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)

Journal of Agricultural and Food Chemistry

Volumn 53, Issue 12, 2005, Pages 4667-4679

  Christophoridou, Stella ^a   Dais, Phtis ^a   Tseng, L I Hong ^b   Spraul, Manfred ^b  

^a UNIVERSITY OF CRETE   (Greece)

^b BRUKER BIOSPIN GMBH   (Germany)

Author keywords

LC SPE NMR; Olive oil; Phenolic compounds

Indexed keywords

FLAVONOID; IRIDOID; LIGNAN; OLIVE OIL; PHENOL DERIVATIVE; VEGETABLE OIL;

ARTICLE; CHEMISTRY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; ISOLATION AND PURIFICATION; METHODOLOGY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;

CHROMATOGRAPHY, HIGH PRESSURE LIQUID; FLAVONOIDS; IRIDOIDS; LIGNANS; MAGNETIC RESONANCE SPECTROSCOPY; PHENOLS; PLANT OILS;

EID: 21644485321     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf040466r     Document Type: Article

References (55)

1. Gutierrez Gonzales-Quijano, R. C.; Janer del Valle, C.; Janer del Valle, M. L.; Gurierrez Rosales, F.; Vazquez Roncero, A. Relationship between polyphenol content and the quality and stability of virgin olive oil. Grasas Aceites 1977, 28, 101-106.
2. Tsimidou, M. Polyphenols and quality of virgin olive oil in retrospect. Ital. J. Food Sci. 1998, 10, 99-116.
3. Owen, R. W.; Giacosa, A.; Hull, W. E., Haubner, R.; Wurtele, G.; Spiegelhalder, B.; Bartsch, H. Olive-oil consumption and health: The possible role of antioxidants. Lancet Oncol. 2000, 1, 107-112.
4. Owen, R. W.; Giacosa, A.; Hull, W. E.; Haubner, R.; Spiegel-halder, B.; Bartsch, H. The antioxidant/anticancer potential of phenolic compounds isolated from olive oil. Eur. J. Cancer 2000, 36, 1235-1247.
5. Morales, M. T.; Tsimidou, M. The role of volatile compounds and polyphenols in olive oil sensory quality. In Handbook of Olive Oil: Analysis and Properties; Aparicio, R., Harwood, J., Eds.; Kluwer Academic/Plenum Publishers: New York, 1999; Chapter 12, pp 393-455.
6. 13C NMR of virgin oil. An overview. Magn. Reson. Chem. 1997, 35, S5133-S5145.
7. Vlahov, G. Application of NMR to the study of olive oils. Prog. Nucl. Magn. Reson. Spectrosc. 1999, 35, 341-357.
8. Owen, R. W.; Mier, W.; Giacosa, A.; Hull, W. E.; Spiegelhalder, B.; Bartsch, H. Identification of lignans as major components in the phenolic fraction of olive oil. Clin. Chem. 2000, 46, 976-988.
9. Owen, R. W.; Haubner, R.; Mier, W.; Giacosa, A.; Hull, W. E.; Spiegelhalder, B.; Bartsch, H. Isolation, structure elucidation and antioxidant potential of the major phenolic and flavonoid compounds in brined olive drupes. Food Chem. Toxicol. 2003, 41, 703-717.
10. 13C NMR characterization of new oleuropein aglycones. J. Chem. Soc., Perkin Trans. 1995, 1519-1523.
11. Montedoro, G.; Servili, M.; Baldioli, M.; Selvaggini, R.; Miniati, E.; Macchioni, A. Simple and hydrolyzable compounds in virgin olive oil. 3. Spectroscopic characterizations of secoiridoids derivatives. J. Agric. Food Chem. 1993, 41, 2228-2234.
12. Gariboldi, P.; Jommi, G.; Verrota, L. Secoiridoids from Olea europaea. Phytochemistry 1986, 25, 865-869.
13. Bianco, A.; Uccella, N. Biophenolic components of olives. Food Res. Int. 2000, 33, 475-485.
14. Lindon, J. C.; Nicholson, J. K.; Wilson, I. D. Direct coupling of Chromatographic separations to NMR spectroscopy. Prog. NMR Spectrosc. 1996, 29, 1-49.
15. Spraul, M. Hyphenated methods in NMR. In Magnetic Resonance in Food Science. A View to the Future; Webb, G. A., Belton, P. S., Gil, A. M., Delgadillo, I., Eds.; Royal Society of Chemistry: London, U.K., 2001; pp 54-66.
16. Pusecker, K.; Albert, K.; Bayer, E. Investigation of hop beer bitter acids by coupling of high performance liquid chromatography to nuclear magneic resonance spectroscopy. J. Chromatogr. A 1999, 836, 245-252.
17. Strochshein, S.; Rentel, C.; Lacher, T.; Bayer, E.; Albert, K. Separation and identofication of tocotrienol isomers by HPLC-MS and HPLC-NMR coupling. Anal. Chem. 1999, 71, 1780-1785.
18. Lommen, A.; Godejohann, M.; Venema, D. P.; Hollman, P. C. H.; Spraul, M. Application of directly coupled HPLC-NMR-MS to the identification and confirmation of querquetin glucosides and phloretin glycosides in apple peal. Anal. Chem. 2000, 72, 1793-1797.
19. Sanvoss, M.; Roberts, A. D.; Ismail, I. M.; North, S. E. Direct on-line hyphenation of capillary liquid chromatography to nuclear magnetic resonance spectroscopy. Practical aspects and application to drug metabolite identification. J. Chromatogr. A 2004, 1028, 259-266.
20. Hansen, S. H.; Jensen, A. G.; Cornett, C.; Bjornsdottir, L; Taylor, S.; Wright, B.; Wilso, I. D. High performance liquid chromatography on line coupled to high field NMR and mass spectrometry for structure elucidation of constituents of Hypericum perforatum L. Anal. Chem. 1999, 77, 5235-5241.
21. Gil, A. M.; Duarte, I. F.; Godejohan, M.; Braumann, U.; Maraschin, M. Spraul, M. Characterization of the aromatic composition of some liquid foods by nuclear magnetic resonance spectrometry and liquid chromatography with nuclear magnetic resonance and mass spectrometric detection. Anal. Chim. Acta 2003, 488, 35-51.
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. 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.
24. 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.
25. Montedoro, G.; Servili, M.; Baldioli, M.; Selvaggini, R.; Miniati, E.; Simple and hydrolyzable compounds in virgin olive oil. 1. Their extraction, separation and semiquantitative evaluation by HPLC. J. Agric. Food Chem. 1992, 40, 1571-1576.
26. Esti, M.; Cinquanta, L.; La Notte, E. Phenolic compounds in different olive varieties. J. Agric. Food Chem. 1998, 46, 32-35.
27. Brenes, M.; Garcia, A.; Garcia, P.; Rios, J. J.; Garrido, A. Phenolic compounds in Spanish olive oils. J Agric. Food Chem. 1999, 47, 3535-3540.
28. Rovellini, R.; Cortesi, N.; Fedeli, E. Analysis of flavonoids from Olea europaea L. by HPLC-UV and HPLC-electron spray-MS. Riv. Iiai. Sostanze Grasse 1997, 74, 273-279.
29. Romani, A.; Mulinacci, N.; Pinelli, P.; Vincieri, F. F.; Cimato, A. Polyphenolic content in five Tuscany cultivars of Olea europaea L. J. Agric. Food Chem. 1999, 47, 964-967.
30. Gomez-Alonso, S.; Desamparados Salvador, M.; Fregapane, G. Phenolic compounds profile of cornicabra virgin olive oil. J. Agric. Food Chem. 2002, 50, 6812-6817.
31. Mateos, R.; Espartero, J. L.; Trujillo, M.; Rios, J. J.; Leon-Camacho, M.; Alcudia, F.; Cert, A. Determination of phenols, flavones, and lignans in virgin olive oils by solid phase extraction and high-performance liquid chromatography with diode arrayultraviolet detection. J. Agric. Food Chem. 2001, 49, 2185-2192.
32. Gutierez-Rosales, F.; Rios, J. J.; Gomez-Rey, Ma. L. 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. 2003, 51, 6021-6025.
33. Gordon, M.; Palva-Martins, F.; Almeida, M. Antioxidant activity of hydroxytyrosol acetate compared with that of other olive oil polyphenols. J. Agric. Food Chem. 2001, 49, 2480-2485.
34. Gerothanasis, L; Exarchou, V.; Lagouri, V.; Troganis, A.; Tsimidou, M.; Boskou, D. Methodology for identification and quantification of phenolic acids in complex phenolic mixtures by high-resolution two-dimensional nuclear magnetic resonance. Application to methanolic extracts of two oregano species. J. Agric. Food Chem. 1998, 46, 4185-4192.
35. El-Hassan, A.; El-Sayed, M.; Hamed, A. L; Rhee, I. K.; Ahmed, A. A.; Zeller, K. P.; Verpoorte, R. Bioactive constituents of Leptadenia arborea. Fitoterapia 2003, 74, 184-187.
36. Nurmi, T.; Voutilainen, S.; Nyyssonen, K.; Adlercreutz, H.; Salonen, J. T. Liquid chromatography method for plant and mammalian lignans in human urine. J. Chromatogr. B 2003, 798, 101-110.
37. Boriello, S. P.; Setchell, K. D. R.; Axelson, M.; Lawson, A. M. Production and metabolism of lignans by the human faucal flora. J. Appl. Bacterial. 1985, 58, 37-43.
38. Adlercreutz, H. Epidemiology of phytoestrogens. In Bailliere's Clinical Endocrinology and Metabolism: Phyto-oestrogens; Adlercreutz, H., Ed.; Bailliere Tindal: London, U.K., 1998; pp 605-623.
39. Thompson, L. U. Experimental studies on lignans and cancer. In Bailliere's Clinical Endocrinology and Metabolism: Phytooestrogens; Adlercreutz, H., Ed.; Bailliere Tindal: London, U.K., 1998; pp 691-706.
40. Vanharanta, M.; Voutileinen, S.; Lakka, T. A.; van der Lee, M.; Adlercreutz, H.; Salonen, J. T. Risk of acute coronary events according to serum concentrations of enterolactone: A prospective population-based case-control study. Lancet 1999, 354, 2112-2115.
41. Pietinen, P.; Stumpf, K.; Mannisto, S.; Kataja, V.; Unsitupa, M.; Adlercreutz, H. Serum enterolactone and risk of breast cancer: a case-control study in eastern Finland. Cancer Epidemiol., Biomarkers Prevent. 2001, 10, 339-344.
42. Bianco, A. D.; Piperno, A.; Romeo, G.; Ucella, N. NMR experiments of oleuropein biomimetic hydrolysis. J. Agric. Food Chem. 1999, 47, 3665-3668.
43. Bianco, A. D.; Mazzalupo, I.; Piperno, A.; Romeo, G.; Ucella, N. Bioactive derivatives of oleuropein from olive fruits. J. Agric. Food Chem. 1999, 47, 3531-3534.
44. Kubo, I.; Matsumoto, A.; Takase, I. A multichemical defense mechanism of bitter olive Olea europaea (Oleacaea). Is oleuropein a phytoalexin precursor? J. Chem. Ecol. 1985, 11, 251-263.
45. Lo Scalzo, R.; Scarpati, M. L.; Verregnassi, B.; Vita, G. Olea europaea chemicals repellents to Dacus oleae females. J. Chem. Ecol. 1994, 20, 1813-1823.
46. El Gamal, A. A.; Takeya, K.; Itokawa, H.; Halim, A. F.; Amer, M. M.; Saad, H.-E. A. Lignan bis-glucosides from Galium sinaicum. Phytochemistry 1997, 45, 797-600.
47. Erdemoglu, N.; Sahun, E.; Sener, B.; Ide, S. Structural and spectroscopic characteristics of two lignans from Taxus baccata L. J. Mol Struct. 2004, 692, 57-62.
48. Shoeb, M.; Jaspars, M.; MacManus, S. M.; Majinda, R. R. T.; Sarker, S. D. Epoxylignans from seeds of Centaurea cyanus (Asteraceae). Biochem. Syst. Ecol. 2004, 32, 1201-1204.
49. Sartoreli, P.; Young, M. C. M.; Kato, M. J. Antifugal lignons from the arils of Virola oleifera. Phytochemistry 1998, 47, 1003-1006.
50. Konishi, T.; Konoshima, T.; Daikonya, A.; Kitanaka, S. Neolignans from Piper futokadsura and their inhibition of nitric oxide production. Chem. Pharm. Bull. 2005, 53, 121-124.
51. Abou-Gazar, H.; Bedir, E.; Takamatsu, S.; Ferreira, D.; Kahn, I. A. Antioxidant lignans from Larrea tridentata. Phytochemistry 2004, 65, 2499-2505.
52. Raffaelli, B.; Hoikkala, A.; Leppala, E.; Wahala, K. Enterotignans. J. Chromatogr. B 2002, 777, 29-43.
53. Dinkova-Kostova, A.; Gang, D. R.; Davin, L. B.; Nedgar, D. L.; Chu, A.; Lewis, N. G. (+)-Pinoresinol/(+)-lariciresinol reductase from Forsythia intermedia. J. Biol. Chem. 1996, 277, 29473-29482.
54. Tanaka, J. C. A.; Vidotti, G. J.; da Silva, C. C. A new tormentic acid derivative from Luehea divaricata Mart. J. Braz. Chem. Soc. 2003, 14, 475-478.
55. Bilia, A. R.; Mendez, J.; Morelli, I. Phytochemical investigations of Licania genus. Flavonoids and triterpenoids from Licania carii. Pharm. Acta Helv. 1996, 71, 191-197.