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Issue 11, 2003
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Aspergillicins A–E: five novel depsipeptides from the marine-derived fungus Aspergillus carneus

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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

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Publication details

The article was received on 28 Feb 2003, accepted on 27 Mar 2003 and first published on 15 Apr 2003


Article type: Paper
DOI: 10.1039/B302306K
Citation: Org. Biomol. Chem., 2003,1, 1856-1862
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    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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