Chemistry, bioactivity and biosynthesis of cyanobacterial alkylresorcinols
2019
Martins, T.P. | Rouger, C | Glasser, N.R | Freitas, S | De Fraissinette, N.B | Balskus, E.P | Tasdemir, D | Leão, P.N. | Centro Interdisciplinar de Investigação Marinha e Ambiental
Covering: up to 2019 Alkylresorcinols are amphiphilic metabolites, well-known for their diverse biological activities, produced by both prokaryotes and eukaryotes. A few classes of alkylresorcinol scaffolds have been reported from the photoautotrophic cyanobacteria, ranging from the relatively simple hierridins to the more intricate cylindrocyclophanes. Recently, it has emerged that cyanobacteria employ two different biosynthetic pathways to produce unique alkylresorcinol scaffolds. However, these convergent pathways intersect by sharing biosynthetic elements which lead to common structural motifs. To obtain a broader view of the biochemical diversity of these compounds in cyanobacteria, we comprehensively cover the isolation, structure, biological activity and biosynthesis of their mono- and dialkylresorcinols. Moreover, we provide an overview of the diversity and distribution of alkylresorcinol-generating biosynthetic gene clusters in this phylum and highlight opportunities for discovery of novel alkylresorcinol scaffolds. Because some of these molecules have inspired notable syntheses, different approaches used to build these molecules in the laboratory are showcased. © The Royal Society of Chemistry.
Show more [+] Less [-]This work was funded by the BLUEandGREEN project (H2020 TWINNING, Grant Agreement no. 692419) and was further supported by an European Research Council (ERC) Starting Grant (759840) to PNL and National Science Foundation (NSF) through grant CHE-1454007 to EPB. We acknowledge funding by Fundação para a Ciência e a Tecnologia (FCT) through projects PTDC/BIA-BQM/29710/2017 (co-financed by COMPETE 2020, Portugal 2020, ERDF) UID/Multi/04423/2013, as well as through scholarship SFRH/BD116009/2016 to SF and grant IF/ 01358/2014 to PNL.
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