Natural-product-based pesticides: Semisynthesis, structural elucidation, and evaluation of new cholesterol-matrine conjugates as pesticidal agents

Bioorg Med Chem Lett. 2021 Oct 15:50:128350. doi: 10.1016/j.bmcl.2021.128350. Epub 2021 Aug 31.

Abstract

To develop new potential pesticide candidates from low value-added natural bioactive products, a series of new cholesterol-matrine conjugates (I(a-e)-IV(a-e)) were prepared from two lead compounds cholesterol and matrine. Against Mythimna separata Walker, compound IVa exhibited 3.0 and 2.6 folds promising insecticidal activity of cholesterol and matrine, respectively; against Aphis citricola Van der Goot, compound IVd showed 4.3 and 2.2 folds potent aphicidal activity of their precursors; notably, it also showed good control effects in the greenhouse; against Plutella xylostella Linnaeus at a dose of 20 μg/nymph, compound IIIe exhibited 2.8 and 2.0 folds oral toxicity of cholesterol and matrine, respectively. Compounds IIIe, IVd and IVe can be used as the leads for further structural optimization as the insecticidal and aphicidal agents.

Keywords: Cholesterol; Control efficiency; Matrine; Pesticidal activity; Synthesis.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkaloids / chemistry*
  • Animals
  • Biological Products / chemistry*
  • Cholesterol / chemistry*
  • Drug Design
  • Insecta / drug effects*
  • Insecticides / chemical synthesis*
  • Insecticides / chemistry
  • Insecticides / pharmacology*
  • Larva / drug effects
  • Matrines
  • Models, Molecular
  • Molecular Structure
  • Pupa / drug effects
  • Quinolizines / chemistry*
  • Structure-Activity Relationship

Substances

  • Alkaloids
  • Biological Products
  • Insecticides
  • Quinolizines
  • Cholesterol
  • Matrines