Aflaquinolones A-G: secondary metabolites from marine and fungicolous isolates of Aspergillus spp

J Nat Prod. 2012 Mar 23;75(3):464-72. doi: 10.1021/np200958r. Epub 2012 Feb 1.

Abstract

Seven new compounds (aflaquinolones A-G; 1-7) containing dihydroquinolin-2-one and terpenoid units have been isolated from two different fungal sources. Two of these metabolites (1 and 2) were obtained from a Hawaiian fungicolous isolate of Aspergillus sp. (section Flavipedes; MYC-2048 = NRRL 58570), while the others were obtained from a marine Aspergillus isolate (SF-5044) collected in Korea. The structures of these compounds were determined mainly by analysis of NMR and MS data. Relative and absolute configurations were assigned on the basis of NOESY data and (1)H NMR J-values, comparison of calculated and experimental ECD spectra, and analysis of a Mosher's ester derivative of 2. Several known compounds, including alantrypinone, aspochalasins I and J, methyl 3,4,5-trimethoxy-2((2-((3-pyridinylcarbonyl)amino)benzoyl)amino)benzoate, and trans-dehydrocurvularin were also encountered in the extract of the Hawaiian isolate.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Aspergillus / chemistry*
  • Democratic People's Republic of Korea
  • HL-60 Cells
  • Hawaii
  • Humans
  • Marine Biology
  • Microbial Sensitivity Tests
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Quinolones / chemistry
  • Quinolones / isolation & purification*
  • Staphylococcus aureus
  • Stereoisomerism

Substances

  • Quinolones