An indole-containing dauer pheromone component with unusual dauer inhibitory activity at higher concentrations

Org Lett. 2009 Jul 16;11(14):3100-3. doi: 10.1021/ol901011c.

Abstract

In Caenorhabditis elegans, the dauer pheromone, which consists of a number of derivatives of the 3,6-dideoxysugar ascarylose, is the primary cue for entry into the stress-resistant, "nonaging" dauer larval stage. Here, using activity-guided fractionation and NMR-based structure elucidation, a structurally novel, indole-3-carboxyl-modified ascaroside is identified that promotes dauer formation at low nanomolar concentrations but inhibits dauer formation at higher concentrations.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Animals
  • Caenorhabditis elegans / chemistry*
  • Caenorhabditis elegans / growth & development
  • Caenorhabditis elegans / physiology
  • Hexoses / chemistry*
  • Hexoses / metabolism*
  • Hexoses / pharmacology
  • Indoles / chemistry*
  • Indoles / metabolism
  • Indoles / pharmacology
  • Larva / growth & development
  • Molecular Structure
  • Pheromones / chemistry*
  • Pheromones / metabolism*
  • Pheromones / pharmacology

Substances

  • Hexoses
  • Indoles
  • Pheromones
  • indolecarboxyl-ascaroside C5