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J Chem Ecol

Title:		"Characterization of (1'R,4S,4aR,7S,7aR)-dihydronepetalactol as a semiochemical for lacewings, including Chrysopa spp. and Peyerimhoffina gracilis"
Author(s):		Hooper AM; Donato B; Woodcock CM; Park JH; Paul RL; Boo KS; Hardie J; Pickett JA;
Address:		"Biological Chemistry Division, IACR-Rothamsted Harpenden, Herts, United Kingdom"
Journal Title:		J Chem Ecol
Year:		2002
Volume:		28
Issue:		4
Page Number:		849 - 864
DOI:		10.1023/a:1015201129331
ISSN/ISBN:		0098-0331 (Print) 0098-0331 (Linking)
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 Peverimhoffina 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"
Keywords:		"Animals Aphids/*chemistry/metabolism Crystallography, X-Ray Cyclopentane Monoterpenes Cyclopentanes/*chemical synthesis/*chemistry Electrophysiology Gas Chromatography-Mass Spectrometry Lactones/*chemistry Magnetic Resonance Spectroscopy Male Pyrones/*che;"
Notes:		"MedlineHooper, A M Donato, B Woodcock, C M Park, J H Paul, R L Boo, K S Hardie, J Pickett, J A eng Research Support, Non-U.S. Gov't 2002/05/31 J Chem Ecol. 2002 Apr; 28(4):849-64. doi: 10.1023/a:1015201129331"