A novel varanic acid epimer - (24R,25S)-3α,7α,12α,24- tetrahydroxy-5β-cholestan-27-oic acid - Is a major biliary bile acid in two varanid lizards and the Gila monster

Steroids

Volumn 77, Issue 13, 2012, Pages 1510-1521

  Hagey, Lee R ^a   Ogawa, Shoujiro ^b   Kato, Narimi ^b   Satoh, Rika ^b   Une, Mizuho ^c   Mitamura, Kuniko ^d   Ikegawa, Shigeo ^d   Hofmann, Alan F ^a   Iida, Takashi ^b  

^a UNIVERSITY OF CALIFORNIA SAN DIEGO   (United States)

^b NIHON UNIVERSITY   (Japan)

^c HIROSHIMA INTERNATIONAL UNIVERSITY   (Japan)

^d KINKI UNIVERSITY   (Japan)

Author keywords

25R 25S Hydroxylation; Bile acid metabolism; C27 bile acid; Monitor lizard; Peroxisomes; Taurine conjugate

Indexed keywords

(24R,25S) 3A,7A,12A,24 TETRAHYDROXY 5 BETA CHOLESTAN 27 OIC ACID; BILE ACID; CHOLESTANE DERIVATIVE; TAURINE; UNCLASSIFIED DRUG;

ARTICLE; BILE DUCT; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL STRUCTURE; EPIMER; HELODERMA SUSPECTUM; LIZARD; MASS SPECTROMETRY; NONHUMAN; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS; VARANUS KOMODOENSIS; VARANUS OLIVACEUS;

ANIMALS; BILE ACIDS AND SALTS; BILIARY TRACT; CHOLESTANOLS; LIZARDS; STEREOISOMERISM;

HELODERMA SUSPECTUM; HELODERMATIDAE; SQUAMATA; VARANIDAE; VARANUS; VARANUS KOMODOENSIS; VARANUS OLIVACEUS;

EID: 84867606904     PISSN: 0039128X     EISSN: 18785867     Source Type: Journal    
DOI: 10.1016/j.steroids.2012.08.017     Document Type: Article

References (26)

1. A.F. Hofmann, L.R. Hagey, and M.D. Krasowski Bile salts of vertebrates: structural variation and possible evolutionary significance J Lipid Res 51 2010 226 246
2. L.R. Hagey, N. Vidal, A.F. Hofmann, and M.D. Krasowski Evolutionary diversity of bile salts in reptiles and mammals, including analysis of ancient human and extinct giant ground sloth coprolites BMC Evol Biol 10 2010 133 156
3. L.R. Hagey, N. Vidal, A.F. Hofmann, and M.D. Krasowski Complex evolution of bile salts in birds The Auk 127 2010 820 831
4. L.R. Hagey, T. Iida, H. Tamegai, S. Ogawa, M. Une, and K. Asahina Major biliary bile acids of the medaka (Oryzias latipes): 25R- and 25S-epimers of 3α,7α,12α-trihydroxy-5β-cholestanoic acid Zool Sci 27 2010 565 573
5. G.A.D. Haslewood, and V. Wootton Comparative studies of bile salts: 1. Preliminary survey Biochem J 47 1950 584 597
6. T. Kazuno, and A. Mori The synthesis of stero-bile acid VI. The synthesis of trihydroxycoprostane Proc Japan Acad 30 1954 486 487
7. S. Bergström, H. Danielsson, and B. Samuelsson Formation and metabolism of bile acids in Lipid Metabolism K. Bloch, 1960 John Wiley and Sons, Inc. 291 336
8. H. Seno The synthesis of stero-bile acids XXII. The metabolism of trihydroxycoprostane and trihydroxy-24-methyl-coprostane in the guinea pig Proc Japan Acad 32 1956 139 142
9. H.M. Suld, E. Staple, and S. Gurin Mechanism of formation of bile acids from cholesterol: oxidation of 5β-cholestane-3α,7α,12α- triol and formation of propionic acid from the side chain by rat liver mitochondria J Biol Chem 237 1962 338 344
10. Y. Inai, Y. Tanaka, S. Betsuki, and T. Kazuno Stero-bile acids and bile sterols: LXVI. Synthesis of 3α,7α,12α,24ξ-tetrahydroxy- coprostanic acid J Biochem 56 1964 591 593
11. T. Masui, and E. Staple The formation of cholic acid from 3α,7α,12α,24ξ-tetrahydroxycoprostanic acid by rat liver Biochim Biophys Acta 104 1965 305 307
12. T. Masui, and E. Staple The formation of bile acids from cholesterol: the conversion of 5β-cholestane-3α,7α,12α-triol-26-oic acid to cholic acid via 5β-cholestane-3α,7α,12α,24ξ- tetraol-26-oic acid I by rat liver J Biol Chem 241 1966 3889 3893
13. B.G. Collings, and G.A.D. Haslewood The chemical nature of varanic acid Biochem J 99 1966 50 51
14. S. Ferdinandusse, S.K. Denis, P.L. Faust, and R.J.A. Wanders Bile acids: the role of peroxisomes J Lipid Res 50 2009 2139 2147
15. J.I. Pedersen, and J. Gustafsson Conversion of 3α,7α, 12α-trihydroxy-5β-cholestanoic acid into cholic acid by rat liver peroxisomes FEBS Lett 121 1980 345 348 (Pubitemid 11165190)
16. L.R. Hagey, and S.K. Krisans Degradation of cholesterol to propionic acid by rat liver peroxisomes Biochem Biophys Res Commun 107 1982 834 841 (Pubitemid 13207670)
17. T. Kurosawa, M. Sato, F. Kikuchi, T. Watanabe, T. Suga, and M. Tohma Effect of the hydroxyl group on the oxidative cleavage (β-oxidation) of steroidal side chain for bile acid biosynthesis in rat liver homogenate Steroids 62 1997 474 481 (Pubitemid 27248915)
18. P. Vreken, A. van Rooij, S. Denis, E.G. van Grunsven, D.A. Cuebas, and R.J.A. Wanders Sensitive analysis of serum 3α,7α,12α,24- tetrahydroxy-5β-cholestan-26-oic acid diastereomers using gas chromatography-mass spectrometry and its application in peroxisomal D-bifunctional protein deficiency J Lipid Res 39 1998 2452 2458 (Pubitemid 29006309)
19. M. Une, A. Inoue, and T. Hoshita Formation of varanic acid, 3α,7α,12α,24-tetrahydroxy-5β-cholestanoic acid from 3α,7α,12α-trihydroxy-5β-cholestanoic acid in Bombina orientalis Steroids 61 1996 639 641 (Pubitemid 26379416)
20. M. Une, F. Nagai, K. Kihira, T. Kuramoto, and T. Hoshita Synthesis of four diastereoisomers at carbons 24 and 25 of 3α,7α,12α,24- tetrahydroxy-5β-cholestan-26-oic acid, intermediates of bile acid biosynthesis J Lipid Res 24 1983 924 929
21. T. Momose, T. Tsubaki, T. Iida, and T. Nambara An improved synthesis of taurine- and glycine-conjugated bile acids Lipids 32 1997 775 778 (Pubitemid 27328060)
22. L.R. Hagey, T. Iida, S. Ogawa, Y. Adachi, M. Une, and K. Mushiake Biliary bile acids in birds of cotingidae family: taurine-conjugated (24R,25R)-3α,7α,24-trihydroxy-5β-cholestan-27-oic acid and two epimers (25R and 25S) of 3α,7α-dihydroxy-5β-cholestan-27-oic acid Steroids 76 2011 1126 1135
23. P.V. Demarco, E. Farkas, D. Doddrell, B.L. Mylari, and E. Wenkert Pyridine-induced solvent shifts in the nuclear magnetic resonance spectra of hydroxylic compounds J Am Chem Soc 90 1968 5480 5486
24. 13C NMR spectra of steroids: a survey and commentary Org Magn Reson 9 1977 439 464
25. A.K. Batta, G. Salen, J.F. Blount, and S. Shefer Configuration at C-25 in 3α,7α,12α-trihydroxy-5β-cholestan-26-oic acid by X-ray crystallography J Lipid Res 20 1979 935 940
26. A.K. Farrants, G.I. Andersen, and S.E. Bystrom Configuration of the 3α,7α,12α-trihydroxy-5β-cholest-24-enoic acid, an intermediate in the peroxisomal conversion of 3α,7α,12-trihydroxy- 5β-cholestanoic acid to cholic acid in rat liver Biochem Int 26 1992 725 730