Cottoquinazoline A and Cotteslosins A and B, Metabolites from an Australian Marine-Derived Strain of Aspergillus versicolor

• Published in: Journal of natural products (Washington, D.C.) Vol. 72; no. 4; pp. 666 - 670
• Main Authors: Fremlin, Leith J, Piggott, Andrew M, Lacey, Ernest, Capon, Robert. J
• Format: Journal Article
• Language: English
• Published: Northbrook, IL American Chemical Society and American Society of Pharmacognosy 24-04-2009; American Society of Pharmacognosy
• Subjects: antibacterial properties; Antineoplastic Agents - chemistry; Antineoplastic Agents - isolation & purification; Antineoplastic Agents - pharmacology; Aspergillus - chemistry; Aspergillus versicolor; Australia; Biological and medical sciences; chemical structure; cyclic peptides; cytotoxicity; Drug Screening Assays, Antitumor; General pharmacology; heterocyclic compounds; Humans; isolation; Marine Biology; marine fungi; Medical sciences; Microbial Sensitivity Tests; Molecular Structure; Nuclear Magnetic Resonance, Biomolecular; Peptides, Cyclic - chemistry; Peptides, Cyclic - isolation & purification; Peptides, Cyclic - pharmacology; Pharmacognosy. Homeopathy. Health food; Pharmacology. Drug treatments; phenols; Quinazolines - chemistry; Quinazolines - isolation & purification; Quinazolines - pharmacology; secondary metabolites; Sterigmatocystin - chemistry; Sterigmatocystin - isolation & purification; Australia; Oceania; Peptides; Angular nitrogen heterocycle; Metabolite; Cyclic peptides; Lactam; Cytotoxicity; Fungi; Marine environment; Alkaloid; Fungi Imperfecti; Mammary gland; Valine derivatives; Tumor cell; Human; Aspergillus versicolor; Melanoma; Polycyclic compound; In vitro; Biological activity; Cell line; Microbial origin; Absolute configuration; Isolation; Antibacterial agent; Prostate; Pentapeptide; Structural analysis
• ISSN: 0163-3864; 1520-6025
• DOI: 10.1021/np800777f

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 C3 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.