Biosynthesis of the sex pheromone component (E,Z)-7,9-Dodecadienyl acetate in the European Grapevine Moth, Lobesia botrana, involving ∆11 desaturation and an elusive ∆7 desaturase
(2021) In Journal of Chemical Ecology 47(3). p.248-264- Abstract
The European grapevine moth, Lobesia botrana, uses (E,Z)-7,9-dodecadienyl acetate as its major sex pheromone component. Through in vivo labeling experiments we demonstrated that the doubly unsaturated pheromone component is produced by ∆11 desaturation of tetradecanoic acid, followed by chain shortening of (Z)-11-tetradecenoic acid to (Z)-9-dodecenoic acid, and subsequently introduction of the second double bond by an unknown ∆7 desaturase, before final reduction and acetylation. By sequencing and analyzing the transcriptome of female pheromone glands of L. botrana, we obtained 41 candidate genes that may be involved in sex pheromone production, including the genes encoding 17 fatty acyl desaturases, 13 fatty acyl reductases, 1 fatty... (More)
The European grapevine moth, Lobesia botrana, uses (E,Z)-7,9-dodecadienyl acetate as its major sex pheromone component. Through in vivo labeling experiments we demonstrated that the doubly unsaturated pheromone component is produced by ∆11 desaturation of tetradecanoic acid, followed by chain shortening of (Z)-11-tetradecenoic acid to (Z)-9-dodecenoic acid, and subsequently introduction of the second double bond by an unknown ∆7 desaturase, before final reduction and acetylation. By sequencing and analyzing the transcriptome of female pheromone glands of L. botrana, we obtained 41 candidate genes that may be involved in sex pheromone production, including the genes encoding 17 fatty acyl desaturases, 13 fatty acyl reductases, 1 fatty acid synthase, 3 acyl-CoA oxidases, 1 acetyl-CoA carboxylase, 4 fatty acid transport proteins and 2 acyl-CoA binding proteins. A functional assay of desaturase and acyl-CoA oxidase gene candidates in yeast and insect cell (Sf9) heterologous expression systems revealed that Lbo_PPTQ encodes a ∆11 desaturase producing (Z)-11-tetradecenoic acid from tetradecanoic acid. Further, Lbo_31670 and Lbo_49602 encode two acyl-CoA oxidases that may produce (Z)-9-dodecenoic acid by chain shortening (Z)-11-tetradecenoic acid. The gene encoding the enzyme introducing the E7 double bond into (Z)-9-dodecenoic acid remains elusive even though we assayed 17 candidate desaturases in the two heterologous systems.
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- author
- Ding, Bao Jian LU ; Xia, Yi Han LU ; Wang, Hong Lei LU ; Andersson, Fredrik LU ; Hedenström, Erik ; Gross, Jürgen and Löfstedt, Christer LU
- organization
- publishing date
- 2021-03
- type
- Contribution to journal
- publication status
- published
- subject
- keywords
- Acyl-CoA oxidase, Chain shortening, Gene functional characterization, In vivo labeling experiment, Pheromone gland, Transcriptome, In vivo labeling experiments, transcriptome, gene functional analysis, Acyl-CoA oxidase, chain shortening
- in
- Journal of Chemical Ecology
- volume
- 47
- issue
- 3
- pages
- 248 - 264
- publisher
- Springer
- external identifiers
-
- scopus:85102620320
- pmid:33779878
- ISSN
- 0098-0331
- DOI
- 10.1007/s10886-021-01252-3
- project
- Evolutionary mechanisms of pheromone divergence in Lepidoptera
- language
- English
- LU publication?
- yes
- additional info
- Funding Information: Thanks to LP3 in Department of Biology, Lund University for the technical support for Sf9 expression. The phylogenetics in this paper was enabled by resources provided by the Swedish National Infrastructure for Computing (SNIC) at Rackham hosted at UPPMAX partially funded by the Swedish Research Council through grant agreement no. 2018-05973. Thanks to Sonja Anslinger and Christoph Hoffmann (JKI, Germany) for rearing Lobesia botrana and to Jean-Marc Lassance for advice. Thanks to the Chinese Scholarship Council for supporting Yihan Xia?s PhD scholarship. This project has received funding from the European Union?s Horizon 2020 research and innovation program under grant agreement No. 760798 (OLEFINE), and the Swedish Foundation for Strategic Research (grant No. RBP 14?0037, Oil Crops for the Future). EH and FA were funded by the European Development Funds, the County Board of V?sternorrland, the Region of J?mtland and H?rjedalen, the Region of V?sternorrland, Bratt?sstiftelsen f?r skogsvetenskaplig forskning and Carl Tryggers Stiftelse f?r Vetenskaplig Forskning. Funding Information: Thanks to LP3 in Department of Biology, Lund University for the technical support for Sf9 expression. The phylogenetics in this paper was enabled by resources provided by the Swedish National Infrastructure for Computing (SNIC) at Rackham hosted at UPPMAX partially funded by the Swedish Research Council through grant agreement no. 2018-05973. Thanks to Sonja Anslinger and Christoph Hoffmann (JKI, Germany) for rearing Lobesia botrana and to Jean-Marc Lassance for advice. Thanks to the Chinese Scholarship Council for supporting Yihan Xia’s PhD scholarship. This project has received funding from the European Union’s Horizon 2020 research and innovation program under grant agreement No. 760798 (OLEFINE), and the Swedish Foundation for Strategic Research (grant No. RBP 14–0037, Oil Crops for the Future). EH and FA were funded by the European Development Funds, the County Board of Västernorrland, the Region of Jämtland and Härjedalen, the Region of Västernorrland, Brattåsstiftelsen för skogsvetenskaplig forskning and Carl Tryggers Stiftelse för Vetenskaplig Forskning. Publisher Copyright: © 2021, The Author(s). Copyright: Copyright 2021 Elsevier B.V., All rights reserved.
- id
- f7a3daa1-93d8-4d07-b3a6-16507eb258f3
- date added to LUP
- 2021-10-01 10:22:07
- date last changed
- 2024-06-15 17:08:17
@article{f7a3daa1-93d8-4d07-b3a6-16507eb258f3,
abstract = {{<p>The European grapevine moth, Lobesia botrana, uses (E,Z)-7,9-dodecadienyl acetate as its major sex pheromone component. Through in vivo labeling experiments we demonstrated that the doubly unsaturated pheromone component is produced by ∆11 desaturation of tetradecanoic acid, followed by chain shortening of (Z)-11-tetradecenoic acid to (Z)-9-dodecenoic acid, and subsequently introduction of the second double bond by an unknown ∆7 desaturase, before final reduction and acetylation. By sequencing and analyzing the transcriptome of female pheromone glands of L. botrana, we obtained 41 candidate genes that may be involved in sex pheromone production, including the genes encoding 17 fatty acyl desaturases, 13 fatty acyl reductases, 1 fatty acid synthase, 3 acyl-CoA oxidases, 1 acetyl-CoA carboxylase, 4 fatty acid transport proteins and 2 acyl-CoA binding proteins. A functional assay of desaturase and acyl-CoA oxidase gene candidates in yeast and insect cell (Sf9) heterologous expression systems revealed that Lbo_PPTQ encodes a ∆11 desaturase producing (Z)-11-tetradecenoic acid from tetradecanoic acid. Further, Lbo_31670 and Lbo_49602 encode two acyl-CoA oxidases that may produce (Z)-9-dodecenoic acid by chain shortening (Z)-11-tetradecenoic acid. The gene encoding the enzyme introducing the E7 double bond into (Z)-9-dodecenoic acid remains elusive even though we assayed 17 candidate desaturases in the two heterologous systems.</p>}},
author = {{Ding, Bao Jian and Xia, Yi Han and Wang, Hong Lei and Andersson, Fredrik and Hedenström, Erik and Gross, Jürgen and Löfstedt, Christer}},
issn = {{0098-0331}},
keywords = {{Acyl-CoA oxidase; Chain shortening; Gene functional characterization; In vivo labeling experiment; Pheromone gland; Transcriptome; In vivo labeling experiments; transcriptome; gene functional analysis; Acyl-CoA oxidase; chain shortening}},
language = {{eng}},
number = {{3}},
pages = {{248--264}},
publisher = {{Springer}},
series = {{Journal of Chemical Ecology}},
title = {{Biosynthesis of the sex pheromone component (E,Z)-7,9-Dodecadienyl acetate in the European Grapevine Moth, L<i>obesia botrana</i>, involving ∆11 desaturation and an elusive ∆7 desaturase}},
url = {{http://dx.doi.org/10.1007/s10886-021-01252-3}},
doi = {{10.1007/s10886-021-01252-3}},
volume = {{47}},
year = {{2021}},
}