PMID: 9558717Apr 29, 1998Paper

Ergosteroids. II: Biologically active metabolites and synthetic derivatives of dehydroepiandrosterone

Steroids
H LardyP Marwah

Abstract

An improved procedure for the synthesis of 3 beta-hydroxyandrost-5-ene-7,17-dione, a natural metabolite of dehydroepiandrosterone (DHEA) is described. The synthesis and magnetic resonance spectra of several other related steroids are presented. Feeding dehydroepiandrosterone to rats induces enhanced formation of several liver enzymes among which are mitochondrial sn-glycerol 3-phosphate dehydrogenase (GPDH) and cytosolic malic enzyme. The induction of these two enzymes, that complete a thermogenic system in rat liver, was used as an assay to search for derivatives of DHEA that might be more active than the parent steroid. Activity is retained in steroids that are reduced to the corresponding 17 beta-hydroxy derivative, or hydroxylated at 7 alpha or 7 beta, and is considerably enhanced when the 17-hydroxy or 17-carbonyl steroid is converted to the 7-oxo derivative. Several derivatives of DHEA did not induce the thermogenic enzymes whereas the corresponding 7-oxo compounds did. Both short and long chain acyl esters of DHEA and of 7-oxo-DHEA are active inducers of the liver enzymes when fed to rats. 7-Oxo-DHEA-3-sulfate is as active as 7-oxo-DHEA or its 3-acetyl ester, whereas DHEA-3-sulfate is much less active than DHEA. Among ma...Continue Reading

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Citations

Mar 6, 2003·Lipids·Henry LardyPadma Marwah
Feb 23, 2005·Nutrition·John L ZenkMichael A Kuskowski
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Mar 12, 2002·Journal of Chromatography. B, Analytical Technologies in the Biomedical and Life Sciences·Ashok MarwahHenry Lardy

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