Chlorinated coumarins from the polypore mushroom Fomitopsis officinalis and their activity against Mycobacterium tuberculosis

J Nat Prod. 2013 Oct 25;76(10):1916-22. doi: 10.1021/np400497f. Epub 2013 Oct 2.

Abstract

An EtOH extract of the polypore mushroom Fomitopsis officinalis afforded two new naturally occurring chlorinated coumarins, which were identified as the previously synthesized compounds 6-chloro-4-phenyl-2H-chromen-2-one (1) and ethyl 6-chloro-2-oxo-4-phenyl-2H-chromen-3-carboxylate (2). The structures of the two isolates were deduced by ab initio spectroscopic methods and confirmed by chemical synthesis. In addition, an analogue of each was synthesized as 7-chloro-4-phenyl-2H-chromen-2-one (3) and ethyl 7-chloro-2-oxo-4-phenyl-2H-chromen-3-carboxylate (4). All four compounds were characterized physicochemically, and their antimicrobial activity profiles revealed a narrow spectrum of activity with lowest MICs against the Mycobacterium tuberculosis complex.

MeSH terms

  • Agaricales / chemistry*
  • Animals
  • Antitubercular Agents / chemistry
  • Antitubercular Agents / isolation & purification*
  • Antitubercular Agents / pharmacology*
  • Chlorocebus aethiops
  • Coumarins / chemistry
  • Coumarins / isolation & purification*
  • Coumarins / pharmacology*
  • Cytotoxins / chemistry
  • Cytotoxins / isolation & purification*
  • Cytotoxins / pharmacology*
  • Hydrocarbons, Chlorinated / chemistry
  • Hydrocarbons, Chlorinated / isolation & purification*
  • Hydrocarbons, Chlorinated / pharmacology*
  • Microbial Sensitivity Tests
  • Molecular Structure
  • Mycobacterium tuberculosis / drug effects*
  • Nuclear Magnetic Resonance, Biomolecular
  • Vero Cells

Substances

  • 6-chloro-4-phenyl-2H-chromen-2-one
  • Antitubercular Agents
  • Coumarins
  • Cytotoxins
  • Hydrocarbons, Chlorinated
  • ethyl 6-chloro-2-oxo-4-phenyl-2H-chromen-3-carboxylate