Natural Chemistry Research Group, Department of Chemistry, University of Turku, FI-20014 Turku, Finland.
Molecules. 2021 Jan 12;26(2):373. doi: 10.3390/molecules26020373.
Ellagitannins have antimicrobial activity, which might be related to their interactions with membrane lipids. We studied the interactions of 12 different ellagitannins and pentagalloylglucose with a lipid extract of by high-resolution magic angle spinning NMR spectroscopy. The nuclear Overhauser effect was utilized to measure the cross relaxation rates between ellagitannin and lipid protons. The shifting of lipid signals in 1H NMR spectra of ellagitannin-lipid mixture due to ring current effect was also observed. The ellagitannins that showed interaction with lipids had clear structural similarities. All ellagitannins that had interactions with lipids had glucopyranose cores. In addition to the central polyol, the most important structural feature affecting the interaction seemed to be the structural flexibility of the ellagitannin. Even dimeric and trimeric ellagitannins could penetrate to the lipid bilayers if their structures were flexible with free galloyl and hexahydroxydiphenoyl groups.
鞣花单宁具有抗菌活性，这可能与其与膜脂质的相互作用有关。我们通过高分辨率魔角旋转 NMR 光谱研究了 12 种不同的鞣花单宁和五没食子酰葡萄糖与 的脂质提取物之间的相互作用。利用核 Overhauser 效应测量了鞣花单宁和脂质质子之间的交叉弛豫率。还观察到由于环电流效应，在鞣花单宁-脂质混合物的 1H NMR 光谱中脂质信号的移动。与脂质相互作用的鞣花单宁具有明显的结构相似性。所有与脂质相互作用的鞣花单宁都具有葡萄糖吡喃糖核。除了中心多元醇外，影响相互作用的最重要结构特征似乎是鞣花单宁的结构灵活性。即使是二聚体和三聚体鞣花单宁，如果其结构具有游离的没食子酰和六羟基二苯甲酰基，也可以穿透脂质双层。
