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Pheromone of the elm bark beetle Scolytus laevis (Coleoptera: Scolytidae): stereoisomers of 4-methyl-3-heptanol reduce interspecific competition

Anderbrant, Olle LU ; Matteson, Donald S.; Unelius, C. Rikard; Pharazyn, Philip S.; Santangelo, Ellen M.; Schlyter, Fredrik and Birgersson, Göran (2010) In Chemoecology 20(3). p.179-187
Abstract
Stereoisomers of 4-methyl-3-heptanol (MH) are pheromone components of several Scolytus bark beetles. The elm bark beetle Scolytus laevis (Coleoptera: Scolytidae) has in previous studies been caught in traps baited with commercial MH containing all four stereoisomers, but the lure has been considered a weak attractant. In this study, we addressed the question whether stereospecific responses by S. laevis to stereoisomers of MH might contribute to its niche separation from other sympatric Scolytus species. Using GC-MS, we analyzed extracts of hindguts and abdomens from male and female S. laevis and the sympatric S. triarmatus. We also tested all four MH-stereoisomers individually and in combinations in the field to determine their role for... (More)
Stereoisomers of 4-methyl-3-heptanol (MH) are pheromone components of several Scolytus bark beetles. The elm bark beetle Scolytus laevis (Coleoptera: Scolytidae) has in previous studies been caught in traps baited with commercial MH containing all four stereoisomers, but the lure has been considered a weak attractant. In this study, we addressed the question whether stereospecific responses by S. laevis to stereoisomers of MH might contribute to its niche separation from other sympatric Scolytus species. Using GC-MS, we analyzed extracts of hindguts and abdomens from male and female S. laevis and the sympatric S. triarmatus. We also tested all four MH-stereoisomers individually and in combinations in the field to determine their role for S. laevis. All four stereoisomers were synthesized via a boronic ester method with 1,2-dicyclohexylethanediol as chiral director. In addition, the (3S,4R)-stereoisomer of MH was prepared through enantioselective, lipase-mediated transesterification of a mixture of the four stereoisomers of MH. Females of both species contained small amounts of syn-MH, and males contained trace amounts of anti-MH. The anti stereoisomer (3R,4S)-MH was attractive to male and female S. laevis, whereas the syn stereoisomer (3S,4S)-MH acted as an inhibitor or deterrent and reduced the catch when added to the attractive isomer. The syn isomer is the main aggregation pheromone component of the larger and sympatric S. scolytus and possibly also of S. triarmatus. The avoidance response of S. laevis to the (3S,4S)-stereoisomer may reduce interspecific competition for host trees. (Less)
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author
organization
publishing date
type
Contribution to journal
publication status
published
subject
keywords
Attractant, Semiochemical, Chemical analysis, Synthesis, triarmatus, Scolytus, Dutch elm disease
in
Chemoecology
volume
20
issue
3
pages
179 - 187
publisher
Birkhaüser
external identifiers
  • wos:000280782700001
  • scopus:77955422762
ISSN
1423-0445
DOI
10.1007/s00049-010-0042-6
project
Chemical communication in sawflies
language
English
LU publication?
yes
id
0375b43f-2e24-47fd-994a-88df9297372f (old id 1676859)
date added to LUP
2010-09-22 08:06:03
date last changed
2018-05-29 09:28:03
@article{0375b43f-2e24-47fd-994a-88df9297372f,
  abstract     = {Stereoisomers of 4-methyl-3-heptanol (MH) are pheromone components of several Scolytus bark beetles. The elm bark beetle Scolytus laevis (Coleoptera: Scolytidae) has in previous studies been caught in traps baited with commercial MH containing all four stereoisomers, but the lure has been considered a weak attractant. In this study, we addressed the question whether stereospecific responses by S. laevis to stereoisomers of MH might contribute to its niche separation from other sympatric Scolytus species. Using GC-MS, we analyzed extracts of hindguts and abdomens from male and female S. laevis and the sympatric S. triarmatus. We also tested all four MH-stereoisomers individually and in combinations in the field to determine their role for S. laevis. All four stereoisomers were synthesized via a boronic ester method with 1,2-dicyclohexylethanediol as chiral director. In addition, the (3S,4R)-stereoisomer of MH was prepared through enantioselective, lipase-mediated transesterification of a mixture of the four stereoisomers of MH. Females of both species contained small amounts of syn-MH, and males contained trace amounts of anti-MH. The anti stereoisomer (3R,4S)-MH was attractive to male and female S. laevis, whereas the syn stereoisomer (3S,4S)-MH acted as an inhibitor or deterrent and reduced the catch when added to the attractive isomer. The syn isomer is the main aggregation pheromone component of the larger and sympatric S. scolytus and possibly also of S. triarmatus. The avoidance response of S. laevis to the (3S,4S)-stereoisomer may reduce interspecific competition for host trees.},
  author       = {Anderbrant, Olle and Matteson, Donald S. and Unelius, C. Rikard and Pharazyn, Philip S. and Santangelo, Ellen M. and Schlyter, Fredrik and Birgersson, Göran},
  issn         = {1423-0445},
  keyword      = {Attractant,Semiochemical,Chemical analysis,Synthesis,triarmatus,Scolytus,Dutch elm disease},
  language     = {eng},
  number       = {3},
  pages        = {179--187},
  publisher    = {Birkhaüser},
  series       = {Chemoecology},
  title        = {Pheromone of the elm bark beetle <i>Scolytus laevis</i> (Coleoptera: Scolytidae): stereoisomers of 4-methyl-3-heptanol reduce interspecific competition},
  url          = {http://dx.doi.org/10.1007/s00049-010-0042-6},
  volume       = {20},
  year         = {2010},
}