« Previous Abstract"Genome-Wide Identification, Classification, and Expression Profiling Reveals R2R3-MYB Transcription Factors Related to Monoterpenoid Biosynthesis in Osmanthus fragrans"    Next AbstractEvaluating competitive sorption mechanisms of volatile organic compounds in soils and sediments using polymers and zeolites »

J Chem Ecol

Title:		Chirality of synergistic sex pheromone components of the western hemlock looperLambdina fiscellaria lugubrosa (HULST) (Lepidoptera: Geometridae)
Author(s):		Li J; Gries G; Gries R; Bikic J; Slessor KN;
Address:		"Departments of Chemistry, Simon Fraser University, V5A 1S6, Burnaby, British Columbia, Canada"
Journal Title:		J Chem Ecol
Year:		1993
Volume:		19
Issue:		11
Page Number:		2547 - 2561
DOI:		10.1007/BF00980690
ISSN/ISBN:		0098-0331 (Print) 0098-0331 (Linking)
Abstract:		"Bakers' yeast reduction of (2E)-3-(2'-furanyl)-2-methyl-2-propenal yielded the synthetic intermediate, (2S)-3-(2'-furanyl)-2-methylpropanol, of high chiral purity (>97% ee) for the synthesis of the enantiomers of 2,5-dimethylheptadecane and 7-methylheptadecane, two synergistic sex pheromone components of the western hemlock looper (WHL),Lambdina fiscellaria lugubrosa Hulst. In electrophysiological bioassays, (7S)- but not (7R)-7-methylheptadecane elicited strong antennal responses by male WHL antennae. In field trapping experiments, addition of (7S)- but not (7R)-7-methylheptadecane to (5R,11S)-5,11-dimethylheptadecane, the major sex pheromone component of WHL, increased attraction. Attraction to (5R,11S)-5,11-dimethylheptadecane in combination with (7S)-7-methyiheptadecane was further enhanced by the addition of (5S)- but not (5R)-2,5-dimethylheptadecane. Similarly, attraction to (5R,11S)-5,11-dimethylheptadecane combined with (5S)-2,5-dimethylheptadecane increased when 7S- but not (7R)-7-methylheptadecane was added as a third component. We conclude that (7S)-7-methylheptadecane and (5S)-2,5-dimethylheptadecane are the synergistic sex pheromone components of WHL. The synthetic methodology described is applicable to the synthesis of chiral methyl-branched pheromones in other orders of the Insecta, particularly Coleoptera, Diptera and Orthoptera"
Keywords:
Notes:		"PubMed-not-MEDLINELi, J Gries, G Gries, R Bikic, J Slessor, K N eng 1993/11/01 J Chem Ecol. 1993 Nov; 19(11):2547-61. doi: 10.1007/BF00980690"