Trifunović Snežana, Isaković Anđelka M, Isaković Aleksandra, Vučković Ivan, Mandić Boris, Novaković Miroslav, Vajs Vlatka, Milosavljević Slobodan, Trajković Vladimir
Faculty of Chemistry, University of Belgrade, Belgrade, Serbia.
Institute of Medical and Clinical Biochemistry, School of Medicine, University of Belgrade, Belgrade, Serbia.
Planta Med. 2014 Mar;80(4):297-305. doi: 10.1055/s-0033-1360312. Epub 2014 Feb 7.
Further phytochemical investigation of the aerial parts of Achillea clavennae has resulted in the isolation of three new sesquiterpene lactones: two highly oxygenated germacranolides (1, 2) and the iso-seco-guaianolide 9(R)-acetoxy-3-O-methyl-iso-seco-tanapartholide (3). Eight known compounds were also found, of which 9α-acetoxycanin (5), sintenin (6), and oleanolic acid (7) were detected for the first time. The structures of the isolated compounds were elucidated by combined spectroscopic methods (1D and 2D NMR, HRESIMS, CIMS, and FTIR). While the predominant metabolite germacranolide sintenin (6) was not cytotoxic, the new iso-seco-guaianolide (3) displayed cytotoxicity comparable to that of cisplatin and the lactone apressin (4), inducing partly apoptotic death in human U251 and rat C6 glioma cell lines.
对高山蓍地上部分进行进一步的植物化学研究，从中分离出三种新的倍半萜内酯：两种高度氧化的吉马烷型内酯（1, 2）和异裂环愈创木烷型内酯9(R)-乙酰氧基-3-O-甲基-异裂环单萜内酯（3）。还发现了八种已知化合物，其中9α-乙酰氧基卡宁（5）、辛特宁（6）和齐墩果酸（7）为首次检测到。通过综合光谱方法（一维和二维核磁共振、高分辨电喷雾电离质谱、化学电离质谱和傅里叶变换红外光谱）阐明了分离得到的化合物的结构。虽然主要代谢产物吉马烷型内酯辛特宁（6）没有细胞毒性，但新的异裂环愈创木烷型内酯（3）显示出与顺铂和内酯阿普瑞辛（4）相当的细胞毒性，在人U251和大鼠C6胶质瘤细胞系中诱导部分凋亡死亡。
