Discovery of Unusual Cyanobacterial Tryptophan-Containing Anabaenopeptins by MS/MS-Based Molecular Networking.
Subhasish SahaGermana EspositoPetra UrajováJan MarešDaniela EweAlessia CasoMarkéta MachoKateřina DelawskáAndreja KustPavel HrouzekJosef JuráňValeria CostantinoKumar SauravPublished in: Molecules (Basel, Switzerland) (2020)
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.
Keyphrases
- ms ms
- genome wide
- liquid chromatography tandem mass spectrometry
- mass spectrometry
- computed tomography
- small molecule
- magnetic resonance
- climate change
- high resolution
- molecular docking
- gene expression
- image quality
- high throughput
- copy number
- high intensity
- contrast enhanced
- magnetic resonance imaging
- dna methylation
- gas chromatography
- positron emission tomography
- dual energy
- quality improvement
- cell proliferation
- human health
- signaling pathway
- cell cycle arrest