Trapping by amylose of the aliphatic chain grafted onto chlorogenic acid: Importance of the graft position

Le-Bail Patricia, Lorentz C., Pencreac'h Gaëlle, Soultani-Vigneron S., Pontoire Bruno, Lopez Giraldo Luis Javier, Villeneuve Pierre, Hendrickx J., Tran V.. 2015. Trapping by amylose of the aliphatic chain grafted onto chlorogenic acid: Importance of the graft position. Carbohydrate Polymers, 117 : 910-916.

Quartile : Q1, Sujet : CHEMISTRY, APPLIED / Quartile : Q1, Sujet : POLYMER SCIENCE / Quartile : Q1, Sujet : CHEMISTRY, ORGANIC

Résumé : 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 eluci-date the interaction. By comparing the results with previous work on the complexation of amylose by4-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.

Mots-clés Agrovoc : acide chlorogénique, antioxydant, amylose, encapsulation, greffage, qualité des aliments, polyphénol

Classification Agris : Q02 - Traitement et conservation des produits alimentaires
Q04 - Composition des produits alimentaires

Champ stratégique Cirad : Axe 3 (2014-2018) - Alimentation durable

Auteurs et affiliations

• Le-Bail Patricia, INRA (FRA)
• Lorentz C., Institut universitaire de technologie de Laval (FRA)
• Pencreac'h Gaëlle, Institut universitaire de technologie de Laval (FRA)
• Soultani-Vigneron S., Institut universitaire de technologie de Laval (FRA)
• Pontoire Bruno, INRA (FRA)
• Lopez Giraldo Luis Javier, INRA (FRA)
• Villeneuve Pierre, CIRAD-PERSYST-UMR IATE (FRA) ORCID: 0000-0003-1685-1494
• Hendrickx J., CNRS (FRA)
• Tran V., CNRS (FRA)

Source : Cirad - Agritrop (https://agritrop.cirad.fr/575166/)

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