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The antioxidant capacity of an imidazole alkaloids family through single-electron transfer reactions

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Abstract

The single-electron transfer (SET) reactions from the neutral and mono-anion species of five imidazole alkaloids (lepidines A, B, C, D, and E) against hydroperoxyl radicals have been studied using the density functional theory and the Marcus theory. The deprotonated species of three alkaloids were found to have free radical scavenging activity. The antioxidant activity was studied via single-electron transfer (SET) under physiological conditions. The SET reactions for lepidines B, D, and E were found to have rate constants ranging from 105 to 106 M−1 s−1. Therefore, they are predicted to be able to deactivate hydroperoxyl radicals and therefore the damage caused by them to polyunsaturated fatty acids. It is important to mention that the acid-base equilibrium plays an important role in their free radical scavenging activity.

Lepidines are predicted to be able to deactivate hydroperoxyl radicals and the damage caused by them to polyunsaturated fatty acids.

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Acknowledgments

E. G.-H. acknowledges the computing time granted by LANCAD-CONACYT and TecNM (8338.20-PD) by the funding. The authors thank Laboratorio de Visualización y Cómputo en Paralelo at the UAM - Iztapalapa for the access to its computer facilities. A. P.-G. acknowledges the Program of Cátedras - CONACYT from CONACYT - UAMI (2015‑2025), ID-Investigador 435. E. C.-A. acknowledges the support given by the National Laboratory Supercomputing Southeast housed in the BUAP and by the high-performance computing system of PIDi-UTEM (SCC-PIDi-UTEM FONDEQUIP-EQM180180).

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Authors and Affiliations

  1. CONACYT – Universidad Autónoma Metropolitana – Iztapalapa, San Rafael Atlixco 186, Col. Vicentina Iztapalapa, C. P. 09340, Ciudad de México, México

    Adriana Pérez-González

  2. Departamento de Posgrado e Investigación, División de Mecatrónica, Instituto Tecnológico Superior de Zacapoaxtla, Zacapoaxtla Puebla, México

    Erwin García-Hernández

  3. Benemérita Universidad Autónoma de Puebla, Facultad de Ingeniería Química, Ciudad Universitaria, Puebla, México

    Ernesto Chigo-Anota

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  1. Adriana Pérez-González
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Correspondence to Adriana Pérez-González or Erwin García-Hernández.

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Pérez-González, A., García-Hernández, E. & Chigo-Anota, E. The antioxidant capacity of an imidazole alkaloids family through single-electron transfer reactions. J Mol Model 26, 321 (2020). https://doi.org/10.1007/s00894-020-04583-2

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