Isolation of cytotoxic sesquiterpene lactones from the Tanacetopsis karataviensis (Kovalevsk.) Kovalevsk

Nat Prod Res. 2021 Jun;35(12):1939-1948. doi: 10.1080/14786419.2019.1647423. Epub 2019 Jul 30.

Abstract

The structures and anticancer effects of two sesquiterpene lactones, 1 R,10S,3S,4R-diepoxyguai-5S,6S,7S-11(13)-en-6,12-olide (1) and hanphyllin (2) isolated from the aerial part of Tanacetopsis karataviensis (Kovalevsk.) Kovalevsk were investigated. The compound 1 was isolated for the first time as a natural compound and its structure was investigated by HR-ESI-MS, IR and NMR techniques. The X-ray diffraction analysis was performed to accurately determine the spatial structures of 1 and 2. Furthermore, we evaluated the cytotoxic activity of 1 and 2, and the chloroform fraction which contains both of them. Cytotoxic activity revealed that the effect of the chloroform fraction is stronger in growth inhibition of HeLa (89.7%) and HEp-2 (63.0%) cancer cells than the effect of individual compounds 1 (55.9 and 36.3%), 2 (78.6 and 50.3%) and the reference cisplatin (58.0 and 46.8%) respectively. Moreover, the chloroform fraction is less toxic to the hepatocytes.

Keywords: Tanacetopsis karataviensis (Kovalevsk.) Kovalevsk; X-ray analysis; cytotoxic activity; sesquiterpene lactones.

MeSH terms

  • Antineoplastic Agents, Phytogenic / chemistry
  • Antineoplastic Agents, Phytogenic / pharmacology*
  • Asteraceae / chemistry*
  • Drug Screening Assays, Antitumor
  • HeLa Cells
  • Humans
  • Lactones / chemistry
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Plant Components, Aerial / chemistry
  • Plant Extracts / chemistry
  • Sesquiterpenes / chemistry*
  • Sesquiterpenes / pharmacology*
  • Spectrometry, Mass, Electrospray Ionization

Substances

  • Antineoplastic Agents, Phytogenic
  • Lactones
  • Plant Extracts
  • Sesquiterpenes