Total Synthesis and in Vivo Quantitation of Phytofurans Derived from α‐Linolenic Acid. Issue 17 (3rd May 2017)

• Record Type: Journal Article
• Authors: Cuyamendous, Claire; Leung, Kin Sum; Bultel‐Poncé, Valérie; Guy, Alexandre; Durand, Thierry; Galano, Jean‐Marie; Lee, Jetty Chung‐Yung; Oger, Camille
• Is Part Of: European journal of organic chemistry. Issue 17(2017)
• Page Start: 2486
• Page End: 2490
• Publication Date: 2017-05-03
• Subjects: Total synthesis -- Oxidative stress -- Fatty acids -- Phytofurans -- Biomarkers; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201700270
• Languages: English
• ISSNs: 1434-193X

Abstract

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. Abstract : Phytofurans (PhytoFs) are produced in plants and seeds by a non‐enzymatic free‐radical mechanism from α‐linolenic acid. The synthesis of some phytofurans is described. The phytofurans were also quantitated for the first time in the liver tissue of rats.