Halogenated anthraquinones from the marine-derived fungus Aspergillus sp. SCSIO F063

J Nat Prod. 2012 Jul 27;75(7):1346-52. doi: 10.1021/np3002699. Epub 2012 Jun 15.

Abstract

Metabolomic investigations focusing on the marine-derived fungus Aspergillus sp. SCSIO F063 have unveiled seven new chlorinated anthraquinones (1-7) related to averantin, together with five known analogues (11-15) when the fungus was fermented using sea salt-containing potato dextrose broth. Through the addition of sodium bromide to the broth, two new brominated anthraquinones (8, 9) and one new nonhalogenated anthraquinone (10) were obtained from the fungal mycelia. Their structures were elucidated by extensive spectroscopic analyses including MS and 1D and 2D NMR data. One metabolite, 6-O-methyl-7-chloroaveratin (2), displayed inhibition activity against three human tumor cell lines, SF-268, MCF-7, and NCI-H460, with IC(50) values of 7.11, 6.64, and 7.42 μM, respectively.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anthraquinones / chemistry
  • Anthraquinones / isolation & purification*
  • Anthraquinones / pharmacology
  • Aspergillus / chemistry*
  • Bacillus subtilis / drug effects
  • Bacillus thuringiensis / drug effects
  • Cell Line, Tumor
  • Drug Screening Assays, Antitumor
  • Humans
  • Hydrocarbons, Chlorinated / chemistry
  • Hydrocarbons, Chlorinated / isolation & purification*
  • Hydrocarbons, Chlorinated / pharmacology
  • Inhibitory Concentration 50
  • Marine Biology
  • Microbial Sensitivity Tests
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Staphylococcus aureus / drug effects

Substances

  • Anthraquinones
  • Hydrocarbons, Chlorinated