Molecules 2018, 23(6), 1271; https://doi.org/10.3390/molecules23061271
Enzymatic Synthesis of a Novel Pterostilbene α-Glucoside by the Combination of Cyclodextrin Glucanotransferase and Amyloglucosidase
José L. González-Alfonso 1
, David Rodrigo-Frutos 2, Efres Belmonte-Reche 3, Pablo Peñalver 3, Ana Poveda 4, Jesús Jiménez-Barbero 4, Antonio O. Ballesteros 1, Yoshihiko Hirose 5, Julio Polaina 6, Juan C. Morales 3, María Fernández-Lobato 2 and Francisco J. Plou 1,*
, David Rodrigo-Frutos 2, Efres Belmonte-Reche 3, Pablo Peñalver 3, Ana Poveda 4, Jesús Jiménez-Barbero 4, Antonio O. Ballesteros 1, Yoshihiko Hirose 5, Julio Polaina 6, Juan C. Morales 3, María Fernández-Lobato 2 and Francisco J. Plou 1,*
1
Instituto de Catálisis y Petroleoquímica, CSIC, 28049 Madrid, Spain
2
Centro de Biología Molecular Severo Ochoa (CSIC-UAM), Departamento Biología Molecular, UAM, 28049 Madrid, Spain
3
Instituto de Parasitología y Biomedicina “Lopez-Neyra”, CSIC, PTS Granada, 18016 Armilla, Granada, Spain
4
Center for Cooperative Research in Biosciences, Parque Científico Tecnológico de Bizkaia, 48160 Derio, Biscay, Spain
5
Enzyme Techno, Naganatsu, Ogaki, Gifu 503-0997, Japan
6
Instituto de Agroquímica y Tecnología de Alimentos, CSIC, 46980 Valencia, Spain
*
Author to whom correspondence should be addressed.
Received: 4 May 2018 / Revised: 14 May 2018 / Accepted: 24 May 2018 / Published: 25 May 2018
(This article belongs to the Section Green Chemistry)
Abstract
The 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. View Full-TextKeywords:
polyphenols; glycosylation; stilbenes; pterostilbene; cyclodextrin glycosyltransferase; enzymatic glucosylation; amyloglucosidase
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González-Alfonso, J.L.; Rodrigo-Frutos, D.; Belmonte-Reche, E.; Peñalver, P.; Poveda, A.; Jiménez-Barbero, J.; Ballesteros, A.O.; Hirose, Y.; Polaina, J.; Morales, J.C.; Fernández-Lobato, M.; Plou, F.J. Enzymatic Synthesis of a Novel Pterostilbene α-Glucoside by the Combination of Cyclodextrin Glucanotransferase and Amyloglucosidase. Molecules 2018, 23, 1271.
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