title: Coupling lipophilization and amylose complexation to encapsulate chlorogenic acid.
abstract: Chlorogenic acid (5-caffeoylquinic acid) is a hydrophilic phenolic compound with antioxidant properties. Because of its high polarity, these properties may be altered when formulated in oil-based food. There is therefore an interest in trying to protect the natural antioxidant by molecular encapsulation. Amylose, the linear fraction of starch with essentially α(1-4) linkages, is well known for its ability to form semi-crystalline complexes with a variety of small ligands. Monoacyl lipids, as well as smaller ligands such as alcohols or flavor compounds, are able to induce the formation of left-handed amylose single helices. In contrast, chlorogenic acid is a bulky molecule whose topology requires the amylose helix to be distorted, which could prevent amylose complexation. An innovative strategy has been developed to overcome this problem by grafting an aliphatic chain onto chlorogenic acid then trapping this chain in the helical cavity. The lipophilization reaction was used to obtain a palmitoyl chlorogenic acid derivative and the amylose-palmitoyl chlorogenic acid assemblies were studied by X-ray diffraction, differential scanning calorimetry and NMR to elucidate the interaction. The results showed that such interactions between amylose and palmitoyl chlorogenic acid are effective.
authors.affiliation: Laboratoire Mer, Molécules, Santé, EA 2160, Université du Maine, Institut Universitaire de Technologie de Laval, 52 rue des Drs Calmette et Guérin, BP 2045, 53020 Laval cedex 9, France.
authors.forename: C
authors.initials: C
authors.lastname: Lorentz
authors.affiliation: Laboratoire Mer, Molécules, Santé, EA 2160, Université du Maine, Institut Universitaire de Technologie de Laval, 52 rue des Drs Calmette et Guérin, BP 2045, 53020 Laval cedex 9, France.
authors.forename: G
authors.initials: G
authors.lastname: Pencreac'h
authors.affiliation: Laboratoire Mer, Molécules, Santé, EA 2160, Université du Maine, Institut Universitaire de Technologie de Laval, 52 rue des Drs Calmette et Guérin, BP 2045, 53020 Laval cedex 9, France.
authors.forename: S
authors.initials: S
authors.lastname: Soultani-Vigneron
authors.affiliation: UR1268, Biopolymères, Interactions, Assemblages, INRA, F-44300 Nantes, France.
authors.forename: C
authors.initials: C
authors.lastname: Rondeau-Mouro
authors.affiliation: UR1268, Biopolymères, Interactions, Assemblages, INRA, F-44300 Nantes, France.
authors.forename: M
authors.initials: M
authors.lastname: de Carvalho
authors.affiliation: UR1268, Biopolymères, Interactions, Assemblages, INRA, F-44300 Nantes, France.
authors.forename: B
authors.initials: B
authors.lastname: Pontoire
authors.affiliation: Laboratoire Mer, Molécules, Santé, EA 2160, Université du Maine, Institut Universitaire de Technologie de Laval, 52 rue des Drs Calmette et Guérin, BP 2045, 53020 Laval cedex 9, France.
authors.forename: F
authors.initials: F
authors.lastname: Ergan
authors.affiliation: UR1268, Biopolymères, Interactions, Assemblages, INRA, F-44300 Nantes, France.
authors.forename: P
authors.initials: P
authors.lastname: Le Bail
mesh_terms: D000688:Amylose / Q000737:chemistry*; D000975:Antioxidants / Q000008:administration & dosage / Q000737:chemistry* / Q000378:metabolism; D002175:Candida / Q000201:enzymology; D002726:Chlorogenic Acid / Q000008:administration & dosage / Q000031:analogs & derivatives* / Q000737:chemistry / Q000378:metabolism; D004339:Drug Compounding; D005503:Food Additives / Q000008:administration & dosage / Q000737:chemistry* / Q000378:metabolism; D005612:Freeze Drying; D005656:Fungal Proteins / Q000378:metabolism; D008049:Lipase / Q000378:metabolism; D014961:X-Ray Diffraction
chemical_list: D000975:Antioxidants; D005503:Food Additives; D005656:Fungal Proteins; D002726:Chlorogenic Acid; D000688:Amylose; D008049:Lipase; C431349:lipase B, Candida antarctica