Stereoisomeric composition of the sex pheromone of the pine sawfly Microdiprion pallipes (Hym., Diprionidae)
(2003) In Chemoecology 13(3). p.155-162- Abstract
- 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... (More)
- 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. (Less)
Please use this url to cite or link to this publication:
https://lup.lub.lu.se/record/135910
- author
- Östrand, Fredrik LU ; Anderbrant, Olle LU ; Wassgren, Ann-Britt ; Bergström, Gunnar ; Hedenstrom, Erik ; Högberg, Hans-Erik ; Nguyen, B V and Larsson, Mattias
- organization
- publishing date
- 2003
- type
- Contribution to journal
- publication status
- published
- subject
- in
- Chemoecology
- volume
- 13
- issue
- 3
- pages
- 155 - 162
- publisher
- Birkhäuser
- external identifiers
-
- wos:000185481100007
- scopus:0141676076
- ISSN
- 1423-0445
- DOI
- 10.1007/s00049-003-0244-2
- project
- Chemical communication in sawflies
- language
- English
- LU publication?
- yes
- id
- f698dfa7-5e57-4798-81f5-03a60293a4d7 (old id 135910)
- date added to LUP
- 2016-04-01 11:50:48
- date last changed
- 2024-01-07 22:41:49
@article{f698dfa7-5e57-4798-81f5-03a60293a4d7, abstract = {{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.}}, author = {{Östrand, Fredrik and Anderbrant, Olle and Wassgren, Ann-Britt and Bergström, Gunnar and Hedenstrom, Erik and Högberg, Hans-Erik and Nguyen, B V and Larsson, Mattias}}, issn = {{1423-0445}}, language = {{eng}}, number = {{3}}, pages = {{155--162}}, publisher = {{Birkhäuser}}, series = {{Chemoecology}}, title = {{Stereoisomeric composition of the sex pheromone of the pine sawfly <i>Microdiprion pallipes</i> (Hym., Diprionidae)}}, url = {{http://dx.doi.org/10.1007/s00049-003-0244-2}}, doi = {{10.1007/s00049-003-0244-2}}, volume = {{13}}, year = {{2003}}, }