Tannin Basic Building Blocks as Potential Scavengers of Chemical Carcinogens: A Computational Study

Abstract

Tannins are natural compounds that have historically been used in the tanning of leather. In the scientific literature, one finds many reports of their possible beneficial health effects, although these are not always unequivocally confirmed. In order to gain a better insight into their proposed anticancer potential, we studied the scavenging capacity of the basic tannin building blocks against various chemical carcinogens of the epoxy type. The reactivity of gallic acid, ellagic acid, and epicathechin was examined using quantum mechanical calculations at the Hartree−Fock level of theory in conjunction with flexible basis sets and implicit solvation models. The monomeric tannin building blocks exhibited significant scavenging potential, with epicatechin presenting the best scavenger, thus encouraging and guiding future experimental studies of their anticarcinogenic properties.

Calculating Entropies of Large Molecules in Aqueous Phase

“…This method has been implemented in a program called ChemSol version 2.1, 25,26,31 which is popular in the biochemical field and has been employed in recent studies. 32,33 A similar electrostatic solvation model by Marenich et al uses a dielectric medium for the solvent while the solute molecules are defined using the complete electron density (no partial charges) and surface tension at its boundary. 34 In this study, we investigate methods of calculating entropy when extending entropy models to large solute molecule systems with a focus on Garza's most recent solvation model.…”

Antioxidative Action of Ellagic Acid—A Kinetic DFT Study

“…In many epidemiological and experimental studies, anticarcinogenic, anti-inflammatory, antiviral, antibacterial, anti-atherosclerosis, antihypertensive, antihyperglycemic, cardioprotective and anti-fibrosis actions of EA have been demonstrated [ 5 , 6 , 7 , 8 , 9 , 10 , 11 ]. It can inhibit carcinogenesis by occupying sites (i.e., microsomal P -450 enzymes, glutathione-S -transferase or DNA), that would normally interact with ultimate carcinogens, through several mechanisms [ 12 , 13 ]. The anticarcinogenic effect of ellagic acid has been studied in various cancer cells.…”

Carcinogenesis of β-Propiolactone: A Computational Study

“…As glutathione represents not only the crucial low molecular weight redox buffer that shields nuclear processes against oxidative stress but also a flexible regulator of genetic and epigenetic functions, it could in certain cellular conditions as well happen that the concentration of free glutathione would be too low to sufficiently protect the genetic material. It would, therefore, be sensible to explore using identical computational methodology also other potential natural scavengers for example from the family of polyphenols − that could provide additional protection from BPL and related carcinogenic agents. This could lead to the discovery of novel anticancer drugs that could effectively prevent carcinogenesis.…”