Isolation and identification of 1-furyl-β-carboline derivatives that are mutagenic after nitrite treatment

Article abstract of DOI:10.1248/cpb.32.1980

When a mixture of 2-furaldehyde (I) and L-tryptophan dissolved in 0.1 M phosphate buffer (pH 7.0) was kept at 37°C for 4 weeks, a browning reaction gradually occurred. The reaction mixture after treatment with nitrite at pH 4.0, was mutagenic to S. typhimurium TA100 in the absence of S9 mix. The browning solution was fractionated by applying high-performance liquid chromatography (HPLC) and thin-layer chromatography (TLC), and two 1-furyl-β-carboline derivatives were isolated. They were compound A, (1R,3S)-1-(2-furyl)-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole-3-carboxylic acid, and compound B, (1S,3S)-1-(2-furyl)-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole-3-carboxylic acid. These compounds had similar mutagenic potency toward S. typhimurium TA100 without metabolic actvity after treatment wih nitrite.

Full text of DOI:10.1248/cpb.32.1980

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