Metabolism of the food-associated carcinogen 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine by human intestinal microbiota

Journal of Agricultural and Food Chemistry
L VanhaeckeT Van de Wiele

Abstract

2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine is a putative human carcinogenic heterocyclic aromatic amine formed from meat and fish during cooking. Although the formation of hazardous PhIP metabolites by mammalian enzymes is well-documented, nothing is known about the PhIP transformation potency of human intestinal bacteria. In this study, the in vitro metabolism of PhIP by human fecal samples was investigated. Following anaerobic incubation of PhIP with stools freshly collected from six healthy volunteers, we found that PhIP was extensively transformed by the human intestinal bacteria. HPLC analysis showed that the six human fecal microbiota transformed PhIP with efficiencies from 47 to 95% after 72 h incubation, resulting in one major derivative. ESI-MS/MS, HRMS, 1D (1H, 13C, DEPT) and 2D (gCOSY, gTOCSY, gHMBC, gHSQC) NMR, and IC analysis elucidated the complete chemical identity of the microbial PhIP metabolite as 7-hydroxy-5-methyl-3-phenyl-6,7,8,9-tetrahydropyrido[3',2':4,5]imidazo[1,2-a]pyrimidin-5-ium chloride. At present, no information is available about the biological activity of this newly discovered bacterial PhIP metabolite. Our findings however suggest that bacteria derived from the human intestine play a key r...Continue Reading

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Citations

May 19, 2009·European Journal of Nutrition·Adriana Nowak, Zdzislawa Libudzisz
Sep 4, 2007·Food and Chemical Toxicology : an International Journal Published for the British Industrial Biological Research Association·L VanhaeckeT Van de Wiele
Mar 26, 2016·International Journal of Medical Microbiology : IJMM·Kirill S SmirnovPhilippe Schmitt-Kopplin
Jul 23, 2016·Drug Testing and Analysis·A I DecloedtL Vanhaecke
May 23, 2017·Environmental Science & Technology·Stephanie L Wright, Frank J Kelly
Jul 2, 2017·Toxicological Sciences : an Official Journal of the Society of Toxicology·Jianbo ZhangShana J Sturla
Jul 28, 2012·Journal of Agricultural and Food Chemistry·Julie A L KieboomsLynn Vanhaecke
Jul 7, 2017·Journal of Agricultural and Food Chemistry·Falco BeerSabine E Kulling
Jan 7, 2022·Chemical Research in Toxicology·Tauqeerunnisa Syeda, Jason R Cannon

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