Microbial oxidation of anabolic steroids

Area of Science:

• Biochemistry
• Microbiology
• Organic Chemistry

Background:

• Anabolic steroids are synthetic derivatives of testosterone.
• Microbial transformations offer a sustainable approach to steroid modification.
• Understanding biotransformation pathways is crucial for drug development and metabolism studies.

Purpose of the Study:

• To investigate the microbial transformation of ethylestrenol and nandrolone.
• To identify the oxidative metabolites produced by Rhizopus stolonifer.
• To elucidate the biotransformation pathways of these anabolic steroids.

Main Methods:

• Incubation of ethylestrenol (1) and nandrolone (2) with Rhizopus stolonifer (TSY 0471).
• Isolation and characterization of resulting metabolites using analytical techniques.
• Chemical structure elucidation of the identified oxidative metabolites.

Main Results:

• Ethylestrenol yielded two oxidative metabolites: 17alpha-ethyl-3beta,17beta-dihydroxy-19-norandrost-4-ene (3) and 17alpha-ethyl-17beta-hydroxy-19-norandrost-4-en-3-one (4).
• Nandrolone yielded two oxidative metabolites: 19-norandrost-4-en-3,17-dione (5) and 6alpha,17beta-dihydroxy-19-norandrost-1,4-dien-3-one (6).
• Rhizopus stolonifer demonstrated specific oxidative capabilities towards both steroids.

Conclusions:

• Rhizopus stolonifer effectively transforms ethylestrenol and nandrolone through oxidation.
• The study identified novel metabolites, contributing to the understanding of steroid biotransformation.
• These findings have implications for biocatalysis and the study of steroid metabolism.