New metabolites of drospirenone obtained in Mucorales fungi culture
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...
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2013
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| Acceso en línea: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_13811177_v97_n_p110_Quintana http://hdl.handle.net/20.500.12110/paper_13811177_v97_n_p110_Quintana |
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paper:paper_13811177_v97_n_p110_Quintana2023-06-08T16:12:22Z New metabolites of drospirenone obtained in Mucorales fungi culture Biotransformation Drospirenone Epimerization Hydroxylation Mucorales 2D-NMR spectroscopy Agitation speed Biotransformation Drospirenone Epimerization Microbial transformation Mucorales Rhizopus oryzae Nuclear magnetic resonance spectroscopy Hydroxylation 6beta,7beta,15beta,16beta dimethylene 11alpha hydroxy 3 oxo 17alpha pregn 4 en 21,17 carbolactone 6beta,7beta,15beta,16beta dimethylene 11alpha hydroxy 3 oxo 17beta pregn 4 en 21,17 carbolactone 6beta,7beta,15beta,16beta dimethylene 11beta hydroxy 3 oxo 17alpha pregn 4 en 21,17 carbolactone 6beta,7beta,15beta,16beta dimethylene 2beta hydroxy 3 oxo 17alpha pregn 4 en 21,17 carbolactone drospirenone lactone derivative solvent unclassified drug Absidia absidia coerulea agitation animal cell article Candida Candida aphidicola cell growth chemical structure controlled study drug determination drug hydroxylation drug metabolism drug transformation epimerization fungal cell fungal strain fungus fungus culture inoculation metabolite Mucor mucor plumbeus Mucorales nonhuman nuclear magnetic resonance spectroscopy pH pharmacological parameters process optimization Rhizopus oryzae stereochemistry syncephalastrum racemosum temperature Zygomycetes Absidia corymbifera Fungi Mucor plumbeus Mucorales Rhizopus oryzae Syncephalastrum racemosum 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. © 2013 Elsevier B.V. All rights reserved. 2013 https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_13811177_v97_n_p110_Quintana http://hdl.handle.net/20.500.12110/paper_13811177_v97_n_p110_Quintana |
| institution |
Universidad de Buenos Aires |
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I-28 |
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R-134 |
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Biblioteca Digital - Facultad de Ciencias Exactas y Naturales (UBA) |
| topic |
Biotransformation Drospirenone Epimerization Hydroxylation Mucorales 2D-NMR spectroscopy Agitation speed Biotransformation Drospirenone Epimerization Microbial transformation Mucorales Rhizopus oryzae Nuclear magnetic resonance spectroscopy Hydroxylation 6beta,7beta,15beta,16beta dimethylene 11alpha hydroxy 3 oxo 17alpha pregn 4 en 21,17 carbolactone 6beta,7beta,15beta,16beta dimethylene 11alpha hydroxy 3 oxo 17beta pregn 4 en 21,17 carbolactone 6beta,7beta,15beta,16beta dimethylene 11beta hydroxy 3 oxo 17alpha pregn 4 en 21,17 carbolactone 6beta,7beta,15beta,16beta dimethylene 2beta hydroxy 3 oxo 17alpha pregn 4 en 21,17 carbolactone drospirenone lactone derivative solvent unclassified drug Absidia absidia coerulea agitation animal cell article Candida Candida aphidicola cell growth chemical structure controlled study drug determination drug hydroxylation drug metabolism drug transformation epimerization fungal cell fungal strain fungus fungus culture inoculation metabolite Mucor mucor plumbeus Mucorales nonhuman nuclear magnetic resonance spectroscopy pH pharmacological parameters process optimization Rhizopus oryzae stereochemistry syncephalastrum racemosum temperature Zygomycetes Absidia corymbifera Fungi Mucor plumbeus Mucorales Rhizopus oryzae Syncephalastrum racemosum |
| spellingShingle |
Biotransformation Drospirenone Epimerization Hydroxylation Mucorales 2D-NMR spectroscopy Agitation speed Biotransformation Drospirenone Epimerization Microbial transformation Mucorales Rhizopus oryzae Nuclear magnetic resonance spectroscopy Hydroxylation 6beta,7beta,15beta,16beta dimethylene 11alpha hydroxy 3 oxo 17alpha pregn 4 en 21,17 carbolactone 6beta,7beta,15beta,16beta dimethylene 11alpha hydroxy 3 oxo 17beta pregn 4 en 21,17 carbolactone 6beta,7beta,15beta,16beta dimethylene 11beta hydroxy 3 oxo 17alpha pregn 4 en 21,17 carbolactone 6beta,7beta,15beta,16beta dimethylene 2beta hydroxy 3 oxo 17alpha pregn 4 en 21,17 carbolactone drospirenone lactone derivative solvent unclassified drug Absidia absidia coerulea agitation animal cell article Candida Candida aphidicola cell growth chemical structure controlled study drug determination drug hydroxylation drug metabolism drug transformation epimerization fungal cell fungal strain fungus fungus culture inoculation metabolite Mucor mucor plumbeus Mucorales nonhuman nuclear magnetic resonance spectroscopy pH pharmacological parameters process optimization Rhizopus oryzae stereochemistry syncephalastrum racemosum temperature Zygomycetes Absidia corymbifera Fungi Mucor plumbeus Mucorales Rhizopus oryzae Syncephalastrum racemosum New metabolites of drospirenone obtained in Mucorales fungi culture |
| topic_facet |
Biotransformation Drospirenone Epimerization Hydroxylation Mucorales 2D-NMR spectroscopy Agitation speed Biotransformation Drospirenone Epimerization Microbial transformation Mucorales Rhizopus oryzae Nuclear magnetic resonance spectroscopy Hydroxylation 6beta,7beta,15beta,16beta dimethylene 11alpha hydroxy 3 oxo 17alpha pregn 4 en 21,17 carbolactone 6beta,7beta,15beta,16beta dimethylene 11alpha hydroxy 3 oxo 17beta pregn 4 en 21,17 carbolactone 6beta,7beta,15beta,16beta dimethylene 11beta hydroxy 3 oxo 17alpha pregn 4 en 21,17 carbolactone 6beta,7beta,15beta,16beta dimethylene 2beta hydroxy 3 oxo 17alpha pregn 4 en 21,17 carbolactone drospirenone lactone derivative solvent unclassified drug Absidia absidia coerulea agitation animal cell article Candida Candida aphidicola cell growth chemical structure controlled study drug determination drug hydroxylation drug metabolism drug transformation epimerization fungal cell fungal strain fungus fungus culture inoculation metabolite Mucor mucor plumbeus Mucorales nonhuman nuclear magnetic resonance spectroscopy pH pharmacological parameters process optimization Rhizopus oryzae stereochemistry syncephalastrum racemosum temperature Zygomycetes Absidia corymbifera Fungi Mucor plumbeus Mucorales Rhizopus oryzae Syncephalastrum racemosum |
| 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. © 2013 Elsevier B.V. All rights reserved. |
| title |
New metabolites of drospirenone obtained in Mucorales fungi culture |
| 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 |
| publishDate |
2013 |
| url |
https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_13811177_v97_n_p110_Quintana http://hdl.handle.net/20.500.12110/paper_13811177_v97_n_p110_Quintana |
| _version_ |
1768546457711804416 |