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Stereoisomeric composition of the sex pheromone of the pine sawfly Microdiprion pallipes (Hym., Diprionidae)
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- Östrand, Fredrik (author)
- Lund University,Lunds universitet,Biologiska institutionen,Naturvetenskapliga fakulteten,Department of Biology,Faculty of Science
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- Anderbrant, Olle (author)
- Lund University,Lunds universitet,Funktionell zoologi,Biologiska institutionen,Naturvetenskapliga fakulteten,Functional zoology,Department of Biology,Faculty of Science
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- Wassgren, Ann-Britt (author)
- University of Gothenburg
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- Larsson, Michael (author)
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- (creator_code:org_t)
- Springer Science and Business Media LLC, 2003
- 2003
- English.
- In: Chemoecology. - : Springer Science and Business Media LLC. - 0937-7409 .- 1423-0445. ; 13:3, s. 155-162
- Journal article (peer-reviewed)
Abstract
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- The basic chemical structure of the sex pheromone of the pine sawfly Microdiprion pallipes (Fallen) has earlier been identified as the propionate ester of (2S,3S,7 R/S,11 R/S)/(2R,3R,7 R/S,11 R/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,7 R/S,11 R/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.
Subject headings
- NATURVETENSKAP -- Kemi (hsv//swe)
- NATURAL SCIENCES -- Chemical Sciences (hsv//eng)
- NATURVETENSKAP -- Biologi -- Zoologi (hsv//swe)
- NATURAL SCIENCES -- Biological Sciences -- Zoology (hsv//eng)
- NATURVETENSKAP -- Biologi (hsv//swe)
- NATURAL SCIENCES -- Biological Sciences (hsv//eng)
Keyword
- Pheromones
- Chemistry
- Kemi
Publication and Content Type
- ref (subject category)
- art (subject category)
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