5-Hydroxyindole-type alkaloids, as Candida albicans isocitrate lyase inhibitors, from the tropical sponge Hyrtios sp

Bioorg Med Chem Lett. 2009 Feb 15;19(4):1051-3. doi: 10.1016/j.bmcl.2009.01.017. Epub 2009 Jan 11.

Abstract

Chemical investigations of the tropical marine sponge Hyrtios sp. have resulted in the isolation of a new alkaloid, 1-carboxy-6-hydroxy-3,4-dihydro-beta-carboline (1) together with the known metabolites, 6-hydroxy-3,4-dihydro-1-oxo-beta-carboline (2), 5-hydroxy-1H-indole-3-carboxylic acid methyl ester (3), serotonin (4), hyrtiosin A (5), 5-hydroxyindole-3-carbaldehyde (6), and hyrtiosin B (7). Their structures were elucidated on the basis of mass spectrometry and detailed 2D NMR spectroscopic data. Hyrtiosin B (7) displayed a potent inhibitory activity against isocitrate lyase (ICL) of Candida albicans with an IC(50) value of 89.0 microM.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Antifungal Agents / chemistry
  • Antifungal Agents / isolation & purification*
  • Antifungal Agents / pharmacology*
  • Candida albicans / enzymology*
  • Carbolines / chemistry
  • Carbolines / isolation & purification*
  • Carbolines / pharmacology
  • Indole Alkaloids / chemistry
  • Indole Alkaloids / isolation & purification*
  • Indole Alkaloids / pharmacology*
  • Isocitrate Lyase / antagonists & inhibitors*
  • Marine Biology
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Porifera / chemistry*

Substances

  • 1-carboxy-6-hydroxy-3,4-dihydro-beta-carboline
  • 5-hydroxyindole-3-carbaldehyde
  • Antifungal Agents
  • Carbolines
  • Indole Alkaloids
  • Isocitrate Lyase