Synthesis of all-trans arachidonic acid and its effect on rabbit platelet aggregation

A simple and high-yielding method to convert natural all-cis PUFA derivatives to the corresponding all-trans geometrical isomers is described. The method is based on the thiyl radical-catalyzed cis–trans isomerization. The all-trans isomer of arachidonic acid was found to cause rabbit platelet aggregation at concentrations higher than 0.1 mM and inhibition of PAF-induced platelet aggregation in a concentration dependent manner with an IC50 in the micromolar range.

The first synthesis of all-trans isomer of arachidonic acid is reported together with its effects on rabbit platelet aggregation. The all-trans PUFA strategy allows a chemical biology approach for the investigation of the effect of the lipid trans geometry in the biological environment.Figure optionsDownload as PowerPoint slide