Stereoisomeric composition of the sex pheromone of the pine sawfly <Emphasis Type="Italic">Microdiprion pallipes</Emphasis> (Hym., Diprionidae) |
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Authors: | Email author" target="_blank">Fredrik??strandEmail author Olle?Anderbrant Ann-Britt?Wassgren Gunnar?Bergstr?m Erik?Hedenstr?m Hans-Erik?H?gberg Ba-Vu?Nguyen Michael?Larsson |
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Institution: | (1) Department of Ecology, Ecology Building, Lund University, 223 62 Lund, Sweden;(2) Chemical Ecology, Göteborg University, 461 Göteborg, Sweden;(3) Chemistry, Department of Natural and Environmental Sciences, Mid Sweden University , 851 70 Sundsvall, Sweden |
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Abstract: | Summary. The basic chemical structure of the sex
pheromone of the pine sawfly Microdiprion pallipes
(Fallén) has earlier been identified as the propionate
ester of (2S,3S,7R/S,11R/S)/(2R,3R,7R/S,11R/S)-3,7,11-
trimethyl-2-tridecanol. We now report the results from
further investigations on the male response to individual
stereoisomers and to blends of stereoisomers, both in electroantennographic
(EAG) recordings and in field trapping
experiments. We also present our attempts to determine the
stereochemistry of the compounds present in females of
M. pallipes. By comparing gas chromatograms and mass
spectra obtained from natural extracts with those from synthetic
compounds it was found that the females contain one
or more of the four (2S,3S,7R/S,11R/S)-3,7,11-trimethyl-2-
tridecanol isomers (SS++-1). The active pheromone component
is the corresponding propionate ester 2. In EAG
experiments, males responded most strongly to five propionate
ester samples, namely two four-isomer blends: SS++-2
and SR++-2, and three individual stereoisomers: SSSR-,
SRRR- and SRSR-2. In a series of field trapping experiments
it was found that males were attracted to the SR++-2
four-isomer blend and to the individual isomer SSSR-2.
Based on the EAG-recordings and field responses of males
and the stereoisomers found in the females, we suggest that
the propionate ester of (2S,3S,7S,11R)-3,7,11-trimethyl-2-
tridecanol (SSSR-2) is used as a main component of the sex
pheromone in M. pallipes. Apparently the males react to
other stereoisomers in addition to that or those produced by
the females. |
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Keywords: | Chiral separation stereoisomers Diprionidae Hymenoptera EAG propionate of 3 7 11-trimethyl-2-tridecanol mass spectrometry |
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