五种来自飞廉的新的 C/C 倍半萜二聚体。
Five new C/C sesquiterpene lactone dimers from Carpesium abrotanoides.
机构信息
School of Animal Science, Xichang College, Xichang, Sichuan 615000, PR China; Department of Phytochemistry, School of Pharmacy, Second Military Medical University, Shanghai 200433, PR China,.
Department of Phytochemistry, School of Pharmacy, Second Military Medical University, Shanghai 200433, PR China.
出版信息
Fitoterapia. 2020 Sep;145:104630. doi: 10.1016/j.fitote.2020.104630. Epub 2020 May 23.
Five new unusual C/C sesquiterpene lactone dimers, carabrodilactones A-E (1-5), along with four known common C/C SLDs, carpedilactones A and B (6 and 7), faberidilactone A (8), and faberidilactone C (9), were isolated from the whole plants of Carpesium abrotanoides. The structures of 1-5 featured a flexible C-11/C-13' linked single bond between two sesquiterpene units and a tailed acetyl connected to the C-13 position. The preferential conformation of 1-5 was elucidated by the diagnostic NMR data of geminal proton of H-13. The biogenetic pathway of 1-5 was proposed to involve Stetter and Michael addition reactions. In addition, compound 1 exhibited significant cytotoxicities against the four cell lines (A549, HCT116, MDA-MB, and BEL7404 cells) with IC value in the range of 3.08-8.05 μM, while compounds 2-5 showed weak cytotoxicities.
从新疆飞蓬（Carpesium abrotanoides）全草中分离得到五个新的罕见的 C/C 倍半萜内酯二聚体，即 carabrodilactones A-E（1-5），以及四个常见的 C/C SLD，即 carpedilactones A 和 B（6 和 7）、faberidilactone A（8）和 faberidilactone C（9）。1-5 的结构特征是两个倍半萜单元之间具有灵活的 C-11/C-13' 单键连接和连接在 C-13 位置的尾部乙酰基。1-5 的优先构象通过 H-13 的偕二质子的诊断性 NMR 数据阐明。提出了 1-5 的生物合成途径涉及 Stetter 和迈克尔加成反应。此外，化合物 1 对四种细胞系（A549、HCT116、MDA-MB 和 BEL7404 细胞）表现出显著的细胞毒性，IC 值范围为 3.08-8.05 μM，而化合物 2-5 表现出较弱的细胞毒性。
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