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Male Phyllotreta striolata (F.) Produce an Aggregation Pheromone: Identification of Male-specific compounds and Interaction with Host Plant Volatiles

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Abstract

The chrysomelid beetle Phyllotreta striolata is an important pest of Brassicaceae in Southeast Asia and North America. Here, we identified the aggregation pheromone of a population of P. striolata from Taiwan, and host plant volatiles that interact with the pheromone. Volatiles emitted by feeding male P. striolata attracted males and females in the field. Headspace volatile analyses revealed that six sesquiterpenes were emitted specifically by feeding males. Only one of these, however, elicited an electrophysiological response from antennae of both sexes. A number of host plant volatiles, e.g., 1-hexanol, (Z)-3-hexen-1-ol, and the glucosinolate hydrolysis products allyl isothiocyanate (AITC), 3-butenyl isothiocyanate, and 4-pentenyl isothiocyanate also elicited clear responses from the antenna. The active male-specific compound was identified as (+)-(6R,7S)-himachala-9,11-diene by chiral stationary phase gas-chromatography with coupled mass spectrometry, and by comparison with reference samples from Abies nordmanniana, which is known to produce the corresponding enantiomer. The pheromone compound was synthesized starting from (–)-α-himachalene isolated from Cedrus atlantica. Under field conditions, the activity of the synthetic pheromone required concomitant presence of the host plant volatile allyl isothiocyanate. However, both synthetic (+)-(6R,7S)-himachala-9,11-diene alone and in combination with AITC were attractive in a two-choice laboratory assay devoid of other natural olfactory stimuli. We hypothesize that P. striolata adults respond to the pheromone only if specific host volatiles are present. In the same laboratory set up, more beetles were attracted by feeding males than by the synthetic stimuli. Thus, further research will be necessary to reveal the components of a more complex blend of host or male-produced semiochemicals that might enhance trap attractiveness in the field.

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Acknowledgments

We thank the Gesellschaft für Technische Zusammenarbeit (GTZ) and the Max Planck Gesellschaft for funding. FB was supported by a grant from FAZIT-Stiftung, Germany. The authors thank Stefan Garms for advice and support regarding the identification of sesquiterpenes and for providing the Scapania undulata extract, Lin Mei-ying and the staff of Entomology unit at AVRDC-The World Vegetable Center for supporting field experiments, and Daniel Veit, head of the workshop at ICE Jena for his continued support and advice with experimental equipment. Hervé Mosimann is indebted to Xavier Garnier for technical skill in performing large scale distillation. Jiří Svoboda thanks his father, Prof. Jiří Svoboda, for help with the catalytic hydrogenation of (–)-α-himachalene.

Author contributions

F.B. designed and performed experiments, analyzed natural extracts and synthetic products, and prepared the manuscript; I.M., C.U., R.S., and C.B. designed experiments, provided experimental facilities, insects, and acquired GTZ funding; C.V. and H.M. performed isolation of the precursor and reference substances and designed the synthetis pathway of A; J.S. and W.B. performed the synthesis of A and confirmed the structure of the product; A.R. and B.S.H. designed experiments and prepared the manuscript; MPG funding was provided though B.S.H.

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Authors and Affiliations

  1. Department Urban Plant Ecophysiology, Humboldt-Universität zu Berlin, Lentzeallee 75, 14195, Berlin, Germany

    Franziska Beran & Christian Ulrichs

  2. Department Phytomedicine, Humboldt-Universität zu Berlin, Lentzeallee 75, 14195, Berlin, Germany

    Franziska Beran

  3. Institute of Vegetable and Ornamental Crops Grossbeeren/Erfurt e.V., Theodor-Echtermeyer-Weg 1, 14979, Grossbeeren, Germany

    Inga Mewis

  4. AVRDC-The World Vegetable Center, Entomology Unit, 60 Yi-min Liao, Shanhua, 74151, Tainan, Taiwan

    Ramasamy Srinivasan

  5. Department of Bioorganic Chemistry, Max Planck Institute for Chemical Ecology, Hans-Knöll-Straße 8, 07745, Jena, Germany

    Jiří Svoboda & Wilhelm Boland

  6. Firmenich SA, Route des Jeunes 1, Genève 8, CH-1211, Switzerland

    Christian Vial & Hervé Mosimann

  7. Department Phytomedicine, Humboldt-Universität zu Berlin, Lentzeallee 55–57, 14195, Berlin, Germany

    Carmen Büttner

  8. Department of Evolutionary Neuroethology, Max Planck Institute for Chemical Ecology, Hans-Knöll-Straße 8, 07745, Jena, Germany

    Bill S. Hansson & Andreas Reinecke

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  1. Franziska Beran
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Beran, F., Mewis, I., Srinivasan, R. et al. Male Phyllotreta striolata (F.) Produce an Aggregation Pheromone: Identification of Male-specific compounds and Interaction with Host Plant Volatiles. J Chem Ecol 37, 85–97 (2011). https://doi.org/10.1007/s10886-010-9899-7

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