Studies On Synthesis Of Bioactive Flavonols And Their Glycoconjugates From Naringin

Flavonoids is a kind of important natural products and also one of the main activeingredients of medicinal plants. Because of their unique chemical structures, Flavonoids playan important role in the field of antitumor, antiviral, and enzyme inhibitors, and also areimportant drug precursors. To obtain better bioactive precursors of flavonoids, we focused onthe modificating of the Flavonoids’ structures. The main contents of the article were asfollows:1) Using naringin as starting material, two natural flavonols5a and6b were semi-synthesized by the reaction steps of glycoside hydrolysis, dehydrogenation, hydroxylmethylation, benzyl protection, DMDO oxidation and debenzylation. Besides, we discussedthe improvements of the DMDO reaction, which increased the yield of systhesising flavonols.2) Using naringin as starting material, the aurones10was semisynthesized by thereaction steps of glycoside hydrolysis, O-methylation, cyclization being chalcone,Algar-Flynn-Oyamada reaction and debenzylation. The compound10weren’t reported in theliteratures before.3) Two flavonols (5a、6b) substituted with alkynyl group were attached by carbohydratecompounds substituted with N3group using “Click Chemestry” method and obtained a seriesof compounds (12a-23a,12b-23b) which weren’t yet reported in the literatures.4) All of the synthesized compounds have been confirmed by1H NMR, MS and IR.5) Selecting the leukemia cell line, hepatocellular carcinoma cell line, lung cancer celllines, breast cancer cell lines and colon cancer cell line as target cells, the tumor cell activityof synthesized compounds was measured using MTT method. The experimental resultsshowed that the compound15a has certain cytotoxicity on the HL-60and MCF-7cells,the IC50values is31.4μg/ml and15.9μg/ml, respectively.