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

Capon, Robert J., Skene, Colin, Stewart, Michael, Ford, Joanne, O'Hair, Richard A. J., Williams, Leisha, Lacey, Ernest, Gill, Jennifer H., Heiland, Kirstin and Friedel, Thomas (2003) Aspergillicins A-E: five novel depsipeptides from the marine-derived fungus Aspergillus carneus. Organic & Biomolecular Chemistry, 1 11: 1856-1862. doi:10.1039/b302306k


Author Capon, Robert J.
Skene, Colin
Stewart, Michael
Ford, Joanne
O'Hair, Richard A. J.
Williams, Leisha
Lacey, Ernest
Gill, Jennifer H.
Heiland, Kirstin
Friedel, Thomas
Title Aspergillicins A-E: five novel depsipeptides from the marine-derived fungus Aspergillus carneus
Journal name Organic & Biomolecular Chemistry   Check publisher's open access policy
ISSN 1477-0520
Publication date 2003
Sub-type Article (original research)
DOI 10.1039/b302306k
Open Access Status Not Open Access
Volume 1
Issue 11
Start page 1856
End page 1862
Total pages 7
Place of publication Cambridge, United Kingdom
Publisher Royal Society of Chemistry
Language eng
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.
Keyword Chemistry, Organic
Constituent Amino-acids
X-ray-analysis
Absolute-configuration
Penicillium-roqueforti
Mass-spectrometry
Peptide
Marcfortine
Lc/ms
Q-Index Code C1
Q-Index Status Provisional Code
Institutional Status Unknown

Document type: Journal Article
Sub-type: Article (original research)
Collections: Excellence in Research Australia (ERA) - Collection
Institute for Molecular Bioscience - Publications
 
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Created: Mon, 13 Aug 2007, 13:35:08 EST