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Volumn 329, Issue 4, 2005, Pages 1275-1281

Eicosapentaenoic acid metabolism by cytochrome P450 enzymes of the CYP2C subfamily

Author keywords

CYP2C11; CYP2C23; CYP2C8; CYP2C9; Cytochrome P450; Eicosanoid; Eicosapentaenoic acid; Epoxidation; n 3 polyunsaturated fatty acid

Indexed keywords

17,18 EPOXYEICOSATETRAENOIC ACID; ARACHIDONIC ACID; CYTOCHROME P450 2C; CYTOCHROME P450 2C11; CYTOCHROME P450 2C23; CYTOCHROME P450 2C8; CYTOCHROME P450 2C9; EPOXYGENASE; EPOXYICOSATRIENOIC ACID; ICOSAPENTAENOIC ACID; OMEGA 3 FATTY ACID; RECOMBINANT ENZYME; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE PHOSPHATE FERRIHEMOPROTEIN REDUCTASE; UNCLASSIFIED DRUG;

EID: 17644391400     PISSN: 0006291X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bbrc.2005.02.103     Document Type: Article
Times cited : (82)

References (36)
  • 1
    • 0032819001 scopus 로고    scopus 로고
    • Essential fatty acids in health and chronic disease
    • A.P. Simopoulos Essential fatty acids in health and chronic disease Am. J. Clin. Nutr. 70 1999 560S 569S
    • (1999) Am. J. Clin. Nutr. , vol.70
    • Simopoulos, A.P.1
  • 2
    • 0033972318 scopus 로고    scopus 로고
    • Importance of n-3 fatty acids in health and disease
    • W.E. Conner Importance of n-3 fatty acids in health and disease Am. J. Clin. Nutr. 70 2000 171S 175S
    • (2000) Am. J. Clin. Nutr. , vol.70
    • Conner, W.E.1
  • 3
    • 0037137299 scopus 로고    scopus 로고
    • Fish consumption, fish oil, omega-3 fatty acids, and cardiovascular disease
    • P.M. Kris-Etherton, W.S. Harris, and L.J. Appel Fish consumption, fish oil, omega-3 fatty acids, and cardiovascular disease Circulation 106 2002 2747 2757
    • (2002) Circulation , vol.106 , pp. 2747-2757
    • Kris-Etherton, P.M.1    Harris, W.S.2    Appel, L.J.3
  • 4
    • 0037088677 scopus 로고    scopus 로고
    • The biochemistry of n-3 polyunsaturated fatty acids
    • D.B. Jump The biochemistry of n-3 polyunsaturated fatty acids J. Biol. Chem. 277 2002 8755 8758
    • (2002) J. Biol. Chem. , vol.277 , pp. 8755-8758
    • Jump, D.B.1
  • 5
    • 3042767902 scopus 로고    scopus 로고
    • Dietary long-chain n-3 fatty acids for the prevention of cancer: A review of potential mechanisms
    • S.C. Larsson, M. Kumlin, M. Ingelman-Sundberg, and A. Wolk Dietary long-chain n-3 fatty acids for the prevention of cancer: a review of potential mechanisms Am. J. Clin. Nutr. 79 2004 935 945
    • (2004) Am. J. Clin. Nutr. , vol.79 , pp. 935-945
    • Larsson, S.C.1    Kumlin, M.2    Ingelman-Sundberg, M.3    Wolk, A.4
  • 6
    • 0033993749 scopus 로고    scopus 로고
    • Cytochrome P450 and arachidonic acid bioactivation: Molecular and functional properties of the arachidonate monooxygenase
    • J.H. Capdevila, J.R. Falck, and R.C. Harris Cytochrome P450 and arachidonic acid bioactivation: molecular and functional properties of the arachidonate monooxygenase J. Lipid Res. 41 2000 163 181
    • (2000) J. Lipid Res. , vol.41 , pp. 163-181
    • Capdevila, J.H.1    Falck, J.R.2    Harris, R.C.3
  • 7
    • 0035965327 scopus 로고    scopus 로고
    • Epoxygenase pathway of arachidonic acid metabolism
    • D.C. Zeldin Epoxygenase pathway of arachidonic acid metabolism J. Biol. Chem. 276 2001 36059 36062
    • (2001) J. Biol. Chem. , vol.276 , pp. 36059-36062
    • Zeldin, D.C.1
  • 8
    • 0032871226 scopus 로고    scopus 로고
    • 20-HETE and the kidney: Resolution of old problems and new beginnings
    • J.C. McGiff, and J. Quilley 20-HETE and the kidney: resolution of old problems and new beginnings Am. J. Physiol. 277 1999 R607 R623
    • (1999) Am. J. Physiol. , vol.277
    • McGiff, J.C.1    Quilley, J.2
  • 9
    • 0036080081 scopus 로고    scopus 로고
    • P-450 metabolites of arachidonic acid in the control of cardiovascular function
    • R.J. Roman P-450 metabolites of arachidonic acid in the control of cardiovascular function Physiol. Rev. 82 2001 131 185
    • (2001) Physiol. Rev. , vol.82 , pp. 131-185
    • Roman, R.J.1
  • 10
    • 0035955607 scopus 로고    scopus 로고
    • Cytochrome P450 enzymes in vascular homeostasis
    • I. Fleming Cytochrome P450 enzymes in vascular homeostasis Circ. Res. 89 2001 753 762
    • (2001) Circ. Res. , vol.89 , pp. 753-762
    • Fleming, I.1
  • 11
    • 0023936473 scopus 로고
    • Oxidation of 5,8,11,14,17-eicosapentaenoic acid by hepatic and renal microsomes
    • M. Van Rollins, P.D. Frade, and O.A. Carretero Oxidation of 5,8,11,14,17-eicosapentaenoic acid by hepatic and renal microsomes Biochim. Biophys. Acta 966 1988 133 149
    • (1988) Biochim. Biophys. Acta , vol.966 , pp. 133-149
    • Van Rollins, M.1    Frade, P.D.2    Carretero, O.A.3
  • 12
    • 0026086378 scopus 로고
    • Metabolism of polyunsaturated (n-3) fatty acids by monkey seminal vesicles: Isolation and biosynthesis of omega-3 epoxides
    • E.H. Oliw, and H.W. Sprecher Metabolism of polyunsaturated (n-3) fatty acids by monkey seminal vesicles: isolation and biosynthesis of omega-3 epoxides Biochim. Biophys. Acta 1086 1991 287 294
    • (1991) Biochim. Biophys. Acta , vol.1086 , pp. 287-294
    • Oliw, E.H.1    Sprecher, H.W.2
  • 14
    • 0025810346 scopus 로고
    • Urinary excretion of diols derived from eicosapentaenoic acid during n-3 fatty acid ingestion by man
    • H.R. Knapp, A.J. Miller, and J.A. Lawson Urinary excretion of diols derived from eicosapentaenoic acid during n-3 fatty acid ingestion by man Prostaglandins 42 1991 47 54
    • (1991) Prostaglandins , vol.42 , pp. 47-54
    • Knapp, H.R.1    Miller, A.J.2    Lawson, J.A.3
  • 17
    • 0036840527 scopus 로고    scopus 로고
    • Stereospecific activation of cardiac ATP-sensitive K(+) channels by epoxyeicosatrienoic acids: A structural determinant study
    • T. Lu, M. VanRollins, and H.C. Lee Stereospecific activation of cardiac ATP-sensitive K(+) channels by epoxyeicosatrienoic acids: a structural determinant study Mol. Pharmacol. 62 2002 1076 1083
    • (2002) Mol. Pharmacol. , vol.62 , pp. 1076-1083
    • Lu, T.1    Vanrollins, M.2    Lee, H.C.3
  • 18
    • 1642372110 scopus 로고    scopus 로고
    • Arachidonic and eicosapentaenoic acid metabolism by human CYP1A1: Highly stereoselective formation of 17(R),18(S)-epoxyeicosatetraenoic acid
    • D. Schwarz, P. Kisselev, S.S. Ericksen, G.D. Szklarz, A. Chernogolov, H. Honeck, W.-H. Schunck, and I. Roots Arachidonic and eicosapentaenoic acid metabolism by human CYP1A1: highly stereoselective formation of 17(R),18(S)-epoxyeicosatetraenoic acid Biochem. Pharmacol. 67 2004 1445 1457
    • (2004) Biochem. Pharmacol. , vol.67 , pp. 1445-1457
    • Schwarz, D.1    Kisselev, P.2    Ericksen, S.S.3    Szklarz, G.D.4    Chernogolov, A.5    Honeck, H.6    Schunck, W.-H.7    Roots, I.8
  • 19
    • 0027940480 scopus 로고
    • Regio- and stereoselective epoxidation of arachidonic acid by human cytochromes P450 2C8 and 2C9
    • B.E. Daikh, J.M. Lasker, J.L. Raucy, and D.R. Koop Regio- and stereoselective epoxidation of arachidonic acid by human cytochromes P450 2C8 and 2C9 J. Pharmacol. Exp. Ther. 271 1994 1427 1433
    • (1994) J. Pharmacol. Exp. Ther. , vol.271 , pp. 1427-1433
    • Daikh, B.E.1    Lasker, J.M.2    Raucy, J.L.3    Koop, D.R.4
  • 20
    • 0029122098 scopus 로고
    • Molecular cloning, expression and characterization of an endogenous human cytochrome P450 arachidonic acid epoxygenase isoform
    • D.C. Zeldin, R.N. DuBois, J.R. Falck, and J.H. Capdevila Molecular cloning, expression and characterization of an endogenous human cytochrome P450 arachidonic acid epoxygenase isoform Arch. Biochem. Biophys. 322 1995 76 86
    • (1995) Arch. Biochem. Biophys. , vol.322 , pp. 76-86
    • Zeldin, D.C.1    Dubois, R.N.2    Falck, J.R.3    Capdevila, J.H.4
  • 22
    • 0032725975 scopus 로고    scopus 로고
    • The kidney cytochrome P-450 2C23 arachidonic acid epoxygenase is upregulated during dietary salt loading
    • V.R. Holla, K. Makita, P.G. Zaphiropoulos, and J.H. Capdevila The kidney cytochrome P-450 2C23 arachidonic acid epoxygenase is upregulated during dietary salt loading J. Clin. Invest. 104 1999 751 760
    • (1999) J. Clin. Invest. , vol.104 , pp. 751-760
    • Holla, V.R.1    Makita, K.2    Zaphiropoulos, P.G.3    Capdevila, J.H.4
  • 24
    • 0035090669 scopus 로고    scopus 로고
    • Differential metabolism of benzo[a]pyrene and benzo[a]pyrene-7,8- dihydrodiol by human CYP1A1 variants
    • D. Schwarz, P. Kisselev, I. Cascorbi, W.-H. Schunck, and I. Roots Differential metabolism of benzo[a]pyrene and benzo[a]pyrene-7,8-dihydrodiol by human CYP1A1 variants Carcinogenesis 22 2001 453 459
    • (2001) Carcinogenesis , vol.22 , pp. 453-459
    • Schwarz, D.1    Kisselev, P.2    Cascorbi, I.3    Schunck, W.-H.4    Roots, I.5
  • 25
    • 0025033331 scopus 로고
    • Synthesis of epoxyeicosatrienoic acids and heteroatom analogs
    • J.R. Falck, P. Yadagiri, and J.H. Capdevila Synthesis of epoxyeicosatrienoic acids and heteroatom analogs Methods Enzymol. 187 1990 357 364
    • (1990) Methods Enzymol. , vol.187 , pp. 357-364
    • Falck, J.R.1    Yadagiri, P.2    Capdevila, J.H.3
  • 27
    • 78651165715 scopus 로고
    • The carbon monoxide-binding pigment of liver microsomes
    • T. Omura, and R. Sato The carbon monoxide-binding pigment of liver microsomes J. Biol. Chem. 239 1964 2370 2378
    • (1964) J. Biol. Chem. , vol.239 , pp. 2370-2378
    • Omura, T.1    Sato, R.2
  • 28
    • 0017088267 scopus 로고
    • Some properties of detergent-solubilized NADPH-cytochrome c (cytochrome P450) reductase purified by biospecific affinity chromatography
    • Y. Yasukochi, and B.S. Masters Some properties of detergent-solubilized NADPH-cytochrome c (cytochrome P450) reductase purified by biospecific affinity chromatography J. Biol. Chem. 251 1976 5335 5344
    • (1976) J. Biol. Chem. , vol.251 , pp. 5335-5344
    • Yasukochi, Y.1    Masters, B.S.2
  • 29
    • 0030586792 scopus 로고    scopus 로고
    • Dexamethasone induces bisallylic hydroxylation of polyunsaturated fatty acids by rat liver microsomes
    • L. Hoernsten, J. Bylund, and E.H. Oliw Dexamethasone induces bisallylic hydroxylation of polyunsaturated fatty acids by rat liver microsomes Arch. Biochem. Biophys. 332 1996 261 268
    • (1996) Arch. Biochem. Biophys. , vol.332 , pp. 261-268
    • Hoernsten, L.1    Bylund, J.2    Oliw, E.H.3
  • 30
    • 0026655077 scopus 로고
    • Biosynthesis of prostaglandins from 17(18)epoxyeicosatetraenoic acid, a cytochrome P-450 metabolite of eicosapentaenoic acid
    • E.H. Oliw, S. Okamoto, L. Hornsten, and F. Sato Biosynthesis of prostaglandins from 17(18)epoxyeicosatetraenoic acid, a cytochrome P-450 metabolite of eicosapentaenoic acid Biochim. Biophys. Acta 1126 1992 261 268
    • (1992) Biochim. Biophys. Acta , vol.1126 , pp. 261-268
    • Oliw, E.H.1    Okamoto, S.2    Hornsten, L.3    Sato, F.4
  • 31
  • 32
    • 0035216255 scopus 로고    scopus 로고
    • Longchain n-3 polyunsaturated fatty acids and blood vessel function
    • M.Y. Abeywardena, and R.J. Head Longchain n-3 polyunsaturated fatty acids and blood vessel function Cardiovasc. Res. 52 2001 361 371
    • (2001) Cardiovasc. Res. , vol.52 , pp. 361-371
    • Abeywardena, M.Y.1    Head, R.J.2
  • 33
    • 0030051805 scopus 로고    scopus 로고
    • Identification of epoxyeicosatrienoc acids as endothelium-derived hyperpolarizing factors
    • W.B. Campbell, D. Gebremedhin, P.F. Pratt, and D.R. Harder Identification of epoxyeicosatrienoc acids as endothelium-derived hyperpolarizing factors Circ. Res. 78 1996 415 423
    • (1996) Circ. Res. , vol.78 , pp. 415-423
    • Campbell, W.B.1    Gebremedhin, D.2    Pratt, P.F.3    Harder, D.R.4
  • 35
    • 1542722060 scopus 로고    scopus 로고
    • Cytochrome P450 epoxygenases as EDHF synthase(s)
    • I. Fleming Cytochrome P450 epoxygenases as EDHF synthase(s) Pharmacol. Res. 49 2004 525 533
    • (2004) Pharmacol. Res. , vol.49 , pp. 525-533
    • Fleming, I.1
  • 36
    • 0036828147 scopus 로고    scopus 로고
    • Cytochrome P-450 epoxygenase metabolites of docosahexaenoate potently dilate coronary arterioles by activating large-conductance calcium-activated potassium channels
    • D. Ye, D. Zhang, C. Oltman, K. Dellsperger, H.C. Lee, and M. VanRollins Cytochrome P-450 epoxygenase metabolites of docosahexaenoate potently dilate coronary arterioles by activating large-conductance calcium-activated potassium channels J. Pharmacol. Exp. Ther. 303 2002 768 776
    • (2002) J. Pharmacol. Exp. Ther. , vol.303 , pp. 768-776
    • Ye, D.1    Zhang, D.2    Oltman, C.3    Dellsperger, K.4    Lee, H.C.5    Vanrollins, M.6


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