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Male pheromone of swift moth,Hepialus hecta L. (Lepidoptera: Hepialidae)

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Abstract

(R)-6-Ethyl-2-methyl-2,3-dihydro-4H-pyran-4-one, (1R,3S,5R)-3-ethyl-1,8-dimethyl-2,9-dioxabicyclo[3.3. 1]non-7-ene, and (1R,3S,5R)-3-ethyl-1,8-dimethyl-2,9-dioxabicyclo[3.3.1]non-7-en-6-one represent the main components in the male pheromone of the swift moth,Hepialus hecta. The amounts of the three components were 40, 5, and 5 μg per male, respectively. Structure elucidation of the compounds was based on spectroscopic data as compared to synthetic reference samples. The absolute configurations were determined by gas chromatography on chiral stationary phases; optically active samples served as reference compounds. Electrophysiological and behavioral experiments with natural material and synthetic samples clearly showed the three heterocyclic compounds to act as pheromones. (E, E)-α-Farnesene represents the main component of the scent secretion of maleHepialus humuli.

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References

  • Bertkau, P. 1882. Ueber den Duftapparat vonHepialus hectusL.Arch. Naturgesch. 17:223–224.

    Google Scholar 

  • Boppré, M. 1984. Chemically medicated interactions between butterflies, pp. 259–275in R.I. Vane-Wright, and P.R. Ackery (eds.). The Biology of Butterflies. Academic Press, London.

    Google Scholar 

  • Bopprë, M., andSchneider, D. 1989. The biology ofCreatonotos (Lepidoptera: Arctiidae) with special reference to the androconial system.Zool. J. Linn. Soc. 96:339–356.

    Google Scholar 

  • Deshong, S., Ramesh, S., Elango, V., andPerez, J.J. 1985. Total synthesis of (±)-triandamycin A.J. Am Chem. Soc. 107:5219–5224.

    Google Scholar 

  • Francke, W., Mackenroth, W., Schröder, W., Schultz, S., Tengö, J., Engel, E., Engels, W., Kittmann, R., andSchneider, D. 1985. Identification of cyclic enolethers from insects: Alkyldihydropyranes from bees and alkyldihydro-4H-pyran-4-ones from male moth.Naturwissenschaften 40c:145–147.

    Google Scholar 

  • Francke, W., Schulz, S., Sinnwell, A., König, W.A., andRoisin, Y. 1989. Epoxytetrahydroedulan, a new terpenoid from the hairpencils ofEuploea (Lep.: Danainae) butterflies.Liebigs Ann. Chem. 1989:1195–1201.

    Google Scholar 

  • Gelin, S., andGelin, R. 1968. Synthéses et propriétés de dihydropyrones-4 et de β-dicétones éthyléniques.Bull. Soc. Chim. Fr. pp. 288–298.

  • Georgian, V., Harrisson, R., andGubisch, N. 1959. A new chemical desulfurization method.J. Am. Chem. Soc. 81:5834–5835.

    Google Scholar 

  • Kaissling, K.E., andThorson, J. 1980. pp. 261–282,in D.B. Satelle, et al. (eds.) Receptors for Neurotransmitters, Hormones and Pheromones in Insects. Elsevier/North Holland Biomedical Press.

  • König, W.A., Benecke, I., andBretting, H. 1981. Gaschromatographische Trennung enantiomerer Kohlenhydrate an einer neuen chiralen stationären Phase.Angew. Chem. 93:688–690.

    Google Scholar 

  • Kubo, I., Matsumoto, T., andWagner, D.L. 1985. Isolation and structure of hepialone; principle component from male sex scales of (H. californiens (Lepidoptera).Tetrahedron Lett. 26:563–566.

    Google Scholar 

  • Mallet, J. 1984. Sex roles in the ghost mothHepialus humuli (L.) and a review of mating in the Hepialidae (Lepidoptera).Zool. J. Linn. Soc. 79:67–82.

    Google Scholar 

  • Mori, K., andKisida, H. 1986. Synthesis of both enantiomers of the heterocyclic pheromones isolated from the male swift mothH. hectaL.Tetrahedron 42:5281–5290.

    Google Scholar 

  • Rice, K.C. andDyer, J.R. 1975. A practical synthesis of 2,3-dimethylfuran and an efficient stereoselective preparation of (Z)-3-methyl-2-penten-1,4-diol.J. Heterocycl. Chem. 12:1325–1326.

    Google Scholar 

  • Schneider, D. 1984. Pheromone biology of the Lepidoptera: overview, some recent findings and some generalizations, pp. 301–313,in L. Bolis, R.D. Keynes, and S.H.P. Maddrell (eds.). Comparative Physiology of Sensory Systems. Cambridge University Press, Cambridge, U.K.

    Google Scholar 

  • Schurig, V., andWistuba, D. 1984. Analytical enantiomer separation of aliphatic diols as boronates and acetals by complexation gas chromatography.Tetrahedron Lett. 25:5633–5636.

    Google Scholar 

  • Sinnwell, V., Schulz, S., Francke, W., Kittmann, R., andSchneider, D. 1985. Identification of pheromones from the male swift mothHepialus hectaL.Tetrahedron Lett. 26:1707–1710.

    Google Scholar 

  • Turner, J.R.G. 1976. Sexual behaviour: female swift moth is not the aggressive partner.Anim. Behav. 24:188–190.

    Google Scholar 

  • Turner, J.R.G. 1988. Sex, leks and fechts in swift mothsHepialus (Lepidoptera, Hepialidae): Evidence for the hot shot moth.Entomologist 102:90–95.

    Google Scholar 

  • Wunderer, H., Hansen, K., Bell, T.W., Schneider, D., andMeinwald, J. 1985. Sex pheromones of two Asian moths (Creatonotos tansiens, C. gangis, Lepidoptera-Arctiidae): Behavior, morphology, chemistry and electrophysiology.Exp. Biol. 46:11–27.

    Google Scholar 

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Schulz, S., Francke, W., König, W.A. et al. Male pheromone of swift moth,Hepialus hecta L. (Lepidoptera: Hepialidae). J Chem Ecol 16, 3511–3521 (1990). https://doi.org/10.1007/BF00982114

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