Cottoquinazoline A and cotteslosins A and B, metabolites from an Australian marine-derived strain of Aspergillus versicolor.
An Australian marine-derived isolate of Aspergillus versicolor (MST-MF495) yielded the known fungal metabolites sterigmatocystin, violaceol I, violaceol II, diorcinol, (-)-cyclopenol, and viridicatol, along with a new alkaloid, cottoquinazoline A (1), and two new cyclopentapeptides, cotteslosins A (2) and B (3). Structures for 1-3 and the known compounds were determined by spectroscopic analysis. The absolute configurations of 1-3 were addressed by chemical degradation and application of the C(3) Marfey's method. The use of "cellophane raft" high-nutrient media as a device for up-regulating secondary metabolite diversity in marine-derived fungi is discussed. The antibacterial properties displayed by A. versicolor (MST-MF495) were attributed to the phenols violaceol I, violaceol II, and diorcinol, while cotteslosins 2 and 3 were identified as weak cytotoxic agents.
Fremlin
Leith J
LJ
Institute for Molecular Bioscience, The University of Queensland, St Lucia, QLD, Australia.
Piggott
Andrew M
AM
Lacey
Ernest
E
Capon
Robert J
RJ
D000970:Antineoplastic Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D001230:Aspergillus / Q000737:chemistry*; D001315:Australia; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D008386:Marine Biology; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D010456:Peptides, Cyclic / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D011799:Quinazolines / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D013241:Sterigmatocystin / Q000737:chemistry / Q000302:isolation & purification
D000970:Antineoplastic Agents; D010456:Peptides, Cyclic; D011799:Quinazolines; C540536:cotteslosin A; C540537:cotteslosin B; C540535:cottoquinazoline A; D013241:Sterigmatocystin