Antifeedant C20 diterpene alkaloids

Chem Biodivers. 2004 Sep;1(9):1327-35. doi: 10.1002/cbdv.200490095.

Abstract

We have tested the insect antifeedant and toxic activity of 21 C20 diterpenoid alkaloids on Spodoptera littoralis and Leptinotarsa decemlineata. The antifeedant effects of the test compounds were structure- and species-dependent. The most active antifeedants to L. decemlineata and S. littoralis were the rearranged form of hetisine (20; EC50 = 1.7 microg/cm2) and 19-oxodihydroatisine (9; EC50 = 0.1 microg/cm2), resp. Glandulosine (8) moderately affected orally injected S. littoralis larvae. A few compounds (13-oxocardiopetamine (4), 9, and atisinium chloride (13)) had cytotoxic effects to insect-derived Sf9 cells with varying degrees of selectivity with respect to mammalian CHO cells. Compounds 4 and 15,22-O-diacetyl-19-oxodihydroatisine (10) increased Trypanosoma cruzi mortality. Our results support the plant protective role of C20 diterpenoid alkaloids and open a new field for parasite control strategies.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkaloids / chemistry*
  • Alkaloids / isolation & purification
  • Alkaloids / pharmacology*
  • Animals
  • CHO Cells
  • Cell Survival / drug effects
  • Cell Survival / physiology
  • Cricetinae
  • Cricetulus
  • Diterpenes / chemistry*
  • Diterpenes / isolation & purification
  • Diterpenes / pharmacology*
  • Feeding Behavior / drug effects
  • Feeding Behavior / physiology
  • Female
  • Insecta / drug effects
  • Insecta / parasitology
  • Pest Control, Biological / methods

Substances

  • Alkaloids
  • Diterpenes