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Planta Med 2011; 77(11): 1116-1122
DOI: 10.1055/s-0030-1270848
Lectures 7th Tannin Conference
Original Papers
© Georg Thieme Verlag KG Stuttgart · New York

Towards a Molecular Interpretation of Astringency: Synthesis, 3D Structure, Colloidal State, and Human Saliva Protein Recognition of Procyanidins

Olivier Cala2 , Sandy Fabre1 , Noël Pinaud1 , Erick J. Dufourc2 , Eric Fouquet1 , Michel Laguerre2 , Isabelle Pianet1
  • 1UMR 5255 ISM CESAMO, Université Bordeaux, CNRS, Talence, France
  • 2UMR 5248 CBMN, Université Bordeaux, CNRS, ENITAB, IECB, Pessac, France
Further Information

Publication History

received October 6, 2010 revised February 4, 2011

accepted February 8, 2011

Publication Date:
16 March 2011 (online)

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Abstract

Astringency is a sensation in the mouth used in judging the quality of red wine. The rough, dry, and puckering sensation called astringency is the result of an interaction between tannins and saliva proteins, mainly proline-rich proteins (PRP), which leads to the formation and precipitation of a complex. A dry and rough sensation is then perceived in the mouth. To get an insight into astringency at the molecular level we investigated: (i) An efficient and iterative method for 4–8 procyanidin synthesis, which gives rise to all possible 4–8 procyanidins up to the tetramer with total control of degree of oligomerization and stereochemistry. (ii) The 3D‐structural preferences, which take into account their internal movements, using 2D NMR and molecular modeling. (iii) The self-association process in water or hydroalcoholic solutions using diffusion NMR spectroscopy that gives the active proportion of tannins able to fix proteins. (iv) A comprehensive description of the PRP-procyanidin complex formation to get information about stoichiometry, binding site localization, and affinity constants for different procyanidins. The data collected suggest that the interactions are controlled by both procyanidin conformational and colloidal state preferences. All these results provide new insights into the molecular interpretation of tannin astringency.

Key words

procyanidin - proline rich peptide - astringency - NMR - molecular dynamics

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Dr. Isabelle Pianet

Institut des Sciences Moléculaires, CESAMO
Université Bordeaux 1

351 Cours de la Libération

33405 Talence

France

Phone: +33 5 40 00 64 48

Fax: +33 5 40 00 26 23

Email: i.pianet@ism.u-bordeaux1.fr

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