Issue 11, 2003

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

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 MSn ion-trap ESI mass spectrometry.

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

Article information

Article type
Paper
Submitted
28 Feb 2003
Accepted
27 Mar 2003
First published
15 Apr 2003

Org. Biomol. Chem., 2003,1, 1856-1862

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

R. J. Capon, C. Skene, M. Stewart, J. Ford, R. A. J. O'Hair, L. Williams, E. Lacey, J. H. Gill, K. Heiland and T. Friedel, Org. Biomol. Chem., 2003, 1, 1856 DOI: 10.1039/B302306K

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