Glycolithocholic acid

Table 5.4.6 Serum BA composition in healthy subjects (1,2), in a patient (3) with primary biliary cirrhosis (PBC) before (A) and after (B) treatment with ampicillin and in a patient (4) with PBC before (A) and after (B) treatment with UDCA. Results are expressed in nmol/ml. RDS% of three measurements was in the range 3.1-7.5%. - Means -detectable value (adapted from [20]). GCA glycocholic acid, GDCA glycodeoxycholic acid, GCDCA glycochenodeoxycholic acid, GLCA glycolithocholic acid,...

Palmer (133) has isolated labeled glycolithocholic acid 3-sulfate and taurolithocholic acid 3-sulfate from human bile after oral administration of labeled lithocholic acid. No further information concerning sulfate esters of bile acids is available at present. 

Fig. 3 The densitograms of bile acids investigated (C, cholic acid GC, glycocholic acid GLC, glycolithocholic acid DC, deoxycholic acid CDC, chenodeoxycholic acid GDC, glyco-deoxycholic acid LC, lithocholic acid) at wavelengths 380, 400, 420, 440, and 460 nm after their separation using a n-hex-ane-ethyl acetate-methanol-acetic acid, 20 20 5 2 (v/v/v/v) as mobile phase and after the application of sulfuric acid in methanol (1 19, v/v the plate was immersed in dipping the solution of sulfuric acid for 15 sec, and it was then heated to 90°C for 20 min) as visualizing reagent.

Prepare 100 ng/(J.l solutions of taurocholic acid, glycocholic acid, taurocheno-deoxycholic acid, taurodeoxycholic acid, glycochenodeoxycholic acid, glyco-deoxycholic acid, and glycolithocholic acid (Sigma) in methanol. 

A cytosolic sulfotransferase has been identified in rat liver and kidney which utilizes 3 -phosphoadenosine-5 -phosphosulfate (PAPS) and shows a greater rate of sulfation for glycolithocholate than lithocholate. In an assay with the enzyme preparation, PAPS, and conjugated bile acids, 3 unidentified products were formed from taurocholate suggesting multiple sulfation of more polar conjugated bile acids [64]. The enzyme from liver, proximal intestine or adrenals of hamster produced only glycochenodeoxycholate 7-sulfate. Comparable results with the enzyme from kidney will be discussed in Section VI.3. Hepatic enzyme from the female hamster shows 4-fold greater activity than that of the male [65]. 

Fig. 8. Glycocholic acid (XIII) taurocholic acid (XIV) glycolithocholic sulfate (XV) taurolithocholic sulfate (XVI).

Chemically, the bile acids are hydroxylated derivatives of cholanic acid, a tetracyclic steroid acid of 24 carbon atoms. The acids occur in nature largely as the water-soluble sodium salts of peptide conjugates of glycine and taurine. The free acids are liberated by saponification or specific enzyme hydrolysis. The chemistry of the bile acids has been reviewed in Chapter 1 of this volume (1). In view of their highly polar nature, special attention is called to the recent discovery of the cholic acid conjugates of ornithine (2, 3) and the 3a-sulfate esters of glycolithocholic and taurolithocholic acids (4). 

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