Chemical and biochemical approaches to the production of 7-hydroxylated C₁₉-steroids

Abstract

Interest has developed into 7-hydroxylated derivatives of 3β-hydroxylated C19-steroids, such as dehydroepiandrosterone (DHEA) and epiandrosterone because of their effects on inflammation, immune response, and cell repair. These steroids are not currently available from commercial sources, and it is necessary to produce them for relevant studies. We report here the chemical and biochemical approaches that were used for their production. Simplified chemical approaches lead to the production of 7α-/7β-hydroxy-DHEA and 7β-hydroxy-epiandrosterone in gram quantities, which are made available to researchers. Biochemical approaches were used to produce isotope-labeled compounds. Thus, 2H-, 3H-, and 14C-labeled 7α-/7β-hydroxy-DHEA and 7β-hydroxy-epiandrosterone could be produced in quantities sufficient for use in investigations into their mode of action.

The Quantitation of 7β-Hydroxy-Epiandrosterone in the Plasma and Seminal Plasma of Men With Different Degrees of Fertility

“…The steroids 7β-OH-EpiA and D2-7β-OH-EpiA were synthesized in Laboratoire de Chimie moléculaire, Conservatoire National des Arts et Métiers as previously described (Ferroud et al 2012, Ricco et al 2011. 2-hydrazinopyridine, ammonium formate and trifluoroacetic acid were from Sigma-Aldrich (St. Louis, Data are shown as means and 95.0 % confidence intervals (in the parentheses) for each group, the levels of significance of the model and multiple comparisons are provided.…”

Steroid Hormones and Homocysteine in the Outcome of Patients With Normal Pressure Hydrocephalus

“…An important portion of DHEA is transformed to DHEA 7-oxygenated derivatives, specifically 7α-hydroxy-DHEA, 7β-hydroxy- DHEA and their intermediate, 7-oxo-DHEA (Robinzon et al 2003, Seckl and Walker 2004, Muller et al 2006). These metabolites, showing similar effects to DHEA, may stay behind its beneficial properties (Morfin and Starka 2001, Kancheva et al 2010, Ferroud et al 2012). The 7-oxygenated DHEA metabolites are interconverted via type 1 11β-hydroxysteroid dehydrogenase (HSD11B1), which is also responsible for the interconversion of cortisol and cortisone in glucocorticoid responsive tissues including the brain (Seckl and Walker 2004, Muller et al 2006, Vitku et al 2014.…”