Aporphine alkaloids from the leaves of Phoebe grandis (Nees) Mer. (Lauraceae) and their cytotoxic and antibacterial activities

Molecules. 2013 Jul 29;18(8):8994-9009. doi: 10.3390/molecules18088994.

Abstract

The oxoaporphine alkaloid lysicamine (1), and three proaporphine alkaloids, litsericinone (2), 8,9,11,12-tetrahydromecambrine (3) and hexahydromecambrine A (4) were isolated from the leaves of Phoebe grandis (Nees) Merr. (Lauraceae). Compounds 2 and 3 were first time isolated as new naturally occurring compounds from plants. The NMR data for the compounds 2-4 have never been reported so far. Compounds 1 and 2 showed significant cytotoxic activity against a MCF7 (human estrogen receptor (ER+) positive breast cancer) cell line with IC₅₀ values of 26 and 60 µg/mL, respectively. Furthermore, in vitro cytotoxic activity against HepG2 (human liver cancer) cell line was evaluated for compounds 1-4 with IC₅₀ values of 27, 14, 81 and 20 µg/mL, respectively. Lysicamine (1) displayed strong antibacterial activity against Bacillus subtilis (B145), Staphylococcus aureus (S1434) and Staphylococus epidermidis (a clinically isolated strain) with inhibition zones of 15.50 ± 0.57, 13.33 ± 0.57 and 12.00 ± 0.00 mm, respectively. However, none of the tested pathogenic bacteria were susceptible towards compounds 2 and 3.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkaloids / administration & dosage*
  • Alkaloids / chemistry
  • Alkaloids / isolation & purification
  • Anti-Bacterial Agents / administration & dosage
  • Anti-Bacterial Agents / chemistry
  • Aporphines / administration & dosage*
  • Aporphines / chemistry
  • Aporphines / isolation & purification
  • Bacteria / drug effects*
  • Cell Proliferation / drug effects*
  • Cytotoxins / administration & dosage
  • Cytotoxins / chemistry
  • Hep G2 Cells / drug effects
  • Humans
  • MCF-7 Cells / drug effects
  • Plant Extracts / administration & dosage
  • Plant Extracts / chemistry
  • Plant Leaves / chemistry
  • Saturn

Substances

  • Alkaloids
  • Anti-Bacterial Agents
  • Aporphines
  • Cytotoxins
  • Plant Extracts