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A Fish-feeding Laboratory Bioassay to Assess the Antipredatory Activity of Secondary Metabolites from the Tissues of Marine Organisms
Published on: January 11, 2015
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Unique Polyhalogenated Peptides from the Marine Sponge Ircinia sp
Rogelio Fernández1, Asep Bayu2, Tri Aryono Hadi3
1Natural Products Department, PharmaMar S.A., Pol. Ind. La Mina Norte, Avda. de los Reyes 1, 28770 Colmenar Viejo (Madrid), Spain.
Marine Drugs
|August 1, 2020
Summary
Two novel bromopyrrole peptides were isolated from an Indonesian marine sponge. These compounds, haloirciniamide A and seribunamide A, showed no significant anticancer activity or enzyme inhibition.
Area of Science:
- Marine Natural Products Chemistry
- Medicinal Chemistry
- Organic Chemistry
Background:
- Marine sponges, particularly from the genus *Ircinia*, are a rich source of bioactive secondary metabolites.
- Bromopyrrole peptides represent a class of natural products with diverse biological activities.
- The Indonesian archipelago is known for its high marine biodiversity, offering potential for novel compound discovery.
Purpose of the Study:
- To isolate and characterize new bromopyrrole peptides from an Indonesian marine sponge.
- To investigate the potential biological activities of the isolated compounds, including cytotoxicity and enzyme inhibition.
Main Methods:
- Isolation and purification of compounds using chromatographic techniques.
- Structure elucidation employing 1D and 2D Nuclear Magnetic Resonance (NMR) spectroscopy and mass spectrometry.
- Determination of absolute configurations using Marfey's method.
- In vitro assays for cytotoxicity against human tumor cell lines.
- Enzyme inhibition assays for topoisomerase I.
- Assessment of programmed cell death protein 1 (PD1)/programmed cell death ligand 1 (PDL1) interaction.
Main Results:
- Two new bromopyrrole peptides, haloirciniamide A (1) and seribunamide A (2), were successfully isolated.
- The planar structures and absolute configurations of compounds 1 and 2 were determined.
- Compound 1 represents the first reported dibromopyrrole cyclopeptide containing a chlorohistidine ring.
- Compound 2 is a rare peptide characterized by a tribromopyrrole ring.
- Neither compound exhibited significant cytotoxicity against tested human tumor cell lines.
- Compounds 1 and 2 did not inhibit topoisomerase I activity.
- The compounds did not interfere with the programmed cell death protein 1 (PD1) and programmed cell death ligand 1 (PDL1) interaction.
Conclusions:
- The study successfully identified and characterized two novel bromopyrrole peptides from an Indonesian marine sponge.
- Despite their unique structures, haloirciniamide A and seribunamide A demonstrated limited biological activity in the tested assays.
- These findings contribute to the chemical diversity of marine natural products and provide a basis for future structure-activity relationship studies.
