Polar Phenolic Compounds

Olive Oil: Chemistry and Technology: Second Edition

Volumn , Issue , 2006, Pages 73-92

  Boskou, Dimitrios ^a   Tsimidou, Maria ^a   Blekas, Georgios ^a  

^a ARISTOTLE UNIVERSITY OF THESSALONIKI   (Greece)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICALS REMOVAL (WATER TREATMENT); DISEASES; OLIVE OIL; PHENOLS;

ALTERNATIVE SOURCE; BIOLOGICAL PROPERTIES; CARDIO-VASCULAR DISEASE; COMPLEX MIXTURE; DIETARY INTAKES; HYDROXYTYROSOL; METHANOL-WATER; PHENOLIC COMPOUNDS;

CHEMICAL COMPOUNDS;

EID: 84945129315     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1016/B978-1-893997-88-2.50009-2     Document Type: Chapter

References (95)

1. Agar I.T., Hess-Pierce B., Sourour M., et al. Quality of Fruit and Oil of Black-ripe Olives is Influenced by Cultivar and Storage Period. J. Agric. Food Chem. 1998, 46:3415-3421.
2. 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, 34:823-826.
3. Andrewes P., Busch J., De Joode T., et al. Sensory Properties of Virgin Olive Oil Polyphenols: Identification of Deacetoxy-ligstroside Aglycon as a Key Contributor to Pungency. J. Agric. Food Chem. 2003, 51:1415-1420.
4. Amiot M-J., Fleuriet A., Macheix J-J. Accumulation of Oleuropein Derivatives During Olive Maturation. Phytochemistry 1989, 28:67-69.
5. Angerosa F., Mostallino R., Basti C., et al. Influence of Malaxation Temperature and Time on the Quality of Virgin Olive Oils. Food Chem. 2001, 72:19-28.
6. Aparicio R., Luna G. Characterization of Monovarietal Virgin Olive Oils. Eur. J. Lipid Sci. Technol. 2002, 104:614-627.
7. Aparicio R., Roda L., Albi M., et al. Effect of Various Compounds on Virgin Olive Oil Stability Measured by Rancimat. J. Agric. Food Chem. 1999, 47:4150-4155.
8. Beauchamp G., Keast R., Morel D., et al. Ibuprofen-like Activity in Extra Virgin Olive Oil. Nature 2005, 437:45-46.
9. Béltran G., Aguilera M., Del Rio C., et al. Influence of Fruit Ripening Process on the Natural Antioxidant Content of Hojiblanca Virgin Olive Oils. Food Chem. 2005, 89:207-215.
10. Bianco A., Chiacchio M., Grassi D., et al. Phenolic Components of Olea europaea: Isolation of New Tyrosol and Hydroxytyrosol Derivatives. Food Chem. 2006, 95:562-565.
11. Bianco A., Coccioli F., Guiso M., et al. Presence in Olive Oil of a New Class of Phenolic Compounds: Hydroxyl-isochromans. Food Chem. 2001, 77:405-411.
12. Blekas G., Psomiadou E., Tsimidou M., et al. On the Importance of Total Polar Phenols to Monitor the Stability of Greek Virgin Olive Oil. Eur. J. Lipid Sci. Technol. 2002, 104:340-346.
13. Boskou D. Vegetable Oils in Food Technology 2002, 244-277. CRC Press, Oxford. F. Gunstone (Ed.).
14. Boskou D., Blekas G., Tsimidou M. Phenolic Compounds in Olive Oil and Olives. Current Topics in Nutraceutical Research 2005, 3:125-136.
15. Bouaziz M., Chamkha M., Sayadi S. Comparative Study on Phenolic Content and Antioxidant Activity During Maturation of the Olive Cultivar Chemlali from Tunisia. J Agric. Food Chem. 2004, 52:5476-5481.
16. Brenes M., Garcia P., Duran M.C., et al. Concentration of Phenolic Compounds Change in Storage of Brines of Ripe Olives. J. Food Sci. 1993, 58:347-350.
17. Brenes M., Garcia A., Garcia P., et al. Phenolic Compounds in Spanish Olive Oils. J. Agric. Food Chem. 1999, 47:3535-3540.
18. Brenes M., Hidalgo F., Garcia A., et al. Pinoresinol and 1-acetoxypinoresinol, Two New Phenolic Compounds Identified in Olive Oil. JAOCS 2000, 77:715-720.
19. Brenes M., Romero C., Garcia A., et al. Phenolic Compounds in Olive Oils Intended for Refining: Formation of 4-ethylphenol During Olive Paste Storage. J. Agric. Food Chem. 2004, 52:8177-8181.
20. Briante R., Patumi M., Limongelli S., et al. Changes in Phenolic and Enzymatic Activities Content During Fruit Ripening in Two Italian Cultivars of Olea europaea L. Plant Sci. 2002, 162:791-798.
21. Briante R., Febbraio F., Nucci R. Antioxidant Properties of Low Molecular Weight Phenols Present in the Mediterranean Diet. J. Agric. Food Chem. 2003, 51:6975-6981.
22. Caponio F., Allogio V., Gomes T. Phenolic Compounds of Virgin Olive Oil: Influence of Paste Preparation Techniques. Food Chem. 1999, 64:203-209.
23. Caponio F., Gomes T., Pasqualone A. Phenolic Compounds of Virgin Olive Oil: Influence of the Degree of Olive Ripeness on Organoleptic Characteristics and Shelf Life. Eur. Food Res. Technol. 2001, 212:329-333.
24. Carrasco-Pancorbo A., Cerretani L., Bendini A., et al. Analytical Determination of Polyphenols in Olive Oils. J. Separ. Sci. 2005, 28:837-858.
25. Carrasco-Pancorbo A., Cruces-Blanco C., Segura Carretero A., et al. Sensitive Determination of Phenolic Acids in Extra Virgin Olive Oil by Capillary Zone Electrophoresis. J. Agric. Food Chem. 2004, 52:6687-6693.
26. Catalano P., Caponio F. Machines for Olive Paste Preparation Producing Quality Virgin Olive Oil. Fett/Lipid 1996, 98:408-423.
27. Cert A., Alba J., Leon-Camacho M., et al. Effects of Talk Addition and Operating Mode on the Quality and Oxidative Stability of Virgin Olive Oils Obtained by Centrifugation. J. Agric. Food Chem. 1996, 44:3930-3934.
28. Christoforidou S., Dais P., Tseng L-H., et al. Separation and Identification of Phenolic Compounds in Olive Oil by Coupling High-performance Liquid Chromatography With Postcolumn Solid-phase Extraction to Nuclear Magnetic Resonance Spectroscopy (LC-SPE-NMR). J. Agric. Food Chem. 2005, 53:4667-4679.
29. Commission of the European Communities. Regulation No 1019/2002. Official Journal of the European Communities No L 155, (2002).
30. Cortesi N., Fiorino P., Ponzetti A. Olive Oil Composition in Relation to Cultivar and Extraction Methods. OLIVAE 2000, 81:36-39.
31. Crea R. HIDROX, Proprietary hydroxytyrosol, Creagri Inc. http://www.creagri.com/hidrox/5.
32. Deiana M., Aruoma O.I., Bianchi M.L., et al. Inhibition of Peroxynitrate Dependent DNA Base Modification and Tyrosine Nitration by the Extra Olive Oil-derived Antioxidant Hydroxytyrosol. Free Rad. Biol. Med. 1999, 26:762-769.
33. De la Puerta R., Martinez-Dominguez M., Ruiz-Gutierrez V., et al. Effects of Virgin Olive Oil Phenolics on Scavenging of Reactive Nitrogen Species and Upon Nitrergic Neurotransmission. Life Sciences 2001, 69:1213-1222.
34. Di Giovacchino L., Constantini N., Serraioco A., et al. Natural Antioxidants and Volatile Compounds of Virgin Olive Oils Obtained by Two or Three-phases Centrifugal Decanters. Eur. J. Lipid Sci. Technol. 2001, 103:279-285.
35. Esti M., Cinquanta L., LaNotte E. Phenolic Compounds in Different Olive Varieties. J. Agric. Food Chem. 1998, 46:32-35.
36. Fernandez-Bolanos J., Rodriguez G., Rodriguez R., et al. 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.
37. Fki I., Allouche N., Sayadi S. The Use of Polyphenolic Extract, Purified Hydroxytyrosol and 3,4-dihydroxyphenyl Acetic Acid From Olive Oil Mill Wastewater for the Stabilization of Refined Oils: a Potential Alternative to Synthetic Antioxidants. Food Chem. 2005, 93:197-204.
38. Fogliano V., Ritieni A., Monti S., et al. Antioxidant Activity of Virgin Olive Oil Phenolic Compounds in a Micellar System. J. Sci. Food Agric. 1999, 79:1803-1808.
39. Gallina-Toschi T., Cerretani L., Bendini A., et al. Oxidative Stability and Phenolic Content of Virgin Olive Oil: An Analytical Approach by Traditional and High Resolution Techniques. J. Sep. Sci. 2005, 28:850-870.
40. Garcia J., Seller S., Perez-Camino C. Influence of Fruit Ripening on Olive Oil Quality. J. Agric. Food Chem. 1996, 44:3516-3520.
41. Garcia A., Brenes M., Martinez F., et al. HPLC Evaluation of Phenols in Virgin Olive Oil During Extraction at Laboratory and Industrial Scale. JAOCS 2001, 78:625-629.
42. Garcia A., Brenes M., Romero C., et al. Study of Phenolic Compounds in Virgin Olive Oils of the Picual Variety. Eur. Food Res. Technol. 2002, 215:407-412.
43. Gibriel A., El-Rahman H., El-Razik Ali F., et al. Effect of Olive Oil Leaves Addition and Waste Water Recycling on the Productivity and Quality of Olive Oil Produced by Centrifugation. Euro Fed Lipid Intern Congress "Oils, Fats and Lipids in a changing world" 2004, Edinburgh, Abstracts 153.
44. Gimeno E., Castellote A., Lamuela-Ravéntos R., et al. The Effects of Harvest and Extraction Methods on the Antioxidant Content (phenolics, α-tocopherol and β-carotene) in Virgin Olive Oil. Food Chem. 2002, 78:207-211.
45. Gordon M., Paiva-Martins F., Almeida M. Antioxidant Activity of Hydroxytyrosol Acetate With That of Other Olive Oil Polyphenols. J. Agric. Food Chem. 2001, 49:2480-2485.
46. Gorinstein S., Martin-Belloso O., Katrich E., et al. Comparison of the Contents of the Main Biochemical Compounds and the Antioxidant Activity of Some Spanish Olive Oils as Determined by Four Different Radical Scavenging Tests. J. Nutr. Biochem. 2003, 14:154-159.
47. Grigoriadou D., Androulaki A., Tsimidou M. Levels of Phenolic Antioxidants in Virgin Olive Oil Purchased in Bulk. Ital. J. Food Sci. 2005, 17:195-202.
48. Guinda A., Tabera M., Rada M., et al. Supplementation of Vegetable Oils With Hydroxytyrosol From Olea europaea Leaves. Euro Fed Lipid Intern Congress "Oils, Fats and Lipids in a changing world" 2004, Edinburgh, Abstracts 319.
49. Gutfinger T. Polyphenols in Olive Oils. JAOCS 1981, 58:966-968.
50. Gutierrez F., Perdignero S., Gutierrez R., et al. Evaluation of the Bitter Taste in Virgin Olive Oil. JAOCS 1992, 69:394-395.
51. Gutierrez-Rosales F., T. Arnaud, Contribution of Polyphenols on the Oxidative Stability of Virgin Olive Oil. 24th World Congress ISF Berlin, Proceedings 61-62, (2001).
52. Gutierrez-Rosales F., Rios J., Gomez-Rey M. Main Polyphenols in the Bitter Taste of Virgin Olive Oil. Structural Confirmation by on line HPLC Electrospray Ionization Mass Spectrometry. J. Agric. Food Chem. 2003, 51:6021-6025.
53. Hrncirik K., Fritsche S. Comparability and Reliability of Different Techniques for the Determination of Phenolic Compounds in Virgin Olive Oil. Eur. J. Lipid Sci. Technol. 2004, 106:540-549.
54. Kachouri F., Hamdi M. Enhancement of Polyphenols in Olive Oil by Contact With Fermented Olive Oil Mill Waste Water by Lactobacillus plantarum. Process Biochem 2004, 39:841-845.
55. Koutsaftakis A., Kotsifaki F., Stefanoudaki E. Effect of Extraction System, Stage of Ripeness and Kneading Temperature on the Sterol Composition of Virgin Olive Oils. JAOCS 1999, 76:1477-1480.
56. Lavelli V. Comparison of the Antioxidant Activities of Extra Virgin Olive Oils. J. Agric. Food Chem. 2002, 50:7704-7706.
57. Litridou M., Linssen J., Schols H., et al. Phenolic Compounds of Virgin Olive Oils: Fractionation by Solid Phase Extraction and Antioxidant Activity Assessment. J Sci. Food Agric. 1997, 74:169-174.
58. Mateos R., Espartero J., Trujillo M., et al. Determination of Phenols, Flavones and Lignans in Virgin Olive Oil by Solid Phase Extraction and HPLC With Diode Array Ultraviolet Detection. J Agric. Food Chem. 2001, 49:2185-2192.
59. Mateos R., Cert A., Perez-Camino C., et al. Evaluation of Virgin Oil Bitterness by Quantification of Secoiridoid Derivatives. JAOCS 2004, 81:71-76.
60. Montedoro G., Servilli M., Baldioli M., et al. Simple and Hydrolysable Phenolic Compounds in Virgin Olive Oil. 1. Their Extraction, Separation and Quantitative and Semiquantitative Evaluation by HPLC. J. Agric. Food Chem. 1992, 40:1571-1576.
61. Monteleone E., Caporale G., Carlucchi A., et al. Optimization of Extra Virgin Olive Oil Quality. J Sci. Food Agric. 1998, 77:31-37.
62. Morales M., Tsimidou M. Handbook of Olive Oil 2002, 393-438. Aspen Publishers, Gaitesburg. J. Harwood, R. Aparicio (Eds.).
63. Morello J., Motilva M., Tovar M., et al. Changes in Commercial Virgin Olive Oil (cv. Arbequina) During Storage, With Special Emphasis on the Phenolic Fraction. Food Chem. 2004, 85:357-364.
64. Morello R., Romero M., Motilva M. Effect of the Maturation of the Olive Fruit on the Phenolic Fraction of Drupes and Oils From Arbequina, Farga, and Morrut Cultivars. J. Agric. Food Chem. 2004, 52:6002-6009.
65. Ninfali P., Aluigi G., Bacchiocca M., et al. Antioxidant Capacity of Extra Virgin Olive Oils. JAOCS 2001, 78:243-247.
66. Owen R., Mier W., Giacosa A., et al. Identification of Lignans as Major Components in the Phenolic Fraction of Olive Oil. Clinic. Chem. 2000, 46:976-988.
67. Paiva-Martins F., Correiab R., Gordon M. Effects of the Enrichment of Refined Oil With Leaf Phenolic Compounds. Euro Fed Lipid Intern Congress "Oils, Fats and Lipids in a changing world" 2004, Edinburgh, abstracts 280.
68. Pellegrini N., Serafini M., Colombi B., et al. Total Antioxidant Capacity of Plant Foods, Beverages and Oils Consumed in Italy Assessed by Three Different in vitro Assays. J. Nutr. 2003, 133:2812-2819.
69. Psomiadou E., Karakostas K., Blekas G., et al. Proposed Parameters for Monitoring Quality of Virgin Olive Oil (Koroneiki cv). Eur. J. Lipid Sci. Technol. 2003, 105:403-408.
70. Romero C., García P., Brenes M., et al. Phenolic Compounds in Natural Black Spanish Olive Varieties. Eur. Food Res. Technol. 2002, 215:489-496.
71. Romero C., Brenes M., García P., et al. Hydroxytyrosol 4-β-D-Glycoside, an Important Phenolic Compound in Olive Fruits and Derived Products. J. Agric. Food Chem. 2002, 50:3835-3839.
72. Rotondi A., Bendni A., Cerretani L., et al. Effect of Olive Ripening Degree on the Oxidative Stability and Organoleptic Properties of cv. Nostrana di Brisighella Extra Virgin Olive Oil. J. Agric. Food Chem. 2004, 52:3649-3654.
73. Rovellini P., Cortesi N. Determination of Phenolic Compounds in Different Cultivars During Olive Drupe Ripening by Liquid Chromatography-mass Spectrometry. OLIVÆ 2003, 95:32-38.
74. Ryan D., Antonovitch M., Prenzel P., et al. Biotransformation of Phenolic Compounds in Olea europaea L. Sintia Hortic. 2002, 92:147-176.
75. Saija A., Trombetta D., Tomaino A., et al. In vitro Evaluation of the Antioxidant Activity and Biomembrane Interaction of the Plant Phenols Oleuropein and Hydroxytyrosol. Intern. J. Pharmac. 1998, 166:123-133.
76. Salvador M., Aranda F., Fregapane G. Influence of Fruit Ripening on "Cornicabra" Virgin Olive Oil Quality. A Study of Four Successive Crop Seasons. Food Chem. 2001, 73:45-53.
77. Salvador M., Aranda F., Gomez-Alonso S., et al. Influence of Extraction System, Production Year and Area on Cornicabra Virgin Olive Oil: a Study of Five Crop Seasons. Food Chem. 2003, 80:359-366.
78. Servili M., Montedoro G. Contribution of Phenolic Compounds to Virgin Olive Oil Quality. Eur. J. Lipid Sci. Technol. 2002, 104:602-613.
79. Servili M., Sevaggini R., Taticchi A., et al. Air Exposure Time of Olive Pastes During the Extraction Process and Phenolic and Volatile Composition of Virgin Olive Oil. JAOCS 2003, 80:685-691.
80. Singleton V., Orthofer R., Lamuela-Raventos R. Methods in Enzymology 1999, Vol. 299:152-178. Academic Press, San Diego. L. Packer (Ed.).
81. Skaltsounis L., Process Development for an Integrated Olive Oil Mill Waste Management Recovering Natural Antioxidants and Producing Organic Fertilizer, Life ENV/GR/000671, (2004).
82. Skevin D., Rade D., Strucelj D., et al. The Influence of Variety and Harvest Time on the Bitterness and Phenolic Compounds of Olive Oil. Eur. J. Lipid Sci. Technol. 2003, 105:536-541.
83. Togna G., Togna A., Franconi M., et al. Olive Oil Isochromans Inhibit Human Platelet Reactivity. J Nutr. 2003, 133:2532-2536.
84. Tovar M., Motilva M., Romero M. Changes in the Phenolic Composition of Virgin Olive Oil From Young Trees (Olea europae L. cv. Arbequina) Grown Under Linear Irrigation Strategies. J. Agric. Food Chem. 2001, 41:5502-5508.
85. Tsimidou M., Papadopoulos G., Boskou D. Phenolic Compounds and Stability of Virgin Olive Oil. Food Chem. 1992, 45:141-144.
86. Tsimidou M. Polyphenols and Quality of Virgin Olive Oil in Retrospect. Ital. J. Food Sci. 1998, 10:99-116.
87. Tsimidou M. Analysis of Virgin Olive Oil Polyphenols. Seminars in Food Analysis, High-Performance Liquid Chromatography 1999, 4:13-29.
88. Tuck K., Hayball P., Stupans I. Structural Characterization of Metabolites of Hydroxytyrosol, the Principal Phenolic Component of Olive Oil. J Agric. Food Chem. 2002, 50:2404-2409.
89. Vinha A., Ferreres F., Silva B., et al. Phenolic Profiles of Portuguese Olive Fruits (Olea europaea L): Influences of Cultivar and Geographical Origin. Food Chem. 2005, 89:561-568.
90. Visioli F., Bellomo G., Galli C. Free Radical Scavenging Properties of Olive Oil Polyphenols. Biochem. Biophys. Res. Comm. 1998, 247:60-64.
91. Visioli F., Bellosta F., Galli C. Oleuropein, the Bitter Principle of Olives, Enhances Nitric Oxide Production by Mouse Macrophages. Life Sciences 1998, 62:541-546.
92. Visioli F., Galli C. The Effect of Minor Constituent of Olive Oil on Cardiovascular Disease: New Findings. Nutr. Rev. 1998, 56:142-146.
93. Visioli F., Romani A., Mulinacci N., et al. Antioxidant and Other Biological Activities of Olive Mill Waste Waters. J. Agric. Food Chem. 1999, 47:3397-3401.
94. Visioli F., Bogani P., Grande S., et al. Olive oil and Oxidative Stress. Grasas Aceites 2004, 55:66-75.
95. Zamora R., Alaiz M., Hidalgo F. Influence of Cultivar and Fruit Ripening on Olive (Olea europaea) Fruit Protein Content Composition and Antioxidant Activity. J. Agric. Food Chem. 2001, 49:4267-4270.