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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| Format: | Article |
| Language: | English |
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MDPI AG
2020-07-01
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| Series: | Marine Drugs |
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| Online Access: | https://www.mdpi.com/1660-3397/18/8/396 |
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| author | Rogelio Fernández Asep Bayu Tri Aryono Hadi Santiago Bueno Marta Pérez Carmen Cuevas Masteria Yunovilsa Putra |
| author_facet | Rogelio Fernández Asep Bayu Tri Aryono Hadi Santiago Bueno Marta Pérez Carmen Cuevas Masteria Yunovilsa Putra |
| author_sort | Rogelio Fernández |
| collection | DOAJ |
| description | 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. |
| first_indexed | 2024-03-10T18:09:18Z |
| format | Article |
| id | doaj.art-9d0ee749cbdc4a04917d36eccc132aec |
| institution | Directory Open Access Journal |
| issn | 1660-3397 |
| language | English |
| last_indexed | 2024-03-10T18:09:18Z |
| publishDate | 2020-07-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Marine Drugs |
| spelling | doaj.art-9d0ee749cbdc4a04917d36eccc132aec2023-11-20T08:15:01ZengMDPI AGMarine Drugs1660-33972020-07-0118839610.3390/md18080396Unique Polyhalogenated Peptides from the Marine Sponge <i>Ircinia</i> sp.Rogelio Fernández0Asep Bayu1Tri Aryono Hadi2Santiago Bueno3Marta Pérez4Carmen Cuevas5Masteria Yunovilsa Putra6Natural Products Department, PharmaMar S.A., Pol. Ind. La Mina Norte, Avda. de los Reyes 1, 28770 Colmenar Viejo (Madrid), SpainResearch Center for Biotechnology, Indonesian Institute of Sciences, Jl. Raya Jakarta-Bogor No. Km46, Cibinong, Bogor, Jawa Barat 16911, IndonesiaResearch Center for Oceanography, Indonesian Institute of Sciences, Jl. Pasir Putih I, Ancol Timur, Jakarta 14430, IndonesiaNatural Products Department, PharmaMar S.A., Pol. Ind. La Mina Norte, Avda. de los Reyes 1, 28770 Colmenar Viejo (Madrid), SpainNatural Products Department, PharmaMar S.A., Pol. Ind. La Mina Norte, Avda. de los Reyes 1, 28770 Colmenar Viejo (Madrid), SpainNatural Products Department, PharmaMar S.A., Pol. Ind. La Mina Norte, Avda. de los Reyes 1, 28770 Colmenar Viejo (Madrid), SpainResearch Center for Biotechnology, Indonesian Institute of Sciences, Jl. Raya Jakarta-Bogor No. Km46, Cibinong, Bogor, Jawa Barat 16911, IndonesiaTwo 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.https://www.mdpi.com/1660-3397/18/8/396marine sponge<i>Ircinia</i> sp.polyhalogenated peptidesMarfey’s analysis |
| spellingShingle | Rogelio Fernández Asep Bayu Tri Aryono Hadi Santiago Bueno Marta Pérez Carmen Cuevas Masteria Yunovilsa Putra Unique Polyhalogenated Peptides from the Marine Sponge <i>Ircinia</i> sp. Marine Drugs marine sponge <i>Ircinia</i> sp. polyhalogenated peptides Marfey’s analysis |
| title | Unique Polyhalogenated Peptides from the Marine Sponge <i>Ircinia</i> sp. |
| title_full | Unique Polyhalogenated Peptides from the Marine Sponge <i>Ircinia</i> sp. |
| title_fullStr | Unique Polyhalogenated Peptides from the Marine Sponge <i>Ircinia</i> sp. |
| title_full_unstemmed | Unique Polyhalogenated Peptides from the Marine Sponge <i>Ircinia</i> sp. |
| title_short | Unique Polyhalogenated Peptides from the Marine Sponge <i>Ircinia</i> sp. |
| title_sort | unique polyhalogenated peptides from the marine sponge i ircinia i sp |
| topic | marine sponge <i>Ircinia</i> sp. polyhalogenated peptides Marfey’s analysis |
| url | https://www.mdpi.com/1660-3397/18/8/396 |
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