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A novel fatty acyl desaturase from the pheromone glands of Ctenopseustis obliquana and C. herana with specific Z5-desaturase activity on myristic acid

Hagström, Åsa LU ; Albre, Jerome; Tooman, Leah K.; Thirmawithana, Amali H.; Corcoran, Jacob; Löfstedt, Christer LU and Newcomb, Richard D. (2014) In Journal of Chemical Ecology 40(1). p.63-70
Abstract
Sexual communication in the Lepidoptera typically involves a female-produced sex pheromone that attracts males of the same species. The most common type of moth sex pheromone comprises individual or blends of fatty acyl derivatives that are synthesized by a specific enzymatic pathway in the female’s pheromone gland, often including a desaturation step. This reaction is catalyzed by fatty acyl desaturases that introduce double bonds at specific locations in the fatty acid precursor backbone. The two tortricid moths, Ctenopseustis obliquana and C. herana (brown-headed leafrollers), which are endemic in New Zealand, both use (Z)-5-tetradecenyl acetate as part of their sex pheromone. In [i]C. herana[i], (Z)-5-tetradecenyl acetate... (More)
Sexual communication in the Lepidoptera typically involves a female-produced sex pheromone that attracts males of the same species. The most common type of moth sex pheromone comprises individual or blends of fatty acyl derivatives that are synthesized by a specific enzymatic pathway in the female’s pheromone gland, often including a desaturation step. This reaction is catalyzed by fatty acyl desaturases that introduce double bonds at specific locations in the fatty acid precursor backbone. The two tortricid moths, Ctenopseustis obliquana and C. herana (brown-headed leafrollers), which are endemic in New Zealand, both use (Z)-5-tetradecenyl acetate as part of their sex pheromone. In [i]C. herana[i], (Z)-5-tetradecenyl acetate is the sole component of the pheromone. Labeling experiments have revealed that this compound is produced via an unusual Δ5-desaturation of myristic acid. Previously six desaturases were identified from the pheromone glands of Ctenopseustis and its sibling genus [i]Planotortrix[i], with one differentially regulated to produce the distinct blends used by individual species. However, none were able to conduct the Δ5-desaturation observed in C. herana, and presumably C. obliquana. We have now identified an additional desaturase gene, desat7, expressed in the pheromone glands of both Ctenopseustis species, which is not closely related to any previously described moth pheromone desaturase. The encoded enzyme displays Δ5-desaturase activity on myristic acid when heterologously expressed in yeast, but is not able to desaturate any other fatty acid (C8–C16). We conclude that desat7 represents a new group of desaturases that has evolved a role in the biosynthesis of sex pheromones in moths. (Less)
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author
organization
publishing date
type
Contribution to journal
publication status
published
subject
in
Journal of Chemical Ecology
volume
40
issue
1
pages
63 - 70
publisher
Springer
external identifiers
  • pmid:24408442
  • wos:000330988300007
  • scopus:84895074814
ISSN
1573-1561
DOI
10.1007/s10886-013-0373-1
project
Evolutionary mechanisms of pheromone divergence in Lepidoptera
language
English
LU publication?
yes
id
3147de3f-836b-4d3d-a14e-8e6a4c749a24 (old id 4280901)
date added to LUP
2014-01-31 15:01:16
date last changed
2017-10-01 03:28:41
@article{3147de3f-836b-4d3d-a14e-8e6a4c749a24,
  abstract     = {Sexual communication in the Lepidoptera typically involves a female-produced sex pheromone that attracts males of the same species. The most common type of moth sex pheromone comprises individual or blends of fatty acyl derivatives that are synthesized by a specific enzymatic pathway in the female’s pheromone gland, often including a desaturation step. This reaction is catalyzed by fatty acyl desaturases that introduce double bonds at specific locations in the fatty acid precursor backbone. The two tortricid moths, <i>Ctenopseustis obliquana</i> and <i>C. herana</i> (brown-headed leafrollers), which are endemic in New Zealand, both use (Z)-5-tetradecenyl acetate as part of their sex pheromone. In [i]C. herana[i], (Z)-5-tetradecenyl acetate is the sole component of the pheromone. Labeling experiments have revealed that this compound is produced via an unusual Δ5-desaturation of myristic acid. Previously six desaturases were identified from the pheromone glands of <i>Ctenopseustis</i> and its sibling genus [i]Planotortrix[i], with one differentially regulated to produce the distinct blends used by individual species. However, none were able to conduct the Δ5-desaturation observed in C. herana, and presumably C. obliquana. We have now identified an additional desaturase gene, desat7, expressed in the pheromone glands of both Ctenopseustis species, which is not closely related to any previously described moth pheromone desaturase. The encoded enzyme displays Δ5-desaturase activity on myristic acid when heterologously expressed in yeast, but is not able to desaturate any other fatty acid (C8–C16). We conclude that desat7 represents a new group of desaturases that has evolved a role in the biosynthesis of sex pheromones in moths.},
  author       = {Hagström, Åsa and Albre, Jerome and Tooman, Leah K. and Thirmawithana, Amali H. and Corcoran, Jacob and Löfstedt, Christer and Newcomb, Richard D.},
  issn         = {1573-1561},
  language     = {eng},
  number       = {1},
  pages        = {63--70},
  publisher    = {Springer},
  series       = {Journal of Chemical Ecology},
  title        = {A novel fatty acyl desaturase from the pheromone glands of <i>Ctenopseustis obliquana</i> and <i>C. herana</i> with specific <i>Z</i>5-desaturase activity on myristic acid},
  url          = {http://dx.doi.org/10.1007/s10886-013-0373-1},
  volume       = {40},
  year         = {2014},
}