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

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.