First semi-synthetic preparation of sex pheromones

Abstract

Here we describe the first construction of a genetically modified plant (GMP) with the ability to produce moth sex pheromone precursors. Previously prepared (Svatoš et al., Czech Patent Appl. 2000/0125) N. tabacum GMP transformed with a plasmid encoding cabbage looper moth (Trichoplusia ni, Hübner, Lepidoptera, Noctuidae) acyl-CoA Δ¹¹-(Z)-desaturase (Knipple et al., Proc. Natl. Acad. Sci. USA, 1998, 95, 15287) showed a substantial presence (ca. 6%) of the potential pheromone precursor, methyl (11Z)-hexadec-11-enoate (1). The ester 1 was isolated in bulk (6.5% of extracted lipids) from a greenhouse cultivated transgenic tobacco and the corresponding acetate, which are principal components of a large number of sex pheromones, was semi-synthetically prepared from the in planta produced pheromone precursor. The attractiveness of the prepared blends for moth, Mamestra brassica was proved in field trials.