Evolutionary relationships of bile alcohols and

bile acids

species bile alcohol or bile acid (trivial name)

Elasmobranch fishes

Myxine glutinosa (hagfish) 5 b1;-cholestane-3 b2;,7 b1;,16 b1;,26-tetrol (myxinol)

Mustelus manazo (dogfish) 5 b2;-cholestane-3 b1;,7 b1;,12 b1;,24,26,27-hexol (scymnol)

Teleostian fishes

Latimeria chalumnae (coelacanth) 5 b1;-cholestane-3 b2;,7 b1;,12 b1;,26,27-pentol (latimerol)

Cyprinus carpio (carp) 5 b1;-cholestane-3 b1;,7 b1;,12 b1;,26,27-pentol (5 b1;-cyprinol)

Amphibians

Rana temporaria (frog) 5 b1;,27-norcholestane-3 b1;,7 b1;,12 b1;,24,26-pentol (5 b1;-ranol)

Bufo vulgaris japonica (toad) 5 b2;-cholestane-3 b1;,7 b1;,12 b1;,25,26-pentol (5 b2;-bufol)

Reptiles

Alligator mississippiensis (alligator) 3 b1;,7 b1;,12 b1;-trihydroxy-5 b2;-cholestan-27-oic acid (trihydroxycoprostanoic acid)

Bitis arietans (puff adder) 3 b1;,12 b1;,23-trihydroxy-5 b1;-cholanoic acid (bitocholic acid)

Birds

Anser domesticus (goose) 3 b1;,7 b1;-dihydroxy-5 b2;-cholanoic acid (chenodeoxycholic acid)

Mammals

humans and most (but not all) other species 3 b1;,7 b1;,12 b1;-trihydroxy-5 b2;-cholanoic acid (cholic acid)

3 b1;,12 b1;-dihydroxy-5 b2;-cholanoic acid (deoxycholic acid)

3 b1;-hydroxy-5 b2;-cholanoic acid (lithocholic acid)