Origin of 5α‐pregnane‐3α,20α,21‐triol 3‐sulphate in pregnant women

Baillie, Thomas A.; Sjövall, Jan; Sjövall, K.

doi:10.1016/0014-5793(75)80438-8

Cited by 7 publications

(1 citation statement)

References 23 publications

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“…The difficulty in analyzing feces explains why less attention has been paid to metabolites with a 5α than a 5β configuration. Among the interesting metabolic reactions of the sulfated 5α-pregnane derivatives were 16α-hydroxylation of the intact pregnanolone sulfates and 21-hydroxylation specific for the 3α-hydroxy-5α-pregnan-20-one/5α-pregnan-3α,20α-diol 3-sulfate couple to yield 5α-pregnan-3α,20α,21triol 3-sulfate (120,122). The latter reaction was the exclusive pathway to this pregnanetriol sulfate, which together with its disulfate and the pregnanediol isomer disulfates constituted end products in the metabolism.…”

Section: Steroid Sulfates In Pregnancy and Intrahepatic Cholestasis Omentioning

confidence: 99%

Fifty years with bile acids and steroids in health and disease

Sjövall

2004

Lipids

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Cholesterol and its metabolites, e.g., steroid hormones and bile acids, constitute a class of compounds of great biological importance. Their chemistry, biochemistry, and regulation in the body have been intensely studied for more than two centuries. The author has studied aspects of the biochemistry and clinical chemistry of steroids and bile acids for more than 50 years, and this paper, which is an extended version of the Schroepfer Medal Award lecture, reviews and discusses part of this work. Development and application of analytical methods based on chromatography and mass spectrometry (MS) have been a central part of many projects, aiming at detailed characterization and quantification of metabolic profiles of steroids and bile acids under different conditions. In present terminology, much of the work may be termed steroidomics and cholanoidomics. Topics discussed are bile acids in human bile and feces, bile acid production, bacterial dehydroxylation of bile acids and steroids during the enterohepatic circulation, profiles of steroid sulfates in plasma of humans and other primates, development of neutral and ion-exchanging lipophilic derivatives of Sephadex for sample preparation and group separation of steroid and bile acid conjugates, profiles of steroids and bile acids in human urine under different conditions, hydroxylation of bile acids in liver disease, effects of alcohol-induced redox changes on steroid synthesis and metabolism, alcohol-induced changes of bile acid biosynthesis, compartmentation of bile acid synthesis studied with 3H-labeled ethanol, formation and metabolism of sulfated metabolites of progesterone in human pregnancy, abnormal patterns of these in patients with intrahepatic cholestasis of pregnancy corrected by ursodeoxycholic acid, inherited and acquired defects of bile acid biosynthesis and their treatment, conjugation of bile acids and steroids with N-acetylglucosamine, sulfate-glucuronide double conjugates of hydroxycholesterols, extrahepatic 7alpha-hydroxylation and 3-dehydrogenation of hydroxycholesterols, and extrahepatic formation of C27 bile acids. The final part discusses analysis of free and sulfated steroids in brain tissue by capillary liquid chromatography-electrospray MS and suggests a need for reevaluation of the function of steroid sulfates in rat brain.

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Section: Steroid Sulfates In Pregnancy and Intrahepatic Cholestasis Omentioning

confidence: 99%

Fifty years with bile acids and steroids in health and disease

Sjövall

2004

Lipids

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A selected bibliography of biomedical and environmental applications of stable isotopes. I—Deuterium 1971-1976

Klein

1978

Biol. Mass Spectrom.

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Synthesis of deuterium labeled cholesterol and steroids and their use for metabolic studies

Goad

Breen

Rendell

et al. 1982

Lipids

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A simple method is described for the preparation of [6,7,7(-2)H3] sterols and steroids. The synthesis starts with a Δ(5)-sterol or steroid and involves preparation of the 6-oxo-3α,5α-cyclosteroid, base exchange in the presence of deuterium oxide to introduce two deuteriums at the C-7 position and sodium borodeuteride reduction of the 6-oxo group to introduce the third deuterium atom at C-6. Rearrangement of the [6,7,7(-2)H3]6α-hydroxy-3α,5α-cyclosteroid then gives the desired [6,7,7(-2)H3]-Δ(5) sterol or steroid. [6,7,7(-2)H3]Cholesterol, [6,7,7(-2)H3]pregnenolone and [6,7,7(-2)H3]3β-hydroxyandrost-5-en-17-one were synthesized in this fashion and [6,7,7(-2)H3]progesterone was prepared from the [6,7,7(-2)H3]pregnenolone. Three examples of the use of these deuchromatography-mass spectrometry. The chrysophyte alga,Ochromonas malhamensis, was shown to be capable of introducing an extra methyl or ethyl group at C-24 of the side chain of [6,7,7(-2)H3]cholesterol to yield brassicasterol and poriferasterol, respectively. The ovary of the echinoderm,Asterias rubens, was demonstrated to metabolize [6,7,7(-2)H3]progesterone to yield mainly the 5α-isomers of pregnane-3,20-dione and 3β-hydroxypregnan-20-one. However, the 5β-isomers of these compounds were also detected as minor products for the first time as progesterone metabolites in this animal. Isolated oocytes of the frog,Xenopus laevis, produced a number of metabolites of [6,7,7(-2)H3]progesterone. In this report, two of them were shown to be 17α-hydroxy-pregn-4-en-3,20-dione and 20α-hydroxypregn-4-en-3-one.

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Origin of 5α‐pregnane‐3α,20α,21‐triol 3‐sulphate in pregnant women

Cited by 7 publications

References 23 publications

Fifty years with bile acids and steroids in health and disease

Fifty years with bile acids and steroids in health and disease

A selected bibliography of biomedical and environmental applications of stable isotopes. I—Deuterium 1971-1976

Synthesis of deuterium labeled cholesterol and steroids and their use for metabolic studies

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