Transglycosylation of steviol glycosides and rebaudioside a: Synthesis optimization, structural analysis and sensory profiles

Autores
Muñoz Labrador, Ana; Azcarate, Silvana Mariela; Lebrón Aguilar, Rosa; Quintanilla López, Jesús E.; Galindo Iranzo, Plácido; Kolida, Sofia; Methven, Lisa; Rastall, Robert A.; Moreno, F. Javier; Hernandez Hernandez, Oswaldo
Año de publicación
2020
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
To improve flavor profiles, three cyclodextrin glucosyltransferases (CGTases) from different bacteriological sources, Paenibacillus macerans, Geobacillus sp. and Thermoanaerobacter sp., were used with an extract of steviol glycosides (SVglys) and rebaudioside A (RebA) as acceptor substrates in two parallel sets of reactions. A central composite experimental design was employed to maximize the concentration of glucosylated species synthesized, considering temperature, pH, time of reaction, enzymatic activity, maltodextrin concentration and SVglys/RebA concentration as experimental factors, together with their interactions. Liquid chromatography coupled to a diode-array detector (LC-DAD), liquid chromatography-mass spectrometry (LC-ESI-MS) and matrix-assisted laser desorption/ionization time-of-flight mass spectrometry (MALDI-TOF-MS) were used to characterize and identify the chemical structures obtained along the optimization. To assess the impact on the sensory properties, a sensory analysis was carried out with a group of panelists that evaluated up to 16 sensorial attributes. CGTase transglucosylation of the C-13 and/or C-19 led to the addition of up to 11 glucose units to the steviol aglycone, which meant the achievement of enhanced sensory profiles due to a diminution of bitterness and licorice appreciations. The outcome herein obtained supposes the development of new potential alternatives to replace free sugars with low-calorie sweeteners with added health benefits.
Fil: Muñoz Labrador, Ana. Universidad Autónoma de Madrid; España. Consejo Superior de Investigaciones Científicas; España
Fil: Azcarate, Silvana Mariela. Universidad Nacional de La Pampa. Facultad de Ciencias Exactas y Naturales; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Fil: Lebrón Aguilar, Rosa. Institute of Physical Chemistry ‘Rocasolano’; España. Consejo Superior de Investigaciones Científicas; España
Fil: Quintanilla López, Jesús E.. Institute of Physical Chemistry ‘Rocasolano’; España. Consejo Superior de Investigaciones Científicas; España
Fil: Galindo Iranzo, Plácido. Institute of Physical Chemistry ‘Rocasolano’; España. Consejo Superior de Investigaciones Científicas; España
Fil: Kolida, Sofia. OptiBiotix Health PLC; Reino Unido
Fil: Methven, Lisa. University of Reading; Reino Unido
Fil: Rastall, Robert A.. University of Reading; Reino Unido
Fil: Moreno, F. Javier. Universidad Autónoma de Madrid; España. Consejo Superior de Investigaciones Científicas; España
Fil: Hernandez Hernandez, Oswaldo. Universidad Autónoma de Madrid; España. Consejo Superior de Investigaciones Científicas; España
Materia
SWEETENERS
CGTASE
DESIGN OF EXPERIMENT
GLYCOSYLATION
LICORICE
BITTERNESS
STEVIOL GLYCOSIDES
REBAUDIOSIDE A
STEVIA REBAUDIANA
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/162553
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/162553
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Transglycosylation of steviol glycosides and rebaudioside a: Synthesis optimization, structural analysis and sensory profilesMuñoz Labrador, AnaAzcarate, Silvana MarielaLebrón Aguilar, RosaQuintanilla López, Jesús E.Galindo Iranzo, PlácidoKolida, SofiaMethven, LisaRastall, Robert A.Moreno, F. JavierHernandez Hernandez, OswaldoSWEETENERSCGTASEDESIGN OF EXPERIMENTGLYCOSYLATIONLICORICEBITTERNESSSTEVIOL GLYCOSIDESREBAUDIOSIDE ASTEVIA REBAUDIANAhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1To improve flavor profiles, three cyclodextrin glucosyltransferases (CGTases) from different bacteriological sources, Paenibacillus macerans, Geobacillus sp. and Thermoanaerobacter sp., were used with an extract of steviol glycosides (SVglys) and rebaudioside A (RebA) as acceptor substrates in two parallel sets of reactions. A central composite experimental design was employed to maximize the concentration of glucosylated species synthesized, considering temperature, pH, time of reaction, enzymatic activity, maltodextrin concentration and SVglys/RebA concentration as experimental factors, together with their interactions. Liquid chromatography coupled to a diode-array detector (LC-DAD), liquid chromatography-mass spectrometry (LC-ESI-MS) and matrix-assisted laser desorption/ionization time-of-flight mass spectrometry (MALDI-TOF-MS) were used to characterize and identify the chemical structures obtained along the optimization. To assess the impact on the sensory properties, a sensory analysis was carried out with a group of panelists that evaluated up to 16 sensorial attributes. CGTase transglucosylation of the C-13 and/or C-19 led to the addition of up to 11 glucose units to the steviol aglycone, which meant the achievement of enhanced sensory profiles due to a diminution of bitterness and licorice appreciations. The outcome herein obtained supposes the development of new potential alternatives to replace free sugars with low-calorie sweeteners with added health benefits.Fil: Muñoz Labrador, Ana. Universidad Autónoma de Madrid; España. Consejo Superior de Investigaciones Científicas; EspañaFil: Azcarate, Silvana Mariela. Universidad Nacional de La Pampa. Facultad de Ciencias Exactas y Naturales; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; ArgentinaFil: Lebrón Aguilar, Rosa. Institute of Physical Chemistry ‘Rocasolano’; España. Consejo Superior de Investigaciones Científicas; EspañaFil: Quintanilla López, Jesús E.. Institute of Physical Chemistry ‘Rocasolano’; España. Consejo Superior de Investigaciones Científicas; EspañaFil: Galindo Iranzo, Plácido. Institute of Physical Chemistry ‘Rocasolano’; España. Consejo Superior de Investigaciones Científicas; EspañaFil: Kolida, Sofia. OptiBiotix Health PLC; Reino UnidoFil: Methven, Lisa. University of Reading; Reino UnidoFil: Rastall, Robert A.. University of Reading; Reino UnidoFil: Moreno, F. Javier. Universidad Autónoma de Madrid; España. Consejo Superior de Investigaciones Científicas; EspañaFil: Hernandez Hernandez, Oswaldo. Universidad Autónoma de Madrid; España. Consejo Superior de Investigaciones Científicas; EspañaMultidisciplinary Digital Publishing Institute2020-11info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/162553Muñoz Labrador, Ana; Azcarate, Silvana Mariela; Lebrón Aguilar, Rosa; Quintanilla López, Jesús E.; Galindo Iranzo, Plácido; et al.; Transglycosylation of steviol glycosides and rebaudioside a: Synthesis optimization, structural analysis and sensory profiles; Multidisciplinary Digital Publishing Institute; Foods; 9; 1753; 11-2020; 1-152304-8158CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/https://www.mdpi.com/2304-8158/9/12/1753info:eu-repo/semantics/altIdentifier/doi/10.3390/foods9121753info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T10:02:11Zoai:ri.conicet.gov.ar:11336/162553instacron:CONICETInstitucionalhttp://ri.conicet.gov.ar/Organismo científico-tecnológicoNo correspondehttp://ri.conicet.gov.ar/oai/requestdasensio@conicet.gov.ar; lcarlino@conicet.gov.arArgentinaNo correspondeNo correspondeNo correspondeopendoar:34982025-09-29 10:02:11.549CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Transglycosylation of steviol glycosides and rebaudioside a: Synthesis optimization, structural analysis and sensory profiles
title Transglycosylation of steviol glycosides and rebaudioside a: Synthesis optimization, structural analysis and sensory profiles
spellingShingle Transglycosylation of steviol glycosides and rebaudioside a: Synthesis optimization, structural analysis and sensory profiles
Muñoz Labrador, Ana
SWEETENERS
CGTASE
DESIGN OF EXPERIMENT
GLYCOSYLATION
LICORICE
BITTERNESS
STEVIOL GLYCOSIDES
REBAUDIOSIDE A
STEVIA REBAUDIANA
title_short Transglycosylation of steviol glycosides and rebaudioside a: Synthesis optimization, structural analysis and sensory profiles
title_full Transglycosylation of steviol glycosides and rebaudioside a: Synthesis optimization, structural analysis and sensory profiles
title_fullStr Transglycosylation of steviol glycosides and rebaudioside a: Synthesis optimization, structural analysis and sensory profiles
title_full_unstemmed Transglycosylation of steviol glycosides and rebaudioside a: Synthesis optimization, structural analysis and sensory profiles
title_sort Transglycosylation of steviol glycosides and rebaudioside a: Synthesis optimization, structural analysis and sensory profiles
dc.creator.none.fl_str_mv Muñoz Labrador, Ana
Azcarate, Silvana Mariela
Lebrón Aguilar, Rosa
Quintanilla López, Jesús E.
Galindo Iranzo, Plácido
Kolida, Sofia
Methven, Lisa
Rastall, Robert A.
Moreno, F. Javier
Hernandez Hernandez, Oswaldo
author Muñoz Labrador, Ana
author_facet Muñoz Labrador, Ana
Azcarate, Silvana Mariela
Lebrón Aguilar, Rosa
Quintanilla López, Jesús E.
Galindo Iranzo, Plácido
Kolida, Sofia
Methven, Lisa
Rastall, Robert A.
Moreno, F. Javier
Hernandez Hernandez, Oswaldo
author_role author
author2 Azcarate, Silvana Mariela
Lebrón Aguilar, Rosa
Quintanilla López, Jesús E.
Galindo Iranzo, Plácido
Kolida, Sofia
Methven, Lisa
Rastall, Robert A.
Moreno, F. Javier
Hernandez Hernandez, Oswaldo
author2_role author
author
author
author
author
author
author
author
author
dc.subject.none.fl_str_mv SWEETENERS
CGTASE
DESIGN OF EXPERIMENT
GLYCOSYLATION
LICORICE
BITTERNESS
STEVIOL GLYCOSIDES
REBAUDIOSIDE A
STEVIA REBAUDIANA
topic SWEETENERS
CGTASE
DESIGN OF EXPERIMENT
GLYCOSYLATION
LICORICE
BITTERNESS
STEVIOL GLYCOSIDES
REBAUDIOSIDE A
STEVIA REBAUDIANA
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv To improve flavor profiles, three cyclodextrin glucosyltransferases (CGTases) from different bacteriological sources, Paenibacillus macerans, Geobacillus sp. and Thermoanaerobacter sp., were used with an extract of steviol glycosides (SVglys) and rebaudioside A (RebA) as acceptor substrates in two parallel sets of reactions. A central composite experimental design was employed to maximize the concentration of glucosylated species synthesized, considering temperature, pH, time of reaction, enzymatic activity, maltodextrin concentration and SVglys/RebA concentration as experimental factors, together with their interactions. Liquid chromatography coupled to a diode-array detector (LC-DAD), liquid chromatography-mass spectrometry (LC-ESI-MS) and matrix-assisted laser desorption/ionization time-of-flight mass spectrometry (MALDI-TOF-MS) were used to characterize and identify the chemical structures obtained along the optimization. To assess the impact on the sensory properties, a sensory analysis was carried out with a group of panelists that evaluated up to 16 sensorial attributes. CGTase transglucosylation of the C-13 and/or C-19 led to the addition of up to 11 glucose units to the steviol aglycone, which meant the achievement of enhanced sensory profiles due to a diminution of bitterness and licorice appreciations. The outcome herein obtained supposes the development of new potential alternatives to replace free sugars with low-calorie sweeteners with added health benefits.
Fil: Muñoz Labrador, Ana. Universidad Autónoma de Madrid; España. Consejo Superior de Investigaciones Científicas; España
Fil: Azcarate, Silvana Mariela. Universidad Nacional de La Pampa. Facultad de Ciencias Exactas y Naturales; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Fil: Lebrón Aguilar, Rosa. Institute of Physical Chemistry ‘Rocasolano’; España. Consejo Superior de Investigaciones Científicas; España
Fil: Quintanilla López, Jesús E.. Institute of Physical Chemistry ‘Rocasolano’; España. Consejo Superior de Investigaciones Científicas; España
Fil: Galindo Iranzo, Plácido. Institute of Physical Chemistry ‘Rocasolano’; España. Consejo Superior de Investigaciones Científicas; España
Fil: Kolida, Sofia. OptiBiotix Health PLC; Reino Unido
Fil: Methven, Lisa. University of Reading; Reino Unido
Fil: Rastall, Robert A.. University of Reading; Reino Unido
Fil: Moreno, F. Javier. Universidad Autónoma de Madrid; España. Consejo Superior de Investigaciones Científicas; España
Fil: Hernandez Hernandez, Oswaldo. Universidad Autónoma de Madrid; España. Consejo Superior de Investigaciones Científicas; España
description To improve flavor profiles, three cyclodextrin glucosyltransferases (CGTases) from different bacteriological sources, Paenibacillus macerans, Geobacillus sp. and Thermoanaerobacter sp., were used with an extract of steviol glycosides (SVglys) and rebaudioside A (RebA) as acceptor substrates in two parallel sets of reactions. A central composite experimental design was employed to maximize the concentration of glucosylated species synthesized, considering temperature, pH, time of reaction, enzymatic activity, maltodextrin concentration and SVglys/RebA concentration as experimental factors, together with their interactions. Liquid chromatography coupled to a diode-array detector (LC-DAD), liquid chromatography-mass spectrometry (LC-ESI-MS) and matrix-assisted laser desorption/ionization time-of-flight mass spectrometry (MALDI-TOF-MS) were used to characterize and identify the chemical structures obtained along the optimization. To assess the impact on the sensory properties, a sensory analysis was carried out with a group of panelists that evaluated up to 16 sensorial attributes. CGTase transglucosylation of the C-13 and/or C-19 led to the addition of up to 11 glucose units to the steviol aglycone, which meant the achievement of enhanced sensory profiles due to a diminution of bitterness and licorice appreciations. The outcome herein obtained supposes the development of new potential alternatives to replace free sugars with low-calorie sweeteners with added health benefits.
publishDate 2020
dc.date.none.fl_str_mv 2020-11
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
http://purl.org/coar/resource_type/c_6501
info:ar-repo/semantics/articulo
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/11336/162553
Muñoz Labrador, Ana; Azcarate, Silvana Mariela; Lebrón Aguilar, Rosa; Quintanilla López, Jesús E.; Galindo Iranzo, Plácido; et al.; Transglycosylation of steviol glycosides and rebaudioside a: Synthesis optimization, structural analysis and sensory profiles; Multidisciplinary Digital Publishing Institute; Foods; 9; 1753; 11-2020; 1-15
2304-8158
CONICET Digital
CONICET
url http://hdl.handle.net/11336/162553
identifier_str_mv Muñoz Labrador, Ana; Azcarate, Silvana Mariela; Lebrón Aguilar, Rosa; Quintanilla López, Jesús E.; Galindo Iranzo, Plácido; et al.; Transglycosylation of steviol glycosides and rebaudioside a: Synthesis optimization, structural analysis and sensory profiles; Multidisciplinary Digital Publishing Institute; Foods; 9; 1753; 11-2020; 1-15
2304-8158
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/url/https://www.mdpi.com/2304-8158/9/12/1753
info:eu-repo/semantics/altIdentifier/doi/10.3390/foods9121753
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by/2.5/ar/
dc.format.none.fl_str_mv application/pdf
application/pdf
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:CONICET Digital (CONICET)
instname:Consejo Nacional de Investigaciones Científicas y Técnicas
reponame_str CONICET Digital (CONICET)
collection CONICET Digital (CONICET)
instname_str Consejo Nacional de Investigaciones Científicas y Técnicas
repository.name.fl_str_mv CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicas
repository.mail.fl_str_mv dasensio@conicet.gov.ar; lcarlino@conicet.gov.ar
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score 13.069144

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