Antiproliferative activity of diarylheptanoids from the seeds of Alpinia blepharocalyx
Antiproliferative activity of diarylheptanoids from the seeds of Alpinia blepharocalyx
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DOI：
10.1248/bpb.24.525
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发表时间：
2001-05-01
影响因子：
2
通讯作者：
Kadota, S
中科院分区：
文献类型：
--
作者：
Ali, MS;Banskota, AH;Kadota, S
毛萼山姜种子的95%EtOH提取物对人HT-1080纤维肉瘤和小鼠结肠癌26-L5细胞具有明显的抗增殖活性。提取物的化学研究导致分离出44种新的（1-44）和一种已知的（45）二芳基庚烷类化合物，11种酚类化合物（46-56）以及β-谷甾醇葡萄糖苷（57）。几乎所有分离的化合物显示出显着的抗增殖活性，在浓度依赖性的方式。在这些化合物中，epicalyxin F（17）对结肠26-L5癌细胞的增殖表现出最有效的活性，其ED 50值为0.89 μ M，而calyxin B（2）对人HT-1080纤维肉瘤细胞表现出最有效的活性，其ED 50值为0.69 μ M。此外，萼素B（2）和K（11），表萼素F（17），I（20）和K（22），6-羟基萼素F（25），眼睑萼素B（27）和7与表萼素G（18）的混合物以及萼素J（10）与表萼素J（21）的混合物具有比临床上使用的抗癌药5-氟尿嘧啶更有效的活性，对HT-1080纤维肉瘤细胞的结构活性关系的分析表明，查尔酮或黄烷酮部分的连接位置不影响活性，尽管它们的存在导致抗增殖活性的显著增强。此外，查尔酮部分的共轭双键和酚羟基增强了化合物的抗增殖活性。
The 95% EtOH extract of the seeds of Alpinia blepharocalyx (Zingiberaceae) showed significant antiproliferative activity towards human HT-1080 fibrosarcoma and murine colon 26-L5 carcinoma cells. Chemical investigation of the extract led to the isolation of forty-four new (1-44) and one known (45) diarylheptanoids, eleven phenolic compounds (46-56) together with beta -sitosterol glucoside (57). Almost all the isolated compounds showed significant antiproliferative activity in a concentration-dependent manner. Among the compounds, epicalyxin F (17) exhibited the most potent activity against the proliferation of colon 26-L5 carcinoma cells with an ED50 value of 0.89 muM, while calyxin B (2) exhibited the most potent activity against human HT-1080 fibrosarcoma cells with an ED50 value of 0.69 muM. Moreover, calyxins B (2) and K (11), epicalyxins F (17), I (20) and K (22), 6-hydroxycalyxin F (25), blepharocalyxin B (27) and mixtures of 7 and epicalyxin G (18) and of calyxin J (10) and epicalyxin J (21) possessed more potent activity than a clinically used anticancer drug, 5-fluorouracil, towards HT-1080 fibrosarcoma cells, Analysis of the structure activity relationship suggested that the position of the attachment of a chalcone or a flavanone moiety does not affect the activity, although their presence in association causes a substantial enhancement of the antiproliferative activity. Moreover, the conjugated double bond of the chalcone moiety and the phenolic hydroxyl group potentiate the antiproliferative activity of the compounds.