Bromopyrrole Alkaloid Inhibitors of the Proteasome Isolated from a Dictyonella sp. Marine Sponge Collected at the Amazon River Mouth

J Nat Prod. 2018 Oct 26;81(10):2296-2300. doi: 10.1021/acs.jnatprod.8b00533. Epub 2018 Oct 3.

Abstract

The new pyrrole-imidazole and pyrrole-guanidine alkaloids 4-debromooroidin (1), 4-debromougibohlin (2), 5-debromougibohlin (3), and 5-bromopalau'amine (4), along with the known hymenidin (5) and (+)-monobromoisophakellin (6), have been isolated from a Dictyonella sp. marine sponge, collected at the Amazon River mouth. The bromine-substitution pattern observed for compounds 1, 2 and 4 is unusual among bromopyrrole alkaloids isolated from marine sponges. The 20S proteasome inhibitory activities of compounds 1-6 have been recorded, with 5-bromopalau'amine (4) being the most active in this series.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Brazil
  • Molecular Structure
  • Porifera / chemistry*
  • Proteasome Endopeptidase Complex
  • Proteasome Inhibitors / chemistry*
  • Proteasome Inhibitors / pharmacology*
  • Pyrroles / chemistry*
  • Pyrroles / pharmacology*
  • Saccharomyces cerevisiae / drug effects
  • Saccharomyces cerevisiae / genetics

Substances

  • Proteasome Inhibitors
  • Pyrroles
  • Proteasome Endopeptidase Complex