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.
| Main Authors: | , , , , , , , , |
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| 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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