Matrine-Type Alkaloids with Anti-Tomato Spotted Wilt Virus Activity from the Root of Sophora tonkinensis Gagnep

J Agric Food Chem. 2023 Mar 15;71(10):4394-4407. doi: 10.1021/acs.jafc.2c09003. Epub 2023 Feb 28.

Abstract

As a continuation of our research on the development of pesticide active quinolizidine alkaloids (QAs) from the family Fabaceae, the chemical constituents of the root of Sophora tonkinensis Gagnep. were systematically investigated. Seventeen new matrine-type alkaloids (1-17), including one new naturally occurring compound (17), along with 20 known ones were isolated from the EtOH extract of S. tonkinensis. Notably, compound 5 possessed an unprecedented 6/6/5/4/6/6 hexacyclic system. Their structures were confirmed via comprehensive spectroscopic data analysis (IR, UV, NMR, HRESIMS), ECD calculation, and X-ray crystallography. Biological tests indicated that compounds 1, 4, 10, 12, 13, and 30 displayed significant anti-tomato spotted wilt virus (TSWV) activities compared with the positive control ningnanmycin. Moreover, compound 12 strongly inhibited the expression of the TSWV N, NSs, and NSm genes and TSWV NSs protein in plant host. Furthermore, compounds 4, 10, 12, 20, and 22 exhibited moderate insecticidal activities against TSWV thrip vector (Frankliniella occidentalis).

Keywords: Sophora tonkinensis Gagnep.; anti-TSWV; matrine-type alkaloids.

MeSH terms

  • Animals
  • Antiviral Agents / chemistry
  • Antiviral Agents / pharmacology
  • Crystallography, X-Ray
  • Insecticides / chemistry
  • Insecticides / pharmacology
  • Matrines / chemistry
  • Matrines / pharmacology
  • Models, Molecular
  • Molecular Structure
  • Plant Roots
  • Sophora*
  • Spectrophotometry
  • Tospovirus* / drug effects
  • Viral Nonstructural Proteins / genetics
  • Virus Activation / drug effects

Substances

  • Matrines
  • Antiviral Agents
  • Insecticides
  • Viral Nonstructural Proteins