Chemistry, bioactivity and biosynthesis of cyanobacterial alkylresorcinols

Martins, Teresa P., Rouger, Caroline, Glasser, Nathaniel R., Freitas, Sara, de Fraissinette, Nelly B., Balskus, Emily P., Tasdemir, Deniz and Leão, Pedro N. (2019) Chemistry, bioactivity and biosynthesis of cyanobacterial alkylresorcinols Natural Product Reports, 36 (10). pp. 1437-1461. DOI 10.1039/c8np00080h.

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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.

Document Type: Article
Research affiliation: OceanRep > GEOMAR > FB3 Marine Ecology > FB3-MN Marine natural products chemistry
Refereed: Yes
DOI etc.: 10.1039/c8np00080h
ISSN: 0265-0568
Date Deposited: 01 Feb 2019 08:41
Last Modified: 24 Oct 2019 08:46

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