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J Chem Ecol

Title:		(E)- and (Z)-6-nonen-2-one: Biosynthetic precursors ofEndo- andexo-brevicomin in two bark beetles (Coleoptera: Scolytidae)
Author(s):		Vanderwel D; Gries G; Singh SM; Borden JH; Oehlschlager AC;
Address:		"Department of Chemistry, Simon Fraser University, Burnaby, British Columbia, Canada"
Journal Title:		J Chem Ecol
Year:		1992
Volume:		18
Issue:		8
Page Number:		1389 - 1404
DOI:		10.1007/BF00994364
ISSN/ISBN:		0098-0331 (Print) 0098-0331 (Linking)
Abstract:		"The ability of (E)- and (Z)-6-nonen-2-one to serve as precursors of the common scolytid pheromonesEndo- andexo-brevicomin was examined in vivo. When mountain pine beetles (MPB),Dendroctonus ponderosae Hopkins, or western balsam bark beetles (WBBB),Dryocoetes confusus Swaine, were exposed to [6,7-D2](E)-6-nonen-2-one, theEndo-brevicomin produced was enriched with two deuterium atoms per molecule (as determined by GC-MS), indicating that (E)-6-nonen-2-one served as a precursor of this pheromone. Similarly, when the beetles were exposed to [4,4-D2](Z)-6-nonen-2-one, theexo-brevicomin produced was enriched with two deuterium atoms per molecule. Evidence in support of biological relevance of the latter observation include: (1) (Z)-6-nonen-2-one was found in the volatiles of male MPBs and WBBBs, indicating that this is a natural metabolite; (2) theexo-brevicomin produced by MPB was shown to be of natural (+) chirality by complexation chromatography; and (3) female WBBBs and MPBs (which are not known to produceexo-brevicomin) produced significantly lessexo-brevicomin when exposed to the precursor than did the males"
Keywords:
Notes:		"PubMed-not-MEDLINEVanderwel, D Gries, G Singh, S M Borden, J H Oehlschlager, A C eng 1992/08/01 J Chem Ecol. 1992 Aug; 18(8):1389-404. doi: 10.1007/BF00994364"