Journal of Chemical Ecology

, Volume 11, Issue 5, pp 643–648

Absolute configuration of mosquito oviposition attractant pheromone, 6-acetoxy-5-hexadecanolide

  • B. R. Laurence
  • K. Mori
  • T. Otsuka
  • J. A. Pickett
  • L. J. Wadhams
Article

Abstract

6-Acetoxy-5-hexadecanolide (Ia) in the oviposition attractant pheromone released from egg apical droplets of the mosquitoCulex pipiens fatigans Wied. is shown to be the (−)-(5R,6S)- enantiomer. Identification was by chromatography of the 6-trifluoroacetoxy derivatives of the natural pheromone and of the synthetic (−)-(5R,6S)- (Ib) and (+)-(5S,6R)- (IIb) enantiomers on a capillary column having a chiral stationary phase comprising a derivative of (1S,3S)-chrysanthemic acid. The synthetic (−)-(5R,6S)- enantiomer (Ia) attracted oviposition of four fold more mosquito egg rafts than the control (P < 0.01) whereas for the (5S,6R)- enantiomer (IIa) there was no statistically significant oviposition attraction.

Key words

Mosquito Culex pipiens fatigans Diptera Culicidae oviposition attractant pheromone chiral chromatography acetoxyhexadecanolide 

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References

  1. Bruno, D.W., andLaurence, B.R. 1979. The influence of the apical droplet ofCulex egg rafts on oviposition ofCulex pipiens fatigans (Diptera: Culicidae).J. Med. Entomol. 16:300–305.Google Scholar
  2. König, W.A. 1982. Separation of enantiomers by capillary gas chromatography with chiral stationary phases.J. High-Resolution Chromatogr. Column Chromatogr. 5:588–595.Google Scholar
  3. König, W.A., Francke, W., andBenecke, I. 1982. Gas Chromatographic enantiomer separation of chiral alcohols.J. Chromatogr. 239:227–231.Google Scholar
  4. Laurence, B.R., andPickett, J.A. 1982.erythro-6-Acetxoy-5-hexadecanolide, the major component of a mosquito oviposition attractant pheromone.J. Chem. Soc., Chem. Commun. 59–60.Google Scholar
  5. Laurence, B.R., andPickett, J.A. 1985. An oviposition attractant-pheromone inCulex pipiens fatigans Wisch. (Diptera: Culicidae).Bull. Ent. Res. (in press).Google Scholar
  6. Mori, K., andOtsuka, T. 1983. Synthesis of both the enantiomers oferythro-6-acetoxy-5-hexad- ecanolide, the major component of a mosquito oviposition attractant pheromone.Tetrahedron 39:3267–3269.Google Scholar
  7. Oi, N., Kitahara, H., andDoi, T. 1983. Gas Chromatographic separation of chrysanthemic acid ester enantiomers on a novel chiral stationary phase.J. Chromatogr. 254:282–284.Google Scholar

Copyright information

© Plenum Publishing Corporation 1985

Authors and Affiliations

  • B. R. Laurence
    • 1
  • K. Mori
    • 2
  • T. Otsuka
    • 2
  • J. A. Pickett
    • 3
  • L. J. Wadhams
    • 3
  1. 1.London School of Hygiene and Tropical MedicineLondonUK
  2. 2.Department of Agricultural ChemistryThe University of TokyoTokyoJapan
  3. 3.Rothamsted Experimental StationHarpendenUK

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