Interaction between extra virgin olive oil phenolic compounds and mucin

European Journal of Lipid Science and Technology

Volumn 117, Issue 10, 2015, Pages 1569-1577

  Quintero Flórez, Angélica ^a   Sánchez Ortiz, Araceli ^a   Gaforio Martínez, José Juan ^b   Jiménez Márquez, Antonio ^a   Beltrán Maza, Gabriel ^a  

^a IFAPA CENTRO EL TORUÑO   (Spain)

^b UNIVERSITY OF JAÉN   (Spain)

Author keywords

Bioavailability; Mucin; Polyphenol protein interactions; Polyphenols; Virgin olive oil

Indexed keywords

EID: 84944157182     PISSN: 14387697     EISSN: 14389312     Source Type: Journal    
DOI: 10.1002/ejlt.201400613     Document Type: Article

References (56)

1. Carrasco-Pancorbo, A., Cerretani, L., Bendini, A., Segura-Carretero, A., Gallina-Toschi, T., Fernández, A., Analytical determination of polyphenols in olive oils. J. Sep. Sci. 2005, 28, 837-858.
2. Mateos, R., Espartero, J. L., Trujillo, M., Ríos, J. J., León-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 array ultraviolet detection. J. Agric. Food Chem. 2001, 49, 2185-2192.
3. Montedoro, G. M., Servili, M., Baldioli, R., Miniati, E., Simple and hydrolyzable phenolic compounds in virgin olive oil. 1. Their extraction, separation, and quantitative and semiquantitative evaluation by HPLC. J. Agric. Food Chem. 1992, 40, 1571-1576.
4. Montedoro, G. M., Servili, M., Baldioli, R., Selvaggini, E., Miniati, A., Macchioni, J., Simple and hydrolyzable compounds in virgin olive oil. 3. Spectroscopic characterizations of the secoiridoid derivatives. J. Agric. Food Chem. 1993, 41, 2228-2234.
5. Bendini, A., Cerretani, L., Carrasco-Pancorbo, A., Gómez-Caravaca, A., Segura-Carretero, A., Fernández-Gutiérrez, A., Lercker, G., 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 Alessandra Molecules 2007, 12, 1679-1719.
6. Bianco, A., Coccioli, F., Guiso, M., Marra, C., The occurrence in olive oil of a new class of phenolic compounds: hydroxy-isochromans. Food Chem. 2002, 77, 405-411.
7. Brenes, M., Hidalgo, F., García, A., Rios, J., García, P., Zamora, R., Garrido, A., Pinoresinol and 1-acetoxypinoresinol, two new phenolic compounds identified in olive oil. J. Am. Oil Chem. Soc. 2000, 77, 715-720.
8. García, J. M., Yousfi, K., Mateos, R., Olmo, M., Cert, A., Reduction of oil bitterness by heating of olive (Olea europaea) Fruits. J. Agric. Food Chem. 2001, 49, 4231-4235.
9. Andrewes, P., Busch, J. L. H. C., de Joode, T. Groenewegen, S. Alexandre, H. Sensory properties of virgin olive oil polyphenols: Identification of deacetoxy-ligstroside aglycon as a key contributor to pungency. J. Agric. Food Chem. 2003, 51, 1415-1420.
10. Gutiérrez-Rosales, F., Ríos, J. J., Gómez-Rey, M. 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.
11. Beltrán, G., Ruano, M. T., Jiménez, A., Uceda, M., Aguilera, M. P., Evaluation of virgin olive oil bitterness by total phenol content analysis. Eur. J. Lipid. Sci. Technol. 2007, 109, 193-197.
12. Morello, J., Vuorela, S., Romero, M., Motilva, M., Heinonen, M., Antioxidant activity of olive pulp and olive oil phenolic compounds of the Arbequina cultivar. J. Agric. Food Chem. 2005, 53, 2002-2008.
13. Mateos, R., Trujillo, M., Perez-Camino, M. C., Moreda, W., Cert, A., Relationships between oxidative stability, triacylglycerol composition, and antioxidant content in olive oil matrices. J. Agric. Food Chem. 2005, 53, 5766-5771.
14. Dell'Agli, M., Maschi, O., Galli, G. V., Fagnani, R., Dal Cero, E., Caruso, D., Bosisio, E., Inhibition of platelet aggregation by olive oil phenols via cAMP-phosphodiesterase. Br. J. Nutr. 2008, 99, 945-951.
15. Rietjens, S. J., Bast, A., Haenen, G. R. M. M., New insights into controversies on the antioxidant potential of the olive oil antioxidant hydroxytyrosol. J. Agric. Food Chem. 2007, 55, 7609-7614.
16. Covas, M. I., de la Torre, K., Farré-Albaladejo, M., Kaikkonen, J., Fitó, M., López-Sabater, C., Pujadas-Bastardes, M. A., Joglar, J., Weinbrenner, T., Lamuela-Raventós, R. M., de la Torre, R., Postprandial LDL phenolic content and LDL oxidation are modulated by olive oil phenolic compounds in humans. Free. Rad. Biomed. 2006, 40, 608-616.
17. Bitler, C. M., Viale, T. M., Damaj, B., Crea, R., Hydrolyzed olive vegetation water in mice has anti-inflammatory activity 1. J. Nutr. 2005, 135, 1475-1479.
18. Tripoli, E., Giammanco, M., Tabacchi, G., Di Majo, D., Giammanco, S., La Guardia, M., The phenolic compounds of olive oil: structure, biological activity and beneficial effects on human health. Nutr. Res. Rev. 2005, 18, 98-112.
19. O'Dowd, Y., Driss, F., Dang, P. M., Elbim, C., Gougerot-Pocidalo, M. A., Pasquier, C., El-Benna, J., Antioxidant effect of hydroxytyrosol, a polyphenol from olive oil: Scavenging of hydrogen peroxide but not superoxide anion produced by human neutrophils. Biochem. Pharmacol. 2004, 68, 2003-2008.
20. Goya, L., Mateos, R., Bravo, L., Effect of the olive oil phenol hydroxytyrosol on human hepatoma HepG2 cells. Eur. J. Nutr. 2007, 46, 70-78.
21. Warleta, F., Quesada, C. S., Campos, M., Allouche, Y., Beltrán, G., Gaforio, J. J., Hydroxytyrosol protects against oxidative DNA damage in human breast cells. Nutrients 2011, 3, 839-857.
22. Polzonetti, V., Egidi, D., Vita, A., Vincenzetti, S., Natalini, P., Involvement of oleuropein in (some) digestive metabolic pathways. Food Chem. 2004, 88, 11-15.
23. Poncet-Legrand, C., Edelmann, A., Putaux, J., Cartalade, D., Sarni-Manchado, P., Vernhet, A., Poly(L-proline) interactions with flavan-3-ols units: Influence of the molecular structure and the polyphenol/protein ratio. Food Hydrocolloids 2006, 20, 687-697.
24. Bennick, A., Interaction of plant polyphenols with salivary proteins. Crit. Rev. Oral Biol. Med. 2002, 13, 184-196.
25. Siebert, K. J., Effects of protein-polyphenol interactions on beverage haze, stabilization, and analysis. J. Agric. Food Chem. 1999, 47, 353-362.
26. Baxter, N. J., Lilley, T. H., Haslam, E., Williamson, M. P., Multiple interactions between polyphenols and a salivary proline-rich protein repeat result in complexation and precipitation. Biochemistry (N.Y.) 1997, 36, 5566-5577.
27. Siebert, K. J., Troukhanova, N. V., Lynn, P. Y., Nature of polyphenol-protein interactions. J. Agric. Food Chem. 1996, 44, 80-85.
28. Haslam, E., Lilley, T. H., Interactions of natural phenols with macromolecules. Prog. Clin. Biol. Res. 1986, 213, 53-65.
29. Jöbstl, E., O'Connell, J., Fairclough, P. A., Williamson, M. P., Molecular model for astringency produced by polyphenol/protein interactions. Biomacromolecules 2004, 5, 942-949.
30. Charlton, A. J., Baxter, N. J., Khan, M. L., Moir, A. J., Haslam, E., Davies, A. P., Williamson, M. P., Polyphenol/peptide binding and precipitation. J. Agric. Food Chem. 2002, 50, 1593-1601.
31. De Freitas, V., Mateus, N., Structural features of procyanidin interactions with salivary proteins. J. Agric. Food Chem. 2001, 49, 940-945.
32. Naurato, N., Wong, P., Lu, Y., Wroblewski, K., Bennick, A., Interaction of tannin with human salivary histatins. J. Agric. Food Chem. 1999, 47, 2229-2234.
33. Murray, N. J., Williamson, M. P., Lilley, T. H., Haslam, E., Study of the interaction between salivary proline-rich proteins and a polyphenol by 1H-NMR spectroscopy. Eur. J. Biochem. 1994, 219, 923-935.
34. Hagerman, A. E., Butler, L. G., The specificity of proanthocyanidin-protein interactions. J. Biol. Chem. 1981, 256, 4494-4497.
35. McManus, J. P., Davis, K. G., Lilley, T. H., Haslam, E., The association of proteins with polyphenols. J. Chem. Soc. Chem. Commun. 1981, 309b-311.
36. Soares, S., Mateus, N., de Freitas, V., Interaction of different classes of salivary proteins with food tannins. Food Res. Int. 2012, 49, 807-813.
37. Ferrer-Gallego, R., Gonçalves, R., Rivas-Gonzalo, J. C., Escribano-Bailón, M. T., De Freitas, V., Interaction of phenolic compounds with bovine serum albumin (BSA) and a-amylase and their relationship to astringency perception. Food Chem. 2012, 135, 651-658.
38. Perez-Gregorio, M. R., Mateus, N., De Freitas, V., Rapid screening and identification of new soluble tannin-salivary protein aggregates in saliva by mass spectrometry (MALDI-TOF-TOF and FIA-ESI-MS). Langmuir 2014, 30, 8528-8537.
39. de Freitas, V., Mateus, N., Protein/polyphenol interactions: Past and present contributions. Mechanisms of astringency perception. Curr. Org. Chem. 2012, 16, 724-746.
40. Haslam, E., Williamson, M., Charlton, A., Protein-polyphenol interactions. Int. Congr. Symp. Ser. Med. 2000, 25-33.
41. Ozdal, T., Capanoglu, E., Altay, F., A review on protein-phenolic interactions and associated changes. Food Res. Int. 2013, 51, 954-970.
42. Heinonen, M., Rein, M. D., Satué-Gracia, T., Huang, S., German, J. B., Frankel, E. N., Effect of protein on the antioxidant activity of phenolic compounds in a lecithin - liposome oxidation system. J. Agric. Food Chem. 1998, 46, 917-922.
43. Bandyopadhyay, P., Ghosh, A. K., Ghosh, C., Recent developments on polyphenol-protein interactions: Effects on tea and coffee taste, antioxidant properties and the digestive system. Food Funct. 2012, 592-605.
44. Vázquez-Roncero, A., Janer del Valle, C., Janer del Valle, M. L., Determinación de los polifenoles totales en aceite de oliva. Grasas Aceites 1973, 24, 350-357.
45. Monteleone, E., Condelli, N., Dinnella, C., Bertuccioli, M., Prediction of perceived astringency induced by phenolic compounds. Food. Qual. Prefer. 2004, 15, 761-769.
46. De Freitas, V., Mateus, N., Nephelometric study of salivary protein-tannin aggregates. J. Sci. Food Agric. 2002, 82, 113-119.
47. Chapon, L., Nephelometry as a method for studying the relations between polyphenols and proteins. J. Inst. Brewing 1993, 99, 49-56.
48. Hagerman, A. E., Klucher, K. M., Tannin-protein interactions. Prog. Clin. Biol. Res. 1986, 213, 67-76.
49. Van Ruth, S. M., Roozen, J. P., Influence of mastication and saliva on aroma release in a model mouth system. Food Chem. 2000, 71, 339-345.
50. Siebert, K. J., Lynn, P. Y., Comparison of polyphenol interactions with polyvinylpolypyrrolidone and haze-active protein. J. Am. Soc. Brew. Chem. 1998, 56, 24-31.
51. McManus, J. P., Davis, K. G., Beart, J. E., Gaffney, S. H., Lilley, T. H., Haslam, E., Polyphenol interactions. Part 1. Introduction; some observations on the reversible complexation of polyphenols with proteins and polysaccharides. J. Chem. Soc. Perkin Trans. 2, 1985, 1429-1438.
52. Spencer, C. M., Cai, Y., Martin, R., Gaffney, S. H., Goulding, P. N., Magnolato, D., Lilley, T. H., Haslam, E., Polyphenol complexation-some thoughts and observations. Phytochemistry 1988, 27, 2397-2409.
53. Cai, Y., Gaffney, S. H., Lilley, T. H., Magnolato, D., Martin, R., Spencer, C. M., Haslam, E., Polyphenol interactions. Part 4. Model studies with caffeine and cyclodextrins. J. Chem. Soc. Perkin Trans. 2, 1990, 2197-2209.
54. Pripp, A. H., Vreeker, R., van Duynhoven, J., Binding of olive oil phenolics to food proteins. J. Sci. Food Agric. 2005, 85, 354-362.
55. Bartolomé, B., Estrella, I., Hernández, M. T., Interaction of low molecular weight phenolics with proteins (BSA). J. Food Sci. 2000, 65, 617-621.
56. Luck, G., Liao, H., Murray, N. J., Grimmer, H. R., Warminski, E. E., Williamson, M. P., Lilley, T. H., Haslam, E., Polyphenols, astringency and proline-rich proteins. Phytochemistry 1994, 37, 357-371.