Δ1-Dehydrogenation and C20 Reduction of Cortisone and Hydrocortisone Catalyzed by <i>Rhodococcus</i> Strains
Prednisone and prednisolone are steroids widely used as anti-inflammatory drugs. Development of the pharmaceutical industry is currently aimed at introducing biotechnological processes and replacing multiple-stage chemical syntheses. In this work we evaluated the ability of bacteria belonging to the...
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MDPI AG
2020-05-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/25/9/2192 |
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| author | Stefania Costa Federico Zappaterra Daniela Summa Bruno Semeraro Giancarlo Fantin |
| author_facet | Stefania Costa Federico Zappaterra Daniela Summa Bruno Semeraro Giancarlo Fantin |
| author_sort | Stefania Costa |
| collection | DOAJ |
| description | Prednisone and prednisolone are steroids widely used as anti-inflammatory drugs. Development of the pharmaceutical industry is currently aimed at introducing biotechnological processes and replacing multiple-stage chemical syntheses. In this work we evaluated the ability of bacteria belonging to the <i>Rhodococcus</i> genus to biotransform substrates, such as cortisone and hydrocortisone, to obtain prednisone and prednisolone, respectively. These products are of great interest from a pharmaceutical point of view as they have higher anti-inflammatory activity than the starting substrates. After an initial lab-scale screening of 13 <i>Rhodococcus</i> strains, to select the highest producers of prednisone and prednisolone, we reported the 200 ml-batch scale-up to test the process efficiency and productivity of the most promising <i>Rhodococcus</i> strains. <i>R. ruber</i>, <i>R. globerulus</i> and <i>R. coprophilus</i> gave the Δ1-dehydrogenation products of cortisone and hydrocortisone (prednisone and prednisolone) in variable amounts. In these biotransformations, the formation of products with the reduced carbonyl group in position C<sub>20</sub> of the lateral chain of the steroid nucleus was also observed (i.e., 20β-hydroxy-prednisone and 20β-hydroxy-prednisolone). The yields, the absence of collateral products, and in some cases the absence of starting products allow us to say that cortisone and hydrocortisone are partly degraded. |
| first_indexed | 2024-03-10T19:58:29Z |
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| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-10T19:58:29Z |
| publishDate | 2020-05-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-7f53445f42c9498781487f60cd2ec83a2023-11-19T23:44:19ZengMDPI AGMolecules1420-30492020-05-01259219210.3390/molecules25092192Δ1-Dehydrogenation and C20 Reduction of Cortisone and Hydrocortisone Catalyzed by <i>Rhodococcus</i> StrainsStefania Costa0Federico Zappaterra1Daniela Summa2Bruno Semeraro3Giancarlo Fantin4Department of Life Sciences and Biotechnology, University of Ferrara, Via L. Borsari, 46, 44121 Ferrara, ItalyDepartment of Life Sciences and Biotechnology, University of Ferrara, Via L. Borsari, 46, 44121 Ferrara, ItalyGATE SRL, Via L. Borsari, 46, 44121 Ferrara, ItalyGATE SRL, Via L. Borsari, 46, 44121 Ferrara, ItalyDepartment of Chemical and Pharmaceutical Sciences, University of Ferrara, Via L. Borsari, 46, 44121 Ferrara, ItalyPrednisone and prednisolone are steroids widely used as anti-inflammatory drugs. Development of the pharmaceutical industry is currently aimed at introducing biotechnological processes and replacing multiple-stage chemical syntheses. In this work we evaluated the ability of bacteria belonging to the <i>Rhodococcus</i> genus to biotransform substrates, such as cortisone and hydrocortisone, to obtain prednisone and prednisolone, respectively. These products are of great interest from a pharmaceutical point of view as they have higher anti-inflammatory activity than the starting substrates. After an initial lab-scale screening of 13 <i>Rhodococcus</i> strains, to select the highest producers of prednisone and prednisolone, we reported the 200 ml-batch scale-up to test the process efficiency and productivity of the most promising <i>Rhodococcus</i> strains. <i>R. ruber</i>, <i>R. globerulus</i> and <i>R. coprophilus</i> gave the Δ1-dehydrogenation products of cortisone and hydrocortisone (prednisone and prednisolone) in variable amounts. In these biotransformations, the formation of products with the reduced carbonyl group in position C<sub>20</sub> of the lateral chain of the steroid nucleus was also observed (i.e., 20β-hydroxy-prednisone and 20β-hydroxy-prednisolone). The yields, the absence of collateral products, and in some cases the absence of starting products allow us to say that cortisone and hydrocortisone are partly degraded.https://www.mdpi.com/1420-3049/25/9/2192cortisonehydrocortisonebiotransformationsprednisoneprednisolone20β-hydroxy-prednisone |
| spellingShingle | Stefania Costa Federico Zappaterra Daniela Summa Bruno Semeraro Giancarlo Fantin Δ1-Dehydrogenation and C20 Reduction of Cortisone and Hydrocortisone Catalyzed by <i>Rhodococcus</i> Strains Molecules cortisone hydrocortisone biotransformations prednisone prednisolone 20β-hydroxy-prednisone |
| title | Δ1-Dehydrogenation and C20 Reduction of Cortisone and Hydrocortisone Catalyzed by <i>Rhodococcus</i> Strains |
| title_full | Δ1-Dehydrogenation and C20 Reduction of Cortisone and Hydrocortisone Catalyzed by <i>Rhodococcus</i> Strains |
| title_fullStr | Δ1-Dehydrogenation and C20 Reduction of Cortisone and Hydrocortisone Catalyzed by <i>Rhodococcus</i> Strains |
| title_full_unstemmed | Δ1-Dehydrogenation and C20 Reduction of Cortisone and Hydrocortisone Catalyzed by <i>Rhodococcus</i> Strains |
| title_short | Δ1-Dehydrogenation and C20 Reduction of Cortisone and Hydrocortisone Catalyzed by <i>Rhodococcus</i> Strains |
| title_sort | δ1 dehydrogenation and c20 reduction of cortisone and hydrocortisone catalyzed by i rhodococcus i strains |
| topic | cortisone hydrocortisone biotransformations prednisone prednisolone 20β-hydroxy-prednisone |
| url | https://www.mdpi.com/1420-3049/25/9/2192 |
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