The formation of 16,17-dihydroxylated C19 steroids from 10-dehydro C19 steroids in liver microsomes from male and female rats
Jan åke Gustafsson
The metabolism of the following substrates in liver microsomes from male and female rats was studied: 4,16-[7α-3H]androstadien-3-one, 5,16-androstadien-3β-ol, 5α-[7α-3H]androst-16-en-3α-ol, 5α-androst-16-en-3β-ol, 16α,17α-epoxy-5α-androstan3α-ol, 16α,17α-epoxy-5α-androstan-3β-ol and 3β-hydroxy-5,16-pregnadien-20-one. Liver microsomes from male rats were considerably more efficient in converting the 16-dehydro-C19-steroids than were liver microsomes from female rats. Male liver microsomes metabolized 4,16-androstadien-3-one, 5α-androst-16-en-3α-ol and 5α-androst-16-en-3β-ol into isomers of 5α-androstane-3,16β,17α-triol and 3,17β-dihydroxy-5α-androstan-16-one whereas female liver microsomes formed isomers of both 5α-androstane-3, 16α,17β-triol and 5α-androstane-3,16β,17α-triol from the same substrates. 5,16-Androstadien-3β-ol was metabolized into 5-androstene-3β,16β,17α-triol by liver microsomes from male rats ; liver microsomes from female rats did not form any 16,17-dioxygenated steroids from this substrate. No 16,17-dioxygenated metabolites were formed from 3β-hydroxy-5,16-pregnadien-2o-one, neither with microsomes from male rats, nor with microsomes from female rats. When 16α,17α-epoxy steroids were used as substrates both male and female liver microsomes formed 16β,17α-dihydroxylated metabolites. The large sexual differences characterizing the metabolism of 16-dehydro C19 steroids in liver microsomes from rats make the conversions described suitable assay systems for studying factors that regulate sexual differences in microsomal oxygenation reactions.
Biochimica et Biophysica Acta (BBA)/Lipids and Lipid Metabolism
https://doi.org/10.1016/0005-2760(73)90057-X
10.1016/0005-2760(73)90057-X
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C19-Steroid Chemistry 100%
Liver Microsomes Medicine & Life Sciences 69%
androst-16-en-3-ol Medicine & Life Sciences 62%
Steroid Chemistry 55%
androstane-3,16,17-triol Medicine & Life Sciences 49%
Pharmacological Metabolism Chemistry 46%
Steroids Medicine & Life Sciences 45%
Metabolite Chemistry 42%
Gustafsson, J. Å. (1973). The formation of 16,17-dihydroxylated C19 steroids from 10-dehydro C19 steroids in liver microsomes from male and female rats. Biochimica et Biophysica Acta (BBA)/Lipids and Lipid Metabolism, 296(1), 179-188. https://doi.org/10.1016/0005-2760(73)90057-X
The formation of 16,17-dihydroxylated C19 steroids from 10-dehydro C19 steroids in liver microsomes from male and female rats. / Gustafsson, Jan åke.
In: Biochimica et Biophysica Acta (BBA)/Lipids and Lipid Metabolism, Vol. 296, No. 1, 19.01.1973, p. 179-188.
Gustafsson, JÅ 1973, 'The formation of 16,17-dihydroxylated C19 steroids from 10-dehydro C19 steroids in liver microsomes from male and female rats', Biochimica et Biophysica Acta (BBA)/Lipids and Lipid Metabolism, vol. 296, no. 1, pp. 179-188. https://doi.org/10.1016/0005-2760(73)90057-X
Gustafsson JÅ. The formation of 16,17-dihydroxylated C19 steroids from 10-dehydro C19 steroids in liver microsomes from male and female rats. Biochimica et Biophysica Acta (BBA)/Lipids and Lipid Metabolism. 1973 Jan 19;296(1):179-188. https://doi.org/10.1016/0005-2760(73)90057-X
Gustafsson, Jan åke. / The formation of 16,17-dihydroxylated C19 steroids from 10-dehydro C19 steroids in liver microsomes from male and female rats. In: Biochimica et Biophysica Acta (BBA)/Lipids and Lipid Metabolism. 1973 ; Vol. 296, No. 1. pp. 179-188.
@article{a6649c6d552c4330adc44939a8107cb5,
title = "The formation of 16,17-dihydroxylated C19 steroids from 10-dehydro C19 steroids in liver microsomes from male and female rats",
abstract = "The metabolism of the following substrates in liver microsomes from male and female rats was studied: 4,16-[7α-3H]androstadien-3-one, 5,16-androstadien-3β-ol, 5α-[7α-3H]androst-16-en-3α-ol, 5α-androst-16-en-3β-ol, 16α,17α-epoxy-5α-androstan3α-ol, 16α,17α-epoxy-5α-androstan-3β-ol and 3β-hydroxy-5,16-pregnadien-20-one. Liver microsomes from male rats were considerably more efficient in converting the 16-dehydro-C19-steroids than were liver microsomes from female rats. Male liver microsomes metabolized 4,16-androstadien-3-one, 5α-androst-16-en-3α-ol and 5α-androst-16-en-3β-ol into isomers of 5α-androstane-3,16β,17α-triol and 3,17β-dihydroxy-5α-androstan-16-one whereas female liver microsomes formed isomers of both 5α-androstane-3, 16α,17β-triol and 5α-androstane-3,16β,17α-triol from the same substrates. 5,16-Androstadien-3β-ol was metabolized into 5-androstene-3β,16β,17α-triol by liver microsomes from male rats ; liver microsomes from female rats did not form any 16,17-dioxygenated steroids from this substrate. No 16,17-dioxygenated metabolites were formed from 3β-hydroxy-5,16-pregnadien-2o-one, neither with microsomes from male rats, nor with microsomes from female rats. When 16α,17α-epoxy steroids were used as substrates both male and female liver microsomes formed 16β,17α-dihydroxylated metabolites. The large sexual differences characterizing the metabolism of 16-dehydro C19 steroids in liver microsomes from rats make the conversions described suitable assay systems for studying factors that regulate sexual differences in microsomal oxygenation reactions.",
author = "Gustafsson, {Jan {\aa}ke}",
note = "Funding Information: The technical assistance of Miss Gunilla Ahnsater is gratefully acknowledged. This work was supported by a grant from the Swedish Medical Research Council (project No. 13X-2819), from Carl-Bertel Nathhorsts Vetcnskapliga Stiftelse and from Syskonen WessCns Stiftelse. Copyright: Copyright 2014 Elsevier B.V., All rights reserved.",
doi = "10.1016/0005-2760(73)90057-X",
journal = "Biochimica et Biophysica Acta - Lipids and Lipid Metabolism",
T1 - The formation of 16,17-dihydroxylated C19 steroids from 10-dehydro C19 steroids in liver microsomes from male and female rats
AU - Gustafsson, Jan åke
N1 - Funding Information: The technical assistance of Miss Gunilla Ahnsater is gratefully acknowledged. This work was supported by a grant from the Swedish Medical Research Council (project No. 13X-2819), from Carl-Bertel Nathhorsts Vetcnskapliga Stiftelse and from Syskonen WessCns Stiftelse. Copyright: Copyright 2014 Elsevier B.V., All rights reserved.
N2 - The metabolism of the following substrates in liver microsomes from male and female rats was studied: 4,16-[7α-3H]androstadien-3-one, 5,16-androstadien-3β-ol, 5α-[7α-3H]androst-16-en-3α-ol, 5α-androst-16-en-3β-ol, 16α,17α-epoxy-5α-androstan3α-ol, 16α,17α-epoxy-5α-androstan-3β-ol and 3β-hydroxy-5,16-pregnadien-20-one. Liver microsomes from male rats were considerably more efficient in converting the 16-dehydro-C19-steroids than were liver microsomes from female rats. Male liver microsomes metabolized 4,16-androstadien-3-one, 5α-androst-16-en-3α-ol and 5α-androst-16-en-3β-ol into isomers of 5α-androstane-3,16β,17α-triol and 3,17β-dihydroxy-5α-androstan-16-one whereas female liver microsomes formed isomers of both 5α-androstane-3, 16α,17β-triol and 5α-androstane-3,16β,17α-triol from the same substrates. 5,16-Androstadien-3β-ol was metabolized into 5-androstene-3β,16β,17α-triol by liver microsomes from male rats ; liver microsomes from female rats did not form any 16,17-dioxygenated steroids from this substrate. No 16,17-dioxygenated metabolites were formed from 3β-hydroxy-5,16-pregnadien-2o-one, neither with microsomes from male rats, nor with microsomes from female rats. When 16α,17α-epoxy steroids were used as substrates both male and female liver microsomes formed 16β,17α-dihydroxylated metabolites. The large sexual differences characterizing the metabolism of 16-dehydro C19 steroids in liver microsomes from rats make the conversions described suitable assay systems for studying factors that regulate sexual differences in microsomal oxygenation reactions.
AB - The metabolism of the following substrates in liver microsomes from male and female rats was studied: 4,16-[7α-3H]androstadien-3-one, 5,16-androstadien-3β-ol, 5α-[7α-3H]androst-16-en-3α-ol, 5α-androst-16-en-3β-ol, 16α,17α-epoxy-5α-androstan3α-ol, 16α,17α-epoxy-5α-androstan-3β-ol and 3β-hydroxy-5,16-pregnadien-20-one. Liver microsomes from male rats were considerably more efficient in converting the 16-dehydro-C19-steroids than were liver microsomes from female rats. Male liver microsomes metabolized 4,16-androstadien-3-one, 5α-androst-16-en-3α-ol and 5α-androst-16-en-3β-ol into isomers of 5α-androstane-3,16β,17α-triol and 3,17β-dihydroxy-5α-androstan-16-one whereas female liver microsomes formed isomers of both 5α-androstane-3, 16α,17β-triol and 5α-androstane-3,16β,17α-triol from the same substrates. 5,16-Androstadien-3β-ol was metabolized into 5-androstene-3β,16β,17α-triol by liver microsomes from male rats ; liver microsomes from female rats did not form any 16,17-dioxygenated steroids from this substrate. No 16,17-dioxygenated metabolites were formed from 3β-hydroxy-5,16-pregnadien-2o-one, neither with microsomes from male rats, nor with microsomes from female rats. When 16α,17α-epoxy steroids were used as substrates both male and female liver microsomes formed 16β,17α-dihydroxylated metabolites. The large sexual differences characterizing the metabolism of 16-dehydro C19 steroids in liver microsomes from rats make the conversions described suitable assay systems for studying factors that regulate sexual differences in microsomal oxygenation reactions.
U2 - 10.1016/0005-2760(73)90057-X
DO - 10.1016/0005-2760(73)90057-X
JO - Biochimica et Biophysica Acta - Lipids and Lipid Metabolism
JF - Biochimica et Biophysica Acta - Lipids and Lipid Metabolism