Contribution of phenolic compounds to virgin olive oil quality

European Journal of Lipid Science and Technology

Volumn 104, Issue 9-10, 2002, Pages 602-613

  Servili, Maurizio ^a   Montedoro, GianFrancesco ^a  

^a UNIVERSITY OF PERUGIA   (Italy)

Author keywords

(3,4 dihydroxyphenyl)ethanol; Antioxidants; Mechanical extraction process; Phenols; Secoiridoids; Virgin olive oil

Indexed keywords

ANTIOXIDANT; OLIVE OIL; PHENOL DERIVATIVE;

AGRONOMY; CHEMICAL COMPOSITION; CHEMICAL STRUCTURE; CULTIVAR; EXTRACTION; FOOD QUALITY; NONHUMAN; PREVALENCE; REVIEW;

EID: 0036424908     PISSN: 14387697     EISSN: None     Source Type: Journal    
DOI: 10.1002/1438-9312(200210)104:9/10<602::AID-EJLT602>3.0.CO;2-X     Document Type: Review

References (86)

1. D. Boskou: Olive Oil Chemistry and Technology. AOCS Press, Champaign, IL (USA) 1996, pp. 52-83.
2. F. Shahidi: Natural Antioxidants Chemistry, Health Effect and Applications. AOCS Press, Champaign, IL (USA) 1996, pp. 97-149.
3. C. Cantarelli: Sui polifenoli presenti nella drupa e nell'olio di oliva. Riv. Ital. Sostanze Grasse 38 (1961) 69-72.
4. GF. Montedoro, C. Cantarelli: Indagine sulle sostanze fenoliche presenti nell'olio di oliva. Riv. Ital. Sost. Grasse 46 (1969) 115-124.
5. P. Capella, E. Fedeli, G. Bonaga, G. Lerker: Manuale degli Oli e dei Grassi. Tecniche Nuove, Milano (Italy) 1997.
6. M. Servili, M. Baldioli, F. Mariotti, GF. Montedoro: Phenolic composition of olive fruit and virgin olive oil: Distribution in the constitutive pads of fruit and evolution during oil mechanical extraction process. Acta Horticulturae 474 (1999) 609-619.
7. GF. Montedoro, M. Servili, M. Baldioli, R. Selvaggini, A.L. Begliomini, A. Taticchi: Relationships between phenolic composition of olive fruit and olive oil: The importance of the endogenous enzymes. Acta Horticulturae (2001) in press.
8. M. J. Garrido Fernández Díez, M. R. Adamos: Table Olives. Chapman & Hall, London (UK) 1997, pp. 67-109.
9. A. Vasquez Roncero, E. Graciani Costante, R. Maestro Durán: Componentes fenólicos de la aceituna. Polifenoles de la pulpa. Gracas y Aceites 25 (1974) 269-279.
10. R. Maestro Durán, A. Vasquez Roncero: Colorantes antocianicos de las aceitunas manzanillas maduras. Gracas y Aceites 27 (1976) 237-245.
11. Mazza, E. Miniati: Anthocyanins in Fruits, Vegetables and Grains. CRC Press, Boca Raton, Florida (USA) 1993, pp. 64-67.
12. N. L. Marekow: Polyphenols Research in Bulgaria. Bull Liaison Groupe Polyphenols, 1984, pp. 12-31.
13. P. Gariboldi, G. Jommi, L. Verotta: Secoiridoids from Olea europaea. Phytochemistry 25 (1986) 865-869.
14. E. Bourquelot, J. C. R. Vintilesco: Sur l'oleuropein, nouveau principe de nature glucosidique retré de l'olivier (Olea europaea L.). Compt. Rend. Hebd. Acad. Sci., Paris (France) 147 (1908) 533-535.
15. L. Panizzi, M.L. Scarpati, G. Oriente: Chemical structure of oleuropein, bitter glucoside of olive with hypotensive activity. Gazz. Chim. Ital. 90 (1960) 1449-1485.
16. E. Ragazzi, G. Veronese, A. Guitto: The demethyloleuropein, a new glucoside extracted from ripe olives. Ann. Chim. 63 (1973) 13-20.
17. I. Kubo, A. Matsumoto: Molluscicides from olives Olea europaea and their efficient isolation by countercurrent chromatography. J. Agric. Food Chem. 32 (1984) 687-688.
18. C. Andary, R. Wylde, C. Laffite, G. Privat, F. Winternitz: Structure of verbascoside and orobancoside, caffeic acid sugar esters from Orobanche rapum-genistae. Phytochemistry 21 (1982) 1123-1127.
19. M. Servili, M. Baldioli, R. Selvaggini, E. Miniati, A. Macchioni, GF. Montedoro: 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. 76 (1999) 873-882.
20. M. Servili, M. Baldioli, R. Selvaggini, A. Macchioni, GF. Montedoro: Phenolic compounds of olive fruit: One- and two-dimensional Nuclear Magnetic Resonance characterization of nüzhenide and its distribution in the constitutive parts of fruit. J. Agric. Food Chem. 47 (1999) 12-18.
21. GF. Montedoro: I costituenti fenolici presenti negli oil vergini di oliva. Nota 1: Identificazione di alcuni acidi fenolici e loro potere antiossidante. S.T.A. 3 (1972) 177-186.
22. A. Vasquez Roncero: Les polyphenols de l'huile d'olive et leur influence sur les characteristiques de l'huile. Rev. Fr. Corps Gras 25 (1978) 21-26.
23. M. Solinas, A. Cichelli: Sulla deteminazione delle sostanze fenoliche dell'olio di oliva. Riv. Ital. Sostanze Grasse 58 (1981) 159-164.
24. N. Cortesi, E. Fedeli: Polar components of virgin olive oil. Note 1. Riv. Ital. Sostanze Grasse 60 (1983) 341-351.
25. M. Solinas: Analisi HRGC delle sostanze fenoliche di oli vergini di oliva in relazione al grado di maturazione ed alla varietà delle olive. Riv. Ital. Sostanze Grasse 64 (1987) 255-262.
26. GF. Montedoro, M. Servili, M. Baldioli, E. Miniati: Simple and hydrolyzable compounds in virgin olive oil. 1. Their extraction, separation and quantitative and semiquantitative evaluation by HPLC. J Agric. Food Chem. 40 (1992) 1571-1576.
27. M. Tsimidou, M. Lytridou, D. Boskou, A. Paooa-Lousi, F. Kotsifaki, C. Petrakis: On the determination of minor phenolic acids of virgin olive oil by RP-HPLC. Grasas y Aceites 47 (1996) 151-157.
28. S. Mannino, M.S. Cosio, M. Bertuccioli: High performance liquid chromatography of phenolic compounds in virgin olive oil using amperometryc detector. Ital. J. Food Sci. 4 (1993) 363-370.
29. GF. Montedoro, M. Servili, M. Baldioli, E. Miniati: Simple and hydrolyzable compounds in virgin olive oil. Note 2: Initial characterization of the hydrolizable fraction. J Agric. Food Chem. 40 (1992) 1577-1580.
30. GF. Montedoro, M. Servili, M. Baldioli, R. Selvaggini, E. Miniati, A. Macchioni: Simple and hydrolyzable compounds in virgin olive oil. Note 3: Spectroscopic characterization of the secoiridoids derivatives. J. Agric. Food Chem. 41 (1993) 2228-2234.
31. F. Angerosa, N. D'Alessandro, F. Corana, G. Mellerio: Characterization of phenolic and secoiridoid aglycons present in virgin olive oil by gas chromatography-chemical ionization mass spectrometry. J. Agric. Food Chem. 43 (1995) 1802-1807.
32. F. Angerosa, N. D'Alessandro, P. Konstantinou, L. Di Giacinto: GC-MS evaluation of phenolic compounds in virgin olive oil. J. Chromatogr. A 736 (1996) 195-203.
33. R. W. Owen, W. Mier, A. Giacosa, W. E. Hull, B. Spiegelhalder, H. Bartsch: Phenolic compounds and squalene in olive oils: The concentration and antioxidant potential of total phenols, simple phenols, secoiridoids, lignans and squalene. Food Chem. Toxicol. 38 (2000) 647-659.
34. E. Perri, A. Raffaelli, G. Sindona: Quantification of oleuropein in virgin olive oil by ionspray mass spectrometry-selected reaction monitoring. J. Agric. Food Chem. 47 (1999) 4156-4160.
35. A. D. Bianco, L. Muzzalupo, G. Romeo, M. L. Scarpati, A. Soriero, N. Uccella: Microcomponents of olive oil. Note 3: Glucosides of 2(3,4-dihydroxy-phenyl)ethanol. Food Chem. 63 (1998) 461-464.
36. P. Rovelli, N. Cortesi, E. Fedeli: Analysis of flavonoids from Olea europaea by HPLC-UV and HPLC-electrospray-MS. Riv. Ital. Sostanze Grasse 74 (1997) 273-279.
37. R. W. Owen, W. Mier, A. Giacosa, W. E. Hull, B. Spiegelhalder, H. Bartsch: Identification of lignans as major components in the phenolic fraction of olive oil. Clin. Chem. 46 (2000) 976-988.
38. M. Baldioli, M. Servili, G. Perretti, GF. Montedoro: Antioxidant activity of tocopherols and phenolic compounds of virgin olive oil. J. Am. Oil Chem. Soc. 73 (1996) 1589-1593.
39. M. H. Gordon: The mechanism of antioxidant action in vitro. In: Food Antioxidants. Ed. B. J. F. Hudson, Elsevier Applied Science, London (UK) 1990, pp. 1-18.
40. H. Chimi, J. Cillard, P. Cillard, M. Rahmani: Peroxyl and hydroxyl radical scavengig activity of some natural phenolic antioxidants. Ibid 68 (1991) 307-311.
41. R. Gutierrez Gonzales-Quijano, C. Janer del Valle, M. L. Janer del Valle, F. Gutierrez Rosales, A. Vasquez Roncero: Relationships between polyphenols content and the quality and stability of virgin olive oil. Grasas y Aceites 28 (1977) 101-106.
42. H. Chimi, A. Sadik, B. Le Tutour, M. Rahmani: Contribution à l'étude comparative des pouvoirs antioxydants dans l'huile d'olive di tyrosol e de l'hydroxytyrosol, de l'acide caffeique, de l'oleuropéine et du BHT. Rev. Fr. Corps Gras 35 (1988) 339-344.
43. G. Papadopoulos, D. Boskou: Antioxidant effect of natural phenols of olive oil. J. Am. Oil Chem. Soc. 68 (1991) 669-671.
44. P. Ninfali, G. Aluigi, M. Bacchiocca, M. Magnani: Antioxidant capacity of extra-virgin olive oil. J. Am. Oil Chem. Soc. 78 (2001) 243-247.
45. M. Bacchiocca, G. Aluigi, M. Servili, A. L. Begliomini, GF. Montedoro, P. Ninfali: Validation of the Orac method in the prevision of the stability of extravirgin olive oil. Riv. Ital. Sostanze Grasse 78 (2001) 151-156.
46. M. Servili, GF. Montedoro: Recupero dei polifenoli delle acque di vegetazione delle olive e valutazione del loro potere antiossidante. Industrie Alimentari 28 (1989) 14-19.
47. F. Evangelisti, P. Zunin, E. Tiscornia, R. Petacchi, G. Drava, S. Lanteri: Stability to oxidation of virgin olive oils as related to olive conditions: Study of polar compounds by chemometric methods. J. Am. Oil Chem. Soc. 74 (1997) 1017-1023.
48. R. Briante, F. La Cara, P. Tunziello, F. Febraio, R. Nucci: Antioxidant activity of the main bioactive derivatives from oleuropein hydrolysis by hyperthermophylic β-glucosidase. J. Agric. Food Chem. 49 (2001) 3198-3203.
49. Petroni, M. Blasevich, M. Salami, N. Papini, GF. Montedoro, C. Galli: Inhibition of platelet aggregation and eicosanoid production by phenolic component of olive oil. Thromb. Res. 78 (1995) 151-160.
50. F. Visioli, G. Bellomo, GF. Montedoro, C. Galli: Low density lipoprotein oxidation is inhibited in vitro by olive oil constituents. Atherosclerosis 117 (1995) 25-32.
51. C. Manna, V. Galletti, P. Cucciolla, GF. Montedoro, V. Zappia: Olive oil hydroxytirosol protects human erythrocytes against oxidative damages. J. Nutr. Biochem. 10 (1999) 159-165.
52. 1 cell cycle arrest and apoptosis. Submitted to: European Journal of Cancer Prevention (2001).
53. F. Gutiérrez Rosales, S. Perdiguero, R. Gutiérrez, J. M. Olias: Evaluation of the bitter taste in virgin olive oil. J. Am. Oil Chem. Soc. 69 (1992) 394-395.
54. GF. Montedoro, M. Baldioli, M. Servili: I composti fenolici dell'olio di oliva e la loro importanza sensoriale, nutrizionale e merceologica. Giornale Ital. di Nutriz. Clin. e Prev. 1 (1992) 19-32.
55. M. Tsimidou: Polyphenols and quality of virgin olive oil in retrospect. Ital. J. Food Sci. 10 (1998) 99-116.
56. R. G. Gonzalez-Quijano, C. Janer del Valle, M. L. Janet del Valle, G. F. Rosales: Relacion entre los polifenoles y la calidad y stabilidad del aceite de oliva virgen. Grasas y Aceites 28 (1977) 101-109.
57. E. Graciani Costante, A. Vasquez Roncero: Estudio de los componentes polares del aceite de oliva por cromatografia liquida de alta eficacia (HPLC). III Aplicacion a diversos tipos de aceites virgenes. Grasas y Aceites 32 (1981) 365-370.
58. N. Uccella: The olive biophenols: Hedonic-sensory descriptors of evoo and wotos in the Mediterranean aliment culture. In Food Flavours and Chemistry: Advances of the New Millennium. Eds. A. H. Spanier, F. Shahidi, T.H. Parliment, C. J. Mussinan, C. T. Ho, E. Tratras Contis, The Royal Society of Chemistry Publishers, Cambridge (UK) 2001, pp. 253-265.
59. GF. Montedoro, L. Garofolo, M. Bertuccioli, G. Pannelli: Influence of the cultivars and pedoclimatic conditions on the virgin olive oil quality. Proceedings of 6th International Flavor Conference, Rethymnon, Crete, Greece, 5-7 July 1989, Ed. G. Charalambous, Elsevier Science Publishers B.V., Amsterdam (The Netherlands) 1989, pp. 881-891
60. G. Pannelli, M. Servili, F. Famiani, GF. Montedoro: Agro-climatic factors and characteristics of the composition of virgin olive oils. Acta Horticulturae 286 (1990) 477-480.
61. M. Uceda, M. Hermoso, A. García-Ortiz, A. Jmenez, G. Beltrán: Intraspecific variation of oil contents and the characteristics of oils in olive cultivars. Acta Horticulturae 474 (1999) 659-652.
62. M. Brenes, A. García, P. García, J. J. Rios, A. Garrido: Phenolic compounds in Spanish oils. J. Agric. Food Chem. 47 (1999) 3535-3540.
63. M. J. Amiot, A. Fleuriet, J. J. Macheix: Importance and evolution of phenolic compounds in olive during growth and maturation. J. Agric. Food Chem. 34 (1986) 823-826.
64. M. J. Amiot, A. Fleuriet, J. J. Macheix: Accumulation of oleuropein derivatives during olive maturation. Phytochemistry 28 (1989) 67-69.
65. G. Pannelli, M. Servili, R. Selvaggini, M. Baldioli, GF. Montedoro: Effect of agronomic and seasonal factors olive (Olea europaea L.) production and on the qualitative characteristics of the oil. Acta Horticolturae 356 (1994) 239-244.
66. M. J. Motilva, M. P. Romero, S. Alegre, J. Girona: Effect of regulated deficit irrigation in olive oil production and quality. Acta Horticulturae 474 (1999) 377-380.
67. A. S. Ismail, G. Stavroulakis, J. Metzidakis: Effect of irrigation on the quality characteristics of organic olive oil. Acta Horticulturae 474 (1999) 687-690.
68. M. Servili, M. Baldioli, GF. Montedoro: Phenolic composition of virgin olive oil in relationship to some chemical and physical aspects of malaxation. Acta Horticolturae. 356 (1994) 331-336.
69. R. Lo Scalzo, M. L. Scarpati: A new secoiridoid from olive waste waters. J. Nat. Prod. 56 (1993) 621-623.
70. A. D. Bianco, A. Piperno, G. Romeo, N. Uccella: NMR experiments of oleuropein biomimetic hydrolysis. J. Agric. Food Chem. 47 (1999) 3665-3668.
71. V. Sciancalepore: Enzymatic browning in five olive varieties. J. Food Sci. 50 (1985) 1194-1195.
72. M. Servili, M. Baldioli, R. Selvaggini, F. Mariotti, E. Federici, GF. Montedoro: Effect of malaxation under N2 flush on phenolic and volatile compounds of virgin olive oil. 13th International Symposium on Plant Lipids, Siviglia (Spain) 1998, pp. 307-310.
73. M. Servili, M. Baldioli, A. L. Begliomini, R. Selvaggini, GF. Montedoro: The Phenolic and Volatile Compounds of Virgin Olive Oil: Relationships with the Endogenous Oxidoreductases During the Mechanical Oil Extraction Process. Flavour and Fragrance Chemistry, Eds. V. Lanzotti and O. Taglialatela-Scafati, Kluwer Academic Publishers, Dordrecht (The Netherlands) 2000, pp. 163-173.
74. GF. Montedoro, M. Servili: Tradizione ed innovazioni tecnologiche nell'estrazione degli olii extravergini di oliva. Proceeding of the International Congress "Olive Oil Quality", Firenze (Italy) 1-3 December 1992, pp. 97-108.
75. P. Amirante, P. Catalano, R. Amirante, G. Montel, G. Dugo, V. LoTurco, L. Baccioni, D. Fazio, A. Mattei, F. Marotta: Estrazione da paste denocciolate. Olivo & Olio. 4, 3 (2001) 48-55.
76. GF. Montedoro, M. Baldioli, M. Servili: Estrazione dell'olio vergine da paste denocciolate. Olivo & Olio. 4, 11 (2001), 28-32.
77. C. M. Spencer, Y. Cai, M. Russel, S. H. Gaffney, P. Goulding, D. Magnolato, T. H. Lilley, E. Haslam: Polyphenol complexation: Some thoughts and observation. Phytochemistry 27 (1988) 2397-2409.
78. A. Ranalli, G. De Mattia: Characterization of olive oil production with a new enzyme processing aid. J. Am. Oil Chem. Soc. 74 (1997) 1105-1113.
79. V. Siniscalco, GF. Montedoro: Estrazione meccanica dell'olio di oliva mediante l'impiego di coadiuvanti tecnologici. Nota 1: Drenanti ed enzimi. Riv. Ital. Sostanze Grasse 11 (1988) 675-678
80. E. Vierhuis, M. Servili, M. Baldioli, H. A. Schols, A. G. J. Voragen, GF. Montedoro: Effect of enzyme treatment during mechanical extraction of olive oil on phenolic compounds and polysaccharides. J. Agric. Food Chem. 49 (2001) 1218-1223.
81. L. Di Giovacchino, M. Solinas, M. Miccoli: Effect of extraction systems on the quality of virgin olive oil. J. Am. Oil Chem. Soc. 71 (1994) 1189-1194.
82. A. Garcia, M. Brenes, F. Martinez, J. Alba, P. Garcia, A. Garrido: High-performance liquid chromatography evaluation of phenols in virgin olive oil during extraction at laboratory and industrial scale. J. Am. Oil Chem. Soc. 78 (2001) 625-629
83. L. Di Giovacchino, N. Costantini, A. Serraiocco, G. Surricchio, C. Basti: Natural antioxidants and volatile compounds of virgin olive oils obtained by two or three-phases centrifugal decanters. Eur. J. Lipid Sci. Technol. 103 (2001) 279-285.
84. A. Ranalli, F. Angerosa: Integral centrifuges for olive oil extraction. The qualitative characteristics of products. J. Am. Oil Chem. Soc. 73 (1996) 417-421
85. E. Stefanoudakii, A. K. outsaftakis, F. Kotsifaki, F. Angerosa, M. DiGirolamo: Quality characteristics of olive oils dual-phases, three-phases decanters and laboratory mill. Acta Horticulturae 474 (1999) 705-708.
86. G. De Stefano, P. Piaquadio, M. Servili, L. Di Giovacchino, V. Sciancalepore: Effect of the extraction systems on the phenolic composition of virgin olive oils. Fett/Lipid 101 (1999) 328-332.