Isolation of 17α-estradiol 17-β-D-glucopyranoside from rabbit urine, and its synthesis and characterization

Dg, Williamson; Dc, Collins; Ds, Layne; Rb, Conrow; Bernstein, Seymour

doi:10.1021/bi00839a012

Cited by 33 publications

(10 citation statements)

References 17 publications

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“…Disaccharidic bilirubin conjugates containing hexuronic acid residues, aldobiuronic acid or pseudoaldobiuronic acid (Kuenzle, 1970c) have been demonstrated by means of their phenylazo derivatives. Mixed conjugates of steroids containing glucuronic acid and either glucopyranose (Williamson, Collins, Layne, Conrow & Bernstein, 1969; or N-acetylglucosamine (Layne, Sheth & Kirdani, 1964;Layne, 1965;Arcos & Lieberman, 1967;Collins, Williams & Layne, 1967;) have also been described. The glycosidic linkages of the steroid conjugates were shown to be in the :-D configuration (Collins et al 1967;Williamson et al 1969;Matsui & Fukushima, 1969).…”

Section: Discussionmentioning

confidence: 99%

Excretion in dog bile of glucose and xylose conjugates of bilirubin

Fevery

Hees

Leroy

et al. 1971

Biochemical Journal

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1. T.l.c. with neutral solvent systems of ethyl anthranilate azopigments derived from bile of man, dog and rat revealed pronounced species variation. The less polar components (alpha-group) could be separated conveniently by development with chloroform-methanol (17:3, v/v). 2. The azopigment material derived from gallbladder bile of dog contained about 10% of azobilirubin beta-d-monoxyloside (azopigment alpha(2)) and 30% of azobilirubin beta-d-monoglucoside (azopigment alpha(3)). The sugar moieties were identified by t.l.c. with acidic, neutral and basic solvent systems and by anion-exchange column chromatography of their boric acid complexes. Treatment of the purified azopigments with ammonia vapour led to the formation of the amide of azobilirubin, indicating that both pigments are ester glycosides. The beta-d configuration was demonstrated by enzymic studies with emulsin (an adequate source of beta-glucosidase activity) and with Mylase-P (an adequate source of beta-glucosidase and beta-xylosidase activities). 3. Hydrolysis studies with model substrates and with the alpha(2)- and alpha(3)-azopigments suggested that in Mylase-P the beta-glucosidase and beta-xylosidase activities reside in separate enzymes. 4. Compared with the accepted conjugation with glucuronic acid as a major route of detoxication in mammals, the detection of large amounts of xylose and glucose conjugates of bilirubin in dog bile suggests that the underlying biosynthetic pathways may be important alternative routes of detoxication.

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Section: Discussionmentioning

confidence: 99%

Excretion in dog bile of glucose and xylose conjugates of bilirubin

Fevery

Hees

Leroy

et al. 1971

Biochemical Journal

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“…The transfer of glucose from UDBglucose to phenolic and alcoholic groups on steroids can be accomplished by preparations of mammalian microsonmes (1,2). The study of the formation of steroid glucosides by liver tissue from several animals has revealed interesting comparative differences in the specificity of glucosyl transfer to various hydroxyl groups, and in the requirement for conjugation of one hydroxyl of the steroid with glucuronie acid, prior to the addition of glucose to a second hydroxyl.…”

Section: Introductionmentioning

confidence: 99%

The Transfer of Glucose to Steroids by Chimpanzee Liver Microsomes

Labow¹,

Williamson²,

Layne³

et al. 1975

Can. J. Biochem.

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Microsomal preparations from chimpanzee liver can transfer glucose from UDPglucose to the 17alpha-hydroxyl group of 17alpha-estradiol and of 17alpha-estradiol-3-glucuronide. A phenolic glucoside of estrone, but not of either 17alpha- or 17beta-estradiol is also formed. No formation of glucosides of p-nitrophenol, or of diethylstilbestrol was demonstrated. The specificity of glucosyl transfer in the chimpanzee is not identical to that in either the human, the rabbit, or the sheep.

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“…All samples for assays (except microsomal preparations) were reconstituted for 10 min at 40C with sonicated dispersions of 50 ,g of egg yolk L-a-phosphatidylcholine per assay mixture prepared as described elsewhere (7 When the purified radioactive reaction product was treated either with bovine liver ,3-glucuronidase as described previously for the hydrolysis of bile acid glucuronides (8) or with a-glucosidase at 100 units/ml in 50 mM potassium phosphate, pH 6.0, for 5 hr at 25°C no cleavage of the reaction product was observed after analysis by TLC. For identification of the glucose moiety the purified reaction product was subjected to mild acid hydrolysis as described by Williamson et al (11). After extraction with chloroform the aqueous phase was evaporated to dryness and the residue was taken up in ethanol/water (7:3, vol/vol) and examined on silica gel 60 plates in 1-propanol/water (7:1, vol/vol) (12) Other analytical methods.…”

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confidence: 99%

“…Protein concentrations were determined as described previously (7). Due to interference of octyl glucoside and Zwittergent [3][4][5][6][7][8][9][10][11][12] in concentrations greater than 0.1% with the protein assay the protein content from dilute solutions (<5 ,ug/ml) was estimated after quantitative precipitation as described by Polacheck and Cabib (13) with the following modifications: The dissolved precipitate was neutralized with 0.5 M HCl, after which protein was Biochemistry: Matern et aL measured as described elsewhere (7).…”

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confidence: 99%

Formation of bile acid glucosides by a sugar nucleotide-independent glucosyltransferase isolated from human liver microsomes.

Matern¹,

Matern²,

Gerok³

1984

Proc. Natl. Acad. Sci. U.S.A.

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A heat-labile protein has been detected in microsomes from human liver which catalyzes the formation of glucosides of the bile acids chenodeoxycholic, deoxycholic, and ursodeoxycholic acids. This glucosyltransferase activity has been purified about 900-fold from human liver microsomes, resulting in homogeneity as determined by sodium dodecyl sulfate gel electrophoresis. The subunit molecular weight was calculated to be about 56,000. The catalyzed by a sugar nucleotide-independent glucosyltransferase and is therefore distinct from the known mechanisms of glycoside conjugation.

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Isolation of 17α-estradiol 17-β-D-glucopyranoside from rabbit urine, and its synthesis and characterization

Cited by 33 publications

References 17 publications

Excretion in dog bile of glucose and xylose conjugates of bilirubin

Excretion in dog bile of glucose and xylose conjugates of bilirubin

The Transfer of Glucose to Steroids by Chimpanzee Liver Microsomes

Formation of bile acid glucosides by a sugar nucleotide-independent glucosyltransferase isolated from human liver microsomes.

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