Controlling bacterial behavior with indole-containing natural products and derivatives

Melander, Roberta J.; Minvielle, Marine J.; Melander, Christian

doi:10.1016/j.tet.2014.05.089

Cited by 110 publications

(46 citation statements)

References 77 publications

(115 reference statements)

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“…Despite not being the main aim of this study, other relevant and encouraging data were also found that warrant future investigations, such as the higher sensitivity of the DiaaM mutant to oxytetracycline and the higher resistance of the DhrpA mutant to hydroxylamine, sodium azide and polymixin B, in comparison to the wild-type Psn23. In conclusion, taken together, these findings provide information for the development of alternative strategies to control pathogenic bacteria through the use of natural products containing indolebased molecules [77].…”

Section: Discussionmentioning

confidence: 66%

Indole-3-acetic acid in plant–pathogen interactions: a key molecule for in planta bacterial virulence and fitness

Cerboneschi

Decorosi

Biancalani

et al. 2016

Research in Microbiology

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The plant pathogenic bacterium Pseudomonas savastanoi, the causal agent of olive and oleander knot disease, uses the so-called "indole-3-acetamide pathway" to convert tryptophan to indole-3-acetic acid (IAA) via a two-step pathway catalyzed by enzymes encoded by the genes in the iaaM/iaaH operon. Moreover, pathovar nerii of P. savastanoi is able to conjugate IAA to lysine to generate the less biologically active compound IAA-Lys via the enzyme IAA-lysine synthase encoded by the iaaL gene. Interestingly, iaaL is now known to be widespread in many Pseudomonas syringae pathovars, even in the absence of the iaaM and iaaH genes for IAA biosynthesis.Here, two knockout mutants, DiaaL and DiaaM, of strain Psn23 of P. savastanoi pv. nerii were produced. Pathogenicity tests using the host plant Nerium oleander showed that DiaaL and DiaaM were hypervirulent and hypovirulent, respectively and these features appeared to be related to their differential production of free IAA. Using the Phenotype Microarray approach, the chemical sensitivity of these mutants was shown to be comparable to that of wild-type Psn23. The main exception was 8 hydroxyquinoline, a toxic compound that is naturally present in plant exudates and is used as a biocide, which severely impaired the growth of DiaaL and DiaaM, as well as growth of the non-pathogenic mutant DhrpA, which lacks a functional Type Three Secretion System (TTSS). According to bioinformatics analysis of the Psn23 genome, a gene encoding a putative Multidrug and Toxic compound Extrusion (MATE) transporter, was found upstream of iaaL. Similarly to iaaL and iaaM, its expression appeared to be TTSS-dependent. Moreover, auxin-responsive elements were identified for the first time in the modular promoters of both the iaaL gene and the iaaM/iaaH operon of P. savastanoi, suggesting their IAA-inducible transcription. Gene expression analysis of several genes related to TTSS, IAA metabolism and drug resistance confirmed the presence of a concerted regulatory network in this phytopathogen among virulence, fitness and drug efflux.

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Section: Discussionmentioning

confidence: 66%

Indole-3-acetic acid in plant–pathogen interactions: a key molecule for in planta bacterial virulence and fitness

Cerboneschi

Decorosi

Biancalani

et al. 2016

Research in Microbiology

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“…These results indicate that the production of amino acid metabolites affects the composition of gut microbiota. Yet, the precursor of IS (indole) controls diverse aspects of bacterial processes, including spore formation, plasmid stability, antibiotic resistance, bacterial persister formation, biofilm formation, and maintenance [26,27]. In allogeneic stem cell transplantation patients, the urinary level of microbiota-derived indole and metabolites associated with microbiota diversity influences mucosal integrity and provides protection from inflammation [28].…”

Section: Discussionmentioning

confidence: 99%

Uremic Toxin-Producing Gut Microbiota in Rats with Chronic Kidney Disease

Kikuchi

Ueno

Itoh

et al. 2016

Nephron

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Background: In patients with chronic kidney disease (CKD), many metabolites of gut microbiota retain in the body as uremic toxins (UTs). However, the kinds of bacteria producing UTs are rarely discussed. Methods: We analyzed UT production and the composition of gut microbiota in CKD rats and cecectomized rats. AST-120, a spherical carbon adsorbent, was administrated to evaluate how the precursors of UT affect gut microbiota. Serum and urine levels of UTs were quantified by liquid chromatography/electrospray ionization-tandem mass spectrometry. Gut microbiota were analyzed using 454-pyrosequencing of the 16S rRNA gene. Operational taxonomic unit (OTU) clustering and UniFrac analysis were performed to compare gut microbiota among the groups. Results: Serum and urine levels of indoxyl sulfate and phenyl sulfate were higher in CKD versus control rats (p < 0.05). AST-120 administration decreased UT production (p < 0.01) and changed overall gut microbiota composition in CKD rats. UT urinary excretion and gut microbiota composition changed in cecectomized rats, with the relative abundance of Clostridia- and Bacteroidia-affiliated species being significantly reduced (p < 0.01). We identified candidate indole- and phenol-producing intestinal microbiota, 3 Clostridia, and 2 Bacteroidia. These OTUs have a tryptophanase/tyrosine phenol-lyase gene in the closest sequenced genome out of the OTUs declined following cecectomy. Conclusion: Our data suggest that UT production is correlated with a subset of indigenous gut microbiota. However, UT may be induced by other non-symbiotic microbiota that are influenced by factors other than microbiota populations. The relationship between specific microbiota and UTs in patients requires further clarification.

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“…In another study, the brominated furanone motif and indole were combined to produce desformylflustrabromine, which inhibited biofilm formation by S. aureus and E. coli [45], and the N-acylated L-homoserine lactone motif and indole were combined to inhibit P. aeruginosa QS [69]. Recently, two review papers described indole-containing small molecules that modulate bacterial behaviors and the synthetic approaches they used [29,30]. Since thousands of natural and synthetic indole derivatives have been identified, it would be interesting to investigate indole structure-activity relationships and determine how indole derivatives affect bacterial pathogenicity and antibiotic resistance.…”

Section: Antivirulence Activities Of Indoles Against Non-indole-produmentioning

confidence: 99%

“…A small number of reviews have summarized the biological roles of indole, mostly in indoleproducing bacteria [27,28], or the approaches used to synthesize indole-based small molecules [29,30]. In this review, we discuss current knowledge of indole and its derivatives in indoleproducing bacteria, in non-indole-producing pathogenic bacteria, and in eukaryotic systems (such as animals, plants, insects, and nematodes); potential biotechnological applications of indoles are also discussed.…”

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confidence: 99%