Montagnuphilones A-G, Azaphilones from Montagnulaceae sp. DM0194, a Fungal Endophyte of Submerged Roots of Persicaria amphibia

J Nat Prod. 2017 Jan 27;80(1):76-81. doi: 10.1021/acs.jnatprod.6b00714. Epub 2017 Jan 18.

Abstract

Seven azaphilones, montagnuphilones A-G (1-7), together with previously known azaphilones 8-11, were encountered in Montagnulaceae sp. DM0194, an endophytic fungus isolated from submerged roots of Persicaria amphibia. The structures of 1-7 were elucidated on the basis of their MS and NMR spectroscopic analysis. Compounds 1-8 were evaluated for their cytotoxicity and ability to inhibit nitric oxide (NO) production in lipopolysaccharide-activated RAW264.7 macrophage cells. Among these, none were found to be cytotoxic to RAW264.7 cells up to 100.0 μM, but 8, 5, and 2 showed NO inhibitory activity with IC50 values of 9.2 ± 0.9, 25.5 ± 1.1, and 39.6 ± 1.8 μM, respectively.

Publication types

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

MeSH terms

  • Amphibians / microbiology*
  • Animals
  • Ascomycota / chemistry*
  • Benzopyrans / chemistry*
  • Benzopyrans / isolation & purification
  • Endophytes / chemistry*
  • Lipopolysaccharides / chemistry*
  • Lipopolysaccharides / isolation & purification
  • Lipopolysaccharides / pharmacology
  • Macrophages / chemistry
  • Macrophages / drug effects*
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Nitric Oxide / biosynthesis*
  • Nitric Oxide / chemistry
  • Pigments, Biological / chemistry*
  • Pigments, Biological / isolation & purification
  • Plant Roots / chemistry*

Substances

  • Benzopyrans
  • Lipopolysaccharides
  • Pigments, Biological
  • azaphilone
  • Nitric Oxide