Carbazole-pyranocoumarin conjugate and two carbazole alkaloids from the stems of Clausena excavata

Nat Prod Res. 2016 Aug;30(15):1690-7. doi: 10.1080/14786419.2015.1135143. Epub 2016 Jan 29.

Abstract

A carbazole-pyranocoumarin conjugate, carbazomarin B (1), and two carbazole alkaloids, 6-methoxymukonidine (2) and 2-hydroxy-3-methoxycarbazole (3), together with 27 known compounds (4-30), were isolated from the stems of Clausena excavata. Their structures have been elucidated by spectroscopic analyses. Compound 2 showed moderate cytotoxicity to HuCCA-1, MOLT-3 and HepG2 cancer cell lines with IC50 values of 15.09-28.50 μg/mL, but none to A549 cell line. Heptaphylline (6) and nordentatin (23) were found to show moderate cytotoxic activity against HepG2 cell line with IC50 values of 12.33 and 11.33, respectively, while clausine K (27) exhibited strong cytotoxicity with IC50 value of 1.05 μg/mL, better than a standard drug (etoposide, IC50 13.40 μg/mL).

Keywords: Clausena excavata; Rutaceae; carbazole alkaloids; cytotoxic activity.

MeSH terms

  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / isolation & purification*
  • Anti-Bacterial Agents / pharmacology
  • Antineoplastic Agents, Phytogenic / chemistry
  • Antineoplastic Agents, Phytogenic / isolation & purification*
  • Antineoplastic Agents, Phytogenic / pharmacology
  • Carbazoles / chemistry
  • Carbazoles / isolation & purification*
  • Carbazoles / pharmacology
  • Clausena / chemistry*
  • Hep G2 Cells
  • Humans
  • Magnetic Resonance Spectroscopy
  • Plant Stems / chemistry
  • Pyranocoumarins / chemistry
  • Pyranocoumarins / isolation & purification*
  • Pyranocoumarins / pharmacology

Substances

  • Anti-Bacterial Agents
  • Antineoplastic Agents, Phytogenic
  • Carbazoles
  • Pyranocoumarins
  • heptaphylline