16.S.1 Biosynthesis of Bile Acids and Bile Alcohols
647
a)
(5a) Allocholic acid
(5~) Cholic acid
b)
Fig. 16.16 a, b. Bile alcohols and bile acids [2S, 46]. a Spatial structure of the Sa and S~ bile acids, illustrated with
(Sa) allocholic acid (3a,7a,12a-trihydroxy-Sa-cholanic
acid) and (S~) cholic acid (3a,7a,12a-trihydroxy-S~cholanic acid (R = CH(CH3)CH2CH2COOH). b The ring
systems and side-chains of bile acids and alcohols: the possible substitution sites are numbered. For clarity, the conjugation residues have been omitted. However, in the gall
bladder all alcohols carry a sulphate residue on one of the
primary OH groups of the side-chain; myxinol bissulphate
has sulphate residues on C-3 and on C-26 (or C-27). All
bile acids are conjugated with taurine (or glycine).
The trivial and systematic names of all bile acids and alcohols mentioned in the text:
Bile alcohols
Arapaimol B
Scymnol
Sa-Dermophol
S~-Dermophol
ArapaimolA
Sa-Chimaerol
S~-Chimaerol
5a-Bufol
S~-Bufol
Sa-Cyprinol
S~-Cholestan-2~,3a,7a,12a,
26,27-hexol
S~-Cholestan-3a,7a,12a,24,26,27hexol
Sa-Cholestan-3a, 7 a ,12a ,2S ,26,27hexol
S~-Cholestan-3a,7a,12a,2S,26,27hexol
S~-Cholestan-2~-3a,7a,12a,26pentol
Sa-Cholestan-3a,7a,12a,24,26pentol
S ~-Cholestan-3a, 7 a ,12a,24 ,26pentol
Sa-Cholestan-3a, 7 a,12a,2S ,26pentol
S~-Cholestan-3a,7a,12a,2S,26pentol
Sa-Cholestan-3a,7a,12a,26,27pentol (Fig. 16.17)
R
R=
~
4 26
23
25
27
24 - Methylcholestan
Latimerol
26-Deoxy-5achimaerol
27-Deoxy-5acyprinol
Myxinol
5a-Ranol
5~-Ranol
Sa-Petromyzonol
Bile acids
Chenodeoxycholic
acid
Deoxycholic acid
H yodoexycholic
acid
Lithocholic acid
a-Muricholic acid
~-Muricholic acid
w-Muricholic acid
Phocaecholic acid
Pythocholic acid
Ursodeyxycholic
acid
Varanic acid
Cholestan
27 -Norcholestan
26,27 - Dinorcholestan
Cholan
Sa-Cholestan-3~,7a,12a,26,27pentol
Sa-Cholestan-3a,7a,12a,24-tetrol
Sa-Cholestan-3a, 7 a,12a , 26-tetrol
Sa-Cholestan-3~,7a,16a,26-tetrol
(24R)-27-Nor-Sa-cholestan3a,7a,12a,24,26-pentol
(24R)-27-Nor-S~-cholestan3a,7a,12a,24,26-pentol
5a-Cholan-3a,7a,12a,24-tetrol
3a,7a-Dihydroxy-S~-cholanic acid
(Fig. 16.17)
3a,12a-Dihydroxy-S~-cholanic acid
(Fig. 16.17)
3a,6a-Dihydroxy-5~-cholanic acid
3a,7a-Hyxdroxy-SB-cholanic acid
(Fig. 16.17)
3a,6B,7a-Trihydroxy-5B-cholanic
acid
3a,6B,7B-Trihydroxy-5~-cholanic
acid
3a,6a,7~-Trihydroxy-SB-cholanic
acid
3a, 7 a ,23-Trihydroxy-S~-cholanic
acid
3a,12a,16a-Trihydroxy-5~-cholanic
acid
3a,7~-Dihydroxy-5B-cholanic acid
3a,7a,12a,24-Tetrahydroxy-5Bcholestanic acid