Iodocionin, a cytotoxic iodinated metabolite from the Mediterranean ascidian Ciona edwardsii

Mar Drugs. 2010 Feb 21;8(2):285-91. doi: 10.3390/md8020285.

Abstract

Chemical investigation of the Mediterranean ascidian Ciona edwardsii has been performed, leading to the isolation of two halogenated compounds: a new tyrosineiodinated derivative iodocionin (1) and the relevant brominated analogue (2), previously isolated from a Caribbean sponge. The structure of the new compound 1 has been assigned on the basis of spectroscopic analysis. Both compounds were tested for cytotoxicity in vitro against two different cancer cell lines, L5178Y (mouse lymphoma) and PC-12 (rat pheochromocytoma). Iodocionin was shown to possess significant and selective activity against lymphoma cells with an IC(50) of 7.75 microg/mL.

Keywords: cytotoxic activity; iodinated metabolites; natural products; structure elucidation.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amphetamines / chemistry
  • Amphetamines / isolation & purification*
  • Amphetamines / pharmacology
  • Animals
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / isolation & purification*
  • Antineoplastic Agents / pharmacology
  • Cell Line, Tumor
  • Magnetic Resonance Spectroscopy
  • Mice
  • PC12 Cells
  • Rats
  • Spectrometry, Mass, Electrospray Ionization
  • Urochordata / metabolism*

Substances

  • 2-(4-hydroxy-3-iodophenyl)-N,N,N-trimethylethanaminium
  • Amphetamines
  • Antineoplastic Agents