Phoriospongin A and B: two new nematocidal depsipeptides from the Australian marine sponges Phoriospongia sp. and Callyspongia bilamellata

J Nat Prod. 2002 Mar;65(3):358-63. doi: 10.1021/np010329d.

Abstract

Bioassay-directed fractionation of two southern Australian sponges, Phoriospongia sp. and Callyspongia bilamellata, yielded two new nematocidal depsipeptides, identified as phoriospongins A (1) and B (2). The structures of the phoriospongins were determined by detailed spectroscopic analysis and comparison with the previously reported sponge depsipeptide cyclolithistide A (3), as well as ESIMS and HPLC analysis of acid hydrolysates. It is noteworthy that the unique and yet structurally related metabolites 1-3 are found in sponges spanning three taxonomic orders, Poescilosclerida, Haplosclerida, and Lithistida.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amino Acids / analysis
  • Animals
  • Antinematodal Agents / chemistry
  • Antinematodal Agents / isolation & purification*
  • Antinematodal Agents / pharmacology
  • Australia
  • Chromatography, High Pressure Liquid
  • Depsipeptides*
  • Hydrolysis
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Peptides, Cyclic / chemistry
  • Peptides, Cyclic / isolation & purification*
  • Peptides, Cyclic / pharmacology
  • Porifera / chemistry*
  • Spectrometry, Mass, Electrospray Ionization
  • Spectrophotometry, Infrared
  • Valine / analogs & derivatives
  • Valine / chemical synthesis

Substances

  • Amino Acids
  • Antinematodal Agents
  • Depsipeptides
  • Peptides, Cyclic
  • phoriospongin A
  • phoriospongin B
  • Valine