Convolutamines I and J, antitrypanosomal alkaloids from the bryozoan Amathia tortusa

Bioorg Med Chem. 2011 Nov 15;19(22):6615-9. doi: 10.1016/j.bmc.2011.06.006. Epub 2011 Jun 12.

Abstract

Mass-directed isolation of the CH(2)Cl(2)/CH(3)OH extract from the marine bryozoan Amathia tortusa resulted in the purification of two new brominated alkaloids, convolutamines I (1) and J (2). The structures of 1 and 2 were determined following spectroscopic data analysis. Both compounds were isolated during a drug discovery program aimed at identifying new antitrypanosomal leads from a prefractionated natural product library. Compounds 1 and 2 were shown to be active toward the parasite Trypanosoma brucei brucei with IC(50) values of 1.1 and 13.7 μM, respectively. Preliminary toxicity profiling was also performed on both 1 and 2 using the human embryonic kidney cell line, HEK293. Compound 1 was shown to exhibit cytotoxicity against HEK293 with an IC(50) of 22.0 μM whilst 2 was inactive at 41.0 μM.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Bryozoa / chemistry*
  • HEK293 Cells
  • Humans
  • Indole Alkaloids / chemistry*
  • Indole Alkaloids / isolation & purification
  • Indole Alkaloids / pharmacology
  • Nuclear Magnetic Resonance, Biomolecular
  • Plasmodium falciparum / drug effects
  • Trypanocidal Agents / chemistry
  • Trypanocidal Agents / isolation & purification
  • Trypanocidal Agents / pharmacology
  • Trypanosoma brucei brucei / drug effects

Substances

  • Indole Alkaloids
  • Trypanocidal Agents