Determination of S-[2-carboxy-1-(1H-imidazol-4-yl)ethyl]glutathione, a novel metabolite of L-histidine, in tissue extracts from sunlight-irradiated rat by capillary electrophoresis

Masahiro Kinuta, Jun Ohta, Hiroshi Yamada, Keiko Kinuta, Tadashi Abe, Shun Ai Li, Atsushi Otsuka, Akira Nakanishi, Kohji Takei

Research output: Contribution to journalArticle

2 Citations (Scopus)

Abstract

Exposure of the skin to sunlight results in an increase in the content of epidermal urocanic acid, a key metabolite of L-histidine, and some portions of the metabolite penetrate into the body fluid. S-[2-Carboxy-1-(1H-imidazol-4-yl)ethyl]glutathione (GS(CIE)), an adduct of glutathione and urocanic acid, was proposed to be an origin of a urinary compound, S-[2-carboxy-1-(1H-imidazol-4-yl)ethyl]-L-cysteine (Cys(CIE)). Various catabolites of Cys(CIE) were also isolated from human urine previously. However, no direct evidence to show the existence of GS(CIE) as a biological material had been found. By using capillary electrophoresis, the glutathione adduct has now been found in the extracts of rat tissues from the kidney, liver, skin and blood when the rat was kept under conditions of sunlight irradiation after the fur on the dorsal skin had been clipped. On the other hand, no or a trace of GS(CIE) was determined in rat tissue extracts when the animal was kept indoor in usual manner. The glutathione adduct was isolated from the kidney extract of the sunlight-irradiated rat using ion-exchangers and high-voltage paper electrophoresis, and determined by fast-atom-bombardment mass spectrometry. These results indicate that GS(CIE) formation actually occurs in the body and that the formation is accelerated by exposing the rat to sunlight irradiation. From these findings, we propose an alternative pathway of histidine metabolism which is initiated by the adduction of urocanic acid to glutathione to form GS(CIE) and terminates with the formation of the urinary compounds via Cys(CIE).

Original languageEnglish
Pages (from-to)3365-3370
Number of pages6
JournalElectrophoresis
Volume22
Issue number16
DOIs
Publication statusPublished - 2001

Fingerprint

Capillary electrophoresis
Tissue Extracts
Sunlight
Capillary Electrophoresis
Metabolites
Histidine
Cysteine
Rats
Urocanic Acid
Glutathione
Skin
Irradiation
Fast Atom Bombardment Mass Spectrometry
Paper Electrophoresis
Kidney
Ion exchangers
Body fluids
Body Fluids
S-(2-carboxy-1-(1H-imidazol-4-yl)ethyl)glutathione
Electrophoresis

Keywords

  • Capillary electrophoresis
  • Glutathione S-conjugate
  • Imidazole compound
  • Mass spectrometry
  • Sunlight irradiation

ASJC Scopus subject areas

  • Clinical Biochemistry

Cite this

Determination of S-[2-carboxy-1-(1H-imidazol-4-yl)ethyl]glutathione, a novel metabolite of L-histidine, in tissue extracts from sunlight-irradiated rat by capillary electrophoresis. / Kinuta, Masahiro; Ohta, Jun; Yamada, Hiroshi; Kinuta, Keiko; Abe, Tadashi; Li, Shun Ai; Otsuka, Atsushi; Nakanishi, Akira; Takei, Kohji.

In: Electrophoresis, Vol. 22, No. 16, 2001, p. 3365-3370.

Research output: Contribution to journalArticle

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abstract = "Exposure of the skin to sunlight results in an increase in the content of epidermal urocanic acid, a key metabolite of L-histidine, and some portions of the metabolite penetrate into the body fluid. S-[2-Carboxy-1-(1H-imidazol-4-yl)ethyl]glutathione (GS(CIE)), an adduct of glutathione and urocanic acid, was proposed to be an origin of a urinary compound, S-[2-carboxy-1-(1H-imidazol-4-yl)ethyl]-L-cysteine (Cys(CIE)). Various catabolites of Cys(CIE) were also isolated from human urine previously. However, no direct evidence to show the existence of GS(CIE) as a biological material had been found. By using capillary electrophoresis, the glutathione adduct has now been found in the extracts of rat tissues from the kidney, liver, skin and blood when the rat was kept under conditions of sunlight irradiation after the fur on the dorsal skin had been clipped. On the other hand, no or a trace of GS(CIE) was determined in rat tissue extracts when the animal was kept indoor in usual manner. The glutathione adduct was isolated from the kidney extract of the sunlight-irradiated rat using ion-exchangers and high-voltage paper electrophoresis, and determined by fast-atom-bombardment mass spectrometry. These results indicate that GS(CIE) formation actually occurs in the body and that the formation is accelerated by exposing the rat to sunlight irradiation. From these findings, we propose an alternative pathway of histidine metabolism which is initiated by the adduction of urocanic acid to glutathione to form GS(CIE) and terminates with the formation of the urinary compounds via Cys(CIE).",
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T1 - Determination of S-[2-carboxy-1-(1H-imidazol-4-yl)ethyl]glutathione, a novel metabolite of L-histidine, in tissue extracts from sunlight-irradiated rat by capillary electrophoresis

AU - Kinuta, Masahiro

AU - Ohta, Jun

AU - Yamada, Hiroshi

AU - Kinuta, Keiko

AU - Abe, Tadashi

AU - Li, Shun Ai

AU - Otsuka, Atsushi

AU - Nakanishi, Akira

AU - Takei, Kohji

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