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• W2080950829 abstract "The formation of 4-hydroxy-2-nonenal (HNE) conjugates with glutathione (GSH) by Michael addition and subsequent cleavage to yield the related mercapturic acid (MA) conjugates are a major detoxication process. To characterize the metabolic pathways involved in the formation of urinary HNE−MA conjugates in the rat, the metabolism of HNE−thioethers (HNE−GSH, HNE−MA, and HNE−Cys) by rat liver and kidney cytosolic fractions was investigated. The experimental results showed that HNE−GSH is a good substrate for cytosolic incubations whereas HNE−MA and HNE−Cys are poorly metabolized. About 80% of the urinary MA conjugates originate from the primary and major HNE metabolite, namely, the hemiacetalized HNE−GSH. The direct reduction of HNE−GSH by a cytosolic aldo-keto reductase (NADPH) leads to 1,4-dihydroxynonene−GSH (DHN−GSH) and subsequently to DHN−MA. The direct oxidation of HNE−GSH by aldehyde dehydrogenase (NAD)+ leads to 4-hydroxynonenoic−lactone−GSH, the partial hydrolysis of which occurs at physiological pH and accounts for the corresponding 4-hydroxynonenoic−GSH. Both the spontaneous- and the glutathione S-transferases-catalyzed retro-Michael cleavages of HNE−GSH and HNA−lactone−GSH are the source of HNE and HNA−lactone, respectively. This latter compound, with both lipophilic and electrophilic properties, is available for microsomal ω-hydroxylation by cytochrome P450 4A enzymes and conjugation with thiol groups and therefore is the most likely candidate for the formation of ω-hydroxylated HNE−mercapturic acid conjugates excreted in rat urine." @default.
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• W2080950829 date "2003-02-07" @default.
• W2080950829 modified "2023-10-18" @default.
• W2080950829 title "Identification of Intermediate Pathways of 4-Hydroxynonenal Metabolism in the Rat" @default.
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• W2080950829 doi "https://doi.org/10.1021/tx025671k" @default.
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