Major biliary bile acids of the medaka (Oryzias latipes): 25R- and 25S-epimers of 3alpha,7alpha,12alpha-trihydroxy-5beta-cholestanoic acid.

Major biliary bile acids of the medaka (Oryzias latipes): 25R- and 25S-epimers of 3alpha,7alpha,12alpha-trihydroxy-5beta-cholestanoic acid.
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DOI:
10.2108/zsj.27.565
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发表时间:
2010-07
期刊:
影响因子:
0.9
通讯作者:
Hofmann AF
Hofmann AF
中科院分区:
生物学4区
文献类型:
--
作者:
Hagey LR;Lida T;Tamegai H;Ogawa S;Une M;Asahina K;Mushiake K;Goto T;Mano N;Goto J;Krasowski MD;Hofmann AF

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分离鉴定了青竹、日本米鱼胆汁中的胆盐。只有胆汁酸存在,而且都是N-酰胺化牛磺酸。用柱层析法分离得到3种胆汁酸,占总胆汁酸的98%,并通过与合成标准物质的性质比较,推测了它们的结构。胆汁酸主要是3-α,7-α,12-α-三羟基-5-β-胆甾烷-27-OIC酸的25R-异构体(82%)。25S-同分异构体也存在(11%),胆酸(5%)也存在。结合多种1D和2D核磁共振技术,完成了C-25异构体的~1H和~(13)C核磁共振信号归属。氢原子和碳原子的~1H和~(13)C核磁共振化学位移和谱型接近于以C-25为中心的不对称,为区分这两个表观非对映异构体提供了确凿的证据。青竹是第一种被鉴定为以C27胆汁酸为主的鱼类,其主要胆盐。
The biliary bile salts of the medaka, the Japanese rice fish (Oryzias latipes) were isolated and identified. Only bile acids were present, and all were N-acyl amidated with taurine. Three bile acids, constituting 98% of total bile acids, were isolated by chromatography and their structure inferred from their properties compared to those of synthetic standards when analyzed by liquid chromatography-tandem mass spectrometry. The dominant bile acid was the 25R-epimer (82%) of 3α,7α,12α-trihydroxy-5β-cholestan-27-oic acid. The 25S-epimer was also present (11%), as was cholic acid (5%). Complete 1H and 13C NMR signal assignments of the C-25 epimers were made by using a combination of several 1D- and 2D-NMR techniques. The 1H and 13C NMR chemical shifts and spectral patterns of the hydrogen and carbon atoms, being close to the asymmetric centered at C-25, provided confirmatory evidence in that they distinguished the two epimeric diastereomers. The medaka is the first fish species identified as having C27 biliary bile acids as dominant its major bile salts.
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