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

Two new bromopyrrole peptides, haloirciniamide A (<b>1</b>) and seribunamide A (<b>2</b>), have been isolated from an Indonesian marine sponge of the genus <i>Ircinia</i> collected in the Thousand Islands (Indonesia). The planar structure of both compounds was ass...

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Bibliographic Details
Main Authors: Rogelio Fernández, Asep Bayu, Tri Aryono Hadi, Santiago Bueno, Marta Pérez, Carmen Cuevas, Masteria Yunovilsa Putra
Format: Article
Language:English
Published: MDPI AG 2020-07-01
Series:Marine Drugs
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Online Access:https://www.mdpi.com/1660-3397/18/8/396
Description
Summary:Two new bromopyrrole peptides, haloirciniamide A (<b>1</b>) and seribunamide A (<b>2</b>), have been isolated from an Indonesian marine sponge of the genus <i>Ircinia</i> 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 <b>1</b> and <b>2</b> was determined by the application of Marfey’s method. Compound <b>1</b> is the first dibromopyrrole cyclopeptide having a chlorohistidine ring, while compound <b>2</b> 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.
ISSN:1660-3397