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通过核磁共振和傅里叶变换红外光谱法对反式白藜芦醇(反式-3,5,4'-三羟基二苯乙烯)在溶液中的堆积相互作用研究。

Stacking interaction study of trans-resveratrol (trans-3,5,4'-trihydroxystilbene) in solution by Nuclear Magnetic Resonance and Fourier Transform Infrared Spectroscopy.

作者信息

Bonechi Claudia, Martini Silvia, Magnani Agnese, Rossi Claudio

机构信息

Department of Chemical & Biosystem Sciences, University of Siena, Via Aldo Moro, 2 - 53100 Siena, Italy.

出版信息

Magn Reson Chem. 2008 Jul;46(7):625-9. doi: 10.1002/mrc.2217.

DOI:10.1002/mrc.2217
PMID:18324741
Abstract

Interactions between aromatic rings or other unsaturated systems, including pi-stacking and face-to-edge complexes, are the origin of many phenomena in both organic and biological chemistry. It is well known that these interactions play an important role in the stabilization of the stereo-structure of DNA and the tertiary structure of many proteins.Trans-resveratrol (trans-3,5,4'-trihydroxystilbene, trans-RSV) is a phytoalexin found in Vitis sp. and in many other plants and food products and has received much attention because of its possible positive health benefits. In this work, the pi-stacking interaction of trans-RSV was studied by nuclear magnetic resonance (NMR) and Fourier transform infrared (FTIR) spectroscopy. In particular, the proton chemical shift dependence of the RSV concentration in the range 2 x 10(-2) - 1 x 10(-5) M and temperature were analysed. Moreover, the dynamics of the supramolecular aggregates were studied by nuclear spin relaxation data.

摘要

芳香环或其他不饱和体系之间的相互作用,包括π-堆积和面对面边缘复合物,是有机化学和生物化学中许多现象的起源。众所周知,这些相互作用在DNA立体结构和许多蛋白质三级结构的稳定中起着重要作用。反式白藜芦醇(反式-3,5,4'-三羟基芪,反式-RSV)是一种在葡萄属植物以及许多其他植物和食品中发现的植保素,因其可能对健康有益而备受关注。在这项工作中,通过核磁共振(NMR)和傅里叶变换红外(FTIR)光谱研究了反式-RSV的π-堆积相互作用。特别分析了RSV浓度在2×10⁻² - 1×10⁻⁵ M范围内的质子化学位移依赖性以及温度。此外,通过核自旋弛豫数据研究了超分子聚集体的动力学。

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