title: Dihydroxylated E,E,Z-docosatrienes. An overview of their synthesis and biological significance.
abstract: Dihydroxylated E,E,Z-docosatrienes are acyclic lipoxygenase metabolites of 22-carbon atom polyunsaturated fatty acids (PUFAs) containing a conjugated E,E,Z-triene flanked by two secondary allylic alcohols. The two main metabolites, protectin D1 (PD1) and its regioisomer maresin 1 (MaR1), were shown to be actively involved in the resolution and more specifically the termination of the inflammation process. Studies directed at the synthesis of E,E,Z-docosatrienes have been undertaken to resolve stereochemical ambiguities, and provide standards for biological evaluation and reference samples for in-vivo detection and lipidomic analyses. In this review we provide a brief update of the literature on the biological significance of E,E,Z-docosatrienes and the role that synthetic organic chemists has played in the development of these lipids, providing an overview and comparison of the different strategies employed to access synthetic E,E,Z-docosatriene standards.
authors.affiliation: Institut des Biomolécules Max Mousseron (IBMM, UMR5247 CNRS-UM-ENSCM), Faculté de Pharmacie, 15 av. C. Flahault, B.P. 14491, 34093 Montpellier Cedex 5, France. Electronic address: laurence.balas@umontpellier.fr.
authors.forename: Laurence
authors.initials: L
authors.lastname: Balas
authors.affiliation: Institut des Biomolécules Max Mousseron (IBMM, UMR5247 CNRS-UM-ENSCM), Faculté de Pharmacie, 15 av. C. Flahault, B.P. 14491, 34093 Montpellier Cedex 5, France.
authors.forename: Thierry
authors.initials: T
authors.lastname: Durand
mesh_terms: D000818:Animals; D053898:Biosynthetic Pathways; D060326:Chemistry Techniques, Synthetic; D004281:Docosahexaenoic Acids / Q000138:chemical synthesis / Q000494:pharmacology / Q000502:physiology*; D006801:Humans; D006900:Hydroxylation; D050356:Lipid Metabolism; D009416:Nerve Regeneration; D018696:Neuroprotective Agents / Q000138:chemical synthesis / Q000494:pharmacology
chemical_list: D018696:Neuroprotective Agents; D004281:Docosahexaenoic Acids
keywords: Docosatriene; Inflammation; Maresin; PUFA metabolite; Protectin; Virology