UPLC–MS/MS Analysis of Heterocyclic Amines in Cooked Food

Abstract2-amino-1-methyl-6-phenylimidazole[4,5-b]pyridine (PhIP) is one of the most abundant Heterocyclic amines (HAs) in meat products. Zanthoxylum bungeanum Maxim. leaf (ZML) extract has been shown to be rich in polyphenols, which are gaining increasing interest as efficient tools for inhibiting the formation of HAs. In the present work, the effects of ZML extract, major polyphenols, chlorogenic acid, hyperoside and quercitrin on the formation of PhIP in both roast beef patties and chemical model systems were investigated. UPLC-MS showed that ZML extract and those three polyphenols effectively inhibited PhIP formation. Additionally, GC-MS analysis showed that those three polyphenols significantly reduced the content of phenylacetaldehyde in the model systems, a key intermediate involved in PhIP formation. The subsequent UPLC-MS and TOF-MS/MS analysis found that hyperoside and quercitrin reacted with phenyacetaldehyde to form those four adducts, 8-C-(E-Phenylethenyl)hyperoside, 6-C-(E-Phenylethenyl)hyperoside, 8-C-(E-Phenylethenyl)quercitrin and 6-C-(E-Phenylethenyl)quercitrin, respectively. The results revealed that hyperoside and quercitrin could trap phenylacetaldehyde to form adducts, thereby, retarding the reaction of phenylacetaldehyde and creatinine, blocking the generation of PhIP.

Download Full-text

Metabolic Fate of Heterocyclic Amines from Cooked Food

Mutagens in Food: Detection and Prevention ◽

10.1201/9781351074872-13 ◽

2018 ◽

pp. 143-156

Author(s):

Alexander Jan ◽

Wallin Halkan

Keyword(s):

Heterocyclic Amines ◽

Metabolic Fate ◽

Cooked Food

Download Full-text

Aryl hydrocarbon receptor activation and CYP1A induction by cooked food-derived carcinogenic heterocyclic amines in human HepG2 cell lines

Food and Chemical Toxicology ◽

10.1016/j.fct.2016.09.021 ◽

2016 ◽

Vol 97 ◽

pp. 256-264 ◽

Cited By ~ 4

Author(s):

Masashi Sekimoto ◽

Haruna Sumi ◽

Takuomi Hosaka ◽

Takashi Umemura ◽

Akiyoshi Nishikawa ◽

...

Keyword(s):

Aryl Hydrocarbon Receptor ◽

Hepg2 Cell ◽

Cell Lines ◽

Receptor Activation ◽

Heterocyclic Amines ◽

Aryl Hydrocarbon ◽

Cyp1a Induction ◽

Cooked Food ◽

Hepg2 Cell Lines

Download Full-text

Impact of aqueous doash extract on urinary mutagenicity in rats exposed to heterocyclic amines

Toxicology and Industrial Health ◽

10.1177/0748233711427053 ◽

2011 ◽

Vol 29 (2) ◽

pp. 142-148 ◽

Cited By ~ 4

Author(s):

Jehan A Khan ◽

Jalaluddin A Jalal ◽

C Ioanndes ◽

Said S Moselhy

Keyword(s):

Mutagenic Activity ◽

The Body ◽

Heterocyclic Amines ◽

Control Group ◽

Herbaceous Plant ◽

Carcinogen Metabolism ◽

Folk Remedy ◽

Activation System ◽

Cooked Food ◽

Origanum Majorana

Doash ( Origanum majorana) is an herbaceous plant found commonly in Saudi Arabia. It is used as a food flavor and a folk remedy to treat a number of diseases. The 2-amino-3-methylimidazo[4,5-f] quinoline (IQ) and 2-amino-1-methyl-6-phenylimidazo[4,5- b]pyridine (PhIP) are the most abundant of the heterocyclic amine carcinogens present in cooked food. In the present study, the potential of doash tea to influence carcinogen metabolism was investigated indirectly using heterocyclic amines as model mutagens, IQ and PhIP. Results obtained showed that doash tea had no influence on body weight in both the studies. Rats were treated with different doses of IQ (1, 3, 5 and 10 mg/kg) or PhIP (1, 5, 10 and 20 mg/kg). The selected dosage was 5 mg/kg for both heterocyclic amines. Results obtained revealed that rats treated with doash tea and given a single dose of the heterocyclic amines, whether for 1 day (short-term) or for 1 month (long term), showed a statistically significant decrease in their excretion of indirect mutagens (IQ or PhIP). Following treatment of the rats with a single oral dose of IQ or PhIP, the highest mutagenic activity determined in the presence of an activation system was excreted in the urine after 24 h, with much lower levels of mutagencity being excreted during subsequent elimination from the body. No mutagenicity was observed in the absence of an activation system that is direct-acting mutagenicity using (IQ and PhIP). Statistical analysis revealed that, in comparison with the control group, the aqueous doash extract significantly reduced the mutagenic response after 24 h. It was concluded that doash extract significantly decreased the excretion of mutagens in comparison with the control group (water only).

Download Full-text