Hooper, A. M., Donato, B., Woodcock, C. M., Park, J. H., Paul, R. L., Boo, K. S., Hardie, J. and Pickett, John A.  ORCID: https://orcid.org/0000-0002-8386-3770
2002.
Characterization of (1R,4S,4aR,7S,7aR)-dihydronepetalactol as a semiochemical for lacewings, including Chrysopa spp. and Peyerimhoffina gracilis.
Journal of Chemical Ecology
28
(4)
, pp. 849-864.
10.1023/A:1015201129331
|
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.
| Item Type: | Article |
|---|---|
| Date Type: | Publication |
| Status: | Published |
| Schools: | Schools > Chemistry |
| Publisher: | Springer |
| ISSN: | 0098-0331 |
| Last Modified: | 05 Mar 2026 14:15 |
| URI: | https://orca.cardiff.ac.uk/id/eprint/185523 |
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