Biocatalytic preparation of alkyl esters of citrus flavanone glucoside prunin in organic media

Autores
Celiz, Gustavo; Daz, Mirta Elizabeth
Año de publicación
2010
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
The biocatalytic preparation of alkyl esters of prunin, a flavanone glucoside derivative of citric flavonoid naringin, was performed in organic media using two commercial immobilized lipases: Novozym 435 (Candida antarctica lipase B immobilized on an acrylic resin) and Lipozyme RM IM (Rhizomucor miehei lipase immobilized on an anion exchange resin). The influence of several reaction parameters on the performance and regioselectivity of the biocatalytic process was investigated using four solvents (acetone, acetonitrile, tetrahydrofurane and t-butanol) and vinyl laurate as a donor. The biocatalytic modification of prunin was strongly dependant on the solvent, the molar ratio of the substrates, the enzyme and the chain length of the donor. The acylation was highly regioselective, obtaining 6"-O-acyl monoesters except when the donor was vinyl acetate in which case a diester seemed to be formed. Novozym 435 proved to be a more efficient biocatalyst than Lipozyme RM IM. In acetone and acetonitrile, derivatives with a 100% conversion yield were synthesized after only 6 h of reaction at 50 °C. The modified derivatives preserved the antiradical activity of the flavanone glucoside and their solubility notably increased in the hydrophobic medium 1-octanol.
Fil: Celiz, Gustavo. Universidad Nacional de Salta. Facultad de Ciencias Exactas; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Salta. Instituto de Investigaciones para la Industria Química. Universidad Nacional de Salta. Facultad de Ingeniería. Instituto de Investigaciones para la Industria Química; Argentina
Fil: Daz, Mirta Elizabeth. Universidad Nacional de Salta. Facultad de Ciencias Exactas; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Salta. Instituto de Investigaciones para la Industria Química. Universidad Nacional de Salta. Facultad de Ingeniería. Instituto de Investigaciones para la Industria Química; Argentina
Materia
LIPASES
FLAVONOIDS
FLAVANONES
PRUNIN
NARINGIN
CITRUS
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/276955
Acceder
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network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Biocatalytic preparation of alkyl esters of citrus flavanone glucoside prunin in organic mediaCeliz, GustavoDaz, Mirta ElizabethLIPASESFLAVONOIDSFLAVANONESPRUNINNARINGINCITRUShttps://purl.org/becyt/ford/2.9https://purl.org/becyt/ford/2The biocatalytic preparation of alkyl esters of prunin, a flavanone glucoside derivative of citric flavonoid naringin, was performed in organic media using two commercial immobilized lipases: Novozym 435 (Candida antarctica lipase B immobilized on an acrylic resin) and Lipozyme RM IM (Rhizomucor miehei lipase immobilized on an anion exchange resin). The influence of several reaction parameters on the performance and regioselectivity of the biocatalytic process was investigated using four solvents (acetone, acetonitrile, tetrahydrofurane and t-butanol) and vinyl laurate as a donor. The biocatalytic modification of prunin was strongly dependant on the solvent, the molar ratio of the substrates, the enzyme and the chain length of the donor. The acylation was highly regioselective, obtaining 6"-O-acyl monoesters except when the donor was vinyl acetate in which case a diester seemed to be formed. Novozym 435 proved to be a more efficient biocatalyst than Lipozyme RM IM. In acetone and acetonitrile, derivatives with a 100% conversion yield were synthesized after only 6 h of reaction at 50 °C. The modified derivatives preserved the antiradical activity of the flavanone glucoside and their solubility notably increased in the hydrophobic medium 1-octanol.Fil: Celiz, Gustavo. Universidad Nacional de Salta. Facultad de Ciencias Exactas; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Salta. Instituto de Investigaciones para la Industria Química. Universidad Nacional de Salta. Facultad de Ingeniería. Instituto de Investigaciones para la Industria Química; ArgentinaFil: Daz, Mirta Elizabeth. Universidad Nacional de Salta. Facultad de Ciencias Exactas; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Salta. Instituto de Investigaciones para la Industria Química. Universidad Nacional de Salta. Facultad de Ingeniería. Instituto de Investigaciones para la Industria Química; ArgentinaElsevier2010-01info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/276955Celiz, Gustavo; Daz, Mirta Elizabeth; Biocatalytic preparation of alkyl esters of citrus flavanone glucoside prunin in organic media; Elsevier; Process Biochemistry; 46; 1; 1-2010; 94-1001359-5113CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/http://www.sciencedirect.com/science/article/pii/S1359511310002874info:eu-repo/semantics/altIdentifier/doi/10.1016/j.procbio.2010.07.022info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2026-01-08T12:58:53Zoai:ri.conicet.gov.ar:11336/276955instacron: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:34982026-01-08 12:58:54.168CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Biocatalytic preparation of alkyl esters of citrus flavanone glucoside prunin in organic media
title Biocatalytic preparation of alkyl esters of citrus flavanone glucoside prunin in organic media
spellingShingle Biocatalytic preparation of alkyl esters of citrus flavanone glucoside prunin in organic media
Celiz, Gustavo
LIPASES
FLAVONOIDS
FLAVANONES
PRUNIN
NARINGIN
CITRUS
title_short Biocatalytic preparation of alkyl esters of citrus flavanone glucoside prunin in organic media
title_full Biocatalytic preparation of alkyl esters of citrus flavanone glucoside prunin in organic media
title_fullStr Biocatalytic preparation of alkyl esters of citrus flavanone glucoside prunin in organic media
title_full_unstemmed Biocatalytic preparation of alkyl esters of citrus flavanone glucoside prunin in organic media
title_sort Biocatalytic preparation of alkyl esters of citrus flavanone glucoside prunin in organic media
dc.creator.none.fl_str_mv Celiz, Gustavo
Daz, Mirta Elizabeth
author Celiz, Gustavo
author_facet Celiz, Gustavo
Daz, Mirta Elizabeth
author_role author
author2 Daz, Mirta Elizabeth
author2_role author
dc.subject.none.fl_str_mv LIPASES
FLAVONOIDS
FLAVANONES
PRUNIN
NARINGIN
CITRUS
topic LIPASES
FLAVONOIDS
FLAVANONES
PRUNIN
NARINGIN
CITRUS
purl_subject.fl_str_mv https://purl.org/becyt/ford/2.9
https://purl.org/becyt/ford/2
dc.description.none.fl_txt_mv The biocatalytic preparation of alkyl esters of prunin, a flavanone glucoside derivative of citric flavonoid naringin, was performed in organic media using two commercial immobilized lipases: Novozym 435 (Candida antarctica lipase B immobilized on an acrylic resin) and Lipozyme RM IM (Rhizomucor miehei lipase immobilized on an anion exchange resin). The influence of several reaction parameters on the performance and regioselectivity of the biocatalytic process was investigated using four solvents (acetone, acetonitrile, tetrahydrofurane and t-butanol) and vinyl laurate as a donor. The biocatalytic modification of prunin was strongly dependant on the solvent, the molar ratio of the substrates, the enzyme and the chain length of the donor. The acylation was highly regioselective, obtaining 6"-O-acyl monoesters except when the donor was vinyl acetate in which case a diester seemed to be formed. Novozym 435 proved to be a more efficient biocatalyst than Lipozyme RM IM. In acetone and acetonitrile, derivatives with a 100% conversion yield were synthesized after only 6 h of reaction at 50 °C. The modified derivatives preserved the antiradical activity of the flavanone glucoside and their solubility notably increased in the hydrophobic medium 1-octanol.
Fil: Celiz, Gustavo. Universidad Nacional de Salta. Facultad de Ciencias Exactas; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Salta. Instituto de Investigaciones para la Industria Química. Universidad Nacional de Salta. Facultad de Ingeniería. Instituto de Investigaciones para la Industria Química; Argentina
Fil: Daz, Mirta Elizabeth. Universidad Nacional de Salta. Facultad de Ciencias Exactas; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Salta. Instituto de Investigaciones para la Industria Química. Universidad Nacional de Salta. Facultad de Ingeniería. Instituto de Investigaciones para la Industria Química; Argentina
description The biocatalytic preparation of alkyl esters of prunin, a flavanone glucoside derivative of citric flavonoid naringin, was performed in organic media using two commercial immobilized lipases: Novozym 435 (Candida antarctica lipase B immobilized on an acrylic resin) and Lipozyme RM IM (Rhizomucor miehei lipase immobilized on an anion exchange resin). The influence of several reaction parameters on the performance and regioselectivity of the biocatalytic process was investigated using four solvents (acetone, acetonitrile, tetrahydrofurane and t-butanol) and vinyl laurate as a donor. The biocatalytic modification of prunin was strongly dependant on the solvent, the molar ratio of the substrates, the enzyme and the chain length of the donor. The acylation was highly regioselective, obtaining 6"-O-acyl monoesters except when the donor was vinyl acetate in which case a diester seemed to be formed. Novozym 435 proved to be a more efficient biocatalyst than Lipozyme RM IM. In acetone and acetonitrile, derivatives with a 100% conversion yield were synthesized after only 6 h of reaction at 50 °C. The modified derivatives preserved the antiradical activity of the flavanone glucoside and their solubility notably increased in the hydrophobic medium 1-octanol.
publishDate 2010
dc.date.none.fl_str_mv 2010-01
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/11336/276955
Celiz, Gustavo; Daz, Mirta Elizabeth; Biocatalytic preparation of alkyl esters of citrus flavanone glucoside prunin in organic media; Elsevier; Process Biochemistry; 46; 1; 1-2010; 94-100
1359-5113
CONICET Digital
CONICET
url http://hdl.handle.net/11336/276955
identifier_str_mv Celiz, Gustavo; Daz, Mirta Elizabeth; Biocatalytic preparation of alkyl esters of citrus flavanone glucoside prunin in organic media; Elsevier; Process Biochemistry; 46; 1; 1-2010; 94-100
1359-5113
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/url/http://www.sciencedirect.com/science/article/pii/S1359511310002874
info:eu-repo/semantics/altIdentifier/doi/10.1016/j.procbio.2010.07.022
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
dc.format.none.fl_str_mv application/pdf
application/pdf
application/pdf
dc.publisher.none.fl_str_mv Elsevier
publisher.none.fl_str_mv Elsevier
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 12.747614

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