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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Bibliographic Details
Main Authors: Stefania Costa, Federico Zappaterra, Daniela Summa, Bruno Semeraro, Giancarlo Fantin
Format: Article
Language:English
Published: MDPI AG 2020-05-01
Series:Molecules
Subjects:
Online Access:https://www.mdpi.com/1420-3049/25/9/2192
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Summary: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.
ISSN:1420-3049