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Identification of 4-Methylspinaceamine, a Pictet−Spengler Condensation Reaction Product of Histamine with Acetaldehyde, in Fermented Foods and Its Metabolite in Human Urine

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journal contribution
posted on 06.09.2006, 00:00 by Takeshi Ohya
Previous study demonstrated that 4-methylspinaceamine (4-methyl-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine), a Pictet−Spengler condensation reaction product of histamine with acetaldehyde, is present in human urine. The current study sought to determine whether 4-methylspinaceamine is present in fermented foods; its presence might be expected since both histamine and acetaldehyde are often present in these foods. Soy sauce, fish sauce, cheese, and shao hsing wine (Chinese wine) were found to contain 4-methylspinaceamine. The concentration of 4-methylspinaceamine excreted in human urine was greatly elevated after ingestion of a meal containing soy sauce as a dietary source of 4-methylspinaceamine, demonstrating that the level of 4-methylspinaceamine in human urine was affected by dietary foods. In addition, a metabolite of 4-methylspinaceamine in human urine was investigated. An enhanced peak in the HPLC chromatogram of human urine samples after ingestion of 4-methylspinaceamine-containing foods was observed. A peak at the same retention time was also observed from a human urine sample after administration of 4-methylspinaceamine, suggesting that the peak was due to a metabolite. By comparison with the newly synthesized authentic compound, the metabolite was identified as 1,4-dimethylspinaceamine. Keywords: 4-methylspinaceamine; 1,4-dimethylspinaceamine; 4-methyl-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine; 1,4-dimethyl-4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine; acetaldehyde; histamine; Pictet−Spengler reaction; fermented foods; metabolite