Characterization of (1'R,4S,4aR,7S,7aR)-dihydronepetalactol as a semiochemical for lacewings,including Chrysopa spp. and Peyerimhoffina gracilis |
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Authors: | Hooper A M Donato B Woodcock C M Park J H Paul R L Boo K S Hardie J Pickett J A |
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Affiliation: | (1) Biological Chemistry Division, IACR-Rothamsted, Harpenden, Herts., AL5 2JQ, United Kingdom;(2) Aphid Biology Group, Department of Biological Sciences, Imperial College at Silwood Park, Ascot, Berks., SL5 7PY, United Kingdom;(3) School of Agricultural Biotechnology, Seoul National University, Suwon, 441-744, Korea;(4) School of Chemistry, Cantock's Close, University of Bristol, Bristol, BS8 1TS, United Kingdom |
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Abstract: | 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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Keywords: | Nepeta cataria Chrysopa cognata Chrysopa formosa Chrysopa phyllochroma Nineta vittata Peyerimhoffina gracilis lacewing pheromone dihydronepetalactol neomatatabiol isoneomatatabiol |
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