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Issue 51, 2016, Issue in Progress
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The influence of the carbohydrate anomeric linkage on the free radical scavenging activity of enzymatically-synthesized phenolic glycosides

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Abstract

Phenolic glycosides, widely recognized for their nutraceutical properties exist in nature as α- and β-glycosides. Interestingly, the β-phenolic glycosides are the predominant form in natural products. In this work, the pure α- and β-glucosides and galactosides of homovanillyl alcohol (HVA) were enzymatically synthesized. Their free radical scavenger (FRS) activity was evaluated using the DPPH˙ endpoint assay. According to the EC50 values, all glycosides are better FRSs than the corresponding aglycone, with lower EC50 values found for the β-anomers. In contrast, a DPPH˙ kinetic analysis revealed that HVA-aglycone is more reactive than the glycosides. The analysis based on both EC50 and kinetic behaviour suggested that, although the HVA-aglycone is kinetically a better free radical scavenger, glycosidation renders HVA-aglycone more stable for long-term reactions. The molecular electrostatic potential and conformational analysis of α- and β-HVA glycosides demonstrated that β-HVA glycosides are better free radical scavengers than the corresponding α-anomers. In fact, the higher flexibility of β-HVA glycosides allow the exposure of advantageously negatively charged regions favouring their FRS capacity.

Graphical abstract: The influence of the carbohydrate anomeric linkage on the free radical scavenging activity of enzymatically-synthesized phenolic glycosides

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Supplementary files

Article information


Submitted
11 Mar 2016
Accepted
02 May 2016
First published
04 May 2016

RSC Adv., 2016,6, 45452-45461
Article type
Paper

The influence of the carbohydrate anomeric linkage on the free radical scavenging activity of enzymatically-synthesized phenolic glycosides

J. A. González-Ríos, J. Pedraza-Chaverri, O. N. Medina-Campos, M. Reina, Y. Romero, A. Martínez, A. López-Munguía and E. Castillo, RSC Adv., 2016, 6, 45452
DOI: 10.1039/C6RA06572D

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