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Biosynthesis and PBAN-Regulated Transport of Pheromone Polyenes in the Winter Moth, Operophtera brumata

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Abstract

The trienoic and tetraenoic polyenes, (3Z,6Z,9Z)-3,6,9-nonadecatriene, (3Z,6Z,9Z)-3,6,9-henicosatriene, and (3Z,6Z,9Z)-1,3,6,9-henicosatetraene were found in the abdominal cuticle and pheromone gland of the winter moth Operophtera brumata L. (Lepidoptera: Geometridae), in addition to the previously identified single component sex pheromone (3Z,6Z,9Z)-1,3,6,9-nonadecatetraene. The pheromone biosynthesis activating neuropeptide (PBAN) is involved in the regulation of polyene transport from abdominal cuticle to the pheromone gland. In vivo deuterium labeling experiments showed that (11Z,14Z,17Z)-11,14,17-icosatrienoic acid, the malonate elongation product of linolenic acid, (9Z,12Z,15Z)-9,12,15-octadecatrienoic acid, is used to produce (3Z,6Z,9Z)-3,6,9-nonadecatriene and (3Z,6Z,9Z)-1,3,6,9-nonadecatetraene.

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Acknowledgments

We thank Dr. Wittko Francke, Institute of Organic Chemistry, University of Hamburg, for providing the triene and tetraene reference compounds; Dr. Jocelyn G. Millar, Department of Entomology, University of California Riverside, for his long-term support and discussion on this study; and Dr. Richard Newcomb, School of Biological Sciences, University of Auckland, for comments on the manuscript. This study was supported by grants from the Swedish Research Council (VR) and SIDA-Sarec to CL.

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Authors and Affiliations

  1. Department of Biology, Lund University, Lund, Sweden

    Hong-Lei Wang & Christer Löfstedt

  2. Institute of Zoology, Chinese Academy of Sciences, Beijing, China

    Cheng-Hua Zhao

  3. Department of Zoology, Plant Protection Institute, Centre for Agricultural Research, Hungarian Academy of Science, Budapest, Hungary

    Gabor Szöcs

  4. Institute of Organic Chemistry, Technische Universtät Braunschweig, Braunschweig, Germany

    Satya Prabhakar Chinta & Stefan Schulz

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  1. Hong-Lei Wang
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  2. Cheng-Hua Zhao
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  3. Gabor Szöcs
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  4. Satya Prabhakar Chinta
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  5. Stefan Schulz
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  6. Christer Löfstedt
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Correspondence to Hong-Lei Wang.

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Deceased May 1st 2011 in the course of this study. The other authors dedicate the publication to the memory of Prof. Cheng-Hua Zhao and his contributions to chemical ecology.

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Wang, HL., Zhao, CH., Szöcs, G. et al. Biosynthesis and PBAN-Regulated Transport of Pheromone Polyenes in the Winter Moth, Operophtera brumata . J Chem Ecol 39, 790–796 (2013). https://doi.org/10.1007/s10886-013-0292-1

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  • DOI: https://doi.org/10.1007/s10886-013-0292-1

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