Ergosteroids II: Biologically Active Metabolites and Synthetic Derivatives of Dehydroepiandrosterone
Identifieur interne : 00B371 ( Main/Exploration ); précédent : 00B370; suivant : 00B372Ergosteroids II: Biologically Active Metabolites and Synthetic Derivatives of Dehydroepiandrosterone
Auteurs : Henry Lardy [États-Unis] ; Nancy Kneer [États-Unis] ; Yong Wei [États-Unis] ; Bruce Partridge [États-Unis] ; Padma Marwah [États-Unis]Source :
- Steroids [ 0039-128X ] ; 1998.
English descriptors
- KwdEn :
- Teeft :
- Acetic acid, Active derivatives, Acyl, Acyl esters, Adrenal carcinoma, Antiobesity effect, Biol, Body weight, Cdcl3, Cell fractions, Chem, Clin, Control rats, Cytosolic, Cytosolic malic enzyme, Dehydroepiandrosterone, Dehydrogenase, Derivative, Dhea, Dhea acetate, Double bond, Elsevier science, Endocrinol, Enzyme, Enzyme activities, Enzyme activity, Enzyme induction, Enzyme research, Ester, Ethyl acetate, Fatty acyl esters, Hepatic microsomes, Human plasma, Lardy, Liver enzymes, Malic, Malic enzyme, Mammalian tissues, Mitochondrial, Mitochondrial dehydrogenase, Mitochondrial glycerophosphate dehydrogenase, Mother liquor, Ococh3, Pregnenolone, Proc natl acad, Room temperature, Second crop, Silver acetate, Single experiment, Steroid, Thermogenic, Thermogenic enzymes.
Abstract
Abstract: An improved procedure for the synthesis of 3β-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 17β-hydroxy derivative, or hydroxylated at 7α or 7β, 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 many steroids tested, those possessing a carbonyl group at position 3, a methyl group at 7, a hydroxyl group at positions 1, 2, 4, 11, or 19, or a saturated B ring, with or without a 4-5 double bond, were inactive.
Url:
DOI: 10.1016/S0039-128X(97)00159-1
Affiliations:
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type="state">Wisconsin</region></placeName></affiliation></author></analytic><monogr></monogr><series><title level="j">Steroids</title><title level="j" type="abbrev">STE</title><idno type="ISSN">0039-128X</idno><imprint><publisher>ELSEVIER</publisher><date type="published" when="1998">1998</date><biblScope unit="volume">63</biblScope><biblScope unit="issue">3</biblScope><biblScope unit="page" from="158">158</biblScope><biblScope unit="page" to="165">165</biblScope></imprint><idno type="ISSN">0039-128X</idno></series></biblStruct></sourceDesc><seriesStmt><idno type="ISSN">0039-128X</idno></seriesStmt></fileDesc><profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>7-oxo-dehydroepiandrosterone</term><term>DHEA</term><term>acyl esters of 7-oxo-DHEA</term><term>ergosteroids</term></keywords><keywords scheme="Teeft" xml:lang="en"><term>Acetic acid</term><term>Active derivatives</term><term>Acyl</term><term>Acyl esters</term><term>Adrenal carcinoma</term><term>Antiobesity effect</term><term>Biol</term><term>Body weight</term><term>Cdcl3</term><term>Cell fractions</term><term>Chem</term><term>Clin</term><term>Control rats</term><term>Cytosolic</term><term>Cytosolic malic enzyme</term><term>Dehydroepiandrosterone</term><term>Dehydrogenase</term><term>Derivative</term><term>Dhea</term><term>Dhea acetate</term><term>Double bond</term><term>Elsevier science</term><term>Endocrinol</term><term>Enzyme</term><term>Enzyme activities</term><term>Enzyme activity</term><term>Enzyme induction</term><term>Enzyme research</term><term>Ester</term><term>Ethyl acetate</term><term>Fatty acyl esters</term><term>Hepatic microsomes</term><term>Human plasma</term><term>Lardy</term><term>Liver enzymes</term><term>Malic</term><term>Malic enzyme</term><term>Mammalian tissues</term><term>Mitochondrial</term><term>Mitochondrial dehydrogenase</term><term>Mitochondrial glycerophosphate dehydrogenase</term><term>Mother liquor</term><term>Ococh3</term><term>Pregnenolone</term><term>Proc natl acad</term><term>Room temperature</term><term>Second crop</term><term>Silver acetate</term><term>Single experiment</term><term>Steroid</term><term>Thermogenic</term><term>Thermogenic enzymes</term></keywords></textClass><langUsage><language ident="en">en</language></langUsage></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">Abstract: An improved procedure for the synthesis of 3β-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 17β-hydroxy derivative, or hydroxylated at 7α or 7β, 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 many steroids tested, those possessing a carbonyl group at position 3, a methyl group at 7, a hydroxyl group at positions 1, 2, 4, 11, or 19, or a saturated B ring, with or without a 4-5 double bond, were inactive.</div></front></TEI><affiliations><list><country><li>États-Unis</li></country><region><li>Wisconsin</li></region></list><tree><country name="États-Unis"><region name="Wisconsin"><name sortKey="Lardy, Henry" sort="Lardy, Henry" uniqKey="Lardy H" first="Henry" last="Lardy">Henry Lardy</name></region><name sortKey="Kneer, Nancy" sort="Kneer, Nancy" uniqKey="Kneer N" first="Nancy" last="Kneer">Nancy Kneer</name><name sortKey="Marwah, Padma" sort="Marwah, Padma" uniqKey="Marwah P" first="Padma" last="Marwah">Padma Marwah</name><name sortKey="Partridge, Bruce" sort="Partridge, Bruce" uniqKey="Partridge B" first="Bruce" last="Partridge">Bruce Partridge</name><name sortKey="Wei, Yong" sort="Wei, Yong" uniqKey="Wei Y" first="Yong" last="Wei">Yong Wei</name></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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