title: Trapping by amylose of the aliphatic chain grafted onto chlorogenic acid: importance of the graft position.
abstract: 5-Caffeoylquinic acid (chlorogenic acid), is classified in acid-phenols family and as polyphenolic compounds it possesses antioxidant activity. The oxydative modification of chlorogenic acid in foods may lead to alteration of their qualities; to counteract these degradation effects, molecular encapsulation was used to protect chlorogenic acid. Amylose can interact strongly with a number of small molecules, including lipids. In order to enable chlorogenic acid complexation by amylose, a C16 aliphatic chain was previously grafted onto the cycle of quinic acid. This work showed that for the two lipophilic derivatives of chlorogenic acid: hexadecyl chlorogenate obtained by alkylation and 3-O-palmitoyl chlorogenic acid obtained by acylation; only the 3-O-palmitoyl chlorogenic acid complexed amylose. The chlorogenic acid derivatives were studied by X-ray diffraction, differential scanning calorimetry and NMR to elucidate the interaction. By comparing the results with previous work on the complexation of amylose by 4-O-palmitoyl chlorogenic acid, the importance of the aliphatic chain position on the cycle of the quinic acid is clearly highlighted. A study in molecular modeling helped to understand the difference in behavior relative to amylose of these three derivatives of chlorogenic acid.
authors.affiliation: INRA, UR 1268, Biopolymères Interactions Assemblages, Rue de la Géraudière, BP 71627, F-44316 Nantes Cedex 3, France. Electronic address: patricia.le-bail@nantes.inra.fr.
authors.forename: P
authors.initials: P
authors.lastname: Le-Bail
authors.affiliation: "Mer, Molécules, Santé" (MMS), EA 2160 IUT de Laval,Département Génie Biologique, 52 rue des Docteurs Calmette et Guérin, BP 2045, F-53020 Laval Cedex 09, France.
authors.forename: C
authors.initials: C
authors.lastname: Lorentz
authors.affiliation: "Mer, Molécules, Santé" (MMS), EA 2160 IUT de Laval,Département Génie Biologique, 52 rue des Docteurs Calmette et Guérin, BP 2045, F-53020 Laval Cedex 09, France.
authors.forename: G
authors.initials: G
authors.lastname: Pencreac'h
authors.affiliation: "Mer, Molécules, Santé" (MMS), EA 2160 IUT de Laval,Département Génie Biologique, 52 rue des Docteurs Calmette et Guérin, BP 2045, F-53020 Laval Cedex 09, France.
authors.forename: S
authors.initials: S
authors.lastname: Soultani-Vigneron
authors.affiliation: INRA, UR 1268, Biopolymères Interactions Assemblages, Rue de la Géraudière, BP 71627, F-44316 Nantes Cedex 3, France.
authors.forename: B
authors.initials: B
authors.lastname: Pontoire
authors.affiliation: UMR 1208 INRA, CIRAD, Montpellier SupAgro, Université Montpellier 2, 2 Place Viala, 34060 Montpellier Cedex 2, France.
authors.forename: L J López
authors.initials: LJL
authors.lastname: Giraldo
authors.affiliation: UMR 1208 INRA, CIRAD, Montpellier SupAgro, Université Montpellier 2, 2 Place Viala, 34060 Montpellier Cedex 2, France.
authors.forename: P
authors.initials: P
authors.lastname: Villeneuve
authors.affiliation: UMR-CNRS no. 6286 Biotechnologie, Biocatalyse & Biorégulation (U3B), 2, rue de la Houssinière, BP 92208, 44322 Nantes Cedex 3, France.
authors.forename: J
authors.initials: J
authors.lastname: Hendrickx
authors.affiliation: UMR-CNRS no. 6286 Biotechnologie, Biocatalyse & Biorégulation (U3B), 2, rue de la Houssinière, BP 92208, 44322 Nantes Cedex 3, France.
authors.forename: V
authors.initials: V
authors.lastname: Tran
mesh_terms: D000688:Amylose / Q000737:chemistry*; D002726:Chlorogenic Acid / Q000737:chemistry*; D008958:Models, Molecular; D008968:Molecular Conformation; D013696:Temperature
chemical_list: D002726:Chlorogenic Acid; D000688:Amylose
keywords: Amylose complex; CP/MAS NMR; DSC; Molecular modeling; Palmitoyl chlorogenic acid; X-ray diffraction