Efficient α-glucosylation of epigallocatechin gallate catalyzed by cyclodextrin glucanotransferase from Thermoanaerobacter sp.

The glycosylation of plant polyphenols may modulate their solubility and bioavailability, and protect these molecules from oxygen, light degradation and during gastrointestinal transit. In this work, the synthesis of various α-glucosyl derivatives of (‒)-epigallocatechin gallate (EGCG), the predomin...

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Authors: González-Alfonso, José L., Leemans, Laura, Poveda, Ana, Jiménez-Barbero, Jesús, Plou Gasca, Francisco José
Format: article
Status:Versión aceptada para publicación
Publication Date:2018
Country:España
Institution:Consejo Superior de Investigaciones Científicas (CSIC)
Repository:DIGITAL.CSIC. Repositorio Institucional del CSIC
OAI Identifier:oai:digital.csic.es:10261/167290
Online Access:http://hdl.handle.net/10261/167290
Access Level:Open access
Keyword:Glycosylation
Tea polyphenols
Antioxidants
Catechins
Cyclodextrin glucosyltransferase
Enzymatic glucosylation
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spelling Efficient α-glucosylation of epigallocatechin gallate catalyzed by cyclodextrin glucanotransferase from Thermoanaerobacter sp.González-Alfonso, José L.Leemans, LauraPoveda, AnaJiménez-Barbero, JesúsPlou Gasca, Francisco JoséGlycosylationTea polyphenolsAntioxidantsCatechinsCyclodextrin glucosyltransferaseEnzymatic glucosylationThe glycosylation of plant polyphenols may modulate their solubility and bioavailability, and protect these molecules from oxygen, light degradation and during gastrointestinal transit. In this work, the synthesis of various α-glucosyl derivatives of (‒)-epigallocatechin gallate (EGCG), the predominant catechin in green tea, was performed in water at 50 °C by a transglycosylation reaction catalyzed by cyclodextrin glycosyltransferase (CGTase) from Thermoanaerobacter sp. The molecular weight of reaction products was determined by HPLC-MS. Using hydrolyzed potato starch as glucosyl donor, two main monoglucosides were obtained with conversion yields of 58% and 13%, respectively. The products were isolated and chemically characterized by combining 2D-NMR methods. The major derivative was epigallocatechin gallate 3’-O-α-D-glucopyranoside (1) and the minor epigallocatechin gallate 7-O-α-D-glucopyranoside (2).This work was supported by a grants from the Spanish Ministry of Economy and Competitiveness (Grants BIO2013-48779-C4-1 and BIO2016-76601-C3-1-R). We thank the support of COST-Action CM1303 on Systems Biocatalysts.Peer reviewedAmerican Chemical SocietyMinisterio de Economía y Competitividad (España)European Cooperation in Science and TechnologyConsejo Superior de Investigaciones Científicas [https://ror.org/02gfc7t72]201820182018info:eu-repo/semantics/articlehttp://purl.org/coar/resource_type/c_6501Postprintinfo:eu-repo/semantics/acceptedVersionhttp://hdl.handle.net/10261/167290reponame: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 2013-2016BIO2013-48779-C4-1-R/info:eu-repo/grantAgreement/MINECO/Plan Estatal de Investigación Científica y Técnica y de Innovación 2013-2016BIO2016-76601-C3-1-R/http://dx.doi.org/10.1021/acs.jafc.8b02143Síinfo:eu-repo/semantics/openAccessoai:digital.csic.es:10261/1672902026-05-22T06:33:51Z
dc.title.none.fl_str_mv Efficient α-glucosylation of epigallocatechin gallate catalyzed by cyclodextrin glucanotransferase from Thermoanaerobacter sp.
title Efficient α-glucosylation of epigallocatechin gallate catalyzed by cyclodextrin glucanotransferase from Thermoanaerobacter sp.
spellingShingle Efficient α-glucosylation of epigallocatechin gallate catalyzed by cyclodextrin glucanotransferase from Thermoanaerobacter sp.
González-Alfonso, José L.
Glycosylation
Tea polyphenols
Antioxidants
Catechins
Cyclodextrin glucosyltransferase
Enzymatic glucosylation
title_short Efficient α-glucosylation of epigallocatechin gallate catalyzed by cyclodextrin glucanotransferase from Thermoanaerobacter sp.
title_full Efficient α-glucosylation of epigallocatechin gallate catalyzed by cyclodextrin glucanotransferase from Thermoanaerobacter sp.
title_fullStr Efficient α-glucosylation of epigallocatechin gallate catalyzed by cyclodextrin glucanotransferase from Thermoanaerobacter sp.
title_full_unstemmed Efficient α-glucosylation of epigallocatechin gallate catalyzed by cyclodextrin glucanotransferase from Thermoanaerobacter sp.
title_sort Efficient α-glucosylation of epigallocatechin gallate catalyzed by cyclodextrin glucanotransferase from Thermoanaerobacter sp.
dc.creator.none.fl_str_mv González-Alfonso, José L.
Leemans, Laura
Poveda, Ana
Jiménez-Barbero, Jesús
Plou Gasca, Francisco José
author González-Alfonso, José L.
author_facet González-Alfonso, José L.
Leemans, Laura
Poveda, Ana
Jiménez-Barbero, Jesús
Plou Gasca, Francisco José
author_role author
author2 Leemans, Laura
Poveda, Ana
Jiménez-Barbero, Jesús
Plou Gasca, Francisco José
author2_role author
author
author
author
dc.contributor.none.fl_str_mv Ministerio de Economía y Competitividad (España)
European Cooperation in Science and Technology
Consejo Superior de Investigaciones Científicas [https://ror.org/02gfc7t72]
dc.subject.none.fl_str_mv Glycosylation
Tea polyphenols
Antioxidants
Catechins
Cyclodextrin glucosyltransferase
Enzymatic glucosylation
topic Glycosylation
Tea polyphenols
Antioxidants
Catechins
Cyclodextrin glucosyltransferase
Enzymatic glucosylation
description The glycosylation of plant polyphenols may modulate their solubility and bioavailability, and protect these molecules from oxygen, light degradation and during gastrointestinal transit. In this work, the synthesis of various α-glucosyl derivatives of (‒)-epigallocatechin gallate (EGCG), the predominant catechin in green tea, was performed in water at 50 °C by a transglycosylation reaction catalyzed by cyclodextrin glycosyltransferase (CGTase) from Thermoanaerobacter sp. The molecular weight of reaction products was determined by HPLC-MS. Using hydrolyzed potato starch as glucosyl donor, two main monoglucosides were obtained with conversion yields of 58% and 13%, respectively. The products were isolated and chemically characterized by combining 2D-NMR methods. The major derivative was epigallocatechin gallate 3’-O-α-D-glucopyranoside (1) and the minor epigallocatechin gallate 7-O-α-D-glucopyranoside (2).
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
Postprint
info:eu-repo/semantics/acceptedVersion
format article
status_str acceptedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/10261/167290
url http://hdl.handle.net/10261/167290
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 2013-2016BIO2013-48779-C4-1-R/
info:eu-repo/grantAgreement/MINECO/Plan Estatal de Investigación Científica y Técnica y de Innovación 2013-2016BIO2016-76601-C3-1-R/
http://dx.doi.org/10.1021/acs.jafc.8b02143
Sí
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.publisher.none.fl_str_mv American Chemical Society
publisher.none.fl_str_mv American Chemical Society
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 15,812429

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