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Role of Lactone Ring in Structural, Electronic, and Reactivity Properties of Aflatoxin B1: A Theoretical Study

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Abstract

This study involved quantum mechanical calculations to explain the chemical behavior of the lactone ring of aflatoxin B1, which is a carcinogenic hazardous compound. The aflatoxin B1 compound, produced by the fungi Aspergillum flavus, was studied with the B3LYP/6-311+G(d,p) method; its reactivity properties were accounted for by means of the calculated geometrical and electronic parameters. The results obtained indicate that the fused A, B, C, and D rings of aflatoxin adopt a continuous planar conformation. The carbon atom of the lactone group presents a highly electrophilic character, since the population analysis yields a high positive charge for this atom, whereas high negative charges were recorded for both oxygen sites of that group. Thus, in an acidic aqueous medium, the oxygen atoms could be protonated and the carbon site may suffer a nucleophilic attack by water. Accordingly, the OC−O bond length has been lengthened substantially. So it was demonstrated that the lactonic ring of aflatoxin B1 is hydrolyzed under acidic conditions by an acid-acyl bimolecular mechanisms, AAC2, suggesting the deletion of its carcinogenic properties.

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Acknowledgments

We acknowledge financial support from DGAPA-UNAM under Projects PAPIME (PE201905), CONACyT-México, and PACIVE (VIASC-103, FESC-UNAM). Access to the Kan-Balam supercomputer at DGSCA-UNAM is greatly appreciated. We also truly appreciate the valuable discussions with Dra. Rocío Cartas, Dr. Gustavo Rivera, and Dr. Victor Chávez.

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  1. Departamento de Ciencias Químicas, Campo 1, Facultad de Estudios Superiores Cuautitlán, Universidad Nacional Autónoma de México, Cuautitlán Izcalli, C.P. 54740, Estado de México, Mexico

    Inés Nicolás-Vázquez, Abraham Méndez-Albores, Ernesto Moreno-Martínez & René Miranda

  2. Departamento de Física y Química Teórica, DEPg. Facultad de Química, Universidad Nacional Autónoma de México, Del. Coyoacán, C.P. 04510, México D.F., Mexico

    Miguel Castro

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  1. Inés Nicolás-Vázquez
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  2. Abraham Méndez-Albores
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  3. Ernesto Moreno-Martínez
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Correspondence to Inés Nicolás-Vázquez or Miguel Castro.

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Nicolás-Vázquez, I., Méndez-Albores, A., Moreno-Martínez, E. et al. Role of Lactone Ring in Structural, Electronic, and Reactivity Properties of Aflatoxin B1: A Theoretical Study. Arch Environ Contam Toxicol 59, 393–406 (2010). https://doi.org/10.1007/s00244-010-9501-x

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