Enzymatic Synthesis of Anabolic Steroid Glycosides by Glucosyltransferase from Terribacillus sp. PAMC 23288.

Abstract

The application of steroids has steadily increased thanks to their therapeutic effects. However, alternatives are required due their severe side effects; thus, studies on the activities of steroid derivatives are underway. Sugar derivatives of nandrolone, which is used to treat breast cancer, as well as cortisone and prednisone, which reduce inflammation, pain, and edema, are unknown. We linked O-glucose to nandrolone and testosterone using UDP-glucosyltransferase (UGT-1) and, then, tested their bioactivities in vitro. Analysis by NMR showed that the derivatives were 17β-nandrolone β-D-glucose and 17β-testosterone β-D-glucose, respectively. The viability was higher and cytotoxicity was evident in PC12 cells incubated with rotenone and, testosterone derivatives, compared to the controls. SH-SY5Y cells incubated with H2O2 and nandrolone derivatives remained viable and cytotoxicity was attenuated. Both derivatives enhanced neuronal protective effects and increased the amounts of cellular ATP.

• Authors: Eun-Ji Yu, Tokutaro Yamaguchi, Joo-Ho Lee, A-Rang Lim, Jun Hyuck Lee, Hyun Park, Tae-Jin Oh
• Journal: Journal of microbiology and biotechnology (J Microbiol Biotechnol) Vol. 30 Issue 4 Pg. 604-614 (Apr 28 2020) ISSN: 1738-8872 [Electronic] Korea (South)
• PMID: 31893610 (Publication Type: Journal Article)

Chemical References

• Bacterial Proteins
• Glycosides
• Neuroprotective Agents
• Testosterone Congeners
• Testosterone
• Nandrolone
• Adenosine Triphosphate
• Glucosyltransferases
• Glucose

Topics

• Adenosine Triphosphate (metabolism)
• Animals
• Bacillaceae (enzymology)
• Bacterial Proteins (metabolism)
• Biotransformation
• Cell Line, Tumor
• Energy Metabolism (drug effects)
• Glucose (chemistry, metabolism)
• Glucosyltransferases (metabolism)
• Glycosides (chemistry, metabolism, pharmacology)
• Humans
• Nandrolone (chemistry, metabolism)
• Neuroprotective Agents (chemistry, metabolism, pharmacology)
• PC12 Cells
• Rats
• Testosterone (chemistry, metabolism)
• Testosterone Congeners (chemistry, metabolism, pharmacology)