Fungal hydroxylation of (-)-α-santonin
- Autores
- Bustos, Daniela; Pacciaroni, Adriana del Valle; Bustos, Daniela A.; Sosa, Virginia Estela
- Año de publicación
- 2012
- Idioma
- inglés
- Tipo de recurso
- artículo
- Estado
- versión publicada
- Descripción
- Functionalization of organic compounds using enzymes present in microorganisms is a very useful tool for organic chemists, since it is a method carried out under milder conditions than chemical ones and allows the introduction of functional groups in a nonreactive carbon in a regioselective and stereoselective way. In order to look for new compounds derived from natural products with antioxidant and cytotoxic activity, the sesquiterpene lactone (-)-α-santonin was transformed using a pure strain of Cunninghamella spp. A two-stage standard protocol with growing cells was followed, which led to 8β-hydroxy-α-santonin. The structure of the product was unequivocally elucidated by spectroscopic methods. Both the starting material and metabolite were tested in vitro for antioxidant activity using the 1,1-diphenyl-2-picrylhydrazyl method, and cytotoxic activity was tested using the Artemia salina (brine shrimp) method. In both assays, the new compound was less active than substrate and reference compounds, which means that the introduction of a hydroxyl group on carbon-8 of (-)-α-santonin with β stereochemistry did not improve the tested biological activities
Fil: Bustos, Daniela. Universidad Nacional de San Juan. Facultad de Filosofía, Humanidades y Artes. Instituto de Cs.basicas. Area de Química; Argentina
Fil: Pacciaroni, Adriana del Valle. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Departamento de Química Orgánica; Argentina
Fil: Bustos, Daniela A.. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Departamento de Química Orgánica; 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 - Materia
-
Biotransformation
Cunninghamella spp
Antioxidant activity
Cytotoxic 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:11336/196445
Ver los metadatos del registro completo
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Fungal hydroxylation of (-)-α-santoninBustos, DanielaPacciaroni, Adriana del ValleBustos, Daniela A.Sosa, Virginia EstelaBiotransformationCunninghamella sppAntioxidant activityCytotoxic activityhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1Functionalization of organic compounds using enzymes present in microorganisms is a very useful tool for organic chemists, since it is a method carried out under milder conditions than chemical ones and allows the introduction of functional groups in a nonreactive carbon in a regioselective and stereoselective way. In order to look for new compounds derived from natural products with antioxidant and cytotoxic activity, the sesquiterpene lactone (-)-α-santonin was transformed using a pure strain of Cunninghamella spp. A two-stage standard protocol with growing cells was followed, which led to 8β-hydroxy-α-santonin. The structure of the product was unequivocally elucidated by spectroscopic methods. Both the starting material and metabolite were tested in vitro for antioxidant activity using the 1,1-diphenyl-2-picrylhydrazyl method, and cytotoxic activity was tested using the Artemia salina (brine shrimp) method. In both assays, the new compound was less active than substrate and reference compounds, which means that the introduction of a hydroxyl group on carbon-8 of (-)-α-santonin with β stereochemistry did not improve the tested biological activitiesFil: Bustos, Daniela. Universidad Nacional de San Juan. Facultad de Filosofía, Humanidades y Artes. Instituto de Cs.basicas. Area de Química; ArgentinaFil: Pacciaroni, Adriana del Valle. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Departamento de Química Orgánica; ArgentinaFil: Bustos, Daniela A.. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Departamento de Química Orgánica; 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; ArgentinaDovepress2012-08-08info: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/11336/196445Bustos, Daniela; Pacciaroni, Adriana del Valle; Bustos, Daniela A.; Sosa, Virginia Estela; Fungal hydroxylation of (-)-α-santonin; Dovepress; Reports in Organic Chemistry; 2; 8-8-2012; 1-62230-5246CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/https://www.dovepress.com/fungal-hydroxylation-of---alpha-santonin-peer-reviewed-fulltext-article-ROCinfo:eu-repo/semantics/altIdentifier/doi/10.2147/ROC.S33832info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T10:00:37Zoai:ri.conicet.gov.ar:11336/196445instacron: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 10:00:38.023CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse |
dc.title.none.fl_str_mv |
Fungal hydroxylation of (-)-α-santonin |
title |
Fungal hydroxylation of (-)-α-santonin |
spellingShingle |
Fungal hydroxylation of (-)-α-santonin Bustos, Daniela Biotransformation Cunninghamella spp Antioxidant activity Cytotoxic activity |
title_short |
Fungal hydroxylation of (-)-α-santonin |
title_full |
Fungal hydroxylation of (-)-α-santonin |
title_fullStr |
Fungal hydroxylation of (-)-α-santonin |
title_full_unstemmed |
Fungal hydroxylation of (-)-α-santonin |
title_sort |
Fungal hydroxylation of (-)-α-santonin |
dc.creator.none.fl_str_mv |
Bustos, Daniela Pacciaroni, Adriana del Valle Bustos, Daniela A. Sosa, Virginia Estela |
author |
Bustos, Daniela |
author_facet |
Bustos, Daniela Pacciaroni, Adriana del Valle Bustos, Daniela A. Sosa, Virginia Estela |
author_role |
author |
author2 |
Pacciaroni, Adriana del Valle Bustos, Daniela A. Sosa, Virginia Estela |
author2_role |
author author author |
dc.subject.none.fl_str_mv |
Biotransformation Cunninghamella spp Antioxidant activity Cytotoxic activity |
topic |
Biotransformation Cunninghamella spp Antioxidant activity Cytotoxic 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 |
Functionalization of organic compounds using enzymes present in microorganisms is a very useful tool for organic chemists, since it is a method carried out under milder conditions than chemical ones and allows the introduction of functional groups in a nonreactive carbon in a regioselective and stereoselective way. In order to look for new compounds derived from natural products with antioxidant and cytotoxic activity, the sesquiterpene lactone (-)-α-santonin was transformed using a pure strain of Cunninghamella spp. A two-stage standard protocol with growing cells was followed, which led to 8β-hydroxy-α-santonin. The structure of the product was unequivocally elucidated by spectroscopic methods. Both the starting material and metabolite were tested in vitro for antioxidant activity using the 1,1-diphenyl-2-picrylhydrazyl method, and cytotoxic activity was tested using the Artemia salina (brine shrimp) method. In both assays, the new compound was less active than substrate and reference compounds, which means that the introduction of a hydroxyl group on carbon-8 of (-)-α-santonin with β stereochemistry did not improve the tested biological activities Fil: Bustos, Daniela. Universidad Nacional de San Juan. Facultad de Filosofía, Humanidades y Artes. Instituto de Cs.basicas. Area de Química; Argentina Fil: Pacciaroni, Adriana del Valle. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Departamento de Química Orgánica; Argentina Fil: Bustos, Daniela A.. Universidad Nacional de Córdoba. Facultad de Ciencias Químicas. Departamento de Química Orgánica; 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 |
description |
Functionalization of organic compounds using enzymes present in microorganisms is a very useful tool for organic chemists, since it is a method carried out under milder conditions than chemical ones and allows the introduction of functional groups in a nonreactive carbon in a regioselective and stereoselective way. In order to look for new compounds derived from natural products with antioxidant and cytotoxic activity, the sesquiterpene lactone (-)-α-santonin was transformed using a pure strain of Cunninghamella spp. A two-stage standard protocol with growing cells was followed, which led to 8β-hydroxy-α-santonin. The structure of the product was unequivocally elucidated by spectroscopic methods. Both the starting material and metabolite were tested in vitro for antioxidant activity using the 1,1-diphenyl-2-picrylhydrazyl method, and cytotoxic activity was tested using the Artemia salina (brine shrimp) method. In both assays, the new compound was less active than substrate and reference compounds, which means that the introduction of a hydroxyl group on carbon-8 of (-)-α-santonin with β stereochemistry did not improve the tested biological activities |
publishDate |
2012 |
dc.date.none.fl_str_mv |
2012-08-08 |
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/11336/196445 Bustos, Daniela; Pacciaroni, Adriana del Valle; Bustos, Daniela A.; Sosa, Virginia Estela; Fungal hydroxylation of (-)-α-santonin; Dovepress; Reports in Organic Chemistry; 2; 8-8-2012; 1-6 2230-5246 CONICET Digital CONICET |
url |
http://hdl.handle.net/11336/196445 |
identifier_str_mv |
Bustos, Daniela; Pacciaroni, Adriana del Valle; Bustos, Daniela A.; Sosa, Virginia Estela; Fungal hydroxylation of (-)-α-santonin; Dovepress; Reports in Organic Chemistry; 2; 8-8-2012; 1-6 2230-5246 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.dovepress.com/fungal-hydroxylation-of---alpha-santonin-peer-reviewed-fulltext-article-ROC info:eu-repo/semantics/altIdentifier/doi/10.2147/ROC.S33832 |
dc.rights.none.fl_str_mv |
info:eu-repo/semantics/openAccess https://creativecommons.org/licenses/by-nc-sa/2.5/ar/ |
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openAccess |
rights_invalid_str_mv |
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/ |
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application/pdf application/pdf application/pdf application/pdf |
dc.publisher.none.fl_str_mv |
Dovepress |
publisher.none.fl_str_mv |
Dovepress |
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reponame:CONICET Digital (CONICET) instname:Consejo Nacional de Investigaciones Científicas y Técnicas |
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CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicas |
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dasensio@conicet.gov.ar; lcarlino@conicet.gov.ar |
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