Synthesis and Characterization of a Flavonoid Chrysin Derivative
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Suya Gao, Yun Zhang, Li Wang, Yimei Tang, Benquan Hu, Han Zhang
Chrysin, was also known as 5,7-dihydroxyl flavone, with many different biological activities such as antioxidant, antiviral, antidiabetic, and anti-anxiety, etc. A chrysin derivative, 5,7-dihydroxyflavone-8-sulfonate potassium, was synthesized by sulfonation reaction under room temperature to improve its water-solubility and bioavailability. And the derivative was investigated by elemental analysis, nuclear magnetic resonance (NMR) and X-ray single-crystal diffraction, respectively. The crystal structure analysis shows that 5,7-dihydroxyflavone- 8-sulfonate potassium belongs to orthorhombic system. In its crystal structure, sulfonate oxygen atoms and flavone carbonyl oxygen atoms coordinate with potassium ions, and K-O coordination forms a one-dimensional polyionic chain. There’s π···π stacking interaction between the adjacent flavonoid skeletons. The self-assembly of the compound into a three-dimensional supramolecular structure was performed by π···π stacking and K-O coordination. Meanwhile, the interaction between the compound and calf thymus DNA (ct-DNA) was investigated by fluorescence spectrometry, and the results showed that the interaction between the derivative and DNA was stronger than that of the chrysin.
Chrysin, Synthesis, Crystal structure, CT-DNA