Preprint Article Version 1 Preserved in Portico This version is not peer-reviewed

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

Subhasish Saha
,
Germana Esposito
ORCID logo ,
Petra Urajova
,
Jan Mareš
,
Daniela Ewe
,
Alessia Caso
ORCID logo ,
Marketa Macho
,
Katerina Delawska
,
Andreja Kust
,
Pavel Hrouzek
,
Josef Juran
,
Valeria Costantino
* ORCID logo ,
Kumar Saurav
*
Version 1 : Received: 22 July 2020 / Approved: 23 July 2020 / Online: 23 July 2020 (12:40:38 CEST)

How to cite: Saha, S.; Esposito, G.; Urajova, P.; Mareš, J.; Ewe, D.; Caso, A.; Macho, M.; Delawska, K.; Kust, A.; Hrouzek, P.; Juran, J.; Costantino, V.; Saurav, K. Discovery of Unusual Cyanobacterial Tryptophan-containing Anabaenopeptins by MS/MS Based Molecular Networking. Preprints 2020, 2020070562. https://doi.org/10.20944/preprints202007.0562.v1 Saha, S.; Esposito, G.; Urajova, P.; Mareš, J.; Ewe, D.; Caso, A.; Macho, M.; Delawska, K.; Kust, A.; Hrouzek, P.; Juran, J.; Costantino, V.; Saurav, K. Discovery of Unusual Cyanobacterial Tryptophan-containing Anabaenopeptins by MS/MS Based Molecular Networking. Preprints 2020, 2020070562. https://doi.org/10.20944/preprints202007.0562.v1

Abstract

Heterocytous cyanobacteria are among the most prolific source of bioactive secondary metabolites, including anabaenopeptins (APTs). A terrestrial filamentous Brasilonema sp. CT11 collected in Costa Rica bamboo forest, as black mat was studied using a multidisciplinary approach: genome mining and HPLC-HRMS/MS coupled with bionformatic analyses. Herein, we report the nearly complete genome consisting 8.79 Mbp with a GC content of 42.4%. Moreover, we report on three novel tryptophane-containing APTs; anabaenopeptin 788 (1), anabaenopeptin 802 (2) and anabaenopeptin 816 (3). Further, 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.

Keywords

Brasilonema; Anabaenopeptins; hexapeptides; tryptophan-containing peptides; molecular networking; antiproliferative activity

Subject

Chemistry and Materials Science, Analytical Chemistry

Copyright: This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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