Gas chromatography–mass spectrometry of cis-9,10-epoxyoctadecanoic acid (cis-EODA)I. Direct evidence for cis-EODA formation from oleic acid oxidation by liver microsomes and isolated hepatocytes

Tsikas, Dimitrios; Sawa, Masayuki; Brunner, G.; Gutzki, Frank‐Mathias; Meyer, H.; Frölich, Jürgen C.

doi:10.1016/s1570-0232(02)00821-8

Cited by 18 publications

(17 citation statements)

References 37 publications

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“…Therefore, the product ions at m/z 171 and 155 are characteristic for 9,10-epoxyoctadecanoic acid. Discrimination between the PFB esters of cis-and trans-EODA is possible both by GC and HPLC [19]. In the present study the relative GC retention time of cis-to trans-EODA was 1.04 when analyzed as PFB ester (see also below).…”

Section: Gc-ms and Gc-tandem Ms Mass Spectra Of Cis-eoda And Cis-d 2 supporting

confidence: 46%

“…PFB esters of fatty acids were prepared by a standard derivatization procedure [19]. Briefly, solvents are removed by a stream of nitrogen gas and residues are reconstituted in water-free acetonitrile (100 l).…”

Section: Derivatization Proceduresmentioning

confidence: 99%

“…However, cis-EODA is stable enough in order to be isolated from biological fluids prior to GC-MS analysis [10][11][12]. Furthermore, in previous work we showed that the oxirane ring of cis-EODA is thermally sufficiently stable for GC-MS analysis of intact cis-EODA as its methyl or pentafluorobenzyl (PFB) ester [19]. The possibility of analyzing intact cis-EODA as its PFB ester by GC-MS in the negative-ion chemical ionization (NICI) mode fulfills an important requirement for sensitive quantitative determination of cis-EODA in biological fluids, such as plasma, serum and urine of humans, in which basal levels of cis-EODA are expected to be in the lower nM-range [10][11][12].…”

Section: Introductionmentioning

confidence: 99%

“…The detection of racemic cis-EODA in lipids of human leukocytes [17] suggests a free radical-catalyzed epoxidation of esterified oleic acid in lipids. On the other hand, the cytochrome P450 (CYP) system has been shown to be responsible for the enzymic epoxidation of oleic acid to cis-EODA [18,19]. The CYP isoforms 2C2 and 2CAA have been shown to epoxidize oleic acid to cis-EODA [20].…”

Section: Introductionmentioning

confidence: 99%

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Gas chromatography–mass spectrometry of cis-9,10-epoxyoctadecanoic acid (cis-EODA)

Tsikas

Mitschke

Gutzki

et al. 2004

Journal of Chromatography B

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Section: Gc-ms and Gc-tandem Ms Mass Spectra Of Cis-eoda And Cis-d 2 supporting

confidence: 46%

Section: Derivatization Proceduresmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Gas chromatography–mass spectrometry of cis-9,10-epoxyoctadecanoic acid (cis-EODA)

Tsikas

Mitschke

Gutzki

et al. 2004

Journal of Chromatography B

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“…cis-EpOA can be formed by CYP-catalyzed epoxidation of oleic acid and the OLT patients of the present study had lower plasma cis-EpOA concentration than healthy subjects (8). As CYP-catalyzed synthesis of cis--EpOA requires the cofactor NADPH (8,20), deficiency in NADPH after liver reperfusion may be an explanation for the continuous decay of plasma cis-EpOA concentration during OLT, which is analogous to the decrease in plasma Creatinine-corrected excretion of free non-conjugated 15(S)-8-iso-PGF 2α by nine patients who underwent OLT. Urine samples U1 were collected prior to anesthesia by spontaneous micturition.…”

Section: Discussionmentioning

confidence: 63%

Does Oxidative Stress Change During Orthotopic Liver Transplantation?

Tsikas

2017

jcbmr

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In clinical ischemia/reperfusion injury, damage resulting from oxidative and nitrosative stress is generally considered crucial for graft functioning. Yet, there is reasonable doubt that modern clinical transplantation including orthotopic liver transplantation (OLT) is associated with elevation of oxidative and nitrosative stress upon organ reoxygenation. We measured two biomarkers of oxidative stress, 15(S)-8-iso-prostaglandin F 2α (15(S)-8-iso-PGF 2α ) and cis-epoxyoctadecanoic acid (cis-EpOA), in human plasma during the entire time duration of OLT in nine patients suffering from end-stage liver disease. No considerable concentration changes of 15(S)-8-iso-PGF 2α and cis-EpOA were observed in plasma, indicating lack of oxidative stress. Creatinine-corrected urinary excretion of 15(S)-8-iso-PGF 2α in two urine samples collected 40-60 min and 60-240 min after reperfusion did not increase significantly. Previously, we found in the same patients that nitrosative stress, measured as 3-nitrotyrosine and 3-nitrotyrosinoalbumin, is elevated in the patients but did not change during OLT. 15(S)-8-iso-PGF 2α , cis-EpOA, 3-nitrotyrosine and other widely used biomarkers of oxidative stress, notably malondialdehyde (MDA), are produced both by chemical and enzymatic reactions. This important issue is rarely considered in the area of oxidative and nitrosative stress. In addition, many widely used analytical approaches such as the total antioxidant capacity (TAC) assay to quantitate oxidative and nitrosative stress in health and disease and during clinical transplantation lack reliability. New basic concepts of oxidative and nitrosative stress need to be drafted and implemented in vitro as well as in vivo in experimental and clinical settings.

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Current literature in mass spectrometry

2003

J. Mass Spectrom.

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In order to keep subscribers up‐to‐date with the latest developments in their field, John Wiley & Sons are providing a current awareness service in each issue of the journal. The bibliography contains newly published material in the field of mass spectrometry. Each bibliography is divided into 11 sections: 1 Books, Reviews & Symposia; 2 Instrumental Techniques & Methods; 3 Gas Phase Ion Chemistry; 4 Biology/Biochemistry: Amino Acids, Peptides & Proteins; Carbohydrates; Lipids; Nucleic Acids; 5 Pharmacology/Toxicology; 6 Natural Products; 7 Analysis of Organic Compounds; 8 Analysis of Inorganics/Organometallics; 9 Surface Analysis; 10 Environmental Analysis; 11 Elemental Analysis. Within each section, articles are listed in alphabetical order with respect to author (5 Weeks journals ‐ Search completed at 19th. February. 2003)

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Gas chromatography–mass spectrometry of cis-9,10-epoxyoctadecanoic acid (cis-EODA)I. Direct evidence for cis-EODA formation from oleic acid oxidation by liver microsomes and isolated hepatocytes

Cited by 18 publications

References 37 publications

Gas chromatography–mass spectrometry of cis-9,10-epoxyoctadecanoic acid (cis-EODA)

Gas chromatography–mass spectrometry of cis-9,10-epoxyoctadecanoic acid (cis-EODA)

Does Oxidative Stress Change During Orthotopic Liver Transplantation?

Current literature in mass spectrometry

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