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Identification of a novel conjugate in human urine: bile acid acyl galactosides
Authors:Goto Takaaki  Shibata Akihiro  Sasaki Daisuke  Suzuki Naoto  Hishinuma Takanori  Kakiyama Genta  Iida Takashi  Mano Nariyasu  Goto Junichi
Institution:Graduate School of Pharmaceutical Sciences, Tohoku University, Aobayama, Aoba-ku, Sendai 980-8578, Japan.
Abstract:We report a novel conjugate, bile acid acyl galactosides, which exist in the urine of healthy volunteers. To identify the two unknown peaks obtained in urine specimens from healthy subjects, the specimens were subjected to solid phase extraction and then to liquid chromatographic separation. The eluate corresponding to the unknown peaks on the chromatogram was collected. Following alkaline hydrolysis and liquid chromatography (LC)/electrospray ionization (ESI)-mass spectrometric (MS) analysis, cholic acid (CA) and deoxycholic acid (DCA) were identified as liberated bile acids. When a portion of the alkaline hydrolyzate was subjected to a derivatization reaction with 1-phenyl-3-methyl-5-pyrazolone, a derivative of galactose was detected by LC/ESI-MS. Finally, the liquid chromatographic and mass spectrometric properties of these unknown compounds in urine specimens were compared to those of authentic specimens and the structures were confirmed as CA 24-galactoside and DCA 24-galactoside. These results strongly imply that bile acid 24-galactosides, a novel conjugate, were synthesized in the human body.
Keywords:APCI  atmospheric pressure chemical ionization  CA  cholic acid  CDCA  chenodeoxycholic acid  DCA  deoxycholic acid  ESI  electrospray ionization  HDCA  hyodeoxycholic acid  LC  liquid chromatography  LCA  lithocholic acid  MS  mass spectrometry  MS/MS  tandem mass spectrometry  PMP  3-methyl-1-phenyl-5-pyrazolone  Rks  relative retention factors  UGT  UDP-glucuronosyltransferase  UDCA  ursodeoxycholic acid
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