Linoleic acid and stearic acid are biosynthetic precursors of (7Z,10Z)-7,10-hexadecadienal, the major component of the sex pheromone of Chilecomadia valdiviana (Lepidoptera: Cossidae).

Heidy Herrera,Wilson Barros-Parada,Jan Bergmann,J Joe Hull

doi:10.1371/journal.pone.0215769

Heidy Herrera, Wilson Barros-Parada + Show 2 more

Open Access

https://doi.org/10.1371/journal.pone.0215769

Copy DOI

Abstract

The main pheromone compound of Chilecomadia valdiviana (Lepidoptera: Cossidae) has been recently identified as (7Z,10Z)-7,10-hexadecadienal. The biosynthesis of this pheromone compound showing attributes of both Type I and Type II lepidopteran pheromones was studied by the topical application of isotope-labeled fatty acids to the pheromone gland and subsequent analysis of the gland contents (pheromone compounds and fatty acyl compounds) by gas chromatography-mass spectrometry. The deuterium label of D11-linoleic acid was incorporated into the pheromone compound and its putative acyl precursor (7Z,10Z)-7,10-hexadecadienoate, demonstrating that the pheromone compound is biosynthesized from linoleic acid by chain-shortening and further functional group transformation. Furthermore, the deuterium label of D3-stearic acid was also incorporated into the pheromone compound, which indicates that the pheromone can be synthesized de novo by C. valdiviana, as is the case for Type I lepidopteran pheromone compounds.

Highlights

The sex pheromones of about 600 species of Lepidoptera have been identified [1,2] and according to their structure, they are often classified as “Type I” or “Type II” pheromones
The first step in this transformation is the chain-shortening of linoleic acid by two carbons, as was evidenced by the appearance of deuterium-labeled Z7,Z10-16:COOMe among the fatty acyl compounds in the pheromone gland after treatment with D11-linoleic acid
We have shown that linoleic acid is a direct precursor for the biosynthesis of Z7,Z10-16:Ald in C. valdiviana

Summary

Introduction

The sex pheromones of about 600 species of Lepidoptera have been identified [1,2] and according to their structure, they are often classified as “Type I” or “Type II” pheromones. The common feature of Type I pheromones, produced by the majority of species, is an unbranched chain of 10–18 carbon atoms possessing a terminal oxygenated functional group (alcohol, aldehyde, or acetate) and 0–3 double bonds along the chain, while Type II pheromones, produced by a number of species in the families Arctiidae, Geometridae, Lymantriidae, and Noctuidae, are straight-chain, polyunsaturated hydrocarbons and their epoxy derivatives [1,3].

Objectives

Methods

Discussion

Conclusion