Abstract

Two ent-kaurene diterpenoids, ent-15- β -acetyloxy-kaur-16-en-19-oic acid (xylopic acid) 1 and ent-7-oxo-kaur-16-en-19-oic acid 2 were isolated from the fruits of Xylopia aethiopica. Chemical manipulation of xylopic acid yielded ent-kaurane derivatives 3, 4, 5, and 6. Their structures were elucidated by spectroscopic analysis, including 1 D- and 2 D-NMR spectroscopies. The antiproliferative activities of compounds 1, 2, 3, 4, and 6 were tested on breast MCF7 and SkBr3, endometrial Ishikawa, ovarian BG-1, mesothelioma IST-MES1 and hepatocellular HepG2 human tumor cells, and on mammalian MRC-10 fibroblast cells. Ketone 2 showed significant antiproliferative activity against MFC7 human breast cancer cells (IC₅₀ = 3 ± 1 µM) and A549 pulmonary adenocarcinoma (8 ± 1 µM), that was higher than the well-known anti-cancer agent cisplatin (IC₅₀ = 19 ± 3 and 15 ± 4 µM, respectively).

摘要

两种ent -kaurene 二萜，ent -15- β -acetyloxy -kaur-16-en-19-oic acid (xylopic acid) 1和ent -7-oxo-kaur-16-en-19-oic acid 2分离自Xylopia aethiopica的果实。木糖酸的化学操作产生了ent -kaurane 衍生物3、4、5和6。它们的结构通过光谱分析阐明，包括 1 D-和 2 D-NMR 光谱。化合物1 , 2 , 3 , 4的抗增殖活性 和6个在乳腺 MCF7 和 SkBr3、子宫内膜石川、卵巢 BG-1、间皮瘤 IST-MES1 和肝细胞 HepG2 人类肿瘤细胞以及哺乳动物 MRC-10 成纤维细胞上进行了测试。酮2对 MFC7 人乳腺癌细胞 (IC ₅₀ = 3 ± 1 µM) 和 A549 肺腺癌 (8 ± 1 µM) 显示出显着的抗增殖活性，高于众所周知的抗癌剂顺铂 (IC ₅₀ = 19 ± 3 和 15 ± 4 µM，分别）。