Chromatographic and mass spectrometric characteristics of 20-dihydroaldosterone

Steroids. 1992 Oct;57(10):480-4. doi: 10.1016/0039-128x(92)90041-7.

Abstract

The 20 alpha-reduced derivative of aldosterone, 20 alpha-dihydroaldosterone, was needed as reference compound in order to continue the studies on 18-hydroxylation in the Y-1 adrenal cell line. It was obtained by reduction of aldosterone with sodium borohydride. Analysis of the products of the reaction as methoxime trimethylsilyl (MO-TMS) derivatives by gas chromatography (GC) and GC-mass spectrometry (GC-MS) showed three possible forms of the compound. Their identification was confirmed by comparison with the products obtained by stereospecific reduction of aldosterone using 3 alpha,20 beta-hydroxysteroid dehydrogenase. Chromatographic behavior and mass spectra are given for the three forms of 20 alpha-dihydroaldosterone as the MO-TMS derivatives; that is, the 18-aldehyde, the 18,11 beta-hemiacetal, and the 11 beta:18,18:20 alpha-acetal. The possible origin of these different forms is discussed as a function of these results and of the results obtained by complementary analysis on high-performance liquid chromatography.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aldosterone / analogs & derivatives*
  • Aldosterone / chemistry
  • Borohydrides
  • Chromatography, Gas
  • Chromatography, High Pressure Liquid
  • Deuterium
  • Ethers
  • Gas Chromatography-Mass Spectrometry
  • Molecular Structure
  • Oxidation-Reduction
  • Reference Standards
  • Trimethylsilyl Compounds / chemistry

Substances

  • 20-dihydroaldosterone
  • Borohydrides
  • Ethers
  • Trimethylsilyl Compounds
  • Aldosterone
  • sodium borohydride
  • Deuterium