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A Tetraene Aldehyde as the Major Sex Pheromone Component of the Promethea Moth (Callosamia promethea (Drury))

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Abstract

The promethea moth Callosamia promethea is one of three species of silkmoths from the genus Callosamia that occur in North America. Cross attraction of males to heterospecific calling females has been observed in the field, and hybrid progeny have been produced by pairing heterospecifics in captivity. These observations suggest that all three species share or have considerable overlap in the sex attractant pheromones produced by females, so that other prezygotic isolating mechanisms, such as diel differences in reproductive activity, limit hybridization in the field. Coupled gas chromatography-electroantennogram detection and gas chromatography- mass-spectrometry analyses of extracts of volatiles collected from female promethea moths supported the identification of (4E,6E,11Z,13Z)-hexadeca-4,6,11,13-tetraenal [(4E,6E,11Z,13Z)-16:Ald] as the compound in extracts that elicited the largest responses from antennae of males. The identification was confirmed by non-selective synthesis of several isomers as analytical standards, and stereoselective synthesis of (4E,6E,11Z,13Z)-16:Ald for testing in field trials. Male moths were strongly attracted to synthetic (4E,6E,11Z,13Z)-16:Ald, suggesting that this compound is the major and possibly the only component of the sex pheromone of these large saturniid moths. Based on the cross-attraction of heterospecifics, it is likely that this is also a major pheromone component of the other two North American Callosamia species as well.

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Acknowledgments

We are indebted to the Ministry of Science and Innovation for a FPI fellowship to RG. We also thank Shelby Stamper for assistance with the field trials at the UK Arboretum and North Farm. Financial assistance was provided to JDA by the LSU AgCenter, to KFH by Kentucky Agricultural Experiment Station, to AG by CICYT through project AGL2009-13452-C02-01, and to JGM through Hatch project CA-R*-5181-H.

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Authors and Affiliations

  1. Department of Biological Chemistry and Molecular Modeling, IQAC (CSIC), Jordi Girona 18, Barcelona, 08034, Spain

    Rafael Gago & Angel Guerrero

  2. Department of Entomology, Louisiana State University Agricultural Center, LSU Campus, Baton Rouge, LA, 70803, USA

    Jeremy D. Allison & Jessica McKenney

  3. Great Lakes Forestry Centre, Natural Resources Canada, 1219 Queen Street East, Sault Ste. Marie, Ontario, P6A 2E5, Canada

    Jeremy D. Allison

  4. Department of Entomology, University of California, Riverside, CA, 92521, USA

    J. Steven McElfresh & Jocelyn G. Millar

  5. Department of Entomology, University of Kentucky, Lexington, KY, 40546, USA

    Kenneth F. Haynes

Authors
  1. Rafael Gago
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  2. Jeremy D. Allison
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  3. J. Steven McElfresh
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  4. Kenneth F. Haynes
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  5. Jessica McKenney
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  6. Angel Guerrero
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  7. Jocelyn G. Millar
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Corresponding author

Correspondence to Jocelyn G. Millar.

Electronic supplementary material

Supporting information includes descriptions of the syntheses of isomeric mixtures of (4E,6E,11Z/E,13E)-hexadeca-4,6,11,13-tetraenal (20a), (4E,6E,11E/Z,13Z)-hexadeca-4,6,11,13-tetraenal (20b) and (4E,6E,11E,13Z/E)- hexadeca-4,6,11,13-tetraen-1-ol (23), and a video showing the responses of male moths to pheromone lures.

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Close range response of the Promethea moth, Callosamia promethea, to 100 micrograms of E4,E6,Z11,Z13-16:Ald on a red rubber septum, May 2013, Lexington, Kentucky, USA. (M4V 6.46 mb)

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Gago, R., Allison, J.D., McElfresh, J.S. et al. A Tetraene Aldehyde as the Major Sex Pheromone Component of the Promethea Moth (Callosamia promethea (Drury)). J Chem Ecol 39, 1263–1272 (2013). https://doi.org/10.1007/s10886-013-0349-1

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  • DOI: https://doi.org/10.1007/s10886-013-0349-1

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