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Open AccessArticle

Discovery of Unusual Cyanobacterial Tryptophan-Containing Anabaenopeptins by MS/MS-Based Molecular Networking

1
Laboratory of Algal Biotechnology-Centre Algatech, Institute of Microbiology of the Czech Academy of Sciences, 37981 Třeboň, Czech Republic
2
Task Force Big Fed2, The Blue Chemistry lab, Università degli Studi di Napoli, 80131 Napoli, Italy
3
Institute of Hydrobiology, Biology Centre of the Czech Academy of Sciences, 37005 České Budějovice, Czech Republic
4
Faculty of Science, University of South Bohemia in České Budějovice, Branišovská 1760, 37005 České Budějovice, Czech Republic
5
Institute of Botany of the Czech Academy of Sciences, 252 43 Průhonice, Czech Republic
*
Authors to whom correspondence should be addressed.
These authors contributed equally to this work.
Academic Editor: Derek J. McPhee
Molecules 2020, 25(17), 3786; https://doi.org/10.3390/molecules25173786
Received: 21 July 2020 / Revised: 11 August 2020 / Accepted: 19 August 2020 / Published: 20 August 2020
(This article belongs to the Special Issue Alternative Drug Therapy-Cyanobacterial Metabolites)
Heterocytous cyanobacteria are among the most prolific sources of bioactive secondary metabolites, including anabaenopeptins (APTs). A terrestrial filamentous Brasilonema 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 (1), anabaenopeptin 802 (2), and anabaenopeptin 816 (3). Furthermore, the structure of two homologues, i.e., anabaenopeptin 802 (2a) and anabaenopeptin 802 (2b), 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. View Full-Text
Keywords: Brasilonema; anabaenopeptins; hexapeptides; tryptophan-containing peptides; molecular networking; antiproliferative activity Brasilonema; anabaenopeptins; hexapeptides; tryptophan-containing peptides; molecular networking; antiproliferative activity
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Saha, S.; Esposito, G.; Urajová, P.; Mareš, J.; Ewe, D.; Caso, A.; Macho, M.; Delawská, K.; Kust, A.; Hrouzek, P.; Juráň, J.; Costantino, V.; Saurav, K. Discovery of Unusual Cyanobacterial Tryptophan-Containing Anabaenopeptins by MS/MS-Based Molecular Networking. Molecules 2020, 25, 3786.

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