Microbial functionalization of (–)-ambroxide by filamentous fungi

Autores
Allendes, Jorge Ariel; Bustos, Daniela Alicia; Pacciaroni, Adriana del Valle; Sosa, Virginia Estela; Bustos, Daniel Alfredo
Año de publicación
2011
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
Biocatalysis is a very useful tool for organic chemists to functionalize organic compounds under working conditions milder than chemical ones. This methodology has special significance since it can be an easy way to introduce a functional group in a non-reactive carbon, regio- and stereoselectively. In order to look for new compounds with antioxidant activity we report the transformation of the natural substrate (–)-ambroxide using the enzyme potential of pure strains of the filamentous fungi Alternaria alternata and Cunninghamella sp., following a protocol with growing cell cultures, which produced the new compound 1β-hydroxyambroxide and the previously known compound 3β-hydroxyambroxide. After purification their structures were elucidated by spectroscopic methods. These two metabolites are the products of oxidation of ring A of the starting material, without evidence of other compounds with different functionalization. Both compounds were tested for their activity as free radical scavengers in vitro, using the assay of DPPH (1,1-diphenyl-2-picrylhydrazyl) radical trapping. The results demonstrated that hydroxylation of carbons C-1 and C-3 of (–)-ambroxide with β stereochemistry had no effect on biological activity as an antioxidant compared with the starting material and a reference substance.
Fil: Allendes, Jorge Ariel. Universidad Nacional de San Juan; Argentina
Fil: Bustos, Daniela Alicia. Universidad Nacional de San Juan; Argentina
Fil: Pacciaroni, Adriana del Valle. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto Multidisciplinario de Biología Vegetal. Universidad Nacional de Córdoba. Facultad de Ciencias Exactas Físicas y Naturales. Instituto Multidisciplinario de Biología Vegetal; Argentina
Fil: Sosa, Virginia Estela. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto Multidisciplinario de Biología Vegetal. Universidad Nacional de Córdoba. Facultad de Ciencias Exactas Físicas y Naturales. Instituto Multidisciplinario de Biología Vegetal; Argentina
Fil: Bustos, Daniel Alfredo. Universidad Nacional de San Juan; Argentina
Materia
1Β -HYDROXYAMBROXIDE
3Β -HYDROXYAMBROXIDE
ALTERNARIA ALTERNATE
BIOTRANSFORMATION
CUNNINGHAMELLA SP.
RADICAL SCAVENGER ACTIVITY
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:11336/15170
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/15170
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Microbial functionalization of (–)-ambroxide by filamentous fungiAllendes, Jorge ArielBustos, Daniela AliciaPacciaroni, Adriana del ValleSosa, Virginia EstelaBustos, Daniel Alfredo1Β -HYDROXYAMBROXIDE3Β -HYDROXYAMBROXIDEALTERNARIA ALTERNATEBIOTRANSFORMATIONCUNNINGHAMELLA SP.RADICAL SCAVENGER ACTIVITYhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1Biocatalysis is a very useful tool for organic chemists to functionalize organic compounds under working conditions milder than chemical ones. This methodology has special significance since it can be an easy way to introduce a functional group in a non-reactive carbon, regio- and stereoselectively. In order to look for new compounds with antioxidant activity we report the transformation of the natural substrate (–)-ambroxide using the enzyme potential of pure strains of the filamentous fungi Alternaria alternata and Cunninghamella sp., following a protocol with growing cell cultures, which produced the new compound 1β-hydroxyambroxide and the previously known compound 3β-hydroxyambroxide. After purification their structures were elucidated by spectroscopic methods. These two metabolites are the products of oxidation of ring A of the starting material, without evidence of other compounds with different functionalization. Both compounds were tested for their activity as free radical scavengers in vitro, using the assay of DPPH (1,1-diphenyl-2-picrylhydrazyl) radical trapping. The results demonstrated that hydroxylation of carbons C-1 and C-3 of (–)-ambroxide with β stereochemistry had no effect on biological activity as an antioxidant compared with the starting material and a reference substance.Fil: Allendes, Jorge Ariel. Universidad Nacional de San Juan; ArgentinaFil: Bustos, Daniela Alicia. Universidad Nacional de San Juan; ArgentinaFil: Pacciaroni, Adriana del Valle. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto Multidisciplinario de Biología Vegetal. Universidad Nacional de Córdoba. Facultad de Ciencias Exactas Físicas y Naturales. Instituto Multidisciplinario de Biología Vegetal; ArgentinaFil: Sosa, Virginia Estela. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto Multidisciplinario de Biología Vegetal. Universidad Nacional de Córdoba. Facultad de Ciencias Exactas Físicas y Naturales. Instituto Multidisciplinario de Biología Vegetal; ArgentinaFil: Bustos, Daniel Alfredo. Universidad Nacional de San Juan; ArgentinaTaylor & Francis Ltd2011-03info: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/11336/15170Allendes, Jorge Ariel; Bustos, Daniela Alicia; Pacciaroni, Adriana del Valle; Sosa, Virginia Estela; Bustos, Daniel Alfredo; Microbial functionalization of (–)-ambroxide by filamentous fungi; Taylor & Francis Ltd; Biocatalysis and Biotransformation; 29; 2-3; 3-2011; 83-861024-24221029-2446enginfo:eu-repo/semantics/altIdentifier/url/http://www.tandfonline.com/doi/abs/10.3109/10242422.2011.578211info:eu-repo/semantics/altIdentifier/doi/ 10.3109/10242422.2011.578211info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-10-22T11:30:50Zoai:ri.conicet.gov.ar:11336/15170instacron: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:34982025-10-22 11:30:50.822CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Microbial functionalization of (–)-ambroxide by filamentous fungi
title Microbial functionalization of (–)-ambroxide by filamentous fungi
spellingShingle Microbial functionalization of (–)-ambroxide by filamentous fungi
Allendes, Jorge Ariel
1Β -HYDROXYAMBROXIDE
3Β -HYDROXYAMBROXIDE
ALTERNARIA ALTERNATE
BIOTRANSFORMATION
CUNNINGHAMELLA SP.
RADICAL SCAVENGER ACTIVITY
title_short Microbial functionalization of (–)-ambroxide by filamentous fungi
title_full Microbial functionalization of (–)-ambroxide by filamentous fungi
title_fullStr Microbial functionalization of (–)-ambroxide by filamentous fungi
title_full_unstemmed Microbial functionalization of (–)-ambroxide by filamentous fungi
title_sort Microbial functionalization of (–)-ambroxide by filamentous fungi
dc.creator.none.fl_str_mv Allendes, Jorge Ariel
Bustos, Daniela Alicia
Pacciaroni, Adriana del Valle
Sosa, Virginia Estela
Bustos, Daniel Alfredo
author Allendes, Jorge Ariel
author_facet Allendes, Jorge Ariel
Bustos, Daniela Alicia
Pacciaroni, Adriana del Valle
Sosa, Virginia Estela
Bustos, Daniel Alfredo
author_role author
author2 Bustos, Daniela Alicia
Pacciaroni, Adriana del Valle
Sosa, Virginia Estela
Bustos, Daniel Alfredo
author2_role author
author
author
author
dc.subject.none.fl_str_mv 1Β -HYDROXYAMBROXIDE
3Β -HYDROXYAMBROXIDE
ALTERNARIA ALTERNATE
BIOTRANSFORMATION
CUNNINGHAMELLA SP.
RADICAL SCAVENGER ACTIVITY
topic 1Β -HYDROXYAMBROXIDE
3Β -HYDROXYAMBROXIDE
ALTERNARIA ALTERNATE
BIOTRANSFORMATION
CUNNINGHAMELLA SP.
RADICAL SCAVENGER ACTIVITY
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv Biocatalysis is a very useful tool for organic chemists to functionalize organic compounds under working conditions milder than chemical ones. This methodology has special significance since it can be an easy way to introduce a functional group in a non-reactive carbon, regio- and stereoselectively. In order to look for new compounds with antioxidant activity we report the transformation of the natural substrate (–)-ambroxide using the enzyme potential of pure strains of the filamentous fungi Alternaria alternata and Cunninghamella sp., following a protocol with growing cell cultures, which produced the new compound 1β-hydroxyambroxide and the previously known compound 3β-hydroxyambroxide. After purification their structures were elucidated by spectroscopic methods. These two metabolites are the products of oxidation of ring A of the starting material, without evidence of other compounds with different functionalization. Both compounds were tested for their activity as free radical scavengers in vitro, using the assay of DPPH (1,1-diphenyl-2-picrylhydrazyl) radical trapping. The results demonstrated that hydroxylation of carbons C-1 and C-3 of (–)-ambroxide with β stereochemistry had no effect on biological activity as an antioxidant compared with the starting material and a reference substance.
Fil: Allendes, Jorge Ariel. Universidad Nacional de San Juan; Argentina
Fil: Bustos, Daniela Alicia. Universidad Nacional de San Juan; Argentina
Fil: Pacciaroni, Adriana del Valle. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto Multidisciplinario de Biología Vegetal. Universidad Nacional de Córdoba. Facultad de Ciencias Exactas Físicas y Naturales. Instituto Multidisciplinario de Biología Vegetal; Argentina
Fil: Sosa, Virginia Estela. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Córdoba. Instituto Multidisciplinario de Biología Vegetal. Universidad Nacional de Córdoba. Facultad de Ciencias Exactas Físicas y Naturales. Instituto Multidisciplinario de Biología Vegetal; Argentina
Fil: Bustos, Daniel Alfredo. Universidad Nacional de San Juan; Argentina
description Biocatalysis is a very useful tool for organic chemists to functionalize organic compounds under working conditions milder than chemical ones. This methodology has special significance since it can be an easy way to introduce a functional group in a non-reactive carbon, regio- and stereoselectively. In order to look for new compounds with antioxidant activity we report the transformation of the natural substrate (–)-ambroxide using the enzyme potential of pure strains of the filamentous fungi Alternaria alternata and Cunninghamella sp., following a protocol with growing cell cultures, which produced the new compound 1β-hydroxyambroxide and the previously known compound 3β-hydroxyambroxide. After purification their structures were elucidated by spectroscopic methods. These two metabolites are the products of oxidation of ring A of the starting material, without evidence of other compounds with different functionalization. Both compounds were tested for their activity as free radical scavengers in vitro, using the assay of DPPH (1,1-diphenyl-2-picrylhydrazyl) radical trapping. The results demonstrated that hydroxylation of carbons C-1 and C-3 of (–)-ambroxide with β stereochemistry had no effect on biological activity as an antioxidant compared with the starting material and a reference substance.
publishDate 2011
dc.date.none.fl_str_mv 2011-03
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/11336/15170
Allendes, Jorge Ariel; Bustos, Daniela Alicia; Pacciaroni, Adriana del Valle; Sosa, Virginia Estela; Bustos, Daniel Alfredo; Microbial functionalization of (–)-ambroxide by filamentous fungi; Taylor & Francis Ltd; Biocatalysis and Biotransformation; 29; 2-3; 3-2011; 83-86
1024-2422
1029-2446
url http://hdl.handle.net/11336/15170
identifier_str_mv Allendes, Jorge Ariel; Bustos, Daniela Alicia; Pacciaroni, Adriana del Valle; Sosa, Virginia Estela; Bustos, Daniel Alfredo; Microbial functionalization of (–)-ambroxide by filamentous fungi; Taylor & Francis Ltd; Biocatalysis and Biotransformation; 29; 2-3; 3-2011; 83-86
1024-2422
1029-2446
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/url/http://www.tandfonline.com/doi/abs/10.3109/10242422.2011.578211
info:eu-repo/semantics/altIdentifier/doi/ 10.3109/10242422.2011.578211
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 Taylor & Francis Ltd
publisher.none.fl_str_mv Taylor & Francis Ltd
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 12.982451

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