Document Detail

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.
MedLine Citation:
PMID:  14518047     Owner:  NLM     Status:  MEDLINE    
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.
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:
Type:  Journal Article; Research Support, Non-U.S. Gov't    
Journal Detail:
Title:  Electrophoresis     Volume:  24     ISSN:  0173-0835     ISO Abbreviation:  Electrophoresis     Publication Date:  2003 Sep 
Date Detail:
Created Date:  2003-09-30     Completed Date:  2004-06-14     Revised Date:  2006-11-15    
Medline Journal Info:
Nlm Unique ID:  8204476     Medline TA:  Electrophoresis     Country:  Germany    
Other Details:
Languages:  eng     Pagination:  3212-8     Citation Subset:  IM    
Department of Neuroscience, Okayama University, Graduate School of Medicine, and Dentistry, Okayama, Japan.
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MeSH Terms
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, Wistar
Skin / metabolism,  radiation effects
Spectrometry, Mass, Fast Atom Bombardment
Urocanic Acid / metabolism*
Reg. No./Substance:
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 Transferase

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