Cottoquinazoline A and cotteslosins A and B, metabolites from an Australian marine-derived strain of Aspergillus versicolor

J Nat Prod. 2009 Apr;72(4):666-70. doi: 10.1021/np800777f.

Abstract

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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / isolation & purification*
  • Antineoplastic Agents / pharmacology
  • Aspergillus / chemistry*
  • Australia
  • Drug Screening Assays, Antitumor
  • Humans
  • Marine Biology
  • Microbial Sensitivity Tests
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Peptides, Cyclic / chemistry
  • Peptides, Cyclic / isolation & purification*
  • Peptides, Cyclic / pharmacology
  • Quinazolines / chemistry
  • Quinazolines / isolation & purification*
  • Quinazolines / pharmacology
  • Sterigmatocystin / chemistry
  • Sterigmatocystin / isolation & purification

Substances

  • Antineoplastic Agents
  • Peptides, Cyclic
  • Quinazolines
  • cotteslosin A
  • cotteslosin B
  • cottoquinazoline A
  • Sterigmatocystin