Department of Pharmacognosy, Faculty of Pharmacy, Ege University, 35040 Bornova/İzmir, Turkey.
Institute of Pharmacognosy, Interdisciplinary Excellence Centre, University of Szeged, 6720 Szeged, Hungary.
Molecules. 2019 Aug 30;24(17):3165. doi: 10.3390/molecules24173165.
Multistep chromatographic separations of the chloroform extract of the Turkish endemic plant (Boiss.) Wagenitz (syn. Boiss.) resulted in the isolation of six guaianolid-type sesquiterpenes, chlorojanerin (), 19-deoxychlorojanerin (), 15-hydroxyjanerin (), aguerin B (), cynaropicrin (), eleganin (); three flavonoids, apigenin, 6-methoxyluteolin and jaceosidine; two glycosides, benzyl-1-β-d-glucoside and 3()-hexenyl-1-β-d-glucoside; and the coumarin scopoletin. The structures were established by the interpretation of their ESI-MS and 1D and 2D NMR data including H-NMR, JMOD, H,H-COSY, HSQC, HMBC, and NOESY experiments. All compounds were isolated for the first time from . Compounds -, the isolated flavonoids and scopoletin were evaluated for their antiproliferative activities on human gynecological cancer cell lines (SiHa, HeLa, and MDA-MB-231 cells) using the MTT (3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide) assay. Chlorojanerin (), 19-deoxychlorojanerin (), aguerin B (), cynaropicrin (), eleganin () were shown to have noteworthy effects on all of the tested cell lines, while apigenin, jaceosidine, and 6-methoxyluteolin were moderately active on HeLa cells. The highest activities were demonstrated by the chlorine-containing derivatives chlorojanerin () and 19-deoxychlorojanerin () with IC values of 2.21 and 2.88 µM, respectively, against the triple negative breast cancer model MDA-MB-231 cells.
从土耳其特有植物(Boiss.) Wagenitz(同义词:Boiss.)的氯仿提取物中进行多步色谱分离,得到了六种愈创木烷型倍半萜烯,即氯乔那林()、19-去氧氯乔那林()、15-羟基乔那林()、阿圭林 B()、莪术呋喃()、埃拉金();三种黄酮类化合物,芹菜素、6-甲氧基木犀草素和杰索辛;两种糖苷,苄基-1-β-D-葡萄糖苷和 3-()-己烯基-1-β-D-葡萄糖苷;以及香豆素花椒毒素。通过解析它们的 ESI-MS 和 1D 和 2D NMR 数据(包括 H-NMR、JMOD、H-H-COSY、HSQC、HMBC 和 NOESY 实验),确定了它们的结构。所有化合物均为首次从 中分离得到。化合物 - 、分离得到的黄酮类化合物和花椒毒素均通过 MTT(3-(4,5-二甲基噻唑-2-基)-2,5-二苯基四唑溴盐)测定法评估了它们对人妇科癌症细胞系(SiHa、HeLa 和 MDA-MB-231 细胞)的抗增殖活性。氯乔那林()、19-去氧氯乔那林()、阿圭林 B()、莪术呋喃()、埃拉金()对所有测试的细胞系均显示出显著的作用,而芹菜素、杰索辛和 6-甲氧基木犀草素对 HeLa 细胞表现出中度活性。含氯衍生物氯乔那林()和 19-去氧氯乔那林()表现出最高的活性,对三阴性乳腺癌模型 MDA-MB-231 细胞的 IC 值分别为 2.21 和 2.88 µM。