Publications ( Cited by SCI )

Syntheses and Crystal Structures of [Na(H2O)(1/2)]X and NH2(CH2CH3)(2)X and Antioxidant Activity of the Former

作者: Liu B (Liu Bin)1,2, Yang BL (Yang Bo-Lun)
发表/完成日期: 2009-09-11
期卷: 28( 9)
In order to enhance the water-solubility and biological utilization rate of chrysin, sodium 5,7-dihydroxylflavone-8-sulfonate (1, [Na(H2O)(1/2)]X, X = C15H9O4SO3, 5,7-dihydroxylflavone-8-sulfonate) was synthesized and its structure was identified on the basis of NMR, FT-IR and elemental analysis. The assembly of 5,7-dihydroxylflavone-8-sulfonate with diethylamide cation afforded diethylamide 5,7-dihydroxylflavone-8-sulfonate (2, NH2(CH2CH3)(2)X) which was characterized by FT-IR and elemental analysis. The crystal structures of 1 and 2 were determined by X-ray single-crystal diffraction analysis. The crystal of 1 is of triclinic system, space group P (1) over bar, with a = 8.5628(13), b = 12.8916(19), c = 13.562(2) angstrom, alpha = 82.494(1), beta = 78.601(2), gamma = 84.033(2)degrees, C30H20Na2O15S2, Z = 2, M-r = 730.59, V = 1450.3 (4) angstrom(3), D-c = 1.673 g/cm(3), F(000) = 748, mu = 0.295 mm(-1), the final R = 0.0641 and wR = 0.1458. The crystal of 2 crystallizes in the triclinic system, space group P (1) over bar, with a = 7.689(2), b = 11.184(3), c = 11.734(3) angstrom, alpha = 74.268(3), beta = 81.751(4), gamma = 87.991(3)degrees, C19H21NO7S, Z = 2, M-r = 407.43, V = 961.2(4) angstrom(3), D-c = 1.408 g/cm(3), F(000) = 428, mu = 0.210 mm(-1), the final R = 0.0484 and wR = 0.1195. In 1, the three-dimensional structure is organized into organic and inorganic regions; the flavone skeletons are stacked into organic regions by pi center dot center dot center dot pi stacking interactions; inorganic regions are generated by Na-O coordination bonds among sulfonate groups, coordinated water molecules and Na-I. The sulfonate groups play an important role as a bridge of inorganic and organic regions. One-dimensional chain structure of 2 is extended by N-H center dot center dot center dot O hydrogen bonds and pi center dot center dot center dot pi stacking interactions. Furthermore, the antioxidant activity of 1 was evaluated. The scavenging activity of I to DPPH free radical is better than that of the parent compound chrysin.