ACS Publications. Most Trusted. Most Cited. Most Read
My Activity

Multiple Interactions between Polyphenols and a Salivary Proline-Rich Protein Repeat Result in Complexation and Precipitation

View Author Information
Department of Molecular Biology and Biotechnology, The Krebs Institute for Biomolecular Research, University of Sheffield, Sheffield S10 2TN, U.K., and Department of Chemistry, The Krebs Institute for Biomolecular Research, University of Sheffield, Sheffield S3 7HF, U.K.
Cite this: Biochemistry 1997, 36, 18, 5566–5577
Publication Date (Web):May 6, 1997
Copyright © 1997 American Chemical Society

    Article Views





    Other access options
    Supporting Info (1)»


    Polyphenols (tannins) in the diet not only precipitate oral proteins, producing an astringent sensation, but also interact with dietary proteins and digestive enzymes in the gut, resulting in a variety of antinutritive and toxic effects. Salivary proline-rich proteins (PRPs), which are secreted into the oral cavity, form complexes with and precipitate dietary polyphenols, and thus, they constitute the primary mammalian defense directed against ingested tannins. In order to characterize the interaction, NMR studies were performed which involved titrating a series of polyphenols into a synthetic 19-residue PRP fragment. The results show that the predominant mode of association is a hydrophobic stacking of the polyphenol ring against the pro-S face of proline and that the first proline residue of a Pro-Pro sequence is a particularly favored binding site. Measurement of dissociation constants indicates that the larger and more complex polyphenols interact more strongly with the PRP fragment; the order of binding affinity was determined as procyanidin dimer B-2 > pentagalloylglucose > trigalloylglucose >> proanthocyanidin monomer (−)-epicatechin ≈ propyl gallate. Smaller polyphenols can bind with one phenolic ring stacked against each proline residue, whereas larger polyphenols occupy two or three consecutive prolines. The more complex polyphenols interact with the PRP fragment in a multidentate fashion; moreover, they self-associate or stack when bound. Thus, a model is proposed in which multiple polyphenol/polyphenol and polyphenol/PRP interactions act cooperatively to achieve precipitation.

    Read this article

    To access this article, please review the available access options below.

    Get instant access

    Purchase Access

    Read this article for 48 hours. Check out below using your ACS ID or as a guest.


    Access through Your Institution

    You may have access to this article through your institution.

    Your institution does not have access to this content. You can change your affiliated institution below.

    This research has been supported by the BBSRC and Mars Confectionery Ltd.

     Department of Molecular Biology and Biotechnology.


     Née Murray.

     Department of Chemistry.


    In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

     Abstract published in Advance ACS Abstracts, April 15, 1997.

    Supporting Information Available

    Jump To

    Tables of the chemical shift data obtained during the peptide/polyphenol titrations and the polyphenol self-association experiments (30 pages). Ordering information is given on any current masthead page.

    Terms & Conditions

    Most electronic Supporting Information files are available without a subscription to ACS Web Editions. Such files may be downloaded by article for research use (if there is a public use license linked to the relevant article, that license may permit other uses). Permission may be obtained from ACS for other uses through requests via the RightsLink permission system:

    Cited By

    This article is cited by 554 publications.

    1. Zhouying Luo, Yang He, Ming Li, Yumeng Ge, Yisha Huang, Xia Liu, Jianwen Hou, Shaobing Zhou. Tumor Microenvironment-Inspired Glutathione-Responsive Three-Dimensional Fibrous Network for Efficient Trapping and Gentle Release of Circulating Tumor Cells. ACS Applied Materials & Interfaces 2023, 15 (20) , 24013-24022.
    2. Mónica de Jesus, Carlos Guerreiro, Elsa Brandão, Nuno Mateus, Victor de Freitas, Susana Soares. Study of Serial Exposures of an Astringent Green Tea Flavonoid Extract with Oral Cell-Based Models. Journal of Agricultural and Food Chemistry 2023, 71 (4) , 2070-2081.
    3. Zhaomeng Wang, Yanhua Liu, Shuo Li, Fanlin Meng, Jiang Yu, Shuang Zhou, Songtao Dong, Jianying Ye, Lingxiao Li, Chuang Zhang, Shengnan Qiu, Guimei Lin, Hongzhuo Liu, Shyh-Dar Li, Zhonggui He, Yongjun Wang. Bioinspired Nanocomplexes Comprising Phenolic Acid Derivative and Human Serum Albumin for Cancer Therapy. Nano Letters 2022, 22 (24) , 10040-10048.
    4. A. M. Ramos-Pineda, E. Manjón, R. I. R. Macías, I. García-Estévez, M. T. Escribano-Bailón. Role of Yeast Mannoproteins in the Interaction between Salivary Proteins and Flavan-3-ols in a Cell-Based Model of the Oral Epithelium. Journal of Agricultural and Food Chemistry 2022, 70 (41) , 13027-13035.
    5. Marica T. Engström, Valtteri Virtanen, Juha-Pekka Salminen. Influence of the Hydrolyzable Tannin Structure on the Characteristics of Insoluble Hydrolyzable Tannin–Protein Complexes. Journal of Agricultural and Food Chemistry 2022, 70 (41) , 13036-13048.
    6. Yike Jiang, Ting Zheng, Weiping Jin, Yuxin Shi, Qingrong Huang. Enhancing Intestinal Permeability of Theaflavin-3,3′-digallate by Chitosan–Caseinophosphopeptides Nanocomplexes. Journal of Agricultural and Food Chemistry 2022, 70 (6) , 2029-2041.
    7. Wendell Albuquerque, Leif Seidel, Holger Zorn, Frank Will, Martin Gand. Haze Formation and the Challenges for Peptidases in Wine Protein Fining. Journal of Agricultural and Food Chemistry 2021, 69 (48) , 14402-14414.
    8. Elvira Manjón, Natércia F. Brás, Ignacio García-Estévez, M. Teresa Escribano-Bailón. Cell Wall Mannoproteins from Yeast Affect Salivary Protein–Flavanol Interactions through Different Molecular Mechanisms. Journal of Agricultural and Food Chemistry 2020, 68 (47) , 13459-13468.
    9. Renaud Miclette Lamarche, Christine DeWolf. ω-Thiolation of Phenolic Surfactants Enables Controlled Conversion between Extended, Bolaform, and Multilayer Conformations. Langmuir 2020, 36 (11) , 2847-2857.
    10. A. M. Ramos-Pineda, G. H. Carpenter, I. García-Estévez, M. T. Escribano-Bailón. Influence of Chemical Species on Polyphenol–Protein Interactions Related to Wine Astringency. Journal of Agricultural and Food Chemistry 2020, 68 (10) , 2948-2954.
    11. Silvia Molino, Natalia Andrea Casanova, José Ángel Rufián Henares, Mariano Enrique Fernandez Miyakawa. Natural Tannin Wood Extracts as a Potential Food Ingredient in the Food Industry. Journal of Agricultural and Food Chemistry 2020, 68 (10) , 2836-2848.
    12. Wayne E. Zeller, Laurie A. Reinhardt, Jamison T. Robe, Michael L. Sullivan, Kevin Panke-Buisse. Comparison of Protein Precipitation Ability of Structurally Diverse Procyanidin-Rich Condensed Tannins in Two Buffer Systems. Journal of Agricultural and Food Chemistry 2020, 68 (7) , 2016-2023.
    13. Renaud Miclette Lamarche, Christine DeWolf. Strong Headgroup Interactions Drive Highly Directional Growth and Unusual Phase Co-Existence in Self-Assembled Phenolic Films. ACS Applied Materials & Interfaces 2019, 11 (48) , 45354-45363.
    14. Junling Guo, Tomoya Suma, Joseph J. Richardson, Hirotaka Ejima. Modular Assembly of Biomaterials Using Polyphenols as Building Blocks. ACS Biomaterials Science & Engineering 2019, 5 (11) , 5578-5596.
    15. Leping Wu, Hui Shao, Zehui Fang, Yuancong Zhao, Chris Ying Cao, Quanli Li. Mechanism and Effects of Polyphenol Derivatives for Modifying Collagen. ACS Biomaterials Science & Engineering 2019, 5 (9) , 4272-4284.
    16. M. T. Engström, J. Arvola, S. Nenonen, V. T. J. Virtanen, M. M. Leppä, P. Tähtinen, J. -P. Salminen. Structural Features of Hydrolyzable Tannins Determine Their Ability to Form Insoluble Complexes with Bovine Serum Albumin. Journal of Agricultural and Food Chemistry 2019, 67 (24) , 6798-6808.
    17. Sinem Ulusan, Vural Bütün, Sreeparna Banerjee, Irem Erel-Goktepe. Biologically Functional Ultrathin Films Made of Zwitterionic Block Copolymer Micelles. Langmuir 2019, 35 (5) , 1156-1171.
    18. Karl R. Oleson, Kayla G. Sprenger, Jim Pfaendtner, Daniel T. Schwartz. Inhibition of the Exoglucanase Cel7A by a Douglas-Fir-Condensed Tannin. The Journal of Physical Chemistry B 2018, 122 (37) , 8665-8674.
    19. Mélodie Gil, Fabian Avila-Salas, Leonardo S. Santos, Nerea Iturmendi, Virginie Moine, Véronique Cheynier, and Cédric Saucier . Rosé Wine Fining Using Polyvinylpolypyrrolidone: Colorimetry, Targeted Polyphenomics, and Molecular Dynamics Simulations. Journal of Agricultural and Food Chemistry 2017, 65 (48) , 10591-10597.
    20. M. D. Teli and Pintu Pandit . Novel Method of Ecofriendly Single Bath Dyeing and Functional Finishing of Wool Protein with Coconut Shell Extract Biomolecules. ACS Sustainable Chemistry & Engineering 2017, 5 (9) , 8323-8333.
    21. Alba María Ramos-Pineda, Ignacio García-Estévez, Natércia F. Brás, Eva M. Martín del Valle, Montserrat Dueñas, and María Teresa Escribano Bailón . Molecular Approach to the Synergistic Effect on Astringency Elicited by Mixtures of Flavanols. Journal of Agricultural and Food Chemistry 2017, 65 (31) , 6425-6433.
    22. Mafalda Santos Silva, Ignacio García-Estévez, Elsa Brandão, Nuno Mateus, Victor de Freitas, and Susana Soares . Molecular Interaction Between Salivary Proteins and Food Tannins. Journal of Agricultural and Food Chemistry 2017, 65 (31) , 6415-6424.
    23. Judith Delius, Guillaume Médard, Bernhard Kuster, and Thomas Hofmann . Effect of Astringent Stimuli on Salivary Protein Interactions Elucidated by Complementary Proteomics Approaches. Journal of Agricultural and Food Chemistry 2017, 65 (10) , 2147-2154.
    24. Benoit Faurie, Erick J. Dufourc, Michel Laguerre, and Isabelle Pianet . Monitoring the Interactions of a Ternary Complex Using NMR Spectroscopy: The Case of Sugars, Polyphenols, and Proteins. Analytical Chemistry 2016, 88 (24) , 12470-12478.
    25. Susana Soares, Raúl Ferrer-Galego, Elsa Brandão, Mafalda Silva, Nuno Mateus, and Victor de Freitas . Contribution of Human Oral Cells to Astringency by Binding Salivary Protein/Tannin Complexes. Journal of Agricultural and Food Chemistry 2016, 64 (41) , 7823-7828.
    26. Jacqui M. McRae, Zyta M. Ziora, Stella Kassara, Matthew A. Cooper, and Paul A. Smith . Ethanol Concentration Influences the Mechanisms of Wine Tannin Interactions with Poly(l-proline) in Model Wine. Journal of Agricultural and Food Chemistry 2015, 63 (17) , 4345-4352.
    27. Cristina M. P. Vidal, Ariene A. Leme, Thaiane R. Aguiar, Rasika Phansalkar, Joo-Won Nam, Jonathan Bisson, James B. McAlpine, Shao-Nong Chen, Guido F. Pauli, and Ana Bedran-Russo . Mimicking the Hierarchical Functions of Dentin Collagen Cross-Links with Plant Derived Phenols and Phenolic Acids. Langmuir 2014, 30 (49) , 14887-14893.
    28. Clotilde Hue, Pierre Brat, Ziya Gunata, Ivan Samaniego, Adrien Servent, Gilles Morel, André Kapitan, Renaud Boulanger, and Fabrice Davrieux . Near Infra-red Characterization of Changes in Flavan-3-ol Derivatives in Cocoa (Theobroma cacao L.) as a Function of Fermentation Temperature. Journal of Agricultural and Food Chemistry 2014, 62 (41) , 10136-10142.
    29. Bei Wang, Tuuli Koivumäki, Petri Kylli, Marina Heinonen, and Marjo Poutanen . Protein–Phenolic Interaction of Tryptic Digests of β-Lactoglobulin and Cloudberry Ellagitannin. Journal of Agricultural and Food Chemistry 2014, 62 (22) , 5028-5037.
    30. Jing Zhao, Fusheng Pan, Pan Li, Cuihong Zhao, Zhongyi Jiang, Peng Zhang, and Xingzhong Cao . Fabrication of Ultrathin Membrane via Layer-by-Layer Self-assembly Driven by Hydrophobic Interaction Towards High Separation Performance. ACS Applied Materials & Interfaces 2013, 5 (24) , 13275-13283.
    31. Nadin Al Shukor, John Van Camp, Gerard Bryan Gonzales, Dorien Staljanssens, Karin Struijs, Moises J. Zotti, Katleen Raes, and Guy Smagghe . Angiotensin-Converting Enzyme Inhibitory Effects by Plant Phenolic Compounds: A Study of Structure Activity Relationships. Journal of Agricultural and Food Chemistry 2013, 61 (48) , 11832-11839.
    32. Jon S. Hansen, Mario Ficker, Johannes F. Petersen, Bjarne E. Nielsen, Saira Gohar, and Jørn B. Christensen . Study of the Complexation of Oxacillin in 1-(4-Carbomethoxypyrrolidone)-Terminated PAMAM Dendrimers. The Journal of Physical Chemistry B 2013, 117 (47) , 14865-14874.
    33. Jennifer A. Barak and James A. Kennedy . HPLC Retention Thermodynamics of Grape and Wine Tannins. Journal of Agricultural and Food Chemistry 2013, 61 (18) , 4270-4277.
    34. Neal J. Zondlo . Aromatic–Proline Interactions: Electronically Tunable CH/π Interactions. Accounts of Chemical Research 2013, 46 (4) , 1039-1049.
    35. Jie Yin, Mogens L. Andersen, and Leif H. Skibsted . Reduction of Ferrylmyoglobin by Theanine and Green Tea Catechins. Importance of Specific Acid Catalysis. Journal of Agricultural and Food Chemistry 2013, 61 (12) , 3159-3166.
    36. Aude A. Watrelot, Carine Le Bourvellec, Anne Imberty, and Catherine M. G. C. Renard . Interactions between Pectic Compounds and Procyanidins are Influenced by Methylation Degree and Chain Length. Biomacromolecules 2013, 14 (3) , 709-718.
    37. Francis Canon, Franck Paté, Véronique Cheynier, Pascale Sarni-Manchado, Alexandre Giuliani, Javier Pérez, Dominique Durand, Joaquim Li, and Bernard Cabane . Aggregation of the Salivary Proline-Rich Protein IB5 in the Presence of the Tannin EgCG. Langmuir 2013, 29 (6) , 1926-1937.
    38. Baoshan Sun, Marta de Sá, Conceição Leandro, Ilda Caldeira, Filomena L. Duarte, and Isabel Spranger . Reactivity of Polymeric Proanthocyanidins toward Salivary Proteins and Their Contribution to Young Red Wine Astringency. Journal of Agricultural and Food Chemistry 2013, 61 (4) , 939-946.
    39. Natalia Quijada-Morín, Jorge Regueiro, Jesús Simal-Gándara, Esperanza Tomás, Julián C. Rivas-Gonzalo, and M. Teresa Escribano-Bailón . Relationship between the Sensory-Determined Astringency and the Flavanolic Composition of Red Wines. Journal of Agricultural and Food Chemistry 2012, 60 (50) , 12355-12361.
    40. Olivier Cala, Erick J. Dufourc, Eric Fouquet, Claude Manigand, Michel Laguerre, and Isabelle Pianet . The Colloidal State of Tannins Impacts the Nature of Their Interaction with Proteins: The Case of Salivary Proline-Rich Protein/Procyanidins Binding. Langmuir 2012, 28 (50) , 17410-17418.
    41. Yanyan Zhao, Longjian Chen, Gleb Yakubov, Termeh Aminiafshar, Lujia Han, and Guoping Lian . Experimental and Theoretical Studies on the Binding of Epigallocatechin Gallate to Purified Porcine Gastric Mucin. The Journal of Physical Chemistry B 2012, 116 (43) , 13010-13016.
    42. Carine Le Bourvellec, Aude A. Watrelot, Christian Ginies, Anne Imberty, and Catherine M. G. C. Renard . Impact of Processing on the Noncovalent Interactions between Procyanidin and Apple Cell Wall. Journal of Agricultural and Food Chemistry 2012, 60 (37) , 9484-9494.
    43. Aditya Radhakrishnan, Andreas Vitalis, Albert H. Mao, Adam T. Steffen, and Rohit V. Pappu . Improved Atomistic Monte Carlo Simulations Demonstrate That Poly-l-Proline Adopts Heterogeneous Ensembles of Conformations of Semi-Rigid Segments Interrupted by Kinks. The Journal of Physical Chemistry B 2012, 116 (23) , 6862-6871.
    44. Kunal D. Patel, Frank J. Scarano, Miwako Kondo, Robert A. R. Hurta, and Catherine C. Neto . Proanthocyanidin-rich Extracts from Cranberry Fruit (Vaccinium macrocarpon Ait.) Selectively Inhibit the Growth of Human Pathogenic Fungi Candida spp. and Cryptococcus neoformans. Journal of Agricultural and Food Chemistry 2011, 59 (24) , 12864-12873.
    45. Rui Gonçalves, Nuno Mateus, and Victor De Freitas . Influence of Carbohydrates on the Interaction of Procyanidin B3 with Trypsin. Journal of Agricultural and Food Chemistry 2011, 59 (21) , 11794-11802.
    46. Rui Gonçalves, Nuno Mateus, Isabelle Pianet, Michel Laguerre, and Victor de Freitas . Mechanisms of Tannin-Induced Trypsin Inhibition: A Molecular Approach. Langmuir 2011, 27 (21) , 13122-13129.
    47. Zhen Wu, Jian Ming, Ruiping Gao, Yuxue Wang, Qiang Liang, Huaguang Yu, and Guohua Zhao . Characterization and Antioxidant Activity of the Complex of Tea Polyphenols and Oat β-Glucan. Journal of Agricultural and Food Chemistry 2011, 59 (19) , 10737-10746.
    48. César Vega and Mollie K. Grover . Physicochemical Properties of Acidified Skim Milk Gels Containing Cocoa Flavanols. Journal of Agricultural and Food Chemistry 2011, 59 (12) , 6740-6747.
    49. Zhan-Bo Dong, Yue-Rong Liang, Fang-Yuan Fan, Jian-Hui Ye, Xin-Qiang Zheng, and Jian-Liang Lu . Adsorption Behavior of the Catechins and Caffeine onto Polyvinylpolypyrrolidone. Journal of Agricultural and Food Chemistry 2011, 59 (8) , 4238-4247.
    50. Shahina Naz, Rahmanullah Siddiqi, Tristan P. Dew, and Gary Williamson . Epigallocatechin-3-gallate Inhibits Lactase but Is Alleviated by Salivary Proline-Rich Proteins. Journal of Agricultural and Food Chemistry 2011, 59 (6) , 2734-2738.
    51. Eunice Costa, Margarida Coelho, Laura M. Ilharco, Ana Aguiar-Ricardo, and Paula T. Hammond . Tannic Acid Mediated Suppression of PNIPAAm Microgels Thermoresponsive Behavior. Macromolecules 2011, 44 (3) , 612-621.
    52. Zhen Wu, Hong Li, Jian Ming, and Guohua Zhao . Optimization of Adsorption of Tea Polyphenols into Oat β-Glucan Using Response Surface Methodology. Journal of Agricultural and Food Chemistry 2011, 59 (1) , 378-385.
    53. Maria V. Lomova, Gleb B. Sukhorukov, and Maria N. Antipina . Antioxidant Coating of Micronsize Droplets for Prevention of Lipid Peroxidation in Oil-in-Water Emulsion. ACS Applied Materials & Interfaces 2010, 2 (12) , 3669-3676.
    54. Rui Gonçalves, Nuno Mateus, and Victor de Freitas. Biological Relevance of the Interaction between Procyanidins and Trypsin: A Multitechnique Approach. Journal of Agricultural and Food Chemistry 2010, 58 (22) , 11924-11931.
    55. Tiziana Mariarita Granato, Federico Piano, Antonella Nasi, Pasquale Ferranti, Stefania Iametti, and Francesco Bonomi . Molecular Basis of the Interaction between Proteins of Plant Origin and Proanthocyanidins in a Model Wine System. Journal of Agricultural and Food Chemistry 2010, 58 (22) , 11969-11976.
    56. Natércia F. Brás, Rui Gonçalves, Nuno Mateus, Pedro A. Fernandes, Maria João Ramos, and Victor de Freitas . Inhibition of Pancreatic Elastase by Polyphenolic Compounds. Journal of Agricultural and Food Chemistry 2010, 58 (19) , 10668-10676.
    57. Elías Obreque-Slier, Carolina Mateluna, Álvaro Peña-Neira and Remigio López-Solís . Quantitative Determination of Interactions Between Tannic Acid and a Model Protein Using Diffusion and Precipitation Assays on Cellulose Membranes. Journal of Agricultural and Food Chemistry 2010, 58 (14) , 8375-8379.
    58. Natércia F. Brás, Rui Gonçalves, Pedro A. Fernandes, Nuno Mateus, Maria João Ramos and Victor de Freitas . Understanding the Binding of Procyanidins to Pancreatic Elastase by Experimental and Computational Methods. Biochemistry 2010, 49 (25) , 5097-5108.
    59. Thiranan Kunanopparat, Paul Menut, Marie-Hélène Morel and Stéphane Guilbert. Modification of the Wheat Gluten Network by Kraft Lignin Addition. Journal of Agricultural and Food Chemistry 2009, 57 (18) , 8526-8533.
    60. Tatsiana G. Shutava, Shantanu S. Balkundi, Pranitha Vangala, Joshua J. Steffan, Rebecca L. Bigelow, James A. Cardelli, D. Patrick O’Neal and Yuri M. Lvov . Layer-by-Layer-Coated Gelatin Nanoparticles as a Vehicle for Delivery of Natural Polyphenols. ACS Nano 2009, 3 (7) , 1877-1885.
    61. Indah Epriliati, Bruce D’Arcy and Mike Gidley. Nutriomic Analysis of Fresh and Processed Fruit Products. 2. During in Vitro Simultaneous Molecular Passages Using Caco-2 Cell Monolayers. Journal of Agricultural and Food Chemistry 2009, 57 (8) , 3377-3388.
    62. Pascale Sarni-Manchado, Joan-Miguel Canals-Bosch, Gérard Mazerolles and Véronique Cheynier. Influence of the Glycosylation of Human Salivary Proline-Rich Proteins on Their Interactions with Condensed Tannins. Journal of Agricultural and Food Chemistry 2008, 56 (20) , 9563-9569.
    63. V. Aguié-Béghin, P. Sausse, E. Meudec, V. Cheynier and R. Douillard . Polyphenol−β-Casein Complexes at the Air/Water Interface and in Solution: Effects of Polyphenol Structure. Journal of Agricultural and Food Chemistry 2008, 56 (20) , 9600-9611.
    64. Hanna Salminen and Marina Heinonen. Plant Phenolics Affect Oxidation of Tryptophan. Journal of Agricultural and Food Chemistry 2008, 56 (16) , 7472-7481.
    65. Christine Pascal, Céline Poncet-Legrand, Bernard Cabane and Aude Vernhet . Aggregation of a Proline-Rich Protein Induced by Epigallocatechin Gallate and Condensed Tannins: Effect of Protein Glycosylation. Journal of Agricultural and Food Chemistry 2008, 56 (15) , 6724-6732.
    66. Irem Erel-Unal and Svetlana A. Sukhishvili. Hydrogen-Bonded Multilayers of a Neutral Polymer and a Polyphenol. Macromolecules 2008, 41 (11) , 3962-3970.
    67. Li Liang, H. A. Tajmir-Riahi and Muriel Subirade . Interaction of β-Lactoglobulin with Resveratrol and its Biological Implications. Biomacromolecules 2008, 9 (1) , 50-56.
    68. Giovanna Lomolino and Andrea Curioni. Protein Haze Formation in White Wines: Effect of Saccharomyces cerevisiae Cell Wall Components Prepared with Different Procedures. Journal of Agricultural and Food Chemistry 2007, 55 (21) , 8737-8744.
    69. Céline Poncet-Legrand, Catherine Gautier, Véronique Cheynier and Anne Imberty. Interactions between Flavan-3-ols and Poly(l-proline) Studied by Isothermal Titration Calorimetry: Effect of the Tannin Structure. Journal of Agricultural and Food Chemistry 2007, 55 (22) , 9235-9240.
    70. Tatsiana Shutava,, Malcolm Prouty,, Dinesh Kommireddy, and, Yuri Lvov. pH Responsive Decomposable Layer-by-Layer Nanofilms and Capsules on the Basis of Tannic Acid. Macromolecules 2005, 38 (7) , 2850-2858.
    71. Pascal Sausse,, Véronique Aguié-Béghin, and, Roger Douillard. Effects of Epigallocatechin Gallate on β-Casein Adsorption at the Air/Water Interface. Langmuir 2003, 19 (3) , 737-743.
    72. Clare R. Trevitt, D. R. Yashwanth Kumar, Nicholas J. Fowler, Mike P. Williamson. Interactions between the protein barnase and co-solutes studied by NMR. Communications Chemistry 2024, 7 (1)
    73. Liudis L. Pino-Ramos, Encarna Gómez-Plaza, Verónica R. Olate-Olave, V. Felipe Laurie, Ana Belen Bautista-Ortín. Protein extracts from amaranth and quinoa as novel fining agents for red wines. Food Chemistry 2024, 448 , 139055.
    74. Carlos Guerreiro, Alessandra Rinaldi, Elsa Brandão, Mónica de Jesus, Leonor Gonçalves, Nuno Mateus, Victor de Freitas, Susana Soares. A look upon the adsorption of different astringent agents to oral models: Understanding the contribution of alternative mechanisms in astringency. Food Chemistry 2024, 448 , 139153.
    75. Bushra Bilal, M. Kamran Azim. Nematicidal activity of paucimannose-type glycoconjugates from acacia honey. Experimental Parasitology 2024, 259 , 108707.
    76. Samuel S. Gamaniel, Paloma S. Dueñas Robles, Hans Tromp, Els H. A. de Hoog, Sissi de Beer, Emile van der Heide. A tribo-chemical view on astringency of plant-based food substances. Friction 2024, 36
    77. Remigio López-Solís, Katherine Cortés-Araya, Marcela Medel-Marabolí, Elías Obreque-Slier. Different physicochemical interactions between varietal wines and human saliva: Correspondence with astringency. Food Research International 2024, 178 , 113964.
    78. Mariana Reis‐Havlat, Yvette Alania, Bin Zhou, Shu‐Xi Jing, James B. McAlpine, Shao‐Nong Chen, Guido F. Pauli, Ana K. Bedran‐Russo. Modulatory role of terminal monomeric flavan‐3‐ol units in the viscoelasticity of dentin. Journal of Biomedical Materials Research Part B: Applied Biomaterials 2024, 112 (1)
    79. Elsa Brandão, Mónica Jesus, Carlos Guerreiro, Élia Maricato, Manuel A. Coimbra, Nuno Mateus, Victor de Freitas, Susana Soares. Development of a cell-based quaternary system to unveil the effect of pectic polysaccharides on oral astringency. Carbohydrate Polymers 2024, 323 , 121378.
    80. Xinyu Li, Wenzhen Liu, Gaoliang Wang, Samuel Sai‐Ming Sun, Ling Yuan, Jingxue Wang. Improving digestibility of sorghum proteins by CRISPR /Cas9‐based genome editing. Food and Energy Security 2024, 13 (1)
    81. Yunfeng Li, Yulia Pustovalova, Tzanko I. Doukov, Jeffrey C. Hoch, Richard E. Mains, Betty A. Eipper, Bing Hao. Structure of the Sec14 domain of Kalirin reveals a distinct class of lipid-binding module in RhoGEFs. Nature Communications 2023, 14 (1)
    82. Silvia Molino, M. Pilar Francino, José Ángel Rufián Henares. Why is it important to understand the nature and chemistry of tannins to exploit their potential as nutraceuticals?. Food Research International 2023, 173 , 113329.
    83. Nisrine Jahmidi‐Azizi, Rosario Oliva, Roland Winter. Alcohol‐Induced Conformation Changes and Thermodynamic Signatures in the Binding of Polyphenols to Proline‐Rich Salivary Proteins. Chemistry – A European Journal 2023, 24
    84. Aytul Hamzalioglu, Silvia Tagliamonte, Vural Gökmen, Paola Vitaglione. Casein–phenol interactions occur during digestion and affect bioactive peptide and phenol bioaccessibility. Food & Function 2023, 14 (20) , 9457-9469.
    85. Bárbara Torres-Rochera, Elvira Manjón, María Teresa Escribano-Bailón, Ignacio García-Estévez. Role of Anthocyanins in the Interaction between Salivary Mucins and Wine Astringent Compounds. Foods 2023, 12 (19) , 3623.
    86. Dipasha Sinha, Agnes Nagy-Mehesz, Dan Simionescu, John E. Mayer, Naren Vyavahare. Pentagalloyl glucose-stabilized decellularized bovine jugular vein valved conduits as pulmonary conduit replacement. Acta Biomaterialia 2023, 170 , 97-110.
    87. Elías Obreque-Slier, Marcela Medel-Marabolí, Edio Maldonado-Maldonado, Remigio O. López-Solís. Paper chromatography approach for the assessment of interaction between red wine and whole saliva. Journal of Chromatography A 2023, 1707 , 464266.
    88. Tim J Wooster, Céline Loussert-Fonta, Anthony Ash, Romain Stoudmann, Roland Hass, Ivanna Colijn. Novel oral microscope gives mechanistic insights into colloidal drivers of friction in oral biofilms. Journal of Colloid and Interface Science 2023, 646 , 426-437.
    89. Kosei Yamauchi, Mayu Soyano, Miho Kobayashi, Yuji O. Kamatari, Tohru Mitsunaga. Protein aggregation model to explain the bioactivity of condensed tannins. Food Chemistry 2023, 416 , 135870.
    90. Paola Solis Ares, Gautam Gaur, Benjamin P. Willing, Fabian Weber, Andreas Schieber, Michael G. Gänzle. Antibacterial and enzyme inhibitory activities of flavan-3-ol monomers and procyanidin-rich grape seed fractions. Journal of Functional Foods 2023, 107 , 105643.
    91. Alp Sarisoy, Sergio Acosta, José Carlos Rodríguez-Cabello, Phillip Czichowski, Alexander Kopp, Stefan Jockenhoevel, Alicia Fernández-Colino. Bioglues Based on an Elastin-Like Recombinamer: Effect of Tannic Acid as an Additive on Tissue Adhesion and Cytocompatibility. International Journal of Molecular Sciences 2023, 24 (7) , 6776.
    92. Yun‐Shan Wei, Meng‐Jing Teng, Kun Feng, Teng‐Gen Hu, Min‐Hua Zong, Hong Wu. Improving the bioaccessibility of lipophilic ingredient in its oral intestinal delivery by ultrasound and biological cross‐linker. Journal of the Science of Food and Agriculture 2023, 103 (6) , 2762-2772.
    93. Laura E. Martin, Verenice Ascencio Gutierrez, Ann-Marie Torregrossa. The role of saliva in taste and food intake. Physiology & Behavior 2023, 262 , 114109.
    94. Nikolay Stoyanov, Panko Mitev, Mariana Galabova, Silvia Tagareva, , , , , . Phenolic compounds extractability from Melnik 55 grape solid parts during fruit maturity. BIO Web of Conferences 2023, 58 , 01016.
    95. Wenhu Xu, Shuaike Yu, Min Zhong. A review on food oral tribology. Friction 2022, 10 (12) , 1927-1966.
    96. Pik Han Chong, Jianshe Chen, Danting Yin, Lanxi Qin. Tea compound-saliva interactions and their correlations with sweet aftertaste. npj Science of Food 2022, 6 (1)
    97. Valérie Lemarcq, Davy Van de Walle, Viena Monterde, Eleni Sioriki, Koen Dewettinck. Assessing the flavor of cocoa liquor and chocolate through instrumental and sensory analysis: a critical review. Critical Reviews in Food Science and Nutrition 2022, 62 (20) , 5523-5539.
    98. Liudis L Pino‐Ramos, Paula A Peña‐Martínez, V. Felipe Laurie. Quinoa protein extract: an effective alternative for the fining of wine phenolics. Journal of the Science of Food and Agriculture 2022, 102 (14) , 6320-6327.
    99. Ivanna Colijn, Anthony Ash, Marie Dufauret, Melissa lepage, Céline Loussert-Fonta, Martin E. Leser, Peter J. Wilde, Tim J. Wooster. Colloidal dynamics of emulsion droplets in mouth. Journal of Colloid and Interface Science 2022, 620 , 153-167.
    100. Haiam O. Elkatry, Abdelrahman R. Ahmed, Hossam S. El-Beltagi, Heba I. Mohamed, Nareman S. Eshak. Biological Activities of Grape Seed By-Products and Their Potential Use as Natural Sources of Food Additives in the Production of Balady Bread. Foods 2022, 11 (13) , 1948.
    Load more citations

    Pair your accounts.

    Export articles to Mendeley

    Get article recommendations from ACS based on references in your Mendeley library.

    Pair your accounts.

    Export articles to Mendeley

    Get article recommendations from ACS based on references in your Mendeley library.

    You’ve supercharged your research process with ACS and Mendeley!

    STEP 1:
    Click to create an ACS ID

    Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

    Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

    Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

    Your Mendeley pairing has expired. Please reconnect