Abstract
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 Rhodococcus 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 Rhodococcus 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 Rhodococcus strains. R. ruber, R. globerulus and R. coprophilus 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 C20 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.
Highlights
IntroductionSteroids are lipids belonging to the terpenes class, and from a chemical-structural point of view they contain a tetracyclic system of carbon atoms (cyclopentanoperhydrophenanthrene)
Steroids are lipids belonging to the terpenes class, and from a chemical-structural point of view they contain a tetracyclic system of carbon atoms.This type of compound is widespread in nature: thousands of steroids have been identified in living systems
In this work we evaluated the ability of bacteria belonging to the Rhodococcus genus to biotransform substrates, such as cortisone and hydrocortisone, to obtain prednisone and prednisolone, respectively
Summary
Steroids are lipids belonging to the terpenes class, and from a chemical-structural point of view they contain a tetracyclic system of carbon atoms (cyclopentanoperhydrophenanthrene). This type of compound is widespread in nature: thousands of steroids have been identified in living systems. Steroid-based drugs present a broad range of therapeutic applications and represent the highest marketed category of pharmaceuticals, after antibiotics, with an annual production of more than one Molecules 2020, 25, 2192; doi:10.3390/molecules25092192 www.mdpi.com/journal/molecules. About 300 steroid drugs are known, and this number tends to grow. Their production represents the second category in the pharmaceutical market after antibiotics [4]
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