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

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

Nan-Lin Zhu ¹, Chunping Tang ², Chenghui Xu, Chang-Qiang Ke ², Ge Lin ², Janar Jenis ³, Sheng Yao ², Hongchun Liu, Yang Ye ¹ ² ⁴ ⁵

Affiliations

1 University of Chinese Academy of Sciences , No. 19A Yuquan Road , Beijing 100049 , People's Republic of China.
2 SIMM-CUHK Joint Research Laboratory for Promoting Globalization of Traditional Chinese Medicines , Shanghai 201203 , People's Republic of China.
3 Research Center for Medicinal Plants , Al-Farabi Kazakh National University , Al-Farabi Avenue 71 , 050040 Almaty , Republic of Kazakhstan.
4 Collaborative Innovation Center of Southwest Ethnic Medicine , Guangxi Normal University , Guiling 541001 , People's Republic of China.
5 School of Life Science and Technology , ShanghaiTech University , Shanghai 201203 , People's Republic of China.

PMID: 30869892 DOI: 10.1021/acs.jnatprod.8b01004

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 IC₅₀ values ranging from 2.8 to 10.3 μM.

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