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
- Institución
- Consejo Nacional de Investigaciones Científicas y Técnicas
- OAI Identificador
- oai:ri.conicet.gov.ar:11336/15170
Ver los metadatos del registro completo
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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 Técnicas2025-09-29T10:01:18Zoai: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:34982025-09-29 10:01:19.156CONICET 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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1844613805486637056 |
score |
13.070432 |