Flavonoids Synthesis Of Sulfonated Derivatives And Its Active Research

With the rapid development of natural product chemistry and organic synthesis, a great number of new compounds were discovered and synthesized. Especially in extracting effective components from plants and modifying them to new kinds of compounds with better clinical efficacy and higher pharmacological activation. This is an effective method to speed up the pace of the modernization of Traditional Chinese Medicine.There are a wide range of physical and chemical properties of flavonoids, which are widely exist in various kinds of medicinal herbs, fruits, and vegetables. Flavonoids can prevent liver from injury, increase vasodilator activity, have effects of antioxidant and antitumor, while have little side effects and significant effect of therapeutic. Thus flavonoids always attract widespread attention. However, due to the special chemical structure, flavonoid has low water solubility, and as a result, its bioavailability is significantly affected. To improve its bioavailability, there are many kinds of methods to be taken. One of the most commonly used methods is transformation of the chemical structure of the nucleus.First of all, in this article, we made a simple statement of the structure, classification, characteristics and application of flavonoids, and have made a summary of domestic and foreign quercetin and baicalein and its derivatives progress. To improve the water solubility, this paper carried out an in-depth study of the law and application of the sulfonation reaction.Secondly, the paper selected a few hot-researched flavonoids, quercetin and baicetin, as the leading compunds, and sodium3,3’,4’,5,7-pentahydroxy-flavone-5’,8-disulfonate (QSNa), sodium5,6,7-trihydroxy-flavonoe-8-sulfonate(BSNa) were synthesized and characterized by infrared spectrometry(IR), nuclear magnetic resonance (NMR), and qualitative analysised by high performance liquid chromatographic(HPLC).Finally, antioxidant and anti-tumor activity in vitro, and animal excretion in vivo of quercetin and baicalein and its sulfonated derivatives were measured. In vitro antioxidant experiment showed that the sulfonated derivatives not only maintain the original activity but also improve some bioavailability. Animal excretion test indicated that the sulfonated derivatives of the cumulative urinary excretion were larger than its original, and the cumulative fecal excretion of the original is greater than the sulfonated derivatives of both. These facts prove that the absorption of sulfonated derivatives is better than their parens. The observed results of cell toxicity test and cell morphology indicated that, in the same concentration, the toxic effects of BSNa on MCF-7cells is deeper than B, and better than5-Fu. In flow cytometry analysis of MCF-7cell cycle distribution, the BSNa inhibits the growth tumor cells in S phase of cell growth, so that the growth of the tumor cells can be kept from the phase of G2/M. In this case, the BSNa could inhibit the growth of tumor cell. Tumor cell apoptosis analysis showed that BSNa could induce tumor cell apoptosis.After the structures of the quercetin and baicalein were modified, their water-soluble and pharmacological activities were both improved, which will provide a theoretical foundation for developing the new drugs.