金盘岭泽兰全草中的细胞毒角型倍半萜内酯。

Cytotoxic Germacrane-Type Sesquiterpene Lactones from the Whole Plant of Carpesium lipskyi.

机构信息

University of Chinese Academy of Sciences , No. 19A Yuquan Road , Beijing 100049 , People's Republic of China.

SIMM-CUHK Joint Research Laboratory for Promoting Globalization of Traditional Chinese Medicines , Shanghai 201203 , People's Republic of China.

出版信息

J Nat Prod. 2019 Apr 26;82(4):919-927. doi: 10.1021/acs.jnatprod.8b01004. Epub 2019 Mar 14.

DOI:10.1021/acs.jnatprod.8b01004

PMID:30869892

Abstract

Ten new sesquiterpene lactones, carlipsines A-J (1-10), and 12 known analogues (11-22) were isolated from the whole plant of Carpesium lipskyi. Their structures were elucidated by using 1D and 2D NMR and HRESIMS analyses, and their absolute configurations were confirmed by X-ray diffraction studies. All compounds were identified as germacranolides with diverse substructural features. Compounds 1-4 are 2,5-hemiacetal-linked germacranolides. Compounds 5 and 6 possess a 1,2-epoxy moiety. Compounds 7 and 8 represent unusual 1,5-hemiacetal-linked germacranolides. Compounds 9 and 10 contain a tetrahydrofuran unit with the oxygen atom bridging C-1 and C-8. Compounds 6, 7, 8, 19, 20, 21, and 22 showed cytotoxicity against HL-60 and A-549 cell lines with IC values ranging from 2.8 to 10.3 μM.

摘要

从泽兰全草中分离得到了 10 个新的倍半萜内酯化合物，分别命名为 carlipsines A-J（1-10），以及 12 个已知的类似物（11-22）。通过 1D 和 2D NMR 和 HRESIMS 分析阐明了它们的结构，并通过 X 射线衍射研究确定了它们的绝对构型。所有化合物均被鉴定为具有不同亚结构特征的大根香叶烯型倍半萜内酯。化合物 1-4 是 2,5-半缩醛连接的大根香叶烯型倍半萜内酯。化合物 5 和 6 具有 1,2-环氧部分。化合物 7 和 8 代表不常见的 1,5-半缩醛连接的大根香叶烯型倍半萜内酯。化合物 9 和 10 含有一个四氢呋喃单元，氧原子桥接 C-1 和 C-8。化合物 6、7、8、19、20、21 和 22 对 HL-60 和 A-549 细胞系表现出细胞毒性，IC 值范围为 2.8-10.3 μM。