A new, major C27 biliary bile acid in the Red-winged tinamou (Rhynchotus rufescens): (25R)-1β,3α, 7α-trihydroxy-5β-cholestan-27-oic acid

Journal of Lipid Research

Volumn 50, Issue 4, 2009, Pages 651-657

  Hagey, Lee R ^a   Kakiyama, Genta ^b   Muto, Akina ^b   Iida, Takashi ^b   Mushiake, Kumiko ^c   Goto, Takaaki ^c   Mano, Nariyasu ^d   Goto, Junichi ^d   Oliveira, Cleida A ^e   Hofmann, Alan F ^a  

^a UNIVERSITY OF CALIFORNIA SAN DIEGO   (United States)

^b NIHON UNIVERSITY   (Japan)

^c TOHOKU UNIVERSITY   (Japan)

^d TOHOKU UNIVERSITY HOSPITAL   (Japan)

^e FEDERAL UNIVERSITY OF MINAS GERAIS   (Brazil)

Author keywords

1 ,3 ,7 trihydroxy 5 cholestan 27 oic acid; 1 hydroxylation; C27 bile acids; LC MS; NMR; taurine conjugate

Indexed keywords

1 BETA , 3ALPHA, 7ALPHA TRIHYDROXY 5BETA CHOLESTAN 27 OIC ACID; 3ALPHA, 7ALPHA, 12ALPHA TRIHYDROXY 5BETA CHOLESTAN 27 OIC ACID; 3ALPHA, 7ALPHA, DIHYDROXY 5BETA CHOLESTAN 27 OIC ACID; BILE ACID; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL COMPOSITION; CHEMICAL STRUCTURE; ELECTROSPRAY MASS SPECTROMETRY; ISOLATION PROCEDURE; LIGHT SCATTERING; NONHUMAN; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; RATITE; RED WINGED TINAMOU; REVERSED PHASE HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; RHYCHOTUS RUFESCENS; STRUCTURE ANALYSIS; ANIMAL; BIRD; CHEMISTRY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; METABOLISM; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; TANDEM MASS SPECTROMETRY;

ANIMALS; BILE ACIDS AND SALTS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; PALAEOGNATHAE; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; TANDEM MASS SPECTROMETRY;

EID: 67449119554     PISSN: 00222275     EISSN: 15397262     Source Type: Journal    
DOI: 10.1194/jlr.M800521-JLR200     Document Type: Article

References (42)

1. Hofmann, A. F., and L. R. Hagey. 2008. Bile acids: chemistry, pathochemistry, biology, pathobiology, and therapeutics. Cell. Mol. Life Sci. 65: 2461-2483.
2. Moschetta, A., F. Xu, L. R. Hagey, G. P. van Berge-Henegouwen, K. J. van Erpecum, J. F. Brouwers, J. C. Cohen, M. Bierman, H. H. Hobbs, J. H. Steinbach, et al. 2005. A phylogenetic survey of biliary lipids in vertebrates. J. Lipid Res. 46: 2221-2232.
3. Mukhopadhyay, S., and U. Maitra. 2004. Facile synthesis, aggregation behavior, and cholesterol solubilization ability of avicholic acid. Org. Lett. 6: 31-34.
4. Lee, S. P., R. Lester, and J. S. Pyrek. 1987. Vulpecholic acid (1α,3α,7α-trihydroxy-5β-cholan-24-oic acid): a novel bile acid of a marsupial, Trichosurus vulpecula (Lesson). J. Lipid Res. 28: 19-31.
5. Hagey, L. R., C. D. Schteingart, H-T. Ton-Nu, and A. F. Hofmann. 1994. Biliary bile acids of fruit pigeons and doves (Columbiformes): presence of 1b-hydroxychenodeoxycholic acid and conjugation with glycine as well as taurine. J. Lipid Res. 35: 2041-2048.
6. Hsia, S. L. 1971. Hyocholic and muricholic acids. In The Bile Acids: Chemistry, Physiology, and Metabolism. P.P. Nair and D. Kritchevsky, editors. Plenum Press, New York. 95-120.
7. Iida, T., S. Nishida, F. C. Chang, T. Niwa, J. Goto, and T. Nambara. 1993. Potential bile acid metabolites. 19. The epimeric 3α,6,7β-trihydroxy- and 3a*6,7β,12α-tetrahydroxy-5a-cholanoic acids. Steroids. 58: 148-152.
8. Kakiyama, G., T. Iida, T. Goto, N. Mano, J. Goto, T. Nambara, L. R. Hagey, C. D. Schteingart, and A. F. Hofmann. 2006. Identification of a novel bile acid in swans, tree ducks, and geese: 3α,7α,15atrihydroxy-5β-cholan-24-oic acid. J. Lipid Res. 47: 1551-1558.
9. Hofmann, A. F., C. D. Schteingart, and L. R. Hagey. 1995. Species differences in bile acid metabolism. In Bile Acids and Liver Diseases (International Falk Workshop), G. Paumgartner and U. Beuers, editors. Kluwer Academic Publishers, Boston. 3-30.
10. Kurosawa, T., Y. Nomura, R. Mahara, T. Yoshimura, A. Kimura, S. Ikegawa, and M. Tohma. 1995. Synthesis of 19-hydroxylated bile acids and identification of 3α,7α,12α,19-tetrahydroxy-5β-cholan-24-oic acid in human neonatal urine. Chem. Pharm. Bull. (Tokyo). 43: 1551-1557.
11. Hofmann, A. F., and L. R. Hagey. 1998. Bile acids and biliary disease: Peaceful coexistence versus deadly warfare. In Gut and Liver. H.E. Blum, C.E. Bode, J.C. Bode, and R.B. Sartor, editors. Kluwer Academic Publishers, Lancaster, UK. 85-103.
12. Ridlon, J. M., D. J. Kang, and P. B. Hylemon. 2006. Bile salt biotransformations by human intestinal bacteria. J. Lipid Res. 47: 241-259.
13. Palmer, R. H. 1972. Bile acids, liver injury, and liver disease. Arch. Intern. Med. 130: 606-617.
14. Palmer, R. H. 1976. Toxic effects of lithocholate on the liver and biliary tree. In The Hepatobiliary System. Fundamental and Pathological Mechanisms. W. Taylor, editor. Plenum Press, New York. 227-240.
15. Hofmann, A. F. 2004. Detoxification of lithocholic acid, a toxic bile acid: relevance to drug Hepatotoxicity. Drug Metab. Rev. 36: 703-722.
16. Fickert, P., A. Fuchsbichler, H-U. Marschall, M. Wagner, G. Zollner, R. Krause, K. Zatloukal, H. Jaeschke, H. Denk, and M. Trauner. 2006. Lithocholic acid feeding induces segmental bile duct obstruction and destructive cholangitis in mice. Am. J. Pathol. 168: 410-422.
17. Kihira, K., A. Okamoto, and T. Hoshita. 1987. Identification of new C27 and C24 bile acids in the bile of Alligator Mississippiensis. J. Biochem. 101: 1377-1384.
18. Kuramoto, T., Y. Kameyama, M. Kaneda, M. Shiro, T. Hoshita, and M. Une. 2000. Structure and stereochemistry of the higher bile acid isolated from turtle bile: (22S,25 R)-3α,12α,15α, 22-Tetrahydroxy-5β-cholestan-26-oic acid. Chem. Pharm. Bull. (Tokyo). 48: 53-55.
19. Hagey, L. R. 1992. Bile Acid Biodiversity in Vertebrates: Chemistry and Evolutionary Implication. PhD Dissertation. University of California, San Diego.
20. Kakiyama, G., H. Tamegai, T. Iida, K. Mitamura, S. Ikegawa, T. Goto, N. Mano, J. Goto, P. Holz, L. R. Hagey, et al. 2007. Isolation and chemical synthesis of a major novel biliary bile acid in the common wombat ( Vombatus urinus): 15α-hydroxylithocholic acid. J. Lipid Res. 48: 2682-2692.
21. Davies, S. J. J. F. 2002. Ratites and tinamous (Bird families of the world). Oxford University Press, Oxford, England. 1-360.
22. Goto, J., G. Shao, H. Miura, and T. Nambara. 1989. Separation of C-25 epimers of 5b-cholanoic acids by high performance liquid chromatography with precolumn fluorescence labeling. Anal. Sci. 5: 19-22.
23. Kihira, K., A. K. Batta, E. H. Mosbach, and G. Salen. 1979. Reverse cross-coupling in the synthesis of 3α,7α-dihydroxy-5β-cholestanoic acid. J. Lipid Res. 20: 421-427.
24. Une, M., N. Matsumoto, K. Kihira, M. Yasuhara, T. Kuramoto, and T. Hoshita. 1980. Bile salts of frogs: a new higher bile acid, 3α,7α,12α,26-tetrahydroxy-5β- cholestanoic acid from the bile of Rana plancyi. J. Lipid Res. 21: 269-276.
25. 13C-nuclear magnetic resonance spectroscopy. Hoppe Seylers Z. Physiol. Chem. 365: 479-484.
26. Ikegawa, S., T. Goto, N. Mano, and J. Goto. 1998. Substrate specificity of THCA-CoA oxidases from rat liver light mitochondrial fractions on dehydrogenation of 3α,7α, 12α-trihydroxy-5β-cholestanoic acid CoA thioester. Steroids. 63: 603-607.
27. Ikegawa, S., T. Goto, H. Watanabe, and J. Goto. 1995. Stereoisomeric inversion of (25R) and (25S)-3α,7α,12α-trihydroxy-5β-cholestanoic acids in rat liver peroxisome. Biol. Pharm. Bull. 18: 1027-1029.
28. Ikegawa, S., T. Goto, H. Watanabe, and J. Goto. 1997. Stereoisomeric bio-inversion of (25R)- and (25S)-3α,7α, 12α-trihydroxy-5β-cholestanoic acid CoA thioesters in rat liver peroxisome. Enantiomer. 2: 333-342.
29. Ikegawa, S., H. Watanabe, T. Goto, N. Mano, J. Goto, and T. Nambara. 1995. Stereospecific dehydrogenation of (25R)- and (25S)-3α,7α,12α-trihydroxy- 5β-cholestanoic acids by acyl-CoA oxidase in rat liver light mitochondrial fraction. Biol. Pharm. Bull. 18: 1041-1044.
30. Setchell, K. D., J. E. Heubi, K. E. Bove, N. C. O'Connell, T. Brewsaugh, S. K. Steinberg, A. Moser, and R. H. Squires, Jr. 2003. Liver disease caused by failure to racemize trihydroxycholestanoic acid; gene mutation and effect of bile acid therapy. Gastroenterology. 124: 217-232.
31. Une, M., Y. Tazawa, K. Tada, and T. Hoshita. 1987. Occurrence of both (25R)- and (25S)-3α,7α,12α-trihydroxy-5β-cholestanoic acids in urine from an infant with Zellweger's syndrome. J. Biochem. 102: 1525-1530.
32. Lawson, A. M., M. J. Madigan, D. Shortland, and P. T. Clayton. 1986. Rapid diagnosis of Zellweger syndrome and infantile Refsum's disease by fast atom bombardment-mass spectrometry of urine bile salts. Clin. Chim. Acta. 161: 221-231.
33. Deleze, G., I. Björkhem, and G. Karlaganis. 1986. Bile acids and bile alcohols in two patients with Zellweger (cerebro-hepato-renal) syndrome. J. Pediatr. Gastroenterol. Nutr. 5: 701-710.
34. 27-bile acids in biological samples and its application to the urine of a patient with Zellweger syndrome. Anal. Sci. 12: 839-846.
35. Obinata, K., H. Nittono, K. Yabuta, R. Mahara, and M. Tohma. 1992. 1β-hydroxylated bile acids in the urine of healthy neonates. J. Pediatr. Gastroenterol. Nutr. 15: 1-5.
36. Tohma, M., R. Mahara, H. Takeshita, T. Kurosawa, and S. Ikegawa. 1986. Synthesis of the 1β-hydroxylated bile acids, unusual bile acids in human biological fluids. Chem. Pharm. Bull. (Tokyo). 34: 2890-2899.
37. Jönsson, G., A. C. Midtvedt, A. Norman, and T. Midtvedt. 1995. Intestinal microbial bile acid transformation in healthy infants. J. Pediatr. Gastroenterol. Nutr. 20: 394-402.
38. Shoda, J., T. Osuga, R. Mahara, M. Tohma, K. Matsuura, N. Tanaka, Y. Matsuzaki, and H. Miyazaki. 1989. Altered metabolism of bile acids in cholestasis: determination of 1β and 6α-hydroxylated metabolites. J. Chromatogr. 488: 315-328.
39. Fischer, S., M. Neubrand, and G. Paumgartner. 1993. Biotransformation of orally administered ursodeoxycholic acid in man as observed in gallbladder bile, serum, and urine. Eur. J. Clin. Invest. 23: 28-36.
40. Yamakawa, R., A. Kimura, K. Aoki, M. Suzuki, R. Mahara, and M. Tohma. 1996. Urinary 1β-hydroxyursodeoxycholic acid during ursodeoxycholic acid therapy. J. Gastroenterol. 31: 917-918.
41. St. Pyrek, J., S. P. Lee, L. Thomsen, C. Tasman-Jones, and B. Leydon. 1991. Bile acids of marsupials. 2. Hepatic formation of vulpecholic acid (1α,3α,7α-trihydroxy-5β-cholan-24-oic acid) from chenodeoxycholic acid in a marsupial, Trichosurus vulpecula (Lesson). J. Lipid Res. 32: 1417-1427.
42. Bartelli, S., and L. M. Chiappe. 2005. Earliest Tinamous (Aves: Palaeognathae) from the Miocene of Argentina and their phylogenetic position. Serial Publications of the Natural History Museum of Los Angeles County. 502: 1-14.