Characterization of (1'R,4S,4aR,7S,7aR)-dihydronepetalactol as a semiochemical for lacewings, including Chrysopa spp. and Peyerimhoffina gracilis.
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.
Hooper
A M
AM
Biological Chemistry Division, IACR-Rothamsted Harpenden, Herts, United Kingdom.
Donato
B
B
Woodcock
C M
CM
Park
J H
JH
Paul
R L
RL
Boo
K S
KS
Hardie
J
J
Pickett
J A
JA
D000818:Animals; D001042:Aphids / Q000737:chemistry* / Q000378:metabolism; D018360:Crystallography, X-Ray; D000081004:Cyclopentane Monoterpenes; D003517:Cyclopentanes / Q000138:chemical synthesis* / Q000737:chemistry*; D004594:Electrophysiology; D008401:Gas Chromatography-Mass Spectrometry; D007783:Lactones / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008297:Male; D011753:Pyrones / Q000737:chemistry*; D012724:Sex Attractants / Q000737:chemistry; D013237:Stereoisomerism
D000081004:Cyclopentane Monoterpenes; D003517:Cyclopentanes; D007783:Lactones; D011753:Pyrones; D012724:Sex Attractants; C469408:dihydronepetalactol; C115644:nepetalactone