MISC

2003年9月

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

ELECTROPHORESIS
  • M Kinuta
  • ,
  • K Kinuta
  • ,
  • H Yamada
  • ,
  • T Abe
  • ,
  • Y Yoshida
  • ,
  • K Araki
  • ,
  • SA Li
  • ,
  • A Otsuka
  • ,
  • A Nakanishi
  • ,
  • Y Moriyama
  • ,
  • K Takei

24
18
開始ページ
3212
終了ページ
3218
記述言語
英語
掲載種別
DOI
10.1002/elps.200305582
出版者・発行元
WILEY-V C H VERLAG GMBH

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.


リンク情報
DOI
https://doi.org/10.1002/elps.200305582
Web of Science
https://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcAuth=JSTA_CEL&SrcApp=J_Gate_JST&DestLinkType=FullRecord&KeyUT=WOS:000185897100017&DestApp=WOS_CPL
ID情報
  • DOI : 10.1002/elps.200305582
  • ISSN : 0173-0835
  • Web of Science ID : WOS:000185897100017

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