Ianthelliformisamines A-C, antibacterial bromotyrosine-derived metabolites from the marine sponge Suberea ianthelliformis

J Nat Prod. 2012 May 25;75(5):1001-5. doi: 10.1021/np300147d. Epub 2012 Apr 19.

Abstract

A high-throughput screening campaign using a prefractionated natural product library and an in vitro Pseudomonas aeruginosa (PAO200 strain) assay identified two antibacterial fractions derived from the marine sponge Suberea ianthelliformis. Mass-directed isolation of the CH(2)Cl(2)/CH(3)OH extract from S. ianthelliformis resulted in the purification of three new bromotyrosine-derived metabolites, ianthelliformisamines A-C (1-3), together with the known natural products aplysamine 1 (4) and araplysillin I (5). The structures of 1-3 were determined following analysis of 1D and 2D NMR and MS spectroscopic data. This is the first report of chemistry from the marine sponge S. ianthelliformis. Ianthelliformisamine A (1) showed inhibitory activity against the Gram-negative bacterium P. aeruginosa with an IC(50) value of 6.8 μM (MIC = 35 μM).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acinetobacter / drug effects
  • Animals
  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / isolation & purification*
  • Anti-Bacterial Agents / pharmacology*
  • Isoxazoles / chemistry
  • Isoxazoles / isolation & purification
  • Marine Biology
  • Microbial Sensitivity Tests
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Phenethylamines / chemistry
  • Phenethylamines / isolation & purification
  • Porifera / chemistry*
  • Pseudomonas aeruginosa / drug effects
  • Staphylococcus / drug effects
  • Tyrosine / analogs & derivatives*
  • Tyrosine / chemistry
  • Tyrosine / isolation & purification
  • Tyrosine / pharmacology

Substances

  • Anti-Bacterial Agents
  • Isoxazoles
  • Phenethylamines
  • bromotyrosine
  • ianthelliformisamine A
  • ianthelliformisamine B
  • ianthelliformisamine C
  • araplysillin I
  • Tyrosine