Bromopyrrole alkaloids isolated from the Patagonian bryozoan Aspidostoma giganteum

J Nat Prod. 2014 May 23;77(5):1170-8. doi: 10.1021/np500012y. Epub 2014 May 13.

Abstract

Nine new bromopyrrole alkaloids, aspidostomides A-H and aspidazide A (1-9), were isolated from the Patagonian bryozoan Aspidostoma giganteum. Aspidostomides A-H have dibromotyrosine- or bromotryptophan-derived moieties forming either linear amides or pyrroloketopiperazine-type lactams with a bromopyrrole carboxylic acid as a common structural motif. On the other hand, aspidazide A is a rare asymmetric acyl azide formed by an N-N link of two different pyrroloketopiperazine lactams and is the first isolated compound of this class from marine invertebrates. This work is the first report of secondary metabolites isolated from a bryozoan from the Patagonian region. The structures of compounds 1-9 were elucidated by spectroscopic methods and chemical transformations. One of these compounds, aspidostomide E (5), was moderately active against the 786-O renal carcinoma cell line.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Agelas / chemistry
  • Alkaloids / chemistry
  • Alkaloids / isolation & purification*
  • Animals
  • Carboxylic Acids
  • Humans
  • Hydrocarbons, Brominated / chemistry
  • Hydrocarbons, Brominated / isolation & purification*
  • Molecular Structure
  • Nuclear Magnetic Resonance, Biomolecular
  • Pyrroles / chemistry

Substances

  • Alkaloids
  • Carboxylic Acids
  • Hydrocarbons, Brominated
  • Pyrroles
  • aspidostomide E