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 aldehydic form of oleuropein aglycone

Journal of Agricultural and Food Chemistry

Volumn 58, Issue 16, 2010, Pages 9129-9136

  Pérez Trujillo, Míriam ^a   Gómez Caravaca, Ana María ^b   Segura Carretero, Antonio ^b   Fernández Gutiérrez, Alberto ^b   Parella, Teodor ^a  

^a UNIVERSITAT AUTÒNOMA DE BARCELONA   (Spain)

^b UNIVERSITY OF GRANADA   (Spain)

Author keywords

aldehydic form of oleuropein aglycone; HPLC DAD SPE NMR MS; Olea europaea L; olive oil; phenolic compounds

Indexed keywords

AGLYCONES; HPLC-DAD-SPE-NMR/MS; OLEA EUROPAEA L; OLIVE OIL; PHENOLIC COMPOUNDS;

VEGETABLE OILS;

PHENOLS;

ALDEHYDE; OLEUROPEIN; OLIVE OIL; PHENOL DERIVATIVE; PYRAN DERIVATIVE; VEGETABLE OIL;

ARTICLE; CHEMISTRY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; ISOLATION AND PURIFICATION; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OLIVE TREE; SOLID PHASE EXTRACTION;

ALDEHYDES; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; MAGNETIC RESONANCE SPECTROSCOPY; MASS SPECTROMETRY; OLEA; PHENOLS; PLANT OILS; PYRANS; SOLID PHASE EXTRACTION;

OLEA EUROPAEA;

EID: 77956554222     PISSN: 00218561     EISSN: 15205118     Source Type: Journal    
DOI: 10.1021/jf101847e     Document Type: Article

References (36)

1. Fortes, C.; Forastiere, F.; Farchi, S.; Mallone, S.; Trequattinni, T.; Anatra, F.; Schmid, G.; Pericci, C. A. The protective effect of Mediterranean diet on lung cancer. Nut. Cancer 2003, 46, 30-37.
2. Trichopolou, A.; Vasilopoulou, E. Mediterranean diet and longevity.Br. J. Nutr. 2000, 84, S205-209.
3. Visioli, F.; Galli, C. Natural antioxidants and prevention of coronary heart disease: the potential role of olive oil and its minor constituents. Nutr. Metab. Cardiovasc. Dis. 1995, 5, 306-314.
4. Tsimidou, M. Polyphenols and quality of virgin olive oil in retrospect. Ital. J. Food Sci 1998, 10, 99-116.
5. Caponio, F.; Alloggio, V.; Gomes, T. Phenolic compounds of virgin olive oil: influence of paste preparation techniques. Food Chem 1999, 64, 203-209.
6. Cicerale, S.; Conlan, X. A.; Sinclair, A. J. Chemistry and health of olive oil phenolics. Crit. Rev. Food Sci Nutr. 2009, 49, 218-236.
7. Hashim, Y. Z.; Rowland, I. R.; McGlynn, H.; Servili, M.; Selvaggini, R.; Taticchi, A.; Esposto, S.; Montedoro, G.; Kaisalo, L.; Wähälä, K.; Gill, C. I. R. Inhibitory effects of olive oil phenolics on invasion in human colon adenocarcinoma cells in vitro. Int. J. Cancer 2008,122, 495-500.
8. Menéndez, J. A.; Vázquez-Martýn, A.; Garcýa-Villalba, R.; arrasco-Pancorbo, A.; Oliveras-Ferraros, C.; Fernández-Gutiérrez, A.; Segura-Carretero, A.tabAnti-HER2 (erbB2) oncogene effects of phenolic compounds directly isolated from commercial extra-virgin olive oil (EVOO). BMC Cancer 2008, 8, art n. 377 (http://www.biomedcentral.com/bmccancer.artn
9. Paiva-Martins, F.; Fernandes, J.; Rocha, S.; Nascimento, H.;Vitorino, R.; Amado, F.; Borges, F.; Belo, L.; Santos-Silva, A.Effects of olive oil polyphenols on erythrocyte oxidative damage.Mol. Nutr. Food Res. 2009, 53, 609-601.
10. Rýos, J. J.; Gil, M. J.; Gutiérrez-Rosales, F. Solid-phase extractiongas chromatographyion trap-mass spectrometry qualitative methodfor evaluation of phenolic compounds in virgin olive oil and structural confirmation of oleuropein and ligstroside aglycones and their oxidation products. J. Chromatogr., A 2005, 1903, 167-176.
11. Carrasco-Pancorbo, A.; Gómez-Caravaca, A. M.; Cerretani, L.; Bendini, A.; Segura-Carretero, A.; Fernández-Gutiérrez, A. A simple and rapid electrophoretic method to characterize simple phenols, lignans, complex phenols, phenolic acids, and flavonoids in extravirgin olive oil. J. Sep. Sci. 2006, 29, 2221-2233.
12. Gómez Caravaca, A. M.; Carrasco Pancorbo, A.; Canabate Dýaz, B.; Segura Carretero, A.; Fernández Gutiérrez, A. Electrophoretic identification and quantitation of compounds in the polyphenolic fraction of extra-virgin olive oil. Electrophoresis 2005, 26, 3538-3551.
13. Suárez, M.; Macià, A.; Romero, M. P.; Motilva, M. J. Improved liquid chromatography tandem mass spectrometry method for the determination of phenolic compounds in virgin olive oil. J. Chromatogr., A 2008, 1214 90-99.
14. Tsimidou, M.; Papadopoulos, G.; Boskou, D. Determination of phenolic compounds in virgin olive oil by reversed-phase HPLC with emphasis on UV detection. Food Chem 1992, 44, 53-60.
15. Brenes, M.; Garcýa, A.; Garcýa, P.; Garrido, A. Rapid and complete extraction of phenols from olive oil and determination by means of a coulometric electrode array system. J. Agric. Food Chem 2000, 48, 5178-5183.
16. Cartoni, G. P.; Coccioli, F.; Jasionowska, R.; Ramires, D. HPLC analysis of the benzoic and cinnamic acids in edible vegetable oils. Ital. J. Food Sci 2000, 12, 163-173.
17. 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 solidphase extraction HPLC-DAD, and HPLC-MS/MS. J. Agric. Food Chem 2005, 53, 4331-4340.
18. Sandvoss, M.; Glaser, T.; Albert,K. LC-NMR for natural products. In On-line LC-NMR and Related Techniques; Albert, K., Ed.; Wiley: New York, 2004; pp 109-128.
19. Jaroszewski, J. W. Hyphenated NMR methods in natural products research. Part 1. Direct hyphenation. Planta Med. 2005, 71, 691-700.
20. Corcoran, O.; Wilkinson, P. S.; Godejohann, M.; Brauman, U.; Hoffman, M.; Spraul, M. Advanced sensitivity for flow NMR spectroscopy: LC-SPE-NMR and capillary scale LC-NMR. Am.Lab Chromatogr. Perspect. 2002, 5, 18-21.
21. Exarchou, V.; Godejohann, M.; van Beek, T. A.; Gerothanassis, I. P.; Vervoort, J. 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 2003,75, 6288-6294.
22. Griffiths, L.; Horton, R. Optimization of LC-NMR. III. Increased signal-to-noise ratio through column trapping. Magn. Reson. Chem 1998, 36, 104-109.
23. Clarkson, C.; Staerk, D.; Hansen, S. H.; Jaroszewski, J. W. Hyphenation of solid-phase extraction with liquid chromatography and nuclear magnetic resonance: application of HPLC-DAD-SPENMR to identification of constituents of Kanahia laniflora. Anal. Chem 2005, 77, 3547-3553.
24. Exarchou, V.; Fiamegos, Y. C.; van Beek, T. A.; Nanos, C.; Vervoort, J. Hyphenated chromatographic techniques for the rapid screening and identification of antioxidants in methanolicextracts of pharmaceutically used plants. J. Chromatogr., A 2006, 1112, 293-302.
25. Seger, C.; Godejohann, M.; Tseng, L. H.; Spraul, M.; Girtler, A.; Sturm, S.; Stuppner, H. LC-DAD-MS/SPE-NMR Hyphenation. A tool for the analysis of pharmaceutically used plant extracts: dentification of isobaric iridoid glycoside regioisomers from Harpagophytum procumbens. Anal. Chem 2005, 77, 878-885.
26. Christophoridou, S.; Dais, P.; Tseng, L. I.-H.; Spraul, M. Separation and identification of phenolic compounds in olive oil by coupling high-performance liquid chromatography with postcolumn solidphase extraction to nuclear magnetic resonance spectroscopy (LCSPE-NMR). J. Agric. Food Chem 2005, 53, 4667-4679.
27. Metropolis, N.; Ulam, S. The Monte Carlo method. J. Am. Stat. Assoc. 1949, 44, 335-341.
28. Chang, G.; Guida,W. C.; Still, W. C. An internal-coordinate Monte Carlo method for searching conformational space. J. Am. Chem Soc. 1989, 111, 4379-4386.
29. Garcýa-Villalba, R.; Carrasco-Pancorbo, A.; Vázquez- Martýn, A.; Oliveras-Ferraros, C.;Menéndez, J.; Segura-Carretero, A.; Fernández-Gutiérrez, A. A 2-D-HPLC-CE platform coupled to ESI-TOF-MS to characterize the phenolic fraction in olive oil. Electrophoresis 2009, 30, 2688-2701.
30. 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.
31. Christophoridou, S.; Dais, P. Detection and quantification of phenolic compounds in olive oil by high resolution 1H nuclear magnetic resonance spectroscopy. Anal. Chim. Acta 2009, 633, 283-292.
32. Gariboldi, P.; Jommi, G.; Verrota, L. Secoiridoids from Olea europaea.Phytochemistry 1986,25, 865-869.
33. Kelly, R. C.; Schletter, I. Total synthesis of dl-methyl elenoate.J. Am. Chem Soc. 1973, 95, 7156-7157.
34. MacKellar, F. A.; Kelly, R. C.; VanTamelen, E. E.; Dorschel, C. Structure and stereochemistry of elenolic acid. J. Am. Chem Soc. 1973, 95, 7155-7156.
35. Baggiolini, E. G.; Pizzolato, G.; Uskokovic, M. R. Stereocontrolled synthesis of 19-epiajmalicine from loganin aglucone. Tetrahedron 1988, 44, 3203-3208.
36. Inouye, H.; Yoshida, T.; Tobita, S.; Tanaka, K.; Nishioka, T. Absolute struktur des oleuropeins und einiger verwandter glucoside. Tetrahedron Lett. 1970, 28, 2459-2464.