Synthesis and SAR studies of mono O-prenylated coumarins as potent 15-lipoxygenase inhibitors

► Synthesis of all mono isopentenyloxy, -geranyloxy and -farnesyloxy coumarins. ► Assay of the inhibitory potency (IC50) against soybean and human 15-lipoxygenase. ► Determination of the inhibitory mechanism. ► Docking analysis on both soybean and human 15-lipoxygenase. ► Discussion about IC50 differences between the human and plant enzyme.