Document Detail

The Influence of a Flavan-3-ol Substituent on the Affinity of Anthocyanins (Pigments) Toward Vinylcatechin Dimers and Procyanidins (Copigments).
MedLine Citation:
PMID:  23131027     Owner:  NLM     Status:  Publisher    
The aim of this study is to investigate interactions possibly taking place in red wine between three flavanols (copigments, CP), i.e. two epimeric vinylcatechin dimers (CP1 and CP2) and catechin dimer B3 (CP3), and a specific pigment resulting from the condensation between the main grape anthocyanin malvidin 3-O-glucoside (oenin) and catechin: catechin-(4→8)-oenin. By comparison with our previous work on oenin itself, the influence of the catechin moiety of the anthocyanin in the binding will be established. The thermodynamic parameters show that both vinylcatechin dimers exhibit a higher affinity for catechin-(4→8)-oenin, in comparison with procyanidin B3, as previously observed with oenin. However, the corresponding binding constants are weaker, probably due to steric hindrance in the anthocyanin brought by the flavanol nucleus. Consequently, catechin-(4→8)-oenin should be much less stabilized by copigmentation in hydroalcoholic solution than oenin. Quantum mechanics and molecular dynamics simulations are also performed to interpret the binding data, specify the relative arrangement of the pigment and copigment molecules within the complexes and interpret their absorption properties in the visible range.
Frederico Nave; Natércia Fernandes Brás; Luis Cruz; Natercia Teixeira; Nuno Mateus; Maria Joäo Ramos; Florent Di Meo; Patrick Trouillas; Olivier Dangles; Victor De Freitas
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Publication Detail:
Type:  JOURNAL ARTICLE     Date:  2012-11-6
Journal Detail:
Title:  The journal of physical chemistry. B     Volume:  -     ISSN:  1520-5207     ISO Abbreviation:  J Phys Chem B     Publication Date:  2012 Nov 
Date Detail:
Created Date:  2012-11-7     Completed Date:  -     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  101157530     Medline TA:  J Phys Chem B     Country:  -    
Other Details:
Languages:  ENG     Pagination:  -     Citation Subset:  -    
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