Wastes generated during the storage of extra virgin olive oil as a natural source of phenolic compounds

Journal of Agricultural and Food Chemistry

Volumn 59, Issue 21, 2011, Pages 11491-11500

  Lozano Sánchez, Jesus ^a,b   Giambanelli, Elisa ^c   Quirantes Piné, Rosa ^a,b   Cerretani, Lorenzo ^c   Bendini, Alessandra ^c   Segura Carretero, Antonio ^a,b   Fernández Gutiérrez, Alberto ^a,b  

^a UNIVERSITY OF GRANADA   (Spain)

^b Functional Food Research and Development Center   (Spain)

^c UNIVERSITY OF BOLOGNA   (Italy)

Author keywords

antioxidant natural source; byproduct; degradation pathways; MS MS fragmentation; olive oil; polyphenols; RRLC; storage

Indexed keywords

DEGRADATION PATHWAYS; MS/MS FRAGMENTATION; NATURAL SOURCES; OLIVE OIL; POLYPHENOLS; RRLC;

BYPRODUCTS; DEGRADATION; LIQUID CHROMATOGRAPHY; LIQUIDS; MASS SPECTROMETRY; ORGANIC ACIDS; PHENOLS; SOLVENT EXTRACTION; VEGETABLE OILS;

CHEMICAL COMPOUNDS;

ANTIOXIDANT; OLIVE OIL; PHENOL DERIVATIVE; VEGETABLE OIL;

ARTICLE; CHEMISTRY; INDUSTRIAL WASTE; ISOLATION AND PURIFICATION; OLIVE TREE; RECYCLING;

ANTIOXIDANTS; INDUSTRIAL WASTE; OLEA; PHENOLS; PLANT OILS; RECYCLING;

EID: 80455128178     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/jf202596q     Document Type: Article

References (38)

1. Bendini, A.; Cerretani, L.; Carrasco-Pancorbo, A.; Gomez-Caravaca, A. M.; Segura-Carretero, A.; Fernandez-Gutierrez, A.; Lercker, G. Phenolic molecules in virgin olive oils: a survey of their sensory properties, health effects, antioxidant activity and analytical methods. An overview of the last decade Molecules 2007, 12, 1679-1719
2. Impellizzeri, J.; Lin, J. M. A simple high-performance liquid chromatography method for the determination of throat-burning oleocanthal with probated antiinflammatory activity in extra virgin olive oils J. Agric. Food Chem. 2006, 54, 3204-3208
3. Suarez, M.; Macia, A.; Romero, M.; Motilva, M. Improved liquid chromatography tandem mass spectrometry method for the determination of phenolic compounds in virgin olive oil J. Chromatogr., A 2008, 1214, 90-99
4. Lozano-Sanchez, J.; Segura-Carretero, A.; Menendez, J. A.; Oliveras-Ferraros, C.; Cerretani, L.; Fernandez-Gutierrez, A. Prediction of extra virgin olive oil varieties through their phenolic profile. Potential cytotoxic activity against human breast cancer cells J. Agric. Food Chem. 2010, 58, 9942-9955
5. Servili, M.; Selvaggini, R.; Esposto, S.; Taticchi, A.; Montedoro, G.; Morozzi, G. Health and sensory properties of virgin olive oil hydrophilic phenols: agronomic and technological aspects of production that affect their occurrence in the oil J. Chromatogr., A 2004, 1054, 113-127
6. Angerosa, F.; Servili, M.; Selvaggini, R.; Taticchi, A.; Esposto, S.; Montedoro, G. Volatile compounds in virgin olive oil: occurrence and their relationship with the quality J. Chromatogr., A 2004, 1054, 17-31
7. Chiacchierini, E.; Mele, G.; Restuccia, D.; Vinci, G. Impact evaluation of innovative and sustainable extraction technologies on olive oil quality Trends Food Sci. Technol. 2007, 18, 299-305
8. Di Lecce, G.; Bendini, A.; Cerretani, L.; Bonoli-Carbognin, M.; Lercker, G. Shelf stability of extra virgin olive oil under domestic conditions Ind. Aliment. Italy 2006, 461, 873-880
9. Lozano-Sanchez, J.; Cerretani, L.; Bendini, A.; Segura-Carretero, A.; Fernandez-Gutierrez, A. Filtration process of extra virgin olive oil: effect on minor components, oxidative stability and sensorial and physicochemical characteristics Trends Food Sci. Technol. 2010, 21, 201-211
10. Badimon, L.; Vilahur, G.; Padro, T. Nutraceuticals and atherosclerosis: human trials Cardiovasc. Ther. 2010, 28, 202-215
11. Poudyal, H.; Campbell, F.; Brown, L. Olive leaf extract attenuates cardiac, hepatic, and metabolic changes in high carbohydrate-, high fat-fed rats J. Nutr. 2010, 140, 946-953
12. Corona, G.; Deiana, M.; Incani, A.; Vauzour, D.; Dessì, M. A.; Spencer, J. P. E. Hydroxytyrosol inhibits the proliferation of human colon adenocarcinoma cells through inhibition of ERK1/2 and cyclin D1 Mol. Nutr. Food Res. 2009, 53, 897-903
13. Suarez, M.; Romero, M.; Ramo, T.; Macia, A.; Motilva, M. Methods for preparing phenolic extracts from olive cake for potential application as food antioxidants J. Agric. Food Chem. 2009, 57, 1463-1472
14. Agalias, A.; Magiatis, P.; Skaltsounis, A.; Mikros, E.; Tsarbopoulos, A.; Gikas, E.; Spanos, I.; Manios, T. A new process for the management of olive oil mill waste water and recovery of natural antioxidants J. Agric. Food Chem. 2007, 55, 2671-2676
15. Lujan, R. J.; Capote, F. P.; Marinas, A.; de Castro, M. D. L. Liquid chromatography/triple quadrupole tandem mass spectrometry with multiple reaction monitoring for optimal selection of transitions to evaluate nutraceuticals from olive-tree materials Rapid Commun. Mass Spectrom. 2008, 22, 855-864
16. Fu, S.; Arraez-Roman, D.; Segura-Carretero, A.; Menendez, J. A.; Menendez-Gutierrez, M. P.; Micol, V.; Fernandez-Gutierrez, A. Qualitative screening of phenolic compounds in olive leaf extracts by hyphenated liquid chromatography and preliminary evaluation of cytotoxic activity against human breast cancer cells Anal. Bioanal. Chem. 2010, 397, 643-654
17. Paiva-Martins, F.; Pinto, M. Isolation and characterization of a new hydroxytyrosol derivative from olive (Olea europaea) leaves J. Agric. Food Chem. 2008, 56, 5582-5588
18. Lozano-Sanchez, J.; Segura-Carretero, A.; Fernandez-Gutierrez, A. Characterisation of the phenolic compounds retained in different organic and inorganic filter aids used for filtration of extra virgin olive oil Food Chem. 2011, 124, 1146-1150
19. De Marco, E.; Savarese, M.; Paduano, A.; Sacchi, R. Characterization and fractionation of phenolic compounds extracted from olive oil mill wastewaters Food Chem. 2007, 104, 858-867
20. Fu, S.; Arraez-Roman, D.; Menendez, J. A.; Segura-Carretero, A.; Fernandez-Gutierrez, A. Characterization of isomers of oleuropein aglycon in olive oils by rapid-resolution liquid chromatography coupled to electrospray time-of-flight and ion trap tandem mass spectrometry Rapid Commun. Mass Spectrom. 2009, 23, 51-59
21. Obied, H. K.; Allen, M. S.; Bedgood, D. R., Jr.; Prenzler, P. D.; Robards, K. Investigation of Australian olive mill waste for recovery of biophenols J. Agric. Food Chem. 2005, 53, 9911-9920
22. De La Torre-Carbot, K.; Jauregui, O.; Gimeno, E.; Castellote, A. I.; Lamuela-Raventos, R. M.; Lopez-Sabater, M. C. Characterization and quantification of phenolic compounds in olive oils by solid-phase extraction, HPLC-DAD, and HPLC-MS/MS J. Agric. Food Chem. 2005, 53, 4331-4340
23. Bazoti, F. N.; Gikas, E.; Skaltsounis, A. L.; Tsarbopoulos, A. Development of a liquid chromatography-electrospray ionization tandem mass spectrometry (LC-ESI MS/MS) method for the quantification of bioactive substances present in olive oil mill wastewaters Anal. Chim. Acta 2006, 573-574, 258-266
24. Lerma-Garcia, M. J.; Simo-Alfonso, E. F.; Chiavaro, E.; Bendini, A.; Lercker, G.; Cerretani, L. Study of chemical changes produced in virgin olive oils with different phenolic contents during an accelerated storage treatment J. Agric. Food Chem. 2009, 57, 7834-7840
25. Brenes, M.; Garcia, A.; Garcia, P.; Garrido, A. Acid hydrolysis of secoiridoid aglycons during storage of virgin olive oil J. Agric. Food Chem. 2001, 49, 5609-5614
26. Morello, J. R.; Motilva, M. J.; Tovar, M. J.; Romero, M. P. Changes in commercial virgin olive oil (cv Arbequina) during storage, with special emphasis on the phenolic fraction Food Chem. 2004, 85, 357-364
27. García-Villalba, R.; Carrasco-Pancorbo, A.; Oliveras-Ferraros, C.; Vázquez-Martín, A.; Menéndez, J. A.; Segura-Carretero, A.; Fernández-Gutiérrez, A. Characterization and quantification of phenolic compounds of extra-virgin olive oils with anticancer properties by a rapid and resolutive LC-ESI-TOF MS method J. Pharm. Biomed. Anal. 2010, 51, 416-429
28. Owen, R. W.; Mier, W.; Giacosa, A.; Hull, W. E.; Spiegelhalder, B.; Bartsch, H. Phenolic compounds and squalene in olive oils: The concentration and antioxidant potential of total phenols, simple phenols, secoiridoids, lignans and squalene Food Chem. Toxicol. 2000, 38, 647-659
29. Tovar, M. J.; Motilva, M. J.; Romero, M. P. Changes in the phenolic 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
30. Tripoli, E.; Giammanco, M.; Tabacchi, G.; Di Majo, D.; Giammanco, S.; La Guardia, M. The phenolic compounds of olive oil: structure, biological activity and beneficial effects on human health Nutr. Res. Rev. 2005, 18, 98-112
31. Ghidouche, S.; Es-Safi, N.; Ducrot, P. Mechanistic study on the enzymatic oxidation of flavonols Tetrahedron Lett. 2008, 49, 619-623
32. Cermola, F.; DellaGreca, N.; Iesce, M. R.; Montella, S.; Pollio, A.; Temussi, F. A mild photochemical approach to the degradation of phenols from olive oil mill wastewater Chemosphere 2004, 55, 1035-1041
33. Antolovich, M.; Bedgood, D. R.; Bishop, A. G.; Jardine, D.; Prenzler, P. D.; Robards, K. LC-MS investigation of oxidation products of phenolic antioxidants J. Agric. Food Chem. 2004, 52, 962-971
34. Gómez-Alonso, S.; Mancebo-Campos, V.; Salvador, M. D.; Fregapane, G. Evolution of major and minor components and oxidation indices of virgin olive oil during 21 months storage at room temperature Food Chem. 2007, 100, 36-42
35. Garcia-Villalba, R.; Carrasco-Pancorbo, A.; Oliveras-Ferraros, C.; Vazquez-Martin, A.; Menendez, J. A.; Segura-Carretero, A.; Fernandez-Gutierrez, A. Characterization and quantification of phenolic compounds of extra-virgin olive oils with anticancer properties by a rapid and resolutive LC-ESI-TOF MS method. J. Pharm. Biomed. Anal. 51, 416-429.
36. 2 induced lipid peroxidation in renal tubular epithelial cells Food Chem. Toxicol. 2008, 46, 2984-2990
37. Corona, G.; Deiana, M.; Incani, A.; Vauzour, D.; Dessì, M. A.; Spencer, J. P. E. Hydroxytyrosol inhibits the proliferation of human colon adenocarcinoma cells through inhibition of ERK1/2 and cyclin D1 Mol. Nutr. Food Res. 2009, 53, 897-903
38. Incani, A.; Deiana, M.; Corona, G.; Vafeiadou, K.; Vauzour, D.; Dessì, M. A.; Spencer, J. P. E. Involvement of ERK, Akt and JNK signalling in H2O2-induced cell injury and protection by hydroxytyrosol and its metabolite homovanillic alcohol Mol. Nutr. Food Res. 2010, 54, 788-796