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Protective Effects of [6]-Gingerol Against Chemical Carcinogens: Mechanistic Insights

[6]-Gingerol from ginger has received considerable attention as a potential cancer therapeutic agent because of its chemopreventive and chemotherapeutic effects, as well as its safety. In the current study, we examined [6]-gingerol as a natural scavenger of nine ultimate chemical carcinogens to whic...

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Autores principales: Furlan, Veronika, Bren, Urban
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2020
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7037038/
https://www.ncbi.nlm.nih.gov/pubmed/31973096
http://dx.doi.org/10.3390/ijms21030695
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author Furlan, Veronika
Bren, Urban
author_facet Furlan, Veronika
Bren, Urban
author_sort Furlan, Veronika
collection PubMed
description [6]-Gingerol from ginger has received considerable attention as a potential cancer therapeutic agent because of its chemopreventive and chemotherapeutic effects, as well as its safety. In the current study, we examined [6]-gingerol as a natural scavenger of nine ultimate chemical carcinogens to which we are frequently exposed: glycidamide, styrene oxide, aflatoxin B1 exo-8,9-epoxide, β-propiolactone, ethylene oxide, propylene oxide, 2-cyanoethylene oxide, chloroethylene oxide, and vinyl carbamate epoxide. To evaluate [6]-gingerol efficacy, we expanded our research with the examination of glutathione—the strongest natural scavenger in human cells. The corresponding activation free energies were calculated using Hartree-Fock method with three flexible basis sets and two implicit solvation models. According to our results, [6]-gingerol proves to be an extremely effective scavenger of chemical carcinogens of the epoxy type. On the other hand, with the exception of aflatoxin B1 exo-8,9-epoxide, glutathione represents a relatively poor scavenger, whose efficacy could be augmented by [6]-gingerol. Moreover, our quantum mechanical study of the alkylation reactions of chemical carcinogens with [6]-gingerol and glutathione provide valuable insights in the reaction mechanisms and the geometries of the corresponding transition states. Therefore, we strongly believe that our research forms a solid basis for further computational, experimental and clinical studies of anticarcinogenic properties of [6]-gingerol as well as for the development of novel chemoprophylactic dietary supplements. Finally, the obtained results also point to the applicability of quantum chemical methods to studies of alkylation reactions related to chemical carcinogenesis.
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spelling pubmed-70370382020-03-11 Protective Effects of [6]-Gingerol Against Chemical Carcinogens: Mechanistic Insights Furlan, Veronika Bren, Urban Int J Mol Sci Article [6]-Gingerol from ginger has received considerable attention as a potential cancer therapeutic agent because of its chemopreventive and chemotherapeutic effects, as well as its safety. In the current study, we examined [6]-gingerol as a natural scavenger of nine ultimate chemical carcinogens to which we are frequently exposed: glycidamide, styrene oxide, aflatoxin B1 exo-8,9-epoxide, β-propiolactone, ethylene oxide, propylene oxide, 2-cyanoethylene oxide, chloroethylene oxide, and vinyl carbamate epoxide. To evaluate [6]-gingerol efficacy, we expanded our research with the examination of glutathione—the strongest natural scavenger in human cells. The corresponding activation free energies were calculated using Hartree-Fock method with three flexible basis sets and two implicit solvation models. According to our results, [6]-gingerol proves to be an extremely effective scavenger of chemical carcinogens of the epoxy type. On the other hand, with the exception of aflatoxin B1 exo-8,9-epoxide, glutathione represents a relatively poor scavenger, whose efficacy could be augmented by [6]-gingerol. Moreover, our quantum mechanical study of the alkylation reactions of chemical carcinogens with [6]-gingerol and glutathione provide valuable insights in the reaction mechanisms and the geometries of the corresponding transition states. Therefore, we strongly believe that our research forms a solid basis for further computational, experimental and clinical studies of anticarcinogenic properties of [6]-gingerol as well as for the development of novel chemoprophylactic dietary supplements. Finally, the obtained results also point to the applicability of quantum chemical methods to studies of alkylation reactions related to chemical carcinogenesis. MDPI 2020-01-21 /pmc/articles/PMC7037038/ /pubmed/31973096 http://dx.doi.org/10.3390/ijms21030695 Text en © 2020 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Furlan, Veronika
Bren, Urban
Protective Effects of [6]-Gingerol Against Chemical Carcinogens: Mechanistic Insights
title Protective Effects of [6]-Gingerol Against Chemical Carcinogens: Mechanistic Insights
title_full Protective Effects of [6]-Gingerol Against Chemical Carcinogens: Mechanistic Insights
title_fullStr Protective Effects of [6]-Gingerol Against Chemical Carcinogens: Mechanistic Insights
title_full_unstemmed Protective Effects of [6]-Gingerol Against Chemical Carcinogens: Mechanistic Insights
title_short Protective Effects of [6]-Gingerol Against Chemical Carcinogens: Mechanistic Insights
title_sort protective effects of [6]-gingerol against chemical carcinogens: mechanistic insights
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7037038/
https://www.ncbi.nlm.nih.gov/pubmed/31973096
http://dx.doi.org/10.3390/ijms21030695
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