Discovery of Unusual Cyanobacterial Tryptophan-Containing Anabaenopeptins by MS/MS-Based Molecular Networking
Heterocytous cyanobacteria are among the most prolific sources of bioactive secondary metabolites, including anabaenopeptins (APTs). A terrestrial filamentous <i>Brasilonema</i> sp. CT11 collected in Costa Rica bamboo forest as a black mat, was studied using a multidisciplinary approach:...
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| Format: | Article |
| Language: | English |
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MDPI AG
2020-08-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/25/17/3786 |
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| author | Subhasish Saha Germana Esposito Petra Urajová Jan Mareš Daniela Ewe Alessia Caso Markéta Macho Kateřina Delawská Andreja Kust Pavel Hrouzek Josef Juráň Valeria Costantino Kumar Saurav |
| author_facet | Subhasish Saha Germana Esposito Petra Urajová Jan Mareš Daniela Ewe Alessia Caso Markéta Macho Kateřina Delawská Andreja Kust Pavel Hrouzek Josef Juráň Valeria Costantino Kumar Saurav |
| author_sort | Subhasish Saha |
| collection | DOAJ |
| description | Heterocytous cyanobacteria are among the most prolific sources of bioactive secondary metabolites, including anabaenopeptins (APTs). A terrestrial filamentous <i>Brasilonema</i> sp. CT11 collected in Costa Rica bamboo forest as a black mat, was studied using a multidisciplinary approach: genome mining and HPLC-HRMS/MS coupled with bioinformatic analyses. Herein, we report the nearly complete genome consisting of 8.79 Mbp with a GC content of 42.4%. Moreover, we report on three novel tryptophan-containing APTs; anabaenopeptin 788 (<b>1</b>), anabaenopeptin 802 (<b>2</b>), and anabaenopeptin 816 (<b>3</b>). Furthermore, the structure of two homologues, i.e., anabaenopeptin 802 (<b>2a</b>) and anabaenopeptin 802 (<b>2b</b>), was determined by spectroscopic analysis (NMR and MS). Both compounds were shown to exert weak to moderate antiproliferative activity against HeLa cell lines. This study also provides the unique and diverse potential of biosynthetic gene clusters and an assessment of the predicted chemical space yet to be discovered from this genus. |
| first_indexed | 2024-03-10T17:07:40Z |
| format | Article |
| id | doaj.art-30f4f1fc6d1947729a354bda4dceeae8 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-10T17:07:40Z |
| publishDate | 2020-08-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-30f4f1fc6d1947729a354bda4dceeae82023-11-20T10:45:26ZengMDPI AGMolecules1420-30492020-08-012517378610.3390/molecules25173786Discovery of Unusual Cyanobacterial Tryptophan-Containing Anabaenopeptins by MS/MS-Based Molecular NetworkingSubhasish Saha0Germana Esposito1Petra Urajová2Jan Mareš3Daniela Ewe4Alessia Caso5Markéta Macho6Kateřina Delawská7Andreja Kust8Pavel Hrouzek9Josef Juráň10Valeria Costantino11Kumar Saurav12Laboratory of Algal Biotechnology-Centre Algatech, Institute of Microbiology of the Czech Academy of Sciences, 37981 Třeboň, Czech RepublicTask Force Big Fed2, The Blue Chemistry lab, Università degli Studi di Napoli, 80131 Napoli, ItalyLaboratory of Algal Biotechnology-Centre Algatech, Institute of Microbiology of the Czech Academy of Sciences, 37981 Třeboň, Czech RepublicLaboratory of Algal Biotechnology-Centre Algatech, Institute of Microbiology of the Czech Academy of Sciences, 37981 Třeboň, Czech RepublicLaboratory of Algal Biotechnology-Centre Algatech, Institute of Microbiology of the Czech Academy of Sciences, 37981 Třeboň, Czech RepublicTask Force Big Fed2, The Blue Chemistry lab, Università degli Studi di Napoli, 80131 Napoli, ItalyLaboratory of Algal Biotechnology-Centre Algatech, Institute of Microbiology of the Czech Academy of Sciences, 37981 Třeboň, Czech RepublicLaboratory of Algal Biotechnology-Centre Algatech, Institute of Microbiology of the Czech Academy of Sciences, 37981 Třeboň, Czech RepublicLaboratory of Algal Biotechnology-Centre Algatech, Institute of Microbiology of the Czech Academy of Sciences, 37981 Třeboň, Czech RepublicLaboratory of Algal Biotechnology-Centre Algatech, Institute of Microbiology of the Czech Academy of Sciences, 37981 Třeboň, Czech RepublicFaculty of Science, University of South Bohemia in České Budějovice, Branišovská 1760, 37005 České Budějovice, Czech RepublicTask Force Big Fed2, The Blue Chemistry lab, Università degli Studi di Napoli, 80131 Napoli, ItalyLaboratory of Algal Biotechnology-Centre Algatech, Institute of Microbiology of the Czech Academy of Sciences, 37981 Třeboň, Czech RepublicHeterocytous cyanobacteria are among the most prolific sources of bioactive secondary metabolites, including anabaenopeptins (APTs). A terrestrial filamentous <i>Brasilonema</i> sp. CT11 collected in Costa Rica bamboo forest as a black mat, was studied using a multidisciplinary approach: genome mining and HPLC-HRMS/MS coupled with bioinformatic analyses. Herein, we report the nearly complete genome consisting of 8.79 Mbp with a GC content of 42.4%. Moreover, we report on three novel tryptophan-containing APTs; anabaenopeptin 788 (<b>1</b>), anabaenopeptin 802 (<b>2</b>), and anabaenopeptin 816 (<b>3</b>). Furthermore, the structure of two homologues, i.e., anabaenopeptin 802 (<b>2a</b>) and anabaenopeptin 802 (<b>2b</b>), was determined by spectroscopic analysis (NMR and MS). Both compounds were shown to exert weak to moderate antiproliferative activity against HeLa cell lines. This study also provides the unique and diverse potential of biosynthetic gene clusters and an assessment of the predicted chemical space yet to be discovered from this genus.https://www.mdpi.com/1420-3049/25/17/3786<i>Brasilonema</i>anabaenopeptinshexapeptidestryptophan-containing peptidesmolecular networkingantiproliferative activity |
| spellingShingle | Subhasish Saha Germana Esposito Petra Urajová Jan Mareš Daniela Ewe Alessia Caso Markéta Macho Kateřina Delawská Andreja Kust Pavel Hrouzek Josef Juráň Valeria Costantino Kumar Saurav Discovery of Unusual Cyanobacterial Tryptophan-Containing Anabaenopeptins by MS/MS-Based Molecular Networking Molecules <i>Brasilonema</i> anabaenopeptins hexapeptides tryptophan-containing peptides molecular networking antiproliferative activity |
| title | Discovery of Unusual Cyanobacterial Tryptophan-Containing Anabaenopeptins by MS/MS-Based Molecular Networking |
| title_full | Discovery of Unusual Cyanobacterial Tryptophan-Containing Anabaenopeptins by MS/MS-Based Molecular Networking |
| title_fullStr | Discovery of Unusual Cyanobacterial Tryptophan-Containing Anabaenopeptins by MS/MS-Based Molecular Networking |
| title_full_unstemmed | Discovery of Unusual Cyanobacterial Tryptophan-Containing Anabaenopeptins by MS/MS-Based Molecular Networking |
| title_short | Discovery of Unusual Cyanobacterial Tryptophan-Containing Anabaenopeptins by MS/MS-Based Molecular Networking |
| title_sort | discovery of unusual cyanobacterial tryptophan containing anabaenopeptins by ms ms based molecular networking |
| topic | <i>Brasilonema</i> anabaenopeptins hexapeptides tryptophan-containing peptides molecular networking antiproliferative activity |
| url | https://www.mdpi.com/1420-3049/25/17/3786 |
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