Muhammad Ilias, Takamatsu Satoshi, Mossa Jaber S, El-Feraly Farouk S, Walker Larry A, Clark Alice M
National Center for Natural Products Research, University of Mississippi, 38677, USA.
Phytother Res. 2003 Feb;17(2):168-73. doi: 10.1002/ptr.1258.
The aerial parts of Centaurothamnus maximus yielded three cytotoxic guaianolides, chlorojanerin (1), cynaropicrin (2) and janerin (3). The structure elucidation of 1-3 was based on (1)H and (13)C NMR data, mainly 2D-NMR (1)H-(1)H COSY and (1)H-(13)C HETCOR experiments. Compounds 1-3 showed in vitro cytotoxic activity against human cancer cell lines of malignant melanoma (SK-MEL), epidermoid (KB), ductal (BT-549) and ovarian (SK-OV-3) carcinomas with IC(50) values of 2-6 microgram/mL. In addition, 12 sesquiterpene lactones (4-15), isolated previously from the aerial parts of Vicoa pentanema, were evaluated for cytotoxic and antimicrobial activities. 2alpha- Acetoxy-3beta-hydroxyalantolactone (10) and 8beta-hydroxyparthenolide (14) were found to be the main cytotoxic agents (IC(50) values of 2-6 microgram/mL against SK-MEL, BT-549 and SK-OV-3), while lactones 4, 5, 11 and 15 selectively inhibited the growth of human malignant melanoma (IC(50) value of 3.6-7.3 microgram/mL). Cell aggregation and cell adhesion assays, using HL-60 and HeLa cell lines, evaluated the effect of cytotoxic constituents 1-3, 10 and 14 on immune response and inflammation.
大花百蕊草的地上部分产生了三种具有细胞毒性的愈创木烷型倍半萜内酯，氯雅瑞宁（1）、刺菜素（2）和雅瑞宁（3）。化合物1 - 3的结构解析基于氢谱和碳谱数据，主要是二维核磁共振氢氢相关谱和氢碳异核多量子相干实验。化合物1 - 3对恶性黑色素瘤（SK - MEL）、表皮样癌（KB）、导管癌（BT - 549）和卵巢癌（SK - OV - 3）等人类癌细胞系显示出体外细胞毒性活性，半数抑制浓度值为2 - 6微克/毫升。此外，对先前从五叶歧伞菊地上部分分离得到的12种倍半萜内酯（4 - 15）进行了细胞毒性和抗菌活性评估。发现2α - 乙酰氧基 - 3β - 羟基阿兰内酯（10）和8β - 羟基小白菊内酯（14）是主要的细胞毒性剂（对SK - MEL、BT - 549和SK - OV - 3的半数抑制浓度值为2 - 6微克/毫升），而内酯4、5、11和15选择性地抑制人类恶性黑色素瘤的生长（半数抑制浓度值为3.6 - 7.3微克/毫升）。使用HL - 60和HeLa细胞系进行的细胞聚集和细胞黏附试验评估了细胞毒性成分1 - 3、10和14对免疫反应和炎症的影响。
