Novel Terpenoids with Potent Cytotoxic Activities from Resina Commiphora

Molecules. 2018 Dec 7;23(12):3239. doi: 10.3390/molecules23123239.

Abstract

A novel sesquiterpene dimer, spirocommiphorfuran A (1); two new cadinane sesquiterpenoids, commiphorenes A (2) and B (3); along with three known terpenoids (46), were isolated from Resina Commiphora. The structures of these new compounds were characterized by NMR, HRESIMS, quantum chemical computation, and X-ray diffraction analysis. Compound 1 features a 7-oxabicyclo[2.2.1]heptane-2-ene core, representing the first example of germacrane-type sesquiterpene dimer fused via a spiro ring system. Compound 2 is a novel sesquiterpene with a completely new carbon skeleton, which is characteristic of an additional carbon attaching to the cadinane backbone via a carbon⁻carbon bond. Additionally, compounds 2 and 4 exert acceptable cytotoxicity toward normal cells and high selectivity in cancer cells, especially in HepG2 cells.

Keywords: Resina Commiphora; X-ray; cytotoxic activities; quantum chemical computation; terpenoids.

MeSH terms

  • Burseraceae / chemistry*
  • Carbon-13 Magnetic Resonance Spectroscopy
  • Cell Death / drug effects
  • Cell Line, Tumor
  • Circular Dichroism
  • Humans
  • Inhibitory Concentration 50
  • Proton Magnetic Resonance Spectroscopy
  • Terpenes / chemistry
  • Terpenes / pharmacology*

Substances

  • Terpenes