Application of the Crystalline Sponge Method to Revise the Structure of the Phenalenone Fuliginone

Molecules. 2017 Jan 30;22(2):211. doi: 10.3390/molecules22020211.

Abstract

The structure of fuliginone was revised from a phenyl substituted phenalenone to a hydroxyl substituted phenalenone as a result of its re-purification via HPLC with subsequent NMR analysis together with an independent synthesis and analysis of the crystal structure, which was secured via the crystalline sponge method. On-flow High Performance Liquid Chromatography coupled to Nuclear Magnetic Resonance spectroscopy (HPLC-NMR) was employed to confirm the presence of the natural product in the plant extract and to monitor for any possible degradation or conversion of the compound.

Keywords: fuliginone; HPLC‐NMR; crystalline sponge method; phenylphenalenone; synthesis.

MeSH terms

  • Biological Products / chemistry
  • Biological Products / isolation & purification
  • Chromatography, High Pressure Liquid
  • Gas Chromatography-Mass Spectrometry
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Phenalenes / chemistry*
  • Phenalenes / isolation & purification*
  • Plant Extracts / chemistry
  • Plant Extracts / isolation & purification

Substances

  • Biological Products
  • Phenalenes
  • Plant Extracts
  • phenalen-1-one