Planta Med 2019; 85(18): 1550
DOI: 10.1055/s-0039-3400093
Main Congress Poster
Poster Session 2
© Georg Thieme Verlag KG Stuttgart · New York

Tannin basic building blocks as potential scavengers of chemical carcinogens: a computational study

G Hostnik
1   University of Maribor,, Faculty of Chemistry and Chemical Technology, Smetanova 17, SI-2000 Maribor, Slovenia
,
M Gladović
1   University of Maribor,, Faculty of Chemistry and Chemical Technology, Smetanova 17, SI-2000 Maribor, Slovenia
,
U Bren
1   University of Maribor,, Faculty of Chemistry and Chemical Technology, Smetanova 17, SI-2000 Maribor, Slovenia
2   National Institute of Chemistry,, Hajdrihova 19, SI-1001 Ljubljana, Slovenia
› Author Affiliations
Further Information

Publication History

Publication Date:
20 December 2019 (online)

 

Tannins are natural compounds that were historically used in the tanning of leather. This structurally rather diverse group is divided into hydrolysable (gallotannins and ellagitannins), complex and condensed tannins.[1] Since they are omnipresent in various plant tissues, they also represent a common component of food (e.g. ellagitannins in berries, epigallocatechin in green tea). Tannins are believed to exert several health enhancing effects,[2] although those effect are rather difficult to study.[3] Therefore computational studies can provide us with some guidance of possible molecular mechanisms of tannin actions.

In this study we examined chemical scavenging capacity of three tannin basic building blocks (i.e. gallic acid, ellagic acid and (-)-epicatechin) against nine ultimate carcinogens of the epoxy type at the Hartree-Fock level of theory in conjunction with flexible basis sets and implicit solvation models. The reactivity of tannin basic building blocks was then compared to the reactivity of identical ultimate carcinogens against guanine, which represents the most reactive nucleobase of DNA.[4] The tannin basic building blocks with reactivity towards ultimate carcinogens that exceeds the reactivity of guanine were presumed as good scavengers of ultimate carcinogens. The studied monomeric tannin building blocks exhibit a significant scavenging potential, with (-)-epicatechin representing the best scavenger.

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Fig. 1
 

  • References

  • 1 Khanbabaee K, van Ree T. Tannins: Classification and Definition. Nat. Prod. Rep. 2001; 18: 641-649.
    CrossrefPubMedGoogle Scholar
  • 2 Serrano J, Puupponen-Pimiä R, Dauer A, . Aura A.-M, Tannins SCF. : Current knowledge of food sources, intake, bioavailability and biological effects. Mol. Nutr. Food Res. 2009; 53: S310-S329.
    CrossrefPubMed
  • 3 Sauer S, Plauth A. Health-beneffcial nutraceuticals-myth or reality? Appl. Micro-biol. Biotechnol. 2017; 101: 951—961.
    PubMedGoogle Scholar
  • 4 Gladović M, Španinger E, Bren U. Nucleic Bases Alkylation with Acrylonitrile and Cyanoethylene Oxide: A Computational Study. Chem. Res. Toxicol. 2018; 31: 97-104.
    CrossrefPubMedGoogle Scholar