Optimization of Regioselective α-Glucosylation of Hesperetin Catalyzed by Cyclodextrin Glucanotransferase

Molecules

Jesús Jiménez-Barbero¹  Ana Poveda¹  J. Daniel Padilla²  Antonio O. Ballesteros³  José L. González-Alfonso³  Francisco J. Plou³  Noa Míguez³  Laura Leemans³  Georgina Sandoval³ 

[1] Center for Cooperative Research in Biosciences, Parque Científico Tecnológico de Bizkaia, 48160 Derio, Biscay, Spain;Centro de Investigación y Asistencia en Tecnología y Diseño del Estado de Jalisco (CIATEJ), Guadalajara 44270, Jalisco, Mexico;Instituto de Catálisis y Petroleoquímica, CSIC, 28049 Madrid, Spain;

关键词: polyphenols;    glycosylation;    flavonoids;    flavanones;    cyclodextrin glucosyltransferase;    enzymatic glucosylation;    hesperidin;    hesperetin;   

DOI  :  10.3390/molecules23112885

来源: DOAJ

【 摘 要 】

The regioselective α-glucosylation of hesperetin was achieved by a transglycosylation reaction catalyzed by cyclodextrin glucanotransferase (CGTase) from Thermoanaerobacter sp. using soluble starch as glucosyl donor. By combining mass spectrometry (ESI-TOF) and 2D-NMR analysis, the main monoglucosylated derivative was fully characterized (hesperetin 7-O-α-d-glucopyranoside). In order to increase the yield of monoglucoside, several reaction parameters were optimized: Nature and percentage of cosolvent, composition of the aqueous phase, glucosyl donor, temperature, and the concentrations of hesperetin and soluble starch. Under the optimal conditions, which included the presence of 30% of bis(2-methoxyethyl) ether as cosolvent, the maximum concentration of monoglucoside was approximately 2 mM, obtained after 24 h of reaction. To our knowledge, this is the first report of direct glucosylation of hesperetin employing free enzymes instead of whole cells.

【 授权许可】

Unknown