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J Chem Ecol

Title:		Identification of Sex Pheromones and Sex Pheromone Mimics for Two North American Click Beetle Species (Coleoptera: Elateridae) in the Genus Cardiophorus Esch
Author(s):		Serrano JM; Collignon RM; Zou Y; Millar JG;
Address:		"Department of Entomology, University of California, Riverside, CA, 92521, USA. jacqueline.serrano@email.ucr.edu. Department of Entomology, University of California, Riverside, CA, 92521, USA. USDA-ARS, Daniel K. Inouye U.S. Pacific Basin Agricultural Research Center, Hilo, HI, 96720, USA. Department of Chemistry, University of California, Riverside, CA, 92521, USA"
Journal Title:		J Chem Ecol
Year:		2018
Volume:		20180225
Issue:		4
Page Number:		327 - 338
DOI:		10.1007/s10886-018-0940-6
ISSN/ISBN:		1573-1561 (Electronic) 0098-0331 (Linking)
Abstract:		"To date, all known or suspected pheromones of click beetles (Coleoptera: Elateridae) have been identified solely from species native to Europe and Asia; reports of identifications from North American species dating from the 1970s have since proven to be incorrect. While conducting bioassays of pheromones of a longhorned beetle (Coleoptera: Cerambycidae), we serendipitously discovered that males of Cardiophorus tenebrosus L. and Cardiophorus edwardsi Horn were specifically attracted to the cerambycid pheromone fuscumol acetate, (E)-6,10-dimethylundeca-5,9-dien-2-yl acetate, suggesting that this compound might also be a sex pheromone for the two Cardiophorus species. Further field bioassays and electrophysiological assays with the enantiomers of fuscumol acetate determined that males were specifically attracted by the (R)-enantiomer. However, subsequent analyses of extracts of volatiles from female C. tenebrosus and C. edwardsi showed that the females actually produced a different compound, which was identified as (3R,6E)-3,7,11-trimethyl-6,10-dodecadienoic acid methyl ester (methyl (3R,6E)-2,3-dihydrofarnesoate). In field trials, both the racemate and the (R)-enantiomer of the pheromone attracted similar numbers of male beetles, suggesting that the (S)-enantiomer was not interfering with responses to the insect-produced (R)-enantiomer. This report constitutes the first conclusive identification of sex pheromones for any North American click beetle species. Possible reasons for the strong and specific attraction of males to fuscumol acetate, which is markedly different in structure to the actual pheromone, are discussed"
Keywords:		"Animals Behavior, Animal/drug effects/physiology Chromatography, Gas Coleoptera/*physiology Fatty Acids, Unsaturated/chemistry/isolation & purification/pharmacology Female Male North America Pheromones/chemistry/isolation & purification/pharmacology Sex A;"
Notes:		"MedlineSerrano, Jacqueline M Collignon, R Maxwell Zou, Yunfan Millar, Jocelyn G eng Robert van den Bosch Scholarship/Center for Biological Control - UC Berkeley/ 2018/02/27 J Chem Ecol. 2018 Apr; 44(4):327-338. doi: 10.1007/s10886-018-0940-6. Epub 2018 Feb 25"