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Biochem J. 1969 Sep; 114(2): 179–184.
PMCID: PMC1184842

Comparative studies of bile salts. Bile salts of the lamprey Petromyzon marinus L

G. A. D. Haslewood
Guy's Hospital Medical School, London S.E. 1
L. Tökés
Syntex Research, Palo Alto, Calif. 94304, U.S.A.


1. Bile salts of Petromyzon marinus L. ammocoetes appeared to consist solely or chiefly of a crystalline substance, whose chromatographic and i.r.-spectral characteristics suggested that it was a monosulphate ester of a bile alcohol having the 3α,7α,12α-trihydroxy pattern of substitution in a 5α-steroid nucleus. 2. This substance on cleavage with dioxan–trichloroacetic acid gave petromyzonol, n.m.r. and mass-spectral examination of which suggested the structure 5α-cholane-3α,7α,12α,24-tetrol. 3. 3α,7α,12α-Trihydroxy-5α-cholanoic acid (allocholic acid) from the lizards Anolis lineatopus lineatopus Gray and Cyclura carinata Harlan (family Iguanidae) was esterified with propan-1-ol and reduced by lithium aluminium hydride to 5α-cholane-3α,7α,12α,24-tetrol, identical with petromyzonol. 4. Chromic acid oxidation of petromyzonol sulphate from lamprey bile, followed by acid hydrolysis, gave 24-hydroxy-5α-cholane-3,7,12-trione; hence the sulphate ester group is at C-24. 5. Petromyzonol sulphate is both primitive and unique: a study of its biogenesis might improve our understanding of evolution at the molecular level.

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Selected References

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  • ANDERSON IG, HASLEWOOD GA. Comparative studiesof 'bile salts'. 15. The natural occurrence and preparation of allocholic acid. Biochem J. 1962 Oct;85:236–242. [PMC free article] [PubMed]
  • Anderson IG, Haslewood GA. Comparative studies of bile salts. 16-Deoxymyxinol, a second bile alcohol from hagfish. Biochem J. 1969 May;112(5):763–765. [PMC free article] [PubMed]
  • Anderson IG, Haslewood GA, Cross AD, Tökés L. New evidence for the structure of myxinol. Biochem J. 1967 Sep;104(3):1061–1063. [PMC free article] [PubMed]
  • BRIDGWATER RJ, BRIGGS T, HASLEWOOD GA. Comparative studies of 'bile salts'. 14. Isolation from shark bile and partial synthesis of scymnol. Biochem J. 1962 Feb;82:285–290. [PMC free article] [PubMed]
  • Djerassi C, Tökés L. Mass spectrometry in structural and stereochemical problems. 93. Further observations on the importance of interatomic distance in the McLafferty rearrangement. Synthesis and fragmentation behavior of deuterium-labeled 12-keto steroids. J Am Chem Soc. 1966 Feb 5;88(3):536–544. [PubMed]
  • Haslewood GA, Tammar AR. Comparative studies of bile salts. Bile salts of sturgeons (Acipenseridae) and of the paddlefish Polyodon spathula: a new partial synthesis of 5 beta-cyprinol. Biochem J. 1968 Jun;108(2):263–268. [PMC free article] [PubMed]
  • HOSHITA R, KOUCHI M, KAZUNO R. Stero-bile acids and bile sterols. XLIX. Synthesis of 3alpha, 7alpha, 12alpha, 26, 27-pentahydroxycoprostane. J Biochem. 1963 Apr;53:291–294. [PubMed]
  • Hoshita T, Shefer S, Mosbach EH. Conversion of 7-alpha,12-alpha-dihydroxycholest-4-en-3-one to 5-alpha-cholestane-3-alpha, 7-alpha,12-alpha-triol by iguana liver microsomes. J Lipid Res. 1968 Mar;9(2):237–243. [PubMed]

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