| Chrysin is a5,7-hydroxyl-flavone extracted from bignoniaceae oroxylin that have shown beneficial health effects by displaying antioxidant, antiviral, anti-allergic, anti-inflammatory, anti-anxiety and anti-thrombotic activities and anti-toumor. Especially the antitumor activity, has become a hot research. But structure determines the chrysin is a kind of amphoteric compounds, the water-soluble and fat-soluble are both low, limiting the role of the play. So my studies have focused on increasing chrysin fat-soluble, this paper hope to start from the increase the fat soluble, trying to find a new way of derivatization.In this paper, eight compounds containing ethyl diacetate chrysin (2), dicarboxymethyl chrysin (3), bisbenzyl chrysin (4), benzyl chrysin (5), diacetyl chrysin (6), monoacetylated chrysin (7),5-ethyl acetate,7-phenylmethyl chrysin (8), and carboxymethyl chrysin(9) were prepared by modification to two hydroxy simultaneously or a single followed by acetylation, benzoyl, carboxylation. The samples after detected by thin-layer chromatography (TLC) were purified through silica gel column. The purified fractions were identified and characterized with MS and NMR.The antitumor activities of these derivatives were analyzed by MTT. Compared with chrysin, the inhibition to H22tumor cells of diacetyl chrysin (3) exhibited a significant increase to91.56%, and its IC50reached141μM. The antitumor activities of the rest compounds decreased in different degree, suggesting that5,7-hydroxyl groups were not the active site of chrysin.Each group was analyzed by flow cytometry to determine their cell cycles. The result showed that the cell cycles of the. control group and the chrysin group did not exhibit any obvious changes different from that of the compound3group. The number of cells at G2/M phases increased largely, while cells of G1and S phase reduced significantly. The result shows that the compound3play the role of inhibition of tumor cell proliferation through the influence of cell cycle. |
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