title: Association of tannins and related polyphenols with the cyclic peptide gramicidin S.
abstract: The association of 10 different tannins and related polyphenols with gramicidin S, a cyclic peptide having a rigid beta-turn structure, has been examined using 1H-NMR spectroscopy. In the presence of pentagalloylglucose and epigallocatechin-3-O-gallate, the proton signals due to proline and the adjacent phenylalanine moieties selectively shifted to up field, suggesting a regioselective association with the beta-turn structure. The association was also supported by the observation of intermolecular nuclear Overhauser effects between epigallocatechin-3-O-gallate and the peptide. In contrast, ellagitannins, biogenetically derived from pentagalloylglucose, showed small and non-selective chemical shift changes, suggesting that interaction with these tannins is relatively weak. The hydrophobicity of the tannin molecules and the steric hindrance of the interaction site are thought to be important in the association.
authors.affiliation: School of Pharmaceutical Sciences, Nagasaki University, Japan.
authors.forename: Ying-Jun
authors.initials: YJ
authors.lastname: Zhang
authors.forename: Takashi
authors.initials: T
authors.lastname: Tanaka
authors.forename: Yayoi
authors.initials: Y
authors.lastname: Betsumiya
authors.forename: Rie
authors.initials: R
authors.lastname: Kusano
authors.forename: Atsushi
authors.initials: A
authors.lastname: Matsuo
authors.forename: Toshihisa
authors.initials: T
authors.lastname: Ueda
authors.forename: Isao
authors.initials: I
authors.lastname: Kouno
mesh_terms: D005419:Flavonoids; D006096:Gramicidin / Q000737:chemistry*; D057927:Hydrophobic and Hydrophilic Interactions; D010636:Phenols / Q000737:chemistry*; D011108:Polymers / Q000737:chemistry*; D059808:Polyphenols; D013634:Tannins / Q000737:chemistry*
chemical_list: D005419:Flavonoids; D010636:Phenols; D011108:Polymers; D059808:Polyphenols; D013634:Tannins; D006096:Gramicidin