7β-Hydroxy bile alcohols: Facile synthesis and 2D 1H NMR studies of 5β-cholestane-3α,7β,12α,25-tetrol

Steroids

Volumn 62, Issue 5, 1997, Pages 409-414

  Dayal, Bishambar ^a,c   Ertel, N H ^b   Padia, J ^d   Rapole, K R ^a   Salen, G ^a  

^a RUTGERS NEW JERSEY MEDICAL SCHOOL   (United States)

^b ROBERT WOOD JOHNSON MEDICAL SCHOOL   (United States)

^c VETERANS AFFAIRS MEDICAL CENTER   (United States)

^d NONE

Author keywords

1D and 2D NMR; 7 Hydroxy bile alcohol; Cerebrotendinous xanthomatosis; Fast atom bombardment mass spectrometry; Microwave induced reaction; Ursocholic acid

Indexed keywords

5BETA CHOLESTANE 3ALPHA,7BETA,12ALPHA,25 TETROL; ALCOHOL DERIVATIVE; MAGNESIUM DERIVATIVE; MESYLIC ACID; UNCLASSIFIED DRUG; URSOCHOLIC ACID;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; ESTERIFICATION; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS;

BILE ACIDS AND SALTS; CHOLESTANOLS; HUMANS; HYDROXYLATION; MAGNETIC RESONANCE SPECTROSCOPY; SPECTROMETRY, MASS, FAST ATOM BOMBARDMENT; XANTHOMATOSIS, CEREBROTENDINOUS;

EID: 0030920197     PISSN: 0039128X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0039-128X(97)00007-X     Document Type: Article

References (33)

1. Salen G, Shefer S, Berginer VD (1983). Familial diseases with storage of sterols other than cholesterol: Cerebrotendinous xanthomatosis and sitosterolemia with xanthomatosis. In: Stanbury JB, Wyngaarden JB, Fredrickson DS, Goldstein JL, Brown MS (eds). The Metabolic Basis of Inherited Disease. McGraw-Hill, New York: pp. 713-730.
2. Dayal B, Salen G, Shefer S (1995). Structure and biosynthesis of bile alcohols: Disorders of cholesterol side-chain oxidation in cerebrotendinous xanthomatosis. In: Atta-ur-Rahman (ed.), Studies in Natural Products Chemistry, Vol. 17. Elsevier, North-Holland, Amsterdam, pp. 208-231.
3. Setoguchi T, Salen G, Tint GS, Mosbach EH (1974). A biochemical abnormality in cerebrotendinous xanthomatosis: Impairment of bile acid synthesis associated with incomplete degradation of the cholesterol side chain. J Clin invest 53:1393-1401.
4. Shefer S, Cheng FW, Dayal B, Hauser S, Tint GS, Salen G, Mosbach EH (1976). A 25-hydroxylation pathway of cholic acid biosynthesis in man and rat. J Clin Invest 57:897-903.
5. Dayal B, Rapole KR, Seong WM, Salen G (1994). Asymmetric syntheses and lanthanide-induced CD studies of (24R and 24S) 5β-cholestane-3α,7α,12α,24,25-pentols. Pure Appl Chem 66:2037-2040.
6. Dayal B, Salen G, Padia J, Shefer S, Tint GS, Williams TH, Toome V, Sasso G (1992). Stereoselective synthesis of (24R,24S) 5β-cholestane-3α,7α,12α,24,25-pentol and (25R,25S) 5β-cholestane-3α,7α,12α,25,26-pentol using a modified osmium catalyzed sharpless asymmetric dihydroxylation process. Chem Phys Lipids 61: 271-281.
7. Dayal B, Tint GS, Batta AK, Shefer S, Salen G (1983). Chemical synthesis of 3α,7α,12α,25-tetrahydroxy-5β-cholestan-24-one: An intermediate in the 25-hydroxylation pathway of cholic acid biosynthesis from cholesterol. J Lipid Res 24:208-210.
8. Salen G, Shefer S, Cheng FW, Dayal B, Batta AK, Tint GS (1979). Cholic acid biosynthesis: The enzymatic defect in cerebrotendinous xanthomatosis. J Clin Invest 63:38-44.
9. Dayal B, Salen G, Padia J, Shefer S, Tint GS, Sasso G, Williams TH (1993). Bile alcohol glucuronides: Regioselective O-glucuronidation of 5β-cholestane-3α,7α,12α,25-tetrol and 24-nor-5β-cholestane-3α,7α,12α,25-tetrol, Carbohydr Res 240: 133-142.
10. Salen G, Shefer S, Tint GS, Nicolau G, Dayal B, Batta AK (1985). Biosynthesis of bile acids in cerebrotendinous xanthomatosis: Relationship of bile acids pool sizes and synthesis rates to hydroxylations at C-12, C-25, and C-26. J Clin Invest 76:744-751.
11. Oftebro H, Björkhem I, Skrede S, Screiner A, Pedersen JI (1980). Cerebrotendinous xanthomatosis: A defect in mitochondrial 26-hydroxylation required for normal biosynthesis of cholic acid. J Clin Invest 65:1418-1430.
12. Björkhem I, Fauson O, Hopen G, Oftebro H, Pedersen JI, Skrede S (1983). Role of the 26-hydroxylase in the biosynthesis of bile acids in the normal state and in cerebrotendinous xanthomatosis. J Clin Invest 71:142-143.
13. Leitersdorf E, Reshef A, Meiner V, Levitzki S, Schwartz P, Dann EJ, Berkman N, Cali JJ, Klapholz L, Berginer VM (1993). Frame-shift and splice-j-junction mutations in the sterol 27-hydroxylase gene cause cerebrotendinous xanthomathosis in Jews of Moroccan origin. J Clin Invest 91:2488-2496.
14. Cali JJ, Hesieh CL, Francke U, Russell DW (1991). Mutations in the bile acid biosynthetic enzyme sterol 27-hydroxylase underlie cerebrotendinous xanthomathosis. J Biol Chem 266:7779-7783.
15. Reshef A, Meiner V, Beginer VM, Leitersdorf E (1994). Molecular genetics of cerebrotendious xanthomatosis in Jews of North African origin. J Lipid Res 35:478-483.
16. 1H NMR (2D NMR studies) investigation of isoursocholic acid. J Lipid Res 32:1381-1387.
17. Pramanik BN, Das PR, Bose AK (1989). Molecular ion enhancement using salts in FAB-matrix for studies on complex natural products. J Natural Product 52:534-546.
18. Dayal B, Salen G, Tint GS, Shefer S, Benz SW (1990). Use of positive ion fast atom bombardment mass spectrometry for rapid identification of a bile alcochol glucuronide isolated from cerebrotendinous xanthomatosis patients. Steroids 55:74-78.
19. Dayal B, Rapole KR, Wilson SR, Shefer S, Tint GS, Salen G (1995). Microwave-induced rapid synthesis of bile acid conjugates. Synlett 861-862.
20. Dayal B, Rapole KR, Salen G (1995). Microwave-induced organic reactions of bile acids: Esterification, deformylation, and deacetylation using mild reagents: Methanesulfonic acid/methanol and or para-toluenesulfonic acid/methanol. Steroids 60:453-457.
21. Dayal B, Rapole KR, Patel C, Shefer S, Tint GS, Salen G (1995). Microwave-induced rapid synthesis of sarcosine conjugated bile acids. Bioorg Med Chem Lett 5:1301-1306.
22. Tsemg KY, Klein PD (1977). Formylated bile acids: Improved synthesis, properties, and partial deformylation. Steroids 29:635-648.
23. Dayal B, Shefer S, Tint GS, Salen G, Mosbach EH (1976). Synthesis of 5β-cholestane-3α,7α,12α,25-tetrol and 5β-cholestane-3α,7α,12α,24ξ,25-pentol. J Lipid Res 17:74-77.
24. Dayal B, Greeley DN, Williams TH, Tint GS, Salen G (1984). Stereospecific synthesis of 3β-hydroxylated bile alcohols. J Lipid Res 25:646-650.
25. Hudlicky T, Sheth JP (1979). Synthesis of dienic acids. Application of Arndt-Eistert reaction to unsaturated diazoketones. Tetrahedron Lett 2267-2670.
26. Dayal B, Bagan E, Speck J, Salen G (1980). A facile synthesis of 5β-cholestane-3α,7α,12α,25-tetrol. Steroids 35:439-444.
27. Croasmun WM, Carlson RMK (1987). Steroid structural analysis by two-dimentional NMR. In: Croasmun WM, Carlson RMK (eds), Two-Dimensional NMR for Chemists and Biochemists. VCH Publishers, New York, chap. 7, pp. 387-424.
28. Wehrli FW, Marchand AP, Wehrli S (1983). Interpretation of Carbon-13 NMR Spectra, 2nd Ed. Wiley, New York.
29. Doddrell DM, Pegg DT, Bendall MR (1982). Distortionless enhancement of NMR signals by polarization transfer. J Magn Reson 48:323-327.
30. Mostafa K, Vion-Dury J, Confort-Gouny S, Favre R, Viout P, Sciaky M, Sari H, Cozzone PJ (1993). Analysis of plasma lipids by NMR spectroscopy: Application to modifications induced by malignant tumors. J Lipid Res 34:1009-1019.
31. Waterhouse DV, Barens S, Muccio DD (1985). Nuclear magnetic resonance spectroscopy of bile acids. Development of two-dimensional NMR methods for the elucidation of proton resonance assignments for five common hydroxylated bile acids, and their parent bile acid, 5β-cholanoic acid. J Lipid Res 26:1068-1078.
32. Iida T, Tamaura T, Matsumoto T, Chang FC (1983). Carbon-13 NMR spectra of hydroxylated bile acid stereoisomers. Org Magn Reson 21:305.
33. 22-β-muricholate) in the serum of female rats treated with α-naphthylisothiocyanate. J Lipid Res 34: 651-661.