Pyrethrins are natural insecticides which accumulate in high concentrations in the flowers of Chrysanthemum cinerariaefolium (the pyrethrum flower). Natural pyrethrins, as well as dried flower powders, have been used to control household pests, but have been replaced by synthetic pyrethroids, which are more stable, have greater insecticidal efficacy and are cheaper to produce. However, recent requirements for safe and environmentally-friendly pesticides encourage the use of natural pyrethrins. The biosynthesis of pyrethrins involves ester linkage formation between an acid moiety (chrysanthemoyl or pyrethroyl), synthesized via the mevalonic acid pathway from glucose and an alcohol (pyrethrolone). Pyrethrolone is generated from 12-oxophytodienoic acid, which originates from a-linolenic acid via the jasmonic acid biosynthetic cascade. The first four genes in this cascade encoding lipoxygenase 2 (LOX2), allene-oxide synthase (AOS), allene-oxide cyclase 2 (AOC2), and 12-oxophytodienoic acid reductase 3 (OPR3) were amplified from an Arabidopsis thaliana cDNA library, cloned in a purpose-built fungal multigene expression vector, and expressed in Aspergillus oryzae. Preliminary HPLC-MS/MS analysis of the transgenic fungus homogenate gave good evidence for the presence of 3-oxo-2-(2'-pentenyl)-cyclopentane-1-octanoic acid, the reduced derivative of 12-oxophytodienoic acid. 

Production of 12-oxophytodienoic acid derivative in the fungus <i>Aspergillus oryzae</i>: The first step in heterologous production of pyrethrins in fungi

248th National Meeting (2014)

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Production of 12-oxophytodienoic acid derivative in the fungus Aspergillus oryzae: The first step in heterologous production of pyrethrins in fungi