Aspergillicins A-E: five novel depsipeptides from the marine-derived fungus Aspergillus carneus

Org Biomol Chem. 2003 Jun 7;1(11):1856-62. doi: 10.1039/b302306k.

Abstract

A search for new antiparasitic agents from a strain of the fungus Aspergillus carneus isolated from an estuarine sediment collected in Tasmania, Australia, yielded the known terrestrial fungal metabolite marcfortine A (1) as an exceptionally potent antiparasitic agent. This study also yielded a series of new depsipeptides, aspergillicins A-E (2-6) and the known terrestrial fungal metabolite acyl aszonalenin (7). Marcfortine A (1) and acyl aszonalenin (7) were identified by spectroscopic analysis, with comparison to literature data. Complete stereostructures were assigned to aspergillicins A-E (2-6) on the basis of detailed spectroscopic analysis, together with ESIMS analysis of the free amino acids generated by acid hydrolysis, and HPLC analysis of Marfey derivatives prepared from the acid hydrolysate. The peptide amino acid sequence for all aspergillicins was unambiguously assigned by MS(n) ion-trap ESI mass spectrometry.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amino Acid Sequence
  • Antiparasitic Agents / chemistry
  • Antiparasitic Agents / isolation & purification
  • Aspergillus / chemistry*
  • Indolizines / isolation & purification
  • Molecular Conformation
  • Molecular Sequence Data
  • Nuclear Magnetic Resonance, Biomolecular
  • Peptides, Cyclic / chemistry*
  • Peptides, Cyclic / isolation & purification
  • Peptides, Cyclic / pharmacology
  • Sequence Analysis, Protein / methods
  • Spectrometry, Mass, Electrospray Ionization
  • Spiro Compounds / isolation & purification

Substances

  • Antiparasitic Agents
  • Indolizines
  • Peptides, Cyclic
  • Spiro Compounds
  • marcfortine A