Analytical methodologies: Phenolic compounds related to olive oil taste issues

Handbook of Olive Oil: Analysis and Properties

Volumn , Issue , 2013, Pages 311-333

  Tsimidou, Maria Z ^a  

^a ARISTOTLE UNIVERSITY OF THESSALONIKI   (Greece)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84956819709     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1007/978-1-4614-7777-8_9     Document Type: Chapter

References (87)

1. Amiot MJ, Fleuriet A, Macheix JJ (1986) Importance and evolution of phenolic compounds in olive during growth and maturation. J Agric Food Chem 34:823-826
2. Amiot MJ, Fleuriet A, Macheix JJ (1989) Accumulation of oleuropein derivatives during olive maturation. Phytochemistry 28:67-69
3. Andrewes P, Busch JL, De Joode T, Groenewegen A, Alexandre H (2003) Sensory properties of virgin olive oil polyphenols: Identification of deacetoxy-ligstroside aglycon as a key contributor to pungency. J Agric Food Chem 51:1415-1420
4. Angerosa F, D'Alessandro N, Konstantinou P, Di Giacinto L (1995) GC-MS evaluation of phenolic compounds in virgin olive oil. J Agric Food Chem 43:1802-1807
5. Angerosa F, Mostallino R, Basti C (2000) Virgin olive oil odor notes: their relationships with volatile compounds from the lipooxygenase pathway and secoiridoid compounds. Food Chem 68:283-287
6. Armaforte E, Mancebo-Campos V, Bendini A, Salvador MD, Fregapane G et al (2007) Retention effects of oxidized polyphenols during analytical extraction of phenolic compounds of virgin olive oil. J Sep Sci 30:2401-2406
7. Beauchamp GJ, Keast RSJ, Morel D, Lin J, Pika J et al (2005) Ibuprofen-like activity in extra-virgin olive oil. Nature 437:45-46
8. Bendini A, Bonoli M, Cerretani L, Biguzzi B, Gallina-Toschi T et al (2003) Liquid-liquid and solid-phase extraction from phenols from virgin olive oil and their separation by chromatographic and electrophoretic methods. J Chromatogr A 98:425-433
9. Bendini A, Cerretani L, Carrasco-Pancorbo A, Gómez-Caravaca AM, Segura-Carretero A, Fernández-Gutiérrez A, Lercker G (2007) 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 12:1679-1719
10. Bianchi G (2003) Lipids and phenols in table olives. Eur J Lipid Sci Technol 105:229-242
11. Bianco A, Coccioli F, Guiso M, Marra C (2001) The occurence in olive oil of a new class of a new class of phenolic compounds: hydroxy-isochromans. Food Chem 77:405-411
12. Blekas G, Psomiadou E, Tsimidou M, Boskou D (2002) On the importance of total polar phenols to monitor the stability of Greek virgin olive oil. Eur J Lipid Sci Technol 104:340-346
13. Bonoli M, Montanucci M, Gallina-Toschi T, Lercker G (2003) Fast separation and determination of tyrosol, hydroxytyrosol and other phenolic compounds in extra-virgin olive oil by capillary zone electrophoresis with ultraviolet-diode array detection. J Chromatogr A 1011:163-172
14. Boskou D, Tsimidou MZ, Blekas G (2006) Polar phenolic compounds. In: Boskou D (ed) Olive oil: chemistry and technology, 2nd edn. AOCS Press, Champaign, pp 73-92
15. Brenes M, García A, García P, Garrido A (2000) Rapid and complete extraction of phenols from olive oil and determination by means of a coulometric electrode array system. J Agric Food Chem 48:5178-5183
16. Brenes M, García A, Ríos JJ, García P, Garrido A (2002) Use of 1-acetoxypinoresinol to authenticate Picual olive oils. Int J Food Sci Technol 37:615-625
17. Cardoso SM, Guyot S, Marnet N, Lopes-da-Silva JA, Renard CM, Coimbra MA (2005) Characterisation of phenolic extracts from olive pulp and olive pomace by electrospray mass spectrometry. J Sci Food Agric 85:21-32
18. Carrasco-Pancorbo A, Cruces-Blanco C, Segura-Carretero A, Fernández-Gutiérrez A (2004) Sensitive determination of phenolic acids in extra-virgin olive oil by capillary zone electrophoresis. J Agric Food Chem 52:6687-6693
19. Carrasco-Pancorbo A, Cerratani L, Bendini A, Segura-Carretero A, Gallina-Toshi T, Fernández-Gutierréz A (2005a) Analytical determination of polyphenols in olive oils. J Sep Sci 28:837-858
20. Carrasco-Pancorbo A, Cerretani L, Bendini A, Segura-Carretero A, Del Carlo M et al (2005b) Evaluation of the antioxidant capacity of individual phenolic compounds in virgin olive oil. J Agric Food Chem 53:8918-8925
21. Carrasco-Pancorbo A, Neusüß C, Pelzing M, Segura-Carretero A, Fernández-Gutiérrez A (2007) CE- and HPLC-TOF-MS for the characterization of phenolic compounds in olive oil. Electrophoresis 28:806-821
22. Cartoni GP, Coccioli F, Jasionowska R, Ramires D (2000) HPLC analysis of the benzoic and cinnamic acids in edible vegetable oils. Ital J Food Sci 12:163-173
23. Cerretani L, Salvador MD, Bendini A, Fregapane G (2008) Relationship between sensory evaluation performed by Italian and Spanish official panels and volatile and phenolic profiles of virgin olive oils. Chemosens Percept 1:258-267
24. Christophoridou S, Dais P (2006) Novel approach to the detection and quantification of phenolic compounds in olive oil based on 31P nuclear magnetic resonance spectroscopy. J Agric Food Chem 54:656-664
25. Christophoridou S, Dais P (2009) Detection and quantification of phenolic compounds in olive oil by high resolution 1H nuclear magnetic resonance spectroscopy. Anal Chim Acta 633:283-292
26. Christophoridou S, Dais P, Li-Hong T, Spraul M (2005) 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 53:4667-4679
27. Dais P, Spyros A, Christophoridou S, Hatzakis E, Fragaki G et al (2007) Comparison of analytical methodologies based on 1H and 31PNMR spectroscopy with conventional methods of analysis for the determination of some olive oil constituents. J Agric Food Chem 55:577-584
28. Damtoft S, Franzyk H, Jensen SR (1993) Biosynthesis of secoiridoids in Oleaceae. Phytochemistry 34:1291-1299
29. De Castro LMD, Japón-Luján R (2006) State-of-the-art and trends in the analysis of oleuropein and derivatives. Trends Anal Chem 25:501-510
30. De la Torre-Carbot K, Jauregui O, Gimeno E, Castellote AI, Lamuela-Raventós RM et al (2005) Characterization and quantification of phenolic compounds in olive oils by solid-phase extraction, HPLC-DAD and HPLC-MS/MS. J Agric Food Chem 53:4331-4340
31. Del Carlo M, Sacchetti G, Di Mattia C, Compagnone D, Mastrocola D et al (2004) Contribution of the phenolic fraction to the antioxidant activity and oxidative stability of olive oil. J Agric Food Chem 52:4072-4079
32. Esti M, Cinquanta L, La Notte E (1998) Phenolic compounds in different olive varieties. J Agric Food Chem 46:32-35
33. Esti M, Contini M, Moneta E, Sinesio F (2009) Phenolics compounds and temporal perception of bitterness and pungency in extra-virgin olive oils: changes occurring throughout storage. Food Chem 113:1095-1100
34. European Communities (EC) (2002) Official Journal of the Commission of the European Communities. Regulation no.796/2002, L.128, May 6th pp 8-28
35. Exarchou V, Godejohann M, van Beek TA, Gerothanassis IP, Vervoort J (2003) LC-UV-solid phase extraction-NMR-MS combined with a cryogenic flow probe and its application to the identification of compounds present in Greek oregano. Anal Chem 75:6288-6294
36. Favati F, Caporale G, Monteleone E, Bertuccioli M (1995) Rapid extraction and determination of phenols in extra virgin olive oil. In: Charalambous G (ed) Food flavors: generation, analysis and process influence. Elsevier Science BV, Amsterdam, pp 429-452
37. García-González DL, Aparicio R (2010) Research in olive oil: challenges for the near future. J Agric Food Chem 58:12569-12577
38. García-Mesa JA, Pereira-Caro G, Fernández-Hernández A, García-Ortíz A et al (2008) Influence of lipid matrix in the bitterness perception of virgin olive oil. Food Qual Prefer 19:421-430
39. García-Villalba R, Pacchiarotta T, Carrasco-Pancorbo A, Segura-Carretero A, Fernández-Gutiérrez A et al (2011) A gas chromatography-atmospheric pressure chemical ionization-time of flight mass spectrometry for profiling of phenolic compounds in extra virgin olive oil. J Chromatogr A 1218:959-971
40. Gomez-Rico A, Salvador MD, la Greca M, Fregapane G (2006) Phenolic and volatile compounds of extra virgin olive oil (Olea europaea L. cv. Cornicabra) with regard to fruit ripening and irrigation management. J Agric Food Chem 54:7130-7136
41. Gomez-Rico A, Fregapane G, Salvador MD (2008) Effect of cultivar and ripening on minor components in Spanish olive fruits and their corresponding virgin olive oils. Food Res Inter 41:433-440
42. Gutiérrez F, Perdiguero S, Gutiérrez R, Olias JM (1992) Evaluation of the bitter taste in virgin olive oil. J Am Oil Chem Soc 69:394-395
43. Gutiérrez-Rosales F, Ríos JJ, Gómez-Rey ML (2003) Main polyphenols in the bitter taste of virgin olive oil. Structural confirmation by on-line high-performance liquid chromatography electrospray ionization mass spectrometry. J Agric Food Chem 51:6021-6025
44. Gutiérrez-Rosales F, Romero MP, Casanovas M, Motilva MJ, Mínguez-Mosquera MI (2010) Metabolites involved in oleuropein accumulation and degradation in fruits of Olea europaea L. Hojiblanca and Arbequina varieties. J Agric Food Chem 58:12924-12933
45. Harborne JB (1989) Methods in plant biochemistry. In: Dey PM, Harborne JB (eds) Series of plant phenolics: volume 1. Academic Press, London, pp 1-28
46. Hrncirik K, Fritsche S (2004) Comparability and reliability of different techniques for the determination of phenolic compounds in virgin olive oil. Eur J Lipid Sci Technol 106:540-549
47. Hurtado-Fernández E, Gómez-Romero M, Carrasco-Pancorbo A, Fernández-Gutiérrez A (2010) Application and potential of capillary electroseparation methods to determine antioxidant phenolic compounds from plant food material. J Pharm Biomed Anal 53:1130-1160
48. Inarejos-García AM, Androulaki A, Salvador MD, Fregapane G, Tsimidou MZ (2009) Discussion on the objective evaluation of virgin olive oil bitterness. Food Res Int 42:279-284
49. International Olive Council (IOC) (2009) Method COI/T.20/Doc. No 29. Determination of biophenols in olive oils by HPLC, Madrid
50. Jemai H, Bouaziz M, Sayadi S (2009) Phenolic composition, sugar contents and antioxidant activity of Tuinisian sweet olive cultivar with regard to fruit ripening. J Agric Food Chem 57:2961-2968
51. Marsilio V, D'Andria R, Lanza B, Russi F, Iannucci E et al (2006) Effect of irrigation and lactic acid bacteria inoculants on the phenolic fraction, fermentation and sensory characteristics of olive (Olea europaea L. cv. Ascolana tenera) fruits. J Sci Food Agric 86:1005-1013
52. Mateos R, Espartero JL, Trujillo M, Ríos JJ (2001) Determination of phenols, flavones, and lignans in virgin olive oils by solid-phase extraction and high-performance liquid chromatography with diode array ultraviolet detection. J Agric Food Chem 49:2185-2192
53. Mateos R, Cert A, Pérez-Camino C, García JM (2004) Evaluation of virgin oil bitterness by quantification of secoiridoid derivatives. J Am Oil Chem Soc 81:71-76
54. Montedoro GF, Cantarelli C (1969) Indagini sulle sostanze fenoliche presenti negli oli d'oliva. Riv Ital Sost Grasse 46:3-12
55. Montedoro GF, Servili M, Baldioli M, Miniati E (1992a) Simple and hydrolyzable phenolic compounds in virgin olive oil. 1. Their extraction, separation, and quantitative and semiquantitative evaluation by HPLC. J Agric Food Chem 40:1571-1576
56. Montedoro GF, Servili M, Baldioli M, Miniati E (1992b) Simple and hydrolyzable phenolic compounds in olive oil: 2. Their extraction, separation, and quantitative and semi-quantitative separation and evaluation by HPLC. J Agric Food Chem 40:1577-1580
57. Montedoro GF, Servili M, Baldioli M, Selvaggini R, Miniati E et al (1993) Simple and hydrolyzable phenolic compounds in olive oil: 3. Spectroscopic characterization of the secoiridoid derivatives. J Agric Food Chem 41:2228-2234
58. Monteleone E, Carlucchi A, Caporale G (1997) Use of slope analysis to characterize consumer preference for virgin olive oil. Ital J Food Sci 9:133-140
59. Morales MT, Tsimidou M (2000) The role of volatile compounds and polyphenols in olive oil sensory quality. In: Harwood J, Aparicio R (eds) Handbook of olive oil: analysis and properties. Aspen Publishers, Gaitesburg, pp 393-438, and references therein
60. Morello J, Motilva M, Tovar M (2004) Changes in commercial virgin olive oil (cv. Arbequina) during storage, with special emphasis on the phenolic fraction. Food Chem 85:357-364
61. Ouni Y, Taamalli A, Gómez-Caravaca AM, Segura-Carretero A, Fernandez-Gutiérrez A et al (2011) Characterisation and quantification of phenolic compounds of extra-virgin olive oils according to their geographical origin by a rapid and resolutive LC-ESI-TOFMS method. Food Chem 127:1263-1267
62. Papoti VT, Tsimidou MZ (2009) Looking through the qualities of a fluorimetric assay for the total phenol content estimation in virgin olive oil, olive fruit or leaf polar extract. Food Chem 112:246-252
63. Pérez-Trujillo M, Gómez-Caravaca AM, Segura-Carretero A, Fernández-Gutiérrez A, Parella AT (2010) Separation and identification of phenolic compounds of extra virgin olive oil from Olea europaea L by HPLC-DAD-SPE-NMR/MS. Identification of a new diastereoisomer of the adehydic form of oleuropein aglycone. J Agric Food Chem 58:9129-9136
64. Pirisi FM, Cabras P, Falqui Cao C, Migliorini M, Muggelli M (2000) Phenolic compounds in virgin olive oil. 2. Reappraisal of the extraction, HPLC separation, and quantification procedures. J Agric Food Chem 48:1191-1196
65. Ranalli A, Serraiocco A (1996) Evaluation of characteristics of olive oil produced by innovative or traditional processing technologies. Riv Ital Sost Grasse 73:303-314
66. Ríos JJ, Gutiérrez-Rosales F (2010) Comparison of methods extracting phenolic compounds from lyophilised and fresh olive pulp. LWT-Food Sci Technol 43:1285-1288
67. Ríos JJ, Gil MJ, Gutiérrez-Rosales F (2005) Solid-phase extraction gas chromatography-ion trap-mass spectrometry qualitative method for evaluation of phenolic compounds in virgin olive oil and structural confirmation of oleuropein and ligstroside aglycons and their oxidation products. J Chromatogr A 1093:167-176
68. Rodríguez-Méndez ML, Apetrei C, De Saja J (2010) Electronic tongues purposly designed for the organoleptic characterization of olive oils. In: Preedy VR, Watson RR (eds) Olives and olive oil in health and disease prevention. Elsevier Academic Press, Amsterdam, pp 525-532
69. Romero C, Garcia P, Brenes M, Garcia A, Garrido A (2002a) Phenolic compounds in natural black Spanish olive varieties. Eur Food Res Technol 215:489-496
70. Romero MP, Tovar MJ, Girona J, Motilva MJ (2002b) Changes in the HPLC phenolic profile of virgin olive oil from young trees (Olea europaea L. cv. Arbequina) grown under different deficit irrigation strategies. J Agric Food Chem 50:5349-5354
71. Rotondi A, Bendini A, Cerretani L, Mari M, Lercker G et al (2004) 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 52:3649-3654
72. Ryan D, Robards K, Lavee S (1999a) Changes in phenolic content of olive during maturation. Int J Food Sci Technol 34:265-274
73. Ryan D, Robards K, Lavee S (1999b) Determination of phenolic compounds in olives by reversedphase chromatography and mass spectrometry. J Chromatogr A 832:87-96
74. Ryan D, Lawrence H, Prenzler PD, Antolovich M, Robards K (2001) Recovery of phenolic compounds from Olea europaea. Anal Chim Acta 445:67-77
75. Ryan D, Antonovich M, Prenzel P, Robards K, Lavee S (2002) Biotransformations of phenolic compounds in Olea europaea. Sci Hortic 92:147-176
76. Ryan D, Prenzler PD, Lavee S, Antolovich M, Robards K (2003) Quantitative changes in phenolic content during physiological development of the olive (Olea europaea) cultivar Hardy's Mammoth. J Agric Food Chem 51:2532-2538
77. Saitta M, Salvo F, Di Bella G, Dugo G, La Torre GL (2009) Minor compounds in the phenolic fraction of virgin olive oils. Food Chem 112:525-532
78. Segura-Carretero A, Carrasco-Pancorbo A, Bendini A, Cerretani L (2010) Analytical determination of polyphenols in olive oil. In: Preedy VR, Watson RR (eds) Olives and olive oil in health and disease prevention. Elsevier Academic Press, Amsterdam, pp 509-523
79. Selvaggini R, Servili M, Urbani S, Esposto S, Taticchi A et al (2006) Evaluation of phenolic compounds in virgin olive oil by direct injection in high-performance liquid chromatography with fluorometric detection. J Agric Food Chem 54:2832-2838
80. Servili M, Selvaggini R, Esposto S, Taticchi A, Montedoro G et al (2004) 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 1054:113-127
81. Servilli M, Baldioli M, Salvaggini R, Macchioni A, Montedoro JF (1999) Phenolic compounds of olive fruit: one- and two-dimensional Nuclear Magnetic Resonance characterization of nuzhenide and its distribution in the constitutive parts of fruit. J Agric Food Chem 47:12-18
82. Siliani S, Mattei A, Innocenti LB, Zanoni B (2006) Bitter taste and phenolic compounds in extra virgin olive oil: an empirical relationship. J Food Qual 29:431-441
83. Suárez M, Macià A, Romero MP, Motilva MJ (2008) Improved liquid chromatography tandem mass spectrometry method for the determination of phenolic compounds in virgin olive oil. J Chromatogr A 1214:90-99
84. Tsimidou M (1998) Polyphenols and quality of virgin olive oil in retrospect. Ital J Food Sci 10:99-116
85. Tsimidou M (1999) Analysis of virgin olive oil polyphenols. Semin Food Anal High-Perform Liq Chromatogr 4:13-29
86. Tsimidou M, Litridou M, Boskou D, Pappa-Louisi A, Kotsifaki F et al (1996) On the determination of minor phenolic acids of virgin olive oil by RP-HPLC. Grasas Aceites 47:151-157
87. Vichi S, Romero A, Tous J, Tamames E, Buxaderas S (2008) Determination of volatile phenols in virgin olive oils and their sensory significance. J Chromatogr A 1211:1-7