The biosynthesis of estriol-3,16-disulfate by guinea pig liver homogenate

doi:10.1016/0039-128X(74)90159-7

Steroids

Volume 23, Issue 2, February 1974, Pages 301-308

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Abstract

Incubation of ³H-estriol in guinea pig liver homogenate fortified with uridine-5′-diphosphoglucuronic acid afforded a new conjugate in addition to the expected ³H-estriol-3-glucosiduronate. Employing methodology including chromatography on alumina and Celite, high voltage paper electrophoresis and reverse isotope dilution, its structure was established as estriol-3-16-disulfate. The chemical synthesis and some of the physical properties of the disulfate are described.

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Cited by (7)

16-hydroxylation of estrogens in pigmented and albino guinea-pigs
1980, Journal of Steroid Biochemistry
Metabolites of injected [³H]-estrone-3-sulfate were investigated in urine, gall bladder bile, liver and kidney of mature pigmented and albino male and non-pregnant female guinea pigs (English Shorthair variety). Considerable formation of estriol, 16α-hydroxyestrone and 16β-hydroxyestrone disulfates, as well as estriol and 16α-hydroxyestrone monosulfates occurred in pigmented females. Monoglucuronides and monosulfates of estrone and estradiol-17β (estradiol) were also observed. No 16-hydroxysteroid monosulfates were detected in pigmented males but disulfates were present in urine, to a lesser extent than for females. No hydroxysteroid monosulfates were found in albinos of either sex and, although small amounts of a disulfate-like fraction occurred in urine, the steroid moieties were not identified. Pigmented females formed lesser amounts of hydroxysteroids from injected [³H]-estrone or estradiol than from estrone sulfate. These metabolites were not detected in the other animal groups. Qualitative patterns of estrone and estradiol monoglucuronides and monosulfates were similar in pigmented and albino animals, regardless of the precursor injected.
Biliary and urinary metabolites of estrone in the guinea pig
1978, Journal of Steroid Biochemistry
The biliary and urinary metabolites of [6,7-³H]-estrone in guinea pigs with biliary fistulas were analyzed. In the bile, estrone-3-glucosiduronate was a major metabolite; and estrone-3-sulfate and polar conjugates (probably, diglucosiduronates and disulfates) were minor metabolites. In the urine, estrone-3-glucosiduronate and 17β-estradiol-3-glucosiduronate were detected. Moreover, polar conjugates (probably diglucosiduronates) were also found, but estrone-3-sulfate could not be detected. The possibility exists that estrone-3-glucosiduronate is derived from the liver and is partly converted to 17β-estradiol-3-glucosiduronate extrahepatically.
The metabolism of estriol in the guinea-pig
1976, Journal of Steroid Biochemistry
Labeled estriol (E₃) was injected i.v. into intact guinea-pigs and animals with biliary fistulas. It was shown that biliary excretion constitutes a major route for the conjugates of E₃, probably followed by a significant enterohepatic circulation. The conjugation pattern of E₃ revealed the preponderant amount of the steroid to be excreted as a 3-glucosiduronate, both in the urine and bile. In contrast, the 3,16α-disulfate of E₃ was found in significant amount only in the bile. Unconjugated E₃ and its sulfate constituted a minor percentage of the radioactivity found both in bile and urine. The E₃ nucleus remained intact during the conjugation processes in the guinea-pig. The kidney was shown to glucoronidate E₃in vitro to some extent, but to a much lower degree than observed with kidneys of other species; sulfation of E₃ by the guinea-pig kidney was of an even much lower magnitude. Thus, we interpret the results to indicate that in guinea-pigs, the liver plays a paramount role in the conjugation of E₃ followed by biliary excretion of most of the conjugates and subsequent entero-hepatic circulation. The role of the kidney in the conjugation of E₃ in the guinea pig appears to be secondary to that of the liver.
16-Sulfates of estriol in body fluids of human pregnancy at term
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A method was developed for the assay of estriol-16-sulfate (E₃-16s) and estriol-3, 16-disulfate (E₃-3, 16-diS) in maternal serum, cord serum and amniotic fluid at delivery in human pregnancy, Tritiated E₃-16S and E₃-3, 16-diS are added to the fluid being analyzed. The conjugates are separated and purified by sequential chromatography on alumina, Celite and Sephadex LH-20. Each conjugate is hydrolyzed with Glusulase and the released estriol is quantified by radioimmunoassay. E₃-3, 16-diS was found in each fluid, most concentrated in the cord serum. Small amounts of E₃-16S were found in some amniotic fluids, and this conjugate was virtually absent from the sera. These new estriol conjugates comprise less than 1 percent of total estriol, apparently too low to be of diagnostic value in human pregnancy.
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The biosynthesis of estriol-3,16-disulfate by guinea pig liver homogenate

Abstract

Steroids

Steroids

Steroids

Acta Chem Scan.

J Clin Endocrinol Metab.