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Wassgren AB Bergström G Sierpinski A Anderbrant O Högberg HE Hedenström E 《Die Naturwissenschaften》2000,87(1):24-29
The main component of the sex pheromone precursor in females of Macrodiprion nemoralis was identified as a threo-3,7,9-trimethyl-2-tridecanol isomer, approximately 800 pg per female, by gas chromatography–mass spectrometry. Comparison
of mass spectrometric ion chromatograms showed that the natural compound in the female extract has the same retention time
and mass spectrum as one of the two synthetic threo peaks. The acetate of the synthetic 16-isomer mixture caught a large number
of males in the field, confirming the structure of the active pheromone. Comparison of gas chromatograms of the natural female
extract with the eight synthetic threo stereoisomers showed that the pheromone is the (2S,3R,7R,9S)-stereoisomer of 3,7,9-trimethyl-2-tridecyl acetate.
Received: 12 May 1999 / Accepted in revised form: 16 September 1999 相似文献
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Olle Anderbrant Fredrik Östrand Gunnar Bergström Ann-Britt Wassgren Marie-Anne Auger-Rozenberg Claude Geri Erik Hedenström Hans-Erik Högberg Annette Herz Werner Heitland 《Chemoecology》2005,15(3):147-151
Summary. The first identification of a sex pheromone of a pine sawfly (Hymenoptera, Diprionidae) dates back almost thirty years. Since then, female-produced pheromones of over twenty diprionid species have been investigated by solvent extraction followed by separation and identification. However, no study has shown what the females actually release. Collection of airborne compounds using absorbtion on charcoal filter as well as solid phase microextraction (SPME) followed by analysis employing gas chromatography combined with mass spectrometry (GC-MS), revealed an unusual system in Diprion pini, in which the pheromone precursor alcohol, 3,7-dimethyl-2-tridecanol, is released together with acetic, propionic, butyric and isobutyric acids. The corresponding acetate, propionate and butyrate esters of 3,7-dimethyl-2-tridecanol were also found in the samples. All esters were electrophysiologically active, and the propionate and isobutyrate were attractive in trapping experiments. Based on these and earlier reported results, it seems that at least in part of its range, the pheromone response of D. pini is not very specific with regard to the functional group, as long as this is an ester. 相似文献
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Fredrik??strandEmail author Olle?Anderbrant Ann-Britt?Wassgren Gunnar?Bergstr?m Erik?Hedenstr?m Hans-Erik?H?gberg Ba-Vu?Nguyen Michael?Larsson 《Chemoecology》2003,13(3):155-162
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. 相似文献
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