Cyclopropane-Containing Fatty Acids from the Marine Bacterium Labrenzia sp. 011 with Antimicrobial and GPR84 Activity

Mar Drugs. 2018 Oct 8;16(10):369. doi: 10.3390/md16100369.

Abstract

Bacteria of the family Rhodobacteraceae are widespread in marine environments and known to colonize surfaces, such as those of e.g., oysters and shells. The marine bacterium Labrenzia sp. 011 is here investigated and it was found to produce two cyclopropane-containing medium-chain fatty acids (1, 2), which inhibit the growth of a range of bacteria and fungi, most effectively that of a causative agent of Roseovarius oyster disease (ROD), Pseudoroseovarius crassostreae DSM 16950. Additionally, compound 2 acts as a potent partial, β-arrestin-biased agonist at the medium-chain fatty acid-activated orphan G-protein coupled receptor GPR84, which is highly expressed on immune cells. The genome of Labrenzia sp. 011 was sequenced and bioinformatically compared with those of other Labrenzia spp. This analysis revealed several cyclopropane fatty acid synthases (CFAS) conserved in all Labrenzia strains analyzed and a putative gene cluster encoding for two distinct CFASs is proposed as the biosynthetic origin of 1 and 2.

Keywords: Aliiroseovarius crassostreae; GPR84; Labrenzia; Pseudoroseovarius crassostreae; Roseovarius crassostreae; Roseovarius oyster disease; antimicrobials; bioinformatics; cyclopropane containing fatty acids; inflammation.

MeSH terms

  • Animals
  • Anti-Bacterial Agents / metabolism
  • Anti-Bacterial Agents / pharmacology*
  • Aquatic Organisms / metabolism*
  • Cyclopropanes / metabolism
  • Cyclopropanes / pharmacology*
  • Fatty Acids / metabolism
  • Fatty Acids / pharmacology*
  • Methyltransferases / metabolism
  • Ostreidae / microbiology
  • Receptors, Cell Surface / metabolism*
  • Rhodobacteraceae / metabolism*
  • beta-Arrestins / metabolism

Substances

  • Anti-Bacterial Agents
  • Cyclopropanes
  • Fatty Acids
  • Receptors, Cell Surface
  • beta-Arrestins
  • cyclopropane
  • Methyltransferases
  • cyclopropane synthetase