Semisynthesis and antifeedant activity of new derivatives of a dihydro-β-agarofuran from Parnassia wightiana

Int J Mol Sci. 2013 Sep 26;14(10):19484-93. doi: 10.3390/ijms141019484.

Abstract

Five new derivatives (2-6) were semi-synthesized using compound 1, a dihydro-β-agarofuran sesquiterpene with C-2 ketone obtained from Parnassia wightiana, as the starting material by acylation, oxidation, reduction, esterification, and amination, respectively. Structures of 2-6 were confirmed by 1D- and 2D-NMR and HR-ESI-MS spectra. In addition, antifeedant activities of these compounds (1-6) were tested against the 3rd-instar larvae of Mythimna separata. Antifeedant effects of compounds 2 and 4 were greater than the parent compound 1 whereas other compounds exhibited low to no feeding deterrent effects against third instar M. separata larvae in lab bioassays. Therefore, our results suggest that acylated and reduced derivatives at C-8 and C-2, respectively, of 1 may improve the antifeeding effect. This preliminary information will be useful in designing new insect control agents against M. separata and other important pests.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Insect Control / methods
  • Larva / drug effects*
  • Moths / drug effects*
  • Plant Extracts / chemistry*
  • Plant Extracts / pharmacology*
  • Sesquiterpenes / chemistry*
  • Sesquiterpenes / pharmacology*

Substances

  • Plant Extracts
  • Sesquiterpenes
  • dihydroagarofuran