Enzyme-mediated transglycosylation of rutinose (6-O-α-L-rhamnosyl-D-glucose) to phenolic compounds by a diglycosidase from Acremonium sp. DSM 24697
- Autores
- Mazzaferro, Laura; Weiz, Gisela; Braun, Lucas Ezequiel; Kotik, Michael; Pelantová, Helena; Kren, Vladimír; Breccia, Javier Dario
- Año de publicación
- 2019
- Idioma
- inglés
- Tipo de recurso
- artículo
- Estado
- versión publicada
- Descripción
- The structure of the carbohydrate moiety of a natural phenolic glycoside can have a significant effect on the molecular interactions and physicochemical and pharmacokinetic properties of the entire compound, which may include anti-inflammatory and anticancer activities. The enzyme 6-O-α-rhamnosyl-β-glucosidase (EC 3.2.1.168) has the capacity to transfer the rutinosyl moiety (6-O-α-L-rhamnopyranosylβ-D-glucopyranose) from 7-O-rutinosylated flavonoids to hydroxylated organic compounds. This transglycosylation reaction was optimized using hydroquinone (HQ) and hesperidin as rutinose acceptor and donor, respectively. Since HQ undergoes oxidation in a neutral to alkaline aqueous environment, the transglycosylation process was carried out at pH values 6.0. The structure of 4-hydroxyphenyl-β-rutinoside was confirmed by NMR, that is, a single glycosylated product with a free hydroxyl group was formed. The highest yield of 4-hydroxyphenyl-β-rutinoside (38%, regarding hesperidin) was achieved in a 2-h process at pH 5.0 and 30 ◦C, with 36 mM OH-acceptor and 5% (v/v) cosolvent. Under the same conditions, the enzyme synthesized glycoconjugates of various phenolic compounds (phloroglucinol, resorcinol, pyrogallol, catechol), with yields between 12% and 28% and an apparent direct linear relationship between the yield and the pKa value of the aglycon. This work is a contribution to the development of convenient and sustainable processes for the glycosylation of small phenolic compounds.
Fil: Mazzaferro, Laura. Universidad Nacional de La Pampa; Argentina. Consejo Nacional de Investigaciones Cientificas y Tecnicas. Centro Cientifico Tecnologico Conicet - Patagonia Confluencia. Instituto de Ciencias de la Tierra y Ambientales de la Pampa. Grupo Vinculado Fundacion Centro de Salud E Investigaciones Medicas | Universidad Nacional de la Pampa. Facultad de Ciencias Exactas y Naturales. Instituto de Ciencias de la Tierra y Ambientales de la Pampa. Grupo Vinculado Fundacion Centro de Salud E Investigaciones Medicas.; Argentina
Fil: Weiz, Gisela. Universidad Nacional de La Pampa; Argentina. Consejo Nacional de Investigaciones Cientificas y Tecnicas. Centro Cientifico Tecnologico Conicet - Patagonia Confluencia. Instituto de Ciencias de la Tierra y Ambientales de la Pampa. Grupo Vinculado Fundacion Centro de Salud E Investigaciones Medicas | Universidad Nacional de la Pampa. Facultad de Ciencias Exactas y Naturales. Instituto de Ciencias de la Tierra y Ambientales de la Pampa. Grupo Vinculado Fundacion Centro de Salud E Investigaciones Medicas.; Argentina
Fil: Braun, Lucas Ezequiel. Universidad Nacional de La Pampa; Argentina. Consejo Nacional de Investigaciones Cientificas y Tecnicas. Centro Cientifico Tecnologico Conicet - Patagonia Confluencia. Instituto de Ciencias de la Tierra y Ambientales de la Pampa. Grupo Vinculado Fundacion Centro de Salud E Investigaciones Medicas | Universidad Nacional de la Pampa. Facultad de Ciencias Exactas y Naturales. Instituto de Ciencias de la Tierra y Ambientales de la Pampa. Grupo Vinculado Fundacion Centro de Salud E Investigaciones Medicas.; Argentina
Fil: Kotik, Michael. Czech Academy of Sciences. Institute of Organic Chemistry and Biochemistry; República Checa
Fil: Pelantová, Helena. Czech Academy of Sciences. Institute of Organic Chemistry and Biochemistry; República Checa
Fil: Kren, Vladimír. Czech Academy of Sciences. Institute of Organic Chemistry and Biochemistry; República Checa
Fil: Breccia, Javier Dario. Universidad Nacional de La Pampa; Argentina. Consejo Nacional de Investigaciones Cientificas y Tecnicas. Centro Cientifico Tecnologico Conicet - Patagonia Confluencia. Instituto de Ciencias de la Tierra y Ambientales de la Pampa. Grupo Vinculado Fundacion Centro de Salud E Investigaciones Medicas | Universidad Nacional de la Pampa. Facultad de Ciencias Exactas y Naturales. Instituto de Ciencias de la Tierra y Ambientales de la Pampa. Grupo Vinculado Fundacion Centro de Salud E Investigaciones Medicas.; Argentina - Materia
-
HESPERIDIN
HYDROQUINONE
Α-RHAMNOSYL-Β-GLUCOSIDASE - Nivel de accesibilidad
- acceso abierto
- Condiciones de uso
- https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
- Repositorio
- Institución
- Consejo Nacional de Investigaciones Científicas y Técnicas
- OAI Identificador
- oai:ri.conicet.gov.ar:11336/112405
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Enzyme-mediated transglycosylation of rutinose (6-O-α-L-rhamnosyl-D-glucose) to phenolic compounds by a diglycosidase from Acremonium sp. DSM 24697Mazzaferro, LauraWeiz, GiselaBraun, Lucas EzequielKotik, MichaelPelantová, HelenaKren, VladimírBreccia, Javier DarioHESPERIDINHYDROQUINONEΑ-RHAMNOSYL-Β-GLUCOSIDASEhttps://purl.org/becyt/ford/2.9https://purl.org/becyt/ford/2The structure of the carbohydrate moiety of a natural phenolic glycoside can have a significant effect on the molecular interactions and physicochemical and pharmacokinetic properties of the entire compound, which may include anti-inflammatory and anticancer activities. The enzyme 6-O-α-rhamnosyl-β-glucosidase (EC 3.2.1.168) has the capacity to transfer the rutinosyl moiety (6-O-α-L-rhamnopyranosylβ-D-glucopyranose) from 7-O-rutinosylated flavonoids to hydroxylated organic compounds. This transglycosylation reaction was optimized using hydroquinone (HQ) and hesperidin as rutinose acceptor and donor, respectively. Since HQ undergoes oxidation in a neutral to alkaline aqueous environment, the transglycosylation process was carried out at pH values 6.0. The structure of 4-hydroxyphenyl-β-rutinoside was confirmed by NMR, that is, a single glycosylated product with a free hydroxyl group was formed. The highest yield of 4-hydroxyphenyl-β-rutinoside (38%, regarding hesperidin) was achieved in a 2-h process at pH 5.0 and 30 ◦C, with 36 mM OH-acceptor and 5% (v/v) cosolvent. Under the same conditions, the enzyme synthesized glycoconjugates of various phenolic compounds (phloroglucinol, resorcinol, pyrogallol, catechol), with yields between 12% and 28% and an apparent direct linear relationship between the yield and the pKa value of the aglycon. This work is a contribution to the development of convenient and sustainable processes for the glycosylation of small phenolic compounds.Fil: Mazzaferro, Laura. Universidad Nacional de La Pampa; Argentina. Consejo Nacional de Investigaciones Cientificas y Tecnicas. Centro Cientifico Tecnologico Conicet - Patagonia Confluencia. Instituto de Ciencias de la Tierra y Ambientales de la Pampa. Grupo Vinculado Fundacion Centro de Salud E Investigaciones Medicas | Universidad Nacional de la Pampa. Facultad de Ciencias Exactas y Naturales. Instituto de Ciencias de la Tierra y Ambientales de la Pampa. Grupo Vinculado Fundacion Centro de Salud E Investigaciones Medicas.; ArgentinaFil: Weiz, Gisela. Universidad Nacional de La Pampa; Argentina. Consejo Nacional de Investigaciones Cientificas y Tecnicas. Centro Cientifico Tecnologico Conicet - Patagonia Confluencia. Instituto de Ciencias de la Tierra y Ambientales de la Pampa. Grupo Vinculado Fundacion Centro de Salud E Investigaciones Medicas | Universidad Nacional de la Pampa. Facultad de Ciencias Exactas y Naturales. Instituto de Ciencias de la Tierra y Ambientales de la Pampa. Grupo Vinculado Fundacion Centro de Salud E Investigaciones Medicas.; ArgentinaFil: Braun, Lucas Ezequiel. Universidad Nacional de La Pampa; Argentina. Consejo Nacional de Investigaciones Cientificas y Tecnicas. Centro Cientifico Tecnologico Conicet - Patagonia Confluencia. Instituto de Ciencias de la Tierra y Ambientales de la Pampa. Grupo Vinculado Fundacion Centro de Salud E Investigaciones Medicas | Universidad Nacional de la Pampa. Facultad de Ciencias Exactas y Naturales. Instituto de Ciencias de la Tierra y Ambientales de la Pampa. Grupo Vinculado Fundacion Centro de Salud E Investigaciones Medicas.; ArgentinaFil: Kotik, Michael. Czech Academy of Sciences. Institute of Organic Chemistry and Biochemistry; República ChecaFil: Pelantová, Helena. Czech Academy of Sciences. Institute of Organic Chemistry and Biochemistry; República ChecaFil: Kren, Vladimír. Czech Academy of Sciences. Institute of Organic Chemistry and Biochemistry; República ChecaFil: Breccia, Javier Dario. Universidad Nacional de La Pampa; Argentina. Consejo Nacional de Investigaciones Cientificas y Tecnicas. Centro Cientifico Tecnologico Conicet - Patagonia Confluencia. Instituto de Ciencias de la Tierra y Ambientales de la Pampa. Grupo Vinculado Fundacion Centro de Salud E Investigaciones Medicas | Universidad Nacional de la Pampa. Facultad de Ciencias Exactas y Naturales. Instituto de Ciencias de la Tierra y Ambientales de la Pampa. Grupo Vinculado Fundacion Centro de Salud E Investigaciones Medicas.; ArgentinaPortland Press2019-01info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/112405Mazzaferro, Laura; Weiz, Gisela; Braun, Lucas Ezequiel; Kotik, Michael; Pelantová, Helena; et al.; Enzyme-mediated transglycosylation of rutinose (6-O-α-L-rhamnosyl-D-glucose) to phenolic compounds by a diglycosidase from Acremonium sp. DSM 24697; Portland Press; Biotechnology and Applied Biochemistry; 66; 1; 1-2019; 53-590885-4513CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/info:eu-repo/semantics/altIdentifier/doi/10.1002/bab.1695info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-03T09:44:07Zoai:ri.conicet.gov.ar:11336/112405instacron: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:34982025-09-03 09:44:07.321CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse |
dc.title.none.fl_str_mv |
Enzyme-mediated transglycosylation of rutinose (6-O-α-L-rhamnosyl-D-glucose) to phenolic compounds by a diglycosidase from Acremonium sp. DSM 24697 |
title |
Enzyme-mediated transglycosylation of rutinose (6-O-α-L-rhamnosyl-D-glucose) to phenolic compounds by a diglycosidase from Acremonium sp. DSM 24697 |
spellingShingle |
Enzyme-mediated transglycosylation of rutinose (6-O-α-L-rhamnosyl-D-glucose) to phenolic compounds by a diglycosidase from Acremonium sp. DSM 24697 Mazzaferro, Laura HESPERIDIN HYDROQUINONE Α-RHAMNOSYL-Β-GLUCOSIDASE |
title_short |
Enzyme-mediated transglycosylation of rutinose (6-O-α-L-rhamnosyl-D-glucose) to phenolic compounds by a diglycosidase from Acremonium sp. DSM 24697 |
title_full |
Enzyme-mediated transglycosylation of rutinose (6-O-α-L-rhamnosyl-D-glucose) to phenolic compounds by a diglycosidase from Acremonium sp. DSM 24697 |
title_fullStr |
Enzyme-mediated transglycosylation of rutinose (6-O-α-L-rhamnosyl-D-glucose) to phenolic compounds by a diglycosidase from Acremonium sp. DSM 24697 |
title_full_unstemmed |
Enzyme-mediated transglycosylation of rutinose (6-O-α-L-rhamnosyl-D-glucose) to phenolic compounds by a diglycosidase from Acremonium sp. DSM 24697 |
title_sort |
Enzyme-mediated transglycosylation of rutinose (6-O-α-L-rhamnosyl-D-glucose) to phenolic compounds by a diglycosidase from Acremonium sp. DSM 24697 |
dc.creator.none.fl_str_mv |
Mazzaferro, Laura Weiz, Gisela Braun, Lucas Ezequiel Kotik, Michael Pelantová, Helena Kren, Vladimír Breccia, Javier Dario |
author |
Mazzaferro, Laura |
author_facet |
Mazzaferro, Laura Weiz, Gisela Braun, Lucas Ezequiel Kotik, Michael Pelantová, Helena Kren, Vladimír Breccia, Javier Dario |
author_role |
author |
author2 |
Weiz, Gisela Braun, Lucas Ezequiel Kotik, Michael Pelantová, Helena Kren, Vladimír Breccia, Javier Dario |
author2_role |
author author author author author author |
dc.subject.none.fl_str_mv |
HESPERIDIN HYDROQUINONE Α-RHAMNOSYL-Β-GLUCOSIDASE |
topic |
HESPERIDIN HYDROQUINONE Α-RHAMNOSYL-Β-GLUCOSIDASE |
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 structure of the carbohydrate moiety of a natural phenolic glycoside can have a significant effect on the molecular interactions and physicochemical and pharmacokinetic properties of the entire compound, which may include anti-inflammatory and anticancer activities. The enzyme 6-O-α-rhamnosyl-β-glucosidase (EC 3.2.1.168) has the capacity to transfer the rutinosyl moiety (6-O-α-L-rhamnopyranosylβ-D-glucopyranose) from 7-O-rutinosylated flavonoids to hydroxylated organic compounds. This transglycosylation reaction was optimized using hydroquinone (HQ) and hesperidin as rutinose acceptor and donor, respectively. Since HQ undergoes oxidation in a neutral to alkaline aqueous environment, the transglycosylation process was carried out at pH values 6.0. The structure of 4-hydroxyphenyl-β-rutinoside was confirmed by NMR, that is, a single glycosylated product with a free hydroxyl group was formed. The highest yield of 4-hydroxyphenyl-β-rutinoside (38%, regarding hesperidin) was achieved in a 2-h process at pH 5.0 and 30 ◦C, with 36 mM OH-acceptor and 5% (v/v) cosolvent. Under the same conditions, the enzyme synthesized glycoconjugates of various phenolic compounds (phloroglucinol, resorcinol, pyrogallol, catechol), with yields between 12% and 28% and an apparent direct linear relationship between the yield and the pKa value of the aglycon. This work is a contribution to the development of convenient and sustainable processes for the glycosylation of small phenolic compounds. Fil: Mazzaferro, Laura. Universidad Nacional de La Pampa; Argentina. Consejo Nacional de Investigaciones Cientificas y Tecnicas. Centro Cientifico Tecnologico Conicet - Patagonia Confluencia. Instituto de Ciencias de la Tierra y Ambientales de la Pampa. Grupo Vinculado Fundacion Centro de Salud E Investigaciones Medicas | Universidad Nacional de la Pampa. Facultad de Ciencias Exactas y Naturales. Instituto de Ciencias de la Tierra y Ambientales de la Pampa. Grupo Vinculado Fundacion Centro de Salud E Investigaciones Medicas.; Argentina Fil: Weiz, Gisela. Universidad Nacional de La Pampa; Argentina. Consejo Nacional de Investigaciones Cientificas y Tecnicas. Centro Cientifico Tecnologico Conicet - Patagonia Confluencia. Instituto de Ciencias de la Tierra y Ambientales de la Pampa. Grupo Vinculado Fundacion Centro de Salud E Investigaciones Medicas | Universidad Nacional de la Pampa. Facultad de Ciencias Exactas y Naturales. Instituto de Ciencias de la Tierra y Ambientales de la Pampa. Grupo Vinculado Fundacion Centro de Salud E Investigaciones Medicas.; Argentina Fil: Braun, Lucas Ezequiel. Universidad Nacional de La Pampa; Argentina. Consejo Nacional de Investigaciones Cientificas y Tecnicas. Centro Cientifico Tecnologico Conicet - Patagonia Confluencia. Instituto de Ciencias de la Tierra y Ambientales de la Pampa. Grupo Vinculado Fundacion Centro de Salud E Investigaciones Medicas | Universidad Nacional de la Pampa. Facultad de Ciencias Exactas y Naturales. Instituto de Ciencias de la Tierra y Ambientales de la Pampa. Grupo Vinculado Fundacion Centro de Salud E Investigaciones Medicas.; Argentina Fil: Kotik, Michael. Czech Academy of Sciences. Institute of Organic Chemistry and Biochemistry; República Checa Fil: Pelantová, Helena. Czech Academy of Sciences. Institute of Organic Chemistry and Biochemistry; República Checa Fil: Kren, Vladimír. Czech Academy of Sciences. Institute of Organic Chemistry and Biochemistry; República Checa Fil: Breccia, Javier Dario. Universidad Nacional de La Pampa; Argentina. Consejo Nacional de Investigaciones Cientificas y Tecnicas. Centro Cientifico Tecnologico Conicet - Patagonia Confluencia. Instituto de Ciencias de la Tierra y Ambientales de la Pampa. Grupo Vinculado Fundacion Centro de Salud E Investigaciones Medicas | Universidad Nacional de la Pampa. Facultad de Ciencias Exactas y Naturales. Instituto de Ciencias de la Tierra y Ambientales de la Pampa. Grupo Vinculado Fundacion Centro de Salud E Investigaciones Medicas.; Argentina |
description |
The structure of the carbohydrate moiety of a natural phenolic glycoside can have a significant effect on the molecular interactions and physicochemical and pharmacokinetic properties of the entire compound, which may include anti-inflammatory and anticancer activities. The enzyme 6-O-α-rhamnosyl-β-glucosidase (EC 3.2.1.168) has the capacity to transfer the rutinosyl moiety (6-O-α-L-rhamnopyranosylβ-D-glucopyranose) from 7-O-rutinosylated flavonoids to hydroxylated organic compounds. This transglycosylation reaction was optimized using hydroquinone (HQ) and hesperidin as rutinose acceptor and donor, respectively. Since HQ undergoes oxidation in a neutral to alkaline aqueous environment, the transglycosylation process was carried out at pH values 6.0. The structure of 4-hydroxyphenyl-β-rutinoside was confirmed by NMR, that is, a single glycosylated product with a free hydroxyl group was formed. The highest yield of 4-hydroxyphenyl-β-rutinoside (38%, regarding hesperidin) was achieved in a 2-h process at pH 5.0 and 30 ◦C, with 36 mM OH-acceptor and 5% (v/v) cosolvent. Under the same conditions, the enzyme synthesized glycoconjugates of various phenolic compounds (phloroglucinol, resorcinol, pyrogallol, catechol), with yields between 12% and 28% and an apparent direct linear relationship between the yield and the pKa value of the aglycon. This work is a contribution to the development of convenient and sustainable processes for the glycosylation of small phenolic compounds. |
publishDate |
2019 |
dc.date.none.fl_str_mv |
2019-01 |
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/11336/112405 Mazzaferro, Laura; Weiz, Gisela; Braun, Lucas Ezequiel; Kotik, Michael; Pelantová, Helena; et al.; Enzyme-mediated transglycosylation of rutinose (6-O-α-L-rhamnosyl-D-glucose) to phenolic compounds by a diglycosidase from Acremonium sp. DSM 24697; Portland Press; Biotechnology and Applied Biochemistry; 66; 1; 1-2019; 53-59 0885-4513 CONICET Digital CONICET |
url |
http://hdl.handle.net/11336/112405 |
identifier_str_mv |
Mazzaferro, Laura; Weiz, Gisela; Braun, Lucas Ezequiel; Kotik, Michael; Pelantová, Helena; et al.; Enzyme-mediated transglycosylation of rutinose (6-O-α-L-rhamnosyl-D-glucose) to phenolic compounds by a diglycosidase from Acremonium sp. DSM 24697; Portland Press; Biotechnology and Applied Biochemistry; 66; 1; 1-2019; 53-59 0885-4513 CONICET Digital CONICET |
dc.language.none.fl_str_mv |
eng |
language |
eng |
dc.relation.none.fl_str_mv |
info:eu-repo/semantics/altIdentifier/doi/ info:eu-repo/semantics/altIdentifier/doi/10.1002/bab.1695 |
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 application/pdf |
dc.publisher.none.fl_str_mv |
Portland Press |
publisher.none.fl_str_mv |
Portland Press |
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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1842268646337937408 |
score |
13.13397 |