Enzymatic Synthesis of a Novel Pterostilbene α-Glucoside by the Combination of Cyclodextrin Glucanotransferase and Amyloglucosidase
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 e...
| Autores: | , , , , , , , , , , , |
|---|---|
| Tipo de recurso: | artículo |
| Estado: | Versión publicada |
| Fecha de publicación: | 2018 |
| País: | España |
| Institución: | Consejo Superior de Investigaciones Científicas (CSIC) |
| Repositorio: | DIGITAL.CSIC. Repositorio Institucional del CSIC |
| OAI Identifier: | oai:digital.csic.es:10261/165157 |
| Acceso en línea: | http://hdl.handle.net/10261/165157 |
| Access Level: | acceso abierto |
| Palabra clave: | Polyphenols Glycosylation Stilbenes Pterostilbene Cyclodextrin glycosyltransferases Enzymatic glucosylation Amyloglucosidase |
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Enzymatic Synthesis of a Novel Pterostilbene α-Glucoside by the Combination of Cyclodextrin Glucanotransferase and AmyloglucosidaseGonzález-Alfonso, José L.Rodrigo-Frutos, DavidBelmonte-Reche, EfresPeñalver, PabloPoveda, AnaJiménez-Barbero, JesúsBallesteros Olmo, AntonioHirose, YoshihikoPolaina Molina, JulioMorales, Juan CarlosFernández Lobato, MaríaPlou Gasca, Francisco JoséPolyphenolsGlycosylationStilbenesPterostilbeneCyclodextrin glycosyltransferasesEnzymatic glucosylationAmyloglucosidaseThe 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.This research was funded by the Spanish Ministry of Economy and Competitiveness (Grants BIO2016-76601-C3-1-R and BIO2016-76601-C3-3-R).Peer reviewedMultidisciplinary Digital Publishing InstituteMinisterio de Economía y Competitividad (España)Consejo Superior de Investigaciones Científicas [https://ror.org/02gfc7t72]201820182018info:eu-repo/semantics/articlehttp://purl.org/coar/resource_type/c_6501Publisher's versioninfo:eu-repo/semantics/publishedVersionhttp://hdl.handle.net/10261/165157reponame:DIGITAL.CSIC. Repositorio Institucional del CSICinstname:Consejo Superior de Investigaciones Científicas (CSIC)Inglés#PLACEHOLDER_PARENT_METADATA_VALUE##PLACEHOLDER_PARENT_METADATA_VALUE#info:eu-repo/grantAgreement/MINECO/Plan Estatal de Investigación Científica y Técnica y de Innovación 2013-2016/BIO2016-76601-C3-1-Rinfo:eu-repo/grantAgreement/MINECO/Plan Estatal de Investigación Científica y Técnica y de Innovación 2013-2016/BIO2016-76601-C3-3-Rhttp://dx.doi.org/10.3390/molecules23061271Síinfo:eu-repo/semantics/openAccessoai:digital.csic.es:10261/1651572026-05-22T06:33:51Z |
| dc.title.none.fl_str_mv |
Enzymatic Synthesis of a Novel Pterostilbene α-Glucoside by the Combination of Cyclodextrin Glucanotransferase and Amyloglucosidase |
| title |
Enzymatic Synthesis of a Novel Pterostilbene α-Glucoside by the Combination of Cyclodextrin Glucanotransferase and Amyloglucosidase |
| spellingShingle |
Enzymatic Synthesis of a Novel Pterostilbene α-Glucoside by the Combination of Cyclodextrin Glucanotransferase and Amyloglucosidase González-Alfonso, José L. Polyphenols Glycosylation Stilbenes Pterostilbene Cyclodextrin glycosyltransferases Enzymatic glucosylation Amyloglucosidase |
| title_short |
Enzymatic Synthesis of a Novel Pterostilbene α-Glucoside by the Combination of Cyclodextrin Glucanotransferase and Amyloglucosidase |
| title_full |
Enzymatic Synthesis of a Novel Pterostilbene α-Glucoside by the Combination of Cyclodextrin Glucanotransferase and Amyloglucosidase |
| title_fullStr |
Enzymatic Synthesis of a Novel Pterostilbene α-Glucoside by the Combination of Cyclodextrin Glucanotransferase and Amyloglucosidase |
| title_full_unstemmed |
Enzymatic Synthesis of a Novel Pterostilbene α-Glucoside by the Combination of Cyclodextrin Glucanotransferase and Amyloglucosidase |
| title_sort |
Enzymatic Synthesis of a Novel Pterostilbene α-Glucoside by the Combination of Cyclodextrin Glucanotransferase and Amyloglucosidase |
| dc.creator.none.fl_str_mv |
González-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 Carlos Fernández Lobato, María Plou Gasca, Francisco José |
| author |
González-Alfonso, José L. |
| author_facet |
González-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 Carlos Fernández Lobato, María Plou Gasca, Francisco José |
| author_role |
author |
| author2 |
Rodrigo-Frutos, David Belmonte-Reche, Efres Peñalver, Pablo Poveda, Ana Jiménez-Barbero, Jesús Ballesteros Olmo, Antonio Hirose, Yoshihiko Polaina Molina, Julio Morales, Juan Carlos Fernández Lobato, María Plou Gasca, Francisco José |
| author2_role |
author author author author author author author author author author author |
| dc.contributor.none.fl_str_mv |
Ministerio de Economía y Competitividad (España) Consejo Superior de Investigaciones Científicas [https://ror.org/02gfc7t72] |
| dc.subject.none.fl_str_mv |
Polyphenols Glycosylation Stilbenes Pterostilbene Cyclodextrin glycosyltransferases Enzymatic glucosylation Amyloglucosidase |
| topic |
Polyphenols Glycosylation Stilbenes Pterostilbene Cyclodextrin glycosyltransferases Enzymatic glucosylation Amyloglucosidase |
| description |
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. |
| publishDate |
2018 |
| dc.date.none.fl_str_mv |
2018 2018 2018 |
| dc.type.none.fl_str_mv |
info:eu-repo/semantics/article http://purl.org/coar/resource_type/c_6501 Publisher's version info:eu-repo/semantics/publishedVersion |
| format |
article |
| status_str |
publishedVersion |
| dc.identifier.none.fl_str_mv |
http://hdl.handle.net/10261/165157 |
| url |
http://hdl.handle.net/10261/165157 |
| dc.language.none.fl_str_mv |
Inglés |
| language_invalid_str_mv |
Inglés |
| dc.relation.none.fl_str_mv |
#PLACEHOLDER_PARENT_METADATA_VALUE# #PLACEHOLDER_PARENT_METADATA_VALUE# info:eu-repo/grantAgreement/MINECO/Plan Estatal de Investigación Científica y Técnica y de Innovación 2013-2016/BIO2016-76601-C3-1-R info:eu-repo/grantAgreement/MINECO/Plan Estatal de Investigación Científica y Técnica y de Innovación 2013-2016/BIO2016-76601-C3-3-R http://dx.doi.org/10.3390/molecules23061271 Sí |
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info:eu-repo/semantics/openAccess |
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openAccess |
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Multidisciplinary Digital Publishing Institute |
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Multidisciplinary Digital Publishing Institute |
| dc.source.none.fl_str_mv |
reponame:DIGITAL.CSIC. Repositorio Institucional del CSIC instname:Consejo Superior de Investigaciones Científicas (CSIC) |
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Consejo Superior de Investigaciones Científicas (CSIC) |
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DIGITAL.CSIC. Repositorio Institucional del CSIC |
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DIGITAL.CSIC. Repositorio Institucional del CSIC |
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1869411196705177600 |
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15,198674 |