Cytotoxic halogenated monoterpenes from Plocamium cartilagineum

Nat Prod Res. 2017 Feb;31(3):261-267. doi: 10.1080/14786419.2016.1230115. Epub 2016 Sep 14.

Abstract

As a result of our efforts to identify bioactive agents from marine algae, we have isolated and identified one new halogenated monoterpene 1 [(-)-(5E,7Z)-348-trichloro-7-dichloromethyl-3-methyl-157-octatriene] in addition to three known compounds (2, 3 and 4) from the red alga Plocamium cartilagineum collected by hand from the eastern coast of South Africa. Compound 1 was found to be active as a cytotoxic agent in human lung cancer (NCI-H460) and mouse neuro-2a cell lines (IC50 4 μg/mL). Two of these compounds (3 and 4) were found to have cytotoxic activity in other cell line assays, especially against human leukaemia and human colon cancers (IC50 1.3 μg/mL). None of these metabolites were active as sodium channel blockers or activators. All structures were determined by spectroscopic methods (UV, IR, LRMS, HRMS, 1D NMR and 2D NMR). 1D and 2D NOE experiments were carried out on these compounds to confirm the geometry of the double bonds.

Keywords: Halogenated monoterpenes; Plocamium cartilagineum; human colon cancers; human leukaemia; human lung cancers.

MeSH terms

  • Animals
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / pharmacology
  • Cell Line, Tumor
  • Colonic Neoplasms / drug therapy
  • Halogenation
  • Humans
  • Leukemia / drug therapy
  • Lung Neoplasms / drug therapy
  • Magnetic Resonance Spectroscopy
  • Mice
  • Molecular Structure
  • Monoterpenes / chemistry
  • Monoterpenes / pharmacology*
  • Monoterpenes / toxicity
  • Plocamium / chemistry*
  • Spectrum Analysis

Substances

  • Antineoplastic Agents
  • Monoterpenes