Chemical synthesis of hydroxycinnamic acid glucosides and evaluation of their ability to stabilize natural colors via anthocyanin copigmentation - INRAE - Institut national de recherche pour l’agriculture, l’alimentation et l’environnement Access content directly
Journal Articles Journal of Agricultural and Food Chemistry Year : 2007

Chemical synthesis of hydroxycinnamic acid glucosides and evaluation of their ability to stabilize natural colors via anthocyanin copigmentation

Abstract

This work describes the chemical synthesis of O-aryl--D-glucosides and 1-O--D-glucosyl esters of hydroxycinnamic acids. In particular, O-aryl--D-glucosides were efficiently prepared via a simple diastereoselective glycosylation procedure using phase transfer conditions. Despite the lability of its ester linkage, 1-O--D-caffeoylglucose could also be obtained using a Lewis acid catalyzed glycosylation step and a set of protective groups that can be removed under neutral conditions. Hydroxycinnamic acid O-aryl--D-glucosides were then quantitatively investigated for their affinity for the naturally occurring anthocyanin malvin (pigment). Formation of the -stacking molecular complexes (copigmentation) was characterized in terms of binding constants and enthalpy and entropy changes. The glucosyl moiety did not significantly alter these thermodynamic parameters, in line with a binding process solely involving the polyphenolic nuclei.

Dates and versions

hal-02661088 , version 1 (30-05-2020)

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Stéphanie Galland, Nathalie Mora, Maryline Abert-Vian, Njara Rakotomanomana, Olivier O. Dangles. Chemical synthesis of hydroxycinnamic acid glucosides and evaluation of their ability to stabilize natural colors via anthocyanin copigmentation. Journal of Agricultural and Food Chemistry, 2007, 55 (18), pp.7573-7579. ⟨10.1021/jf071205v⟩. ⟨hal-02661088⟩
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