Evaluation of andrographolide-based analogs derived from Andrographis paniculata against Mythimna separata Walker and Tetranychus cinnabarinus Boisduval

Bioorg Chem. 2019 May:86:28-33. doi: 10.1016/j.bioorg.2019.01.020. Epub 2019 Jan 17.

Abstract

To discover new natural-product-based pesticides, we structurally modified andrographolide, a labdane diterpenoid isolated from Andrographis paniculata, and stereoselectively prepared a series of 12α-(substituted)benzylamino-14-deoxyandrographolide derivatives (I-V). Three-dimensional structures of compounds 3c, 3d, IIIa and IIIb were further determined by single-crystal X-ray diffraction. Compounds IIa (R1 = n-C3H7, R2 = PhCH2) exhibited more promising insecticidal activity against Mythimna separata than toosendanin. Compounds 3a (R1 = H), Ib (R1 = H, R2 = 4-ClPhCH2), and IVa (R1 = 4-ClPh, R2 = PhCH2) showed potent acaricidal activity against Tetranychus cinnabarinus.

Keywords: Andrographis paniculata; Andrographolide; Pesticidal activity; Secondary metabolite; Structural modification.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Andrographis / chemistry*
  • Animals
  • Crystallography, X-Ray
  • Diterpenes / chemistry
  • Diterpenes / isolation & purification
  • Diterpenes / pharmacology*
  • Dose-Response Relationship, Drug
  • Models, Molecular
  • Molecular Structure
  • Moths / drug effects*
  • Pesticides / chemistry
  • Pesticides / isolation & purification
  • Pesticides / pharmacology*
  • Structure-Activity Relationship
  • Tetranychidae / drug effects*

Substances

  • Diterpenes
  • Pesticides
  • andrographolide