Characterization of Sensory Properties of Flavanols--A Molecular Dynamic Approach

[EN] In this work, sensations elicited by catechin and procyanidins in comparison with those elicited by gallocatechin and prodelphinidins were evaluated by means of a sensory panel. To obtain further insights into the mechanisms of action, molecular dynamics (MD) simulations and saturation transfer...

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Autores: Ferrer-Gallego, Raúl, Quijada-Morín, Natalia, Brás, Natércia F., Gomes, P., de Freitas, Victor, Rivas Gonzalo, Julián C., Escribano Bailón, María Teresa
Formato: artículo
Estado:Versión publicada
Fecha de publicación:2015
País:España
Recursos:Universidad de Salamanca (USAL)
Repositorio:GREDOS. Repositorio Institucional de la Universidad de Salamanca
OAI Identifier:oai:gredos.usal.es:10366/141101
Acesso em linha:http://hdl.handle.net/10366/141101
Access Level:acceso abierto
Palavra-chave:Astringency
Bitterness
Flavanols
IB7
Molecular dynamic simulations
STD NMR
2417.17 Nutrición Vegetal
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spelling Characterization of Sensory Properties of Flavanols--A Molecular Dynamic ApproachFerrer-Gallego, RaúlQuijada-Morín, NataliaBrás, Natércia F.Gomes, P.de Freitas, VictorRivas Gonzalo, Julián C.Escribano Bailón, María TeresaAstringencyBitternessFlavanolsIB7Molecular dynamic simulationsSTD NMR2417.17 Nutrición Vegetal[EN] In this work, sensations elicited by catechin and procyanidins in comparison with those elicited by gallocatechin and prodelphinidins were evaluated by means of a sensory panel. To obtain further insights into the mechanisms of action, molecular dynamics (MD) simulations and saturation transfer difference nuclear magnetic resonance (STD NMR) experiments have been performed. Results showed clear differences between the 2 types of flavanols. Dihydroxylated B-ring flavanols were more astringent, bitter, dry, rough, unripe, and persistent than trihydroxylated B-ring ones. Besides, these last compounds were smoother, more velvety, and viscous. MD simulations and STD NMR experiments support results obtained from tasting panel. MD results suggested that catechin binds to a human salivary proline-rich peptide IB714 faster than gallocatechin and this interaction is maintained longer. IB714 can interact with 2 catechin molecules concurrently while only interacts with 1 gallocatechin molecule. Accordingly, STD NMR experiments showed a greater affinity of catechin than gallocatechin for the peptide (KD = 2.7 and 25.7, respectively). Results indicate that the number of hydroxyl substituents present in B-ring of the flavanic nucleus is decisive for the interaction with salivary proteins and the development of astringency perception.202020202015info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://hdl.handle.net/10366/141101reponame:GREDOS. Repositorio Institucional de la Universidad de Salamancainstname:Universidad de Salamanca (USAL)InglésAttribution-NonCommercial-NoDerivatives 4.0 Internacionalhttp://creativecommons.org/licenses/by-nc-nd/4.0/info:eu-repo/semantics/openAccessoai:gredos.usal.es:10366/1411012026-06-07T06:28:51Z
dc.title.none.fl_str_mv Characterization of Sensory Properties of Flavanols--A Molecular Dynamic Approach
title Characterization of Sensory Properties of Flavanols--A Molecular Dynamic Approach
spellingShingle Characterization of Sensory Properties of Flavanols--A Molecular Dynamic Approach
Ferrer-Gallego, Raúl
Astringency
Bitterness
Flavanols
IB7
Molecular dynamic simulations
STD NMR
2417.17 Nutrición Vegetal
title_short Characterization of Sensory Properties of Flavanols--A Molecular Dynamic Approach
title_full Characterization of Sensory Properties of Flavanols--A Molecular Dynamic Approach
title_fullStr Characterization of Sensory Properties of Flavanols--A Molecular Dynamic Approach
title_full_unstemmed Characterization of Sensory Properties of Flavanols--A Molecular Dynamic Approach
title_sort Characterization of Sensory Properties of Flavanols--A Molecular Dynamic Approach
dc.creator.none.fl_str_mv Ferrer-Gallego, Raúl
Quijada-Morín, Natalia
Brás, Natércia F.
Gomes, P.
de Freitas, Victor
Rivas Gonzalo, Julián C.
Escribano Bailón, María Teresa
author Ferrer-Gallego, Raúl
author_facet Ferrer-Gallego, Raúl
Quijada-Morín, Natalia
Brás, Natércia F.
Gomes, P.
de Freitas, Victor
Rivas Gonzalo, Julián C.
Escribano Bailón, María Teresa
author_role author
author2 Quijada-Morín, Natalia
Brás, Natércia F.
Gomes, P.
de Freitas, Victor
Rivas Gonzalo, Julián C.
Escribano Bailón, María Teresa
author2_role author
author
author
author
author
author
dc.subject.none.fl_str_mv Astringency
Bitterness
Flavanols
IB7
Molecular dynamic simulations
STD NMR
2417.17 Nutrición Vegetal
topic Astringency
Bitterness
Flavanols
IB7
Molecular dynamic simulations
STD NMR
2417.17 Nutrición Vegetal
description [EN] In this work, sensations elicited by catechin and procyanidins in comparison with those elicited by gallocatechin and prodelphinidins were evaluated by means of a sensory panel. To obtain further insights into the mechanisms of action, molecular dynamics (MD) simulations and saturation transfer difference nuclear magnetic resonance (STD NMR) experiments have been performed. Results showed clear differences between the 2 types of flavanols. Dihydroxylated B-ring flavanols were more astringent, bitter, dry, rough, unripe, and persistent than trihydroxylated B-ring ones. Besides, these last compounds were smoother, more velvety, and viscous. MD simulations and STD NMR experiments support results obtained from tasting panel. MD results suggested that catechin binds to a human salivary proline-rich peptide IB714 faster than gallocatechin and this interaction is maintained longer. IB714 can interact with 2 catechin molecules concurrently while only interacts with 1 gallocatechin molecule. Accordingly, STD NMR experiments showed a greater affinity of catechin than gallocatechin for the peptide (KD = 2.7 and 25.7, respectively). Results indicate that the number of hydroxyl substituents present in B-ring of the flavanic nucleus is decisive for the interaction with salivary proteins and the development of astringency perception.
publishDate 2015
dc.date.none.fl_str_mv 2015
2020
2020
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/10366/141101
url http://hdl.handle.net/10366/141101
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.rights.none.fl_str_mv Attribution-NonCommercial-NoDerivatives 4.0 Internacional
http://creativecommons.org/licenses/by-nc-nd/4.0/
info:eu-repo/semantics/openAccess
rights_invalid_str_mv Attribution-NonCommercial-NoDerivatives 4.0 Internacional
http://creativecommons.org/licenses/by-nc-nd/4.0/
eu_rights_str_mv openAccess
dc.source.none.fl_str_mv reponame:GREDOS. Repositorio Institucional de la Universidad de Salamanca
instname:Universidad de Salamanca (USAL)
instname_str Universidad de Salamanca (USAL)
reponame_str GREDOS. Repositorio Institucional de la Universidad de Salamanca
collection GREDOS. Repositorio Institucional de la Universidad de Salamanca
repository.name.fl_str_mv
repository.mail.fl_str_mv
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score 15,300724

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