Free radical oxidation of coriolic acid (13-(S)-hydroxy-9Z,11E- octadecadienoic acid)

Chemistry and Physics of Lipids

Volumn 134, Issue 2, 2005, Pages 161-171

  Manini, P ^a   Camera, E ^b   Picardo, M ^b   Napolitano, A ^a   D'Ischia, M ^a  

^a UNIVERSITY OF NAPLES FEDERICO II   (Italy)

^b SAN GALLICANO DERMATOLOGICAL INSTITUTE   (Italy)

Author keywords

(1 2)D NMR; Deuterium labeling; Fenton reagent; Linoleic acid; Lipid peroxidation

Indexed keywords

CARBON 13; CORIOLIC ACID; DEUTERIUM; EPOXIDE; ESTER DERIVATIVE; FREE RADICAL; HYDROGEN; KETOL; REAGENT;

ARTICLE; NUCLEAR MAGNETIC RESONANCE; OXIDATION; OXIDATIVE STRESS; PH; PRIORITY JOURNAL; SPECTROSCOPY;

EID: 15244356588     PISSN: 00093084     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.chemphyslip.2005.01.005     Document Type: Article

References (41)

1. J. Aikens, and T.A. Dix Hydrodioxyl (perhydroxyl), peroxyl, and hydroxyl radical-initiated lipid peroxidation of large unilamellar vescicles (liposomes): comparative and mechanistic studies Arch. Biochem. Biophys. 305 1993 516 525
2. A.N. Baer, P.B. Costello, and F.A. Green Free and esterified 13(R,S)-hydroxyoctadecadienoic acids: principal oxygenase products in psoriatic skin scales J. Lipid Res. 31 1990 125 130
3. E. Blee, A.L. Wilcox, L.J. Marnett, and F. Schuber Mechanism of reaction of fatty acid hydroperoxides with soybean peroxygenase J. Biol. Chem. 268 1993 1708 1715
4. J.C. Bronstein, and A.W. Bull Substrate specificity and characterization of partially purified rat liver 13-hydroxyoctadecadienoic acid (13-HODE) dehydrogenase Arch. Biochem. Biophys. 348 1997 219 225
5. M.R. Buchanan, T.A. Haas, M. Lagarde, and M. Guichardant 13-Hydroxyoctadecadienoic acid is the vessel wall chemorepellant factor, LOX J. Biol. Chem. 260 1985 16056 16059
6. G.R. De Meyer, Y.H. Bult, T.J. Verbeuren, and A.G. Herman The role of endothelial cells in the relaxations induced by 13-hydroxy- and 13-hydroperoxylinoleic acid in canine arteries Br. J. Pharmacol. 107 1992 597 603
7. T.A. Dix, and L.J. Marnett Conversion of linoleic acid hydroperoxide to hydroxy, keto, epoxyhydroxy, and trihydroxy fatty acids by hematin J. Biol. Chem. 260 1985 5351 5357
8. F. Engels, G.C. Kessels, P.A. Henricks, and F.P. Nijkamp Preferential formation of 13-hydroxylinoleic acid by human peripheral blood eosinophils Prostaglandins 52 1996 117 124
9. E.N. Frankel, W.E. Neff, W.K. Rohwedder, B.P.S. Khambay, R.F. Garwood, and B.C.L. Weedon Analysis of autoxidized fats by gas chromatography-mass spectrometry. II. Methyl linoleate Lipids 12 1977 908 913
10. M. Frigerio, M. Santagostino, and S. Sputore A user-friendly entry to 2-iodoxybenzoic acid (IBX) J. Org. Chem. 64 1999 4537 4538
11. H.W. Gardner, R. Kleiman, and D. Weisleder Homolytic decomposition of linoleic acid hydroperoxide: identification of fatty acid products Lipids 9 1974 696 706
12. 3 catalyst as a model for similar biochemical reactions. I. Study of oxygen requirement, catalyst and effect of pH Biochim. Biophys. Acta 665 1981 100 112
13. 3 catalyst as a model for similar biochemical reactions. II. Specificity in formation of fatty acid epoxides Biochim. Biophys. Acta 665 1981 113 125
14. N. Godessart, M. Camacho, J. Lopez-Belmonte, R. Anton, M. Garcia, J.M. de Moragas, and L. Vila Prostaglandin H-synthase-2 is the main enzyme involved in the biosynthesis of octadecanoids from linoleic acid in human dermal fibroblasts stimulated with interleukin-1 beta J. Invest. Dermatol. 107 1996 726 732
15. T.A. Haas, E. Bastida, K. Nakamura, F. Hullin, L. Admirall, and M.R. Buchanan Binding of 13-HODE and 5-, 12- and 15-HETE to endothelial cells and subsequent platelet, neutrophil and tumor cell adhesion Biochim. Biophys. Acta 961 1988 153 159
16. M. Hamberg Fatty acid hydroperoxide isomerase in Saprolegnia parasitica: structural studies of epoxy alcohols formed from isomeric hydroperoxyoctadecadienoates Lipids 24 1989 249 255
17. M. Hamberg, and B. Samuelsson Stereochemistry in the formation of 9-hydroxy-10,12-octadecadienoic acid and 13-hydroxy-9,11-octadecadienoic acid from linoleic acid by fatty acid cyclooxygenase Biochim. Biophys. Acta 617 1980 545 547
18. M. Hamberg, and G. Hamberg Hydroperoxide-dependent epoxidation of unsaturated fatty acids in the broad bean (Vicia faba L.) Arch. Biochem. Biophys. 283 1990 409 416
19. P.A. Henricks, F. Engels, H. van der Vliet, and F.P. Nijkamp 9- and 13-Hydroxylinoleic acid possess chemotactic activity for bovine polymorphonuclear leukocytes Prostaglandins 41 1991 21 27
20. T. Iwahama, Y. Yoshino, T. Keitoku, S. Sakaguchi, and Y. Ishii Efficient oxidation of alcohols to carbonyl compounds with molecular oxygen catalyzed by N-hydroxyphthalimide combined with a Co species J. Org. Chem. 65 2000 6502 6507
21. W. Jira, and G. Spiteller Increase in hydroxy fatty acids in human low density lipoproteins with age Chem. Phys. Lipids 84 1996 165 173
22. W. Jira, G. Spiteller, and A. Richter Increased levels of lipid oxidation products in low density lipoproteins of patients suffering from rheumatoid arthritis Chem. Phys. Lipids 87 1997 81 89
23. H. Kühn Biosynthesis, metabolization and biological importance of the primary 15-lipoxygenase metabolites 15-hydro(pero)xy-5Z,8Z,11Z,13E- eicosatetraenoic acid and 13-hydro(pero)xy-9Z,11E-octadecadienoic acid Prog. Lipid Res. 35 1996 203 226
24. D.V. Kuklev, W.W. Christie, T. Durand, J.C. Rossi, J.P. Vidal, S.P. Kasyanov, V.N. Akulin, and V.V. Bezuglov Synthesis of keto- and hydroxydienoic compounds from linoleic acid Chem. Phys. Lipids 85 1997 125 134
25. N. Marx, T. Bourcier, G.K. Sukhova, P. Libby, and J. Plutzky PPARγ activation in human endothelial cells increases plasminogen activator inhibitor type-1 expression-PPARγ as a potential mediator in vascular disease Arterioscler. Thromb. Vasc. Biol. 19 1999 546 551
26. F. Minisci, F. Recupero, A. Cecchetto, C. Gambarotti, C. Punta, R. Faletti, R. Paganelli, and G.F. Pedulli Mechanisms of the aerobic oxidation of alcohols to aldehydes and ketones, catalysed under mild conditions by persistent and non-persistent nitroxyl radicals and transition metal salts - polar, enthalpic, and captodative effects Eur. J. Org. Chem. 2004 109 119
27. F. Minisci, F. Recupero, G.F. Pedulli, and M. Lucarelli Transition metal salts catalysis in the aerobic oxidation of organic compounds. Thermochemical and kinetic aspects and new synthetic developments in the presence of N-hydroxy-derivative catalysts J. Mol. Catal. A 204/205 2003 63 90
28. A. Mlakar, and G. Spiteller Dihydroxy and hydroxyoxo fatty acids as products of nonenzymic lipid peroxidation of polyunsaturated fatty acids Chem. Phys. Lipids 82 1996 25 32
29. L. Nagy, P. Tontonoz, J.G.A. Alvarez, H. Chen, and R.M. Evans Oxidized LDL regulates macrophage gene expression through ligand activation of PPARγ Cell 93 1998 229 240
30. A. Napolitano, E. Camera, M. Picardo, and M. d'Ischia Reactions of hydro(pero)xy derivatives of polyunsaturated fatty acids/esters with nitrite ions under acidic conditions. Unusual nitrosative breakdown of methyl 13-hydro(pero)xyoctadeca-9,11-dienoate to a novel 4-nitro-2-oximinoalk-3-enal product J. Org. Chem. 67 2002 1125 1132
31. W.E. Neff, E.N. Frankel, C.R. Scholfield, and D. Weisleder High-pressure liquid chromatography of autoxidized lipids. I. Methyl oleate and linoleate Lipids 13 1978 414 421
32. Nemann, R., Khenkin, A.M., 1997. In: Patai, S., Rapport, Z. (Eds.), The Chemistry of Dienes and Polyenes, vol. 1, John Wiley and Sons, New York, pp. 1916-1918.
33. N. Reddy, A. Everhart, T. Eling, and W.C. Glasgow Characterization of a 15-lipoxygenase in human breast carcinoma BT-20 cells: stimulation of 13-HODE formation by Tgα/EGF Biochem. Biophys. Res. Commun. 231 1997 111 116
34. C. Schneider, K.A. Tallman, N.A. Porter, and A.R. Brash Two distinct pathways of formation of 4-hydroxynonenal. Mechanisms of nonenzymatic transformation of the 9- and 13-hydroperoxides of linoleic acid to 4-hydroxyalkenals J. Biol. Chem. 276 2001 20831 20838
35. D.J. Sessa, H.W. Gardner, R. Kleiman, and D. Weisleder Oxygenated fatty acid constituents of soybean phosphatidylcholines Lipids 12 1977 613 619
36. T.C. Simon, A.N. Makheja, and J.M. Bailey The induced lipoxygenase in atherosclerotic aorta converts linoleic acid to the platelet chemorepellant factor, 13-HODE Thromb. Res. 55 1989 171 178
37. R.J. Soberman, T.W. Harper, D. Betteridge, R.A. Lewis, and K.F. Austin Characterization and separation of the arachidonic acid 5-lipoxygenase and linoleic acid 6-lipoxygenase (arachidonic acid 15-lipoxygenase) of human polymorphonuclear leukocytes J. Biol. Chem. 260 1985 4508 4515
38. G. Spiteller Linoleic acid peroxidation - the dominant lipid peroxidation process in low density lipoprotein-and its relationship to chronic diseases Chem. Phys. Lipids 95 1998 105 162
39. G. Spiteller Peroxidation of linoleic acid and its relation to aging and age dependent diseases Mech. Ageing Dev. 122 2001 617 657
40. P. Spiteller, and G. Spiteller 9-Hydroxy-10,12-octadecadienoic acid (9-HODE) and 13-hydroxy-9,11-octadecadienoic acid (13-HODE): excellent markers for lipid peroxidation Chem. Phys. Lipids 89 1997 131 139
41. 2 is used as oxidant Biochim. Biophys. Acta 1392 1998 23 40