title: Structural Properties of Green Tea Catechins.
abstract: Green tea catechins are polyphenols which are believed to provide health benefits; they are marketed as health supplements and are studied for their potential effects on a variety of medical conditions. However, their mechanisms of action and interaction with the environment at the molecular level are still not well-understood. Here, by means of atomistic simulations, we explore the structural properties of four green tea catechins, in the gas phase and water solution: specifically, (-)-epigallocatechin-3-gallate, which is the most abundant, (-)-epicatechin-3-gallate, (-)-epigallocatechin-3-O-(3-O-methyl)-gallate, and (-)-epigallocatechin. We characterize the free energy conformational landscapes of these catechins at ambient conditions, as a function of the torsional degrees of freedom of the pholyphenolic rings, determining the stable conformers and their connections. We show that these free energy landscapes are only subtly influenced by the interactions with the solvent and by the structural details of the polyphenolic rings. However, the number and position of the hydroxyl groups (or their sustituents) and the presence/absence of the galloyl moiety have significant impact on the selected catechin solvation shells and hydrogen bond capabilities, which are ultimately linked to their ability to interact with and affect the biological environment.
authors.affiliation: Physics Department, King's College London , Strand, London WC2R 2LS, United Kingdom.
authors.forename: Dominic
authors.initials: D
authors.lastname: Botten
authors.affiliation: Laboratoire des Solides Irradiés, École Polytechnique , 91128 Palaiseau Cedex, France.
authors.forename: Giorgia
authors.initials: G
authors.lastname: Fugallo
authors.affiliation: Randall Division of Cell and Molecular Biophysics, King's College London , Guy's Campus, London SE1 1UL, United Kingdom.
authors.forename: Franca
authors.initials: F
authors.lastname: Fraternali
authors.affiliation: Physics Department, King's College London , Strand, London WC2R 2LS, United Kingdom.
authors.forename: Carla
authors.initials: C
authors.lastname: Molteni
mesh_terms: D002392:Catechin / Q000737:chemistry*; D056004:Molecular Dynamics Simulation; D015394:Molecular Structure; D013662:Tea / Q000737:chemistry*
chemical_list: D013662:Tea; D002392:Catechin