Expanding the Diversity of the Cyanobacterial Dialkylresorcinol Bartoloside Family.

J Nat Prod

CIIMAR - Interdisciplinary Centre of Marine and Environmental Research, University of Porto, Matosinhos 4450-208, Portugal.

Published: December 2024

AI Article Synopsis

  • Researchers studied cyanobacterial dialkylresorcinol bartolosides, initially thought to have glycosylated and halogenated structures.
  • They found that these compounds can form esters through a process involving chlorinated alkyl chains and fatty acids, leading to a variety of bartoloside derivatives.
  • The study identified 27 bartoloside and ester variants, including two new types, and revealed new structural features like hydroxylation that were not previously linked to this metabolite group.

Article Abstract

The cyanobacterial dialkylresorcinol bartolosides were initially reported to feature glycosylated and halogenated moieties. Later, biosynthetic and studies showed that the chlorinated alkyl chains are utilized for a nucleophilic substitution with free fatty acid carboxylates from primary metabolism, generating bartoloside esters. Here, we applied a workflow based on PCR screening coupled to LC-HRESIMS and molecular network analysis with the aim of discovering additional bartoloside diversity. We report the annotation of 27 bartoloside and bartoloside ester derivatives, including the characterization of two new bartolosides, underlining the breadth of structures generated by bartoloside biosynthetic pathways. Some of the herein reported bartolosides feature hydroxylation in their side chains, a modification that has not been associated with this metabolite family.

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http://dx.doi.org/10.1021/acs.jnatprod.4c00832DOI Listing

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CIIMAR - Interdisciplinary Centre of Marine and Environmental Research, University of Porto, Matosinhos 4450-208, Portugal.

Article Synopsis
  • Researchers studied cyanobacterial dialkylresorcinol bartolosides, initially thought to have glycosylated and halogenated structures.
  • They found that these compounds can form esters through a process involving chlorinated alkyl chains and fatty acids, leading to a variety of bartoloside derivatives.
  • The study identified 27 bartoloside and ester variants, including two new types, and revealed new structural features like hydroxylation that were not previously linked to this metabolite group.
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