Lathyrane and Jatrophane Diterpenoids from Euphorbia helioscopia Evaluated for Cytotoxicity against a Paclitaxel-Resistant A549 Human Lung Cancer Cell Line

J Nat Prod. 2022 Apr 22;85(4):1174-1179. doi: 10.1021/acs.jnatprod.1c01050. Epub 2022 Mar 24.

Abstract

A phytochemical investigation on the aerial parts of Euphorbia helioscopia resulted in the isolation of 27 macrocyclic diterpenoids, including three previously unreported lathyrane derivatives, euphohelioscopoids A-C (1-3). Their structures were elucidated by spectroscopic data interpretation. Three jatrophanes, euphoscopin C (4), euphorbiapene D (6), and euphoheliosnoid A (5), showed cytotoxicity against a paclitaxel-resistant A549 human lung cancer cell line with IC50 values of 6.9, 7.2, and 9.5 μM, respectively, but were inactive against the parent A549 human lung cancer cell line (IC50 > 10 μM). It was found that jatrophanes with a benzoyloxy or a nicotinoyloxy substituent at C-7 showed more potent cytotoxic activity than their analogues containing acetyloxy and hydroxy groups at this position.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Cell Line
  • Diterpenes* / chemistry
  • Diterpenes* / pharmacology
  • Euphorbia* / chemistry
  • Humans
  • Lung Neoplasms* / drug therapy
  • Molecular Structure
  • Paclitaxel / pharmacology

Substances

  • Diterpenes
  • jatrophane
  • lathyrane
  • Paclitaxel