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J Chem Ecol

Title:		Evidence that Cerambycid Beetles Mimic Vespid Wasps in Odor as well as Appearance
Author(s):		Mitchell RF; Curkovic T; Mongold-Diers JA; Neuteboom L; Galbrecht HM; Troger A; Bergmann J; Francke W; Hanks LM;
Address:		"Department of Entomology, University of Illinois at Urbana-Champaign, Urbana, IL, 61801, USA. mitchellr@uwosh.edu. Department of Biology, University of Wisconsin Oshkosh, 142 Halsey Science Center, 800 Algoma Blvd., Oshkosh, WI, 54901, USA. mitchellr@uwosh.edu. Departamento de Sanidad Vegetal, Universidad de Chile, PO Box 1004, Santiago, Chile. Department of Entomology, University of Illinois at Urbana-Champaign, Urbana, IL, 61801, USA. Institut fur Organische Chemie, Universitat Hamburg, 20146, Hamburg, Germany. Instituto de Quimica, Pontificia Universidad Catolica de Valparaiso, Valparaiso, Chile"
Journal Title:		J Chem Ecol
Year:		2017
Volume:		20161219
Issue:		1
Page Number:		75 - 83
DOI:		10.1007/s10886-016-0800-1
ISSN/ISBN:		1573-1561 (Electronic) 0098-0331 (Print) 0098-0331 (Linking)
Abstract:		"We present evidence that cerambycid species that are supposed mimics of vespid wasps also mimic their model's odor by producing spiroacetals, common constituents of vespid alarm pheromones. Adults of the North American cerambycids Megacyllene caryae (Gahan) and Megacyllene robiniae (Forster) are conspicuously patterned yellow and black, and are believed to be mimics of aculeate Hymenoptera, such as species of Vespula and Polistes. Adult males of M. caryae produce an aggregation-sex pheromone, but both sexes produce a pungent odor when handled, which has been assumed to be a defensive response. Headspace aerations of agitated females of M. caryae contained 16 compounds with mass spectra characteristic of spiroacetals of eight distinct chemical structures, with the dominant compound being (7E,2E)-7-ethyl-2-methyl-1,6-dioxaspiro[4.5]decane. Headspace samples of agitated males of M. caryae contained five of the same components, with the same dominant compound. Females of M. robiniae produced six different spiroacetals, one of which was not produced by M. caryae, (2E,7E)-2-ethyl-7-methyl-1,6-dioxaspiro[4.5]decane, and five that were shared with M. caryae, including the dominant (2E,8E)-2,8-dimethyl-1,7-dioxaspiro[5.5]undecane. The latter compound is the sole spiroacetal produced by both males and females of a South American cerambycid species, Callisphyris apicicornis (Fairmaire & Germain), which is also thought to be a wasp mimic. Preliminary work also identified spiroacetals of similar or identical structure released by vespid wasps that co-occur with the Megacyllene species"
Keywords:		Acetals/analysis/metabolism Animals *Biological Mimicry Coleoptera/*metabolism Female Male Odorants/*analysis Pheromones/analysis/metabolism Spiro Compounds/analysis/metabolism Wasps/*metabolism Callisphyris apicicornis Cerambycidae Megacyllene caryae Meg;
Notes:		"MedlineMitchell, Robert F Curkovic, Tomislav Mongold-Diers, Judith A Neuteboom, Lara Galbrecht, Hans-Martin Troger, Armin Bergmann, Jan Francke, Wittko Hanks, Lawrence M eng K12 GM000708/GM/NIGMS NIH HHS/ 2016/12/21 J Chem Ecol. 2017 Jan; 43(1):75-83. doi: 10.1007/s10886-016-0800-1. Epub 2016 Dec 19"