Study on the bile salt, sodium scymnol sulfate, from Rhizoprionodon acutus. II. The structures of scymnol, anhydroscymnol and sodium scymnol sulfate

Chem Pharm Bull (Tokyo). 1991 Dec;39(12):3153-6. doi: 10.1248/cpb.39.3153.

Abstract

The crystal structures of anhydroscymnol (I) and scymnol (II), which were prepared from sodium scymnol sulfate (III) isolated from the bile of Rhizoprionodon acutus, have been determined by means of X-ray diffraction analyses. The crystals of I are orthorhombic, space group P2(1)2(1)2(1) with Z = 4; unit-cell dimensions: a = 13.562(2), b = 21.636(2), c = 8.735(2) A; II orthorhombic, space group P2(1)2(1)2, with Z = 4; unit-cell dimensions a = 18.553(2), b = 19.887(2), c = 7.986(2) A. Both structures, (24R,25S)-(+)-24,26-epoxy-5 beta-cholestane-3 alpha,7 alpha,12 alpha,27-tetrol (I) and (24R)-(+)-5 beta-cholestane-3 alpha,7 alpha,12 alpha,24,26,27-hexol (II), were solved from diffractometric data by direct methods and refined by least-squares calculations to R = 0.073 (I) and R = 0.062 (II) (2044 (I) and 2250 (II) observed independent significant reflections (I greater than 3 sigma(I)), respectively. All the hydroxyl groups of both compounds are involved in a hydrogen-bonding network. The structure of III was determined to be (24R,25S)-(+)-3 alpha,7 alpha,12 alpha,24,26-pentahydroxy-5 beta-cholestan-27-yl sodium sulfate, based on the chemical data that alkaline degradation of III with aqueous potassium hydroxide gives only I.

MeSH terms

  • Bile Acids and Salts / chemistry*
  • Cholestanols / chemistry*
  • Crystallization

Substances

  • Bile Acids and Salts
  • Cholestanols
  • scymnol sulfate ester
  • anhydroscymnol
  • scymnol