New metabolites of drospirenone obtained in Mucorales fungi culture

Autores
Quintana, Paula Gabriela; Romero, Stella Maris; Vaamonde, Graciela; Baldessari, Alicia
Año de publicación
2013
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
Microbial transformation of 6,7,15,16-dimethylene-3-oxo-17-pregn-4-ene-2, 17-carbo-lactone, the well-known contraceptive drospirenone (1), using fungal cells was carried out. Six fungal strains of different species of Order Mucorales were evaluated in this study, namely Absidia corymbifera BAFC 1072, Absidia corymbifera BAFC 1080, A. coerulea, Mucor plumbeus BAFC 2314, Rhizopus oryzae and Syncephalastrum racemosum. Four products were obtained by hydroxylation at C-11 and C-2 and epimerization at C-17 of drospirenone by A. corymbifera BAFC 1072, A. coerulea and S. racemosum. The structures were elucidated as 6β,7β,15β,16β-dimethylene-11α-hydroxy-3- oxo-l7α-pregn-4-en-21,17-carbolactone (2), 6β,7β,15β, 16β-dimethylene-11α-hydroxy-3-oxo-l7β-pregn-4-en-21, 17-carbolactone (3), 6β,7β,15β,16β-dimethylene-11β- hydroxy-3-oxo-l7α-pregn-4-en-21,17-carbolactone (4) and 6β,7β,15β,16β-dimethylene-2β-hydroxy-3-oxo-l7α- pregn-4-en-21,17-carbolactone (5), on the basis of extensive spectral data including 2D NMR spectroscopy and MS. Products 3, 4 and 5 were found to be new compounds. Several biotransformation parameters such as the employment of growing or resting cells, inoculum size, agitation speed, drospirenone concentration, temperature, pH and presence of co-solvent were seen to be important to the optimization of the process.
Fil: Quintana, Paula Gabriela. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Unidad de Microanálisis y Métodos Físicos en Química Orgánica. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Unidad de Microanálisis y Métodos Físicos en Química Orgánica; Argentina
Fil: Romero, Stella Maris. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Instituto de Micología y Botánica. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Instituto de Micología y Botánica; Argentina
Fil: Vaamonde, Graciela. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Instituto de Micología y Botánica. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Instituto de Micología y Botánica; Argentina
Fil: Baldessari, Alicia. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Unidad de Microanálisis y Métodos Físicos en Química Orgánica. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Unidad de Microanálisis y Métodos Físicos en Química Orgánica; Argentina
Materia
Biotransformation
Drospirenone
Epimerization
Hydroxylation
Mucorales
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:11336/78166
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/78166
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling New metabolites of drospirenone obtained in Mucorales fungi cultureQuintana, Paula GabrielaRomero, Stella MarisVaamonde, GracielaBaldessari, AliciaBiotransformationDrospirenoneEpimerizationHydroxylationMucoraleshttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1Microbial transformation of 6,7,15,16-dimethylene-3-oxo-17-pregn-4-ene-2, 17-carbo-lactone, the well-known contraceptive drospirenone (1), using fungal cells was carried out. Six fungal strains of different species of Order Mucorales were evaluated in this study, namely Absidia corymbifera BAFC 1072, Absidia corymbifera BAFC 1080, A. coerulea, Mucor plumbeus BAFC 2314, Rhizopus oryzae and Syncephalastrum racemosum. Four products were obtained by hydroxylation at C-11 and C-2 and epimerization at C-17 of drospirenone by A. corymbifera BAFC 1072, A. coerulea and S. racemosum. The structures were elucidated as 6β,7β,15β,16β-dimethylene-11α-hydroxy-3- oxo-l7α-pregn-4-en-21,17-carbolactone (2), 6β,7β,15β, 16β-dimethylene-11α-hydroxy-3-oxo-l7β-pregn-4-en-21, 17-carbolactone (3), 6β,7β,15β,16β-dimethylene-11β- hydroxy-3-oxo-l7α-pregn-4-en-21,17-carbolactone (4) and 6β,7β,15β,16β-dimethylene-2β-hydroxy-3-oxo-l7α- pregn-4-en-21,17-carbolactone (5), on the basis of extensive spectral data including 2D NMR spectroscopy and MS. Products 3, 4 and 5 were found to be new compounds. Several biotransformation parameters such as the employment of growing or resting cells, inoculum size, agitation speed, drospirenone concentration, temperature, pH and presence of co-solvent were seen to be important to the optimization of the process.Fil: Quintana, Paula Gabriela. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Unidad de Microanálisis y Métodos Físicos en Química Orgánica. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Unidad de Microanálisis y Métodos Físicos en Química Orgánica; ArgentinaFil: Romero, Stella Maris. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Instituto de Micología y Botánica. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Instituto de Micología y Botánica; ArgentinaFil: Vaamonde, Graciela. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Instituto de Micología y Botánica. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Instituto de Micología y Botánica; ArgentinaFil: Baldessari, Alicia. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Unidad de Microanálisis y Métodos Físicos en Química Orgánica. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Unidad de Microanálisis y Métodos Físicos en Química Orgánica; ArgentinaElsevier Science2013-12-15info: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/11336/78166Quintana, Paula Gabriela; Romero, Stella Maris; Vaamonde, Graciela; Baldessari, Alicia; New metabolites of drospirenone obtained in Mucorales fungi culture; Elsevier Science; Journal of Molecular Catalysis B: Enzymatic; 97; 15-12-2013; 110-1171381-1177CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/pii/S1381117713002348info:eu-repo/semantics/altIdentifier/doi/10.1016/j.molcatb.2013.08.005info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-03T10:07:53Zoai:ri.conicet.gov.ar:11336/78166instacron: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 10:07:53.586CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv New metabolites of drospirenone obtained in Mucorales fungi culture
title New metabolites of drospirenone obtained in Mucorales fungi culture
spellingShingle New metabolites of drospirenone obtained in Mucorales fungi culture
Quintana, Paula Gabriela
Biotransformation
Drospirenone
Epimerization
Hydroxylation
Mucorales
title_short New metabolites of drospirenone obtained in Mucorales fungi culture
title_full New metabolites of drospirenone obtained in Mucorales fungi culture
title_fullStr New metabolites of drospirenone obtained in Mucorales fungi culture
title_full_unstemmed New metabolites of drospirenone obtained in Mucorales fungi culture
title_sort New metabolites of drospirenone obtained in Mucorales fungi culture
dc.creator.none.fl_str_mv Quintana, Paula Gabriela
Romero, Stella Maris
Vaamonde, Graciela
Baldessari, Alicia
author Quintana, Paula Gabriela
author_facet Quintana, Paula Gabriela
Romero, Stella Maris
Vaamonde, Graciela
Baldessari, Alicia
author_role author
author2 Romero, Stella Maris
Vaamonde, Graciela
Baldessari, Alicia
author2_role author
author
author
dc.subject.none.fl_str_mv Biotransformation
Drospirenone
Epimerization
Hydroxylation
Mucorales
topic Biotransformation
Drospirenone
Epimerization
Hydroxylation
Mucorales
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv Microbial transformation of 6,7,15,16-dimethylene-3-oxo-17-pregn-4-ene-2, 17-carbo-lactone, the well-known contraceptive drospirenone (1), using fungal cells was carried out. Six fungal strains of different species of Order Mucorales were evaluated in this study, namely Absidia corymbifera BAFC 1072, Absidia corymbifera BAFC 1080, A. coerulea, Mucor plumbeus BAFC 2314, Rhizopus oryzae and Syncephalastrum racemosum. Four products were obtained by hydroxylation at C-11 and C-2 and epimerization at C-17 of drospirenone by A. corymbifera BAFC 1072, A. coerulea and S. racemosum. The structures were elucidated as 6β,7β,15β,16β-dimethylene-11α-hydroxy-3- oxo-l7α-pregn-4-en-21,17-carbolactone (2), 6β,7β,15β, 16β-dimethylene-11α-hydroxy-3-oxo-l7β-pregn-4-en-21, 17-carbolactone (3), 6β,7β,15β,16β-dimethylene-11β- hydroxy-3-oxo-l7α-pregn-4-en-21,17-carbolactone (4) and 6β,7β,15β,16β-dimethylene-2β-hydroxy-3-oxo-l7α- pregn-4-en-21,17-carbolactone (5), on the basis of extensive spectral data including 2D NMR spectroscopy and MS. Products 3, 4 and 5 were found to be new compounds. Several biotransformation parameters such as the employment of growing or resting cells, inoculum size, agitation speed, drospirenone concentration, temperature, pH and presence of co-solvent were seen to be important to the optimization of the process.
Fil: Quintana, Paula Gabriela. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Unidad de Microanálisis y Métodos Físicos en Química Orgánica. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Unidad de Microanálisis y Métodos Físicos en Química Orgánica; Argentina
Fil: Romero, Stella Maris. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Instituto de Micología y Botánica. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Instituto de Micología y Botánica; Argentina
Fil: Vaamonde, Graciela. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Instituto de Micología y Botánica. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Instituto de Micología y Botánica; Argentina
Fil: Baldessari, Alicia. Consejo Nacional de Investigaciones Científicas y Técnicas. Oficina de Coordinación Administrativa Ciudad Universitaria. Unidad de Microanálisis y Métodos Físicos en Química Orgánica. Universidad de Buenos Aires. Facultad de Ciencias Exactas y Naturales. Unidad de Microanálisis y Métodos Físicos en Química Orgánica; Argentina
description Microbial transformation of 6,7,15,16-dimethylene-3-oxo-17-pregn-4-ene-2, 17-carbo-lactone, the well-known contraceptive drospirenone (1), using fungal cells was carried out. Six fungal strains of different species of Order Mucorales were evaluated in this study, namely Absidia corymbifera BAFC 1072, Absidia corymbifera BAFC 1080, A. coerulea, Mucor plumbeus BAFC 2314, Rhizopus oryzae and Syncephalastrum racemosum. Four products were obtained by hydroxylation at C-11 and C-2 and epimerization at C-17 of drospirenone by A. corymbifera BAFC 1072, A. coerulea and S. racemosum. The structures were elucidated as 6β,7β,15β,16β-dimethylene-11α-hydroxy-3- oxo-l7α-pregn-4-en-21,17-carbolactone (2), 6β,7β,15β, 16β-dimethylene-11α-hydroxy-3-oxo-l7β-pregn-4-en-21, 17-carbolactone (3), 6β,7β,15β,16β-dimethylene-11β- hydroxy-3-oxo-l7α-pregn-4-en-21,17-carbolactone (4) and 6β,7β,15β,16β-dimethylene-2β-hydroxy-3-oxo-l7α- pregn-4-en-21,17-carbolactone (5), on the basis of extensive spectral data including 2D NMR spectroscopy and MS. Products 3, 4 and 5 were found to be new compounds. Several biotransformation parameters such as the employment of growing or resting cells, inoculum size, agitation speed, drospirenone concentration, temperature, pH and presence of co-solvent were seen to be important to the optimization of the process.
publishDate 2013
dc.date.none.fl_str_mv 2013-12-15
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/11336/78166
Quintana, Paula Gabriela; Romero, Stella Maris; Vaamonde, Graciela; Baldessari, Alicia; New metabolites of drospirenone obtained in Mucorales fungi culture; Elsevier Science; Journal of Molecular Catalysis B: Enzymatic; 97; 15-12-2013; 110-117
1381-1177
CONICET Digital
CONICET
url http://hdl.handle.net/11336/78166
identifier_str_mv Quintana, Paula Gabriela; Romero, Stella Maris; Vaamonde, Graciela; Baldessari, Alicia; New metabolites of drospirenone obtained in Mucorales fungi culture; Elsevier Science; Journal of Molecular Catalysis B: Enzymatic; 97; 15-12-2013; 110-117
1381-1177
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.sciencedirect.com/science/article/pii/S1381117713002348
info:eu-repo/semantics/altIdentifier/doi/10.1016/j.molcatb.2013.08.005
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 Elsevier Science
publisher.none.fl_str_mv Elsevier Science
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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