Source:http://linkedlifedata.com/resource/pubmed/id/17331817
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rdf:type | |
lifeskim:mentions | |
pubmed:issue |
1
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pubmed:dateCreated |
2007-7-24
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pubmed:abstractText |
The formation of thioester-linked glutathione (GSH) conjugates of bile acids (BAs) is presumed to occur via trans-acylation reactions between GSH and reactive acyl-linked metabolites of BAs. The present study examines the chemical reactivity of cholyl-adenylate and cholyl-CoA thioester, acyl-linked metabolites of cholic acid (CA), with GSH to form CA-GSH conjugate in vitro. The authentic specimen of CA-GSH was synthesized along with GSH conjugates of four common BAs found in the human body. Their structures were confirmed by proton-nuclear magnetic resonance spectroscopy and electrospray ionization (ESI)-tandem mass spectrometry in positive- and negative-ion modes. Incubation of cholyl-adenylate or cholyl-CoA thioester with GSH was carried out at pH 7.5 and 37 degrees C for 30 min, with analysis of the reaction mixture by liquid chromatography/ESI-tandem mass spectrometry, where CA-GSH was detected on the product ion mass chromatograms monitored with stable and abundant dehydrated positive-ion [M+HH(2)O](+) at m/z 680.3 and fragmented negative-ion [GSHH](-) at m/z 306.0, and was definitely identified by CID spectra by comparison with those of the authentic sample. The results show that both cholyl-adenylate and cholyl-CoA thioester are able to acylate GSH in vitro.
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pubmed:language |
eng
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pubmed:journal | |
pubmed:citationSubset |
IM
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pubmed:chemical |
http://linkedlifedata.com/resource/pubmed/chemical/Adenosine Monophosphate,
http://linkedlifedata.com/resource/pubmed/chemical/Bile Acids and Salts,
http://linkedlifedata.com/resource/pubmed/chemical/Cholic Acid,
http://linkedlifedata.com/resource/pubmed/chemical/Cholic Acids,
http://linkedlifedata.com/resource/pubmed/chemical/Glutathione,
http://linkedlifedata.com/resource/pubmed/chemical/cholyl-adenylate
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pubmed:status |
MEDLINE
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pubmed:month |
Aug
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pubmed:issn |
1570-0232
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pubmed:author | |
pubmed:issnType |
Print
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pubmed:volume |
855
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pubmed:owner |
NLM
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pubmed:authorsComplete |
Y
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pubmed:pagination |
88-97
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pubmed:meshHeading |
pubmed-meshheading:17331817-Adenosine Monophosphate,
pubmed-meshheading:17331817-Bile Acids and Salts,
pubmed-meshheading:17331817-Cholic Acid,
pubmed-meshheading:17331817-Cholic Acids,
pubmed-meshheading:17331817-Chromatography, Liquid,
pubmed-meshheading:17331817-Glutathione,
pubmed-meshheading:17331817-Hydrogen-Ion Concentration,
pubmed-meshheading:17331817-Spectrometry, Mass, Electrospray Ionization,
pubmed-meshheading:17331817-Tandem Mass Spectrometry,
pubmed-meshheading:17331817-Temperature
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pubmed:year |
2007
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pubmed:articleTitle |
Analysis of bile acid glutathione thioesters by liquid chromatography/electrospray ionization-tandem mass spectrometry.
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pubmed:affiliation |
Faculty of Pharmaceutical Sciences, Kinki University, Higashi, Osaka, Japan. mitamura@phar.kindai.ac.jp
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pubmed:publicationType |
Journal Article,
Research Support, Non-U.S. Gov't
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