Study On The Synthetic Method And Estrogenic Activity Of Prenylflavonoids

Flavonoids , naturally occurring plant products, when consumed medicinally have mild if any side -effects and are, therefore, referred to as "tender drugs". Now there are about 4000 naturally occurring compounds that are ubiquitous in all vascular. Prenylated flavonoids are a unique class of naturally occurring flavonoids characterized by the presence of a prenylated side chain (i.e., prenyl, geranyl) in the flavonoid skeleton. Existing in various traditional medicinal plants, prenylated exist a wide range of interesting physiological properties(i.e., hypotensive, antifungal, antibacterial, antitumor, and antiHIV). Now, the separation, synthesis, and research of biological activity have become the hot point of pharmaceutical region. Therefore, the research of synthetic method of flavonoids has the important value of scholarship and application.For further research the biological activity of flavonoids, we researched the synthetic methods of six Prenylated flavonoids (bavachin, isobavachin, 8-prenylna-ringenin, 8-C-prenyl-7,4'-Dihydroxyflavone, 8-C-prenylapigenin, noranhydroicaritin) and successfully synthesized five compounds(bavachin, isobavachin, 8-prenylna-ringenin, 8-C-prenyl-7,4'-Dihydroxyflavone, 8-C-prenylapigenin). The synthetic research of noranhydroicaritin is still being carrying.Bavachin, isobavachin, 8-prenylnaringenin were synthesized in five steps through prenylation, protection of hydroxyl group, condensation, cyclization, deprotection, from p-resacetophenone or 2,4,6-trihydroxyacetophenoneas a starting material.8-C-prenyl-7, 4'-Dihydroxyflavone, 8-C-prenylapigenin were synthesized by dehydrogenation of corresponding prenylflavanones in I2/Pridine.The synthetic method of noranhydroicaritin mainly involves Claisen rearrangement.The compounds of bavachin, isobavachin, 8-C-prenyl-7,4'-Dihydroxyfiavone and 8-C-prenylapigenin were evaluated for their estrogenic activity on sensitivehuman mammary cancer in MCF-7 cell culture. The results showed they all had estrogenic activity in MCF-7 cell culture. Thereinto isobavachin showed the potentest activity.