Formation of trans-epoxy fatty acids correlates with formation of isoprostanes and could serve as biomarker of oxidative stress.
Biomarker
Eicosanoid
Isoprostane
Oxidative stress
Oxylipin
Trans-epoxy-fatty acid
Journal
Prostaglandins & other lipid mediators
ISSN: 1098-8823
Titre abrégé: Prostaglandins Other Lipid Mediat
Pays: United States
ID NLM: 9808648
Informations de publication
Date de publication:
10 2019
10 2019
Historique:
received:
15
11
2018
revised:
05
04
2019
accepted:
16
04
2019
pubmed:
23
4
2019
medline:
21
5
2020
entrez:
23
4
2019
Statut:
ppublish
Résumé
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/cis-epoxy-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.
Identifiants
pubmed: 31009766
pii: S1098-8823(18)30140-0
doi: 10.1016/j.prostaglandins.2019.04.004
pii:
doi:
Substances chimiques
Biomarkers
0
Isoprostanes
0
Trans Fatty Acids
0
Types de publication
Journal Article
Research Support, N.I.H., Extramural
Research Support, Non-U.S. Gov't
Review
Langues
eng
Sous-ensembles de citation
IM
Pagination
106334Subventions
Organisme : NIH HHS
ID : P40 OD010440
Pays : United States
Informations de copyright
Copyright © 2019 Elsevier Inc. All rights reserved.