title: Experimental and theoretical binding affinity between polyvinylpolypyrrolidone and selected phenolic compounds from food matrices.
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.
authors.affiliation: Nanobiotechnology Division, Fraunhofer Chile Research Foundation - Center for Systems Biotechnology (FCR-CSB), Talca, Maule, Chile; Laboratory of Asymmetric Synthesis, Institute of Chemistry and Natural Resources, Universidad de Talca, Talca, Chile.
authors.forename: Esteban F
authors.initials: EF
authors.lastname: Durán-Lara
authors.affiliation: Nanobiotechnology Division, Fraunhofer Chile Research Foundation - Center for Systems Biotechnology (FCR-CSB), Talca, Maule, Chile; Laboratory of Asymmetric Synthesis, Institute of Chemistry and Natural Resources, Universidad de Talca, Talca, Chile.
authors.forename: Xaviera A
authors.initials: XA
authors.lastname: López-Cortés
authors.affiliation: Nanobiotechnology Division, Fraunhofer Chile Research Foundation - Center for Systems Biotechnology (FCR-CSB), Talca, Maule, Chile; Laboratory of Asymmetric Synthesis, Institute of Chemistry and Natural Resources, Universidad de Talca, Talca, Chile.
authors.forename: Ricardo I
authors.initials: RI
authors.lastname: Castro
authors.affiliation: Nanobiotechnology Division, Fraunhofer Chile Research Foundation - Center for Systems Biotechnology (FCR-CSB), Talca, Maule, Chile; Laboratory of Asymmetric Synthesis, Institute of Chemistry and Natural Resources, Universidad de Talca, Talca, Chile.
authors.forename: Fabián
authors.initials: F
authors.lastname: Avila-Salas
authors.affiliation: Universidad Andres Bello, Center for Bioinformatics and Integrative Biology (CBIB), Faculty of Biological Sciences, Santiago, Chile.
authors.forename: Fernando D
authors.initials: FD
authors.lastname: González-Nilo
authors.affiliation: Nanobiotechnology Division, Fraunhofer Chile Research Foundation - Center for Systems Biotechnology (FCR-CSB), Talca, Maule, Chile; School of Agricultural Sciences, Universidad de Talca, Talca, Chile.
authors.forename: V Felipe
authors.initials: VF
authors.lastname: Laurie
authors.affiliation: Nanobiotechnology Division, Fraunhofer Chile Research Foundation - Center for Systems Biotechnology (FCR-CSB), Talca, Maule, Chile; Laboratory of Asymmetric Synthesis, Institute of Chemistry and Natural Resources, Universidad de Talca, Talca, Chile. Electronic address: lssantos@utalca.cl.
authors.forename: Leonardo S
authors.initials: LS
authors.lastname: Santos
mesh_terms: D000327:Adsorption; D002392:Catechin / Q000737:chemistry / Q000302:isolation & purification; D002396:Catechols / Q000737:chemistry / Q000302:isolation & purification; D005502:Food / Q000592:standards; D005707:Gallic Acid / Q000737:chemistry / Q000302:isolation & purification; D008962:Models, Theoretical; D015394:Molecular Structure; D010636:Phenols / Q000737:chemistry* / Q000302:isolation & purification; D010936:Plant Extracts / Q000737:chemistry / Q000302:isolation & purification; D011205:Povidone / Q000031:analogs & derivatives* / Q000737:chemistry; D011794:Quercetin / Q000737:chemistry / Q000302:isolation & purification; D012996:Solutions
chemical_list: D002396:Catechols; D010636:Phenols; D010936:Plant Extracts; D012996:Solutions; C018599:4-methylcatechol; C077842:polyvinylpolypyrrolidone; D005707:Gallic Acid; D002392:Catechin; D011794:Quercetin; D011205:Povidone
keywords: Interaction energy; PM7; PVPP; Phenolic compounds; Semi-empirical methods