Food Chemistry

28 1 Amino Acids, Peptides, Proteins

Table 1.7.Mutagenic compounds from various heated foods and from model systems

Mutagenic compound Short form Food Structure
Model systema

2-Amino-3-methylimidazo-
[4,5-f]quinoline

IQ 1,2,3

2-Amino-3,4-dimethylimidazo-
[4,5-f]quinoline

MelQ 3

2-Amino-3-methylimidazo-
[4,5-f]quinoxaline

IQx 2

2-Amino-3,8-dimethylimidazo-
[4,5-f]quinoxaline

MelQ2x 2,3

2-Amino-3,4,8-trimethyl-
imidazo-[4,5-f]quinoxaline

4,8-Di MelQx 2,3,5,6

2-Amino-3,7,8-trimethyl-
imidazo-[4,5-f]quinoxaline

7,8-Di MelQx 4

2-Amino-1-methyl-6-phenyl-
imidazo[4,5-b]pyridine

PhIP 2

a1: Meat extract; 2: Grilled meat; 3: Grilled fish; 4: Model mixture of creatinine, glycine, glucose;

5: as 4, but alanine; 6: as 4, but threonine

Tetrahydro-β-carboline-3-carboxylic acid (II)
and (1S, 3S)-(III) and (1R, 3S)-methyltetrahydro-
β-carboline-3-carboxylic acid (IV) were
detected in beer (II: 2–11 mg/L, III + IV:
0 .3–4 mg/L) and wine (II: 0.8–1.7mg/L,
III + IV: 1.3–9.1mg/L). The ratio of diastere-

omers III and IV (Formula 1.58) was always
near 2:1:

(1.58)

The compounds are pharmacologically active.