Oleuropein site selective hydrolysis by technomimetic nuclear magnetic resonance experiments

Journal of Agricultural and Food Chemistry

Volumn 48, Issue 5, 2000, Pages 1623-1629

  Capozzi, F ^a   Piperno, A ^b   Uccella, N ^a  

^a UNIVERSITY OF CALABRIA   (Italy)

^b UNIVERSITY OF MESSINA   (Italy)

Author keywords

Basic oleuropein hydrolysis; Biophenols and secoiridoids; Table olive processing; Technomimetic NMR experiments

Indexed keywords

ALKALI; ESTER; GLUCOSIDE; OLEUROPEIN; PYRAN DERIVATIVE; SECOIRIDOID;

ARTICLE; CHEMISTRY; HYDROLYSIS; METHODOLOGY; NONHUMAN; NUCLEAR MAGNETIC RESONANCE;

HYDROLYSIS; MAGNETIC RESONANCE SPECTROSCOPY; PYRANS;

EID: 0034111245     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf991178b     Document Type: Article

References (39)

1. Amiot, M. J.; Fleuriet, A.; Machiex, J. J. Importance and evolution of phenolic compounds in olive during growth and maturation. J. Agric. Food Chem. 1986, 34, 823-826.
2. Amiot. M. J.; Fleuriet, A.; Macheix, J. J. Accumulation of oleuropein derivatives during olive maturation. Phytochemistry 1989, 28, 67-69.
3. Balatsouras, G. Table olive processing technology. In World Olive Encyclopaedia; Lucchetti, F., Ed.; IOOC: Madrid, Spain, 1996.
4. Bianco, A. D.; Chiacchio, U.; Rescifina, A.; Romeo, G.; Uccella, N. Biomimetic Supramolecular Biophenol-Carbohydrate and Biophenol-Protein Models by NMR Experiments. J. Agric. Food Chem. 1997, 45, 4281-4285.
5. Bianco, A. D.; Mazzei, R. A.; Melchioni, C.; Romeo, G.; Scarpati, M. L.; Soriero, A.; Uccella, N. Microcomponents of Olive Oil-III. Glucosides of 2(3,4-dihydroxyphenyl)ethanol. Food Chem. 1998, 63, 461-464.
6. Bianco, A. D.; Piperno, A.; Romeo, G.; Uccella, N. NMR experiments of oleuropein biomimetic hydrolysis. J. Agric. Food Chem. 1999a, 47, 3665-3668.
7. Bianco, A. D.; Muzzalupo, I.; Piperno, A.; Romeo, G.; Uccella, N. Bioactive derivatives of oleuropein from olive fruits. J. Agric. Food Chem. 1999b, 47, 3531-3534.
8. Bianco, A. D.; Uccella, N. Biophenolic Components of Olives. Food Res. Int. 2000, in press.
9. Bisignano, G.; Tomaino, A.; Lo Cascio, R.; Crisafi, G.; Uccella, N.; Saija, A. On the In-vitro Antimicrobial Activity of Oleuropein and Hydroxytyrosol. J. Pharm. Pharmacol. 1999, 51, 971-974.
10. Borzillo, A.; Iannotta, N.; Uccella, N. Oinotria Table Olives: Quality Evaluation during Ripening and Processing by Biomolecular Components. Eur. Food Res. Technol. 2000, in press.
11. Brenes, M.; de Castro, A. Transformation of Oleuropein and its Hydrolysis Products during Spanish-style Green Olive Processing. J. Sci. Food Agric. 1998, 77, 353-358.
12. Brenes, M.; Rejano, L.; Garcia, P.; Sanchez, A. H.; Garrido, A. Biochemical Changes in Phenolic Compounds during Spanish Style Green Olive Processing. J. Agric. Food Chem. 1995, 43, 2702-2706.
13. Brenes-Balbuena, M.; Garcia, P.; Garrido, A. Phenolic compounds related to the black color formed during the processing of ripe olives. J. Agric. Food Chem. 1992, 40, 1192-1196.
14. Brighigna, A. Le Olive da Tavola; Edagricole: Bologna, Italy, 1998.
15. Castelli, F.; Uccella, N.; Trombetta, D.; Saija, A. Differences between Coumaric and Cinnamic Acids in Membrane Permeation as Evidenced by Time-Dependent Calorimetry. J. Agric. Food Chem. 1999, 47, 991-995.
16. Casuscelli, F.; De Nino, A.; Gallo, F. R.; Procopio, A.; Romeo, G.; Uccella, N. Olea europea L. Biophenols; Modern Analytical Applications. In Ricerche e Innovazioni nell'Industria Alimentare; Chiriotti Editore: Pinerolo, Italy, 1994; Vol. I.
17. Connell, J. H. History and scope of the olive industry. In Olive Production Manual; Ferguson, L., Steven Sibbett, G., Martin, G. C., Eds.; University of California: Los Angeles, CA, 1994; Publ. 3353, pp 1-10.
18. Damtoft, S.; Franzyk, H.; Jensen, S. R. Excelsioside, a Secoiridoid from Fraxinus excelsior. Phytochemistry 1992, 31, 4197-4201.
19. Gariboldi, P.; Jommi, G.; Verotta, L. Secoiridoids from Olea europea. Phytochemistry 1986, 25, 865-869.
20. Garrido Fernandez, A.; Fernandez Diez, M.; Adams, M. R. Physicochemical Changes in brines and fruit during Fermentation. Table Olives, Production and Processing; Chapman and Hall: London, U.K., 1997a; bp 101.
21. Goldberg, I. Health attributes of functional foods. In Functional Foods; Chapman and Hall: London, U.K., 1994.
22. Gutierrez, F.; Albi, M. A.; Palma, R.; Rios, J. J.; Olias, J. M. Bitter Taste of Virgin Olive Oil: Correlation of Sensory Evaluation and Instrumental HPLC Analysis. J. Food Sci. 1989, 54, 68-70.
23. Haslam, E. Natural polyphenols (vegetable tannins) as drugs: possible mode of action. J. Nat. Prod. 1996, 59, 205-215.
24. Inouye, H.; Yoshida, T.; Tobita, S.; Tanaka, K.; Nishioka, T. Uber die Monoterpenglucoside und Verwandte Naturstoffe-XXII. Absolutstrukturen des Oleuropeins, Kingisids und Morronisids. Tetrahedron 1974, 30, 201-209.
25. Jimenez, A.; Heredia, A.; Guillen, R.; Fernandez-Bolonos, J. Correlation between Soaking Conditions, Cations Content of Cell Wall, and Olive Firmness during Spanish Green Olive Processing. J. Agric. Food Chem. 1997, 45, 1653-1658.
26. Kuwajima, H.; Uemura, T.; Takaishi, K.; Inoue, K.; Inouye, H. A secoiridoid Glucoside from Olea europea. Phytochemistry 1988, 27, 1757-1759.
27. 1H NMR characterization of oleuropein aglycones. J. Chem. Soc., Perkin Trans. 1 1995, 5, 1519-1523.
28. 1H NMR study of phenolics in the vegetation water of three cultivars of Olea europea: similarities and differences. J. Agric. Food Chem. 1996, 44, 2040-2048.
29. Lo Scalzo, R.; Scarpati, M. L.; Verzegnassi, B.; Vita, G. Olea europea Chemicals Repellent to Dacus oleae Females. J. Chem. Ecol. 1994, 20, 1813-1823.
30. Marsilio, V.; Lanza, B.; Pozzi, N. Progress in Table Olive Debittering: Degradation in vitro of Oleuropein and its Derivatives by Lactobacillus plantarum. J. Am. Oil Chem. Soc. 1996, 73, 593-597.
31. Ragazzi, E.; Veronese, G.; Guiotto, A. Demethiloleuropeina, nuovo glucoside isolate da olive mature. Ann. Chim. 1973, 63, 13-27.
32. Romani, A.; Mulinacci, N.; Pinelli, P.; Vincieri, F. F.; Cimato, A. Polyphenolic content in five Tuscany cultivars of Olea europea L. J. Agric. Food Chem. 1999, 47, 964-967.
33. Russo, N.; Toscano, M.; Uccella, N. Semiempirical Molecular Modelling into Quercetin Reactive Site: Structural, Conformational and Electronic Features. J. Agric. Food Chem. 1999, submitted for publication.
34. Saija, A.; Trombetta, D.; Tomaino, D.; Lo Cascio, R.; Princi, P.; Uccella, N.; Bonina, F.; Castelli, F. "In vitro" evaluation of the antioxidant activity and biomembrane interaction of the plant phenols oleuropein and hydroxytyrosol. Int. J. Pharm. 1998, 166, 123-133.
35. Saija, A.; Tomaino, A.; Lo Cascio, R.; Trombetta, D.; Proteggente, A.; De Pasquale, A.; Uccella, N.; Bonina, F. Ferulic and Caffeic as potential protective agents photo-oxidative skin damage. J. Sci. Food Agric. 1999, 79, 232-242.
36. Tsimidou, M. Polyphenols and Quality of Virgin Olive Oil in Retrospect. Ital. J. Food Sci. 1998, 10, 99-116.
37. Vekey, K.; Malorni, A.; Pocsfalvi, G.; Piperno, A.; Romeo, G.; Uccella, N. Biophenol-protein supramolecular models by fast atom bombardment-mass spectrometric experiments. J. Agric. Food Chem. 1997, 45, 2447-2451.
38. Visioli, F.; Galli, C. Olive oil phenols and their potential effects on human health. J. Agric. Food Chem. 1998, 46, 4292-4296.
39. Wiseman, S.; Weisgerber, U.; Tijburg, L.; Korver, O. The Food industry and Functional Foods. In Antioxidant Food Supplements in Human Health; Academic Press: San Diego, CA, 1999.