Potential cancer chemopreventive in vitro activities of monomeric xanthone derivatives from the marine algicolous fungus Monodictys putredinis

J Nat Prod. 2007 Mar;70(3):353-60. doi: 10.1021/np060505o. Epub 2007 Feb 10.


Investigation of the fungal strain Monodictys putredinis isolated from the inner tissue of a marine green alga led to the isolation of four new monomeric xanthones and a benzophenone. All structures were elucidated by extensive spectroscopic measurements. The relative configuration of compound 1 was determined by X-ray crystal structure analysis, while for 2 and 3 configurations were confirmed by NOE experiments. Absolute configurations for compounds 1-3 were deduced by comparing experimental circular dichroism spectroscopic data with those calculated employing quantum-chemical time-dependent density functional theory (TDDFT). The compounds were examined for their cancer chemopreventive potential. Xanthone 2 was shown to inhibit cytochrome P450 1A activity with an IC50 value of 3.0 microM. Compounds 2 and 3 displayed moderate activity as inducers of NAD(P)H:quinone reductase (QR) in cultured mouse Hepa 1c1c7 cells, with CD values (concentration required to double the specific activity of QR) of 12.0 and 12.8 microM, respectively. Compound 3 showed weak inhibition of aromatase activity.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anticarcinogenic Agents* / chemistry
  • Anticarcinogenic Agents* / isolation & purification
  • Anticarcinogenic Agents* / pharmacology
  • Aromatase Inhibitors* / chemistry
  • Aromatase Inhibitors* / isolation & purification
  • Aromatase Inhibitors* / pharmacology
  • Ascomycota / chemistry*
  • Crystallography, X-Ray
  • Inhibitory Concentration 50
  • Marine Biology
  • Molecular Conformation
  • Molecular Structure
  • NAD(P)H Dehydrogenase (Quinone) / biosynthesis
  • Xanthones* / chemistry
  • Xanthones* / isolation & purification
  • Xanthones* / pharmacology


  • Anticarcinogenic Agents
  • Aromatase Inhibitors
  • Xanthones
  • NAD(P)H Dehydrogenase (Quinone)