ISSN:
1573-1561
Keywords:
Bark beetles
;
exo-brevicomin
;
Endo-brevicomin
;
Coleoptera
;
deuterium
;
(E)-6-nonen-2-one
;
(Z)-6-nonen-2-one
;
pheromone biosynthesis
;
Scolytidae
Source:
Springer Online Journal Archives 1860-2000
Topics:
Biology
,
Chemistry and Pharmacology
Notes:
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.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1007/BF00994364
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