Identification of 16-dehydropregnenolone as an intermediate in 16-androstene biosynthesis in neonatal porcine testicular microsomes

The biosynthesis of 16-androstenes has been studied in neonatal porcine testicular microsomes using 17-hydroxypregnenolone and 16-dehydropregnenolone, separately, as substrates. The metabolites formed after microsomal incubation with these substrates were purified, derivatized as O-methyloxime-trime...

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Bibliographic Details
Published in:FEBS letters 1984-08, Vol.174 (1), p.173-178
Main Authors: Kwan, T.K., Taylor, N.F., Watson, D., Gower, D.B.
Format: Article
Language:English
Subjects:
16-Androstene
16-Dehydropregnenolone
17-alpha-Hydroxypregnenolone - metabolism
17-hydroxy-pregnenolone
3α-hydroxy-5,16-pregnadien-20-one
3α-hydroxy-5α-androstan-17-one
3β,17-dihydroxy-5-pregnen-20-one
3β-hydroxy-5-androsten-17-one
3β-hydroxy-5-pregnen-20-one
3β-hydroxy-5α-androstan-17-one
4,16-androstadien-3-one
4-androstene-3,17-dione
5,16-androstadien-3β-ol
5α'-androst-16-en-3α-ol
5α'-androstane-3α,17α,-diol
5α-androst-16-en-3β-ol
an-α
an-β
Analytical, structural and metabolic biochemistry
andien-β
androstadienone
androstanediol
androstenedione
Androstenes - biosynthesis
androsterone
Animals
Biological and medical sciences
Chromatography, Gas
DHA (dehydroepiandrosterone)
epiandrosterone
Fundamental and applied biological sciences. Psychology
Gas chromatography-mass
Gas Chromatography-Mass Spectrometry
Male
Microsome
Microsomes - metabolism
Neonate
Other biological molecules
Porcine testis
pregnenolone
Pregnenolone - analogs & derivatives
Pregnenolone - isolation & purification
Pregnenolone - metabolism
spectrometry
Terpenes, steroids. Hormones
Testis - metabolism
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Summary:The biosynthesis of 16-androstenes has been studied in neonatal porcine testicular microsomes using 17-hydroxypregnenolone and 16-dehydropregnenolone, separately, as substrates. The metabolites formed after microsomal incubation with these substrates were purified, derivatized as O-methyloxime-trimethylsilyl ethers and analysed by capillary gas chromatography-mass spectrometry. In the incubation of 17-hydroxy-pregnenolone with microsomes, 16-dehydropregnenolone was identified as an intermediate in the biosynthesis of 16-androstenes. Further microsomal incubation of 16-dehydropregnenolone has established the intermediary role of this steroid in the production of 16-androstenes.
ISSN:0014-5793
1873-3468
DOI:10.1016/0014-5793(84)81099-6