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. 2022 May 6;46(3):fuac007.
doi: 10.1093/femsre/fuac007.

Role is in the eye of the beholder-the multiple functions of the antibacterial compound tropodithietic acid produced by marine Rhodobacteraceae

Nathalie N S E Henriksen  1 , Laura L Lindqvist  1 , Mario Wibowo  1 , Eva C Sonnenschein  1 , Mikkel Bentzon-Tilia  1 , Lone Gram  1
Affiliations

Role is in the eye of the beholder-the multiple functions of the antibacterial compound tropodithietic acid produced by marine Rhodobacteraceae

Nathalie N S E Henriksen et al. FEMS Microbiol Rev. .

Abstract

Many microbial secondary metabolites have been studied for decades primarily because of their antimicrobial properties. However, several of these metabolites also possess nonantimicrobial functions, both influencing the physiology of the producer and their ecological neighbors. An example of a versatile bacterial secondary metabolite with multiple functions is the tropone derivative tropodithietic acid (TDA). TDA is a broad-spectrum antimicrobial compound produced by several members of the Rhodobacteraceae family, a major marine bacterial lineage, within the genera Phaeobacter, Tritonibacter, and Pseudovibrio. The production of TDA is governed by the mode of growth and influenced by the availability of nutrient sources. The antibacterial effect of TDA is caused by disruption of the proton motive force of target microorganisms and, potentially, by its iron-chelating properties. TDA also acts as a signaling molecule, affecting gene expression in other bacteria, and altering phenotypic traits such as motility, biofilm formation, and antibiotic production in the producer. In microbial communities, TDA-producing bacteria cause a reduction of the relative abundance of closely related species and some fast-growing heterotrophic bacteria. Here, we summarize the current understanding of the chemical ecology of TDA, including the environmental niches of TDA-producing bacteria, and the molecular mechanisms governing the function and regulation of TDA.

Keywords: Rhodobacteraceae; antimicrobials; marine microbiomes; secondary metabolites; tropodithietic acid.

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Figures

Figure 1.
Figure 1.
Proposal for three functions of TDA and potential ecological roles. Bold text indicate functions. Nonbold text indicate potential ecological roles. Created with Biorender.com.
Figure 2.
Figure 2.
TDA and its tautomers (upper panel) and analogues (lower panel). Created with ChemDraw Professional (PerkinElmer Informatics).
Figure 3.
Figure 3.
TDA biosynthesis and genes responsible for TDA production. (A) Biosynthetic genes involved in TDA biosynthesis in P. inhibens DSM17395. paaABCDEIJK1K2 and patB (in green) are located on the chromosome, whilst tdaABCDEF and paaZ2 (in blue) are located on a 262-kb megaplasmid. (B) TDA biosynthesis draws on primary metabolism for formation of the carbon backbone. Phenylacetic acid, 1, is converted to 2 by PaaK, PaaABC(D)E, and PaaG. PaaZ-ECH or PaaZ2 catalyzes hydrolytic ring cleavage to form 3, which is then either converted to 9 by the ALDH domain of PaaZ or spontaneously cyclized to 4. TdaE then connects primary and secondary metabolism through a series of reactions: dehydrogenation to 5, CoA-ester oxygenolysis to 6, and ring epoxidation to form 7. TdaBCDF subsequently forms TDA, 8. Stipled lines indicate multiple reactions taking place. Created with ChemDraw Professional (PerkinElmer Informatics) and Biorender.com.
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