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Enzymatic Synthesis of a Novel Pterostilbene α-Glucoside by the Combination of Cyclodextrin Glucanotransferase and Amyloglucosidase

AutorGonzález-Alfonso, José L.; Rodrigo-Frutos, David; Belmonte-Reche, Efres; Peñalver, Pablo ; Poveda, Ana; Jiménez-Barbero, Jesús ; Ballesteros Olmo, Antonio ; Hirose, Yoshihiko; Polaina Molina, Julio ; Morales, Juan C.; Fernández Lobato, María ; Plou Gasca, Francisco José
Palabras clavePolyphenols
Glycosylation
Stilbenes
Pterostilbene
Cyclodextrin glycosyltransferase
Enzymatic glucosylation
Amyloglucosidase
Fecha de publicación25-may-2018
EditorMultidisciplinary Digital Publishing Institute
CitaciónMolecules 23(6): 1271 (2018)
ResumenThe synthesis of a novel α-glucosylated derivative of pterostilbene was performed by a transglycosylation reaction using starch as glucosyl donor, catalyzed by cyclodextrin glucanotransferase (CGTase) from Thermoanaerobacter sp. The reaction was carried out in a buffer containing 20% (v/v) DMSO to enhance the solubility of pterostilbene. Due to the formation of several polyglucosylated products with CGTase, the yield of monoglucoside was increased by the treatment with a recombinant amyloglucosidase (STA1) from Saccharomyces cerevisiae (var. diastaticus). This enzyme was not able to hydrolyze the linkage between the glucose and pterostilbene. The monoglucoside was isolated and characterized by combining ESI-MS and 2D-NMR methods. Pterostilbene α-d-glucopyranoside is a novel compound. The α-glucosylation of pterostilbene enhanced its solubility in water to approximately 0.1 g/L. The α-glucosylation caused a slight loss of antioxidant activity towards ABTS˙+ radicals. Pterostilbene α-d-glucopyranoside was less toxic than pterostilbene for human SH-S5Y5 neurons, MRC5 fibroblasts and HT-29 colon cancer cells, and similar for RAW 264.7 macrophages.
Versión del editorhttp://dx.doi.org/10.3390/molecules23061271
URIhttp://hdl.handle.net/10261/165157
DOI10.3390/molecules23061271
E-ISSN1420-3049
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