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Anatomical localization and stereoisomeric composition of Tribolium castaneum aggregation pheromones

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Abstract

We report that the abdominal epidermis and associated tissues are the predominant sources of male-produced pheromones in the red flour beetle, Tribolium castaneum and, for the first time, describe the stereoisomeric composition of the natural blend of isomers of the aggregation pheromone 4,8-dimethyldecanal (DMD) in this important pest species. Quantitative analyses via gas chromatography–mass spectrometry showed that the average amount of DMD released daily by single feeding males of T. castaneum was 878 ± 72 ng (SE). Analysis of different body parts identified the abdominal epidermis as the major source of aggregation pheromone; the thorax was a minor source, while no DMD was detectable in the head. No internal organs or obvious male-specific glands were associated with pheromone deposition. Complete separation of all four stereoisomers of DMD was achieved following oxidation to the corresponding acid, derivatization with (1R, 2R)- and (1S, 2S)-2-(anthracene-2,3-dicarboximido)cyclohexanol to diastereomeric esters, and their separation on reversed-phase high-performance liquid chromatography at −54°C. Analysis of the hexane eluate from Porapak-Q-collected volatiles from feeding males revealed the presence of all four isomers (4R,8R)/(4R,8S)/(4S,8R)/(4S,8S) at a ratio of approximately 4:4:1:1. A walking orientation bioassay in a wind tunnel with various blends of the four synthetic isomers further indicated that the attractive potency of the reconstituted natural blend of 4:4:1:1 was equivalent to that of the natural pheromone and greater than that of the 1:1 blend of (4R,8R)/(4R,8S) used in commercial lures.

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Acknowledgments

The authors thank Alain VanRyckeghem, Insects Limited, Westfield, IN, for providing an authentic standard of DMD as a GC standard, and David Hagstrum, Lee Cohnstaedt, and Jim Throne for constructive reviews. Partial funding for this research came from the Kansas Agricultural Experiment Station and the USDA Risk Avoidance and Mitigation Program. Mention of trade names or commercial products in this publication is solely for the purpose of providing specific information and does not imply recommendation or endorsement by the US Department of Agriculture or Kansas State University. USDA is an equal-opportunity provider and employer.

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Authors and Affiliations

  1. Department of Entomology, Kansas State University, Manhattan, KS, 66506, USA

    Yujie Lu, Yoonseong Park, Michael J. Aikins & Thomas W. Phillips

  2. Food and Grain College, Henan University of Technology, Zhengzhou, Henan Province, 450052, China

    Yujie Lu

  3. Agricultural Research Service, Center for Grain and Animal Health Research, US Department of Agriculture, 1515 College Avenue, Manhattan, KS, 66502, USA

    Richard W. Beeman & James F. Campbell

  4. Photosensitive Materials Research Center, Toyo Gosei Co., Ltd, 4-2-1 Wakahagi, Inzai-shi, Chiba, 270-1609, Japan

    Kenji Mori

  5. Shokei Gakuin University, 4-10-1 Yurigaoka, Natori-shi, Miyagi, 981-1295, Japan

    Kazuaki Akasaka

  6. Technical Research Institute, T. Hasegawa Co., Ltd., 29-7 Kariyado, Nakahara-ku, Kawasaki-shi, Kanagawa, 211-0022, Japan

    Shigeyuki Tamogami

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  1. Yujie Lu
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  2. Richard W. Beeman
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  3. James F. Campbell
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  4. Yoonseong Park
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  6. Kenji Mori
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  7. Kazuaki Akasaka
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  8. Shigeyuki Tamogami
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  9. Thomas W. Phillips
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Correspondence to Thomas W. Phillips.

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Communicated by: Sven Thatje

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Lu, Y., Beeman, R.W., Campbell, J.F. et al. Anatomical localization and stereoisomeric composition of Tribolium castaneum aggregation pheromones. Naturwissenschaften 98, 755 (2011). https://doi.org/10.1007/s00114-011-0824-x

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  • DOI: https://doi.org/10.1007/s00114-011-0824-x

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