Katharina M. Rund, Daniel Heylmann, Nina Seiwert, Sabine Wecklein, Camille Oger, Jean-Marie Galano, Thierry Durand, Rongjun Chen, Faikah Güler, Jörg Fahrer, Julia Bornhorst, Nils Helge Schebb
- In mammals, epoxy-polyunsaturated fatty acids (epoxy-PUFA) are enzymatically formed from naturally occurring all-cis PUFA by cytochrome P450 monooxygenases leading to the generation of cis-epoxy-PUFA (mixture of R,S- and S,R-enantiomers). In addition, also non-enzymatic chemical peroxidation gives rise to epoxy-PUFA leading to both, cis- and trans-epoxy-PUFA (mixture of R,R- and S,S-enantiomers). Here, we investigated for the first time trans-epoxy-PUFA and the trans/cis-epoxy-PUFA ratio as potential new biomarker of lipid peroxidation. Their formation was analyzed in correlation with the formation of isoprostanes (IsoP), which are commonly used as biomarkers of oxidative stress. Five oxidative stress models were investigated including incubations of three human cell lines as well as the in vivo model Caenorhabditis elegans with tert-butyl hydroperoxide (t-BOOH) and analysis of murine kidney tissue after renal ischemia reperfusion injury (IRI). A comprehensive set of IsoP and epoxy-PUFA derived from biologically relevant PUFA (ARA,In mammals, epoxy-polyunsaturated fatty acids (epoxy-PUFA) are enzymatically formed from naturally occurring all-cis PUFA by cytochrome P450 monooxygenases leading to the generation of cis-epoxy-PUFA (mixture of R,S- and S,R-enantiomers). In addition, also non-enzymatic chemical peroxidation gives rise to epoxy-PUFA leading to both, cis- and trans-epoxy-PUFA (mixture of R,R- and S,S-enantiomers). Here, we investigated for the first time trans-epoxy-PUFA and the trans/cis-epoxy-PUFA ratio as potential new biomarker of lipid peroxidation. Their formation was analyzed in correlation with the formation of isoprostanes (IsoP), which are commonly used as biomarkers of oxidative stress. Five oxidative stress models were investigated including incubations of three human cell lines as well as the in vivo model Caenorhabditis elegans with tert-butyl hydroperoxide (t-BOOH) and analysis of murine kidney tissue after renal ischemia reperfusion injury (IRI). A comprehensive set of IsoP and epoxy-PUFA derived from biologically relevant PUFA (ARA, EPA and DHA) was simultaneously quantified by LC-ESI(-)-MS/MS. Following renal IRI only a moderate increase in the kidney levels of IsoP and no relevant change in the trans/cis-epoxy-PUFA ratio was observed. In all investigated cell lines (HCT-116, HepG2 and Caki-2) as well as C. elegans a dose dependent increase of both, IsoP and the trans/cis-epoxy-PUFA ratio in response to the applied t-BOOH was observed. The different cell lines showed a distinct time dependent pattern consistent for both classes of autoxidatively formed oxylipins. Clear and highly significant correlations of the trans/cisepoxy-PUFA ratios with the IsoP levels were found in all investigated cell lines and C. elegans. Based on this, we suggest the trans/cis-epoxy-PUFA ratio as potential new biomarker of oxidative stress, which warrants further investigation.…
MetadatenAuthor details: | Katharina M. Rund, Daniel HeylmannORCiDGND, Nina SeiwertORCiD, Sabine Wecklein, Camille Oger, Jean-Marie GalanoORCiD, Thierry DurandORCiD, Rongjun ChenGND, Faikah GülerGND, Jörg FahrerORCiDGND, Julia BornhorstORCiDGND, Nils Helge SchebbORCiDGND |
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DOI: | https://doi.org/10.1016/j.prostaglandins.2019.04.004 |
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ISSN: | 1098-8823 |
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ISSN: | 2212-196X |
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Pubmed ID: | https://pubmed.ncbi.nlm.nih.gov/31009766 |
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Title of parent work (English): | Prostaglandins & Other Lipid Mediators |
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Publisher: | Elsevier |
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Place of publishing: | New York |
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Publication type: | Article |
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Language: | English |
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Year of first publication: | 2019 |
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Publication year: | 2019 |
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Release date: | 2020/11/23 |
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Tag: | Biomarker; Eicosanoid; Isoprostane; Oxidative stress; Oxylipin; Trans-epoxy-fatty acid |
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Volume: | 144 |
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Number of pages: | 10 |
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Funding institution: | Fonds der Chemischen IndustrieFonds der Chemischen Industrie; German Research Foundation (DFG)German Research Foundation (DFG) [SCHE 1801, BO 4103/2-1]; NIH Office of Research Infrastructure ProgramsUnited States Department of Health & Human ServicesNational Institutes of Health (NIH) - USA [P40 0D010440] |
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Organizational units: | Mathematisch-Naturwissenschaftliche Fakultät / Institut für Ernährungswissenschaft |
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DDC classification: | 5 Naturwissenschaften und Mathematik / 57 Biowissenschaften; Biologie / 570 Biowissenschaften; Biologie |
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Peer review: | Referiert |
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Publishing method: | Open Access |
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| Open Access / Green Open-Access |
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