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

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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
https://doi.org/10.1021/bi9700328
Copyright © 1997 American Chemical Society

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    Abstract

    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.

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    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.

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    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.

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