Toward a High Yield Recovery of Antioxidants and Purified Hydroxytyrosol from Olive Mill Wastewaters

Journal of Agricultural and Food Chemistry

Volumn 52, Issue 2, 2004, Pages 267-273

  Allouche, Noureddine ^a   Fki, Ines ^a   Sayadi, Sami ^a  

^a CENTRE DE BIOTECHNOLOGIE DE SFAX   (Tunisia)

Author keywords

Antioxidants; Continuous extraction; Hydroxytyrosol; Olive mill wastewaters; Polyphenols; Purification

Indexed keywords

ACETIC ACID ETHYL ESTER; ANTIOXIDANT; HYDROXYTYROSOL; SOLVENT; 3,4-DIHYDROXYPHENYLETHANOL; DRUG DERIVATIVE; FLAVONOID; OLIVE OIL; PHENETHYL ALCOHOL; PHENOL DERIVATIVE; POLYPHENOLS; VEGETABLE OIL;

ARTICLE; BATCH PROCESS; CHROMATOGRAPHY; EXTRACTION; LIQUID LIQUID EXTRACTION; OLIVE; PH MEASUREMENT; PURIFICATION; REACTION OPTIMIZATION; WASTE WATER; FOOD HANDLING; ISOLATION AND PURIFICATION; OLIVE TREE; SEWAGE;

ANTIOXIDANTS; FLAVONOIDS; FOOD HANDLING; OLEA; PHENOLS; PHENYLETHYL ALCOHOL; PLANT OILS; WASTE DISPOSAL, FLUID;

EID: 1542289818     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf034944u     Document Type: Article

References (47)

1. Borja, R.; Alba, J.; Banks, C. J. Impact of the main phenolic compounds of olive mill wastewater (OMW) on the kinetics of acetoclastic methanogenesis. Process Biochem. 1997, 32, 121-133.
2. D'Annibale, A.; Crestini, C.; Vinciguerra, V.; Giovannozzi-Sermanni, G. The biodegradation of recalcitrant effluents from an olive mill by a white-rot fungus. J. Biotechnol. 1998, 61, 209-218.
3. Sayadi, S.; Ellouz, R. Roles of lignin peroxidase and manganese peroxidase from Phanerochaete chrysosporium in the decoloration of olive mill wastewaters. Appl. Environ. Microb. 1995, 61, 1098-1103.
4. Benitez, J.; Beltran-Herdia, J.; Torregrosa, J.; Acero, J. L.; Cercas, V. Aerobic degradation of olive mill wastewaters. Appl. Microbiol. Biotechnol. 1997, 47, 185-188.
5. Greco, G., Jr.; Toscano, G.; Cioffi, M.; Gianfreda, L.; Sannino, F. Dephenolisation of olive mill wastewaters by olive husk. Water Res. 1999, 33, 3046-3050.
6. Capasso, R.; Evidente, A.; Schivo, L.; Orrù, G.; Marcialis, M. A. ; Cristinizio, G. Antibacterial polyphenols from olive oil wastewaters. J. Appl. Bacteriol. 1995, 79, 393-398.
7. Sayadi, S.; Allouche, N.; Jaoua, M.; Aloui, F. Detrimental effects of high molecular-mass polyphenols on olive mill wastewater biotreatment. Process Biochem. 2000, 35, 725-735.
8. Servili, M.; Baldioli, M.; Selvaggini, R.; Miniati, E.; Macchioni, A.; Montedoro, G. F. HPLC evaluation of phenols in olive fruit, virgin olive oil, vegetation waters and pomace, and 1D- and 2D-NMR characterization. J. Am. Oil Chem. Soc. 1999, 76, 873-882.
9. Visioli, F.; Romani, A.; Mulinacci, N.; Zarini, S.; Conte, D.; Vincieri, F. F.; Galli, C. Antioxidant and other biological activities of olive mill wastewaters. J. Agric. Food Chem. 1999, 47, 3397-3401.
10. Capasso, R.; Cristinzio, G.; Evidente, A.; Scognamiglio, F. Isolation spectroscopy and selective phytotoxic effects of polyphenols from vegetable wastewaters. Phytochemistry 1992, 31, 4125-4128.
11. Visioli, F.; Vinceri, F. F.; Galli, C. Wastewaters from olive production are rich in natural antioxidants. Experientia 1995, 51, 32-34.
12. Visioli, F.; Poli, A.; Galli, C. Antioxidant and other biological activities of phenols from olives and olive oil. Medi. Res. Rev. 2002, 22(1), 65-75.
13. Badioli, M.; Servili, M.; Peretti, G.; Montedoro, G. F. Antioxidant activity of tocopherols and phenolic compounds in virgin olive oil. J. Am. Oil Chem. Soc. 1997, 79, 1589-1593.
14. Visioli, F.; Bellomo, G.; Galli, C. Free radical scavenging properties of olive oil polyphenols. Biochem. Biophys. Res. Commun. 1998, 247(1), 60-64.
15. Visioli, F.; Caruso, D.; Galli, C.; Viappiani, S.; Galli, G.; Sala, A. Olive oil rich in natural catecholic phenols decrease isoprostane excretion in humans. Biochem. Biophys. Res. Commun. 2000, 278, 797-799.
16. Visioli, F.; Caruso, D.; Galli, C.; Plasmati, E.; Viappiani, S.; Hernandez, A.; Colombo, C.; Sala, A. Olive phenol hydroxytyrosol prevents passive smoking-induced oxidative stress. Circulation 2000, 102, 2169-2171.
17. Auroma, O. I.; Deiane, M.; Jenner, A.; Halliwell, B.; Kaur, M.; Bnni, S. ; Corongiu, F. P.; Dessi, M. A.; Aesbach, R. Effects of hydroxytyrosol found in extra virgin olive oil on oxidative DNA damage and low-density lipoprotein oxidation. J. Agric. Food Chem. 1998, 46, 5181-5187.
18. Petroni, A.; Blasevich, M.; Salami, M.; Papini, N.; Montedoro, G. F.; Galli C. Inhibition of platelet aggregation and eicosanoid production by phenolic component of olive oil. Thromb. Res. 1995, 78, 151-160.
19. De la Puerta, R.; Ruiz-Gutiérrez, V.; Hoult, J. R. Inhibition of leukocyte 5-lipoxygenase by phenolics from virgin olive oil. Biochem. Pharmacol. 1999, 57, 445-449.
20. Manna, C.; Galletti, P.; Cucciolla, 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- cells. J. Nutr. 1997, 127, 286-292.
21. Bisignano, A.; Tomaino, A.; Lo Cascio, R.; Crisafi, G.; Uccella, N.; Saija, A. On the in-vitro antimicrobial activity of oleuropein and hydroxytyrosol. J. Pharm. Pharmacol. 1999, 51, 971-974.
22. Salami, M.; Galli, C.; De Angelis, L.; Visioli, F. Formation of F2-isoprostanes in oxydised low-density lipoprotein: inhibitory effect of hydroxytyrosol. Pharmacol. Res. 1995, 31, 275-279.
23. 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.
24. Tuck, K. L.; Tan, H. W.; Hayball, P. J. Synthesis of tritium-labeled hydroxytyrosol, a phenolic compound found in olive oil. J. Agric. Food Chem. 2000, 48, 4087-4090.
25. Capasso, R.; Evidente, A.; Avolio, S.; Solla, F. A highly convenient synthesis of hydroxytyrosol and its recovery from agricultural wastewaters. J. Agric. Food Chem. 1999, 47, 1745-1748.
26. Bai, C.; Yan, X.; Takenaka, M.; Sekiya, K.; Nagata, T. Determination of synthetic hydroxytyrosol in rat plasma by GC-MS. J. Agric. Food Chem. 1998, 46, 3998-4001.
27. Capasso, R.; Evidente, A.; Visca, C.; Gianfreda, L.; Maremonti, M.; Greco, G. Production of glucose and bioactive aglycone by chemical and enzymatic hydrolysis of purified oleuropein from Olea europaea. Appl. Biochem. Biotechnol. 1996, 60, 365-377.
28. Espin, J. C.; Soler-Rivas, C.; Cantos, E.; Tomas-Barberan, F. A.; Wichers, H. J. Synthesis of the antioxidant hydroxytyrosol using tyrosinase as biocatalyst. J. Agric. Food Chem. 2001, 49, 1187-1193.
29. Capasso, R. The chemistry, biotechnology, and ecotoxicology of the polyphenols naturally occurring in vegetable wastes. Curr. Top. Phytochem. 1997, 1, 145-156.
30. Capasso, R.; Evidente, A.; Visca, C. Production of hydroxytyrosol from olive oil vegetation waters. Agrochimica 1994, 38, 166-171.
31. Bolanos, F. J.; Rodriguez, G.; Rodriguez, R.; Heredia, A.; Guillen, R.; Jimenz, 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.
32. De Tomas, B. F. A.; Ferreres, D. A. F.; Espin, D. G. J. C.; Garcia, V. M.; Wichers, H. J.; Soler, R. C. Enzymatic synthesis of antioxidant hydroxytyrosol. Patent No. EP1310562, 2003.
33. Crea, R. Hydroxytyrosol-rich composition from vegetation water and method of use thereof. Patent No. US2003108651, 2003.
34. Crea, R. Method of obtaining a hydroxytyrosol-rich composition from vegetation water. Patent No. WO0218310, 2002.
35. Fernandez-Bolanos, G. J.; Guillen, B. R.; Rodriguez, A. R.; Rodriguez, G. G.; Heredia, M. A.; Jimenez, A. A. Method for obtaining purified hydroxytyrosol from products and byproducts derived from the olive tree. Patent No. WO02064537, 2002.
36. Akasbi, M.; Shoeman, D. W.; Csallany, A. S. High-performance liquid chromatography of selected phenolic compounds in olive oils. J. Am. Oil Chem. Soc. 1993, 70(4), 367-370.
37. Feki, M.; Stambouli, M.; Pareau, D. H.; Ayedi, F. Study of the multicomponent system wet process phosphoric acid-methyl isobutyl ketone at 40 °C phase equilibria and extraction performances. Chem. Eng. J. 2001, 3932, 1-10.
38. Capasso, R. A review on the electron ionization and fast atom bombardment mass spectrometry of polyphenols naturally occurring in olive wastes and some of their synthetic derivatives. Phytochem. Anal. 1999, 10, 299-306.
39. Ryan, D.; Lawrence, H.; Prenzler, P. D.; Antolovich, M.; Robards, K. Recovery of phenolic compounds from Olea europaea. Anal. Chim. Acta 2001, 445, 67-77.
40. Tura, D.; Robards, K. Sample handling strategies for the determination of biophenols in food and plants. J. Chromatog. 2002, 975, 71-93.
41. Fernandez de Simon, B.; Cadahía, E.; Conde, E.; García-Vallejo, M. C. Low molecular weight phenolic compounds in Spanish oak woods. J. Agric. Food Chem. 1996, 44, 1507-1511.
42. Chien-ya, H.; Gow-Chin, Y. Extraction and identification of antioxidative components of Hsian-Tsao (Mesona procumbens Hemsl). Lebensm-Wiss. U.-Technol. 2001, 34, 306-311.
43. Romani, A.; Mulinacci N.; Pinelli, P.; Vincieri F. F.; Cimato, A. Polyphenolic content in five Tuscany cultivars of Olea europaea L. J. Agric. Food Chem. 1999, 47(3), 964-967.
44. Sheabar, F. Z.; Neeman, I. Separation and concentration of natural antioxidants from the rape of olives. J. Am. Oil Chem. Soc. 1988, 65, 990-993.
45. Capasso, R.; Evidente, A.; Scognamiglio, F. A simple thin layer chromatographic method to detect the main polyphenols occurring in olive oil vegetation waters. Phytochem. Anal. 1992, 3, 270-275.
46. Casa, R.; D'Annibale, A.; Pieruccetti, F.; Stazi, S. R.; Giovannozzi, S. G.; Lo Cascio, B. Reduction of the phenolic components in olive-mill wastewater by enzymatic treatment and its impact on durum wheat (Triticum durum Desf.) germinability. Chemosphere 2003, 50, 959-966.
47. Amiot, M. J.; Fleuriet, A.; Macheix, J. J. Importance and evolution of phenolic compounds in olive during growth and maturation. J. Agric. Food Chem. 1986, 34, 823-830.