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 in the Hornbills, (24R,25S)-3α,7α,24-Trihydroxy-5β-cholestan-27-oyl Taurine and Its 12α-Hydroxy Derivative
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犀鸟体内两种主要胆汁酸，(24R,25S)-3α,7α,24-三羟基-5β-胆甾烷-27-酰基牛磺酸及其12α-羟基衍生物
DOI：
10.1007/s11745-016-4150-0
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发表时间：
2016
期刊：
影响因子：
1.9
通讯作者：
T.Iida.
中科院分区：
文献类型：
--
作者：
R.Satoh;H.Ogata;T.Saito;B.Zhou;K.Omura;S.Kurabuchi;K.Mitamura;S.Ikegawa;L.R.Hagey;A.F.Hofmann;T.Iida.
从犀鸟目犀鸟科两种犀鸟的胆囊胆汁中分离出两种主要的胆汁酸：Buceros bicornis（大犀鸟）和Penelopides panini（维萨扬tarictic犀鸟）。它们的结构被确定为3α，7 α，24-二羟基-5 β-胆甾烷-27-酸及其12α-羟基衍生物3α，7 α，12 α，24-四羟基-5 β-胆甾烷-27-酸（Varanic acid，VA），两者均以其相应的牛磺酸酰胺化物存在于胆汁中。合成了4种异烟酸的非对映体，并通过X-射线衍射分析确定了它们的结构。发现VA及其12-脱氧衍生物具有（24 R，25 S）-构型。另外13种犀鸟也通过HPLC进行了分析，显示出与B相似的胆汁酸模式。bicornisandP.先前从蜥蜴和毒蜥胆汁中分离的（24 R，25 S）-VA的立体化学归属现在应该修改为（24 S，25 S）-构型。
Two major bile acids were isolated from the gallbladder bile of two hornbill species from the Bucerotidae family of the avian order BucerotiformesBuceros bicornis(great hornbill) andPenelopides 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 toB. bicornisandP. 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.