| Formation of S-[2-carboxy-1-(1H-imidazol-4-yl) ethyl]glutathione, a new metabolite of L-histidine, from cis-urocanic acid and glutathione by the action of glutathione S-transferase. | |
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MedLine Citation:
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PMID: 14518047 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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Exposure of the skin to sunlight results in an increase of the content of epidermal trans-urocanic acid, a key metabolite of L-histidine, and also in occurrence of the isomerization of trans-urocanic acid to the cis isomer. S-[2-Carboxy-1-(1H-imidazol-4-yl)ethyl]glutathione (GS(CIE)), an adduct of urocanic acid and glutathione, is a presumed origin of a urinary compound S-[2-carboxy-1-(1H-imidazol-4-yl)ethyl]-L-cysteine (Cys(CIE)). The formation of GS(CIE) is stimulated by exposing the skin to sunlight irradiation. In this study we investigated an enzymatic formation of GS(CIE) from glutathione and cis-urocanic acid by incubation with rat liver extract that contained glutathione S-transferase (GST) at high activity. The formation of GS(CIE) was suppressed significantly when a liver extract depleted of GST activity was used. Enzymatic degradation of GS(CIE) with gamma -glutamyl transpeptidase resulted in the formation of N-[S-[2-carboxy-1-(1H-imidazol-4-yl)ethyl]-L-cysteinyl]glycine, a metabolic intermediate between the glutathione adduct and Cys(CIE). A hydrolyzed product of GS(CIE) by HCl was identical with the urinary Cys(CIE). Compounds were analyzed by high-voltage paper electrophoresis, capillary electrophoresis, and fast atom bombardment mass spectrometry. From these results, we suggest that GS(CIE) formed from cis-urocanic acid and glutathione is an origin of the urinary compound Cys(CIE) and that the formation reaction is catalyzed mostly by the action of GST. |
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Authors:
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Masahiro Kinuta; Keiko Kinuta; Hiroshi Yamada; Tadashi Abe; Yumi Yoshida; Kenta Araki; Shun-Ai Li; Atsushi Otsuka; Akira Nakanishi; Yoshinori Moriyama; Kohji Takei |
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Publication Detail:
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Type: Journal Article; Research Support, Non-U.S. Gov't |
Journal Detail:
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Title: Electrophoresis Volume: 24 ISSN: 0173-0835 ISO Abbreviation: Electrophoresis Publication Date: 2003 Sep |
Date Detail:
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Created Date: 2003-09-30 Completed Date: 2004-06-14 Revised Date: 2006-11-15 |
Medline Journal Info:
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Nlm Unique ID: 8204476 Medline TA: Electrophoresis Country: Germany |
Other Details:
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Languages: eng Pagination: 3212-8 Citation Subset: IM |
Affiliation:
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Department of Neuroscience, Okayama University, Graduate School of Medicine, and Dentistry, Okayama, Japan. mkinuta@md.okayama-u.ac.jp |
Export Citation:
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| MeSH Terms | |
Descriptor/Qualifier:
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Animals Cysteine / analogs & derivatives, urine Electrophoresis, Capillary Electrophoresis, Paper Glutathione / analogs & derivatives*, analysis, biosynthesis*, metabolism Glutathione Transferase / deficiency, metabolism* Histidine / metabolism* Imidazoles / analysis Liver / chemistry, enzymology* Rats Rats, Wistar Skin / metabolism, radiation effects Spectrometry, Mass, Fast Atom Bombardment Stereoisomerism Sunlight Urocanic Acid / metabolism* |
| Chemical | |
Reg. No./Substance:
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0/Imidazoles; 104-98-3/Urocanic Acid; 134381-44-5/S-(2-carboxy-1-(1H-imidazol-4-yl)ethyl)glutathione; 52-90-4/Cysteine; 70-18-8/Glutathione; 71-00-1/Histidine; EC 2.5.1.18/Glutathione Transferase |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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