Unique Polyhalogenated Peptides from the Marine Sponge Ircinia sp.

Abstract

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.

Marine Pyrrole Alkaloids

“…Recently, two new unique bromopyrrole peptides, seribunamide A ( 482 ) and haloirciniamide A ( 483 ), have been extracted from an Indonesian marine sponge of the genus Ircinia ( Figure 67 ) [ 361 ]. Their relative and absolute stereochemistries were determined by ROESY correlations and on the basis of derivatization [ 362 ] with Marfey’s reagent, 1-fluoro-2,4-dinitrophenyl-5- l -alanine amide.…”

“…Their relative and absolute stereochemistries were determined by ROESY correlations and on the basis of derivatization [ 362 ] with Marfey’s reagent, 1-fluoro-2,4-dinitrophenyl-5- l -alanine amide. Compounds 482 and 483 did not show any cytotoxicity against several human tumor cell lines [ 361 ].…”

“…Recently, two new unique bromopyrrole peptides, seribunamide A (482) and haloirciniamide A (483), have been extracted from an Indonesian marine sponge of the genus Ircinia (Figure 67) [361]. Their relative and absolute stereochemistries were The sugar-containing pyrrole alkaloids, phallusialides A-E (477-481) were discovered in a marine bacterium of the genus Micromonospora in 2019 (Figure 66) [360].…”

Chemical Diversity and Biological Activity of Secondary Metabolites Isolated from Indonesian Marine Invertebrates

“…Compound 97 was the first dibromopyrrole cyclopeptide with a chlorohistidine ring, while compound 98 possess a rare tribromopyrrole ring. Unfortunately, both compounds did not show significant cytotoxicity against four human tumour cell lines [ 45 ].…”

Antibacterial and Cytotoxic Potential of Two Steroids from the Indonesian Soft Coral Sinularia polydactila

“…These metabolites often show pharmacological activities that are important for producing drug candidates, such as anticancer agents. In continuing our research program aimed to search secondary metabolites from Indonesian marine invertebrates, we recently studied the chemical composition of Indonesian marine invertebrates, such as sponges, soft corals, and ascidians (10)(11)(12). In this context, we analyzed a specimen of the soft coral Sinularia polydactila, which was collected at Lembeh strait in North Sulawesi, Indonesia.…”