Production of bioactive secondary metabolites by marine vibrionaceae

Abstract

Bacteria belonging to the Vibrionaceae family are widespread in the marine environment. Today, 128 species of vibrios are known. Several of them are infamous for their pathogenicity or symbiotic relationships. Despite their ability to interact with eukaryotes, the vibrios are greatly underexplored for their ability to produce bioactive secondary metabolites and studies have been limited to only a few species. Most of the compounds isolated from vibrios so far are non-ribosomal peptides or hybrids thereof, with examples of N-containing compounds produced independent of nonribosomal peptide synthetases (NRPS). Though covering a limited chemical space, vibrios produce compounds with attractive biological activities, including antibacterial, anticancer, and antivirulence activities. This review highlights some of the most interesting structures from this group of bacteria. Many compounds found in vibrios have also been isolated from other distantly related bacteria. This cosmopolitan occurrence of metabolites indicates a high incidence of horizontal gene transfer, which raises interesting questions concerning the ecological function of some of these molecules. This account underlines the pending potential for exploring new bacterial sources of bioactive compounds and the challenges related to their investigation.

Keywords: Vibrio; antibiotics; bioactive; marine bacteria; siderophores.

Figure 1

Evolutionary relationship of the Vibrionaceae family [–7].

Figure 2

Structures common quorum sensing molecules from Vibrio sp.

Figure 3

LC-MS profiles of a V. coralliilyticus (A) and V. neptunius (B), showing significant differences in secondary metabolite production. Andrimid (RT 10.02) was only found in V. coralliilyticus strains. Figure modified from Wietz et al. (2010) [45].

Figure 4

Structure of andrimid isolated from Vibrio coralliilyticus.

Figure 5

Structure of holomycin isolated from Photobacterium halotolerans.

Figure 6

Structures of aqabamycin A–G isolated from coral-associated Vibrio sp.

Figure 7

Structures of prodigiosins and magnesidin.

Figure 8

Cyclodepsipeptides isolated from Photobacterium sp.

Figure 9

Siderophores isolated from Vibrio sp.

Figure 10

Structure of kahalalide F isolated from Vibrio mediterranei/shilonii.

Figure 11

Structure of tetrodotoxin isolated from Vibrio harveyi and Vibrio alginolyticus.

Figure 12

Structures of solonamides isolated from Photobacterium halotolerans related strain.

Figure 13

Structures of common diketopiperazines from Vibrio sp. and [1-(2′-methylpropoxy)-2-hydroxy-2-methylpropoxy]-butane.

Figure 14

Structures of cyclotetrapeptides isolated from Photobacterium.

Figure 15

Structures of 1,1,1-tris (3-indolyl) methane and pharacine, examples of potential artefacts from work-up of Vibrio extracts.