Two Major Bile Acids in the Hornbills, (24R,25S)-3α,7α,24-Trihydroxy-5β-cholestan-27-oyl Taurine and Its 12α-Hydroxy Derivative.
Two major bile acids were isolated from the gallbladder bile of two hornbill species from the Bucerotidae family of the avian order Bucerotiformes Buceros bicornis (great hornbill) and Penelopides panini (Visayan tarictic hornbill). Their structures were determined to be 3α,7α,24-dihydroxy-5β-cholestan-27-oic acid and its 12α-hydroxy derivative, 3α,7α,12α,24-tetrahydroxy-5β-cholestan-27-oic acid (varanic acid, VA), both present in bile as their corresponding taurine amidates. The four diastereomers of varanic acid were synthesized and their assigned structures were confirmed by X-ray crystallographic analysis. VA and its 12-deoxy derivative were found to have a (24R,25S)-configuration. 13 additional hornbill species were also analyzed by HPLC and showed similar bile acid patterns to B. bicornis and P. panini. The previous stereochemical assignment for (24R,25S)-VA isolated from the bile of varanid lizards and the Gila monster should now be revised to the (24S,25S)-configuration.
Department of Chemistry, College of Humanities and Sciences, Nihon University, Sakurajousui, Setagaya, Tokyo, 156-8550, Japan.
Rika
R
Satoh
Department of Chemistry, College of Humanities and Sciences, Nihon University, Sakurajousui, Setagaya, Tokyo, 156-8550, Japan.
Hiroaki
H
Ogata
Department of Chemistry, College of Humanities and Sciences, Nihon University, Sakurajousui, Setagaya, Tokyo, 156-8550, Japan.
Tetsuya
T
Saito
Department of Chemistry, College of Humanities and Sciences, Nihon University, Sakurajousui, Setagaya, Tokyo, 156-8550, Japan.
Biao
B
Zhou
Department of Chemistry, College of Humanities and Sciences, Nihon University, Sakurajousui, Setagaya, Tokyo, 156-8550, Japan.
Kaoru
K
Omura
Faculty of Pharmaceutical Sciences, Kinki University, Kowakae, Higashi-Osaka, 577-8502, Japan.
Satoshi
S
Kurabuchi
Faculty of Pharmaceutical Sciences, Kinki University, Kowakae, Higashi-Osaka, 577-8502, Japan.
Kuniko
K
Mitamura
Faculty of Pharmaceutical Sciences, Kinki University, Kowakae, Higashi-Osaka, 577-8502, Japan.
Shigeo
S
Ikegawa
Department of Medicine, University of California at San Diego, La Jolla, San Diego, CA, 92093-063, USA.
Lee R
LR
Hagey
Department of Medicine, University of California at San Diego, La Jolla, San Diego, CA, 92093-063, USA.
Alan F
AF
Hofmann
Department of Chemistry, College of Humanities and Sciences, Nihon University, Sakurajousui, Setagaya, Tokyo, 156-8550, Japan. takaiida@chs.nihon-u.ac.jp.
Takashi
T
Iida
D000818:Animals; D001647:Bile Acids and Salts / Q000032:analysis* / Q000737:chemistry; D001717:Birds / Q000378:metabolism; D002851:Chromatography, High Pressure Liquid; D018360:Crystallography, X-Ray; D005704:Gallbladder / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism; D013654:Taurine / Q000031:analogs & derivatives / Q000737:chemistry* / Q000302:isolation & purification
D001647:Bile Acids and Salts; D013654:Taurine
(24R,25S)-3α,7α,12α,24-Tetrahydroxy-5β-cholestan-27-oyl taurine; (24R,25S)-3α,7α,24-Trihydroxy-5β-cholestan-27-oyl taurine; 24-Hydroxylated bile acid; Cholestanoic acid; Great hornbill; NMR; RP-HPLC; Varanic acid; Visayan tarictic hornbill; X-ray crystallography