Netamines H-N, tricyclic alkaloids from the marine sponge Biemna laboutei and their antimalarial activity

J Nat Prod. 2014 Apr 25;77(4):818-23. doi: 10.1021/np4009283. Epub 2014 Mar 6.

Abstract

Chemical examination of the CH2Cl2-MeOH (1:1) extract of the Madagascar sponge Biemna laboutei resulted in the isolation of seven new tricyclic alkaloids, netamines H-N (1-7), along with the known netamine G and mirabilins A, C, and F. Their structures were elucidated by interpretation of 1D and 2D NMR spectra and HRESIMS data. All compounds were evaluated for their cytotoxicity against KB cells and their antiplasmodial activity. Netamine M (6) was found to be cytotoxic, with an IC50 value in the micromolar range, and netamine K (4) exhibited activity against Plasmodium falciparum with an IC50 value of 2.4 μM.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkaloids / chemistry
  • Alkaloids / isolation & purification*
  • Alkaloids / pharmacology*
  • Animals
  • Antimalarials / chemistry
  • Antimalarials / isolation & purification*
  • Antimalarials / pharmacology*
  • Antineoplastic Agents, Phytogenic / chemistry
  • Antineoplastic Agents, Phytogenic / isolation & purification*
  • Antineoplastic Agents, Phytogenic / pharmacology*
  • Humans
  • Inhibitory Concentration 50
  • Madagascar
  • Marine Biology
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Plasmodium falciparum / drug effects*
  • Porifera / chemistry*
  • Quinazolines / chemistry
  • Quinazolines / isolation & purification*
  • Quinazolines / pharmacology*

Substances

  • Alkaloids
  • Antimalarials
  • Antineoplastic Agents, Phytogenic
  • Quinazolines
  • netamine K