Green Chemistry Production of Codlemone, the Sex Pheromone of the Codling Moth (Cydia pomonella), by Metabolic Engineering of the Oilseed Crop Camelina (Camelina sativa).

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  • Additional Information
    • Source:
      Publisher: Springer Country of Publication: United States NLM ID: 7505563 Publication Model: Print-Electronic Cited Medium: Internet ISSN: 1573-1561 (Electronic) Linking ISSN: 00980331 NLM ISO Abbreviation: J Chem Ecol Subsets: MEDLINE
    • Publication Information:
      Publication: New York, NY : Springer
      Original Publication: New York, Plenum Press.
    • Subject Terms:
      Metabolic Engineering*; Brassicaceae/*chemistry ; Dodecanol/*analogs & derivatives ; Moths/*drug effects ; Sex Attractants/*pharmacology; Animals ; Dodecanol/chemistry ; Dodecanol/metabolism ; Sex Attractants/chemistry
    • Abstract:
      Synthetic pheromones have been used for pest control over several decades. The conventional synthesis of di-unsaturated pheromone compounds is usually complex and costly. Camelina (Camelina sativa) has emerged as an ideal, non-food biotech oilseed platform for production of oils with modified fatty acid compositions. We used Camelina as a plant factory to produce mono- and di-unsaturated C 12 chain length moth sex pheromone precursors, (E)-9-dodecenoic acid and (E,E)-8,10-dodecadienoic acid, by introducing a fatty acyl-ACP thioesterase FatB gene UcTE from California bay laurel (Umbellularia californica) and a bifunctional ∆9 desaturase gene Cpo_CPRQ from the codling moth, Cydia pomonella. Different transgene combinations were investigated for increasing pheromone precursor yield. The most productive Camelina line was engineered with a vector that contained one copy of UcTE and the viral suppressor protein encoding P19 transgenes and three copies of Cpo_CPRQ transgene. The T 2 generation of this line produced 9.4% of (E)-9-dodecenoic acid and 5.5% of (E,E)-8,10-dodecadienoic acid of the total fatty acids, and seeds were selected to advance top-performing lines to homozygosity. In the T 4 generation, production levels of (E)-9-dodecenoic acid and (E,E)-8,10-dodecadienoic acid remained stable. The diene acid together with other seed fatty acids were converted into corresponding alcohols, and the bioactivity of the plant-derived codlemone was confirmed by GC-EAD and a flight tunnel assay. Trapping in orchards and home gardens confirmed significant and specific attraction of C. pomonella males to the plant-derived codlemone.
      (© 2021. The Author(s).)
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    • Grant Information:
      RBP 14-0037 stiftelsen för strategisk forskning; No. 760798 horizon 2020 framework programme; CTS 14:307 carl tryggers stiftelse för vetenskaplig forskning; CTS KF17:15 carl tryggers stiftelse för vetenskaplig forskning; 2010-857 svenska forskningsrådet formas; 2015-1336 svenska forskningsrådet formas; NEB-30-131 nebraska agricultural experiment station-usda hatch act
    • Contributed Indexing:
      Keywords: Acyl-ACP thioesterase; Agrobacterium-based floral-dip transformation; Bioassay; Conjugated double bonds; Multi-gene copies; P19; Plant factory; ∆9 desaturase
    • Accession Number:
      0 (Sex Attractants)
      178A96NLP2 (Dodecanol)
      33956-49-9 (8,10-dodecadien-1-ol)
    • Publication Date:
      Date Created: 20211111 Date Completed: 20211215 Latest Revision: 20220815
    • Publication Date:
      20240829
    • Accession Number:
      PMC8642345
    • Accession Number:
      10.1007/s10886-021-01316-4
    • Accession Number:
      34762210