu, J. L., Petrigrew, D. W., Liu, J., Stipanovic, R. D., and Williams, H. J. 2001. The cyclization of farnesyl diphosphate and nerolidyl diphosphate by a purified recombinant δ-cadinene synthase. Plant Physiol. 125:1754-1765.
8. Bestmann, H. J., Classen, B., Kobold, U., Vostrowsky, O., Klingauf, F., and Stein, U. 1988. Steam volatile constituents from leaves of Rhus typhina. Phytochemistry 27:85-90.
9. Birkinshaw, L. A. and Smith, R. H. 2000. Function of aggregation pheromone in the larger grain borer Prostephanus truncatus. Variation in response to individuals as evidence for a role in sexual selection. J. Chem. Ecol. 26:1325-1339.
10. Dahms, E. C. 1973. The courtship behaviour of Melittobia australica Girault, 1912 (Hymenoptera: Eulophidae). Mem. Queensl. Mus. 16:411-414.
11. Dahms, E. C. 1984a. Revision of the genus Melittobia (Chalcidoidea: Eulophidae) with the description of seven new species. Mem. Queensl. Mus. 21:271-336.
12. Dahms, E. C. 1984b. A review of the biology of species in the genus Melittobia (Hymenoptera: Eulophidae) with interpretations and additions using observations on Melittobia australica. Mem. Queensl. Mus. 21:337-360.
13. Dahms, E. C. 1984c. An interpretation of the structure and function of the antennal sense organs of Melittobia australica (Hymenoptera: Eulophidae) with the discovery of a large dermal gland in the male scape. Mem. Queensl. Mus. 21:361-385.
14. Evans, D. A. and Matthews, R. W. 1976. Comparative courtship behaviour in two species of the parasitic chalcid wasp Melittobia (Hymenoptera: Eulophidae). Anim. Behav. 24:46-51.
15. Flath, R. A., Cunningham, R. T., Mon, T. R., and John, J. O. 1994a. Additional male Mediterranean fruitfly (Ceratitis capitata Wied.) attractants from angelica seed oil (Angelica archangelica L.). J. Chem. Ecol. 8:1969-1984.
16. Flath, R. A., Cunningham, R. T., Mon, T. R., and John, J. O. 1994b. Male lures for Mediterranean fruitfly (Ceratitis capitata Wied.): structural analogs of α-copaene. J. Chem. Ecol. 20:2595-2609.
17. Godfray, H. C. J. 1994. Parasitoids: Behavioral and Evolutionary Ecology. Princeton University Press, Princeton, New Jersey.
18. Gonzalez, J. M., Matthews, R. W., and Matthews, J. R. 1985. A sex pheromone in males of Melittobia australica and M. femorata (Hymenoptera: Eulophidae). Fla. Entomol. 68:279-286.
19. Gonzalez, J. M., Matthews, R. W., and Terán, J. B. 1996. Cortejo en las avispas parasitoides Melittobia acasta y Melittobia australica (Hymenoptera: Eulophidae). Rev. Biol. Trop. 44:687-692.
20. Guinan, J. A., Matthews, R. W., and Matthews, J. R. 2000. Courtship reaction chains and mate attraction: a two-part laboratory activity using WOWBugs, a new model insect, pp. 380-404, in S. J. Karcher (ed.). Tested Studies for Laboratory Teaching, Vol. 21. Proceedings, 21st Workshop/Conference of the Association for Biology Laboratory Education (ABLE).
21. Hermann, L. D., Hermann, H. R., and Matthews, R. W. 1974. A possible calling pheromone in Melittobia chalybii (Hymenoptera: Eulophidae). J. Ga. Entomol. Soc. 9:17.
22. Huang, Q., Williams, H. J., Roessner, C. A., and Scott, A. I. 2000. Sesquiterpenes produced by truncated taxadiene synthase. Tetrahedron Lett. 41:9701-9704.
23. Kainoh, Y. 1999. Parasitoids, pp. 383-404, in J. Hardie and A. K. Minks (eds.). Pheromones of Non-Lepidopteran Insects Associated with Agricultural Plants. CAB International, Wallingford, United Kingdom.
24. Kite, G. C. and Leon, C. 1995. Volatile compounds emitted from flowers and leaves of Brugmansia x candida (Solanaceae). Phytochemistry 40:1093-1095.
25. Krishnappa, S. and Dev, S. 1973. Sesquiterpenes from Lansium anamalayanum. Phytochemistry 12:823-825.
26. Kulkarni, Y. S., Niwa, M., Ron, E., and Snider, B. B. 1987. Synthesis of terpenes containing the bicyclo[3.3.3]heptane ring system by the intramolecular [2 + 2] cycloaddition reaction of vinylketenes with alkenes. Preparation of chrysanthenone, β-pinene, β-cis-bergamotene, β-transbergamotene, β-copaene, and β-ylangene and lemnalol. J. Org. Chem. 52:1568-1576.
27. Leitão, G. G., Menezes, D. L. F. de, Kaplan, M. A. C., Craveiro, A. A., and Alencar, J. W. 1991. Essential oils from Brazilian Aristolochia. J. Essent. Oil Res. 3:403-408.
28. Matthews, R. W. 1975. Courtship in parasitic wasps, pp. 66-111, in P. W. Price (ed.). Evolutionary Strategies of Parasitic Insects and Mites. Plenum Press, New York.
29. Matthews, R. W., Yukawa, J., and Gonzalez, J. M. 1985. Sex pheromone in male Melittobia parasitic wasps: female response to conspecific and congeneric males of 3 species. J. Ethol. 3:59-62.
30. Minyard, J. P., Tumlinson, J. H., Thompson, A. C., and Hedin, P. A. 1966. Constituents of the cotton bud: sesquiterpene hydrocarbons. J. Agric. Food Chem. 14:332-336.
31. Njoroge, S. M., Ukeda, H., Kusunose, H., and Sawamura, M. 1996. Japanese sour Citrus fruits. Part IV. Volatile compounds of naoshichi and Tahiti lime essential oils. Flav. J. 11:25-29.
32. Pino, J. A., Rosado, A., and Aguero, J. 2000. Volatile components of avocado (Persea americana Mill.) fruits. J. Essent. Oil Res. 12:377-378.
33. Quicke, D. L. J. 1997. Parasitic Wasps. Chapman & Hall, London, 470 pp.
34. Rocca, J. R., Nation, J. L., Strekowski, L., and Batfiste, M. A. 1992. Comparison of volatiles emitted by male Caribbean and Mexican fruit flies. J. Chem. Ecol. 18:223-244.
35. Sanda, K., Koba, K., Nambo, P., and Gaset, A. 1998. Chemical investigation of Ocimum species growing in Togo. Flav. Frag. J. 13:226-232.
36. Snider, B. B. and Beal, R. B. 1988. Total synthesis of sesquiterpenes via intramolecular ketene cycloadditions: isocomene and α-cis- and α-trans-bergamotenes, and approach to seychellene. J. Org. Chem. 53:4508-4515.
37. Tillman, J. A., Seybold, S. J., Jurenka, R. A., and Blomquist, G. J. 1999. Insect pheromones - an overview of biosynthesis and endocrine regulation. Insect. Biochem. Mol. Biol. 29:481-514.
38. Turlings, T. C. J., Tumlinson, J. H., Heath, R. R., Proveaux, A. T., and Doolittle, R. E. 1991. Isolation and identification of allelochemicals that attract the larval parasitoid, Cotesia marginiventris (Cresson), to the microhabitat of one of its hosts. J. Chem. Ecol. 17:2235-2251.
39. Williams, H. J. and Vinson, S. B. 1980. All glass system for preparative gas chromatography using capillary columns. J. Chem. Ecol. 6:973-978.