TY - JOUR
T1 - Biliary bile acids in birds of the Cotingidae family
T2 - Taurine-conjugated (24R,25R)-3α,7α,24-trihydroxy-5β-cholestan-27-oic acid and two epimers (25R and 25S) of 3α,7α-dihydroxy-5β-cholestan-27-oic acid
AU - Hagey, Lee R.
AU - Iida, Takashi
AU - Ogawa, Shoujiro
AU - Adachi, Yuuki
AU - Une, Mizuho
AU - Mushiake, Kumiko
AU - Maekawa, Masamitsu
AU - Shimada, Miki
AU - Mano, Nariyasu
AU - Hofmann, Alan F.
N1 - Funding Information:
This work was supported in part by a Grant-in-Aid for Scientific Research from the Ministry of Education, Culture, Sports, Science and Technology of Japan (to T.I., 21550091 ) for 2009–2011 and for the Strategic Research Base Development Program for Private Universities subsidized MEXT 2009 ( S0901022 ).
PY - 2011/9
Y1 - 2011/9
N2 - Three C27 bile acids were found to be major biliary bile acids in the capuchinbird (Perissocephalus tricolor) and bare-throated bellbird (Procnias nudicollis), both members of the Cotingidae family of the order Passeriformes. The individual bile acids were isolated by preparative RP-HPLC, and their structures were established by RP-HPLC, LC/ESI-MS/MS and NMR as well as by a comparison of their chromatographic properties with those of authentic reference standards of their 12α-hydroxy derivatives. The most abundant bile acid present in the capuchinbird bile was the taurine conjugate of C 27 (24R,25R)-3α,7α,24-trihydroxy-5β-cholestan-27-oic acid, a diastereomer not previously identified as a natural bile acid. The four diastereomers of taurine-conjugated (24ξ,25ξ)-3α,7α,24- trihydroxy-5β-cholestan-27-oic acid could be distinguished by NMR and were resolved by RP-HPLC. The RRT of the diastereomers (with taurocholic acid as 1.0) were found to be increased in the following order: (24R,25R) < (24S,25R) < (24S,25S) < (24R,25S). Two epimers (25R and 25S) of C27 3α,7α-dihydroxy-5β-cholestan-27-oic acid were also present (as the taurine conjugates) in both bird species. Epimers of the two compounds could be distinguished by their NMR spectra and resolved by RP-HPLC with the (25S)-epimer eluting before the (25R)-epimer. Characterization of the taurine-conjugated (24R,25R)-3α,7α,24-trihydroxy-5β-cholestan- 27-oic acid and two epimers (25R and 25S) of 3α,7α-dihydroxy- 5β-cholestan-27-oic acid should facilitate their detection in peroxisomal disease and inborn errors of bile acid biosynthesis.
AB - Three C27 bile acids were found to be major biliary bile acids in the capuchinbird (Perissocephalus tricolor) and bare-throated bellbird (Procnias nudicollis), both members of the Cotingidae family of the order Passeriformes. The individual bile acids were isolated by preparative RP-HPLC, and their structures were established by RP-HPLC, LC/ESI-MS/MS and NMR as well as by a comparison of their chromatographic properties with those of authentic reference standards of their 12α-hydroxy derivatives. The most abundant bile acid present in the capuchinbird bile was the taurine conjugate of C 27 (24R,25R)-3α,7α,24-trihydroxy-5β-cholestan-27-oic acid, a diastereomer not previously identified as a natural bile acid. The four diastereomers of taurine-conjugated (24ξ,25ξ)-3α,7α,24- trihydroxy-5β-cholestan-27-oic acid could be distinguished by NMR and were resolved by RP-HPLC. The RRT of the diastereomers (with taurocholic acid as 1.0) were found to be increased in the following order: (24R,25R) < (24S,25R) < (24S,25S) < (24R,25S). Two epimers (25R and 25S) of C27 3α,7α-dihydroxy-5β-cholestan-27-oic acid were also present (as the taurine conjugates) in both bird species. Epimers of the two compounds could be distinguished by their NMR spectra and resolved by RP-HPLC with the (25S)-epimer eluting before the (25R)-epimer. Characterization of the taurine-conjugated (24R,25R)-3α,7α,24-trihydroxy-5β-cholestan- 27-oic acid and two epimers (25R and 25S) of 3α,7α-dihydroxy- 5β-cholestan-27-oic acid should facilitate their detection in peroxisomal disease and inborn errors of bile acid biosynthesis.
KW - 24-Hydroxylation
KW - 3α,7α,12α,24-Tetrahydroxy-5β-cholestan-27-oic acid
KW - 3α,7α,24-Trihydroxy-5β-cholestan- 27-oic acid
KW - 3α,7α-Dihydroxy- 5β-cholestan-27-oic acid
KW - H and C NMR
KW - Bile acid metabolism
KW - C bile acids
KW - LC/ESI-MS/MS
KW - Taurine conjugate
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U2 - 10.1016/j.steroids.2011.04.017
DO - 10.1016/j.steroids.2011.04.017
M3 - Article
C2 - 21600907
AN - SCOPUS:79960453168
SN - 0039-128X
VL - 76
SP - 1126
EP - 1135
JO - Steroids
JF - Steroids
IS - 10-11
ER -