Synthesis and NMR characterization of the methyl esters of eicosapentaenoic acid monoepoxides

Chemistry and Physics of Lipids

Volumn 159, Issue 1, 2009, Pages 30-37

  Cui, Pei H ^a   Zhang, Wei V ^a   Hook, James ^b   Tattam, Bruce N ^a   Duke, Colin C ^a   Murray, Michael ^a  

^a UNIVERSITY OF SYDNEY   (Australia)

^b UNIVERSITY OF NEW SOUTH WALES   (Australia)

Author keywords

Eicosapentaenoic acid; Epoxy fatty acid; Mass spectrometry; NMR spectroscopy; Polyunsaturated fatty acid

Indexed keywords

ALKENE; BENZOIC ACID DERIVATIVE; CARBENE; CARBON 13; EICOSAPENTAENOIC ACID MONOEPOXIDE; EPOXIDE; ESTER DERIVATIVE; HYDROGEN; ICOSAPENTAENOIC ACID; UNCLASSIFIED DRUG;

ARTICLE; ELECTROSPRAY; HETERONUCLEAR MULTIPLE BOND CORRELATION; HETERONUCLEAR SINGLE QUANTUM COHERENCE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; ISOMER; LIQUID CHROMATOGRAPHY; MASS FRAGMENTOGRAPHY; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL;

BENZOATES; EICOSAPENTAENOIC ACID; ISOMERISM; MAGNETIC RESONANCE SPECTROSCOPY; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION;

EID: 63649128925     PISSN: 00093084     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.chemphyslip.2009.02.005     Document Type: Article

References (19)

1. Adams J., and Gross M.L. Tandem mass spectrometry for collisional activation of alkali-metal-cationized fatty acids: a method for determining double bond location. Anal. Chem. 59 (1987) 1576-1582
2. 2H NMR spectroscopy of pure essential fatty acids for plants and animals. Magn. Res. Chem. 35 (1997) S91-S100
3. Braun S., Kalinowski H.O., and Berger S. 150 and More Basic NMR Experiments (1998), Wiley-VCH, Weinheim
4. Cheng C., and Gross M.L. Applications and mechanisms of charge-remote fragmentation. Mass Spectrom. Rev. 19 (2000) 398-420
5. Christie, W.W., 2008. http://www.lipidlibrary.co.uk.
6. Cui P.H., Duke R.K., and Duke C.C. Monoepoxy octadecadienoates and monoepoxy octadecatrienoates. 1. NMR spectral characterization. Chem. Phys. Lipids 152 (2008) 122-130
7. Cui P.H., Duke R.K., Tattam B.N., and Duke C.C. Monoepoxy octadecadienoates and monoepoxy octadecatrienoates. 2. Mass spectral characterization. Chem. Phys. Lipids 152 (2008) 65-70
8. Fer M., Goulitquer S., Dreano Y., Berthou F., Corcos L., and Amet Y. Determination of polyunsaturated fatty acid monoepoxides by high performance liquid chromatography-mass spectrometry. J. Chromatogr. A 1115 (2006) 1-7
9. Fitzpatrick F.A., Ennis M.D., Baze M.E., Wynalda M.A., McGee J.E., and Liggett W.F. Inhibition of cyclooxygenase activity and platelet aggregation by epoxyeicosatrienoic acids. Influence of stereochemistry. J. Biol. Chem. 261 (1986) 15334-15338
10. Gunstone F.D. High resolution NMR studies of fish oils. Chem. Phys. Lipids 59 (1991) 83-89
11. Lauterbach B., Barbosa-Sicard E., Wang M.H., Honeck H., Kargel E., Theuer J., Schwartzman M.L., Haller H., Luft F.C., Gollasch M., and Schunk W.H. Cytochrome P450-dependent eicosapentaenoic acid metabolites are novel BK channel activators. Hypertension 39 (2002) 609-613
12. Moffat M.P., Ward C.A., Bend J.R., Mock T., Farhangkhoee P., and Karmazyn M. Effects of epoxyeicosatrienoic acids on isolated hearts and ventricular myocytes. Am. J. Physiol. 264 (1993) H1154-H1160
13. Node K., Huo Y., Ruan X., Yang B., Spiecker M., Ley K., Zeldin D.C., and Liao J.K. Anti-inflammatory properties of cytochrome P450 epoxygenase-derived eicosanoids. Science 285 (1999) 1276-1279
14. Sun J., Sui X.X., Bradbury J.A., Zeldin D.C., Conte M.S., and Liao J.K. Inhibition of vascular smooth muscle cell migration by cytochrome P450 epoxygenase-derived eicosanoids. Circ. Res. 90 (2002) 1020-1027
15. VanRollins M. Synthesis and characterization of cytochrome P-450 epoxygenase metabolites of eicosapentaenoic acid. Lipids 25 (1990) 481-490
16. 13C assignments and structural elucidation of n - 3 polyunsaturated fatty acids by the use of a new 2D NMR technique: SAPHIR-HSQC. Chem. Phys. Lipids 94 (1998) 239-250
17. Weintraub N.L., Fang X., Kaduce T.L., VanRollins M., Chatterjee P., and Spector A.A. Epoxide hydrolases regulate epoxyeicosatrienoic acid incorporation into coronary endothelial phospholipids. Am. J. Physiol. 277 (1999) H2098-H2108
18. Yang W., Gauthier K.M., Reddy L.M., Sangras B., Sharma K.K., Nithipatikon K., Falck J.R., and Campbell W.B. Stable 5,6-epoxyeicosatrienoic acid analog relaxes coronary arteries through potassium channel activation. Hypertension 45 (2005) 681-686
19. Ca channels. Am. J. Physiol. 280 (2001) H2430-H2440