Experimental and theoretical binding affinity between polyvinylpolypyrrolidone and selected phenolic compounds from food matrices

Esteban F. Durán-Lara, Xaviera A. López-Cortés, Ricardo I. Castro, Fabián Avila-Salas, Fernando D. González-Nilo, V. Felipe Laurie, Leonardo S. Santos

Resultado de la investigación: Article

17 Citas (Scopus)

Resumen

Polyvinylpolypyrrolidone (PVPP) is a fining agent, widely used in winemaking and brewing, whose mode of action in removing phenolic compounds has not been fully characterised. The aim of this study was to evaluate the experimental and theoretical binding affinity of PVPP towards six phenolic compounds representing different types of phenolic species. The interaction between PVPP and phenolics was evaluated in model solutions, where hydroxyl groups, hydrophobic bonding and steric hindrance were characterised. The results of the study indicated that PVPP exhibits high affinity for quercetin and catechin, moderate affinity for epicatechin, gallic acid and lower affinity for 4-methylcatechol and caffeic acid. The affinity has a direct correlation with the hydroxylation degree of each compound. The results show that the affinity of PVPP towards phenols is related with frontier orbitals. This work demonstrates a direct correlation between the experimental affinity and the interaction energy calculations obtained through computational chemistry methods.

Idioma originalEnglish
Páginas (desde-hasta)464-470
Número de páginas7
PublicaciónFood Chemistry
Volumen168
DOI
EstadoPublished - 1 feb 2015

Huella dactilar

food matrix
phenolic compounds
Food
hydrophobic bonding
brewing
epicatechin
hydroxylation
winemaking
caffeic acid
gallic acid
catechin
phenols
quercetin
Catechin
mechanism of action
chemistry
Brewing
Computational chemistry
energy
Hydroxylation

ASJC Scopus subject areas

  • Analytical Chemistry
  • Food Science

Citar esto

Durán-Lara, Esteban F. ; López-Cortés, Xaviera A. ; Castro, Ricardo I. ; Avila-Salas, Fabián ; González-Nilo, Fernando D. ; Laurie, V. Felipe ; Santos, Leonardo S. / Experimental and theoretical binding affinity between polyvinylpolypyrrolidone and selected phenolic compounds from food matrices. En: Food Chemistry. 2015 ; Vol. 168. pp. 464-470.
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abstract = "Polyvinylpolypyrrolidone (PVPP) is a fining agent, widely used in winemaking and brewing, whose mode of action in removing phenolic compounds has not been fully characterised. The aim of this study was to evaluate the experimental and theoretical binding affinity of PVPP towards six phenolic compounds representing different types of phenolic species. The interaction between PVPP and phenolics was evaluated in model solutions, where hydroxyl groups, hydrophobic bonding and steric hindrance were characterised. The results of the study indicated that PVPP exhibits high affinity for quercetin and catechin, moderate affinity for epicatechin, gallic acid and lower affinity for 4-methylcatechol and caffeic acid. The affinity has a direct correlation with the hydroxylation degree of each compound. The results show that the affinity of PVPP towards phenols is related with frontier orbitals. This work demonstrates a direct correlation between the experimental affinity and the interaction energy calculations obtained through computational chemistry methods.",
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Experimental and theoretical binding affinity between polyvinylpolypyrrolidone and selected phenolic compounds from food matrices. / Durán-Lara, Esteban F.; López-Cortés, Xaviera A.; Castro, Ricardo I.; Avila-Salas, Fabián; González-Nilo, Fernando D.; Laurie, V. Felipe; Santos, Leonardo S.

En: Food Chemistry, Vol. 168, 01.02.2015, p. 464-470.

Resultado de la investigación: Article

TY - JOUR

T1 - Experimental and theoretical binding affinity between polyvinylpolypyrrolidone and selected phenolic compounds from food matrices

AU - Durán-Lara, Esteban F.

AU - López-Cortés, Xaviera A.

AU - Castro, Ricardo I.

AU - Avila-Salas, Fabián

AU - González-Nilo, Fernando D.

AU - Laurie, V. Felipe

AU - Santos, Leonardo S.

PY - 2015/2/1

Y1 - 2015/2/1

N2 - Polyvinylpolypyrrolidone (PVPP) is a fining agent, widely used in winemaking and brewing, whose mode of action in removing phenolic compounds has not been fully characterised. The aim of this study was to evaluate the experimental and theoretical binding affinity of PVPP towards six phenolic compounds representing different types of phenolic species. The interaction between PVPP and phenolics was evaluated in model solutions, where hydroxyl groups, hydrophobic bonding and steric hindrance were characterised. The results of the study indicated that PVPP exhibits high affinity for quercetin and catechin, moderate affinity for epicatechin, gallic acid and lower affinity for 4-methylcatechol and caffeic acid. The affinity has a direct correlation with the hydroxylation degree of each compound. The results show that the affinity of PVPP towards phenols is related with frontier orbitals. This work demonstrates a direct correlation between the experimental affinity and the interaction energy calculations obtained through computational chemistry methods.

AB - Polyvinylpolypyrrolidone (PVPP) is a fining agent, widely used in winemaking and brewing, whose mode of action in removing phenolic compounds has not been fully characterised. The aim of this study was to evaluate the experimental and theoretical binding affinity of PVPP towards six phenolic compounds representing different types of phenolic species. The interaction between PVPP and phenolics was evaluated in model solutions, where hydroxyl groups, hydrophobic bonding and steric hindrance were characterised. The results of the study indicated that PVPP exhibits high affinity for quercetin and catechin, moderate affinity for epicatechin, gallic acid and lower affinity for 4-methylcatechol and caffeic acid. The affinity has a direct correlation with the hydroxylation degree of each compound. The results show that the affinity of PVPP towards phenols is related with frontier orbitals. This work demonstrates a direct correlation between the experimental affinity and the interaction energy calculations obtained through computational chemistry methods.

KW - Interaction energy

KW - Phenolic compounds

KW - PM7

KW - PVPP

KW - Semi-empirical methods

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