Premium
Total Synthesis and in Vivo Quantitation of Phytofurans Derived from α‐Linolenic Acid
Author(s) -
Cuyamendous Claire,
Leung Kin Sum,
BultelPoncé Valérie,
Guy Alexandre,
Durand Thierry,
Galano JeanMarie,
Lee Jetty ChungYung,
Oger Camille
Publication year - 2017
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201700270
Subject(s) - chemistry , in vivo , linolenic acid , total synthesis , enzyme , biochemistry , organic chemistry , stereochemistry , fatty acid , linoleic acid , microbiology and biotechnology , biology
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.