Structural library and visualization of endogenously oxidized phosphatidylcholines using mass spectrometry-based techniques

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  • Matsuoka, Yuta
    Physical Chemistry for Life Science Laboratory, Faculty of Pharmaceutical Sciences, Kyushu University
  • Takahashi, Masatomo
    Metabolomics Laboratory, Research Center for Transomics Medicine, Medical Institute of Bioregulation, Kyushu University
  • Sugiura, Yuki
    Department of Biochemistry, Keio University School of Medicine
  • Izumi, Yoshihiro
    Metabolomics Laboratory, Research Center for Transomics Medicine, Medical Institute of Bioregulation, Kyushu University
  • Nishiyama, Kazuhiro
    Department of Physiology, Faculty of Pharmaceutical Sciences, Kyushu University
  • Nishida, Motohiro
    Department of Physiology, Faculty of Pharmaceutical Sciences, Kyushu University Division of Cardiocirculatory Signaling, National Institute for Physiological Sciences and Exploratory Research Center on Life and Living Systems, National Institutes of Natural Sciences
  • Suematsu, Makoto
    Department of Biochemistry, Keio University School of Medicine
  • Bamba, Takeshi
    Metabolomics Laboratory, Research Center for Transomics Medicine, Medical Institute of Bioregulation, Kyushu University
  • Yamada, Ken-ichi
    Physical Chemistry for Life Science Laboratory, Faculty of Pharmaceutical Sciences, Kyushu University

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Abstract

Although oxidized phosphatidylcholines (oxPCs) play critical roles in numerous pathological events, the type and production sites of endogenous oxPCs remain unknown because of the lack of structural information and dedicated analytical methods. Herein, a library of 465 oxPCs is constructed using high-resolution mass spectrometry-based non-targeted analytical methods and employed to detect 70 oxPCs in mice with acetaminophen-induced acute liver failure. We show that doubly oxygenated polyunsaturated fatty acid (PUFA)-PCs (PC PUFA;O2), containing epoxy and hydroxide groups, are generated in the early phase of liver injury. Hybridization with in-vivo^<18>O labeling and matrix-assisted laser desorption/ionization-tandem MS imaging reveals that PC PUFA;O2 are accumulated in cytochrome P450 2E1-expressing and glutathione-depleted hepatocytes, which are the major sites of liver injury. The developed library and visualization methodology should facilitate the characterization of specific lipid peroxidation events and enhance our understanding of their physiological and pathological significance in lipid peroxidation-related diseases.

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