Abstract Catechin – a natural polyphenol substance – has excellent antioxidant properties for the treatment of diseases, especially for cholesterol lowering. Catechin can reduce cholesterol content in micelles by forming insoluble precipitation with cholesterol, thereby reducing the absorption of cholesterol in the intestine. In this study, to better understand the molecular mechanism of catechin and cholesterol, we studied the interaction between typical catechins and cholesterol by the density functional theory. Results show that the adsorption energies between the four catechins and cholesterol are obviously stronger than that of cholesterol themselves, indicating that catechin has an advantage in reducing cholesterol micelle formation. Moreover, it is found that the molecular interactions of the complexes are mainly due to charge transfer of the aromatic rings of the catechins as well as the hydrogen bond interactions. Unlike the intuitive understanding of a complex formed by hydrogen bond interaction, which is positively correlated with the number of hydrogen bonds, the most stable complexes (epicatechin–cholesterol or epigallocatechin–cholesterol) have only one but stronger hydrogen bond, due to charge transfer of the aromatic rings of catechins.

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用密度泛函理论研究儿茶素与胆固醇的相互作用

摘要 儿茶素是一种天然多酚物质，具有优异的抗氧化特性，可用于治疗疾病，尤其是降低胆固醇。儿茶素能与胆固醇形成不溶性沉淀，降低胶束中的胆固醇含量，从而减少肠道对胆固醇的吸收。本研究为了更好地理解儿茶素与胆固醇的分子机制，我们通过密度泛函理论研究了典型儿茶素与胆固醇的相互作用。结果表明，四种儿茶素与胆固醇之间的吸附能明显强于胆固醇本身，说明儿茶素在降低胆固醇胶束形成方面具有优势。而且，发现配合物的分子间相互作用主要是由于儿茶素芳香环的电荷转移以及氢键相互作用。与通过氢键相互作用形成的复合物的直观理解不同，它与氢键的数量呈正相关，最稳定的复合物（表儿茶素-胆固醇或表没食子儿茶素-胆固醇）只有一个但更强的氢键，这是由于儿茶素的芳香环。