Pleurospiroketals A-E, perhydrobenzannulated 5,5-spiroketal sesquiterpenes from the edible mushroom Pleurotus cornucopiae

J Nat Prod. 2013 Jan 25;76(1):45-50. doi: 10.1021/np3006524. Epub 2013 Jan 8.

Abstract

Five novel perhydrobenzannulated 5,5-spiroketal sesquiterpenes, namely, pleurospiroketals A-E (1-5), were isolated from the culture of the edible mushroom Pleurotus cornucopiae. Pleurospiroketals D (4) and E (5) were obtained as an isomeric mixture with a ratio of 5:4. Their structures were established by NMR, X-ray single-crystal diffraction, and CD data analysis. Pleurospiroketals A-E (1-5) are sesquiterpenoids with a unique benzannulated 5,5-spiroketal skeleton. Compounds 1-3 showed inhibitory activity against nitric oxide production in lipopolysaccharide-activated macrophages with IC(50) values of 6.8, 12.6, and 20.8 μM, respectively.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Crystallography, X-Ray
  • Furans / chemistry
  • Furans / isolation & purification*
  • Furans / pharmacology
  • HeLa Cells
  • Humans
  • Inhibitory Concentration 50
  • Lipopolysaccharides / pharmacology
  • Macrophages / drug effects
  • Mice
  • Molecular Conformation
  • Molecular Structure
  • Nitric Oxide / biosynthesis
  • Nuclear Magnetic Resonance, Biomolecular
  • Pleurotus / chemistry*
  • Sesquiterpenes / chemistry
  • Sesquiterpenes / isolation & purification*
  • Sesquiterpenes / pharmacology
  • Spiro Compounds / chemistry
  • Spiro Compounds / isolation & purification*
  • Spiro Compounds / pharmacology
  • Stereoisomerism

Substances

  • Furans
  • Lipopolysaccharides
  • Sesquiterpenes
  • Spiro Compounds
  • pleurospiroketal A
  • spiroketal
  • Nitric Oxide