Structure and Oxidation of Pyrrole Adducts Formed between Aflatoxin B2a and Biological Amines

Chemical Research in Toxicology
Blake R Rushing, Mustafa I Selim

Abstract

Aflatoxin B2a has been shown to bind to proteins through a dialdehyde intermediate under physiological conditions. The proposed structure of this adduct has been published showing a Schiff base interaction, but adequate verification using structural elucidation instrumental techniques has not been performed. In this work, we synthesized the aflatoxin B2a amino acid adduct under alkaline conditions, and the formation of a new product was determined using high performance liquid chromatography-time-of-flight mass spectrometry. The resulting accurate mass was used to generate a novel proposed chemical structure of the adduct in which the dialdehyde forms a pyrrole ring with primary amines rather than the previously proposed Schiff base interaction. The pyrrole structure was confirmed using 1H, 13C, correlation spectroscopy, heteronuclear single quantum correlation, and heteronuclear multiple bond correlation NMR and tandem mass spectrometry. Reaction kinetics show that the reaction is overall second order and that the rate increases as pH increases. Additionally, this study shows for the first time that aflatoxin B2a dialdehyde forms adducts with phosphatidylethanolamines and does so through pyrrole ring formation, which makes it ...Continue Reading

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Citations

Oct 2, 2019·International Journal of Environmental Research and Public Health·Noreddine Benkerroum
Jan 16, 2020·International Journal of Environmental Research and Public Health·Noreddine Benkerroum
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Aug 11, 2021·Food Additives & Contaminants. Part A, Chemistry, Analysis, Control, Exposure & Risk Assessment·Hongwei GuoXiaofei Hu
Aug 27, 2021·Journal of Fungi·Rahim KhanNik Iskandar Putra Samsudin
Mar 26, 2021·Acta Veterinaria Hungarica·Benjámin KövesiKrisztián Balogh

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