title: The hydroperoxide moiety of aliphatic lipid hydroperoxides is not affected by hypochlorous acid.
abstract: The oxidation of polyunsaturated fatty acids to the corresponding hydroperoxide by plant and animal lipoxygenases is an important step for the generation of bioactive lipid mediators. Thereby fatty acid hydroperoxide represent a common intermediate, also in human innate immune cells, like neutrophil granulocytes. In these cells a further key component is the heme protein myeloperoxidase producing HOCl as a reactive oxidant. On the basis of different investigation a reaction of the fatty acid hydroperoxide and hypochlorous acid (HOCl) could be assumed. Here, chromatographic and spectrometric analysis revealed that the hydroperoxide moiety of 15S-​hydroperoxy-​5Z,​8Z,​11Z,​13E-​eicosatetraenoic acid (15-HpETE) and 13S-​hydroperoxy-​9Z,​11E-​octadecadienoic acid (13-HpODE) is not affected by HOCl. No reduction of the hydroperoxide group due to a reaction with HOCl could be measured. It could be demonstrated that the double bonds of the fatty acid hydroperoxides are the major target of HOCl, present either as reagent or formed by the myeloperoxidase-hydrogen peroxide-chloride system.
authors.affiliation: Institute for Medical Physics and Biophysics, Medical Faculty, Leipzig University, Härtelstraße 16-18, 04107 Leipzig, Germany; Translational Centre for Regenerative Medicine (TRM), Leipzig University, Philipp-Rosenthal-Str. 55, 04103 Leipzig, Germany. Electronic address: josefin.zschaler@medizin.uni-leipzig.de.
authors.forename: Josefin
authors.initials: J
authors.lastname: Zschaler
authors.affiliation: Institute for Medical Physics and Biophysics, Medical Faculty, Leipzig University, Härtelstraße 16-18, 04107 Leipzig, Germany; Translational Centre for Regenerative Medicine (TRM), Leipzig University, Philipp-Rosenthal-Str. 55, 04103 Leipzig, Germany.
authors.forename: Juergen
authors.initials: J
authors.lastname: Arnhold
mesh_terms: D000818:Animals; D002851:Chromatography, High Pressure Liquid; D056148:Chromatography, Reverse-Phase; D005979:Glutathione Peroxidase / Q000378:metabolism; D006997:Hypochlorous Acid / Q000737:chemistry*; D015289:Leukotrienes / Q000032:analysis / Q000737:chemistry / Q000378:metabolism; D008041:Linoleic Acids / Q000032:analysis / Q000737:chemistry / Q000378:metabolism; D008054:Lipid Peroxides / Q000032:analysis* / Q000737:chemistry / Q000378:metabolism; D010084:Oxidation-Reduction; D009195:Peroxidase / Q000378:metabolism; D021241:Spectrometry, Mass, Electrospray Ionization
chemical_list: D015289:Leukotrienes; D008041:Linoleic Acids; D008054:Lipid Peroxides; C038649:13-hydroperoxy-9,11-octadecadienoic acid; C025086:15-hydroperoxy-5,8,11,13-eicosatetraenoic acid; D006997:Hypochlorous Acid; D009195:Peroxidase; D005979:Glutathione Peroxidase
keywords: Arachidonic acid; Hypochlorous acid; Lipid hydroperoxides; Lipoxygenase; Myeloperoxidase