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目的为改善黄芩苷的溶解性,设计合成系列黄芩苷衍生物,并评价其抗脂质过氧化活性和抗肿瘤活性。方法以黄芩苷和环氧乙(丙)烷为原料,通过羟乙基化、羟丙基化、酯化反应合成了一系列黄芩苷衍生物;分别采用生化法和台盼蓝染色法测试目标化合物对小鼠脑脂质过氧化产物丙二醛(MDA)的体外抑制作用及对白血病细胞HL-60的生长抑制活性。结果合成了13个黄芩苷衍生物,其结构经1H-NMR和MS确证。其中,化合物3~6、11~13为未见文献报道的新化合物。化合物1、6对MDA的抑制作用显著,化合物7~10、12具有中等强度的抑制HL-60生长作用。结论黄芩苷结构中的酚羟基是其抑制脂质过氧化产物MDA的活性基团,葡萄糖醛酸的6位游离羧基是能够增强化合物抗肿瘤活性的有效基团。
Objective To improve the solubility of baicalin, a series of baicalin derivatives were designed and synthesized, and their anti-lipid peroxidation activity and anti-tumor activity were evaluated. Methods Baicalin and ethylene oxide (propane) were used as raw materials to synthesize a series of baicalin derivatives by hydroxyethylation, hydroxypropylation and esterification. The biochemical and trypan blue staining methods were used to test the target Inhibitory Effect of Compounds on Mouse Brain Lipid Peroxidation Product Malondialdehyde (MDA) in vitro and Growth Inhibitory Activity on Leukemia Cell Line HL-60. Results Thirteen baicalin derivatives were synthesized and their structures were confirmed by 1H-NMR and MS. Among them, compounds 3 ~ 6 and 11 ~ 13 are new compounds which have not been reported in the literature. The inhibitory effect of compound 1, 6 on MDA was significant. Compounds 7 ~ 10,12 had a moderate inhibitory effect on HL-60 growth. Conclusion The phenolic hydroxyl group in the baicalin structure is the active group that inhibits the lipid peroxidation product MDA. The free carboxyl group at the 6-position of glucuronic acid is an effective group that can enhance the antitumor activity of the compound.