Sensorial properties of red wine polyphenols: Astringency and bitterness

Critical Reviews in Food Science and Nutrition

Volumn 57, Issue 5, 2017, Pages 937-948

  Soares, Susana ^a   Brandão, Elsa ^a   Mateus, Nuno ^a   de Freitas, Victor ^a  

^a UNIVERSITY OF PORTO   (Portugal)

Author keywords

Bitter taste receptors; proline rich proteins; salivary proteins; tannins

Indexed keywords

PROTEINS; TANNINS;

ALZHEIMER'S; CHEMOPREVENTION; MOLECULAR LEVELS; NUTRACEUTICALS; PROLINE-RICH PROTEINS; SALIVARY PROTEINS; SENSORIAL PROPERTIES; TASTE RECEPTORS;

NEURODEGENERATIVE DISEASES;

CARBOHYDRATE DIET; FLAVONOID; POLYPHENOL; PROTEIN INTAKE; SALIVA PROTEIN; TANNIN DERIVATIVE;

ANALYSIS; CARBOHYDRATE DIET; CHEMISTRY; HUMAN; METABOLISM; PROTEIN INTAKE; SALIVA; TASTE; WINE;

DIETARY CARBOHYDRATES; DIETARY PROTEINS; FLAVONOIDS; HUMANS; POLYPHENOLS; SALIVA; SALIVARY PROTEINS AND PEPTIDES; TANNINS; TASTE; WINE;

EID: 85007351784     PISSN: 10408398     EISSN: 15497852     Source Type: Journal    
DOI: 10.1080/10408398.2014.946468     Document Type: Article

References (92)

1. Arts, M. J. T. J., Haenen, G. R. M. M., Wilms, L. C., Beetstra, S. a. J. N., Heijnen, C. G. M., Voss, H.-P., and Bast, A., (2002). Interactions between flavonoids and proteins:Effect on the total antioxidant capacity. J. Agric. Food Chem. 50:1184–1187.
2. Bacon, J. R., and Rhodes, M. J. C., (1998). Development of a competition assay for the evaluation of the binding of human parotid salivary proteins to dietary complex phenols and tannins using a peroxidase-labeled tannin. J. Agric. Food Chem. 46:5083–5088.
3. Bate-Smith, E. C., (1954). Astringency in foods. Food 23:124.
4. Baxter, N. J., Lilley, T. H., Haslam, E., and Williamson, M. P., (1997). Multiple interactions between polyphenols and a salivary proline-rich protein repeat result in complexation and precipitation. Biochemistry 36:5566–5577.
5. Behrens, M., and Meyerhof, W., (2011). Gustatory and extragustatory functions of mammalian taste receptors. Physiol. Behav. 105:4–13.
6. Bennick, A., (1982). Salivary proline-rich proteins. Mol. Cell. Biochem. 45:83–99.
7. Boselli, E., Boulton, R. B., Thorngate, J. H., and Frega, N. G., (2004). Chemical and sensory characterization of DOC red wines from marche (Italy) related to vintage and grape cultivars. J. Agric. Food Chem. 52:3843–3854.
8. Brossaud, F., Cheynier, V., and Noble, A. C., (2001). Bitterness and astringency of grape and wine polyphenols. Aust. J. Grape Wine R. 7:33–39.
9. Cala, O., Dufourc, E. J., Fouquet, E., Manigand, C., Laguerre, M., and Pianet, I., (2012). The colloidal state of tannins impacts the nature of their interaction with proteins:The case of salivary proline-rich protein/procyanidins binding. Langmuir 28:17410–17418.
10. Canon, F., Ballivian, R., Chirot, F., Antoine, R., Sarni-Manchado, P., Lemoine, J. R. M., and Dugourd, P., (2011). Folding of a salivary intrinsically disordered protein upon binding to tannins. J. Am. Chem. Soc. 133:7847–7852.
11. Canon, F., Giuliani, A., Paté, F., and Sarni-Manchado, P., (2010). Ability of a salivary intrinsically unstructured protein to bind different tannin targets revealed by mass spectrometry. Anal. Bioanal. Chem. 398:815–822.
12. Canon, F., Paté, F., Cheynier, V., Sarni-Manchado, P., Giuliani, A., Pérez, J., Durand, D., Li, J., and Cabane, B., (2013). Aggregation of the salivary proline-rich protein IB5 in the presence of the tannin EgCG. Langmuir 29:1926–1937.
13. Carvalho, E., Mateus, N., Plet, B., Pianet, I., Dufourc, E., and De Freitas, V., (2006a). Influence of wine pectic polysaccharides on the interactions between condensed tannins and salivary proteins. J. Agric. Food Chem. 54:8936–8944.
14. Carvalho, E., Póvoas, M. J., Mateus, N., and De Freitas, V., (2006b). Application of flow nephelometry to the analysis of the influence of carbohydrates on protein-tannin interactions. J. Sci. Food Agric. 86:891–896.
15. Castagnola, M., Cabras, T., Vitali, A., Sanna, M. T., and Messana, I., (2011). Biotechnological implications of the salivary proteome. Trends Biotechnol. 29:409–418.
16. Condelli, N., Dinnella, C., Cerone, A., Monteleone, E., and Bertuccioli, M., (2006). Prediction of perceived astringency induced by phenolic compounds II:Criteria for panel selection and preliminary application on wine samples. Food Qual. Prefer. 17:96–107.
17. De Freitas, V., Carvalho, E., and Mateus, N., (2003). Study of carbohydrate influence on protein-tannin aggregation by nephelometry. Food Chem. 81:503–509.
18. De Freitas, V., and Mateus, N., (2001). Structural features of procyanidin interactions with salivary proteins. J. Agric. Food Chem. 49:940–945.
19. De Freitas, V., and Mateus, N., (2002). Nephelometric study of salivary protein-tannin aggregates. J. Sci. Food Agric. 82:113–119.
20. De La Iglesia, R., Milagro, F. I., Campión, J., Boqué, N., and Martínez, J. A., (2010). Healthy properties of proanthocyanidins. BioFactors 36:159–168.
21. Diniz, A., Escuder-Gilabert, L., Lopes, N., Villanueva-Camañas, R., Sagrado, S., and Medina-Hernández, M., (2008). Characterization of interactions between polyphenolic compounds and human serum proteins by capillary electrophoresis. Anal. Bioanal. Chem. 391:625–632.
22. Dinnella, C., Recchia, A., Fia, G., Bertuccioli, M., and Monteleone, E., (2009). Saliva characteristics and individual sensitivity to phenolic astringent stimuli. Chem. Senses 34:295–304.
23. Dinnella, C., Recchia, A., Vincenzi, S., Tuorila, H., and Monteleone, E., (2010). Temporary modification of salivary protein profile and individual responses to repeated phenolic astringent stimuli. Chem. Senses 35:75–85.
24. Doco, T., Williams, P., Moutounet, M., and Pellerin, P., (2000). Les polysaccharides du vin. Bull. OIV 73:785–792.
25. Douglas, W. H., Reeh, E. S., Ramasubbu, N., Raj, P. A., Bhandary, K. K., and Levine, M. J., (1991). Statherin:A major boundary lubricant of human saliva. Biochem. Biophys. Res. Commun. 180:91–97.
26. Drayna, D., (2005). Human taste genetics. Annu. Rev. Genomics Hum. Genet. 6:217–235.
27. Edgar, W. M., (1990). Saliva and dental health. Clinical implications of saliva:Report of a consensus meeting. Br. Dent. J. 169:96–98.
28. Fernandes, A., Ivanova, G., Brás, N. F., Mateus, N., Ramos, M. J., Rangel, M., and De Freitas, V., (2014). Structural characterization of inclusion complexes between cyanidin-3-o-glucoside and β-cyclodextrin. Carbohydr. Polym. 102:269–277.
29. Fischer, U., Boulton, R. B., and Noble, A. C., (1994). Physiological factors contributing to the variability of sensory assessments:Relationship between salivary flow rate and temporal perception of gustatory stimuli. Food Qual. Prefer. 5:55–64.
30. Fulcrand, H., Dueñas, M., Salas, E., and Cheynier, V., (2006). Phenolic reactions during winemaking and aging. Am. J. Enol. Vitic. 57:289–297.
31. Gaffney, S. H., Martin, R., Lilley, T. H., Haslam, E., and Magnolato, D., (1986). The association of polyphenols with caffeine and a- and b-cyclodextrin in aqueous media. Chem. Commun. 107–109.
32. Gawel, R., Oberholster, A., and Francis, I. L., (2000). A ‘mouth-feel wheel’:Terminology for communicating the mouth-feel characteristics of red wine. Aust. J. Grape Wine R. 6:203–207.
33. Hagerman, A. E., and Butler, L. G., (1981). The specificity of proanthocyanidin-protein interactions. J. Biol. Chem. 256:4494–4497.
34. Haslam, E. C., (1998). Maturation - changes in astringency. In:Pratical polyphenolics:From structure to molecular recognition and physiological action. pp. Cambridge University Press.
35. Hufnagel, J. C., and Hofmann, T., (2008). Quantitative reconstruction of the nonvolatile sensometabolome of a red wine. J. Agric. Food Chem. 56:9190–9199.
36. Ji, M., Su, X., Su, X., Chen, Y., Huang, W., Zhang, J., Gao, Z., Li, C., and Lu, X., (2014). Identification of novel compounds for human bitter taste receptors. Chem. Biol. Drug Des.
37. Jobstl, E., O'connell, J., Fairclough, J. P. A., and Williamson, M. P., (2004). Molecular model for astringency produced by polyphenol/protein interactions. Biomacromolecules 5:942–949.
38. Jullian, C., Miranda, S., Zapata-Torres, G., Mendizábal, F., and Olea-Azar, C., (2007). Studies of inclusion complexes of natural and modified cyclodextrin with (+)-catechin by NMR and molecular modeling. Bioorg. Med. Chem. 15:3217–3224.
39. Kallithraka, S., Bakker, J., and Clifford, M. N., (1998). Evidence that salivary proteins are involved in astringency. J. Sens. Stud. 13:29–43.
40. Kawamoto, H., Nakatsubo, F., and Murakami, K., (1995). Quantitative determination of tannin and protein in the precipitates by high-performance liquid-chromatography. Phytochemistry 40:1503–1505.
41. Kennedy, J. A., (2008). Grape and wine phenolics:Observations and recent findings. Cien. Inv. Agr. 35:107–120.
42. Kennedy, J. A., Ferrier, J., Harbertson, J. F., and Des Gachons, C. P., (2006a). Analysis of tannins in red wine using multiple methods:Correlation with perceived astringency. Am. J. Enol. Vitic. 57:481–485.
43. Kennedy, J. A., Saucier, C., and Glories, Y., (2006b). Grape and wine phenolics:History and perspective. Am. J. Enol. Vitic. 57:239–248.
44. Kim, U., Wooding, S., Ricci, D., Jorde, L. B., and Drayna, D., (2005). Worldwide haplotype diversity and coding sequence variation at human bitter taste receptor loci. Hum. Mutat. 26:199–204.
45. Kohl, S., Behrens, M., Dunkel, A., Hofmann, T., and Meyerhof, W., (2013). Amino acids and peptides activate at least five members of the human bitter taste receptor family. J. Agric. Food Chem. 61:53–60.
46. Lee, C. A., and Vickers, Z. M., (2012). Astringency of foods may not be directly related to salivary lubricity. J. Food Sci. 77:S302–S306.
47. Llaudy, M. C., Canals, R., Canals, J. M., Rozes, N., Arola, L., and Zamora, F., (2004). New method for evaluating astringency in red wine. J. Agric. Food Chem. 52:742–746.
48. Luck, G., Liao, H., Murray, N. J., Grimmer, H. R., Warminski, E. E., Williamson, M. P., Lilley, T. H., and Haslam, E., (1994). Polyphenols, astringency and proline-rich proteins. Phytochemistry 37:357–371.
49. Mateus, N., Carvalho, E., Luís, C., and De Freitas, V., (2004). Influence of the tannin structure on the disruption effect of carbohydrates on protein-tannin aggregates. Anal. Chim. Acta 513:135–140.
50. Mercurio, M. D., Dambergs, R. G., Cozzolino, D., Herderich, M. J., and Smith, P. A., (2010). Relationship between red wine grades and phenolics. 1. Tannin and total phenolics concentrations. J. Agric. Food Chem. 58:12313–12319.
51. Morice, A. H., Bennett, R. T., Chaudhry, M. A., Cowen, M. E., Griffin, S. C., and Loubani, M., (2011). Effect of bitter tastants on human bronchi. Nat. Med. 17:775.
52. Noble, A. C., (1990). Bitterness and astringency in wine. In:Bitterness in foods and beverages, pp. 145–158. Elsevier. Amsterdam.
53. Obreque-Slier, E., López-Solís, R., Peña-Neira, Á., and Zamora-Marín, F., (2010). Tannin–protein interaction is more closely associated with astringency than tannin–protein precipitation:Experience with two oenological tannins and a gelatin. Int. J. Food Sci. Technol. 45:2629–2636.
54. Oppenheim, F. G., Xu, T., Mcmillian, F. M., Levitz, S. M., Diamond, R. D., Offner, G. D., and Troxler, R. F., (1988). Histatins, a novel family of histidine-rich proteins in human parotid secretion. Isolation, characterization, primary structure, and fungistatic effects on Candida albicans. J. Biol. Chem. 263:7472–7477.
55. Ozawa, T., Lilley, T. H., and Haslam, E., (1987). Polyphenol interactions:Astringency and the loss of astringency in ripening fruit. Phytochemistry 26:2937–2942.
56. Payne, C., Bowyer, P. K., Herderich, M., and Bastian, S. E. P., (2009). Interaction of astringent grape seed procyanidins with oral epithelial cells. Food Chem. 115:551–557.
57. Peleg, H., Gacon, K., Schlich, P., and Noble, A. C., (1999). Bitterness and astringency of flavan-3-ol monomers, dimers and trimers. J. Sci. Food Agric. 79:1123–1128.
58. Prieur, C., Rigaud, J., Cheynier, V., and Moutounet, M., (1994). Oligomeric and polymeric procyanidins from grape seeds. Phytochemistry 36:781–784.
59. Pronin, A. N., Tang, H., Connor, J., and Keung, W., (2004). Identification of ligands for two human bitter T2R receptors. Chem. Senses 29:583–593.
60. Quijada-Morín, N., Regueiro, J., Simal-Gándara, J., Tomás, E., Rivas-Gonzalo, J. C., and Escribano-Bailón, M. T., (2012). Relationship between the sensory-determined astringency and the flavanolic composition of red wines. J. Agric. Food Chem. 60:12355–12361.
61. Quijada-Morín, N., Williams, P., Rivas-Gonzalo, J. C., Doco, T., and Escribano-Bailón, M. T., (2014). Polyphenolic, polysaccharide and oligosaccharide composition of tempranillo red wines and their relationship with the perceived astringency. Food Chem. 154:44–51.
62. Ramassamy, C., (2006). Emerging role of polyphenolic compounds in the treatment of neurodegenerative diseases:A review of their intracellular targets. Eur. J. Pharmacol. 545:51–64.
63. Renaud, S., and De Lorgeril, M., (1992). Wine, alcohol, platelets, and the French paradox for coronary heart disease. The Lancet 339:1523–1526.
64. Ricardo-Da-Silva, J. M., Cheynier, V., Souquet, J.-M., Moutounet, M., Cabanis, J.-C., and Bourzeix, M., (1991). Interaction of grape seed procyanidins with various proteins in relation to wine fining. J. Sci. Food Agric. 57:111–125.
65. Richard, T., Vitrac, X., Merillon, J. M., and Monti, J. P., (2005). Role of peptide primary sequence in polyphenol-protein recognition:An example with neurotensin. Biochim. Biophys. Acta—General Subjects 1726:238–243.
66. Rinaldi, A., Gambuti, A., and Moio, L., (2012). Application of the SPI (saliva precipitation index) to the evaluation of red wine astringency. Food Chem. 135:2498–2504.
67. Robichaud, J. L., and Noble, A. C., (1990). Astringency and bitterness of selected phenolics in wine. J. Sci. Food Agric. 52:343–353.
68. Roland, W. S. U., Van Buren, L., Gruppen, H., Driesse, M., Gouka, R. J., Smit, G., and Vincken, J.-P., (2013). Bitter taste receptor activation by flavonoids and isoflavonoids:Modeled structural requirements for activation of hTAS2R14 and hTAS2R39. J. Agric. Food Chem. 61:10454–10466.
69. Roland, W. S. U., Vincken, J.-P., Gouka, R. J., Van Buren, L., Gruppen, H., and Smit, G., (2011). Soy isoflavones and other isoflavonoids activate the human bitter taste receptors hTAS2R14 and hTAS2R39. J. Agric. Food Chem. 59:11764–11771.
70. Rossetti, D., Bongaerts, J. H. H., Wantling, E., Stokes, J. R., and Williamson, A. M., (2009). Astringency of tea catechins:More than an oral lubrication tactile percept. Food Hydrocolloids 23:1984–1992.
71. Rossetti, D., Yakubov, G. E., Stokes, J. R., Williamson, A. M., and Fuller, G. G., (2008). Interaction of human whole saliva and astringent dietary compounds investigated by interfacial shear rheology. Food Hydrocolloids 22:1068–1078.
72. Sarneckis, C. J., Dambergs, R. G., Jones, P., Mercurio, M., Herderich, M. J., and Smith, P. A., (2006). Quantification of condensed tannins by precipitation with methyl cellulose:Development and validation of an optimised tool for grape and wine analysis. Aust. J. Grape Wine R. 12:39–49.
73. Sarni-Manchado, P., Canals-Bosch, J. M., Mazerolles, G., and Cheynier, V., (2008). Influence of the glycosylation of human salivary proline-rich proteins on their interactions with condensed tannins. J. Agric. Food Chem. 56:9563–9569.
74. Sarni-Manchado, P., Cheynier, V., and Moutounet, M., (1999). Interactions of grape seed tannins with salivary proteins. J. Agric. Food Chem. 47:42–47.
75. Scharbert, S., Holzmann, N., and Hofmann, T., (2004). Identification of the astringent taste compounds in black tea infusions by combining instrumental analysis and human bioresponse. J. Agric. Food Chem. 52:3498–3508.
76. Schwarz, B., and Hofmann, T., (2008). Is there a direct relationship between oral astringency and human salivary protein binding? Eur. Food Res. Technol. 227:1693–1698.
77. Soares, S., Kohl, S., Thalmann, S., Mateus, N., Meyerhof, W., and De Freitas, V., (2013). Different phenolic compounds activate distinct human bitter taste receptors. J. Agric. Food Chem. 61:1525–1533.
78. Soares, S., Mateus, N., and De Freitas, V., (2007). Interaction of different polyphenols with bovine serum albumin (BSA) and human salivary a-amylase (HSA) by fluorescence quenching. J. Agric. Food Chem. 55:6726–6735.
79. Soares, S., Mateus, N., and De Freitas, V., (2012). Carbohydrates inhibit salivary proteins precipitation by condensed tannins. J. Agric. Food Chem. 60:3966–3972.
80. Soares, S., Sousa, A., Mateus, N., and De Freitas, V., (2011a). Effect of condensed tannins addition on the astringency of red wines. Chem. Senses.
81. Soares, S., Vitorino, R., OsóRio, H., Fernandes, A., Venâncio, A., Mateus, N., Amado, F., and De Freitas, V., (2011b). Reactivity of human salivary proteins families toward food polyphenols. J. Agric. Food Chem. 59:5535–5547.
82. Soares, S. I., Gonçalves, R. M., Fernandes, I., Mateus, N., and De Freitas, V., (2009). Mechanistic approach by which polysaccharides inhibit a-amylase/procyanidin aggregation. J. Agric. Food Chem. 57:4352–4358.
83. Souquet, J. M., Cheynier, V., Brossaud, F., and Moutounet, M., (1996). Polymeric proanthocyanidins from grape skins. Phytochemistry 43:509–512.
84. Sun, B., Sá, M. D., Leandro, C., Caldeira, I., Duarte, F. L., and Spranger, I., (2013). Reactivity of polymeric proanthocyanidins toward salivary proteins and their contribution to young red wine astringency. J. Agric. Food Chem. 61:939–946.
85. Troxler, R. F., Offner, G. D., Xu, T., Vanderspek, J. C., and Oppenheim, F. G., (1990). Structural relationship between human salivary histatins. J. Dent. Res. 69:2–6.
86. Vidal, S., Courcoux, P., Francis, L., Kwiatkowski, M., Gawel, R., Williams, P., Waters, E., and Cheynier, V., (2004a). Use of an experimental design approach for evaluation of key wine components on mouth-feel perception. Food Qual. Prefer. 15:209–217.
87. Vidal, S., Francis, L., Guyot, S., Marnet, N., Kwiatkowski, M., Gawel, R., Cheynier, V., and Waters, E. J., (2003). The mouth-feel properties of grape and apple proanthocyanidins in a wine-like medium. J. Sci. Food Agric. 83:564–573.
88. Vidal, S., Francis, L., Noble, A., Kwiatkowski, M., Cheynier, V., and Waters, E., (2004b). Taste and mouth-feel properties of different types of tannin-like polyphenolic compounds and anthocyanins in wine. Anal. Chim. Acta 513:57–65.
89. Vidal, S., Francis, L., Williams, P., Kwiatkowski, M., Gawel, R., Cheynier, V., and Waters, E., (2004). The mouth-feel properties of polysaccharides and anthocyanins in a wine like medium. Food Chem. 85:519–525.
90. Wroblewski, K., Muhandiram, R., Chakrabartty, A., and Bennick, A., (2001). The molecular interaction of human salivary histatins with polyphenolic compounds. Eur. J. Biochem. 268:4384–4397.
91. Xiao, J., and Kai, G., (2012). A review of dietary polyphenol-plasma protein interactions:Characterization, influence on the bioactivity, and structure-affinity relationship. Crit. Rev. Food Sci. Nutr. 52:85–101.
92. Yu, P., Yeo, A. S.-L., Low, M.-Y., and Zhou, W., (2014). Identifying key non-volatile compounds in ready-to-drink green tea and their impact on taste profile. Food Chem. 155:9–16.