Unique Polyhalogenated Peptides from the Marine Sponge Ircinia sp.

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

doi:10.3390/md18080396

Rogelio Fernández, Marta Pérez + Show 5 more

Open Access

https://doi.org/10.3390/md18080396

Copy DOI

Journal: Marine Drugs	Publication Date: Jul 28, 2020
Citations: 12	License type: CC BY 4.0

Affiliation: PharmaMar (Spain), Indonesian Institute of Sciences

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.

Highlights

Indonesia is located at the center of a biodiversity hotspot, and around 750 structures fromIndonesian waters have been published in the last 50 years [1]
Previous reports revealed that Marine sponges of the genus Ircinia are known as a rich source of varied bioactive natural products, including fatty acids [3], steroids [4,5], terpenes [6,7], macrolides [8,9], and peptides [10], many of which have biological activities
Seribunamide A (2), were isolated from a marine sponge belonging to the Irnicia genus, which was selected for further studies

Summary

Introduction

Indonesia is located at the center of a biodiversity hotspot, and around 750 structures fromIndonesian waters have been published in the last 50 years [1]. Previous reports revealed that Marine sponges of the genus Ircinia are known as a rich source of varied bioactive natural products, including fatty acids [3], steroids [4,5], terpenes [6,7], macrolides [8,9], and peptides [10], many of which have biological activities. This structural diversity could be due to the fact that sponges harbor diverse microorganisms and in numerous cases, bacteria

Methods

Results

Conclusion