Total Synthesis and in Vivo Quantitation of Phytofurans Derived from α-Linolenic Acid

Abstract

Phytoprostanes (PhytoPs) are produced in plants and seeds by non-enzymatic free-radical pathways from α-linolenic acid (ALA). We recently highlighted the formation of a new class of compounds from ALA, namely phytofurans (PhytoFs). In biological samples, these compounds are produced as mixtures, and their analytical exploration remains challenging without their pure synthetic forms. The synthesis of some phytofurans is described here. The use of an enantiomerically enriched intermediate allowed for the first time access to both families of PhytoFs, the alkenyl and enediol classes. For the first time, PhytoF metabolites have been quantitated in the liver tissue of rats treated with an ALA-rich flaxseed or flaxseed oil diet.