Marine Drugs (Jul 2020)

Unique Polyhalogenated Peptides from the Marine Sponge <i>Ircinia</i> sp.

  • Rogelio Fernández,
  • Asep Bayu,
  • Tri Aryono Hadi,
  • Santiago Bueno,
  • Marta Pérez,
  • Carmen Cuevas,
  • Masteria Yunovilsa Putra

DOI
https://doi.org/10.3390/md18080396
Journal volume & issue
Vol. 18, no. 8
p. 396

Abstract

Read online

Two new bromopyrrole peptides, haloirciniamide A (1) and seribunamide A (2), have been isolated from an Indonesian marine sponge of the genus Ircinia collected in the Thousand Islands (Indonesia). The planar structure of both compounds was assigned on the basis of extensive 1D and 2D NMR spectroscopy and mass spectrometry. The absolute configuration of the amino acid residues in 1 and 2 was determined by the application of Marfey’s method. Compound 1 is the first dibromopyrrole cyclopeptide having a chlorohistidine ring, while compound 2 is a rare peptide possessing a tribromopyrrole ring. Both compounds failed to show significant cytotoxicity against four human tumor cell lines, and neither compound was able to inhibit the enzyme topoisomerase I or impair the interaction between programmed cell death protein PD1 and its ligand, PDL1.

Keywords