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Author:

Liu Bin (Liu Bin.) | Yang Bo-Lun (Yang Bo-Lun.) (Scholars:杨伯伦)

Indexed by:

SCIE CSCD

Abstract:

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.

Keyword:

5,7-dihydroxylflavone-8-sulfonate crystal structure DPPH free radical scavenging activity spectroscopic property

Author Community:

  • [ 1 ] [Liu Bin; Yang Bo-Lun] Xi An Jiao Tong Univ, Dept Chem Engn, Xian 710049, Peoples R China
  • [ 2 ] [Liu Bin] Xianyang Normal Univ, Dept Chem, Xianyang 712000, Peoples R China

Reprint Author's Address:

  • 杨伯伦

    Xi An Jiao Tong Univ, Dept Chem Engn, Xian 710049, Peoples R China.

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Source :

CHINESE JOURNAL OF STRUCTURAL CHEMISTRY

ISSN: 0254-5861

Year: 2009

Issue: 9

Volume: 28

Page: 1112-1120

0 . 5 4 4

JCR@2009

0 . 8 9 3

JCR@2020

ESI Discipline: CHEMISTRY;

JCR Journal Grade:4

CAS Journal Grade:4

Cited Count:

WoS CC Cited Count: 2

SCOPUS Cited Count:

ESI Highly Cited Papers on the List: 0 Unfold All

WanFang Cited Count: -1

Chinese Cited Count: -1

30 Days PV: 6

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