scholarly journals Comparative studies of ‘bile salts’. 6. Partial synthesis of coprostanic acid, a ‘stem acid’ of primitive bile salts

1952 ◽  
Vol 52 (4) ◽  
pp. 588-590 ◽  
Author(s):  
R. J. Bridgwater ◽  
G. A. D. Haslewood
Keyword(s):  
Comparative Studies ◽  
Bile Salts ◽  
Partial Synthesis

scholarly journals Comparative studies of bile salts. A new type of bile salt from Arapaima gigas (Cuvier) (family Osteoglossidae)

1972 ◽  
Vol 126 (5) ◽  
pp. 1161-1170 ◽  
Author(s):  
G. A. D. Haslewood ◽  
L. Tökés
Keyword(s):  
Bile Salt ◽  
Cholic Acid ◽  
Mass Spectroscopy ◽  
Comparative Studies ◽  
Bile Salts ◽  
Trichloroacetic Acid ◽  
Partial Synthesis ◽  
Arapaima Gigas ◽  
New Type

1. Arapaima gigas bile salts were hydrolysed by alkali or cleaved with dioxan–trichloroacetic acid to give cholic acid, arapaimic acid, arapaimol-A and arapaimol-B. 2. I.r., n.m.r. and mass spectroscopy and [α]D measurements indicated that arapaimic acid and arapaimol-A and -B are respectively 2α,3α,7α,12α-tetrahydroxy−5β,25∈-cholestan-26-oic acid, 5β,25R-cholestane-2β,3α,7α,12α,26-pentol and 5β-cholestane-2β,3α,7α,12α,26,27-hexol. 3. Partial synthesis of 2β,3α,7α,12α-tetrahydroxy−5α- and −5β-cholan-24-oic acid and their spectral examination fully confirmed these conclusions. 4. A. gigas bile salts show primitive features in that they comprise alcohol sulphates and a C27 acid; they are also specialized in showing 2β-hydroxylation.

scholarly journals Comparative studies of ‘bile salts’. 14. Isolation from shark bile and partial synthesis of scymnol

1962 ◽  
Vol 82 (2) ◽  
pp. 285-290 ◽  
Author(s):  
RJ BRIDGWATER ◽  
T BRIGGS ◽  
GAD HASLEWOOD
Keyword(s):  
Comparative Studies ◽  
Bile Salts ◽  
Partial Synthesis

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

1968 ◽  
Vol 108 (2) ◽  
pp. 263-268 ◽  
Author(s):  
G. A. D. Haslewood ◽  
A. R. Tammar
Keyword(s):  
Cholic Acid ◽  
Comparative Studies ◽  
Bile Salts ◽  
Chemical Nature ◽  
Systematic Position ◽  
Huso Huso ◽  
Partial Synthesis ◽  
Polyodon Spathula ◽  
Acipenser Stellatus ◽  
The Sturgeons

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.

scholarly journals Comparative studies of ‘bile salts’. 18. The chemistry of cyprinol

1964 ◽  
Vol 90 (2) ◽  
pp. 303-308 ◽  
Author(s):  
IG Anderson ◽  
T Briggs ◽  
GAD Haslewood
Keyword(s):  
Comparative Studies ◽  
Bile Salts

scholarly journals Comparative studies of ‘bile salts’. 1. Preliminary survey

1950 ◽  
Vol 47 (5) ◽  
pp. 584-597 ◽  
Author(s):  
G. A. D. Haslewood ◽  
Veryan Wootton
Keyword(s):  
Comparative Studies ◽  
Bile Salts ◽  
Preliminary Survey

scholarly journals Comparative studies of 'bile salts'. 2. Pythocholic acid

1951 ◽  
Vol 49 (1) ◽  
pp. 67-71 ◽  
Author(s):  
G. A. D. Haslewood ◽  
Veryan M. Wootton
Keyword(s):  
Comparative Studies ◽  
Bile Salts

scholarly journals Comparative studies of bile salts. 5α-Chimaerol, a new bile alcohol from the white sucker Catostomus commersoni Lacépède

1970 ◽  
Vol 116 (4) ◽  
pp. 581-585 ◽  
Author(s):  
I. G. Anderson ◽  
G. A. D. Haslewood
Keyword(s):  
Bile Acids ◽  
Comparative Studies ◽  
Bile Salts ◽  
Mass Spectra ◽  
Parallel Evolution ◽  
White Sucker ◽  
Minor Constituent ◽  
Catostomus Commersoni ◽  
Bile Alcohol ◽  
A Minor

1. G.l.c. examination of bile alcohols prepared from the sucker Catostomus commersoni Lacépède (family Catostomidae) showed that although 5α-cyprinol (5α-cholestane-3α,7α,12α,26,27-pentol) was a minor constituent, the principal bile alcohol was an undescribed substance, probably present in the bile as the C-26 sulphate ester, whose i.r., n.m.r. and mass spectra agreed with the structure 5α-cholestane-3α,7α,12α,24,26-pentol. 2. MD studies suggest that this 5α-chimaerol is the 24(+), 25S enantiomer and that 5β-chimaerol (chimaerol) from Chimaera monstrosa bile also has the 24(+), 25S configuration. These findings imply that bile alcohol biosynthesis in suckers and chimaeras includes stereospecific oxidation of cholesterol at C-26. 3. C. commersoni bile acids (present in minor amounts) probably consist largely of 3α,7α,12α-trihydroxy-5α-cholan-24-oic acid (allocholic acid). 4. 5α-Chimaerol sulphate and 5α-cyprinol sulphate are probably biochemically equivalent as bile salts, and can be considered as arising by parallel evolution.

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