2009_Book_FoodChemistry

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 system a
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-trimethylimidazo-[4,5-f
]quinoxaline
4,8-Di MelQx 2,3,5,6
2-Amino-3,7,8-trimethylimidazo-[4,5-f
]quinoxaline
7,8-Di MelQx 4
2-Amino-1-methyl-6-phenylimidazo[4,5-b]pyridine
PhIP 2
a 1: 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)-methyltetrahydroβ-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 diastereomers
III and IV (Formula 1.58) was always
near 2:1:
(1.58)
The compounds are pharmacologically active.