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Defensive Roles of (E)-2-Alkenals and Related Compounds in Heteroptera

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Abstract

We examined whether shared volatiles found in various heteropteran species and developmental stages function to repel predators. The nymphal dorsal abdominal gland secretions of Riptortus pedestris (Heteroptera: Alydidae) and Thasus acutangulus (Heteroptera: Coreidae), and the metathoracic scent gland secretion of Euschistus biformis (Heteroptera: Pentatomidae) adults were identified by gas chromatography/mass spectrometry (GC/MS). (E)-2-Hexenal, 4-oxo-(E)-2-hexenal (4-OHE), and (E)-2-octenal were found in all three species and deemed likely candidates for repelling predators. In addition to (E)-2-alkenals, the adult E. biformis secreted (E)-2-hexenyl acetate, (E)-2-octenyl acetate, and four hydrocarbons. We evaluated the potential predator repellent properties of these compounds and compound blends against a generalist, cosmopolitan insect predator, the Chinese praying mantid (Mantodea: Mantidae: Tenodera aridifolia sinensis). Mantids that experienced (E)-2-hexenal, (E)-2-octenal, and (E)-2-octenyl acetate moved away from the site of interaction, while 4-OHE and (E)-2-hexenyl acetate did not affect mantid behavior. The compound blends did not have additive or synergistic repellency effects on predator behavior. Compound repellency was not related to compound volatility. Instead, the repellent effect is likely related to predator olfaction, and the affinity of each compound to receptors on the antennae. Our results also suggest the repellents might intensify the visual defensive signals of aposematism (T. acutangulus nymphs) and mimicry (R. pedestris nymphs) in heteropteran bugs.

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References

  • Aldlich, J. R., Oliver, J. E., Taghizadeh, T., Ferreira, J. T. B., and Liewehr, D. 1999. Pheromones and colonization: reassessment of the milkweed bug migration model (Heteroptera: Lygaeidae: Lygaeinae). Chemoecology 9:63–71.

    Article  Google Scholar 

  • Aldrich, J. R. 1988. Chemical ecology of the Heteroptera. Annu. Rev. Entomol. 33:211–238.

    Article  Google Scholar 

  • Aldrich, J. R. and Blum, M. S. 1978. Aposematic aggregation of a bug (Hemiptera: Coreidae): The defensive display and formation of aggregations. Biotropica 10:58–61.

    Article  Google Scholar 

  • Aldrich, J. R., Waite, G. K., Moore, C., Payne, J. A., Lusby, W. R., and Kochansky, J. P. 1993. Male-specific volatiles from Nearctic and Australasian true bugs (Heteroptera: Coreidae and Alydidae). J. Chem. Ecol. 19:2767–2781.

    Article  CAS  Google Scholar 

  • Aldrich, J. R., Rosi, M. C., and Bin, F. 1995. Behavioral correlates for minor volatile compounds from stink bugs (Heteroptera: Pentatomidae). J. Chem. Ecol. 21:1907–1920.

    Article  CAS  Google Scholar 

  • Blum, M. S. 1961. The presence of 2-hexenal in the scent gland of the pentatomid Brochymena quadripustulata. Ann. Entomol. Soc. Am. 54:410–412.

    CAS  Google Scholar 

  • Borges, M. and Aldrich, J. R. 1992. Instar-specific defensive secretions of stink bugs (Heteroptera: Pentatomidae). Experientia 48:893–896.

    Article  CAS  Google Scholar 

  • Bowers, M. D. 1993. Aposematic caterpillars: Life-styles of the warningly colored and unpalatable, pp. 331–371, in N. E. Stamp and T. M. Casey (eds.), Caterpillars: Ecological and Evolutionary Constraints on Foraging. Chapman & Hall, New York, NY.

    Google Scholar 

  • Brailovsky, H., Schaefer, C. W., Barrera, E., and Packauskas, R. J. 1994. A revision of the genus Thasus (Hemiptera: Coreidae: Coreinae: Nematopodini). J. N.Y Entomol. Soc. 102:318–343.

    Google Scholar 

  • Chapman, R. F. 1998. The Insects. Structure and Function, 4th ed. Cambridge University Press, Cambridge.

    Book  Google Scholar 

  • Eisner, T. 1970. Chemical defense against predation in arthropods, pp. 157–217, in E. Sondheimer and J. B. Simeone (eds.), Chemical Ecology. Academic, New York, NY.

    Google Scholar 

  • Eisner, T., Eisner, M., and Siegler, M. 2005. Secret Weapons. Defenses of Insects, Spiders, Scorpions, and Other Many-Legged Creatures. Belknap Press of Harvard University Press, Cambridge.

    Google Scholar 

  • Gunawardena, N. E. and Bandumathie, M. K. 1993. Defensive secretion of rice bug, Leptocorisa oratorius Fabricius, (Hemiptera: Coreidae): A unique chemical combination and its toxic, repellent, and alarm properties. J. Chem. Ecol. 19:851–861.

    Article  CAS  Google Scholar 

  • Gunawardena, N. E. and Herath, H. M. W. K. B. 1991. Significance of medium chain n-alkanes as accompanying compounds in heteropteran defensive secretions: An investigation based on the defensive secretion of Coridius janus. J. Chem. Ecol. 17:2449–2458.

    Article  CAS  Google Scholar 

  • Hebets, E. A. and Papaj, D. R. 2005. Complex signal function: developing a framework of testable hypotheses. Behav. Ecol. Sociobiol. 57:197–214.

    Article  Google Scholar 

  • Kasai, H., Maekawa, M., Kawai, K., Hachisuka, K., Takahashi, Y., Nakamura, H., Sawa, R., Matsui, S., and Matsuda, T. 2005. 4-Oxo-2-hexenal, a mutagen formed by ω-3 fat peroxidation, causes DNA adduct formation in mouse organs. Ind. Health 43:699–701.

    Article  PubMed  CAS  Google Scholar 

  • Kikuhara, Y. 2005. The Japanese species of the genus Riptortus (Heteroptera: Alydidae) with description of a new species. Jpn. J. Syst. Entomol. 11:229–311.

    Google Scholar 

  • Krall, B. K., Bartelt, R. J., Lewis, C. J., and Whiteman, D. W. 1999. Chemical defense in the stink bug Cosmopepla bimaculata. J. Chem. Ecol. 25:2477–2494.

    Article  CAS  Google Scholar 

  • Leal, W. S., Panizzi, A. R., and Niva, C. C. 1994. Alarm pheromone system of leaf-footed bug Leptoglossus zonatus (Heteroptera: Coreidae). J. Chem. Ecol. 20:1209–1216.

    Article  CAS  Google Scholar 

  • Leal, W. S., Higuchi, H., Mizutani, N., Nakamori, H., Kadosawa, T., and Ono, M. 1995. Multifunctional communication in Riptortus clavatus (Heteroptera: Alydidae): Conspecific nymphs and egg parasitoid Ooencyrtus nezarae use the same adult attractant pheromone as chemical cue. J. Chem. Ecol. 21:973–985.

    Article  CAS  Google Scholar 

  • Marques, F. A., Wendeler, E. P., Sales Maia, B. H. L. N., Ventura, M. U., and Arruda-Gatti, I. C. 2007. Identification of defensive compounds in metathoracic glands of adults of the stink bug Dichelops melacanthus (Hemiptera: Pentatomidae). J. Braz. Chem. Soc. 18:1242–1246.

    Article  CAS  Google Scholar 

  • Millar, J. G. 2005. Pheromones of true bugs. Top. Curr. Chem. 240:37–84.

    CAS  Google Scholar 

  • Moraes, M. C. B., Pareja, M., Laumann, R. A., and Borges, M. 2008. The chemical volatiles (semiochemicals) produced by Neotropical stink bugs (Hemiptera: Pentatomidae). Neotrop. Entomol. 37:489–505.

    Article  PubMed  CAS  Google Scholar 

  • Moreira, J. A. and Millar, J. G. 2005. Short and simple synthesis of 4-oxo-(E)-2-hexenal and homologs: Pheromone components and defensive compounds of Hemiptera. J. Chem. Ecol. 31:965–968.

    Article  PubMed  CAS  Google Scholar 

  • Yasunaga, T., Takai, M., Yamashita, I, Kawamura, M., and Kawasawa, T. 1993. A Field Guide to Japanese Bugs. Zenkoku Noson Kyoiku Kyokai, Tokyo. (in Japanese).

  • Pasteels, J. M., Grégoire, J.-C., and Rowell-Rahier, M. 1983. The chemical ecology of defense in arthropods. Annu. Rev. Entomol. 28:263–289.

    Article  CAS  Google Scholar 

  • Prudic, K. L., Skemp, A. K., and Papaj, D. R. 2007. Aposematic coloration, luminance contrast, and the benefits of conspicuousness. Behav. Ecol. 18:41–46.

    Article  Google Scholar 

  • Prudic, K. L., Noge, K., and Becerra, J. X. 2008. Adults and nymphs do not smell the same: the different defensive compounds of the giant mesquite bug (Thasus neocalifornicus: Coreidae). J. Chem. Ecol. 34:734–741.

    Article  PubMed  CAS  Google Scholar 

  • Rowe, C. 1999. Receiver physiology and the evolution of multicomponent signals. Anim. Behav. 58:921–931.

    Article  PubMed  Google Scholar 

  • Ruxton, G. D., Sherratt, T. N., and Speed, M. P. 2004. Avoiding Attack: The Evolutionary Ecology of Crypsis, Warning Signals and Mimicry. Oxford University Press, Oxford.

    Google Scholar 

  • Sakakura, A., Kawajiri, K., Ohkubo, T., Kosugi, Y., and Ishihara, K. 2007. Widely useful DMAP-catalyzed esterification under auxiliary base- and solvent-free conditions. J. Am. Chem. Soc. 129:14775–14779.

    Article  PubMed  CAS  Google Scholar 

  • Sas Institute Inc. 2003. JMP 5.1, Cary, NC.

  • Schaefer, C. W. and Packauskas, R. J. 1997. Notes on the genus Thasus (Hemiptera: Coreidae). J. N.Y Entomol. Soc. 105:206–214.

    Google Scholar 

  • Todd, J. L. and Baker, T. C. 1983. Response of single antennal neurons of female cabbage loopers to behaviorally active attractants. Naturwissenschaften 80:183–186.

    Article  Google Scholar 

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Acknowledgments

We thank Carl W. Schaefer (University of Connecticut), Carl A. Olson, Sarai Olivier (University of Arizona) for help with insect identification, Alexander L. Wild (University of Arizona) for photographs of the insects, and Gabriela and D. Lawrence Venable (University of Arizona) for insect-collecting assistance. We are also grateful to Neil Jacobsen and Guangxin Lin (University of Arizona) for acquiring the NMR spectra. This work was funded by a seed grant from the BIO5 institute, University of Arizona to J. X. B. The GC–MS, a PerkinElmer Turbo Mass, partly used in this study is a commonly shared instrument at Akita Prefectural University.

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Author notes

  1. Koji Noge

    Present address: Department of Biological Production, Akita Prefectural University, Akita, 010-0195, Japan

  2. Kathleen L. Prudic

    Present address: Department of Ecology and Evolutionary Biology, Yale University, New Haven, CT, 06520, USA

Authors and Affiliations

  1. Department of Entomology, University of Arizona, Tucson, AZ, 85721, USA

    Koji Noge & Kathleen L. Prudic

  2. Department of Biosphere 2, University of Arizona, Tucson, AZ, 85721, USA

    Judith X. Becerra

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  1. Koji Noge
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  2. Kathleen L. Prudic
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Correspondence to Koji Noge.

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Noge, K., Prudic, K.L. & Becerra, J.X. Defensive Roles of (E)-2-Alkenals and Related Compounds in Heteroptera. J Chem Ecol 38, 1050–1056 (2012). https://doi.org/10.1007/s10886-012-0166-y

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