Rhytidenones A-F, Spirobisnaphthalenes from Rhytidhysteron sp. AS21B, an Endophytic Fungus

J Nat Prod. 2014 Aug 22;77(8):1962-6. doi: 10.1021/np500068y.

Abstract

Rhytidenone A (1), a unique spirobisnaphthalene with a 1,7-dioxaspiro[4,4]nonan-2-one motif, and five new spirobisnaphthalenes, rhytidenones B-F (2-6), were isolated from the extract of a cultured fungal endophyte, Rhytidhysteron sp. AS21B. Their structures were elucidated mainly by analysis of NMR spectroscopic data. The structure and configuration of 1 were further confirmed by single-crystal X-ray diffraction analysis. Compounds 3 and 4 exhibited significant inhibitory activity against nitric oxide production from activated macrophages with IC50 values of 0.31 and 3.60 μM, respectively.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Ascomycota / chemistry*
  • Crystallography, X-Ray
  • Female
  • Indomethacin / pharmacology
  • Macrophages / drug effects
  • Mice
  • Molecular Conformation
  • Molecular Structure
  • Naphthalenes / chemistry
  • Naphthalenes / isolation & purification*
  • Naphthalenes / pharmacology
  • Nuclear Magnetic Resonance, Biomolecular
  • Plant Leaves / microbiology
  • Salvadoraceae / microbiology
  • Spiro Compounds / chemistry
  • Spiro Compounds / isolation & purification*
  • Spiro Compounds / pharmacology
  • Thailand

Substances

  • Naphthalenes
  • Spiro Compounds
  • rhytidenone A
  • Indomethacin