Obtaining hesperetin 7-O-glucosyl 6’’-O-laurate, a high lipophilic flavonoid ester, from Citrus waste

A biotechnological process that combines the treatment of Citrus processing waste to extract a high-valuable biomolecule, neohesperidin (NEO), and its further modification by biocatalysis to enhance the lipophilicity of its flavonoic moiety is presented. NEO was extracted from immature fruits of Cit...

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Detalles Bibliográficos
Autores: Celiz, Gustavo, Díaz, Ramón, Daz, Mirta Elizabeth
Tipo de recurso: artículo
Estado:Versión publicada
Fecha de publicación:2018
País:Argentina
Institución:Consejo Nacional de Investigaciones Científicas y Técnicas
Repositorio:CONICET Digital (CONICET)
Idioma:inglés
OAI Identifier:oai:ri.conicet.gov.ar:11336/65586
Acceso en línea:http://hdl.handle.net/11336/65586
Access Level:acceso abierto
Palabra clave:Citrus Processing Waste
Enzymatic Esterification
Flavonoid Ester
Hesperetin 7-O-Glucoside
Neohesperidin
https://purl.org/becyt/ford/2.9
https://purl.org/becyt/ford/2
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repository_id_str
spelling Obtaining hesperetin 7-O-glucosyl 6’’-O-laurate, a high lipophilic flavonoid ester, from Citrus wasteCeliz, GustavoDíaz, RamónDaz, Mirta ElizabethCitrus Processing WasteEnzymatic EsterificationFlavonoid EsterHesperetin 7-O-GlucosideNeohesperidinhttps://purl.org/becyt/ford/2.9https://purl.org/becyt/ford/2A biotechnological process that combines the treatment of Citrus processing waste to extract a high-valuable biomolecule, neohesperidin (NEO), and its further modification by biocatalysis to enhance the lipophilicity of its flavonoic moiety is presented. NEO was extracted from immature fruits of Citrus aurantium and hydrolyzed by a commercial alpha-rhamnosidase to obtain hesperetin 7-glucoside (HG). NEO and HG were mono-acylated with vinyl laurate by using Novozym 435 in their primary OH-groups, but the esterification reaction was substantially faster for HG than NEO. Furthermore, the activation energy of the reaction lowers as solvents’ log-P decreases linearly. Under best conditions, HGL was obtained at gram scale with a simple downstream process. The solubility in n-octanol increased with each biocatalytic step (NEOFil: 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: Díaz, Ramón. Universidad Nacional de Salta. Facultad de Ciencias Exactas. Departamento de 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; ArgentinaElsevier2018-01info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/65586Celiz, Gustavo; Díaz, Ramón; Daz, Mirta Elizabeth; Obtaining hesperetin 7-O-glucosyl 6’’-O-laurate, a high lipophilic flavonoid ester, from Citrus waste; Elsevier; Biocatalysis and Agricultural Biotechnology; 13; 1-2018; 25-301878-8181CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/pii/S1878818117302852info:eu-repo/semantics/altIdentifier/doi/10.1016/j.bcab.2017.10.015info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-nd/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2024-05-08T13:49:21Zoai:ri.conicet.gov.ar:11336/65586instacron: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:34982024-05-08 13:49:21.623CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Obtaining hesperetin 7-O-glucosyl 6’’-O-laurate, a high lipophilic flavonoid ester, from Citrus waste
title Obtaining hesperetin 7-O-glucosyl 6’’-O-laurate, a high lipophilic flavonoid ester, from Citrus waste
spellingShingle Obtaining hesperetin 7-O-glucosyl 6’’-O-laurate, a high lipophilic flavonoid ester, from Citrus waste
Celiz, Gustavo
Citrus Processing Waste
Enzymatic Esterification
Flavonoid Ester
Hesperetin 7-O-Glucoside
Neohesperidin
https://purl.org/becyt/ford/2.9
https://purl.org/becyt/ford/2
title_short Obtaining hesperetin 7-O-glucosyl 6’’-O-laurate, a high lipophilic flavonoid ester, from Citrus waste
title_full Obtaining hesperetin 7-O-glucosyl 6’’-O-laurate, a high lipophilic flavonoid ester, from Citrus waste
title_fullStr Obtaining hesperetin 7-O-glucosyl 6’’-O-laurate, a high lipophilic flavonoid ester, from Citrus waste
title_full_unstemmed Obtaining hesperetin 7-O-glucosyl 6’’-O-laurate, a high lipophilic flavonoid ester, from Citrus waste
title_sort Obtaining hesperetin 7-O-glucosyl 6’’-O-laurate, a high lipophilic flavonoid ester, from Citrus waste
dc.creator.none.fl_str_mv Celiz, Gustavo
Díaz, Ramón
Daz, Mirta Elizabeth
author Celiz, Gustavo
author_facet Celiz, Gustavo
Díaz, Ramón
Daz, Mirta Elizabeth
author_role author
author2 Díaz, Ramón
Daz, Mirta Elizabeth
author2_role author
author
dc.subject.none.fl_str_mv Citrus Processing Waste
Enzymatic Esterification
Flavonoid Ester
Hesperetin 7-O-Glucoside
Neohesperidin
https://purl.org/becyt/ford/2.9
https://purl.org/becyt/ford/2
topic Citrus Processing Waste
Enzymatic Esterification
Flavonoid Ester
Hesperetin 7-O-Glucoside
Neohesperidin
https://purl.org/becyt/ford/2.9
https://purl.org/becyt/ford/2
description A biotechnological process that combines the treatment of Citrus processing waste to extract a high-valuable biomolecule, neohesperidin (NEO), and its further modification by biocatalysis to enhance the lipophilicity of its flavonoic moiety is presented. NEO was extracted from immature fruits of Citrus aurantium and hydrolyzed by a commercial alpha-rhamnosidase to obtain hesperetin 7-glucoside (HG). NEO and HG were mono-acylated with vinyl laurate by using Novozym 435 in their primary OH-groups, but the esterification reaction was substantially faster for HG than NEO. Furthermore, the activation energy of the reaction lowers as solvents’ log-P decreases linearly. Under best conditions, HGL was obtained at gram scale with a simple downstream process. The solubility in n-octanol increased with each biocatalytic step (NEO
publishDate 2018
dc.date.none.fl_str_mv 2018-01
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/11336/65586
Celiz, Gustavo; Díaz, Ramón; Daz, Mirta Elizabeth; Obtaining hesperetin 7-O-glucosyl 6’’-O-laurate, a high lipophilic flavonoid ester, from Citrus waste; Elsevier; Biocatalysis and Agricultural Biotechnology; 13; 1-2018; 25-30
1878-8181
CONICET Digital
CONICET
url http://hdl.handle.net/11336/65586
identifier_str_mv Celiz, Gustavo; Díaz, Ramón; Daz, Mirta Elizabeth; Obtaining hesperetin 7-O-glucosyl 6’’-O-laurate, a high lipophilic flavonoid ester, from Citrus waste; Elsevier; Biocatalysis and Agricultural Biotechnology; 13; 1-2018; 25-30
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/url/https://www.sciencedirect.com/science/article/pii/S1878818117302852
info:eu-repo/semantics/altIdentifier/doi/10.1016/j.bcab.2017.10.015
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
instname_str Consejo Nacional de Investigaciones Científicas y Técnicas
reponame_str CONICET Digital (CONICET)
collection CONICET Digital (CONICET)
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 15.811543

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