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Open AccessArticle

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

by Veronika Furlan 1 and Urban Bren 1,2,*
Faculty of Chemistry and Chemical Technology, University of Maribor, Smetanova 17, SI-2000 Maribor, Slovenia
National Institute of Chemistry, Hajdrihova 19, SI-1001 Ljubljana, Slovenia
Author to whom correspondence should be addressed.
Int. J. Mol. Sci. 2020, 21(3), 695;
Received: 6 December 2019 / Revised: 18 January 2020 / Accepted: 20 January 2020 / Published: 21 January 2020
[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. View Full-Text
Keywords: [6]-gingerol; glutathione; chemical carcinogens of the epoxy type; carcinogenesis; activation free energies; quantum-mechanical calculations [6]-gingerol; glutathione; chemical carcinogens of the epoxy type; carcinogenesis; activation free energies; quantum-mechanical calculations
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Furlan, V.; Bren, U. Protective Effects of [6]-Gingerol Against Chemical Carcinogens: Mechanistic Insights. Int. J. Mol. Sci. 2020, 21, 695.

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