Bromopyrrole alkaloids isolated from the Patagonian bryozoan Aspidostoma giganteum.

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.

• Authors: Laura P Patiño C, Claudia Muniain, Maria Elena Knott, Lydia Puricelli, Jorge A Palermo
• Journal: Journal of natural products (J Nat Prod) Vol. 77 Issue 5 Pg. 1170-8 (May 23 2014) ISSN: 1520-6025 [Electronic] United States
• PMID: 24824796 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)

Chemical References

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

Topics

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