Aspergillicins A-E: five novel depsipeptides from the marine-derived fungus Aspergillus carneus.
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.
Capon
Robert J
RJ
School of Chemistry, The University of Melbourne, Parkville, Victoria 3010, Australia.
Skene
Colin
C
Stewart
Michael
M
Ford
Joanne
J
O'Hair
Richard A J
RA
Williams
Leisha
L
Lacey
Ernest
E
Gill
Jennifer H
JH
Heiland
Kirstin
K
Friedel
Thomas
T
D000595:Amino Acid Sequence; D000977:Antiparasitic Agents / Q000737:chemistry / Q000302:isolation & purification; D001230:Aspergillus / Q000737:chemistry*; D007212:Indolizines / Q000302:isolation & purification; D008968:Molecular Conformation; D008969:Molecular Sequence Data; D019906:Nuclear Magnetic Resonance, Biomolecular; D010456:Peptides, Cyclic / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D020539:Sequence Analysis, Protein / Q000379:methods; D021241:Spectrometry, Mass, Electrospray Ionization; D013141:Spiro Compounds / Q000302:isolation & purification
D000977:Antiparasitic Agents; D007212:Indolizines; D010456:Peptides, Cyclic; D013141:Spiro Compounds; C103037:marcfortine A