Computational Examination of Urolithins as Potential Scavengers of Chemical Carcinogens

Tannins represent a rather diverse group of natural compounds that are of great technological importance while they might also exhibit some health beneficial properties [1]. Ellagic acid is a hydrolysis product of ellagitannins and has been subjected to several studies [2]. In our previous study, we demonstrated that ellagic acid forms a promising candidate for carcinogen scavenging [3]. However, its activity in the organism is limited by its rather low bioavailability. Because of this, it may act as a carcinogen scavenger in the digestive tract, while its activity in the cells is limited by pharmacokinetics. However, ellagic acid is by bacteria in the digestive tract metabolized into several urolithins, which can later be observed in various body fluids [4].

In this study, the chemical scavenging capacity of several urolithins (e.g., Urolithin B and A, Isourolithin A, and Urolithin AR) against nine ultimate carcinogens of the epoxy type at the Hartree-Fock and B3LYP levels of theory in conjunction with flexible basis sets and implicit solvation models were examined. The reactivities of ultimate carcinogens were additionally compared to the reactivity of ellagic acid and guanine, the most reactive nucleobase of DNA, against the same set of carcinogens [3], [5].

Fig. 1 Schematic representation of a reaction between vinyl carbamate and Urolithin A.

 

MissingLinkText

• References

• 1 Pizzi A. Tannins medical/pharmacological and related applications: A critical review. Sustain Chem Pharm 2021; 22: 100481
• 2 Hostnik G, Tošović J, Štumpf S. et al. The influence of pH on UV/Vis spectra of gallic and ellagic acid: A combined experimental and computational study. Spectrochim Acta A Mol Biomol Spectrosc 2022; 267: 120472
• 3 Hostnik G, Gladović M, Bren U. Tannin Basic Building Blocks as Potential Scavengers of Chemical Carcinogens: A Computational Study. J Nat Prod 2019; 82: 3279-3287
• 4 García-Vilalba R, Selma MV, Espín JC, Tomás-Barberán F. Identification of novel Urolithin Metabolites in Human Feces and Urine after the Intake of a Pomegranate Extract. J Agric Food Chem 2019; 67: 11099-11107
• 5 Gladović M, Španinger E, Bren U. Nucleic Bases Alkylation with Acrylonitrile and Cyanoethylene Oxide: A Computational Study. Chem Res Toxicol 2018; 31: 97-104

Publication History

Article published online:
12 December 2022