Atherosclerosis
Volume 182, Issue 1 , Pages 47-55 , September 2005

Increased plasma concentrations of Palmitoylethanolamide, an endogenous fatty acid amide, affect oxidative damage of human low-density lipoproteins: An in vitro study

  • Giovanna Zolese

      Affiliations

    • Istituto di Biochimica, via Ranieri 65, Università Politecnica delle Marche, Ancona 60131, Italy
    • Corresponding Author InformationCorresponding author. Tel.: +39 071 2204673; fax: +39 071 2204398.
    • ,
  • Tiziana Bacchetti

      Affiliations

    • Istituto di Biochimica, via Ranieri 65, Università Politecnica delle Marche, Ancona 60131, Italy
    • ,
  • Annarina Ambrosini

      Affiliations

    • Istituto di Biochimica, via Ranieri 65, Università Politecnica delle Marche, Ancona 60131, Italy
    • ,
  • Michal Wozniak

      Affiliations

    • Department of General Chemistry, University of Gdansk, Gdansk, Poland
    • ,
  • Enrico Bertoli

      Affiliations

    • Istituto di Biochimica, via Ranieri 65, Università Politecnica delle Marche, Ancona 60131, Italy
    • ,
  • Gianna Ferretti

      Affiliations

    • Istituto di Biochimica, via Ranieri 65, Università Politecnica delle Marche, Ancona 60131, Italy

Received 9 June 2004 ,Revised 30 November 2004 ,Accepted 17 January 2005.

References 

  1. Hansen HS, Moesgaard B, Hansen HH, Petersen G. N-Acylethanolamines and precursor phospholipids—relation to cell injury. Chem Phys Lipids. 2000;108:135–150
  2. Giuffrida A, Piomelli D. Isotope dilution GC/MS determination of anandamide and other fatty acylethanolamides in rat blood plasma. FEBS Lett. 1998;422:373–376
  3. Giuffrida A, Rodriguez de Fonseca F, Piomelli D. Quantification of bioactive acylethanolamides in rat plasma by electrospray mass spectrometry. Anal Biochem. 2000;280:87–93
  4. Giuffrida A, Rodriguez de Fonseca F, Nava F, Loubet-Lescoulie P, Piomelli D. Elevated circulating levels of anandamide after administration of the transport inhibitor, AM404. Eur J Pharmacol. 2000;408:161–168
  5. Wang Y, Liu Y, Ito Y, et al. Simultaneous measurement of anandamide and 2-arachidonoylglycerol by polymyxin B-selective adsorption and subsequent high-performance liquid chromatography analysis: increase in endogenous cannabinoids in the sera of patients with endotoxic shock. Anal Biochem. 2001;294:73–82
  6. Schmid HHO, Schmid PC, Natarajan V. N-Acylated glycerophospholipids and their derivatives. Prog Lipid Res. 1990;29:1–43
  7. Schmid HHO, Schmid PC, Berdyshev EV. Cell signaling by endocannabinoids and their congeners: questions of selectivity and other challenges. Chem Phys Lipids. 2002;121:111–134
  8. De Petrocellis L, Melck D, Bisogno T, Di Marzo V. Endocannabinoids and fatty acid amides in cancer, inflammation and related disorders. Chem Phys Lipids. 2000;108:191–209
  9. Berdyshev EV, Schmid PC, Krebsbach RJ, et al. Cannabinoid-receptor-independent cell signalling by N-acylethanolamines. Biochem J. 2001;360:67–75
  10. Mechoulam R, Fride E, Di Marzo V. Endocannabinoids. Eur J Pharmacol. 1998;359:1–18
  11. Jonsson KO, Vandevoorde S, Lambert DM, Tiger G, Fowler CJ. Effects of homologues and analogues of palmitoylethanolamide upon the inactivation of the endocannabinoid anandamide. Br J Pharmacol. 2001;133:1263–1275
  12. Fowler CJ. Plant-derived, synthetic and endogenous cannabinoids as neuroprotective agents. Non-psychoactive cannabinoids, ‘entourage’ compounds and inhibitors of N-acyl ethanolamine breakdown as therapeutic strategies to avoid pyschotropic effects. Brain Res Brain Res Rev. 2003;41:26–43
  13. Lambert DM, Vandevoorde S, Jonssonand KO, Fowler CJ. The palmitoylethanolamide family: a new class of anti-inflammatory agents?. Curr Med Chem. 2002;9:663–674
  14. Schmid HH, Berdyshev EV. Cannabinoid-receptor-inactive N-acylethanolamines and other fatty acid amides: metabolism and function. Prostaglandins Leukot Essent Fatty Acids. 2002;66:363–376
  15. Ross RA, Brockie HC, Pertwee RG. Inhibition of nitric oxide production in RAW264.7 macrophages by cannabinoids and palmitoylethanolamide. Eur J Pharmacol. 2000;401:121–130
  16. Ambrosini A, Zolese G, Wozniak M, et al. Idiopathic infertility: susceptibility of spermatozoa to in-vitro capacitation, in the presence and the absence of palmitylethanolamide (a homologue of anandamide), is strongly correlated with membrane polarity studied by Laurdan fluorescence. Mol Hum Reprod. 2003;9:381–388
  17. Zolese G, Wozniak M, Mariani P, Saturni L, Bertoli E, Ambrosini A. Different modulation of phospholipase A2 activity by saturated and monounsaturated N-acylethanolamines. J Lipid Res. 2003;44:742–753
  18. Berdyshev EV, Boichot E, Germain N, Allain N, Anger JP, Lagente V. Influence of fatty acid ethanolamides and delta9-tetrahydrocannabinol on cytokine and arachidonate release by mononuclear cells. Eur J Pharmacol. 1997;330:231–240
  19. Lepicier P, Bouchard JF, Lagneux C, Lamontagne D. Endocannabinoids protect the rat isolated heart against ischaemia. Br J Pharmacol. 2003;139:805–815
  20. Gulaya NM, Kuzmenko AI, Margitich VM, et al. Long-chain N-acylethanolamines inhibit lipid peroxidation in rat liver mitochondria under acute hypoxic hypoxia. Chem Phys Lipids. 1998;97:49–54
  21. Parinandi NL, Schmid HH. Effects of long-chain N-acylethanolamines on lipid peroxidation in cardiac mitochondria. FEBS Lett. 1988;237:49–52
  22. Knott HM, Baoutina A, Davies MJ, Dean RT. Comparative time-courses of copper-ion-mediated protein and lipid oxidation in low-density lipoprotein. Arch Biochem Biophys. 2002;400:223–232
  23. Ambrosini A, Bertoli E, Mariani P, Tanfani F, Wozniak M, Zolese G. N-acylethanolamines as membrane topological stress compromising agents. Biochim Biophys Acta. 1993;1148:351–355
  24. Kerry NL, Abbey M. The isoflavone genistein inhibits copper and peroxyl radical mediated low-density lipoprotein oxidation in vitro. Atherosclerosis. 1998;140:341–347
  25. Jiang ZY, Hunt JV, Wolff SP. Ferrous ion oxidation in the presence of xylenol orange for detection of lipid hydroperoxides in low-density lipoprotein. Anal Biochem. 1992;2020:384–389
  26. Buege JA, Aust SD. Microsomal lipid peroxidation. Methods Enzymol. 1978;52:302–310
  27. Chung BH, Segrest JP, Ray MJ, et al. Single vertical spin density gradient ultracentrifugation. Methods Enzymol. 1986;128:181–209
  28. Abuja PM, Liebmann P, Hayn M, Schauenstein K, Esterbauer H. Anti-oxidant role of melatonin in lipid peroxidation of human LDL. FEBS Lett. 1997;413:289–293
  29. Abuja PM, Lohner K, Prassl R. Modification of the lipid-protein interaction in human low-density lipoprotein destabilizes ApoB-100 and decreases oxidizability. Biochemistry. 1999;38:3401–3408
  30. Ziouzenkova O, Sevanian A, Abuja PM, Ramos P, Esterbauer H. Copper can promote oxidation of LDL by markedly different mechanisms. Free Rad Biol Med. 1998;24:607–623
  31. Esterbauer H, Striegl G, Puhl H, Rotheneder M. Continuous monitoring of in vitro oxidation of human low-density lipoprotein. Free Radic Res Commun. 1989;6:67–75
  32. Bradford MM. A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding. Anal Biochem. 1976;72:248–254
  33. Brunelli R, Mei G, Krasnowska EK, et al. Estradiol enhances the resistance of LDL to oxidation by stabilizing apoB-100 conformation. Biochemistry. 2000;39:13897–13903
  34. Parasassi T, Bittolo-Bon G, Brunelli R, et al. Loss of apoB-100 secondary structure and conformation in hydroperoxide rich, electronegative LDL(−). Free Rad Biol Med. 2001;31:82–89
  35. Zolese G, Falcioni G, Bertoli E, et al. Steady-state and time resolved fluorescence of albumins interacting with N-oleylethanolamine, a component of the endogenous N-acylethanolamines. Proteins. 2000;40:39–48
  36. Greenfield NJ. Methods to estimate the conformation of proteins and polypeptides from circular dichroism data. Anal Biochem. 1996;235:1–10
  37. Giessauf A, Steiner E, Esterbauer H. Early destruction of tryptophan residues of apolipoprotein B is a vitamin E-independent process during copper-mediated oxidation of LDL. Biochim Biophys Acta. 1995;1256:221–232
  38. Parasassi T, De Stasio G, D’Ubaldo A, Gratton E. Phase fluctuation in phospholipid membranes revealed by Laurdan fluorescence. Biophys J. 1990;57:1179–1186
  39. Parasassi T, De Stasio G, Ravagnan G, Rusch RM, Gratton E. Quantitation of lipid phases in phospholipid vesicles by the generalized polarization of Laurdan fluorescence. Biophys J. 1991;60:179–189
  40. Lapenna D, de Gioia S, Ciofani G, et al. Anti-oxidant properties of ticlopidine on human low-density lipoprotein oxidation. FEBS Lett. 1998;436:357–360
  41. Maziere C, Auclair M, Maziere JC. Lipophilic beta-blockers inhibit monocyte and endothelial cell-mediated modification of low-density lipoproteins. Biochim Biophys Acta. 1992;1126:314–318
  42. Wiseman H, Paganga G, Rice-Evans C, Halliwell B. Protective actions of tamoxifen and 4-hydroxytamoxifen against oxidative damage to human low-density lipoproteins: a mechanism accounting for the cardioprotective action of tamoxifen?. Biochem J. 1993;292:635–638
  43. Bojesen IN, Hansen HS. Binding of anandamide to bovine serum albumin. J Lipid Res. 2003;44:1790–1794
  44. Hevonoja T, Pentikainen MO, Hyvonen MT, Kovanen PT, Ala-Korpela M. Structure of low-density lipoprotein (LDL) particles: basis for understanding molecular changes in modified LDL. Biochim Biophys Acta. 2000;1488:189–210
  45. Bonnefont-Rousselot D, Rouscilles A, Bizard C, Delattre J, Jore D, Gardes-Albert M. Anti-oxidant effect of ethanol toward in vitro peroxidation of human low-density lipoproteins initiated by oxygen free radicals. Radiat Res. 2001;155:279–287
  46. Schuster B, Prassl R, Nigon F, Chapman MJ, Laggner P. Core lipid structure is a major determinant of the oxidative resistance of low-density lipoprotein. Proc Natl Acad Sci USA. 1995;92:2509–2513
  47. Pietzsch J, Julius U. Different susceptibility to oxidation of proline and arginine residues of apolipoprotein B-100 among subspecies of low-density lipoproteins. FEBS Lett. 2001;491:123–126
  48. Filipe P, Morliere P, Patterson LK, et al. Repair of amino acid radicals of apolipoprotein B100 of low-density lipoproteins by flavonoids. A pulse radiolysis study with quercetin and rutin. Biochemistry. 2002;41:11057–11064
  49. Giessauf A, van Wickern B, Simat T, Steinhart H, Esterbauer H. Formation of N-formylkynurenine suggests the involvement of apolipoprotein B-100 centered tryptophan radicals in the initiation of LDL lipid peroxidation. FEBS Lett. 1996;389:136–140
  50. Salvemini D, Cuzzocrea S. Oxidative stress in septic shock and disseminated intravascular coagulation. Free Rad Biol Med. 2002;33:1173–1185

PII: S0021-9150(05)00121-8

doi: 10.1016/j.atherosclerosis.2005.01.043

Atherosclerosis
Volume 182, Issue 1 , Pages 47-55 , September 2005

Article Tools

* Image Usage & Resolution