Isolation From Urine and Synthesis of Tetrahydrocortisone Glucuronoside

Adrenocortical Steroids in the Peripheral Blood of Man*

“…The corticosteroids occur in urine almost entirely in a reduced state, conjugated as glucuronosides. These conjugates have been isolated from urine (22). On the other hand, in blood, about 50 per cent of the total quantity we have measured is free and retains the structure of the active substances secreted by the adrenal gland.…”

On the Rate of Formation of Steroidal Glucuronosides in Patients with Familial and Acquired Jaundice*

“…3 We express our gratitude to Dr. Karl Pfister of Merck and Co., Rahway, N. J., for the generous supply of tetrahydrocortisone, tetrahydrocortisol, and cortisol. 4 Mr. Otto Gonzales kindly carried out the analyses in the laboratory of Dr. Seymour Lieberman. Rate of disappearance of steroids from plasma.…”

“…Reduction of the C-20 ketone group to a hydroxyl leads to further increase in polarity (3). Once formed, these reduced compounds are rendered still more water-soluble by conjugation at the three position with glucuronic acid (1,4). The formation of such glucuronosides also results in a lesser degree of binding to plasma proteins (5,6).…”

The glycosylation of steroids

“…The same procedure was applied in 1955 by Schneider et al to the synthesis of methyl (21-acetoxy-11,20-dioxo17a-hydroxy-5b-pregnan-3a-yl-2,3,4-tri-O-acetyl-b-Dglucosid)-uronate. 12 The most popular catalyst used for the glycosylation of steroids, silver carbonate, was involved in the first glycosylation of estrone with methyl 2,3,4-tri-O-acetyl1a-bromo-1-deoxy-D-glucopyranuronate in the presence of calcium sulphate (Scheme 2). 13 In 1947, Elderfield et al prepared the first glucosides of digitoxigenin and digoxigenin which have been widely involved in glycosylation.…”