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. 1968 Jun;108(2):263–268. doi: 10.1042/bj1080263

Comparative studies of bile salts. Bile salts of sturgeons (Acipenseridae) and of the paddlefish Polyodon spathula: a new partial synthesis of 5β-cyprinol

G A D Haslewood 1, A R Tammar 1
PMCID: PMC1198802  PMID: 5665889

Abstract

1. Bile salts of the sturgeons Acipenser guldenstaedti Brandt, Acipenser stellatus Pall and Huso huso L. and of the paddlefish Polyodon spathula Walbaum are shown to be closely similar, consisting mainly of taurocholate with minor amounts of tauroallocholate and the monosulphates of bile alcohols. The bile alcohols, comprising less than 10% of the bile salts, are mixtures with high proportions of substances resembling C27 tetrols and of C27 pentols, including 5β-cyprinol and (probably) 5α-cyprinol. 2. 5β-Cyprinol (3α,7α,12α,26,27-pentahydroxy-5β-cholestane) was made from cholic acid via 3α,7α,12α-triacetoxy-5β-cholan-24-ol in an overall yield of about 0·8%. 3. The chemical nature of chondrostean bile salts agrees with the systematic position of the fishes and suggests further correspondence between evolution at the morphological and molecular levels.

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Selected References

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