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

Le-Bail P., Lorentz C., Pencreac'h G., Soultani-Vigneron S., Pontoire B., Lopez Giraldo L.J., Villeneuve P., Hendrickx J., Tran V.. 2015. Carbohydrate Polymers, 117 : p. 910-916.

DOI: 10.1016/j.carbpol.2014.10.029

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.

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