title: Total syntheses and in vivo quantitation of novel neurofuran and dihomo-isofuran derived from docosahexaenoic acid and adrenic acid.
abstract: Neurofurans (NeuroFs) and dihomo-isofurans (dihomo-IsoFs) are produced in vivo by non-enzymatic free-radical pathways from docosahexaenoic and adrenic acids, respectively. As these metabolites are produced in minute amounts, their analyses in biological samples remain challenging. Syntheses of neurofuran and dihomo-isofurans described are based on a pivotal strategy, thanks to an enantiomerically enriched intermediate, which allowed, for the first time, access to both families: the alkenyl and enediol. Owing to this formation, quantitation of specific NeuroF and dihomo-IsoFs in biological samples was attainable.
authors.affiliation: Institut des Biomolécules Max Mousseron (IBMM), UMR CNRS 5247, Universités de Montpellier I et II, ENSCM, Faculté de Pharmacie,15 Av. Charles Flahault, BP 14491, 34093 Montpellier cedex 05 (France), Fax: (+33) 411759553.
authors.forename: Aurélien
authors.initials: A
authors.lastname: de la Torre
authors.forename: Yiu Yiu
authors.initials: YY
authors.lastname: Lee
authors.forename: Attilio
authors.initials: A
authors.lastname: Mazzoni
authors.forename: Alexandre
authors.initials: A
authors.lastname: Guy
authors.forename: Valérie
authors.initials: V
authors.lastname: Bultel-Poncé
authors.forename: Thierry
authors.initials: T
authors.lastname: Durand
authors.forename: Camille
authors.initials: C
authors.lastname: Oger
authors.forename: Jetty Chung-Yung
authors.initials: JC
authors.lastname: Lee
authors.forename: Jean-Marie
authors.initials: JM
authors.lastname: Galano
mesh_terms: D000818:Animals; D001921:Brain / Q000378:metabolism; D004281:Docosahexaenoic Acids / Q000737:chemistry*; D005227:Fatty Acids / Q000032:analysis; D005231:Fatty Acids, Unsaturated / Q000737:chemistry*; D005663:Furans / Q000032:analysis / Q000138:chemical synthesis / Q000737:chemistry*; D028421:Isoprostanes / Q000032:analysis; D009206:Myocardium / Q000378:metabolism; D051381:Rats; D013237:Stereoisomerism
chemical_list: D005227:Fatty Acids; D005231:Fatty Acids, Unsaturated; D005663:Furans; D028421:Isoprostanes; C011395:adrenic acid; D004281:Docosahexaenoic Acids
keywords: dihomo-isofurans; fatty acids; neurofurans; oxygenated metabolites; total synthesis