Effect of side chain length on biotransformation, hepatic transport, and choleretic properties of chenodeoxycholyl homologues in the rodent: Studies with dinorchenodeoxycholic acid, norchenodeoxycholic acid, and chenodeoxycholic acid

Hepatology

Volumn 26, Issue 2, 1997, Pages 374-385

  Yeh, Hong Zen ^a,b   Schteingart, Claudio D ^a,c   Hagey, R Lee ^a,d   Ton Nu, Huong Thu ^e   Bolder, Ulrich ^f   Gavrilkina, Miriam A ^g   Steinbach, Joseph H ^a   Hofmann, Alan F ^a,h  

^a UNIVERSITY OF CALIFORNIA SAN DIEGO   (United States)

^b TAICHUNG VETERANS GENERAL HOSPITAL   (Taiwan)

^c Ferring Pharmaceuticals AS   (Denmark)

^d ZOOLOGICAL SOCIETY OF SAN DIEGO   (United States)

^e La Jolla Pharmaceutical Company   (United States)

^f UNIVERSITY OF REGENSBURG   (Germany)

^g Inst for Rehabilitative Medicine   (Ukraine)

^h UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CHENODEOXYCHOLIC ACID;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ARTICLE; BILE ACID SYNTHESIS; BILE FLOW; BILE SECRETION; BIOTRANSFORMATION; GLUCURONIDATION; HAMSTER; MALE; NONHUMAN; PRIORITY JOURNAL; RAT;

ANIMALS; BILIARY FISTULA; BIOLOGICAL TRANSPORT; BIOTRANSFORMATION; CHENODEOXYCHOLIC ACID; CHOLAGOGUES AND CHOLERETICS; CRICETINAE; LIVER; RATS; SOLUBILITY; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 0030806732     PISSN: 02709139     EISSN: None     Source Type: Journal    
DOI: 10.1002/hep.510260218     Document Type: Article

References (17)

1. Schteingart CD, Hofmann AF. Synthesis of 24-nor-5β -cholan-23-oic acid derivatives: a convenient and efficient one-carbon degradation of the side chain of natural bile acids. J Lipid Res 1988; 29:1387-1395.
2. O'Maille ER, Kozmary SV, Hofmann AF, Gurantz D. Different effects of norcholate and cholate on bile flow and biliary lipid secretion in the rat. Am J Physiol 1984; 246:G67-G71.
3. Yoon YB, Hagey LR, Hofmann AF, Gurantz D, Michelotti EL, Steinbach JH. Effect of side-chain shortening on the physiologic properties of bile acids: hepatic transport and effect on biliary secretion of 23-norursodeoxycholate in rodents. Gastroenterology 1986; 90:837-852.
4. Palmer KR, Gurantz D, Hofmann AF, Clayton LM, Hagey LR, Cecchetti S. Hypercholeresis induced by norchenodeoxycholate in biliary fistula rodent. Am J Physiol 1987; 252:G219-G228.
5. Gurantz D, Schteingart CD, Hagey LR, Steinbach JH, Grotmol T, Hofmann AF. Hypercholeresis induced by unconjugated bile acid infusion correlates with recovery in bile of unconjugated bile acids. HEPATOLOGY 1991; 13:540-550.
6. Clayton LM, Gurantz D, Hofmann AF, Hagey LR, Schteingart CD. Role of bile acid conjugation in hepatic transport of dihydroxy bile acids. J Pharmacol Exp Ther 1989; 248:1130-1137.
7. Lindstedt S, Tryding N. On the metabolism of bishomocholic, homocholic, and norcholic acid in the rat. Arkh Kemi 1957; 11:137-144.
8. Vessey DA, Whitney J, Gollan JL. The role of conjugation reactions in enhancing biliary secretion of bile acids. Biochem J 1983; 214:923-927.
9. Nakatomi F, Kihira K, Kuramoto T, Hoshita T. Intestinal absorption and metabolism of norcholic acid in rats. J Pharmacobiodyn 1985; 8: 557-563.
10. Roda A, Hofmann AF, Mysels KJ. The influence of bile salt structure on self-association in aqueous solutions. J Biol Chem 1983; 258:6362-6370.
11. Kirkpatrick RB, Green MD, Hagey LR, Hofmann AF, Tephly TR. Effect of side chain length on bile acid conjugation: glucuronidation, sulfation and Coenzyme A formation of nor-bile acids and their natural C24 homologs by human and rat liver fractions. HEPATOLOGY 1988; 8:353-357.
12. Hofmann AF. The cholehepatic circulation of unconjugated bile acids: an update. In: Paumgartner G, Stiehl A, Gerok W, eds. Bile acids and the hepatobiliary system. Boston: Kluwer, 1993:143-160.
13. Kuipers F, Havinga R, Bosschieter H, Toorop GP, Hindriks FR, Vonk RJ. Enterohepatic circulation in the rat. Gastroenterology 1985; 88:403-411.
14. Huffman JW, Sobti RR. Synthetic approaches to steroidal alkaloids II (1). Preparation and reactions of 12-oxo-dinorcholanic acids. Steroids 1970; 16:755-770.
15. Carlson GL, Belobaba DTE, Hofmann AF, Wedmid Y. 24-nor-5β -chol-22-enes derived from the major bile acids by oxidative decarboxylation. Steroids 1977; 30:787-793.
16. Del Vecchio S, Ostrow JD, Mukerjee P, Ton-Nu HT, Schteingart CD, Hofmann AF, Cerrè C, Roda A. A method for the removal of surface active impurities and calcium from conjugated bile salt preparations: comparison with silicic acid chromatography. J Lipid Res 1995; 36:2639-2650.
17. Rossi SS, Converse JL, Hofmann AF. High pressure liquid Chromatographic analysis of conjugated bile acids in human bile: simultaneous resolution of sulfated and unsulfated lithocholyl amidates and the common conjugated bile acids. J Lipid Res 1987; 28:589-595.