A CHROMATOGRAPHIC STUDY OF SOME CONVERSION PRODUCTS OF ESTRONE-16-C14IN THE URINE AND FECES OF THE LAYING HEN

1962 ◽  
Vol 40 (1) ◽  
pp. 123-135 ◽  
Author(s):  
L. Ainsworth ◽  
A. L. Carter ◽  
R. H. Common
Keyword(s):  
Enzymatic Hydrolysis ◽  
Urinary Metabolites ◽  
Laying Hen ◽  
Chromatographic Study ◽  
Borohydride Reduction ◽  
Acidic Hydrolysis ◽  
Sodium Borohydride Reduction ◽  
A Minor ◽  
Chromatographic Evidence ◽  
Unidentified Metabolite

Estrone-16-C14was administered intravenously to a laying hen. The urine excreted during the succeeding 24 hours contained, on the basis of chromatographic evidence, the following radioactive conversion products of estrone: estriol, 16-epiestriol, 17-epiestriol, 16-oxoestradiol-17 β, estradiol-17 β, and 16-oxoestrone. Three other minor conversion products were not identified. 16-Oxoestradiol and 16-oxoestrone were characterized more fully by chromatographic examination of their sodium borohydride reduction products.In a second experiment, urine and feces excreted during the first two 24-hour periods after administration of estrone-16-C14were examined separately for radioactive conversion products. Of the radioactivity injected, 24.5% was recovered in the estrogen-containing extracts of the excreta. The urinary extracts contained 69% of the recovered radioactivity and the fecal extracts contained 31%.In a third experiment, recoveries of urinary metabolites after enzymatic and after acidic hydrolysis were compared. The recovery after acidic hydrolysis was approximately two-thirds of that recovered after enzymatic hydrolysis. Most of this loss could be accounted for by destruction of 16-oxoestrone and a minor unidentified metabolite during acidic hydrolysis. The distribution of the conversion products on the urinary chromatogram confirmed the results of the previous experiments.None of the experiments gave any evidence for the presence of 2-methoxyestrone, estradiol-170α, equilin, or equilenin.

A CHROMATOGRAPHIC STUDY OF SOME CONVERSION PRODUCTS OF ESTRONE-16-C14IN THE URINE AND FECES OF THE LAYING HEN

1962 ◽  
Vol 40 (1) ◽  
pp. 123-135 ◽  
Author(s):  
L. Ainsworth ◽  
A. L. Carter ◽  
R. H. Common
Keyword(s):  
Enzymatic Hydrolysis ◽  
Urinary Metabolites ◽  
Laying Hen ◽  
Chromatographic Study ◽  
Borohydride Reduction ◽  
Acidic Hydrolysis ◽  
Sodium Borohydride Reduction ◽  
A Minor ◽  
Chromatographic Evidence ◽  
Unidentified Metabolite

Estrone-16-C14was administered intravenously to a laying hen. The urine excreted during the succeeding 24 hours contained, on the basis of chromatographic evidence, the following radioactive conversion products of estrone: estriol, 16-epiestriol, 17-epiestriol, 16-oxoestradiol-17 β, estradiol-17 β, and 16-oxoestrone. Three other minor conversion products were not identified. 16-Oxoestradiol and 16-oxoestrone were characterized more fully by chromatographic examination of their sodium borohydride reduction products.In a second experiment, urine and feces excreted during the first two 24-hour periods after administration of estrone-16-C14were examined separately for radioactive conversion products. Of the radioactivity injected, 24.5% was recovered in the estrogen-containing extracts of the excreta. The urinary extracts contained 69% of the recovered radioactivity and the fecal extracts contained 31%.In a third experiment, recoveries of urinary metabolites after enzymatic and after acidic hydrolysis were compared. The recovery after acidic hydrolysis was approximately two-thirds of that recovered after enzymatic hydrolysis. Most of this loss could be accounted for by destruction of 16-oxoestrone and a minor unidentified metabolite during acidic hydrolysis. The distribution of the conversion products on the urinary chromatogram confirmed the results of the previous experiments.None of the experiments gave any evidence for the presence of 2-methoxyestrone, estradiol-170α, equilin, or equilenin.

METABOLISM OF [4-14C]LYNESTRENOL IN MAN

1968 ◽  
Vol 42 (2) ◽  
pp. 337-343 ◽  
Author(s):  
SORAYA KAMYAB ◽  
K. FOTHERBY ◽  
A. I. KLOPPER
Keyword(s):  
Phenolic Compounds ◽  
Enzymatic Hydrolysis ◽  
Half Life ◽  
Human Subjects ◽  
Free Fraction ◽  
Urinary Metabolites ◽  
Polar Compounds ◽  
Mean Value ◽  
Biological Half Life ◽  
Chromatographic Evidence

SUMMARY After the administration of [4-14C]lynestrenol (17α-ethynyl-19-nor-androst-4-en-17β-ol) to 7 human subjects 31·–57·6% of the dose, whether administered orally or i.v., was excreted in the urine within 5 days. The biological half-life of radioactivity was 26·5 hr. After acid and enzymatic hydrolysis, 58·7 and 45·6% respectively of the urinary radioactivity was extractable. About 10% of the urinary metabolites were excreted as sulphate conjugates. A mean value of 1·75% of the administered dose was converted to phenolic compounds. The metabolites in the free fraction and enzymehydrolysed extract of urine were almost entirely polar compounds, whereas 70% of the metabolites in the sulphate fraction were much less polar. The chromatographic evidence showed that hydroxylation of lynestrenol must have occurred at two points in the molecule. Plasma radioactivity decreased more rapidly than after administration of norethisterone.

Flavan derivatives. XXXIII. 2-Methoxyflavan-3,4-dione and 2-Methoxyflavan-3,4-diol derivatives

1972 ◽  
Vol 25 (4) ◽  
pp. 857 ◽  
Author(s):  
JW Clark-Lewis ◽  
I Dainis ◽  
EJ McGarry ◽  
MI Baig
Keyword(s):  
Sodium Borohydride ◽  
Catalytic Hydrogenation ◽  
Room Temperature ◽  
Periodic Acid ◽  
Metal Hydrides ◽  
Borohydride Reduction ◽  
Complex Metal ◽  
Sodium Borohydride Reduction ◽  
A Minor ◽  
Minor Quantity

Sodium borohydride reduction of 3-hydroxy-7-benzyloxy-2,3,4'-trimethoxy-flavanone and of 3-hydroxy-2,3,7,4'-tetramethoxyflavanone is shown to yield mainly trans-trans-2-methoxyflavan-3,4-dials, a novel class of flavan derivatives. The 7-benzyloxy hemiacetal also gave a minor quantity of the cis-cis-2-methoxyflavan-3,4-dial and less of the corresponding 2,3-cis-flavan-3,4-trans-dial. Catalytic hydrogenation over palladium, or reduction with complex metal hydrides at room temperature or above, converted the hemiacetals into the flavonols from which they were originally prepared by oxidation with periodic acid in methanol.

A METHOD FOR THE ANALYSIS OF URINARY 17-HYDROXYCORTICOSTEROIDS

1961 ◽  
Vol 22 (1) ◽  
pp. 31-46 ◽  
Author(s):  
J. D. FEW
Keyword(s):  
Sodium Borohydride ◽  
Alkaline Hydrolysis ◽  
Sodium Periodate ◽  
Periodate Oxidation ◽  
Urinary Metabolites ◽  
Partition Chromatography ◽  
Borohydride Reduction ◽  
Urinary Steroids ◽  
Sodium Borohydride Reduction

SUMMARY A method for the analysis of urinary 17-hydroxycorticosteroids is described. The urinary steroids are submitted, in situ, to sodium borohydride reduction, sodium periodate oxidation and mild alkaline hydrolysis. The generated 17-ketosteroids are separated by partition chromatography into 11-deoxy and 11-oxy fractions which are separately estimated by the Zimmermann reaction. By this method it is possible to estimate the urinary metabolites of cortisol without interference by corticosteroids not oxygenated at C-11.

Metabolic Studies of Vitamin K1-14C and Menadione-14C in the Normal and Hepatectomized Rats

1968 ◽  
Vol 19 (03/04) ◽  
pp. 383-388 ◽  
Author(s):  
R Losito ◽  
C. A Owen ◽  
E. V Flock ◽  
Keyword(s):  
Enzymatic Hydrolysis ◽  
Oral Anticoagulants ◽  
Urinary Metabolites ◽  
The Other ◽  
Vitamin K1 ◽  
Vitamin K3 ◽  
Metabolic Studies ◽  
Intact Rats

SummaryThe metabolism of vitamin K1- 14C and menadione-14C (vitamin K3-14C) was studied in normal and hepateetomized rats. After the administration of menadione, about 70% of the 14C was excreted in the urine in 24 hrs in both types of rats. Two urinary metabolites were identified by enzymatic hydrolysis: one a glucuronide and the other a sulfate of reduced menadione. Thus, the liver is not necessary for the metabolism of menadione. In the vitamin K1 studies, the intact rats excreted only 10% of the 14C and the hepatectomized rats excreted less than 0.5%. The retention of vitamin K1 may explain its superiority over menadione as an antidote for overdosages of oral anticoagulants.

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