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
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/196445
Acceder
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network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling 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 Técnicas2025-10-22T11:30:08Zoai: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:34982025-10-22 11:30:08.566CONICET 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/
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 Dovepress
publisher.none.fl_str_mv Dovepress
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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