Heterocyclic amines: Chemistry and health

Abstract

Heterocyclic amines (HAs) occur at the ppb range in foods. Most of them demonstrate potent mutagenicity in bacteria mutagenicity test, and some of them have been classified by the International Agency for Research on Cancer as probable/possible human carcinogens. Their capability of formation even during ordinary cooking practices implies frequent exposure by the general public. Over the past 30 years, numerous studies have been stimulated aiming to alleviate human health risk associated with HAs. These studies contribute to the understanding of their formation, characterization, and quantification in foods; their mutagenesis/carcinogenesis, mechanisms of antimutagenesis by chemical or phytogenic modulators; and strategies to inhibit their formation. The chemistry of HAs, their implications in human health, factors influencing their formation, and feasible ways of suppression will be briefly reviewed. Their occurrence in trace amounts in foods necessitates continuous development and amelioration of analytical techniques. Various inhibitory strategies, ranging from modifying cooking conditions to incorporation of different modulators, have been developed. This will remain one of the foremost areas of research in the field of food chemistry and safety.

Reduced Oxidant Stress and Extended Lifespan in Mice Exposed to a Low Glycotoxin Diet

“…15,16,18 -21,24 -26 Nutrients that are thermally prepared for consumption are a rich source of protein-or fat-derived oxidation derivatives, including AGEs, and a host of toxic compounds in foods, some of which have been implicated in oncogenesis. [27][28][29][30][31][32] Laboratory rodent food is high in protein, low in fat, supplemented with micronutrients, and routinely heated to ensure safety. The temperatures currently used are sufficiently high to inadvertently cause standard mouse chow to be rich in oxidant AGEs, not unlike levels present in the usual Western diet.…”

Optimised extraction of heterocyclic aromatic amines from blood using hollow fibre membrane liquid-phase microextraction and triple quadrupole mass spectrometry

“…269 3). Separation of HCAs has traditionally been achieved under acidic LC conditions 270 [1,12], on the principle that mobile phase pH should be lower than the analyte pKa (<pH 271 5 for the HCAs) in order to fully protonate the HCA amine groups prior to positive mode 272 electrospray ionisation. However, baseline chromatographic separation of the DiMeIQx 273 isomers is sensitive to pH and is incomplete under the commonly used pH 4.7 or lower 274…”

Acid-labile protein-adducted heterocyclic aromatic amines in human blood are not viable biomarkers of dietary exposure: A systematic study

“…Heterocyclic aromatic amines (HCA) are formed during combustion of tobacco and cooking of proteinrich foods, particularly meat and fish, which provide creatin(in)e and other precursors such as amino acids, sugars or other aldehydes (Cheng et al, 2006;Puangsombat et al, 2012;Aaslyng et al, 2013). 2-Amino-1-methyl-6-phenylimidazo(4,5-b)pyridine (PhIP), 2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline (MeIQx) and 2-amino-3,4,8-trimethylimidazo[4,5-f]quinoxaline (4, are three of the most abundant HCAs in cooked meat and fish (Lynch et al, 1995;Zhang et al, 2013) although many others have been identified (Ni et al, 2008).…”