Protective effect of hydroxytyrosol and its metabolite homovanillic alcohol on H2O2 induced lipid peroxidation in renal tubular epithelial cells

Food and Chemical Toxicology

Volumn 46, Issue 9, 2008, Pages 2984-2990

  Deiana, Monica ^a   Incani, Alessandra ^a   Rosa, Antonella ^a   Corona, Giulia ^a   Atzeri, Angela ^a   Loru, Debora ^a   Paola Melis, M ^a   Assunta Dessi M ^a  

^a UNIVERSITY OF CAGLIARI   (Italy)

Author keywords

Cholesterol; Homovanillic alcohol; Hydroxytyrosol; Lipid peroxidation; LLC PK1; Unsaturated fatty acids

Indexed keywords

4 HYDROXY 3 METHOXYPHENYLETHANOL; 7 OXOCHOLESTEROL; ALPHA TOCOPHEROL; CHOLESTEROL; HOMOVANILLIC ACID; HYDROGEN PEROXIDE; HYDROPEROXIDE; HYDROXYTYROSOL; MALONALDEHYDE; MEMBRANE LIPID; UNSATURATED FATTY ACID;

ANIMAL CELL; ANTIOXIDANT ACTIVITY; ARTICLE; CONTROLLED STUDY; CYTOTOXICITY; FATTY ACID ANALYSIS; KIDNEY TUBULE CELL; KIDNEY TUBULE DAMAGE; LIPID PEROXIDATION; MEMBRANE STRUCTURE; NONHUMAN; SWINE;

ALPHA-TOCOPHEROL; ANIMALS; ANTIOXIDANTS; CHOLESTEROL; EPITHELIAL CELLS; FATTY ACIDS, NONESTERIFIED; HOMOVANILLIC ACID; HYDROGEN PEROXIDE; KIDNEY TUBULES; LIPID PEROXIDATION; LLC-PK1 CELLS; MALONDIALDEHYDE; MEMBRANE LIPIDS; OXIDANTS; OXIDATIVE STRESS; PHENYLETHYL ALCOHOL; PROTECTIVE AGENTS; SEROTONIN; SWINE;

SUS;

EID: 50249176439     PISSN: 02786915     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.fct.2008.05.037     Document Type: Article

References (55)

1. Baek S.H., Piao X.L., Lee U.J., Kim H.Y., and Park J.H. Reduction of Cisplatin-induced nephrotoxicity by ginsenosides isolated from processed ginseng in cultured renal tubular cells. Biol. Pharm. Bull. 29 (2006) 2051-2055
2. Banni S., Day B.W., Evans R.W., Corongiu F.P., and Lombardi B. Liquid chromatography - mass spectrometric analysis of conjugated diene fatty acids in a partially hydrogenated fat. JAOCS 71 (1994) 1321-1325
3. Banni S., Carta G., Contini M.S., Angioni E., Deiana M., Dessì M.A., Melis M.P., and Corongiu F.P. Characterization of conjugated diene fatty acids in milk, dairy products and lamb tissues. J. Nutr. Biochem. 7 (1996) 150-155
4. Bonanome A., Pagnan A., Caruso D., Toia A., Xamin A., Fedeli E., Berra B., Zamburlini A., Ursini F., and Galli G. Evidence of postprandial absorption of olive oil phenols in humans. Nutr. Metab. Cardiovasc. Dis. 10 (2000) 111-120
5. Bradford M. Rapid and sensitive method for quantification of protein utilizing the principle of protein-dye binding. Anal. Biochem. 72 (1976) 248-254
6. Caruso D., Visioli F., Patelli R., Galli C., and Galli G. Urinary excretion of olive oil phenols and their metabolites in humans. Metabolism 50 (2001) 1426-1428
7. 2-induced renal epithelial (LLC-PK1) cell injury. Free Radic. Biol. Med. 24 (1998) 49-54
8. Corona G., Tzounis X., Dessi M.A., Deiana M., Debnam E.S., Visioli F., and Spencer J.P.E. The fate of olive oil polyphenols in the gastrointestinal tract: implications of gastric and colonic microflora-dependent biotransformation. Free Rad. Res. 40 (2006) 647-658
9. D'Angelo S., Manna C., Migliardi V., Mazzoni O., Morrica P., Capasso G., Pontoni G., Galletti P., and Zappia V. Pharmacokinetics and metabolism of hydroxytyrosol, a natural antioxidant from olive oil. Drug Metab. Dispos. 29 (2001) 1492-1498
10. D'Angelo S., Ingrosso D., Migliardi V., Sorrentino A., Donnarumma G., Baroni A., Masella L., Tufano M.A., Zappia M., and Galletti P. Hydroxytyrosol, a natural antioxidant from olive oil, prevents protein damage induced by long-wave ultraviolet radiation in melanoma cells. Free Radic. Biol. Med. 38 (2005) 908-919
11. de la Puerta R., Martinez Dominguez M.E., Ruiz-Gutierrez V., Flavill J.A., and Hoult J.R. Effects of virgin olive oil phenolics on scavenging of reactive nitrogen species and upon nitrergic neurotransmission. Life Sci. 69 (2001) 1213-1222
12. de la Torre-Carbot K., Chavez-Servin J.L., Jauregui O., Castellote A.I., Lamuela-Raventos R.M., Fito M., Covas M.I., Munoz-Aguayo D., and Lopez-Sabater M.C. Presence of virgin olive oil phenolic metabolites in human low density lipoprotein fraction: determination by high-performance liquid chromatography-electrospray ionization tandem mass spectrometry. Anal. Chim. Acta 583 (2007) 402-410
13. De Lucia M., Panzella L., Pezzella A., Napolitano A., and d'Ischia M. Oxidative chemistry of the natural antioxidant hydroxytyrosol: hydrogen peroxide-dependent hydroxylation and hydroxyquinone/o-quinone coupling pathways. Tetrahedron 62 (2006) 1273-1278
14. Deiana M., Aruoma O.I., Bianchi M.L., Spencer J.P., Kaur H., Halliwell B., Aeschbach R., Banni S., Dessi M.A., and Corongiu F.P. Inhibition of peroxynitrite dependent DNA base modification and tyrosine nitration by the extra virgin olive oil-derived antioxidant hydroxytyrosol. Free Radic. Biol. Med. 26 (1999) 762-769
15. Del Boccio P., Di Deo A., De Curtis A., Celli N., Iacoviello L., and Rotilio D. Liquid chromatography-tandem mass spectrometry analysis of oleuropein and its metabolite hydroxytyrosol in rat plasma and urine after oral administration. J. Chromatogr. B Analyt. Technol. Biomed. Life Sci. 785 (2003) 47-56
16. Dell'Agli M., Fagnani R., Mitro N., Scurati S., Masciadri M., Mussoni L., Galli G.V., Bosisio E., Crestani M., De Fabiani E., Tremoli E., and Caruso D. Minor components of olive oil modulate proatherogenic adhesion molecules involved in endothelial activation. J. Agric. Food Chem. 54 (2006) 3259-3264
17. Folch J., Lees M., and Sloane Stanley G.H. A simple method for the isolation and purification of total lipides from animal tissues. J. Biol. Chem. 226 (1957) 497-509
18. Gordon M.H., Paiva-Martins F., and Almeida M. Antioxidant activity of hydroxytyrosol acetate compared with that of other olive oil polyphenols. J. Agric. Food Chem. 49 (2001) 2480-2485
19. Gutierrez V.R., de la Puerta R., and Catala A. The effect of tyrosol, hydroxytyrosol and oleuropein on the non-enzymatic lipid peroxidation of rat liver microsomes. Mol. Cell Biochem. 217 (2001) 35-41
20. Kandaswami C., and Middleton Jr. E. Free radical scavenging and antioxidant activity of plant flavonoids. Adv. Exp. Med. Biol. 366 (1994) 351-376
21. Kubo K., Saito M., Tadokoro T., and Maekawa A. Changes in susceptibility of tissues to lipid peroxidation after ingestion of various levels of docosahexaenoic acid and vitamin E. Brit. J. Nutr. 78 (1997) 655-669
22. Manna C., Galletti P., Cucciolla V., Moltedo O., Leone A., and Zappia V. The protective effect of the olive oil polyphenol (3,4-dihydroxyphenyl)-ethanol counteracts reactive oxygen metabolite-induced cytotoxicity in Caco-2 cells. J. Nutr. 127 (1997) 286-292
23. Manna C., Galletti P., Cucciolla V., Montedoro G., and Zappia V. Olive oil hydroxytyrosol protects human erythrocytes against oxidative damages. J. Nutr. Biochem. 10 (1999) 159-165
24. Manna C., Galletti P., Maisto G., Cucciolla V., D'Angelo S., and Zappia V. Transport mechanism and metabolism of olive oil hydroxytyrosol in Caco-2 cells. FEBS Lett. 470 (2000) 341-344
25. Martin-Mateo M.C., Sanchez-Portugal M., Iglesias S., de Paula A., and Bustamante J. Oxidative stress in chronic renal failure. Ren. Fail. 21 (1999) 155-167
26. Meng X., and Reeves W.B. Effects of chloride channel inhibitors on H(2)O(2)-induced renal epithelial cell injury. Am. J. Physiol. Renal Physiol. 278 (2000) F83-F90
27. Miro-Casas E., Covas M.I., Farre M., Fito M., Ortuno J., Weinbrenner T., Roset P., and de la Torre R. Hydroxytyrosol disposition in humans. Clin. Chem. 49 (2003) 945-952
28. Miro-Casas E., Covas M.I., Fito M., Farre-Albadalejo M., Marrugat J., and de la Torre R. Tyrosol and hydroxytyrosol are absorbed from moderate and sustained doses of virgin olive oil in humans. Eur. J. Clin. Nutr. 57 (2003) 186-190
29. Montedoro G., Servili M., Baldioli M., and Miniati E. Simple and hydrolyzable phenolic compounds in Virgin Olive Oil. 1. Their extraction, separation, and quantitative and semiquantitative evaluation by HPLC. J. Agric. Food Chem. 40 (1992) 1571-1576
30. Montedoro G., Servili M., Baldioli M., and Miniati E. Simple and hydrolyzable phenolic compounds in Virgin Olive Oil. 2. Initial characterization of the hydrolyzable fraction. J. Agric. Food Chem. 40 (1992) 1577-1580
31. Mosmann T. Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays. J. Immunol. Methods 65 (1983) 55-63
32. O'Dowd Y., Driss F., Dang P.M., Elbim C., Gougerot-Pocidalo M.A., Pasquier C., and El-Benna J. Antioxidant effect of hydroxytyrosol, a polyphenol from olive oil: scavenging of hydrogen peroxide but not superoxide anion produced by human neutrophils. Biochem. Pharmacol. 68 (2004) 2003-2008
33. Ou Z.L., and Natori Y. Gene expression of CC chemokines in experimental acute tubulointerstitial nephritis. J. Lab. Clin. Med. 133 (1999) 41-47
34. Paiva-Martins F., Gordon M.H., and Gameiro P. Activity and location of olive oil phenolic antioxidants in liposomes. Chem. Phys. Lipids 124 (2003) 23-36
35. Perantoni A., and Berman J.J. Properties of Wilms' tumor line (TuWi) and pig kidney line (LLC-PK1) typical of normal kidney tubular epithelium. In Vitro 15 (1979) 446-454
36. Rice-Evans C.A., Miller N.J., and Paganga G. Structure-antioxidant activity relationships of flavonoids and phenolic acids. Free Radic. Biol. Med. 20 (1996) 933-956
37. Rietjens S.J., Bast A., and Haenen G.R. New insights into controversies on the antioxidant potential of the olive oil antioxidant hydroxytyrosol. J. Agric. Food Chem. 55 (2007) 7609-7614
38. Rodrigo R., and Rivera G. Renal damage mediated by oxidative stress: a hypothesis of protective effects of red wine. Free Radic. Biol. Med. 33 (2002) 409-422
39. Saija A., Trombetta D., Tomaino A., Lo Cascio R., Princi P., Uccella N., and Bonina F. In vitro evaluation of the antioxidant activity and biomembrane interaction of the plant phenols oleuropein and hydroxytyrosol. Int. J. Pharm. 166 (1998) 123-133
40. Salah N., Miller N.J., Paganga G., Tijburg L., Bolwell G.P., and Rice-Evans C. Polyphenolic flavanols as scavengers of aqueous phase radicals and as chain-breaking antioxidants. Arch. Biochem. Biophys. 322 (1995) 339-346
41. 2-induced renal epithelial (LLC-PK1) cell injury. Am. J. Physiol. 268 (1995) F30-F38
42. Schlatter P., Gutmann H., and Drewe J. Primary porcine proximal tubular cells as a model for transepithelial drug transport in human kidney. Eur. J. Pharm. Sci. 28 (2006) 141-154
43. Sheridan A.M., Fitzpatrick S., Wang C., Wheeler D.C., and Lieberthal W. Lipid peroxidation contributes to hydrogen peroxide induced cytotoxicity in renal epithelial cells. Kidney Int. 49 (1996) 88-93
44. Singh D., Kaur R., Chander V., and Chopra K. Antioxidants in the prevention of renal disease. J. Med. Food 9 (2006) 443-450
45. Soobrattee M.A., Neergheen V.S., Luximon-Ramma A., Aruoma O.I., and Bahorun T. Phenolics as potential antioxidant therapeutic agents: mechanism and actions. Mutat. Res. 579 (2005) 200-213
46. Tan H.W., Tuck K.L., Stupans I., and Hayball P.J. Simultaneous determination of oleuropein and hydroxytyrosol in rat plasma using liquid chromatography with fluorescence detection. J. Chromatogr. B - Analyt. Technol. Biomed. Life Sci. 785 (2003) 187-191
47. Templar J., Kon S.P., Milligan T.P., Newman D.J., and Raftery M.J. Increased plasma malondialdehyde levels in glomerular disease as determined by a fully validated HPLC method. Nephrol. Dial. Transplant 14 (1999) 946-951
48. Tuck K.L., and Hayball P.J. Major phenolic compounds in olive oil: metabolism and health effects. J. Nutr. Biochem. 13 (2002) 636-644
49. Tuck K.L., Freeman M.P., Hayball P.J., Stretch G.L., and Stupans I. The in vivo fate of hydroxytyrosol and tyrosol, antioxidant phenolic constituents of olive oil, after intravenous and oral dosing of labeled compounds to rats. J. Nutr. 131 (2001) 1993-1996
50. Tuck K.L., Hayball P.J., and Stupans I. Structural characterization of the metabolites of hydroxytyrosol, the principal phenolic component in olive oil, in rats. J. Agric. Food Chem. 50 (2002) 2404-2409
51. Turner R., Etienne N., Alonso M.G., de Pascual-Teresa S., Minihane A.M., Weinberg P.D., and Rimbach G. Antioxidant and anti-atherogenic activities of olive oil phenolics. Int. J. Vitam. Nutr. Res. 75 (2005) 61-70
52. Visioli F., Caruso D., Galli C., Viappiani S., Galli G., and Sala A. Olive oils rich in natural catecholic phenols decrease isoprostane excretion in humans. Biochem. Biophys. Res. Commun. 278 (2000) 797-799
53. Visioli F., Galli C., Bornet F., Mattei A., Patelli R., Galli G., and Caruso D. Olive oil phenolics are dose-dependently absorbed in humans. FEBS Lett. 468 (2000) 159-160
54. Visioli F., Galli C., Plasmati E., Viappiani S., Hernandez A., Colombo C., and Sala A. Olive phenol hydroxytyrosol prevents passive smoking-induced oxidative stress. Circulation 102 (2000) 2169-2171
55. Vissers M.N., Zock P.L., Roodenburg A.J., Leenen R., and Katan M.B. Olive oil phenols are absorbed in humans. J. Nutr. 132 (2002) 409-417