Novel lipoxygenase inhibitor, 1-ethenoxy-2-methylbenzene, from marine cyanobacteria Microcoleus chthonoplastes

Nat Prod Res. 2018 Dec;32(24):2910-2915. doi: 10.1080/14786419.2017.1392949. Epub 2017 Oct 25.

Abstract

Lipoxygenase (LOX) inhibitors are considered to be important anti-inflammatory agents as it can control many inflammatory responses to some extent. Even though the marine bio-systems are not well explored, they are considered to be one of the promising repositories for drug lead molecules against variety of diseases. In the present study a new LOX inhibitor compound, 1-ethenoxy-2-methylbenzene, reported first time from a living system, Microcoleus chthonoplastes, has been isolated by activity guided fractionation and further structurally characterised by techniques such as FTIR, NMR and LC MS/MS. Further enzyme kinetics, isothermal titration calorimetry and molecular docking methods were used in order to get a better understanding of enzyme-ligand interactions. This exploration suggests its worthiness as a lead molecule for the development of a better anti-inflammatory drug. Its high structure-activity resemblance to cuminaldehyde from cumin seeds, which is earlier reported as a LOX inhibitor, is also established.

Keywords: Cyanobacteria; isothermal titration calorimetry; lipoxygenase inhibitor; molecular docking; structure elucidation.

MeSH terms

  • Anti-Inflammatory Agents / isolation & purification*
  • Anti-Inflammatory Agents / pharmacology
  • Aquatic Organisms / chemistry
  • Benzaldehydes / chemistry
  • Benzene Derivatives / chemistry
  • Benzene Derivatives / isolation & purification
  • Benzene Derivatives / pharmacology
  • Calorimetry
  • Chromatography, Liquid
  • Cuminum / drug effects
  • Cyanobacteria / chemistry*
  • Cymenes
  • Kinetics
  • Lipoxygenase Inhibitors / isolation & purification*
  • Lipoxygenase Inhibitors / pharmacology
  • Molecular Docking Simulation
  • Spectrum Analysis / methods

Substances

  • Anti-Inflammatory Agents
  • Benzaldehydes
  • Benzene Derivatives
  • Cymenes
  • Lipoxygenase Inhibitors
  • cuminaldehyde