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Sex Pheromone of Lonomia obliqua: Daily Rhythm of Production, Identification, and Synthesis

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Abstract

The sex pheromone of Lonomia obliqua Walker (Lepidoptera: Saturniidae) was studied in the laboratory. All female calling occurred during the scotophase. Most females (70.6%) called first within 24 hr of eclosion. Calling varied with age of female, with older (5- to 6-day-old) females calling earlier in the scotophase and for longer durations than younger (0- to 1-day-old) females. The sex pheromone gland of 1- to 3-day-old virgin females was extracted during the calling peak. A Y-olfactometer bioassay showed significant attraction of males to a filter paper containing the female gland extract. Gas chromatographic-electroantennogram detection (GC-EAD) analysis of the extract indicated the presence of at least two possible pheromone components. Gas chromatographic-mass spectrometric analysis of the major GC-EAD-active peak indicated a hexadecenyl acetate; chemical derivatization indicated Δ11 unsaturation. Synthetic samples of (E)- and (Z)-11-hexadecenyl acetate were obtained by coupling 10-bromo-1-decanol and 1-hexyne, utilizing lithium chemistry. The comparison of the retention time of dimethyl disulfide derivatives of the natural compound, to those of synthetic chemicals, confirmed the natural compound as (E)-11-hexadecenyl acetate. The minor component was identified as the related alcohol, (E)-11-hexadecenol. The ratio of the two components in female extract was 100:35. Preliminary tests of males in a Y-olfactometer showed that their response to a mixture of the two compounds was not significantly different from that to gland extract.

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References

  • Attygalle, A. B. 1998. Microchemical techniques, pp. 207–294, in J. G. Millar and K. F. Haynes (eds.). Methods in Chemical Ecology V1. Kluwer Academic Publishers, Norwell, Massachusetts.

    Google Scholar 

  • Bestmann, H. J., Attygalle, A. B., Schwarz, J., Wolfgang, G., Vostrowisky, O. and Tomida, I. 1989. Pheromones identification and synthesis of female sex pheromone of eri-silkworm, Samia cynthia ricini (Lepidoptera: Saturniidae). Tetrahedron Lett. 22:2911–2914.

    Article  Google Scholar 

  • Caserio, M. C., Fisher, C. L. and Kim, J. K. 1985. Boron trifluoride catalyzed addition of disulfide to alkenes. J. Org. Chem. 50:4390–4393.

    Article  CAS  Google Scholar 

  • Crawley, M. 2002. Statistical Computing, An Introduction to Data Analysis Using S-Plus. John Wiley & Sons, Ltd. 761 p.

  • Crawley, M. 2005. Statistics. An Introduction to Using R. John Wiley & Sons, Ltd. 327 p.

  • Duarte, A. C., Caovilla, A. J., Lorini, I., Lorini, D., Mantovani, G., Sumida, J., Manfre, P. C., Silveira, R. C. and Moura, S. P. 1990. Insuficiência renal aguda por acidentes com lagartas. J. Bras. Nefrol. 12:184–187.

    Google Scholar 

  • Fornés, L. and Hernández, J. V. 2000. Algunos aspectos de la biología de Hylesia metabus (Cramer 1775) (Lepidoptera: Saturniidae). Bol. Entomol. Venez. 15:127–145.

    Google Scholar 

  • Henderson, H. E., Warren, O. P. H., Augustyn, B. V., Burger, D. F., Schneider, A., Boshoff, P. R., Spies, H. S. C. and Geertsema, H. 1973. Isolation and structure of the sex-pheromone of the moth. Nudaurelia cytherea cytherea. J. Insect Physiol. 19:1257–1264.

    Article  CAS  Google Scholar 

  • Kang, S.-K. and Park, S.-K. 1988. A stereoselective synthesis of (Z, Z)-3,13-octadecadien-1-yl acetate, and its (E, Z)-isomer, the sex pheromone of the cherry tree borer, Synanthedon hector Butler. Bull. Korean Chem. Soc. 9:149–152.

    CAS  Google Scholar 

  • Kochansky, J. P., Tette, J., Taschenberg, E. F., Cardé, R. T., Kaissling, K. E. and Roelofs, W. L. 1975. Sex pheromone of the Antheraea polyphemus. J. Insect Physiol. 21:1977–1983.

    Article  CAS  Google Scholar 

  • Leal, W. S., Mochizuki, F., Wakamura, S. and Yasuda, T. 1992. Eletroantennografic detection of Anomala cuprea sex pheromone. Appl. Entomol. Zool. 27:289–291.

    Google Scholar 

  • Leal, W. S., Kawamura, F. and Ono, M. 1994. The scarab beetle Anomala albopilosa sakishimana utilizes the same sex pheromone blend as a closely related and geographically isolated species, Anomala cuprea. J. Chem. Ecol. 20:1667–1676.

    Article  CAS  Google Scholar 

  • Lorini, L. M. 1999. A taturana, aspectos biológicos e morfológicos da Lonomia obliqua. Ediupf, Passo Fundo, p. 67.

    Google Scholar 

  • Lorini, L. M. and Corseuil, É. 2001. Aspectos morfológicos de Lonomia obliqua Walker, 1855 (Lepidoptera: Saturniidae) em laboratório. Neotrop. Entomol. 30:373–378.

    Article  Google Scholar 

  • Lorini, L. M., Rebelato, G. S. and Bonatti, J. 2004. Reproductive parameters of Lonomia obliqua Walker, 1855, (Lepidoptera: Saturniidae) in laboratory. Braz. Arch. Biol. Technol. 47:575–577.

    Article  Google Scholar 

  • McElfresh, J. S. and Millar, J. G. 1999a. Sex pheromone of the common sheep moth Hemileuca eglanterina, from the San Gabriel Mountains of California. J. Chem. Ecol. 25:687–709.

    Article  CAS  Google Scholar 

  • McElfresh, J. S. and Millar, J. G. 1999b. Sex attractant pheromone of saturniid moth Coloradia velda. J. Chem. Ecol. 25:1067–1078.

    Article  CAS  Google Scholar 

  • McElfresh, J. S. and Millar, J. G. 1999c. Sex pheromone of Nuttall’s sheep moth Hemileuca nuttalli from The Eastern Sierra Nevada Mountains of California. J. Chem. Ecol. 25:711–726.

    Article  CAS  Google Scholar 

  • McElfresh, J. S., Hammond, A. M. and Millar, J. G. 2001a. Sex pheromone components of the buck moth Hemileuca maia. J. Chem. Ecol. 27:1409–1422.

    Article  PubMed  CAS  Google Scholar 

  • McElfresh, J. S., Millar, J. G. and Rubinoff, D. 2001b. (E4, Z9)-Tetradecadienal, a sex pheromone for three North American moth species in the genus Saturnia. J. Chem. Ecol. 27:791–806.

    Article  PubMed  CAS  Google Scholar 

  • Parra, A. L. G. C., Vilela, E. F. and Bento, J. M. S. 2002. Horário de oviposição e ritmo diário de emergência de Phyllocnistis citrella Stainton (Lepidoptera: Gracillariidae) em Laboratório. Neotrop. Entomol. 31:365–368.

    Article  Google Scholar 

  • Parra-Pedrazzoli, A. L., Cossé, A., Murata, Y., Bento, J. M. S., Vilela, E. F. and Leal, W. S. 2006. Towards the identification and synthesis of the sex pheromone of the citrus leafminer, Phyllocnistis citrella Stainton (Lepidoptera: Gracillariidae). Neotrop. Entomol. 35:12–18.

    Article  CAS  Google Scholar 

  • R Development Core Team. 2005. R: A Language and Environment for Statistical Computing. R Foundation for Statistical Computing, Vienna, Austria.

  • Statistica, Stat Soft, Inc. 1999. Statistic for Windows.

  • Swier, S. R., Rings, R. W. and Musick, G. J. 1977. Age-related calling behaviour of the black cutworm Agrotis ipsilon. Ann. Entomol. Soc. Am. 70:919–924.

    Google Scholar 

  • Turgeon, J. and Mcneil, J. 1982. Calling behaviour of the armyworm Pseudaletia unipuncta. Entomol. Exp. Appl. 31:402–408.

    Google Scholar 

  • Vincenti, M., Guglielmetti, G., Cassani, G. and Toninni, C. 1987. Determination of double-bond position in diunsaturated compounds by mass-spectrometry of dimethyl disulfide derivatives. Anal. Chem. 59:694–699.

    Article  Google Scholar 

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Acknowledgments

We thank the International Foundation for Science—Sweden, the Organization for the Prohibition of Chemicals Weapons—The Netherlands, CNPq, Fundação Araucária, and the Embrapa/Prodetab for the financial support.

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Authors and Affiliations

  1. Departamento de Química, Laboratório de Semioquímicos, Universidade Federal do Paraná, C. Postal 19081, 81531-990, Curitiba-PR, Brazil

    Paulo H. G. Zarbin, Lisete M. Lorini, Bianca G. Ambrogi & Diogo M. Vidal

  2. Laboratório de Semioquímicos e Comportamento de Insetos, Departamento de Biologia Animal, Universidade Federal de Viçosa, 36570-000, Viçosa-MG, Brazil

    Eraldo R. Lima

  3. Departamento de Biologia, Universidade de Passo Fundo, C. Postal 611, 99001-70, Passo Fundo-RS, Brazil

    Lisete M. Lorini

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  1. Paulo H. G. Zarbin
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  2. Lisete M. Lorini
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Correspondence to Paulo H. G. Zarbin.

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Zarbin, P.H.G., Lorini, L.M., Ambrogi, B.G. et al. Sex Pheromone of Lonomia obliqua: Daily Rhythm of Production, Identification, and Synthesis. J Chem Ecol 33, 555–565 (2007). https://doi.org/10.1007/s10886-006-9246-1

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  • DOI: https://doi.org/10.1007/s10886-006-9246-1

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