title: An indole-containing dauer pheromone component with unusual dauer inhibitory activity at higher concentrations.
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.
authors: Department of Biological Chemistry and Molecular Pharmacology, Harvard Medical School, 240 Longwood Avenue, Boston, Massachusetts 02115, USA.
authors: Rebecca A
authors: RA
authors: Butcher
authors: Justin R
authors: JR
authors: Ragains
authors: Jon
authors: J
authors: Clardy
mesh_terms: D000818:Animals; D017173:Caenorhabditis elegans / Q000737:chemistry* / Q000254:growth & development / Q000502:physiology; D006601:Hexoses / Q000737:chemistry* / Q000378:metabolism* / Q000494:pharmacology; D007211:Indoles / Q000737:chemistry* / Q000378:metabolism / Q000494:pharmacology; D007814:Larva / Q000254:growth & development; D015394:Molecular Structure; D010675:Pheromones / Q000737:chemistry* / Q000378:metabolism* / Q000494:pharmacology
chemical_list: D006601:Hexoses; D007211:Indoles; D010675:Pheromones; C542711:indolecarboxyl-ascaroside C5