A novel ergot alkaloid as a 5-HT(1A) inhibitor produced by Dicyma sp

J Med Chem. 2003 Nov 20;46(24):5117-20. doi: 10.1021/jm0341204.

Abstract

In the course of a search for small-molecule inhibitors of 5-hydroxytryptamine receptors we have identified a novel ergoline derivative (1) from the fungal culture of Dicyma sp. This compound has a pK(i) of 10.2 versus the 5-hydroxytryptamine(1A) receptor subtype. The structure was elucidated by extensive NMR spectroscopy and mass spectrometry.

MeSH terms

  • Animals
  • Ascomycota / chemistry*
  • Brain / drug effects
  • Brain / metabolism
  • Brain / ultrastructure
  • Cell Membrane / drug effects
  • Cell Membrane / metabolism
  • Ergolines / chemistry
  • Ergolines / isolation & purification*
  • Ergolines / pharmacology
  • Ergot Alkaloids / chemistry
  • Ergot Alkaloids / isolation & purification*
  • Ergot Alkaloids / pharmacology
  • Guanosine 5'-O-(3-Thiotriphosphate) / metabolism
  • In Vitro Techniques
  • Magnetic Resonance Spectroscopy
  • Radioligand Assay
  • Receptor, Serotonin, 5-HT1A / drug effects*
  • Receptor, Serotonin, 5-HT1A / metabolism
  • Serotonin Antagonists / chemistry
  • Serotonin Antagonists / isolation & purification*
  • Serotonin Antagonists / pharmacology

Substances

  • Ergolines
  • Ergot Alkaloids
  • N-(8'-hydroxy-2'-methyl-5'-(2-methylpropyl)-3',6'-dioxo-7'-(phenylmethyl)oxazolidino(2,3-c)piperazin-2'-yl) 6-methylergoline-8-carboxamide
  • Serotonin Antagonists
  • Receptor, Serotonin, 5-HT1A
  • Guanosine 5'-O-(3-Thiotriphosphate)