Enzymatic Glycosylation of Phenolic Antioxidants: Phosphorylase-Mediated Synthesis and Characterization

0455579 - MBÚ 2016 RIV US eng J - Journal Article
De Winter, K. - Dewitte, W. - Dirks-Hofmeister, M. E. - De Laet, S. - Pelantová, Helena - Křen, Vladimír - Desmet, T.
Enzymatic Glycosylation of Phenolic Antioxidants: Phosphorylase-Mediated Synthesis and Characterization.
Journal of Agricultural and Food Chemistry. Roč. 63, č. 46 (2015), s. 10131-10139. ISSN 0021-8561. E-ISSN 1520-5118
R&D Projects: GA MŠMT(CZ) 7E11011; GA MŠMT(CZ) LD13042
Institutional support: RVO:61388971
Keywords : glycosylation * antioxidant * ABTS
Subject RIV: CE - Biochemistry
Impact factor: 2.857, year: 2015

Although numerous biologically active molecules exist as glycosides in nature, information on the activity, stability, and solubility of glycosylated antioxidants is rather limited to date. In this work, a wide variety of antioxidants were glycosylated using different phosphorylase enzymes. The resulting antioxidant library, containing alpha/beta-glucosides, different regioisomers, cellobiosides, and cellotriosides, was then characterized. Glycosylation was found to significantly increase the solubility and stability of all evaluated compounds. Despite decreased radical-scavenging abilities, most glycosides were identified to be potent antioxidants, outperforming the commonly used 2,6-bis(1,1-dimethylethyl)-4-methylphenol (BHT). Moreover, the point of attachment, the anomeric configuration, and the glycosidic chain length were found to influence the properties of these phenolic glycosides.
Permanent Link: http://hdl.handle.net/11104/0256210