Olive phenols efficiently inhibit the oxidation of serum albumin-bound linoleic acid and butyrylcholine esterase

Biochimica et Biophysica Acta - General Subjects

Volumn 1790, Issue 4, 2009, Pages 240-248

  Roche, Marjolaine ^a   Dufour, Claire ^a   Loonis, Michèle ^a   Reist, Marianne ^b   Carrupt, Pierre Alain ^b   Dangles, Olivier ^a  

^a UNIVERSITY OF AVIGNON   (France)

^b UNIVERSITY OF GENEVA   (Switzerland)

Author keywords

Antioxidant; Binding site; Butyrylcholine esterase; Lipid peroxidation; Olive phenols; Serum albumin

Indexed keywords

ALPHA TOCOPHEROL; ANTIOXIDANT; ASCORBIC ACID; CAFFEIC ACID; CHLOROGENIC ACID; CHOLINESTERASE; COUMARIC ACID; DIHYDROCAFFEIC ACID; FERULIC ACID; HUMAN SERUM ALBUMIN; HYDROXYTYROSOL; LINOLEIC ACID; OLEUROPEIN; PHENOL DERIVATIVE; QUERCETIN; TYROSOL;

ANTIOXIDANT ACTIVITY; ARTICLE; CONTROLLED STUDY; ENZYME ACTIVITY; HUMAN; HUMAN CELL; INHIBITION KINETICS; LIPID OXIDATION; LIPID PEROXIDATION; OXIDATION; PRIORITY JOURNAL; PROTEIN BINDING; PROTEIN DEGRADATION;

ANTIOXIDANTS; BUTYRYLCHOLINESTERASE; HUMANS; KINETICS; LINOLEIC ACID; LIPID PEROXIDATION; MODELS, CHEMICAL; OLEA; OXIDATION-REDUCTION; PHENOLS; SERUM ALBUMIN;

EID: 61749103682     PISSN: 03044165     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bbagen.2009.01.007     Document Type: Article

References (51)

1. Serdar Z., Aslan K., Dirican M., Sarandöl E., Yesilburca D., and Serdar A. Lipid and protein oxidation and antioxidant status in patients with angiographically proven coronary artery disease. Clin. Biochem. 39 (2006) 794-803
2. Spiteller G. Peroxyls radicals: inductors of neurodegenerative and other inflammatory diseases. Their origin and how they transform cholesterol, phospholipids, plasmalogens, polyunsaturated fatty acids, sugars, and proteins into deleterious products. Free Radic. Biol. Med. 41 (2006) 362-387
3. Butterfield D.A., and Lauderback C.M. Lipid peroxidation and protein oxidation in Alzheimer's disease brain: potential causes and consequences involving amyloid β-peptide-associated free radical oxidative stress. Free Radic. Biol. Med. 32 (2002) 1050-1060
4. Tappel A., and Tappel A. Oxidant free radical initiated chain polymerization of protein and other biomolecules and its relationship to diseases. Med. Hypothesis 63 (2004) 98-99
5. Gilbert D.L., and Colton C.A. Reactive Oxygen Species in Biological Systems: An Interdisciplinary Approach (1999), Kluwer Academic, New-York
6. Elahi M.M., and Matata B.M. Free radicals in blood: evolving concepts in the mechanism of ischemic heart disease. Arch. Biochem. Biophys. 450 (2006) 78-88
7. Frei B., Stocker R., and Ames B.N. Antioxidant defenses and lipid peroxidation in human blood plasma. Proc. Natl. Acad. Sci. 85 (1988) 9748-9752
8. Owen R.W., Giacosa A., Hull W.S.E., et al. Olive-oil comsumption and health: the possible role of antioxidants. Lancet Oncol. 1 (2000) 107-112
9. Limiroli R., Consonni R., Ranalli A., Bianchi G., and Zetta L. 1H-NMR study of phenolics in the vegetation water of three cultivars of olea europaea: similarities and differences. J. Agric. Food Chem. 44 (1996) 2040-2048
10. García A., Brenes M., García P., Romero C., and Garrido A. Phenolic content of commercial olive oils. Eur. Food Res. Technol. 216 (2003) 520-525
11. 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
12. Visioli F., Galli C., Bornet F., et al. Olive oil phenolics are dose-dependently absorbed in humans. FEBS Lett. 468 (2000) 159-160
13. Miró-Casas E., Covas M.I., Fitó M., Farré-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
14. Miró-Casas E., and de la Torre R. Capillary GC-MS quantitative determination of hydroxytyrosol and tyrosol in human urine after olive oil intake. Anal. Biochem. 294 (2001) 63-72
15. Cremin P., Kasim-Karakas S., and Waterhouse A. A. L. LC/ES-MS detection of hydroxycinnamates in human plasma and urine. J. Agric. Food Chem. 49 (2001) 1747-1750
16. Rechner A.R., Spencer J.P.E., Kuhnle G., Hahn U., and Rice-Evans C. Novel biomarkers of the metabolism of caffeic acid derivatives in vivo. Free Radic. Biol. Med. 30 (2001) 1213-1222
17. Bogani P., Galli C., Villa M., and Visioli F. Postprandial, anti-inflammatory and antioxidant effects of extra virgin olive oil. Atherosclerosis 190 (2007) 181-186
18. Fki I., Bouaziz M., Sahnoun Z., and Sayadi S. Hypocholesterolemic effects of phenolic-rich extracts of Chemlali olive cultivar in rats fed a cholesterol-rich diet. Bioorg. Med. Chem. 13 (2005) 5362-5370
19. Gonzalez-Santiago M., Martin-Bautista E., Carrero J.J., et al. One-month administration of hydroxytyrosol, a phenolic antioxidant present in olive oil, to hyperlipidemic rabbits improves blood lipid profile, antioxidant status and reduces atherosclerosis development. Atherosclerosis 188 (2006) 35-42
20. Léger C.L., Kadiri-Hassani N., and Descomps B. Decreased superoxide anion production in cultured human promonocyte cells (THP-1) due to polyphenol mixtures from olive oil processing wastewaters. J. Agric. Food Chem. 48 (2000) 5061-5067
21. D'Angelo S., Ingrosso D., Migliardi V., et al. 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
22. Perona J.S., Cabello-Moruno R., and Ruiz-Gutierrez V. The role of olive oil components in the modulation of endothelial function. J. Nutr. Biochem. 17 (2006) 429-445
23. Bouzid O., Navarro D., Roche M., et al. Fungal enzymes as a powerful tool to release simple phenolic compounds from olive oil by-product. Process Biochem. 40 (2005) 1855-1862
24. Roche M., Dufour C., Mora N., and Dangles O. Antioxidant activity of olive phenols: mechanistic investigation and characterisation of oxidation products by mass spectrometry. Org. Biomol. Chem. 3 (2005) 423-430
25. Covas M.I., de la Torre K., Farre-Albaladejo M., et al. Postprandial LDL phenolic content and LDL oxidation are modulated by olive oil phenolic compounds in humans. Free Radic. Biol. Med. 40 (2006) 608-616
26. Peters T. All About Albumin: Biochemistry, Genetics and Biomedical Applications (1996), Academic Press, San Diego
27. Bourdon E., Loreau N., Lagrost L., and Blache D. Differencial effects of cysteine and methionine residues in the antioxidant activity of human serum albumin. Free Radic. Biol. Med. 39 (2005) 15-20
28. Ogasawara Y., Namai T., Togawa T., and Ishii K. Formation of albumin dimers induced by exposure to peroxides in human plasma: a possible biomarker for oxidative stress. Biochim. Biophys. Acta 340 (2006) 353-358
29. Petitpas I., Grüne T., Bhattacharya A.A., and Curry S. Crystal structures of human serum albumin complexed with monounsatured and polyunsatured fatty acids. J. Mol. Biol. 314 (2001) 955-960
30. Dufour C., and Dangles O. Flavonoid-serum albumin complexation: determination of binding constants and binding site by fluorescence spectroscopy. Biochim. Biophys. Acta 172 (2005) 164-173
31. Zsila F., Bikadi Z., and Simonyi M. Probing the binding of the flavonoid, quercetin to human serum albumin by circular dichroism, electronic absorption spectroscopy and molecular modelling methods. Biochem. Pharmacol. 65 (2003) 447-456
32. Jiang M., Xie M.-X., Zheng D., Liu Y., Li X.-Y., and Chen X. Spectroscopic studies on the interaction of cinnamic acid and its hydroxyl derivatives with human serum albumin. J. Mol. Struct. 692 (2004) 71-80
33. Kang J., Liu Y., Xie M.-X., Li S., Jiang M., and Wang Y.-D. Interactions of human serum albumin with chlorogenic acid and ferulic acid. Biochim. Biophys. Acta 1674 (2004) 205-214
34. Dufour C., and Loonis M. Flavonoids and their oxidation products efficiently protect albumin-bound linoleic acid in a model of plasma oxidation. Biochim. Biophys. Acta 1770 (2007) 958-965
35. Dufour C., Loonis M., and Dangles O. Inhibition of the peroxidation of linoleic acid by the flavonoid quercetin within their complex with human serum albumin. Free Radic. Biol. Med. 43 (2007) 241-252
36. Soreq H., Seidman S., Dreyfus P.A., Zevin-Sonkin D., and Zakut H. Expression and tissue-specific assembly of human butyrylcholine esterase in microinjected Xenopus laevis oocytes. J. Biol. Chem. 264 (1989) 10608-10613
37. Chapuis N., Brühlmann C., Reist M., Carrupt P.-A., Mayer J.M., and Testa B. The esterase-like activity of serum albumin may be due to cholinesterase contamination. Pharm. Res. 18 (2001) 1435-1439
38. Kálmán J., Juhász A., Rakonczay Z., et al. Increased serum butyrylcholinesterase activity in type IIb hyperlipidaemic patients. Life Sci. 75 (2004) 1195-1204
39. Salvi A., Brühlmann C., Migliavacca E., Carrupt P.-A., Hostettmann K., and Testa B. Protein protection by antioxidants: development of a convenient assay and structure-activity relationships of natural polyphenols. Helv. Chim. Acta 85 (2002) 867-881
40. Monteiro M., Farah A., Perrone D., Trugo L.C., and Donangelo C. Chlorogenic acid compounds from coffee are differentially absorbed and metabolized in humans. J. Nutr. 137 (2007) 2196-2201
41. Dufour C., and Loonis M. Regio- and stereoselective oxidation of linoleic acid bound to serum albumin: identification by ESI-mass spectrometry and NMR of the oxidation products. Chem. Phys. Lipids 138 (2005) 60-68
42. Epps D.E., Raub T.J., and Caiolfa V. Determination of the affinity of drugs toward serum albumin by measurement of the quenching of the intrinsic tryptophan fluorescence of the protein. J. Pharm. Pharmacol. 51 (1999) 41-48
43. Sudlow G., Birkett D.J., and Wade D.N. Further characterization of specific drug binding sites on human serum albumin. Mol. Pharmacol. 12 (1976) 1052-1061
44. Epps D.E., Raub T.J., and Kezdy F.J. A general, wide-range spectrofluorometric method for measuring the site-specific affinities of drugs toward human serum albumin. Anal. Biochem. 227 (1995) 342-350
45. Bagatolli L.A., Kivatinitz S.C., and Fidelio G.D. Interaction of small ligands with human serum albumin IIIA subdomain. How to determine the affinity constant using easy steady state fluorescent method. J. Pharm. Sci. 85 (1996) 1131-1132
46. Niki E., Yoshida Y., Saito Y., and Noguchi N. Lipid peroxidation: mechanisms, inhibition, and biological effects. Biochem. Biophys. Res. Comm. 338 (2005) 668-676
47. Liu W., and Wang J.-Y. Modifications of protein by polyunsaturated fatty acid ester peroxidation products. Biochim. Biophys. Acta 1752 (2005) 93-98
48. Refsgaard H.H.F., Tsai L., and Stadtman R. Modifications of proteins by polyunsaturated fatty acid peroxidation products. Proc. Natl. Acad. Sci. 97 (2000) 611-616
49. Manach C., Morand C., Crespy V., et al. Quercetin is recovered in human plasma as conjugated derivatives which retain antioxidant properties. FEBS Lett. 426 (1998) 331-336
50. Filipe P., Morliere P., Patterson L.K., et al. Mechanisms of flavonoid repair reactions with amino acid radicals in models of biological systems: a pulse radiolysis study in micelles and human serum albumin. Biochim. Biophys. Acta 1572 (2002) 150-162
51. Silvester J.A., Timmins G.S., and Davis M.J. Photodynamically generated bovine serum albumin radicals: evidence for damage transfer and oxidation at cysteine and tryptophan residues. Free Radic. Biol. Med. 24 (1998) 754-766