Journal
JOURNAL OF CHEMICAL ECOLOGY
Volume 28, Issue 4, Pages 849-864Publisher
KLUWER ACADEMIC/PLENUM PUBL
DOI: 10.1023/A:1015201129331
Keywords
Nepeta cataria; Chrysopa cognata; Chrysopa formosa; Chrysopa phyllochroma; Nineta vittata; Peyerimhoffina gracilis; lacewing; pheromone; dihydronepetalactol; neomatatabiol; isoneomatatabiol
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The enantiomerically pure diastereoisomers (1R,4S,4aR,7S,7aR)(1) and (1R,4R,4aR,7S,7aR)-dihydronepetalactol (2) were synthesized diastereoselectively from a renewable resource, (4aS,7S,7aR)-nepetalactone (3), isolated as the main constituent of the essential oil of the catmint plant Nepeta cataria. The stereochemistry of the compounds was determined by NMR spectroscopy and X-ray crystallography, and the compounds were identified, respectively, as neomatatabiol and isoneomatatabiol, natural products from Actinidia polygama, for which the lactol stereochemistry was previously incompletely defined. Compound 1 was found to catch significant numbers of three species of lacewing in the field: in Korea, Chrysopa cognata, and in the United Kingdom, Nineta vittata and most notably Peyerimhoffina gracilis. All species caught in significant numbers were found more frequently in traps releasing 1 than 2, while more C. cognata, C. formosa, and C. phyllochroma were found in traps releasing (1R,4aS,7S,7aR)-nepetalactol (4). The catch of P. gracilis with 1 is of particular interest as this lacewing has only recently been recorded in the United Kingdom. Where sexed, the lacewings of all species trapped were found to be male, implying a possible pheromonal role for these or structurally related compounds.
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