Discovery and properties of novel analogues of the aphid pheromones nepetalactone and nepetalactol.

Autor: Lu Y; Shanghai Key Laboratory of Chemical Biology, School of Pharmacy, East China University of Science and Technology, Shanghai, China., Li Z; Shanghai Key Laboratory of Chemical Biology, School of Pharmacy, East China University of Science and Technology, Shanghai, China.; State Key Laboratory of Bioreactor Engineering, East China University of Science and Technology, Shanghai, China., Shao X; Shanghai Key Laboratory of Chemical Biology, School of Pharmacy, East China University of Science and Technology, Shanghai, China.; State Key Laboratory of Bioreactor Engineering, East China University of Science and Technology, Shanghai, China.; Shanghai Frontier Science Research Base of Optogenetic Techniques for Cell Metabolism, School of Pharmacy, East China University of Science and Technology, Shanghai, China.; Engineering Research Center of Pharmaceutical Process Chemistry, Ministry of Education, School of Pharmacy, East China University of Science and Technology, Shanghai, China., Maienfisch P; Shanghai Key Laboratory of Chemical Biology, School of Pharmacy, East China University of Science and Technology, Shanghai, China.; CreInSol Consulting and Biocontrols, Rodersdorf, Switzerland.
Jazyk: angličtina
Zdroj: Pest management science [Pest Manag Sci] 2024 Jun; Vol. 80 (6), pp. 2773-2784. Date of Electronic Publication: 2024 Feb 02.
DOI: 10.1002/ps.7984
Abstrakt: Background: Pheromones have unique advantages for pest control. Current aphid pheromone research focuses on alarm and sex pheromones. However, practical applications are limited so far, as (E)-β-farnesene has only been investigated to a small extent as an alarm pheromone and only male aphids are targeted by sex pheromones. Previous literature reports electrophysiological responses and repellent behavior of asexual aphids to nepetalactone (1B), therefore our objective was to modify nepetalactone's structure to identify key fragments responsible for repellent effects, as guidance for subsequent modifications and further investigation.
Results: In this study, seven derivatives were designed and synthesized based on nepetalactol (1A) and nepetalactone (1B) as lead compounds. Free-choice tests, conducted using cowpea aphids (Aphis craccivora), revealed that the lactone moiety was crucial for the repellent activity, and the removal of the carbonyl group eliminated the repelling effect. Compound (±)1I, an analogue of nepetalactone (1B), demonstrated a significantly higher repellent value than nepetalactone (1B) at three different concentrations, and even at 0.1 mg/mL it maintained a considerable repellent effect (26.5%). Electrostatic potential and density functional theory calculations supported the importance of the carbonyl group for the repellent effects.
Conclusion: The newly discovered para-pheromone (±)1I shows improved repellent effects and potential for development as a novel biological control agent. Based on our innovative findings, analogues with improved efficacy and properties can be designed and prepared. Our research contributes to understanding the effects of structural modifications on pheromone activity and properties, which is crucial for exploring novel pheromone-based products for crop protection. © 2024 Society of Chemical Industry.
(© 2024 Society of Chemical Industry.)
Databáze: MEDLINE
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