蓬莪术姜黄素类化学成分研究

目的研究蓬莪术Curcuma phaeocaulis根茎的姜黄素类化学成分及其细胞毒活性。方法将蓬莪术根茎的95%乙醇提取物经石油醚、醋酸乙酯、正丁醇依次萃取,对醋酸乙酯萃取部位采用硅胶和葡聚糖凝胶Sephadex LH-20柱色谱、反相中压液相色谱、制备薄层色谱及半制备高效液相色谱等分离技术进行分离纯化,利用现代波谱学手段对分离的化学成分进行结构鉴定;采用MTT法对分离得到的化合物进行细胞毒活性筛选。结果从蓬莪术根茎的醋酸乙酯萃取部位分离得到4个姜黄素类化合物,分别鉴定为1,7-双(4-羟基苯基)-1E,6E-庚二烯-3-酮(1)、1,7-双(4-羟基苯基)-1,4,6-庚三烯-3-酮(2)、1,7-双(4-羟基苯基)-4E,6E-庚二烯-3-酮(3)和(1R,5S,6S)-1,5-环氧-6-羟基-1,7-双(3-甲氧基-4-羟基苯基)-庚烷(4)。MTT实验显示化合物1～3均可抑制人胃癌HGC-27细胞的增殖,仅化合物2对人乳腺癌MDA-MB-231细胞有抑制作用;化合物2和3还对人正常肝细胞L-02表现出强烈的毒性作用。结论从蓬莪术中分离得到4个姜黄素类成分,其中化合物1为新化合物,命名为姜黄素P。化合物1～3均具有一定的抑制HGC-27细胞增殖作用,其中化合物1可选择性抑制HGC-27细胞的增殖并对人正常肝L-02细胞无明显毒性作用。

Study on curcumins from Curcuma phaeocaulis

Objective To study the chemical constituents and the cytotoxic activity of curcumins from the rhizome of Curcuma phaeocaulis. Methods The 95% ethanol extract from the rhizome of C. phaeocaulis was extracted with petroleum ether, ethyl acetate, and n-butanol. The separation and purification of ethyl acetate fraction was carried out by silica gel column, sephadex LH-20 column, reversed-phase medium pressure chromatography, preparative thin-layer chromatography, and semi-preparative high performance liquid chromatography. The structures of the isolated components were identified by modern spectroscopy techniques. The isolated compounds were screened for cytotoxic activity by MTT assay. Results Four curcuminoids were isolated from the ethyl acetate extract of the rhizome of C. phaeocaulis, and identified as 1,7-bis (4-hydroxyphenyl)-1E,6E-heptadien-3-one (1), 1,7-bis (4-hydroxyphenyl)-1,4,6-heptatrien-3-one (2), 1,7-bis (4-hydroxyphenyl)-4E,6E-heptadien-3-one (3), and (1R,5S,6S)-1,5-epoxy-6-hydroxy-1,7-bis (3-methoxy-4-hydroxy-phenyl)-heptane (4). MTT experiments showed that compounds 1-3 inhibited HGC-27 cells proliferation, and only compound 2 inhibited MDA-MB-231 cells proliferation. Compounds 2 and 3 also showed strong toxic effects on human normal liver cells. Conclusion Four curcuminoids were isolated from C. phaeocaulis. Compound 1 was a new compound named curcumin P. Compounds 1-3 had a certain inhibitory effect on the proliferation of HGC-27 cells. Notably, compound 1 selectively inhibited the proliferation of HGC-27 cells and showed no obvious toxic effects on L-02 cells.