title: Biomimetic nitration of conjugated linoleic acid: formation and characterization of naturally occurring conjugated nitrodienes.
abstract: Nitro-conjugated linoleic acids (NO2-cLA), endogenous nitrodiene lipids which act as inflammatory signaling mediators, were isolated and single isomers purified from the biomimetic acidic nitration products of conjugated linoleic acid (CLA). Structures were elucidated by means of detailed NMR and HPLC-MS/MS spectroscopic analysis and the relative double bond configurations assigned. Additional synthetic methods produced useful quantities and similar isomeric distributions of these unusual and reactive compounds for biological studies and isotopic standards, and the potential conversion of nitro-linoleic to nitro-conjugated linoleic acids was explored via a facile base-catalyzed isomerization. This represents one of the few descriptions of naturally occurring conjugated nitro dienes (in particular, 1-nitro 1,3-diene), an unusual and highly reactive motif with few biological examples extant.
authors.affiliation: Department of Pharmacology and Chemical Biology, University of Pittsburgh . Pittsburgh, Pennsylvania 15261, United States.
authors.forename: Steven R
authors.initials: SR
authors.lastname: Woodcock
authors.forename: Sonia R
authors.initials: SR
authors.lastname: Salvatore
authors.forename: Gustavo
authors.initials: G
authors.lastname: Bonacci
authors.forename: Francisco J
authors.initials: FJ
authors.lastname: Schopfer
authors.forename: Bruce A
authors.initials: BA
authors.lastname: Freeman
mesh_terms: D032701:Biomimetics; D002851:Chromatography, High Pressure Liquid; D044243:Linoleic Acids, Conjugated / Q000737:chemistry*; D008055:Lipids / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D009574:Nitro Compounds / Q000737:chemistry*; D053719:Tandem Mass Spectrometry
chemical_list: D044243:Linoleic Acids, Conjugated; D008055:Lipids; D009574:Nitro Compounds