Polyketides from the marine-derived fungus Ascochyta salicorniae and their potential to inhibit protein phosphatases

Org Biomol Chem. 2006 Jun 7;4(11):2233-40. doi: 10.1039/b601386d. Epub 2006 May 3.


Chemical investigation of the marine fungus Ascochyta salicorniae led to the isolation of two new epimeric compounds, ascolactones A (1) and B (2), in addition to the structurally-related polyketides hyalopyrone (3), ascochitine (4), ascochital (5) and ascosalipyrone (6). The absolute configurations of the epimeric compounds 1 and 2 were assigned as (1R,9R) and (1S,9R), respectively, through simulation of the chiroptical properties using quantum-chemical CD calculations, and chiral GC-MS subsequent to oxidative cleavage (Baeyer-Villiger oxidation) of the side chain. In silico screening using the PASS software identified some of the A. salicorniae compounds (1-6) as potential inhibitors of protein phosphatases. Compound was found to inhibit the enzymatic activity of MPtpB with an IC(50) value of 11.5 microM.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Ascomycota / chemistry*
  • Circular Dichroism
  • Enzyme Inhibitors / chemistry
  • Enzyme Inhibitors / isolation & purification*
  • Enzyme Inhibitors / pharmacology*
  • Macrolides / chemistry
  • Macrolides / isolation & purification*
  • Macrolides / pharmacology*
  • Nuclear Magnetic Resonance, Biomolecular
  • Phosphoprotein Phosphatases / antagonists & inhibitors*


  • Enzyme Inhibitors
  • Macrolides
  • Phosphoprotein Phosphatases