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

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.

Bibliographic Details

Main Authors:	Le-Bail, Patricia, Lorentz, C., Pencreac'h, Gaëlle, Soultani-Vigneron, S., Pontoire, Bruno, Lopez Giraldo, Luis Javier, Villeneuve, Pierre, Hendrickx, J., Tran, V.
Format:	article biblioteca
Language:	eng
Subjects:	Q02 - Traitement et conservation des produits alimentaires, Q04 - Composition des produits alimentaires, acide chlorogénique, antioxydant, amylose, encapsulation, greffage, qualité des aliments, polyphénol, http://aims.fao.org/aos/agrovoc/c_36179, http://aims.fao.org/aos/agrovoc/c_511, http://aims.fao.org/aos/agrovoc/c_372, http://aims.fao.org/aos/agrovoc/c_28357, http://aims.fao.org/aos/agrovoc/c_3344, http://aims.fao.org/aos/agrovoc/c_10965, http://aims.fao.org/aos/agrovoc/c_15881,
Online Access:	http://agritrop.cirad.fr/575166/ http://agritrop.cirad.fr/575166/1/document_575166.pdf
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