Design, synthesis, and evaluation of novel arecoline-linked amino acid derivatives for insecticidal and antifungal activities

Sci Rep. 2024 Apr 24;14(1):9392. doi: 10.1038/s41598-024-60053-2.

Abstract

A series of arecoline derivatives with amino acid moieties were designed and synthesised using an acylamide condensation strategy, taking arecoline as the foundational structure. The insecticidal efficacy of these compounds against Aphis craccivora and Tetranychus cinnabarinus was evaluated. Notably, derivatives 3h and 3i demonstrated superior insecticidal activity compared with arecoline. Additionally, 3h and 3i showed good fungicidal effectiveness against two types of plant fungi. Moreover, molecular docking analyses suggested that 3h and 3i could affect the nervous systems of A. craccivora and T. cinnabarinus by binding to neuronal nicotinic acetylcholine receptors. These findings suggest that compounds 3h and 3i represent promising leads for further development in insecticide and fungicide research.

Keywords: Arecoline; Derivatives; Fungicidal activity; Insecticidal activity; Molecular docking.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amino Acids* / chemistry
  • Animals
  • Antifungal Agents* / chemical synthesis
  • Antifungal Agents* / chemistry
  • Antifungal Agents* / pharmacology
  • Aphids / drug effects
  • Drug Design*
  • Insecticides* / chemical synthesis
  • Insecticides* / chemistry
  • Insecticides* / pharmacology
  • Microbial Sensitivity Tests
  • Molecular Docking Simulation*
  • Receptors, Nicotinic / chemistry
  • Receptors, Nicotinic / metabolism
  • Structure-Activity Relationship
  • Tetranychidae / drug effects

Substances

  • Insecticides
  • Antifungal Agents
  • Amino Acids
  • Receptors, Nicotinic