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

Psychiatry

Journal of Addiction Research & Therapy

Author(s): Galland S, Mora N, AbertVian M, Rakotomanomana N, Dangles O

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Abstract This work describes the chemical synthesis of O-aryl-beta-D-glucosides and 1-O-beta-D-glucosyl esters of hydroxycinnamic acids. In particular, O-aryl-beta-D-glucosides were efficiently prepared via a simple diastereoselective glycosylation procedure using phase transfer conditions. Despite the lability of its ester linkage, 1-O-beta-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-beta-D-glucosides were then quantitatively investigated for their affinity for the naturally occurring anthocyanin malvin (pigment). Formation of the pi-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. This article was published in J Agric Food Chem and referenced in Journal of Addiction Research & Therapy

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