Structural Properties of Green Tea Catechins
Structural Properties of Green Tea Catechins
复制标题
DOI：
10.1021/acs.jpcb.5b08737
复制
发表时间：
2015-10-08
影响因子：
3.3
通讯作者：
Molteni, Carla
中科院分区：
文献类型：
--
作者：
Botten, Dominic;Fugallo, Giorgia;Molteni, Carla
绿茶儿茶素是一种多酚，被认为对健康有益；它们作为保健补充剂销售，并研究它们对各种医疗状况的潜在影响。然而，它们在分子水平上的作用机制以及与环境的相互作用仍不清楚。在这里，通过原子模拟，我们探索了四种绿茶儿茶素在气相和水溶液中的结构特性：具体来说，最丰富的 (-)-表儿茶素-3-没食子酸酯、(-)-表儿茶素-3-没食子酸酯、(-)-表没食子儿茶素-3-O-(3-O-甲基)-没食子酸酯和 (-)-表没食子儿茶素。我们描述了这些儿茶素在环境条件下的自由能构象景观，作为酚环扭转自由度的函数，确定了稳定的构象异构体及其连接。我们表明，这些自由能景观仅受到与溶剂的相互作用以及多酚环的结构细节的微妙影响。然而，羟基（或其取代基）的数量和位置以及没食子酰基部分的存在/不存在对所选择的儿茶素拯救壳和氢键能力具有显着影响，这最终与它们与生物环境相互作用和影响生物环境的能力有关。
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 salvation shells and hydrogen bond capabilities, which are ultimately linked to their ability to interact with and affect the biological environment.