Three New Cytotoxic Monoterpenoid Bisindole Alkaloids from Tabernaemontana bufalina

Planta Med. 2018 Oct;84(15):1127-1133. doi: 10.1055/a-0608-4988. Epub 2018 Apr 24.

Abstract

Three new bisindole alkaloids, 3'-(2-oxopropyl)-19,20-dihydrotabernamine (1: ), 3'-(2-oxopropyl)-ervahanine B (2: ), 19,20-dihydrovobparicine (3: ), and 20 known compounds were isolated from the aerial parts of Tabernaemontana bufalina. The structures of these alkaloids were elucidated using spectroscopic methods. The absolute configurations of 1: -3: were determined by the circular dichroic exciton chirality method. Compounds 1: -23: were screened for their cytotoxicity against two human cancer cell lines, A-549 and MCF-7. Ten compounds (1: -3, 10, 14, 16, 17, 19, 22: , and 23: ) exhibited inhibitory effects against the two human cancer cells with IC50 values of 1.19 ~ 6.13 µM.

MeSH terms

  • Bridged-Ring Compounds / chemistry*
  • Bridged-Ring Compounds / isolation & purification
  • Bridged-Ring Compounds / pharmacology
  • Cell Line, Tumor
  • Humans
  • Indole Alkaloids / chemistry*
  • Indole Alkaloids / isolation & purification
  • Indole Alkaloids / pharmacology
  • Inhibitory Concentration 50
  • Magnetic Resonance Spectroscopy
  • Models, Structural
  • Monoterpenes / chemistry*
  • Monoterpenes / isolation & purification
  • Monoterpenes / pharmacology
  • Plant Components, Aerial / chemistry
  • Tabernaemontana / chemistry*

Substances

  • Bridged-Ring Compounds
  • Indole Alkaloids
  • Monoterpenes
  • ervahanine