Synthesis and antioxidant activity of nitrohydroxytyrosol and its acyl derivatives

Journal of Agricultural and Food Chemistry

Volumn 62, Issue 42, 2014, Pages 10297-10303

  Trujillo, Mariana ^a   Gallardo, Elena ^a   Madrona, Andrés ^a   Bravo, Laura ^b   Sarriá, Beatriz ^b   González Correa, José A ^c   Mateos, Raquel ^b   Espartero, José Luis ^a  

^a UNIVERSITY OF SEVILLE   (Spain)

^b INSTITUTE OF FOOD SCIENCE   (Spain)

^c UNIVERSIDAD DE MÁLAGA   (Spain)

Author keywords

antioxidant activity; hydroxytyrosol; nitrocatechol; nitroester derivatives; Parkinsons disease

Indexed keywords

ACYL DERIVATIVES; ANTI-OXIDANT ACTIVITIES; HYDROXYTYROSOL; NITROCATECHOL; PARKINSONS DISEASE;

3,4-DIHYDROXYPHENYLETHANOL; ANTIOXIDANT; PHENETHYL ALCOHOL;

ANALOGS AND DERIVATIVES; CHEMICAL STRUCTURE; CHEMISTRY; OXIDATION REDUCTION REACTION; SYNTHESIS;

ANTIOXIDANTS; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; PHENYLETHYL ALCOHOL;

EID: 84908402940     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/jf503543x     Document Type: Article

References (41)

1. Martin-Pelaez, S.; Covas, M. I.; Fito, M.; Kusar, A.; Pravst, I. Health effects of olive oil polyphenols: recent advances and possibilities for the use of health claims Mol. Nutr. Food Res. 2013, 57, 760-771
2. EFSA Panel on Dietetic Products, Nutrition and Allergies. EFSA J. 2011, 9, 2033-2058.
3. Guasch-Ferre, M.; Hu, F. B.; Martinez-Gonzalez, M. A.; Fito, M.; Bullo, M.; Estruch, R.; Ros, E.; Corella, D.; Recondo, J.; Gomez-Gracia, E.; Fiol, M.; Lapetra, J.; Serra-Majem, L.; Munoz, M. A.; Pinto, X.; Lamuela-Raventos, R. M.; Basora, J.; Buil-Cosiales, P.; Sorli, J. V.; Ruiz-Gutierrez, V.; Martinez, J. A.; Salas-Salvado, J. Olive oil intake and risk of cardiovascular disease and mortality in the PREDIMED Study BMC Med. 2014, 12, 78 10.1186/1741-7015-12-78
4. Khalatbary, A. R. Olive oil phenols and neuroprotection Nutr. Neurosci. 2013, 16, 243-249
5. Mateos, R.; Espartero, J. L.; Trujillo, M.; Rios, J. J.; Leon-Camacho, M.; Alcudia, F.; Cert, A. Determination of phenols, flavones, and lignans in virgin olive oils by solid-phase extraction and high-performance liquid chromatography with diode array ultraviolet detection J. Agric. Food Chem. 2001, 49, 2185-2192
6. Mateos, R.; Pereira-Caro, G.; Saha, S.; Cert, R.; Redondo-Horcajo, M.; Bravo, L.; Kroon, P. A. Acetylation of hydroxytyrosol enhances its transport across differentiated CaCo-2 cell monolayers Food Chem. 2011, 125, 865-872
7. Mateos, R.; Goya, L.; Bravo, L. Metabolism of olive oil phenols hydroxytyrosol, tyrosol, and hydroxytyrosyl acetate by human hepatoma HepG2 cells J. Agric. Food Chem. 2005, 53, 9897-9905
8. Mateos, R.; Trujillo, M.; Pereira-Caro, G.; Madrona, A.; Cert, A.; Espartero, J. L. New lipophilic tyrosyl esters. Comparative antioxidant evaluation with hydroxytyrosyl esters J. Agric. Food Chem. 2008, 56, 10960-10966
9. Pereira-Caro, G.; Mateos, R.; Sarria, B.; Cert, R.; Goya, L.; Bravo, L. Hydroxytyrosyl acetate contributes to the protective effects against oxidative stress of virgin olive oil Food Chem. 2012, 131, 869-878
10. Grasso, S.; Siracusa, L.; Spatafora, C.; Renis, M.; Tringali, C. Hydroxytyrosol lipophilic analogues: enzymatic synthesis, radical scavenging activity and DNA oxidative damage protection Bioorg. Chem. 2007, 35, 137-152
11. Bouallagui, Z.; Bouaziz, M.; Lassoued, S.; Engasser, J. M.; Ghoul, M.; Sayadi, S. Hydroxytyrosol acyl esters: biosynthesis and activities Appl. Biochem. Biotechnol. 2011, 163, 592-599
12. Gonzalez-Correa, J. A.; Navas, M. D.; Lopez-Villodres, J. A.; Trujillo, M.; Espartero, J. L.; De La Cruz, J. P. Neuroprotective effect of hydroxytyrosol and hydroxytyrosol acetate in rat brain slices subjected to hypoxia-reoxygenation Neurosci. Lett. 2008, 446, 143-146
13. Gordin, A.; Kaakkola, S.; Teravainen, H. Clinical advantages of COMT inhibition with entacapone-a review J. Neural Transm. 2004, 111, 1343-1363
14. Bonifacio, M. J.; Palma, P. N.; Almeida, L.; Soares-da-Silva, P. Cathecol- O -methyltransferase and its inhibitors in Parkinson diseases CNS Drugs 2007, 13, 352-379
15. Lautala, P.; Kivimaa, M.; Salomies, H. Glucuronidation of entacapone, nitecapone, tolcapone and some other nitrocatechols by rat liver microsomes Pharm. Res. 1997, 14, 1444-1448
16. Fernández-Bolaños, J.; Heredia, A.; Rodríguez, G.; Rodríguez, R.; Jiménez, A.; Gillen, R. Methods for obtaining purified hydroxytyrosol from products and byproducts derived from the olive tree. U.S. 6849,770 B2, 2005.
17. Napolitano, A.; Panzella, L.; Savarese, M.; Sacchi, R.; Giudicianni, I.; Paolillo, L.; dIschia, M. Acid-induced structural modifications of unsaturated fatty acids and phenolic olive oil constituents by nitrite ions: a chemical assessment Chem. Res. Toxicol. 2004, 17, 1329-1337
18. Pulido, R.; Bravo, L.; Saura-Calixto, F. Antioxidant activity of dietary polyphenols as determined by a modified ferric reducing/antioxidant power assay J. Agric. Food Chem. 2000, 48, 3396-3402
19. Re, R.; Pellegrini, N.; Proteffente, A.; Pannala, A.; Yang, M.; Rice-Evans, C. Antioxidant activity applying an improved ABTS radical cation decolouration assay Free Radical Biol. Med. 1999, 26, 1231-1237
20. Huang, D.; Ou, B.; Hampsch-Woodill, M.; Flanagan, J. A.; Deemer, E. K. Development and validation of oxygen radical absorbance capacity assay for lipophilic antioxidants using randomly methylated ?-cyclodextrin as the solubility enhancer J. Agric. Food Chem. 2002, 50, 1815-1821
21. Alcudia, F.; Cert, A.; Espartero, J. L.; Mateos, R.; Trujillo, M. Method of preparing hydroxytyrosyl esters, esters thus obtained and use of same. PCT WO 2004/005237, 2004.
22. Trujillo, M.; Mateos, R.; Collantes de Teran, L.; Espartero, J. L.; Cert, R.; Jover, M.; Alcudia, F.; Bautista, J.; Cert, A.; Parrado, A. Lipophilic hydroxytyrosyl esters. Antioxidant activity in lipid matrices and biological systems J. Agric. Food Chem. 2006, 54, 3779-3785
23. Balsano, C.; Alisi, A. Antioxidant effects of natural bioactive compounds Curt. Pharm. Des. 2009, 15, 3063-3073
24. Visioli, F.; Bernardini, E. Extra virgin olive oils polyphenols: biological activities Curr. Pharm. Design. 2011, 17, 786-804
25. Ting, H.; Xiao-Wei, H.; Jian-Guo, J.; Xin-Lin, X. Hydroxytyrosol and its potential therapeutic effects J. Agric. Food Chem. 2014, 62, 1449-1455
26. Fernandez-Bolaños, J. G.; Lopez, O.; Fernandez-Bolaños, J.; Rodriguez-Gutierrez, G. Hydroxytyrosol and derivatives: isolation, synthesis and biological properties Curr. Org. Chem. 2008, 12, 442-463
27. Chillemi, R.; Sciuto, S.; Spatafora, C.; Tringali, C. Hydroxytyrosol lipophilic analogues: synthesis, radical scavenging activity and human cell oxidative damage protection. In Olives and Olive Oil in Health and Disease Prevention; Preedy, V. R.; Watson, R. R., Eds.; Academic Press: New York, 2010; pp 1233-1243.
28. Pokorny, J. Major factors affecting the antioxidant of lipids. In Autoxidation of Unsaturated Lipids; Chan, H., Ed.; Academic Press: London, UK, 1987; pp 141-206.
29. Chimi, H.; Cillard, J.; Cillard, P.; Rahmani, M. Peroxyl radical scavenging activity of some natural phenolic antioxidants J. Am. Oil Chem. Soc. 1991, 68, 307-312
30. Porter, W.; Black, E. D.; Drolet, A. M. Use of a polyamide oxidative fluorescence test on lipid emulsions: contrast in relative effectiveness of antioxidant in bulk versus dispersed systems J. Agric. Food Chem. 1989, 37, 615-624
31. Madrona, A.; Pereira-Caro, G.; Bravo, L.; Mateos, R.; Espartero, J. L. Preparation and antioxidant activity of tyrosyl and homovanillyl ethers Food Chem. 2011, 129, 1169-1178
32. Laguerre, M.; Giraldo, L. J.; Lecomte, J.; Figueroa-Espinoza, M. C.; Barea, B.; Weiss, J. Chain length affects antioxidant properties of chlorogenate esters in emulsion: the cutoff theory behind the polar paradox J. Agric. Food Chem. 2009, 57, 11335-11342
33. Laguerre, M.; Lopez-Giraldo, L. J.; Lecomte, J.; Figueroa-Espinoza, M. C.; Barea, B.; Weiss, J.; Decker, E. A.; Villeneuve, P. Relationship between hydrophobicity and antioxidant ability of phenolipids in emulsion: A parabolic effect of the chain length of rosmarinate esters J. Agric. Food Chem. 2010, 58, 2869-2876
34. Pereira-Caro, G.; Madrona, A.; Bravo, L.; Espartero, J. L.; Alcudia, F.; Cert, A.; Mateos, R. Antioxidant activity evaluation of alkyl hydroxytyrosyl ethers, a new class of hydroxytyrosol derivatives Food Chem. 2009, 115, 86-91
35. Laguerre, M.; Bayrasy, C.; Lecomte, J.; Chabi, B.; Decker, E. A.; Wrutniak-Cabello, C.; Cabello, G.; Villeneuve, P. How to boost antioxidants by lipophilization? Biochimie 2013, 95, 20-26
36. Laguerre, M.; Lecomte, J.; Villeneuve, P. The physico-chemical basis of phenolic antioxidant activity Lipid Technol. 2014, 26, 59-62
37. Laguerre, M.; Bayrasy, C.; Panya, A.; Weiss, J.; McClements, D. J.; Lecomte, J.; Decker, E. A.; Villeneuve, P. What makes good antioxidants in lipid-based systems? The next theories beyond the polar paradox Crit. Rev. Food Sci. Nutr. 2015, 55, 183-201
38. Locatelli, C.; Rosso, R.; Santos-Silva, M. C.; De Souza, C. A.; Licínio, M. A.; Leal, P.; Bazzo, M. L.; Yunes, R. A.; Creczynski-Pasa, T. B. Ester derivatives of gallic acid with potential toxicity toward L1210 leukemia cells Bioorg. Med. Chem. 2008, 16, 3791-3799
39. Reyes, J. J.; De la Cruz, J. P.; Munoz-Marin, J.; Guerrero, A.; Lopez-Villodres, J. A.; Madrona, A.; Espartero, J. L.; Gonzalez-Correa, J. A. Antiplatelet effect of new lipophilic hydroxytyrosol alkyl ether derivatives in human blood Eur. J. Nutr. 2013, 52, 591-599
40. Muñ-Marin, J.; De La Cruz, J. P.; Reyes, J. J.; López-Villodres, J. A.; Guerrero, A.; López-Leiva, I.; Espartero, J. L.; Labajos, M. T.; González-Correa, J. A. Hydroxytyrosyl alkyl ether derivatives inhibit platelet activation after oral administration to rats Food Chem. Toxicol. 2013, 58, 295-300
41. Calderon-Montano, J. M.; Madrona, A.; Burgos-Moron, E.; Orta, M. L.; Mateos, R.; Espartero, J. L.; Lopez-Lazaro, M. Selective cytotoxic activity of new lipophilic hydroxytyrosol alkyl ether derivatives J. Agric. Food Chem. 2013, 61, 5046-5053