title: Tannins and Tannin-Related Derivatives Enhance the (Pseudo-)Halogenating Activity of Lactoperoxidase.
abstract: Several hydrolyzable tannins, proanthocyanidins, tannin derivatives, and a tannin-rich plant extract of tormentil rhizome were tested for their potential to regenerate the (pseudo-)halogenating activity, i.e., the oxidation of SCN-to hypothiocyanite-OSCN, of lactoperoxidase (LPO) after hydrogen peroxide-mediated enzyme inactivation. Measurements were performed using 5-thio-2-nitrobenzoic acid in the presence of tannins and related substances in order to determine kinetic parameters and to trace the LPO-mediated-OSCN formation. The results were combined with docking studies and molecular orbital analysis. The-OSCN-regenerating effect of tannin derivatives relates well with their binding properties toward LPO as well as their occupied molecular orbitals. Especially simple compounds like ellagic acid or methyl gallate and the complex plant extract were found as potent enzyme-regenerating compounds. As the (pseudo-)halogenating activity of LPO contributes to the maintenance of oral bacterial homeostasis, the results provide new insights into the antibacterial mode of action of tannins and related compounds. Furthermore, chemical properties of the tested compounds that are important for efficient enzyme-substrate interaction and regeneration of the-OSCN formation by LPO were identified.
authors.affiliation: Institute for Medical Physics and Biophysics, Medical Faculty, University of Leipzig , Härtelstraße 16-18, 04107 Leipzig, Germany.
authors.forename: Jana
authors.identifier: 0000-0002-5000-7919
authors.initials: J
authors.lastname: Gau
authors.forename: Martine
authors.initials: M
authors.lastname: Prévost
authors.forename: Pierre
authors.initials: P
authors.lastname: Van Antwerpen
authors.forename: Menyhárt-Botond
authors.identifier: 0000-0003-4222-0717
authors.initials: MB
authors.lastname: Sarosi
authors.forename: Steffen
authors.initials: S
authors.lastname: Rodewald
authors.affiliation: Institute for Medical Physics and Biophysics, Medical Faculty, University of Leipzig , Härtelstraße 16-18, 04107 Leipzig, Germany.
authors.forename: Jürgen
authors.initials: J
authors.lastname: Arnhold
authors.affiliation: Institute for Medical Physics and Biophysics, Medical Faculty, University of Leipzig , Härtelstraße 16-18, 04107 Leipzig, Germany.
authors.forename: Jörg
authors.initials: J
authors.lastname: Flemmig
mesh_terms: D054879:Halogenation; D006861:Hydrogen Peroxide / Q000737:chemistry / Q000378:metabolism*; D047348:Hydrolyzable Tannins / Q000737:chemistry / Q000302:isolation & purification*; D007700:Kinetics; D007784:Lactoperoxidase / Q000737:chemistry / Q000378:metabolism*; D015394:Molecular Structure; D009579:Nitrobenzoates / Q000737:chemistry / Q000302:isolation & purification*; D010084:Oxidation-Reduction; D010936:Plant Extracts / Q000737:chemistry / Q000302:isolation & purification*; D044945:Proanthocyanidins / Q000737:chemistry / Q000302:isolation & purification*; D027343:Rhizome / Q000378:metabolism*; D013438:Sulfhydryl Compounds / Q000737:chemistry / Q000302:isolation & purification*; D013634:Tannins / Q000737:chemistry / Q000302:isolation & purification*; D013861:Thiocyanates / Q000737:chemistry / Q000302:isolation & purification*
chemical_list: D047348:Hydrolyzable Tannins; D009579:Nitrobenzoates; D010936:Plant Extracts; D044945:Proanthocyanidins; D013438:Sulfhydryl Compounds; D013634:Tannins; D013861:Thiocyanates; C011136:thionitrobenzoic acid; C014607:hypothiocyanite ion; D006861:Hydrogen Peroxide; D007784:Lactoperoxidase