title: Synthesis and discovery of phytofurans: metabolites of α-linolenic acid peroxidation.
abstract: Phytofurans are novel metabolites produced by non-enzymatic peroxidation of α-linolenic acid. An unprecedented Payne rearrangement-cyclization of a C2-symmetric bis-epoxide permitted construction of the core 3-hydroxy-2,5-disubstituted tetrahydrofuran. LC-MS/MS investigation provided evidence for the presence of phytofurans in nuts and seeds for the first time.
authors.affiliation: Institut des Biomolécules Max Mousseron (IBMM), UMR CNRS 5247 - Université de Montpellier - ENSCM Faculté de Pharmacie, 15 avenue Charles Flahault, 34093 Montpellier cedex 05, France. camille.oger@umontpellier.fr jean-marie.galano@umontpellier.fr.
authors.forename: C
authors.initials: C
authors.lastname: Cuyamendous
authors.forename: K S
authors.initials: KS
authors.lastname: Leung
authors.forename: T
authors.initials: T
authors.lastname: Durand
authors.forename: J C-Y
authors.initials: JC
authors.lastname: Lee
authors.forename: C
authors.initials: C
authors.lastname: Oger
authors.forename: J-M
authors.initials: JM
authors.lastname: Galano
mesh_terms: D002853:Chromatography, Liquid; D019597:Flax; D005663:Furans / Q000737:chemistry*; D031324:Juglans; D009754:Nuts / Q000737:chemistry*; D010084:Oxidation-Reduction; D028223:Pinus; D027544:Salvia; D012639:Seeds / Q000737:chemistry*; D053719:Tandem Mass Spectrometry; D017962:alpha-Linolenic Acid / Q000737:chemistry*
chemical_list: D005663:Furans; D017962:alpha-Linolenic Acid