Biosynthesis of 6β-hydroxymethyltestosterone using bovine hepatocyte cultures

• Published in: The Journal of steroid biochemistry and molecular biology 2000, Vol.74 (1), p.57-62
• Main Authors: Clouet-Dumas, Anne-Sophie, Le Bizec, Bruno, Le Pape, Marie-Annick, Maume, Daniel, Monteau, Fabrice, Andre, François
• Format: Article
• Language: English
• Subjects: 6β-Hydroxymethyltestosterone; Analytical chemistry; Biological and medical sciences; Biosynthesis; Bovine hepatocyte cultures; Chemical Sciences; Diverse techniques; Fundamental and applied biological sciences. Psychology; Life Sciences; Molecular and cellular biology; Santé publique et épidémiologie
• ISSN: 0960-0760; 1879-1220
• DOI: 10.1016/S0960-0760(00)00088-1

Usually performed to investigate biotransformations of xenobiotics, in vitro liver models could become useful tools for the synthesis of not commercially available compounds. In this study, bovine hepatocyte cultures were used to biosynthesise, on the laboratory scale, one major metabolite of methyltestosterone: 6β-hydroxymethyltestosterone. After incubation of bovine hepatocytes with methyltestosterone for 24 h, culture medium was removed and stored at −20°C until analysis. The sample was extracted and purified on a reversed-phase HPLC system. The metabolite of interest was then analysed in LC-MS and GC-MS for structural identification. The purity and the isomery of the 6 and 17 positions were confirmed by NMR analyses. This first success in producing purified 6β-hydroxymethyltestosterone from bovine hepatocyte cultures allowed us to consider that in vitro liver models could be reliable tools for standard biosynthesis.