Synthesis of hesperetin 7-O-glucoside from flavonoids extracted from Citrus waste using both free and immobilized α-l-rhamnosidases

Autores
Celiz, Gustavo; Rodriguez Zotelo, Juan Jesus; Soria, Francisco Fernando; Daz, Mirta Elizabeth
Año de publicación
2015
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
This work was aimed to design alternatives to semi-synthesize hesperetin 7-O-glucoside (HG), a low occurrence natural product, from the flavonoids hesperidin (HES) and neohesperidin (NEO) that can be extracted at large scale from Citrus. To fulfill this objective, the activities of three α-l-rhamnosidases were characterized using both synthetic and natural substrates. Our results indicate that NEO is a good substrate for HG synthesis, mainly because of its solubility in water. Regarding the biocatalysts assessed, all the rhamnosidases exhibited good performances for NEO hydrolysis. Particularly, rhamnosidase from Aspergillus terreus was covalently immobilized onto azide-Dacron magnetized support, activating the support with NaNO2. Immobilized rhamnosidase presented high stability against both thermal denaturation and washing. Based on the results obtained, two methods to obtain HG from NEO are proposed, the first one involving a soluble commercial enzyme, and the second one using the immobilized biocatalyst. Using the latter approach, HG was obtained almost pure at lab-scale, with an overall yield of 93%.
Fil: Celiz, Gustavo. 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: Rodriguez Zotelo, Juan Jesus. 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: Soria, Francisco Fernando. 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. 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
Citrus Flavonoids
Enzymatic Hydrolisis
Rhamnosidases
Hesperetin 7-O-Glucoside
Hesperidin
Neohesperidin
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by-nc-nd/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/22136
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/22136
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Synthesis of hesperetin 7-O-glucoside from flavonoids extracted from Citrus waste using both free and immobilized α-l-rhamnosidasesCeliz, GustavoRodriguez Zotelo, Juan JesusSoria, Francisco FernandoDaz, Mirta ElizabethCitrus FlavonoidsEnzymatic HydrolisisRhamnosidasesHesperetin 7-O-GlucosideHesperidinNeohesperidinhttps://purl.org/becyt/ford/2.9https://purl.org/becyt/ford/2This work was aimed to design alternatives to semi-synthesize hesperetin 7-O-glucoside (HG), a low occurrence natural product, from the flavonoids hesperidin (HES) and neohesperidin (NEO) that can be extracted at large scale from Citrus. To fulfill this objective, the activities of three α-l-rhamnosidases were characterized using both synthetic and natural substrates. Our results indicate that NEO is a good substrate for HG synthesis, mainly because of its solubility in water. Regarding the biocatalysts assessed, all the rhamnosidases exhibited good performances for NEO hydrolysis. Particularly, rhamnosidase from Aspergillus terreus was covalently immobilized onto azide-Dacron magnetized support, activating the support with NaNO2. Immobilized rhamnosidase presented high stability against both thermal denaturation and washing. Based on the results obtained, two methods to obtain HG from NEO are proposed, the first one involving a soluble commercial enzyme, and the second one using the immobilized biocatalyst. Using the latter approach, HG was obtained almost pure at lab-scale, with an overall yield of 93%.Fil: Celiz, Gustavo. 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: Rodriguez Zotelo, Juan Jesus. 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: Soria, Francisco Fernando. 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. 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; ArgentinaElsevier2015-06info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/22136Celiz, Gustavo; Rodriguez Zotelo, Juan Jesus; Soria, Francisco Fernando; Daz, Mirta Elizabeth; Synthesis of hesperetin 7-O-glucoside from flavonoids extracted from Citrus waste using both free and immobilized α-l-rhamnosidases; Elsevier; Biocatalysis and Agricultural Biotechnology; 4; 3; 6-2015; 335-3411878-8181CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1016/j.bcab.2015.06.005info:eu-repo/semantics/altIdentifier/url/http://www.sciencedirect.com/science/article/pii/S1878818115000778info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-nd/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T09:47:25Zoai:ri.conicet.gov.ar:11336/22136instacron: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 09:47:25.814CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Synthesis of hesperetin 7-O-glucoside from flavonoids extracted from Citrus waste using both free and immobilized α-l-rhamnosidases
title Synthesis of hesperetin 7-O-glucoside from flavonoids extracted from Citrus waste using both free and immobilized α-l-rhamnosidases
spellingShingle Synthesis of hesperetin 7-O-glucoside from flavonoids extracted from Citrus waste using both free and immobilized α-l-rhamnosidases
Celiz, Gustavo
Citrus Flavonoids
Enzymatic Hydrolisis
Rhamnosidases
Hesperetin 7-O-Glucoside
Hesperidin
Neohesperidin
title_short Synthesis of hesperetin 7-O-glucoside from flavonoids extracted from Citrus waste using both free and immobilized α-l-rhamnosidases
title_full Synthesis of hesperetin 7-O-glucoside from flavonoids extracted from Citrus waste using both free and immobilized α-l-rhamnosidases
title_fullStr Synthesis of hesperetin 7-O-glucoside from flavonoids extracted from Citrus waste using both free and immobilized α-l-rhamnosidases
title_full_unstemmed Synthesis of hesperetin 7-O-glucoside from flavonoids extracted from Citrus waste using both free and immobilized α-l-rhamnosidases
title_sort Synthesis of hesperetin 7-O-glucoside from flavonoids extracted from Citrus waste using both free and immobilized α-l-rhamnosidases
dc.creator.none.fl_str_mv Celiz, Gustavo
Rodriguez Zotelo, Juan Jesus
Soria, Francisco Fernando
Daz, Mirta Elizabeth
author Celiz, Gustavo
author_facet Celiz, Gustavo
Rodriguez Zotelo, Juan Jesus
Soria, Francisco Fernando
Daz, Mirta Elizabeth
author_role author
author2 Rodriguez Zotelo, Juan Jesus
Soria, Francisco Fernando
Daz, Mirta Elizabeth
author2_role author
author
author
dc.subject.none.fl_str_mv Citrus Flavonoids
Enzymatic Hydrolisis
Rhamnosidases
Hesperetin 7-O-Glucoside
Hesperidin
Neohesperidin
topic Citrus Flavonoids
Enzymatic Hydrolisis
Rhamnosidases
Hesperetin 7-O-Glucoside
Hesperidin
Neohesperidin
purl_subject.fl_str_mv https://purl.org/becyt/ford/2.9
https://purl.org/becyt/ford/2
dc.description.none.fl_txt_mv This work was aimed to design alternatives to semi-synthesize hesperetin 7-O-glucoside (HG), a low occurrence natural product, from the flavonoids hesperidin (HES) and neohesperidin (NEO) that can be extracted at large scale from Citrus. To fulfill this objective, the activities of three α-l-rhamnosidases were characterized using both synthetic and natural substrates. Our results indicate that NEO is a good substrate for HG synthesis, mainly because of its solubility in water. Regarding the biocatalysts assessed, all the rhamnosidases exhibited good performances for NEO hydrolysis. Particularly, rhamnosidase from Aspergillus terreus was covalently immobilized onto azide-Dacron magnetized support, activating the support with NaNO2. Immobilized rhamnosidase presented high stability against both thermal denaturation and washing. Based on the results obtained, two methods to obtain HG from NEO are proposed, the first one involving a soluble commercial enzyme, and the second one using the immobilized biocatalyst. Using the latter approach, HG was obtained almost pure at lab-scale, with an overall yield of 93%.
Fil: Celiz, Gustavo. 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: Rodriguez Zotelo, Juan Jesus. 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: Soria, Francisco Fernando. 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. 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 This work was aimed to design alternatives to semi-synthesize hesperetin 7-O-glucoside (HG), a low occurrence natural product, from the flavonoids hesperidin (HES) and neohesperidin (NEO) that can be extracted at large scale from Citrus. To fulfill this objective, the activities of three α-l-rhamnosidases were characterized using both synthetic and natural substrates. Our results indicate that NEO is a good substrate for HG synthesis, mainly because of its solubility in water. Regarding the biocatalysts assessed, all the rhamnosidases exhibited good performances for NEO hydrolysis. Particularly, rhamnosidase from Aspergillus terreus was covalently immobilized onto azide-Dacron magnetized support, activating the support with NaNO2. Immobilized rhamnosidase presented high stability against both thermal denaturation and washing. Based on the results obtained, two methods to obtain HG from NEO are proposed, the first one involving a soluble commercial enzyme, and the second one using the immobilized biocatalyst. Using the latter approach, HG was obtained almost pure at lab-scale, with an overall yield of 93%.
publishDate 2015
dc.date.none.fl_str_mv 2015-06
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/11336/22136
Celiz, Gustavo; Rodriguez Zotelo, Juan Jesus; Soria, Francisco Fernando; Daz, Mirta Elizabeth; Synthesis of hesperetin 7-O-glucoside from flavonoids extracted from Citrus waste using both free and immobilized α-l-rhamnosidases; Elsevier; Biocatalysis and Agricultural Biotechnology; 4; 3; 6-2015; 335-341
1878-8181
CONICET Digital
CONICET
url http://hdl.handle.net/11336/22136
identifier_str_mv Celiz, Gustavo; Rodriguez Zotelo, Juan Jesus; Soria, Francisco Fernando; Daz, Mirta Elizabeth; Synthesis of hesperetin 7-O-glucoside from flavonoids extracted from Citrus waste using both free and immobilized α-l-rhamnosidases; Elsevier; Biocatalysis and Agricultural Biotechnology; 4; 3; 6-2015; 335-341
1878-8181
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.1016/j.bcab.2015.06.005
info:eu-repo/semantics/altIdentifier/url/http://www.sciencedirect.com/science/article/pii/S1878818115000778
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by-nc-nd/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by-nc-nd/2.5/ar/
dc.format.none.fl_str_mv 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 13.070432

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