Studies On Synthesis Of New Flavonoid Vinyl Ether Derivatives And Flavonoid Glycoconjugate From Hesperidin

Flavonids are widely distriuted through the plant medicament,which possess a wide range of pharmacological properties including antivascular-disease activity, antiinfective and antifertility activity, anticarcinogenic activity, antiviral activity, antioxidant effect.The immediate family members of flavonoids include flavones, chalcones, flavanones, and flavonols.In order to further research the biologial activities of this class compounds and meet the need of new drug development, we would like to synthesize new type flavaonoid viny ether derivaties and flavone glycoconjugate.Five key intermediates, hesperetin, persicogenin, dehypersicogenin, diometin and luteolin were synthesized from hesperidin, through hydrolyzation, methyllation, dehydrogenation.These five compounds reacted with trans,trans-farnesyl bromide or prenyl bromide, which synthesized eight new flavonoids, including (1g～1j). 3-bromoflavone (1d) was synthesized from hesperidin, through dehydrogenation hydrolyzation, demethyllation, acetylation, bromination.Flavonol (2d) were synthesized from hesperidin using two different methods.Flavonol (2d) were synthesized from hesperidin, through hydrolyzation, benzylation, AFO reaction. The synthesis method was better than other methods with simple operation, but the relatively lower production rate. The synthesis method was zhe best one not only with the low producing cost and simple operation, but also with the relatively higher production rate and receiving a lot of flavonol. Flavonol (2d) were synthesized from hesperidin, through hydrolyzation, dehydrogenation, benzylation, oxidation with superoxide.Flavonol-O-acetyl glucosides were synthesized by the flavonol (2d). Acetylbromide lactose as glycosyl donor, using tetrabutylammonium bromide (TBBA) as phase transfer catalyst, the reaction was taken under the mild reaction conditions in alkaline baking soda of the water/ dichloromethane system. Acetyl bromide glucose, maltose acetyl bromide as glycosyl donor, which were synthesized to azide sugar. Flavonol (2d) reacted with bromoallylene, synthesized alkynyl flavonol. With two-phase systems flavonol glucoside and glycoconjugate (2h, 2i, 2k, 2n) were synthesized in this study. These compounds have been not reported in literatures until now.The synthetic compounds structure has been confirmed by 1H NMR, MS and IR.