Protective activity of hydroxytyrosol metabolites on erythrocyte oxidative-induced hemolysis

Journal of Agricultural and Food Chemistry

Volumn 61, Issue 27, 2013, Pages 6636-6642

  Paiva Martins, Fátima ^a   Silva, Aníbal ^a   Almeida, Vasco ^a   Carvalheira, Mafalda ^a   Serra, Cristina ^a   Rodrígues Borges, José Enrique ^a   Fernandes, João ^a,b   Belo, Luis ^a,b   Santos Silva, Alice ^a,b  

^a UNIVERSITY OF PORTO   (Portugal)

^b UNIVERSITY OF PORTO   (Portugal)

Author keywords

erythrocytes; glucuronides; homovanillyl alcohol; hydroxytyrosol; hydroxytyrosol acetate; olive oil; polyphenols

Indexed keywords

DOSE-DEPENDENT MANNER; ERYTHROCYTES; GLUCURONIDES; HYDROXYTYROSOL; OXIDATIVE INJURY; POLYPHENOLS; RADICAL INITIATORS; RED BLOOD CELL;

METABOLITES; OLIVE OIL; VOLATILE FATTY ACIDS;

BLOOD;

3,4-DIHYDROXYPHENYLETHANOL; ANTIOXIDANT; DRUG DERIVATIVE; HYDROXYTYROSOL; PHENETHYL ALCOHOL; PROTECTIVE AGENT;

ADULT; ARTICLE; CYTOLOGY; DRUG EFFECT; ERYTHROCYTE; FEMALE; HEMOLYSIS; HUMAN; MALE; METABOLISM; MIDDLE AGED; OXIDATIVE STRESS;

ADULT; ANTIOXIDANTS; ERYTHROCYTES; FEMALE; HEMOLYSIS; HUMANS; MALE; MIDDLE AGED; OXIDATIVE STRESS; PHENYLETHYL ALCOHOL; PROTECTIVE AGENTS;

EID: 84879998893     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/jf4016202     Document Type: Article

References (36)

1. López-Miranda, J.; Pérez-Jiménez, F.; Ros, E.; De Caterina, R.; Badimón, L.; Covas, M. I. Olive oil and health: Summary of the II international conference on olive oil and health consensus report, Jaén and Córdoba (Spain) 2008 Nutr., Metab. Cardiovasc. Dis. 2010, 20, 284-29
2. Visioli, F.; Bernardini, E. Extra virgin olive oil's polyphenols: Biological activities Curr. Pharm. Des. 2011, 17, 786-804
3. Frankel, E. N. Nutritional and biological properties of extra virgin olive oil J. Agric. Food Chem. 2011, 59, 785-792
4. Fitó, M.; Covas, M. I.; Lamuela-Raventós, R. M.; Vila, J.; Torrents, J.; de la Torre, C.; Marrugat, J. Protective effect of olive oil and its phenolic compounds against low density lipoprotein oxidation Lipids 2000, 35, 633-638
5. Leenen, R.; Roodenburg, A. J. C.; Vissers, M. N.; Schuubiers, J. A. E.; van Putte, K. P. A. M.; Wiseman, S. A.; van de Put, F. H. M. M. Supplementation of plasma with olive oil phenols and extracts: Influence on LDL oxidation J. Agric. Food Chem. 2002, 50, 1290-1297
6. Martín-Peláez, S.; Covas, M. I.; Fitó, M.; Kušar, A.; Pravst, I. Health effects of olive oil polyphenols: Recent advances and possibilities for the use of health claims Mol. Nut. Food Res. 2013, 57, 760-771
7. Covas, M.-I.; de la Torre, K.; Farré-Albaladejo, M.; Kaikkonen, J.; Fitó, M.; López-Sabater, C.; Pujadas-Bastardes, M. A.; Joglar, J.; Weinbrenner, T.; Lamuela-Raventós; de la Torre, R. Posprandial LDL phenolic content and LDL oxidation are modulated by olive oil phenolic compounds in humans Free Radical Biol. Med. 2006, 40, 608-616
8. Raederstorff, D. Antioxidant activity of olive polyphenols in humans: A review Int. J. Vitam. Nutr. Res. 2009, 79, 152-165
9. García, A.; Brenes, M.; Martínez, F.; Alba, J.; García, P.; Garrido, A. High-performance liquid chromatography evaluation of phenols in virgin olive oil during extraction at laboratory and industrial scale J. Am. Oil Chem. Soc. 2001, 78, 625-629
10. Tovar, M. J.; Moltiva, M. J.; Romero, M. P. Changes in the phnolic composition of virgin olive oil from young trees (Olea europaea L. cv. Arbequina) Grown under linear irrigation strategies J. Agric. Food Chem. 2001, 49, 5502-5508
11. Garcia, B.; Magalhães, J.; Fregapane, G.; Salvador, M. D.; Paiva-Martins, F. Potential of selected Portuguese cultivars for the production of high quality monovarietal virgin olive oil Eur. J. Lipid Sci. Technol. 2012, 114, 1070-1082
12. Corona, G.; Tzounis, X.; DessIgrave, M. A.; Deiana, M.; Debnam, E. S.; Visioli, F.; Spencer, J. P. E. The fate of olive oil polyphenols in the gastrointestinal tract: Implications of gastric and colonic microflora-dependent biotransformation Free Radical Res. 2006, 40, 647-658
13. Miró-Casas, E.; Covas, M.; Fitó, M.; Farré- Albadalejo, M.; Marugat, J.; de la Torre, R. Tyrosol and hydroxytyrosol are absorbed from moderate and sustained doses of virgin olive oil in humans Eur. J. Clin. Nutr. 2003, 57, 186-190
14. Suárez, M.; Valls, R. M.; Romero, M.-P.; MacIà, A.; Fernández, S.; Giralt, M.; Solà, R.; Motilva, M.-J. Bioavailability of phenols from a phenol-enriched olive oil Br. J. Nutr. 2011, 106, 1691-1701
15. Rubió, L.; Valls, R.-M.; Macià, A.; Pedret, A.; Giralt, M.; Romero, M.-P.; de la Torre, R.; Covas, M. I.; Solà, R.; Moltiva, M. J. Impact of olive oil concentration on human plasmatic phenolic metabolites Food Chem. 2012, 135, 2922-2929
16. Pinto, J.; Paiva-Martins, F.; Corona, G.; Debnam, E. S.; Oruna-Concha, M. J.; Vauzour, D.; Gordon, M. H.; Spencer, J. P. E. Absorption and metabolism of olive oil secoiridoids in the small intestine Br. J. Nutr. 2011, 105, 1607-1618
17. Van der Berg, J. J. M.; Op den Kamp, J. A. F.; Lubin, B. H.; Roelofsen, B.; Kuypers, F. A. Kinetics and site specificity of hydroperoxide-induced oxidative damage in red blood cells Free Radical Biol. Med. 1992, 12, 487-498
18. Rother, R. P.; Bell, L.; Hillmen, P.; Gladwin, M. T. The clinical sequelae of intravascular hemolysis and extracellular plasma hemoglobin: a novel mechanism of human disease JAMA, J. Am. Med. Assoc. 2005, 293, 1653-1662
19. Bamm, V. V.; Tsemakhovich, V. A.; Shaklai, N. Oxidation of low-density lipoprotein by hemoglobin-hemichrome Int. J. Biochem. Cell Biol. 2003, 35, 349-358
20. Grubina, R.; Huang, Z.; Shiva, S.; Joshi, M. S.; Azarov, I.; Basu, S.; Ringwood, L. A.; Jiang, A.; Hogg, N.; Kim-Shapiro, D. B.; Gladwin, M. T. Concerted nitric oxide formation and release from the simultaneous reactions of nitrite with deoxy and oxyhemoglobin J. Biol. Chem. 2007, 282, 12916-12927
21. Jensen, F. B. The dual roles of red blood cells in tissue oxygen delivery: oxygen carriers and regulators of local blood flow J. Exp. Biol. 2009, 212, 3387-3393
22. May, J. M.; Qu, Z.; Cobb, C. E. Extracellular reduction of ascorbate free radical by human erythrocytes Biochem. Biophys. Res. Commun. 2000, 267, 118-123
23. Baraldi, P. G.; Simoni, D.; Manfredini, S.; Menziani, E. Preparation of 3,4-dihydroxy-1-benzeneethanol: A reinvestigation Liebigs Ann. Chem. 1983, 684-686
24. Bernini, R.; Mincione, E.; Barontini, M.; Crisante, F. Convenient synthesis of hydroxytyrosol and its lipophilic derivatives from tyrosol or homovanillyl alcohol J. Agric. Food Chem. 2008, 56, 8897-8904
25. Lucas, R.; Alcantara, D.; Morales, J. C. A concise synthesis of glucuronide metabolites of urolithin-B, resverastrol, and hydroxytyrosol Carbohydr. Res. 2009, 344, 1340-1346
26. Khymenets, O.; Joglar, J.; Clapés, P.; Parella, T.; Covas, M. I.; de la Torre, R. Biocatalyzed synthesis and structural characterization of monoglucuronides of hydroxytyrosol, tyrosol, homovanillic alcohol, and 3-(4′-hydroxyphenyl)propanol Adv. Synth. Catal. 2006, 348, 2155-2162
27. Ko, F. N.; Hsiao, G.; Kuo, Y. H. Protection of oxidative hemolysis by demethyldiisoeugenol in normal and β-thalassemic red blood cells Free Radical Biol. Med. 1997, 22, 215-222
28. Blakney, G. B.; Dinwoodie, A. J. A spectrophotometric scanning technique for the rapid determination of plasma hemoglobin Clin. Biochem. 1975, 8, 96-102
29. Lewis, S. M.; Roper, D. In Dacie and Lewis Practical Haematology; Lewis, S. M.; Bain, B. J.; Bates, I., Eds.; Churchill Livingstone: Philadelphia, PA, 2002; pp 149-198.
30. Manna, C.; Galletti, P.; Cucciolla, V.; Montedoro, G.; Zappia, V. Olive oil hydroxytyrosol protects human erythrocytes against oxidative damages J. Nutr. Biochem. 1999, 10, 159-65
31. Paiva-Martins, F.; Fernandes, J.; Rocha, S.; Nascimento, H.; Vitorino, R.; Amado, F.; Borges, F.; Belo, L.; Santos-Silva, A. Effects of olive oil polyphenols on erythrocyte oxidative damage Mol. Nutr. Food Res. 2009, 53, 609-616
32. Menéndez, C.; Duenãs, M.; Galindo, P.; González- Manzano, S.; Jiménez, R.; Moreno, L.; Zarzuelo, M. J.; Rodríguez-Gómez, I.; Duarte, J.; Santos-Buelga, C.; Perez-Vizcaino, F. Vascular deconjugation of quercetin glucuronide: The flavonoid paradox revealed? Mol. Nutr. Food Res. 2011, 55, 1-11
33. Hennekens, C. H. Update on Aspirin in the treatment and prevention of cardiovascular disease Am. J. Man. Care 2002, 8, 691-700
34. Covas, M.-I.; de la Torre, K.; Farré-Albaladejo, M.; Kaikkonen, J.; Fito, M.; López-Sabater, C.; Pujadas-Bastardes, M. A.; Joglar, J.; Weinbrenner, T.; Lamuela-Raventós; de la Torre, R. Posprandial LDL phenolic content and LDL oxidation are modulated by olive oil phenolic compounds in humans Free Radical Biol. Med. 2006, 40, 608-616
35. Weinbrenner, T.; Fitó, M.; De la Torre, R.; Sáez, G. T.; Rijken, P.; Tormos, C.; Coolen, S.; Albaladejo, M. F.; Abanades, S.; Schroder, H.; Marrugat, J.; Covas, M. I. Olive oils high in phenolic compounds modulate oxidative/antioxidative status in men J. Nutr. 2004, 134, 2314-2321
36. Marrugat, J.; Covas, M. I.; Fitó, M.; Schroder, H.; Miró-Casas, E.; Gimeno, E.; Lopez-Sabater, M. C.; De la Torre, R.; Farré, M. SOLOS Investigators. Effect of differing phenolic content in dietary olive oils on lipids and LDL oxidation Eur. J. Nutr. 2004, 43, 140-147-147