Abstract

Cortisone is a steroid widely used as an anti-inflammatory drug able to suppress the immune system, thus reducing inflammation and attendant pain and swelling at the site of an injury. Due to its numerous side effects, especially in prolonged and high-dose therapies, the development of the pharmaceutical industry is currently aimed at finding new compounds with similar activities but with minor or no side effects. Biotransformations are an important methodology towards more sustainable industrial processes, according to the principles of “green chemistry”. In this work, the biotransformation of cortisone with Rhodococcus rhodnii DSM 43960 to give two new steroids, i.e., 1,9β,17,21-tetrahydoxy-4-methyl-19-nor-9β-pregna-1,3,5(10)-trien-11,20-dione and 1,9β,17,20β,21-pentahydoxy-4-methyl-19-nor-9β-pregna-1,3,5(10)-trien-11-one, is reported. These new steroids have been fully characterized.

Highlights

  • Steroid drugs are used for various therapeutic applications and represent the most marketed drug category after antibiotics, with an annual production of over one million tons

  • Steroids belonging to the glucocorticoid class can control the metabolism of carbohydrates, lipids, and proteins, while mineralocorticoids control the concentration of electrolytes and, the amount of water present in the blood [2]

  • After 24 h of biotransformation, the only visible bands were those relating to products 1,9β,17,21-tetrahydroxy-4-methyl-19-nor-9β-pregna-1,3,5(10)-trien-11,20-dione (6) and 1,9β,17,20β,21-pentahydroxy-4-methyl-19-nor-9β-pregna-1,3,5(10)-trien-11-one (7)

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Summary

Introduction

Steroid drugs are used for various therapeutic applications and represent the most marketed drug category after antibiotics, with an annual production of over one million tons. There are about 300 steroid-based drugs on the market, and this is constantly growing [1]. In this field, corticosteroids are a group of hormones produced by the adrenal gland cortex. Corticosteroids are a group of hormones produced by the adrenal gland cortex This type of molecule is used for its anti-inflammatory, immunosuppressive properties and for its effects on metabolism. Steroids belonging to the glucocorticoid class can control the metabolism of carbohydrates, lipids, and proteins, while mineralocorticoids control the concentration of electrolytes and, the amount of water present in the blood [2]. Glucocorticoids play an important role in anti-inflammatory and immunosuppressive therapy [3] and are widely used in the treatment of allergic reactions and inflammatory and autoimmune diseases, as well as in the prevention of rejection in transplants and the treatment of hematological neoplasia [4]

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