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Article

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

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.
Molecules 2018, 23(6), 1271; https://doi.org/10.3390/molecules23061271
Received: 4 May 2018 / Revised: 14 May 2018 / Accepted: 24 May 2018 / Published: 25 May 2018
(This article belongs to the Section Green Chemistry)
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-Text
Keywords: polyphenols; glycosylation; stilbenes; pterostilbene; cyclodextrin glycosyltransferase; enzymatic glucosylation; amyloglucosidase polyphenols; glycosylation; stilbenes; pterostilbene; cyclodextrin glycosyltransferase; enzymatic glucosylation; amyloglucosidase
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MDPI and ACS Style

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. https://doi.org/10.3390/molecules23061271

AMA Style

González-Alfonso JL, Rodrigo-Frutos D, Belmonte-Reche E, Peñalver P, Poveda A, Jiménez-Barbero J, Ballesteros AO, Hirose Y, Polaina J, Morales JC, Fernández-Lobato M, Plou FJ. Enzymatic Synthesis of a Novel Pterostilbene α-Glucoside by the Combination of Cyclodextrin Glucanotransferase and Amyloglucosidase. Molecules. 2018; 23(6):1271. https://doi.org/10.3390/molecules23061271

Chicago/Turabian Style

González-Alfonso, José L., David Rodrigo-Frutos, Efres Belmonte-Reche, Pablo Peñalver, Ana Poveda, Jesús Jiménez-Barbero, Antonio O. Ballesteros, Yoshihiko Hirose, Julio Polaina, Juan C. Morales, María Fernández-Lobato, and Francisco J. Plou. 2018. "Enzymatic Synthesis of a Novel Pterostilbene α-Glucoside by the Combination of Cyclodextrin Glucanotransferase and Amyloglucosidase" Molecules 23, no. 6: 1271. https://doi.org/10.3390/molecules23061271

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