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Journal of Chemical Ecology

, Volume 41, Issue 5, pp 441–445 | Cite as

(Z)-13-Hexadecenyl Acetate: a Novel Moth Sex Pheromone Component from Herpetogramma submarginale (Lepidoptera: Crambidae)

  • Qi Yan
  • Kento Kuriyama
  • Keisuke Nishikawa
  • Satoru Tominaga
  • Haruki Tatsuta
  • Tetsu Ando
  • Hideshi Naka
Rapid Communication

Abstract

The sex pheromone of Herpetogramma submarginale (Swinhoe) was studied by gas chromatography (GC) with electroantennographic detection and GC coupled with mass spectrometry. Two pheromone candidates detected in the gland extracts of females were identified as (Z)-13-hexadecenyl acetate (Z13-16:OAc) and (E)-13-hexadecenyl acetate (E13-16:OAc) in a ratio of 87:13 by mass spectral analysis of the natural pheromone components and their dimethyldisulfide adducts. In field tests, Z13-16:OAc alone attracted H. submarginale males and caught significantly more males than live virgin females. Addition of E13-16:OAc did not enhance the attractiveness of Z13-16:OAc. Derivatives of Z13-16:OAc also were tested as potential pheromone components. Addition of (Z)-13-hexadecen-1-ol significantly reduced the number of males captured, and (Z)-13-hexadecenal had no effect on the attractiveness of the lure. These results suggest that the female-produced sex pheromone of H. submarginale is Z13-16:OAc. This hexadecenyl acetate is a novel moth sex pheromone component.

Keywords

Insect pheromone Pyraloidea Spilomelinini Leaf roller Prezygotic isolation 

Notes

Acknowledgments

We thank Mr. Soki Kubota, Mses. Suzuka Yamanishi, Aguri Fujino, and students of the Lab. Applied Entomology in Faculty of Agriculture, Tottori University for help rearing H. submarginale larvae and adults. We also thank Dr. Takeshi Fujii in University of Tokyo, Prof. Masaaki Azuma, and Ms. Mariya Maruyama in Tottori University for supplying relevant information. This work was supported in part by a grant-aid for scientific research from the Ministry of Education, Culture, Sports, Science, and Technology (MEXT) of Japan [KAKENHI, Grant-in-Aid for Scientific Research (C) No. 25450071].

References

  1. Ando T (2014) Internet database: http://www.tuat.ac.jp/~antetsu/LepiPheroList.htm. Accessed 01 Jan 2015
  2. Ando T, Yamakawa R (2011) Analyses of lepidopteran sex pheromones by mass spectrometry. Trends Anal Chem 30:990–1002CrossRefGoogle Scholar
  3. Baker TC (2008) Balanced olfactory antagonism as a concept for understanding evolutionary shifts in moth sex pheromone system. J Chem Ecol 34:971–981CrossRefPubMedGoogle Scholar
  4. Buser HR, Arn H, Guerin P, Rauscher S (1983) Determination of double bond position in mono-unsaturated acetates by mass spectrometry of dimethyl disulfide adducts. Anal Chem 55:818–822CrossRefGoogle Scholar
  5. Fujii T, Ito K, Tatematsu M, Shimada T, Katsuma S, Ishikawa Y (2011) Sex pheromone desaturase functioning in a primitive Ostrinia moth is cryptically conserved in congeners’ genomes. Proc Natl Acad Sci USA 108:7102–7106CrossRefPubMedCentralPubMedGoogle Scholar
  6. Gibb AR, Suckling DM, El-Sayed AM, Bohman B, Unelius CR, Dymock JJ, Larsen ML, Willoughby BE (2007) (11Z,13E)-Hexadecadien-1-yl acetate: sex pheromone of the grass webworm Herpetogramma licarsisalis–Identification, synthesis, and field bioassays. J Chem Ecol 33:839–847Google Scholar
  7. Jain SC, Dussourd DE, Conner WE, Eisner T, Guerrero A, Meinwald J (1983) Polyene pheromone components from an Arctiid moth (Utetheisa ornatrix): characterization and synthesis. J Org Chem 48:2266–2270CrossRefGoogle Scholar
  8. Lassance JM, Groot AT, Liénard MA, Antony B, Borgwardt C, Andersson F, Hedenström E, Heckel DG, Löfstedt C (2010) Allelic variation in a fatty-acyl reductase gene causes divergence in moth sex pheromones. Nature 466:486–489CrossRefPubMedGoogle Scholar
  9. Liu W, Rooney AP, Xue B, Roelofs WL (2004) Desaturases from the spotted fireworm moth (Choristoneura parallela) shed light on the evolutionary origins of novel moth sex pheromone desaturases. Gene 342:303–311CrossRefPubMedGoogle Scholar
  10. McElfresh JS, Millar JG, Rubinoff D (2001) (E4, Z9)-Tetradecadienal, a sex pheromone for three north American moth species in the genus Saturnia. J Chem Ecol 27:791–806Google Scholar
  11. R Development Core Team (2014) R: a language and environment for statistical computing. R Foundation for Statistical Computing, Vienna, http://www.R-project.org Google Scholar
  12. Yamanaka A (2013) Pyraustinae. In: Nasu Y et al (eds) The standard of moths in Japan IV. Gakken, Tokyo, pp 415–478 (in Japanese) Google Scholar

Copyright information

© Springer Science+Business Media New York 2015

Authors and Affiliations

  • Qi Yan
    • 1
  • Kento Kuriyama
    • 2
  • Keisuke Nishikawa
    • 2
  • Satoru Tominaga
    • 3
  • Haruki Tatsuta
    • 2
  • Tetsu Ando
    • 1
  • Hideshi Naka
    • 4
  1. 1.Graduate School of Bio-Applications and Systems EngineeringTokyo University of Agriculture and TechnologyKoganeiJapan
  2. 2.Laboratory of Entomology, Department of Ecology and Environmental Sciences, Faculty of AgricultureUniversity of the RyukyusNishiharaJapan
  3. 3.YaeseJapan
  4. 4.Laboratory of Applied Entomology, Faculty of AgricultureTottori UniversityTottoriJapan

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