Measurement and diagnostic use of hepatic cytochromeP450 metabolismof oleic acid in liver disease

Liver International

Volumn 30, Issue 8, 2010, Pages 1181-1188

  Thum, Thomas ^a   Batkai, Sandor ^a,b   Malinski, Philipp G ^a   Becker, Thomas ^a   Mevius, Iris ^a   Klempnauer, Jürgen ^a   Meyer, Hartmut H ^c   Frölich, Jürgen C ^a   Borlak, Jürgen ^d   Tsikas, Dimitrios ^a  

^a HANNOVER MEDICAL SCHOOL   (Germany)

^b NATIONAL INSTITUTE ON ALCOHOL ABUSE AND ALCOHOLISM   (United States)

^c LEIBNIZ UNIVERSITY HANNOVER   (Germany)

^d FRAUNHOFER INSTITUTE FOR TOXICOLOGY AND EXPERIMENTAL MEDICINE   (Germany)

Author keywords

Chronic liver disease; Cirrhosis; CYP2C8, 2C9, 1A2, 2C19, 3A4, 3A7; Cytochrome P450; Epoxidation; Gas chromatography; Hepatitis C; Oleic acid; Tandem mass spectrometry

Indexed keywords

CIS 9,10 EPOXYOCTADECANOIC ACID; CYTOCHROME P450; CYTOCHROME P450 1A; CYTOCHROME P450 1A2; CYTOCHROME P450 1B1; CYTOCHROME P450 2A6; CYTOCHROME P450 2B6; CYTOCHROME P450 2C19; CYTOCHROME P450 2C8; CYTOCHROME P450 2C9; CYTOCHROME P450 2D6; CYTOCHROME P450 2E1; CYTOCHROME P450 3A4; CYTOCHROME P450 3A5; CYTOCHROME P450 3A7; CYTOCHROME P450 4A11; OLEIC ACID; STEARIC ACID DERIVATIVE; UNCLASSIFIED DRUG; UNSPECIFIC MONOOXYGENASE;

ADULT; AGED; ALCOHOL LIVER CIRRHOSIS; ARTICLE; BLOOD LEVEL; CLINICAL ARTICLE; COMPARATIVE STUDY; CONTROLLED STUDY; DIAGNOSTIC VALUE; ENZYME ACTIVITY; FEMALE; HEPATITIS C; HUMAN; IN VITRO STUDY; LIVER CIRRHOSIS; LIVER DISEASE; MALE; PLASMA;

ADULT; AGED; BIOLOGICAL MARKERS; CYTOCHROME P-450 ENZYME SYSTEM; FEMALE; GAS CHROMATOGRAPHY-MASS SPECTROMETRY; HUMANS; LIVER DISEASES; MALE; MIDDLE AGED; MOLECULAR STRUCTURE; OLEIC ACID; STEARIC ACIDS;

EID: 79951643524     PISSN: 14783223     EISSN: 14783231     Source Type: Journal    
DOI: 10.1111/j.1478-3231.2010.02310.x     Document Type: Article

References (22)

1. Massaro M, De Caterina R. Vasculoprotective effects of oleic aicd: epidemiological background and direct vascular antiatherogenic properties. Nutr Metab Cardiovasc Dis 2002; 12: 42-51.
2. Yaqoob P. Monounsaturated fatty acids and immune function. Eur J Clin Nutr 2002; 56: S9-13.
3. Ulsaker GA, Teien G. Gas chromatographic-mass spectrometric identification of 9,10-epoxystearate in human blood. Analyst 1983; 108: 521-4.
4. Tsikas D, Sawa M, Brunner G, et al. Gas chromatographymass 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. J Chromatogr B 2003; 784: 351-65.
5. Laethem RM, Balazy M, Koop DR. Epoxidation of C18 unsaturated fatty acids by cytochromes P4502C2 and P4502CAA. Drug Metab Dispos 1996; 24: 664-8.
6. Fahlstadius P. cis-9,10-epoxystearic acid in human leukocytes: isolation and quantitative determination. Lipids 1988; 23: 1015-8.
7. Thum T, Borlak J. Mechanistic role of CYP monooxygenases in oxLDL induced vascular injury. Therapy through LOX-1 receptor antagonism? Circ Res 2004; 94: 1-13.
8. Tsikas D, Mitschke A, Gutzki FM, Meyer HH, Fr̈olich JC. Gas chromatography-mass spectrometry of cis-9,10-epoxyoctadecanoic acid (cis-EODA). II. Quantitative determination of cis-EODA in human plasma by GC-tandem MS. J Chromatogr B 2004; 804: 403-12.
9. 2alpha. Possible methodological, mechanistic and clinical implications. J Chromatogr B 2003; 794: 237-55.
10. Ding X, Kaminsky LS. Human extrahepatic cytochromes P450: function in xenobiotic metabolism and tissueselective chemical toxicity in the respiratory and gastrointestinal tracts. Annu Rev Pharmacol Toxicol 2003; 43: 149-73.
11. Thum T, Borlak J. Gene expression in distinct regions of the heart. Lancet 2000; 355: 979-83.
12. George J, Murray M, Byth K, Farell GC. Differential alterations of cytochrome P450 proteins in livers from patients with severe chronic liver disease. Hepatology 1995; 21: 120-8.
13. Bastine MC, Leblond F, Pichette V, Villeneuve JP. Differential alteration of cytochrome P450 isoenzymes in two experimental models of cirrhosis. Can J Physiol Pharmacol 2000; 78: 912-9.
14. Chalasani N, Gorski JC, Patel NH, Hall SD, Galinsky RE. Hepatic and intestinal cytochrome P450 3A activity in cirrhosis: effects of transjugular intrahepatic portosystemic shunts. Hepatology 2001; 34: 1103-8.
15. Morrow JD, Moore KP, Awad JA, et al. Marked overproduction of non-cyclooxygenase derived prostanoids (F2-isoprostanes) in the hepatorenal syndrome. J Lipid Mediat 1993; 6: 417-20.
16. 2alpha in end-stage liver disease. Hepatology 2003; 38: 1063-4.
17. Watabe T, Ueno Y, Imazumi J. Conversion of oleic acid into threo-dihydroxystearic acid by rat liver microsomes. Biochem Pharmacol 1971; 20: 912-3.
18. Sharma R, Gupta S, Singhal SS, Ansari GA, Awasthi YC. Glutathione S-transferase-catalysed conjugation of 9,10-epoxystearic acid with glutathione. J Biochem Toxicol 1991; 6: 147-53.
19. Tsikas D, Brunner G. Analysis of glutathione conjugates by HPLC II. Ion-exchange chromatography and fluorescence detection. Fresenius J Anal Chem 1992; 343: 330-4.
20. Chu I, Villeneuve DC, Secours V, Viau A. Absorption, distribution and metabolism of epoxystearic acid in the rat. Bull Environm Contam Toxicol 1979; 22: 462-6.
21. Borlak J, Thum T. Identification of major CYP2C9 and CYP2C19 polymorphisms by fluorescence resonance energy transfer analysis. Clin Chem 2002; 48: 1592-4.
22. Borlak J, Hermann R, Erb K, Thum T. A rapid and simple CYP2D6 genotyping assay - case study with the analgetic tramadol. Metabolism 2003; 52: 1439-43.