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.