Monoterpenoid indole alkaloids from Alstonia rupestris with cytotoxic, anti-inflammatory and antifungal activities

Molecules. 2013 Jun 21;18(6):7309-22. doi: 10.3390/molecules18067309.

Abstract

Phytochemical investigation of the 70% EtOH extract of the leaves of Alstonia scholaris afforded seven new monoterpenoid indole alkaloids: scholarisins I-VII (1-7), and three known compounds: (3R,5S,7R,15R,16R,19E)-scholarisine F (8), 3-epi-dihydro- corymine (9), and (E)-16-formyl-5α-methoxystrictamine (10). Structural elucidation of all the compounds was accomplished by spectral methods such as 1D- and 2D-NMR, IR, UV, and HRESIMS. The isolated compounds were tested in vitro for cytotoxicity against seven tumor cell lines, anti-inflammatory activities against Cox-1 and Cox-2, and antifungal potential against five species of fungi. Compounds 1, 6, and 10 exhibited significant cytotoxicities against all the tested tumor cell lines with IC₅₀ values of less than 30 μM and selective inhibition of Cox-2 comparable with the standard drug NS-398 (>90%). Additionally, 1, 2, 3 and 8 showed antifungal activity against two fungal strains (G. pulicaris and C. nicotianae).

MeSH terms

  • Alstonia / chemistry*
  • Anti-Inflammatory Agents / chemistry*
  • Anti-Inflammatory Agents / pharmacology
  • Anti-Inflammatory Agents / toxicity
  • Antifungal Agents / chemistry*
  • Antifungal Agents / pharmacology
  • Antifungal Agents / toxicity
  • Cell Line, Tumor
  • Cyclooxygenase Inhibitors / chemistry
  • Cyclooxygenase Inhibitors / pharmacology
  • Humans
  • Inhibitory Concentration 50
  • Microbial Sensitivity Tests
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Plant Extracts / chemistry
  • Secologanin Tryptamine Alkaloids / chemistry*
  • Secologanin Tryptamine Alkaloids / pharmacology*
  • Secologanin Tryptamine Alkaloids / toxicity

Substances

  • Anti-Inflammatory Agents
  • Antifungal Agents
  • Cyclooxygenase Inhibitors
  • Plant Extracts
  • Secologanin Tryptamine Alkaloids