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Alkyldimethylpyrazines in the Defensive Spray of Phyllium westwoodii: A First for Order Phasmatodea

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Abstract

Phyllium westwoodii is a phasmid insect (Order Phasmatodea) belonging to the Family Phylliidae (leaf insects). These rather large and ornate creatures are known for their morphological resemblance to plant leaves for camouflage. Pyrazines are a common class of compounds used or produced by a wide variety of organisms, even humans. When an individual of P. westwoodii is disturbed, it sprays an opaque liquid from a pair of prothoracic glands, which are utilized by other phasmid species for defense. The current study has found that this liquid contains glucose and a mixture of 3-isobutyl-2,5-dimethylpyrazine, 2,5-dimethyl-3-(2-methylbutyl)pyrazine, and 2,5-dimethyl-3-(3-methylbutyl)pyrazine. This is the first report of pyrazines found in the defensive gland spray of phasmid insects, and the first chemical analysis of glandular material from family Phylliidae.

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Acknowledgement

We thank James R. Rocca at the Advanced Magnetic Resonance Imaging and Spectroscopy, University of Florida, for helpful technical assistance on NMR experiments. The GC-MS analysis reported in this study was developed and conducted by Dr. Maria Cristina Dancel of the Mass Spectrometry Facility, Department of Chemistry, University of Florida, who also helped with data interpretation. Funding was provided by NIH P41RR016105, the Human Frontier Science Program (ASE), and the NSF-supported National High Magnetic Field Laboratory, and Scripps Florida (WRR). NMR data were collected in the AMRIS facility in the McKnight Brain Institute of the University of Florida.

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Authors and Affiliations

  1. Department of Biochemistry & Molecular Biology, University of Florida, Gainesville, FL, 32610-0245, USA

    Aaron T. Dossey & Arthur S. Edison

  2. Museo Civico di Storia Naturale di Ferrara, Via De Pisis 24, 44100, Ferrara, Italy

    Marco Gottardo

  3. Department of Chemistry, Scripps Florida, Jupiter, FL, 33458, USA

    John M. Whitaker & William R. Roush

  4. McKnight Brain Institute, University of Florida, Gainesville, FL, 32610, USA

    Arthur S. Edison

  5. National High Magnetic Field Laboratory, University of Florida, Gainesville, USA

    Arthur S. Edison

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  1. Aaron T. Dossey
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  2. Marco Gottardo
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Correspondence to Aaron T. Dossey.

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Supplemental Material 1

S1 EIMS database matching data for natural pyrazines 1, 2, and 3 from Phyllium westwoodii defensive spray; S2–S5) 2D COSY, TOCSY, HSQC, and HMBC spectra of P. westwoodii defensive spray, S6) Alkyl 1H -aromatic 13C expansion of HMBC spectra from synthetic compounds 1, 2, and 3; and S7) A video illustrating the defensive behavior of P. westwoodii. (DOC 2184 kb)

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Dossey, A.T., Gottardo, M., Whitaker, J.M. et al. Alkyldimethylpyrazines in the Defensive Spray of Phyllium westwoodii: A First for Order Phasmatodea. J Chem Ecol 35, 861–870 (2009). https://doi.org/10.1007/s10886-009-9666-9

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