New nemadectin congeners with acaricidal and nematocidal activity from Streptomyces microflavus neau3 Y-3

Bioorg Med Chem Lett. 2013 Oct 15;23(20):5710-3. doi: 10.1016/j.bmcl.2013.08.002. Epub 2013 Aug 11.

Abstract

Two nemadectin congeners 1 and 2 were isolated from the fermentation broth of a mutant strain (Y-3) of Streptomyces microflavus neau3. Their structures were determined on the basis of extensive spectroscopic analysis and comparison with data from the literature. Compound 2 possessed a 5-membered ring lactone that is unprecedented among known milbemycins and avermectins. Both compounds 1 and 2 exhibited potent acaricidal activity and nematocidal activity. Especially, compound 2 demonstrated impressive acaricidal activity against adult mites with an IC50 of 2.3±0.9 μg/mL and mite eggs with an IC50 of 17.5±2.1 μg/mL and nematocidal activity against Caenorhabditis elegans with an IC50 of 0.7±0.2 μg/mL, which are higher than those of nemadectin and the known commercial acaricide and nematocide milbemycin A3/A4.

Keywords: Acaricidal activity; Nemadectin congeners; Nematocidal activity; Streptomyces microflavus neau3.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acaricides / chemistry
  • Acaricides / isolation & purification
  • Acaricides / toxicity
  • Animals
  • Antinematodal Agents / chemistry
  • Antinematodal Agents / isolation & purification
  • Antinematodal Agents / toxicity
  • Caenorhabditis elegans / drug effects
  • Macrolides / chemistry*
  • Macrolides / isolation & purification
  • Macrolides / toxicity
  • Magnetic Resonance Spectroscopy
  • Mites / drug effects
  • Molecular Conformation
  • Streptomyces / chemistry*
  • Streptomyces / metabolism

Substances

  • Acaricides
  • Antinematodal Agents
  • Macrolides
  • moxidectin