Isolation of tetrahydroaldosterone 3β-glucosiduronic acid from urine

Alvarez, Marcos N; Carpenter, Paul C.; Mattox, Vernon R.

doi:10.1016/0022-4731(76)90062-5

Cited by 7 publications

(2 citation statements)

References 12 publications

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“…Patients with low renin hypertension also preferentially metabolize aldosterone to 3,5-tetrahydroaldosterone [96]. A radioimmunoassay was designed using an antibody against 3,5-tetrahydroaldosterone-glucuronide isolated from the urine which allowed its direct measurement in urine [97,98]. This simplified the assay but unfortunately, the antibody and standards are no longer available.…”

Section: Tetrahydroaldosteronementioning

confidence: 99%

An Abbreviated History of Aldosterone Metabolism, Current and Future Challenges

Gómez-Sánchez

2023

Exp Clin Endocrinol Diabetes

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The initial isolation of adrenal steroids from large quantities of animal adrenals resulted in an amorphous fraction resistant to crystallization and identification that had potent effects on electrolyte transport. Aldosterone was eventually isolated and identified in the fraction and was soon shown to cause hypertension when in excess. The autonomous and excessive production of aldosterone, primary aldosteronism, is the most common cause of secondary hypertension. Aldosterone is metabolized in the liver and kidney and its metabolites conjugated with glucuronic acid for excretion. The most common liver metabolite is 3,5-tetrahydroaldosterone-3-glucuronide; that of the kidney is aldosterone-18-oxo-glucuronide. Their values, especially the aldosterone-18-oxo-glucuronide, are commonly used for the diagnosis of primary aldosteronism because they provide and integrated value of the total daily production of aldosterone. Conversion of aldosterone to 18-oxo-glucuronide is impeded by drugs, like some common NSAIDS that compete for UGT2B7, the most important glucuronosyltransferase for aldosterone metabolism. Tetrahydroaldosterone is the most abundant metabolite and most reliable for the diagnosis of primary aldosteronism, but is not commonly measured.

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Section: Tetrahydroaldosteronementioning

confidence: 99%

An Abbreviated History of Aldosterone Metabolism, Current and Future Challenges

Gómez-Sánchez

2023

Exp Clin Endocrinol Diabetes

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“…The ethanolic eluate was evaporated and the residue was chromatographed on a column (Scmx 35 cm) by using system E. Material eluted at 4.4 VO contained the acid-labile conjugate and was combined and evaporated after addition of lO,ug disodium EDTA. [The material eluted at 8.8 VO contained the glucosiduronate of tetrahydroaldosterone (Alvarez et al, 1976)]. The acid-labile conjugate was then chromatographed by reverse-phase technique (systemP) on a column (2.5 cm x 42cm) with Aliquat as ion exchanger and aq.…”

Section: Yield (%)mentioning

confidence: 99%

Isolation, determination of structure and synthesis of the acid-labile conjugate of aldosterone

Carpenter¹,

Mattox²

1976

Biochemical Journal

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1. After administration of 600mg of 3H-labelled aldosterone to human volunteers, 57 mg of homogeneous acid-labile conjugate was isolated from the urine and identified as aldosterone 18 beta-D-glucosiduronic acid. 2. Esterification and acetylation of the conjugate gave a tetra-acetate methyl ester, which, by measurement of the optical rotation and nuclear-magnetic-resonance spectrum, was shown to be a beta-glucosiduronate. This tetra-acetate methyl ester was synthesized in approx. 10% yield by the Koenigs-Knorr procedure. 3. Removal of the acetyl and methyl ester groups from the tetra-acetate methyl ester with alkali was accompanied by almost complete isomerization at C-17 to give 17-isoaldosterone 18 beta-D-glucosiduronic acid. 4. To prevent inversion at C-17 during removal of the acetate and ester groups of beta-glucosiduronate (a) the 3,20-disemicarbazone was prepared, (b) the acetate and ester groups were removed from the disemicarbazone by treatment with alkali, and (c) the semicarbazone groups were removed from the product at pH 2.0, and aldosterone 18 beta-D-glucosiduronic acid was obtained in 47% overall yield. 5. In the presence of components used to synthesize beta-glucosiduronate by the Koenigs-Knorr reaction this substance is converted slowly into the alpha-glucosiduronate; this conversion is responsible, in part, for the low yield of beta-glucosiduronate. 6. Two additional conjugates were obtained in the Koenigs-Knorr reaction; a provisional structure was assigned to one substrate. The other substance is a C-18 alpha-glucosiduronate. Removal of the acetyl and ester groups from C-18 alpha-glucosiduronate gave the alpha-glucosiduronic acid in 84% yield and the 17-isoaldosterone alpha-glucosiduronic acid in 12% yield. 7. The rate at which several types of beta-glucuronidase hydrolyse the foregoing steroidal alpha- and beta-glucosiduronic acids is given.

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A radioimmunoassay for the measurement of tetrahydroaldosterone 3-glucosiduronic acid in human plasma

Jowett¹,

Slater²

1981

Clinica Chimica Acta

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Isolation of tetrahydroaldosterone 3β-glucosiduronic acid from urine

Cited by 7 publications

References 12 publications

An Abbreviated History of Aldosterone Metabolism, Current and Future Challenges

An Abbreviated History of Aldosterone Metabolism, Current and Future Challenges

Isolation, determination of structure and synthesis of the acid-labile conjugate of aldosterone

A radioimmunoassay for the measurement of tetrahydroaldosterone 3-glucosiduronic acid in human plasma

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