期刊
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY
卷 55, 期 18, 页码 7573-7579出版社
AMER CHEMICAL SOC
DOI: 10.1021/jf071205v
关键词
hydroxycinnamic acid; glucoside; glucosyl ester; synthesis; copigmentation; anthocyanin
This work describes the chemical synthesis of O-aryi-beta-D-glucosides and 1 -O-beta-D-glucosyl esters of hydroxycinnamic acids. In particular, OLaryl-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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