Production of triacetylhydroxytyrosol from olive mill waste waters for use as stabilized bioantioxidant

Journal of Agricultural and Food Chemistry

Volumn 54, Issue 24, 2006, Pages 9063-9070

  Capasso, Renato ^a   Sannino, Filomena ^a   De Martino, Antonio ^a   Manna, Caterina ^b  

^a UNIVERSITY OF NAPLES FEDERICO II   (Italy)

^b SECOND UNIVERSITY OF NAPLES   (Italy)

Author keywords

Bioantioxidants; Chromatographic purification; Continuous liquid liquid extraction; Hydroxytyrosol; Olive mill waste waters; Triacetylhydroxytyrosol

Indexed keywords

4-HYDROXYPHENYLETHANOL; ANTIOXIDANT; DRUG DERIVATIVE; PHENETHYL ALCOHOL; TYROSOL;

ARTICLE; BIOREACTOR; CHEMISTRY; EVALUATION; HUMAN; INDUSTRIAL WASTE; LIQUID CHROMATOGRAPHY; OLIVE TREE;

ANTIOXIDANTS; BIOREACTORS; CHROMATOGRAPHY, LIQUID; HUMANS; INDUSTRIAL WASTE; OLEA; PHENYLETHYL ALCOHOL;

EID: 33845665333     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf061290r     Document Type: Article

References (38)

1. Manna, C.; Della Ragione, F.; Cucciola, V.; Borriello, A.; D'Angelo, S.; Galletti, P.; Zappia, V. Biological effects of hydroxytyrosol, a polyphenol from olive oil endowed with antioxidant activity. Adv. Exp. Med. Biol. 1999, 472, 115-130.
2. Capasso, R.; Evidente, A.; Avolio, S.; Solla, F. A highly convenient synthesis of hydroxytyrosol and its recovery from agricultural waste waters. J. Agric. Food Chem. 1999, 47, 1745-1748.
3. Allouche, N.; Fki, I.; Sayadi, S. Toward a high yield recovery of antioxidants and purified hydroxytyrosol from olive mill wastewaters. J. Agric. Food Chem. 2004, 52, 267-273.
4. Ferdinando-Bolanos, J.; Rodriguez, G.; Rodriguez, R.; Heredia, A.; Guillen, R.; Jimenez, A. Production in large quantities of highly purified hydroxytyrosol from liquid-solid waste of two-phase olive oil processing or Alperujo. J. Agric. Food Chem. 2002, 50, 6804-6811.
5. Brenes, M.; Garcia, A.; Garcia, P.; Rios, J.; Garrido, A. Phenolic compounds in Spanish olive oils. J. Agric. Food Chem. 1999, 47, 3535-3540.
6. Gordon, M. H.; Martins, F. P.; Almenda, M. Antioxidant activity of hydroxytyrosol acetate as compared with that of other olive oil polyphenols. J. Agric. Food Chem. 2001, 49, 2480-2495.
7. Visioli, F.; Bellomo, G.; Galli, C. Free radical scavenging properties of olive oil polyphenols. Biochem. Biophys. Res. Commun. 1998, 247, 60-64.
8. Ranalli, A.; Lucera, L.; Contento, S. Antioxidizing potency of phenol compounds in olive oil mill wastewater. J. Agric. Food Chem. 2003, 57, 7636-7641.
9. Manna, C.; Galletti, P.; Cucciola, V.; Moltedo, O.; Leone, A.; Zappia, V. The protective effect of olive oil polyphenols (3,4-dihydroxyphenyl)-ethanol counteracts reactive oxygen metabolite-induced cytotoxicity in Caco-2-cells. J. Nutr. 1997, 127, 286-292.
10. Manna, C.; Migliardi, V.; Golino, P.; Scognamiglio, A.; Galletti, P.; Chiariello, M.; Zappia, V. Oleuropein prevents oxidative myocardial injury induced by ischemia and reperfusion. J. Nutr. Biochem. 2004, 15, 461-466.
11. Visioli, F.; Caruso, D; Galli, C.; Viappiani, S.; Galli, G.; Sala, A. Olive oils rich in natural catecholic phenols decrease isoprostane excretion in humans. Biochem. Biophys. Res. Commun. 2000, 278, 797-799.
12. Scaccini, C.; Nardini, M.; D'Aquino, M.; Gentili, V.; Di Felice, M.; Tomassi, G. Effect of dietary oils on lipid peroxidation and on antioxidant parameters of rat plasma and lipoprotein fractions. J. Lipid Res. 1992, 33, 627-633.
13. Wiseman, S. A.; Mathot, J. N.; de Fouw, N. J.; Tijburg, L. B. Dietary non-tocopherol antioxidants present in extra virgin olive oil increase the resistance of low density lipoproteins to oxidation in rabbits. Atherosclerosis 1996, 120, 15-22.
14. Owen, R. W.; Giacosa, A.; Hull, W. E.; Haubner, R.; Wurtele, G.; Spiegelhalder, B.; Bartsch, H. Olive oil consumption and health: the possible role of antioxidants. Lancet Oncol. 2000, 1, 107-112.
15. Visioli, F.; Galli, C. Biological properties of olive oil phytochemicals. Crit. Rev. Food Sci. Nutr. 2002, 42, 209-221.
16. Tuck, K. L.; Hayball, P. J. Major phenolic compounds in olive oil: metabolism and health effects. J. Nutr. Biochem. 2002, 13, 636-644.
17. Manna, C.; Galletti, P.; Maisto, G.; Cucciolla, V.; D'Angelo, S.; Zappia, V. Transport mechanism and metabolism of olive oil hydroxytyrosol in Caco-2 cells. FEBS Lett. 2000, 470, 341-344.
18. Visioli, F.; Galli, C.; Bornet, F.; Mattei, A.; Patelli, R.; Galli, G.; Caruso, D. Olive oil phenolics are dose-dependently absorbed in humans. FEBS Lett. 2000, 468, 159-160.
19. D'Angelo, S.; Manna, C.; Migliardi, V.; Mazzoni, O.; Morsica, P.; Capasso, G.; Pontoni, G.; Galletti, P.; Zappia, V. Pharmacokinetics and metabolism of hydroxytrosol, a natural antioxidant from olive oil. Drug Metab. Dispos. 2001, 29, 1492-1498.
20. Manna, C.; Migliardi, V.; Sannino, F.; De Martino, A.; Capasso, R. Protective effects of the synthetic hydroxytyrosol acetyl derivatives against oxidative stress in human cells. J. Agric. Food Chem. 2005, 53, 9602-9607.
21. Chikamatsu, Y; Ando, H.; Yamamoto, A; Kyo, S.; Yamashita, K.; Dojo, K. Hydroxytyrosol as melanin and lipid peroxide formation inhibitor and its application to topical and bath preparations. Japanese Patent 8119825, 1996; pp 1-10.
22. Espin, J. C.; Soler-Rivas, E.; Cantos, F. A.; Tomas-Barberan, H. J.; Wichers, X. Synthesis of the antioxidant hydroxytyrosol using tyrosinase as biocatalyst. J. Agric. Food Chem. 2001, 49, 1187-1193.
23. Allouche, N.; Damak, M.; Ellouz, R.; Sayadi, S. Use of whole cells of Pseudomonas aeruginosa for synthesis of the antioxidant hydroxytyrosol via conversion of tyrosol. Appl. Environ. Microbiol. 2004, 70, 2105-2109.
24. Chakborti, A. K.; Gulhane R. Perchloric acid adsorbed on silica gel as a new, highly efficient, and versatile catalyst for acetylation of phenols, thiols, alcohols, and amines. Chem. Commun. 2003, 1896-1897.
25. Benzie, I. F. F.; Strain, J. J. Ferric reducing/antioxidant power assay: Direct measure of total antioxidant activity of biological fluids and modified version for simultaneous measurement of total antioxidant power and ascorbic acid concentration. Methods Enzymol. 1999, 299, 15-27.
26. Denizot, F.; Lang, R. Rapid colorimetric assay for cell growth and survival. Modifications to the tetrazolium dye procedure giving improved sensitivity and reliability. J. Immunol. Methods 1986, 89, 271-277.
27. Sannino, F.; De Martino, A.; Capasso, R.; Allouche, N.; Sayadi, S. Recovery of hydroxytyrosol from olive mill wastewater by two different continuous liquid-liquid extraction procedures. Polyphenol. Commun. 2004, 803-804.
28. Sannino, F.; De Martino, A.; Capasso, R.; Allouche, N.; Sayadi, S. Ibid, XXII International Conference on Polyphenols: August 25-28, 2004, Helsinki, Finland.
29. Capasso, R.; Evidente, A.; Scognamiglio, F. Isolation, spectroscopy, and selective phytotoxic effects of polyphenols from vegetable wastewaters. Phytochemistry 1992, 31, 4125-4128.
30. Capasso, R. A review on the electron ionization and fast atom bombardment mass spectrometry of polyphenols naturally occurring in olive wastes and of their synthetic derivatives. Phytochem. Anal. 1999, 10, 299-306.
31. Geerlings, A.; Lopez-Huertas, L. E.; Morales, S. J. C.; Boza, P. J.; Jimenez Lopez, J. Natural compounds and derivatives thereof, including tyrosol and hydroxytyrosol esters with fatty acids, for the prevention and treatment of cardiovascular, hepatic, and renal diseases and for cosmetic applications. International Patent 2003082798, 2003; pp 1-39.
32. Capasso, R.; De Martino, A.; Arienzo, M. Recovery and characterization of the metal polymeric organic fraction (polymerin) from olive oil mill waste waters. J. Agric. Food Chem. 2002, 50, 2846-2855.
33. Capasso, R.; De Martino, A.; Cristinzio, G. Production, characterization, and effects on tomato of humic acid-like polymerin metal derivatives from olive oil mill waste waters. J. Agric. Food Chem. 2002, 50, 4018-4024.
34. Katan, M. B.; De Roos, N. M. Promises and problems of functional foods. Crit. Rev. Food Sci. Nutr. 2004, 44, 369-377.
35. Kwon, T. W.; Hong, J. H.; Moon, G. S.; Song, Y. S.; Kim, J. I.; Kim, J. C.; Kim, M. J. Food technology: challenge for health promotion. Biofactors 2004, 22, 279-287.
36. Hirata, T. Key factors for the success of functional foods. Biofactors 2004, 22, 289-294.
37. Mantena, S. K.; Kativar, S. K. Grape seed proanthocyanidins inhibit UV radiation-induced oxidative stress and activation of MAPK and NF-kappaB signaling in human epidermal keratinocytes. Free Radical Biol. Med. 2006, 40, 1603-1614.
38. Sajia, A.; Tomaino, A.; Trombetta, D.; De Pasquale, A.; Uccella, N.; Barbuzzi, T.; Paolino, D.; Bonina, F. In vitro and in vivo evaluation of caffeic acids as topical photoprotective agents. Int. J. Pharm. 2000, 199, 39-47.