HLE-inhibitory alkaloids with a polyketide skeleton from the marine-derived fungus Coniothyrium cereale

J Nat Prod. 2011 Oct 28;74(10):2282-5. doi: 10.1021/np2004227. Epub 2011 Sep 16.

Abstract

The marine endophytic fungus Coniothyrium cereale produces the structurally unusual polyketide-type alkaloids (-)-cereolactam (1) and (-)-cereoaldomine (3), incorporating a lactam and an imine functionality, respectively, as well as the related metabolite (-)-trypethelone (2). Compounds 1 and 3 showed selective inhibition of human leukocyte elastase with IC50 values of 9.28 and 3.01 μM, respectively. Compound 2 was found to be inhibitory toward Mycobacterium phlei, Staphylococcus aureus, and Escherichia coli and also cytotoxic against mouse fibroblast cells (IC50=7.5 μM).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkaloids / chemistry
  • Alkaloids / isolation & purification*
  • Alkaloids / pharmacology*
  • Animals
  • Ascomycota / chemistry*
  • Escherichia coli / drug effects
  • Fibroblasts
  • Humans
  • Inhibitory Concentration 50
  • Leukocyte Elastase / antagonists & inhibitors*
  • Marine Biology
  • Mice
  • Molecular Structure
  • Mycobacterium phlei / drug effects
  • Polyketides / chemistry
  • Polyketides / isolation & purification*
  • Polyketides / pharmacology*
  • Staphylococcus aureus / drug effects
  • Stereoisomerism

Substances

  • Alkaloids
  • Polyketides
  • cereolactam
  • Leukocyte Elastase