Optimization of regioselective α-Glucosylation of hesperetin catalyzed by cyclodextrin glucanotransferase

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 monoglucosyl...

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Autores: González-Alfonso, José L., Míguez, Noa, Padilla, J. Daniel, Leemans, Laura, Poveda, Ana, Jiménez-Barbero, Jesús, Ballesteros Olmo, Antonio, Sandoval, Georgina, Plou Gasca, Francisco José
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:10261/172238
Acceso en línea:http://hdl.handle.net/10261/172238
Access Level:acceso abierto
Palabra clave:Polyphenols
Glycosylation
Flavonoids
Flavanones
Cyclodextrin glucosyltransferase
Enzymatic glucosylation
Hesperidin
Hesperetin
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repository_id_str
spelling Optimization of regioselective α-Glucosylation of hesperetin catalyzed by cyclodextrin glucanotransferaseGonzález-Alfonso, José L.Míguez, NoaPadilla, J. DanielLeemans, LauraPoveda, AnaJiménez-Barbero, JesúsBallesteros Olmo, AntonioSandoval, GeorginaPlou Gasca, Francisco JoséPolyphenolsGlycosylationFlavonoidsFlavanonesCyclodextrin glucosyltransferaseEnzymatic glucosylationHesperidinHesperetinThe 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.This research was funded by the Spanish Ministry of Economy and Competitiveness (Grant BIO2016-76601-C3-1-R) and the Spanish Ministry of Education (Sabbatical grant to G.S. ref. SB2010-0004).Peer reviewedMultidisciplinary Digital Publishing InstituteMinisterio de Economía y Competitividad (España)Ministerio de Educación (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/10261/172238reponame:DIGITAL.CSIC. Repositorio Institucional del CSICinstname:Consejo Superior de Investigaciones Científicas (CSIC)Inglés#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-Rhttps://doi.org/10.3390/molecules23112885Síinfo:eu-repo/semantics/openAccessoai:digital.csic.es:10261/1722382026-05-22T06:33:51Z
dc.title.none.fl_str_mv Optimization of regioselective α-Glucosylation of hesperetin catalyzed by cyclodextrin glucanotransferase
title Optimization of regioselective α-Glucosylation of hesperetin catalyzed by cyclodextrin glucanotransferase
spellingShingle Optimization of regioselective α-Glucosylation of hesperetin catalyzed by cyclodextrin glucanotransferase
González-Alfonso, José L.
Polyphenols
Glycosylation
Flavonoids
Flavanones
Cyclodextrin glucosyltransferase
Enzymatic glucosylation
Hesperidin
Hesperetin
title_short Optimization of regioselective α-Glucosylation of hesperetin catalyzed by cyclodextrin glucanotransferase
title_full Optimization of regioselective α-Glucosylation of hesperetin catalyzed by cyclodextrin glucanotransferase
title_fullStr Optimization of regioselective α-Glucosylation of hesperetin catalyzed by cyclodextrin glucanotransferase
title_full_unstemmed Optimization of regioselective α-Glucosylation of hesperetin catalyzed by cyclodextrin glucanotransferase
title_sort Optimization of regioselective α-Glucosylation of hesperetin catalyzed by cyclodextrin glucanotransferase
dc.creator.none.fl_str_mv González-Alfonso, José L.
Míguez, Noa
Padilla, J. Daniel
Leemans, Laura
Poveda, Ana
Jiménez-Barbero, Jesús
Ballesteros Olmo, Antonio
Sandoval, Georgina
Plou Gasca, Francisco José
author González-Alfonso, José L.
author_facet González-Alfonso, José L.
Míguez, Noa
Padilla, J. Daniel
Leemans, Laura
Poveda, Ana
Jiménez-Barbero, Jesús
Ballesteros Olmo, Antonio
Sandoval, Georgina
Plou Gasca, Francisco José
author_role author
author2 Míguez, Noa
Padilla, J. Daniel
Leemans, Laura
Poveda, Ana
Jiménez-Barbero, Jesús
Ballesteros Olmo, Antonio
Sandoval, Georgina
Plou Gasca, Francisco José
author2_role author
author
author
author
author
author
author
author
dc.contributor.none.fl_str_mv Ministerio de Economía y Competitividad (España)
Ministerio de Educación (España)
Consejo Superior de Investigaciones Científicas [https://ror.org/02gfc7t72]
dc.subject.none.fl_str_mv Polyphenols
Glycosylation
Flavonoids
Flavanones
Cyclodextrin glucosyltransferase
Enzymatic glucosylation
Hesperidin
Hesperetin
topic Polyphenols
Glycosylation
Flavonoids
Flavanones
Cyclodextrin glucosyltransferase
Enzymatic glucosylation
Hesperidin
Hesperetin
description 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.
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/10261/172238
url http://hdl.handle.net/10261/172238
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.relation.none.fl_str_mv #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
https://doi.org/10.3390/molecules23112885
Sí
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.publisher.none.fl_str_mv Multidisciplinary Digital Publishing Institute
publisher.none.fl_str_mv Multidisciplinary Digital Publishing Institute
dc.source.none.fl_str_mv reponame:DIGITAL.CSIC. Repositorio Institucional del CSIC
instname:Consejo Superior de Investigaciones Científicas (CSIC)
instname_str Consejo Superior de Investigaciones Científicas (CSIC)
reponame_str DIGITAL.CSIC. Repositorio Institucional del CSIC
collection DIGITAL.CSIC. Repositorio Institucional del CSIC
repository.name.fl_str_mv
repository.mail.fl_str_mv
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score 15,811543

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