Chemical synthesis of hydroxycinnamic acid glucosides and evaluation of their ability to stabilize natural colors via anthocyanin copigmentation.
J Agric Food Chem
; 55(18): 7573-9, 2007 Sep 05.
Article
in En
| MEDLINE
| ID: mdl-17685544
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.
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Collection:
01-internacional
Database:
MEDLINE
Main subject:
Pigmentation
/
Coumaric Acids
/
Glucosides
/
Anthocyanins
Language:
En
Journal:
J Agric Food Chem
Year:
2007
Document type:
Article
Affiliation country: