Structure Revision of <i>N</i>-Mercapto-4-formylcarbostyril Produced by <i>Pseudomonas fluorescens</i> G308 to 2-(2-Hydroxyphenyl)thiazole-4-carbaldehyde [aeruginaldehyde]

Ye, Lumeng; Cornélis, Pierre; Guillemyn, Karel; Ballet, Steven; Christophersen, Carsten; Hammerich, Ole

doi:10.1177/1934578x1400900615

Cited by 24 publications

(35 citation statements)

References 46 publications

(77 reference statements)

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“…Interestingly, genes associated with all four systems were induced by RA, as exemplified by the lasI, rhlI, the pqs genes involved in quinolone synthesis and the amb genes that have been implicated in IQS signalling (Lee et al, 2013; Table 1). Another study suggested that the IQS signal molecule is a byproduct of the pyochelin biosynthesis pathway (Ye et al, 2014). However, the corresponding operon was not amongst the RA induced genes.…”

Section: Discussionmentioning

confidence: 99%

The plant compound rosmarinic acid induces a broad quorum sensing response in Pseudomonas aeruginosa PAO1

Fernández

Corral-Lugo

Krell

2018

Environmental Microbiology

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The interference of plant compounds with bacterial quorum sensing (QS) is a major mechanism through which plants and bacteria communicate. However, little is known about the modes of action and effects on signal integrity during this type of communication. We have recently shown that the plant compound rosmarinic acid (RA) specifically binds to the Pseudomonas aeruginosa RhlR QS receptor. To determine the effect of RA on expression patterns, we carried out global RNA-seq analysis. The results show that RA induces the expression of 128 genes, amongst which many virulence factor genes. RA triggers a broad QS response because 88% of the induced genes are known to be controlled by QS, and because RA stimulated genes were found to be involved in all four QS signalling systems within P. aeruginosa. This finding was confirmed through the analysis of transcriptional fusions transferred to wt and a rhlI/lasI double mutant. RA did not induce gene expression in the rhlI/lasI/rhlR triple mutant indicating that the effects observed are due to the RA-RhlR interaction. Furthermore, RA induced seven sRNAs that were all encoded in regions close to QS and/or RA induced genes. This work significantly enhances our understanding of plant bacteria interaction.

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Section: Discussionmentioning

confidence: 99%

The plant compound rosmarinic acid induces a broad quorum sensing response in Pseudomonas aeruginosa PAO1

Fernández

Corral-Lugo

Krell

2018

Environmental Microbiology

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“…Finally, the attachment of the thiazole ring to the phenyl group was exhibited through C-1 -C-5 bonding through the HMBC correlations of H-2 to C-5 and C-1 and H-5 to C-1 (Figure 4). The final structure was unambiguously explained the reported compound aeruginaldehyde [17]. Aeruginaldehyde was introduced by Ye et al as a structure revision of N-mercapto-4-formyl carbostyril isolated from Pseudomonas fluorescences as an antibiotic against plant pathogens [17,18].…”

Section: Structure Characterisation Of the Isolated Compoundsmentioning

confidence: 85%

“…and Fusarium spp. [17,18]. Sulfur-containing bio-chemicals are available in all organisms in forms of primary as well as in SMs.…”

Section: Discussionmentioning

confidence: 99%

“…The signals for aromatic protons were observed at (δ H 8.19 (1H, dd (6.1, 1.8) H-2 ], (δ H 7.07 (1H, dd (7.5, 1.4) H-3 ), δ H 7.37 (1H, t (7.54) H-4 ) and (δ H 6.99 (1H, t (7.54) H-5 ), and their respective carbons, C-2 (δ C 127.9), C-3 (δ C 116.9), C-4 (δ C 132.1), and C-5 (δ C 120.0), were assigned by the correlations in the HSQC spectrum. The possibility of a thiazole ring being one of the substituents to the benzene ring was identified during the dereplication process followed by the literature data survey for the aeruginaldehyde that was the most probable hit [17].…”

Section: Structure Characterisation Of the Isolated Compoundsmentioning

confidence: 99%

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Induction of Cryptic Antifungal Pulicatin Derivatives from Pantoea Agglomerans by Microbial Co-Culture

et al. 2020

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Microbial co-culture or mixed fermentation proved to be an efficient strategy to expand chemical diversity by the induction of cryptic biosynthetic pathways, and in many cases led to the production of new antimicrobial agents. In the current study, we report a rare example of the induction of silent/cryptic bacterial biosynthetic pathway by the co-culture of Durum wheat plant roots-associated bacterium Pantoea aggolomerans and date palm leaves-derived fungus Penicillium citrinum. The initial co-culture indicated a clear fungal growth inhibition which was confirmed by the promising antifungal activity of the co-culture total extract against Pc. LC-HRMS chemical profiling demonstrated a huge suppression in the production of secondary metabolites (SMs) of axenic cultures of both species with the emergence of new metabolites which were dereplicated as a series of siderophores. Large-scale co-culture fermentation led to the isolation of two new pulicatin derivatives together with six known metabolites which were characterised using HRESIMS and NMR analyses. During the in vitro antimicrobial evaluation of the isolated compounds, pulicatin H (2) exhibited the strongest antifungal activity against Pc, followed by aeruginaldehyde (1) and pulicatin F (4), hence explaining the initial growth suppression of Pc in the co-culture environment.

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“…A first indication that IQS could not be the product of AmbABCDE was the discovery that the IQS structure is identical to the structure of aeruginaldehyde, a compound produced by other Pseudomonas, including P. protegens and in Burkholderia thailandensis which do not have the amb genes cluster (Trottmann, Franke, Ishida, García‐Altares, & Hertweck, ; Ye et al, ). Aeruginaldehyde has been detected together with other compounds (aeruginoic acid, aeruginol, dihydroaeruginoic acid), which may be all products derived from the siderophore pyochelin biosynthetic pathway (Ye et al, ). In a very recent study, Trottmann et al confirmed that aeruginaldehyde is derived from pyochelin since an incubation of the siderophore at 30°C resulted in the appearance of aeruginaldehyde (Trottmann et al, ).…”

Section: Commentarymentioning

confidence: 99%

Putting an end to the Pseudomonas aeruginosa IQS controversy

Cornélis

2019

MicrobiologyOpen

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Despite published evidence that IQS (2-(2-hydroxylphenyl)-thiazole-4-carbaldehyde) is in fact aeruginaldehyde, a by-product of the siderophore pyochelin biosynthesis or degradation and that the ambABCDE genes are not responsible for IQS synthesis, several authors, including in top review journals, perpetuate the wrong information. I hope that this short comment will clarify the situation once and for all. K E Y W O R D S aeruginaldehyde, IQS, Pseudomonas aeruginosa, pyochelin, quorum sensing 2 of 2 | CORNELIS al., 2014). In a very recent study, Trottmann et al. confirmed that aeruginaldehyde is derived from pyochelin since an incubation of the siderophore at 30°C resulted in the appearance of aeruginaldehyde (Trottmann et al., 2019). Ye et al. (2014) suggested that aeruginaldehyde could derive from dihydroaeruginoic acid (Dha) released from PchE during the assembly of the NRPS enzymes and the biosynthetic process (Ye et al., 2014). Interestingly, Maspoli, Wenner, Mislin, and Reimmann (2014) found in P. aeruginosa PA14 a genomic island containing genes for the biosynthesis of (enantio)pyochelin. Complementation of a pyochelin negative mutant with one NRPS gene led to the production of Dha (Maspoli et al., 2014). In a recent study, Sun et al. found that only the Rhl and PQS QS systems are involved in the regulation of phenazine production in a P. aeruginosa strain while mutants with deletions in amb or pch genes clusters were not affected in their production of phenazine compounds, excluding their possible participation in the QS circuitry (Sun, Zhou, Jin, Jiang, & He, 2016). | CON CLUS IONDespite the evidence presented here in this short commentary, still scientists publish articles, including reviews, mentioning IQS as the fourth quorum sensing molecule of P. aeruginosa being the product of AmbABCDE. The aim of this short comment is to clarify this point.

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Structure Revision of N-Mercapto-4-formylcarbostyril Produced by Pseudomonas fluorescens G308 to 2-(2-Hydroxyphenyl)thiazole-4-carbaldehyde [aeruginaldehyde]

Cited by 24 publications

References 46 publications

The plant compound rosmarinic acid induces a broad quorum sensing response in Pseudomonas aeruginosa PAO1

The plant compound rosmarinic acid induces a broad quorum sensing response in Pseudomonas aeruginosa PAO1

Induction of Cryptic Antifungal Pulicatin Derivatives from Pantoea Agglomerans by Microbial Co-Culture

Putting an end to the Pseudomonas aeruginosa IQS controversy

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