Chemistry, bioactivity and biosynthesis of cyanobacterial alkylresorcinols. Issue 10 (31st January 2019)

• Record Type: Journal Article
• Authors: Martins, Teresa P.; Rouger, Caroline; Glasser, Nathaniel R.; Freitas, Sara; de Fraissinette, Nelly B.; Balskus, Emily P.; Tasdemir, Deniz; Leão, Pedro N.
• Is Part Of: Natural product reports. Volume 36:Issue 10(2019)
• Page Start: 1437
• Page End: 1461
• Publication Date: 2019-01-31
• Subjects: Natural products -- Periodicals; Produits naturels -- Périodiques; 547.7
• DOI: 10.1039/c8np00080h
• Languages: English
• ISSNs: 0265-0568

Abstract

Abstract : This review covers the structure, synthesis, biological activity, biosynthesis and distribution of cyanobacterial alkylresorcinols. Abstract : 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.