胆汁酸与葡萄糖和N-乙酰葡糖胺在体外的结合位置
Positions of conjugation of bile acids with glucose and N-acetylglucosamine in vitro.
作者信息
Marschall H U, Griffiths W J, Zhang J, Wietholtz H, Matern H, Matern S, Sjövall J
机构信息
Department of Internal Medicine III, Aachen University of Technology, Germany.
出版信息
J Lipid Res. 1994 Sep;35(9):1599-610.
In order to establish the position of conjugation of bile acids with glucose or N-acetylglucosamine, glucosides of chenodeoxycholic and hyodeoxycholic acids and of 13C-labeled cholic, lithocholic, chenodeoxycholic, hyodeoxycholic, and ursodeoxycholic acids, and N-acetylglucosaminides of ursodeoxycholic, isoursodeoxycholic, 3-dehydro-ursodeoxycholic, and ursodeoxycholylglycine were synthesized in vitro. The conjugates were purified by anion-exchange chromatography and reversed-phase HLPC and were analyzed by gas chromatography-mass spectrometry. The glucosides of chenodeoxycholic and hyodeoxycholic acids were also analyzed after periodate and chronic acid oxidation. All conjugates were analyzed by fast atom bombardment mass spectrometry with collision-induced dissociation. Glucose conjugation was shown to occur at C-3 in all bile acid glucosides studied. In contrast, the selective N-acetylglucosaminidation of 7 beta-hydroxy bile acids was shown to occur at the 7 beta-position.
为确定胆汁酸与葡萄糖或N-乙酰葡糖胺的结合位置，在体外合成了鹅去氧胆酸和猪去氧胆酸的葡糖苷以及13C标记的胆酸、石胆酸、鹅去氧胆酸、猪去氧胆酸和熊去氧胆酸的葡糖苷，还有熊去氧胆酸、异熊去氧胆酸、3-脱氢熊去氧胆酸和熊去氧胆酰甘氨酸的N-乙酰葡糖胺苷。通过阴离子交换色谱法和反相高效液相色谱法对结合物进行纯化，并采用气相色谱-质谱联用仪进行分析。高碘酸盐和铬酸氧化后，还对鹅去氧胆酸和猪去氧胆酸的葡糖苷进行了分析。所有结合物均通过具有碰撞诱导解离功能的快原子轰击质谱法进行分析。结果表明，在所研究的所有胆汁酸葡糖苷中，葡萄糖结合发生在C-3位。相反，7β-羟基胆汁酸的选择性N-乙酰葡糖胺化发生在7β位。
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