Anacardic acid derived salicylates are inhibitors or activators of lipoxygenases

Bioorg Med Chem. 2012 Aug 15;20(16):5027-32. doi: 10.1016/j.bmc.2012.06.019. Epub 2012 Jun 21.

Abstract

Lipoxygenases catalyze the oxidation of unsaturated fatty acids, such as linoleic acid, which play a crucial role in inflammatory responses. Selective inhibitors may provide a new therapeutic approach for inflammatory diseases. In this study, we describe the identification of a novel soybean lipoxygenase-1 (SLO-1) inhibitor and a potato 5-lipoxygenase (5-LOX) activator from a screening of a focused compound collection around the natural product anacardic acid. The natural product anacardic acid inhibits SLO-1 with an IC(50) of 52 μM, whereas the inhibitory potency of the novel mixed type inhibitor 23 is fivefold enhanced. In addition, another derivative (21) caused non-essential activation of potato 5-LOX. This suggests the presence of an allosteric binding site that regulates the lipoxygenase activity.

MeSH terms

  • Anacardic Acids / chemistry*
  • Arachidonate 5-Lipoxygenase / metabolism*
  • Dose-Response Relationship, Drug
  • Enzyme Activation / drug effects
  • Glycine max / enzymology
  • Lipoxygenase / metabolism*
  • Lipoxygenase Inhibitors / chemical synthesis
  • Lipoxygenase Inhibitors / chemistry
  • Lipoxygenase Inhibitors / pharmacology*
  • Molecular Structure
  • Salicylates / chemical synthesis
  • Salicylates / chemistry
  • Salicylates / pharmacology*
  • Solanum tuberosum / enzymology
  • Structure-Activity Relationship

Substances

  • Anacardic Acids
  • Lipoxygenase Inhibitors
  • Salicylates
  • anacardic acid
  • Lipoxygenase
  • Arachidonate 5-Lipoxygenase