Structural studies of homoisoflavonoids: NMR spectroscopy, X-ray diffraction, and theoretical calculations

被引:10
作者
Sievanen, Elina [1 ,2 ]
Tousek, Jaromir [1 ]
Lunerova, Kamila [3 ]
Marek, Jaromir [4 ]
Jankovska, Dagmar [3 ]
Dvorska, Margita [3 ]
Marek, Radek [1 ]
机构
[1] Masaryk Univ, Natl Ctr Biomol Res, CZ-62500 Brno, Czech Republic
[2] Univ Jyvaskyla, Dept Chem, FIN-40014 Jyvaskyla, Finland
[3] Univ Vet & Pharmaceut Sci, Fac Pharm, Dept Nat Drugs, CZ-61242 Brno, Czech Republic
[4] Masaryk Univ, Lab Funct Genom & Prote, CZ-62500 Brno, Czech Republic
基金
芬兰科学院;
关键词
Homoisoflavonoid; X-ray diffraction; NMR chemical shift; Molecular modeling; Conformational search; DFT/GIAO NMR shielding; CHEMICAL-SHIFTS; COMPUTATION; H-1;
D O I
10.1016/j.molstruc.2010.06.021
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
In this article we present a detailed structural investigation for five homoisoflavonoids, molecules important from the pharmacological point of view. For studying the electron distribution as well as its influence on the physicochemical properties, NMR spectroscopy, X-ray diffraction, and theoretical calculations have been used. Nuclear magnetic shieldings obtained by using DFT calculations for optimized molecular geometries are correlated with the experimentally determined chemical shifts. The theoretical data are well in agreement with the experimental values. The single crystal X-ray structures of homoisoflavonoid derivatives 1, 3, and 4 have been solved. The molecular geometries and crystal packing determined by X-ray diffraction are used for characterizing the intermolecular interactions. Electron distribution is crucial for the stability of radicals and hence the antioxidant efficiency of flavonoid structures. The hydrogen bonding governs the formation of complexes of homoisoflavonoids with biological targets. (C) 2010 Elsevier B.V. All rights reserved.
引用
收藏
页码:172 / 179
页数:8
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