Genome-informed Discovery of Monchicamides A–K: Cyanobactins from the Microcoleaceae Cyanobacterium LEGE 16532
Year: 2024
Type: article
Abstract: High Resolution Image Download MS PowerPoint Slide Genome mining has emerged as an important tool for the discovery of natural products and is particularly effective for the swift identification of ribosomally synthesized and post-translationally modified peptides (RiPPs). Among RiPPs, cyanobactins have gained attention due to their diverse structures and bioactive properties. Here, we explored the Microcoleaceae cyanobacterium LEGE 16532 strain and identified the mon biosynthetic gene cluster (BGC), which was predicted to encode cyanobactin-like molecules. This led to the detection of 11 macrocyclic cyanobactins, the monchicamides, some of which feature mono- or diprenylation. One of the compounds was isolated, monchicamides I ( 9 ), and its planar structure was established by LC-HRESIMS/MS data as well as 1D and 2D NMR spectroscopy, confirming forward O-prenylation in Tyr. In addition, the absolute configuration of compound 9 was determined by Marfey’s method and chiral-phase HPLC. The structures of the additional cyanobactins were proposed from MS/MS data analysis. The bioactivity profile of the isolated compound was also evaluated, but no cytotoxic, antimicrobial, or antiamoebic activity was observed.
Source: Journal of Natural Products
Language: English
Subfield: Pharmacology
Field: Medicine
Domain: Health Sciences
Open Access status: hybrid
Estimated APC paid: $4,500
Awards: G2076412788, G2131988740, Centro Interdisciplinar de Investigação Marinha e Ambiental, G4048552410, BlueBio4Future – Blue Biotechnology and Bioengineering for the Current and Future Development of a Blue Bioeconomy in Portugal, G434337789, CyanoRiPPs: Genome-guided discovery of new peptides in Cyanobacteria, Centro Interdisciplinar de Investigação Marinha e Ambiental, G8050799814
OpenAlex ID: W4405735979