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Semi-selective fatty acyl reductases from four Heliothine moths influence the specific pheromone composition

Hagström, Åsa LU ; Liénard, Marjorie LU ; Groot, Astrid T; Hedenström, Erik and Löfstedt, Christer LU (2012) In PLoS ONE 7(e37230). p.1-11
Abstract
Background: Sex pheromones are essential in moth mate communication. Information on pheromone biosynthetic genes

and enzymes is needed to comprehend the mechanisms that contribute to specificity of pheromone signals. Most

heliothine moths use sex pheromones with (Z)–11–hexadecenal as the major component in combination with minor fatty

aldehydes and alcohols. In this study we focus on four closely related species, Heliothis virescens, Heliothis subflexa,

Helicoverpa armigera and Helicoverpa assulta
, which use (Z)–11–hexadecenal, (Z)–9–tetradecanal, and (Z)–9–hexadecenal in

different ratios in their pheromone blend. The components are produced from saturated fatty acid precursors... (More)
Background: Sex pheromones are essential in moth mate communication. Information on pheromone biosynthetic genes

and enzymes is needed to comprehend the mechanisms that contribute to specificity of pheromone signals. Most

heliothine moths use sex pheromones with (Z)–11–hexadecenal as the major component in combination with minor fatty

aldehydes and alcohols. In this study we focus on four closely related species, Heliothis virescens, Heliothis subflexa,

Helicoverpa armigera and Helicoverpa assulta
, which use (Z)–11–hexadecenal, (Z)–9–tetradecanal, and (Z)–9–hexadecenal in

different ratios in their pheromone blend. The components are produced from saturated fatty acid precursors by

desaturation, b–oxidation, reduction and oxidation.

Results: We analyzed the composition of fatty acyl pheromone precursors and correlated it to the pheromone composition.

Next, we investigated whether the downstream fatty–acyl reduction step modulates the ratio of alcohol intermediates

before the final oxidation step. By isolating and functionally characterizing the Fatty Acyl Reductase (pgFAR) from each

species we found that the pgFARs were active on a broad set of C8 to C16 fatty acyl substrates including the key

pheromone precursors, Z9–14, Z9–16 and Z11–16:acyls. When presenting the three precursors in equal ratios to yeast

cultures expressing any of the four pgFARs, all reduced (Z)–9–tetradecenoate preferentially over (Z)–11–hexadecenoate, and

the latter over (Z)–9–hexadecenoate. Finally, when manipulating the precursor ratios in vitro, we found that the pgFARs

display small differences in the biochemical activity on various substrates.

Conclusions: We conclude that a pgFAR with broad specificity is involved in heliothine moth pheromone biosynthesis,

functioning as a semi–selective funnel that produces species–specific alcohol product ratios depending on the fatty–acyl

precursor ratio in the pheromone gland. This study further supports the key role of these in pheromone biosynthesis and

emphasizes the interplay between the pheromone fatty acyl precursors and the Lepidoptera specific pgFARs in shaping the

pheromone composition. (Less)
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author
organization
publishing date
type
Contribution to journal
publication status
published
subject
in
PLoS ONE
volume
7
issue
e37230
pages
1 - 11
publisher
Public Library of Science
external identifiers
  • wos:000305341300089
  • scopus:84861204498
ISSN
1932-6203
DOI
10.1371/journal.pone.0037230
project
Evolutionary mechanisms of pheromone divergence in Lepidoptera
language
English
LU publication?
yes
id
69dbd708-1774-4569-8dfc-50c37309fb72 (old id 2863105)
date added to LUP
2012-07-19 12:02:05
date last changed
2017-10-22 04:13:30
@article{69dbd708-1774-4569-8dfc-50c37309fb72,
  abstract     = {Background: Sex pheromones are essential in moth mate communication. Information on pheromone biosynthetic genes<br/><br>
and enzymes is needed to comprehend the mechanisms that contribute to specificity of pheromone signals. Most<br/><br>
heliothine moths use sex pheromones with (Z)–11–hexadecenal as the major component in combination with minor fatty<br/><br>
aldehydes and alcohols. In this study we focus on four closely related species, <i>Heliothis virescens, Heliothis subflexa,<br/><br>
Helicoverpa armigera and Helicoverpa assulta</i>, which use (Z)–11–hexadecenal, (Z)–9–tetradecanal, and (Z)–9–hexadecenal in<br/><br>
different ratios in their pheromone blend. The components are produced from saturated fatty acid precursors by<br/><br>
desaturation, b–oxidation, reduction and oxidation.<br/><br>
Results: We analyzed the composition of fatty acyl pheromone precursors and correlated it to the pheromone composition.<br/><br>
Next, we investigated whether the downstream fatty–acyl reduction step modulates the ratio of alcohol intermediates<br/><br>
before the final oxidation step. By isolating and functionally characterizing the Fatty Acyl Reductase (pgFAR) from each<br/><br>
species we found that the pgFARs were active on a broad set of C8 to C16 fatty acyl substrates including the key<br/><br>
pheromone precursors, Z9–14, Z9–16 and Z11–16:acyls. When presenting the three precursors in equal ratios to yeast<br/><br>
cultures expressing any of the four pgFARs, all reduced (Z)–9–tetradecenoate preferentially over (Z)–11–hexadecenoate, and<br/><br>
the latter over (Z)–9–hexadecenoate. Finally, when manipulating the precursor ratios in vitro, we found that the pgFARs<br/><br>
display small differences in the biochemical activity on various substrates.<br/><br>
Conclusions: We conclude that a pgFAR with broad specificity is involved in heliothine moth pheromone biosynthesis,<br/><br>
functioning as a semi–selective funnel that produces species–specific alcohol product ratios depending on the fatty–acyl<br/><br>
precursor ratio in the pheromone gland. This study further supports the key role of these in pheromone biosynthesis and<br/><br>
emphasizes the interplay between the pheromone fatty acyl precursors and the Lepidoptera specific pgFARs in shaping the<br/><br>
pheromone composition.},
  author       = {Hagström, Åsa and Liénard, Marjorie and Groot, Astrid T and Hedenström, Erik and Löfstedt, Christer},
  issn         = {1932-6203},
  language     = {eng},
  number       = {e37230},
  pages        = {1--11},
  publisher    = {Public Library of Science},
  series       = {PLoS ONE},
  title        = {Semi-selective fatty acyl reductases from four Heliothine moths influence the specific pheromone composition},
  url          = {http://dx.doi.org/10.1371/journal.pone.0037230},
  volume       = {7},
  year         = {2012},
}