scholarly journals An Unprecedented Medium-Chain Diunsaturated N-acylhomoserine Lactone from Marine Roseobacter Group Bacteria

Marine Drugs ◽  
2018 ◽  
Vol 17 (1) ◽  
pp. 20 ◽  
Author(s):  
Lisa Ziesche ◽  
Laura Wolter ◽  
Hui Wang ◽  
Thorsten Brinkhoff ◽  
Marion Pohlner ◽  
...  
Keyword(s):  
Quorum Sensing ◽  
Acyl Chain ◽  
Homoserine Lactone ◽  
Compound Identification ◽  
Structural Element ◽  
Mass Spectral ◽  
Acylhomoserine Lactone ◽  
The North ◽  
Bacterial Signaling ◽  
Roseobacter Group

N-acylhomoserine lactones (AHLs), bacterial signaling compounds involved in quorum-sensing, are a structurally diverse group of compounds. We describe here the identification, synthesis, occurrence and biological activity of a new AHL, N-((2E,5Z)-2,5-dodecadienoyl)homoserine lactone (11) and its isomer N-((3E,5Z)-3,5-dodecadienoyl)homoserine lactone (13), occurring in several Roseobacter group bacteria (Rhodobacteraceae). The analysis of 26 strains revealed the presence of 11 and 13 in six of them originating from the surface of the macroalgae Fucus spiralis or sediments from the North Sea. In addition, 18 other AHLs were detected in 12 strains. Compound identification was performed by GC/MS. Mass spectral analysis revealed a diunsaturated C12 homoserine lactone as structural element of the new AHL. Synthesis of three likely candidate compounds, 11, 13 and N-((2E,4E)-2,4-dodecadienoyl)homoserine lactone (5), revealed the former to be the natural AHLs. Bioactivity test with quorum-sensing reporter strains showed high activity of all three compounds. Therefore, the configuration and stereochemistry of the double bonds in the acyl chain seemed to be unimportant for the activity, although the chains have largely different shapes, solely the chain length determining activity. In combination with previous results with other Roseobacter group bacteria, we could show that there is wide variance between AHL composition within the strains. Furthermore, no association of certain AHLs with different habitats like macroalgal surfaces or sediment could be detected.

scholarly journals Inhibition of Quorum Sensing in Serratia marcescens AS-1 by Synthetic Analogs of N-Acylhomoserine Lactone

2007 ◽  
Vol 73 (20) ◽  
pp. 6339-6344 ◽  
Author(s):  
Tomohiro Morohoshi ◽  
Toshitaka Shiono ◽  
Kiyomi Takidouchi ◽  
Masashi Kato ◽  
Norihiro Kato ◽  
...  
Keyword(s):  
Quorum Sensing ◽  
Serratia Marcescens ◽  
Biofilm Formation ◽  
Acyl Chain ◽  
Regulatory System ◽  
Homoserine Lactone ◽  
Signal Molecule ◽  
Swarming Motility ◽  
Gram Negative ◽  
Acylhomoserine Lactone

ABSTRACT Quorum sensing is a regulatory system for controlling gene expression in response to increasing cell density. N-Acylhomoserine lactone (AHL) is produced by gram-negative bacteria, which use it as a quorum-sensing signal molecule. Serratia marcescens is a gram-negative opportunistic pathogen which is responsible for an increasing number of serious nosocomial infections. S. marcescens AS-1 produces N-hexanoyl homoserine lactone (C6-HSL) and N-(3-oxohexanoyl) homoserine lactone and regulates prodigiosin production, swarming motility, and biofilm formation by AHL-mediated quorum sensing. We synthesized a series of N-acyl cyclopentylamides with acyl chain lengths ranging from 4 to 12 and estimated their inhibitory effects on prodigiosin production in AS-1. One of these molecules, N-nonanoyl-cyclopentylamide (C9-CPA), had a strong inhibitory effect on prodigiosin production. C9-CPA also inhibited the swarming motility and biofilm formation of AS-1. A competition assay revealed that C9-CPA was able to inhibit quorum sensing at four times the concentration of exogenous C6-HSL and was more effective than the previously reported halogenated furanone. Our results demonstrated that C9-CPA was an effective quorum-sensing inhibitor for S. marcescens AS-1.

scholarly journals N-Acylhomoserine lactone quorum-sensing molecules are modified and degraded by Rhodococcus erythropolis W2 by both amidolytic and novel oxidoreductase activities

Microbiology ◽  
2005 ◽  
Vol 151 (10) ◽  
pp. 3313-3322 ◽  
Author(s):  
Stéphane Uroz ◽  
Siri Ram Chhabra ◽  
Miguel Cámara ◽  
Paul Williams ◽  
Phil Oger ◽  
...  
Keyword(s):  
Quorum Sensing ◽  
Acyl Chain ◽  
Rhodococcus Erythropolis ◽  
Homoserine Lactone ◽  
Signal Molecules ◽  
Signal Molecule ◽  
Oxidoreductase Activity ◽  
Whole Cells ◽  
Acylhomoserine Lactone ◽  
Cell Extracts

The Rhodococcus erythropolis strain W2 has been shown previously to degrade the N-acylhomoserine lactone (AHL) quorum-sensing signal molecule N-hexanoyl-l-homoserine lactone, produced by other bacteria. Data presented here indicate that this Gram-positive bacterium is also capable of using various AHLs as the sole carbon and energy source. The enzymic activities responsible for AHL inactivation were investigated in R. erythropolis cell extracts and in whole cells. R. erythropolis cells rapidly degraded AHLs with 3-oxo substituents but exhibited relatively poor activity against the corresponding unsubstituted AHLs. Investigation of the mechanism(s) by which R. erythropolis cells degraded AHLs revealed that 3-oxo compounds with N-acyl side chains ranging from C8 to C14 were initially converted to their corresponding 3-hydroxy derivatives. This oxidoreductase activity was not specific to 3-oxo-AHLs but also allowed the reduction of compounds such as N-(3-oxo-6-phenylhexanoyl)homoserine lactone (which contains an aromatic acyl chain substituent) and 3-oxododecanamide (which lacks the homoserine lactone ring). It also reduced both the d- and l-isomers of n-(3-oxododecanoyl)-l-homoserine lactone. A second AHL-degrading activity was observed when R. erythropolis cell extracts were incubated with N-(3-oxodecanoyl)-l-homoserine lactone (3O,C10-HSL). This activity was both temperature- and pH-dependent and was characterized as an amidolytic activity by HPLC analysis of the reaction mixture treated with dansyl chloride. This revealed the accumulation of dansylated homoserine lactone, indicating that the 3O,C10-HSL amide had been cleaved to yield homoserine lactone. R. erythropolis is therefore capable of modifying and degrading AHL signal molecules through both oxidoreductase and amidolytic activities.

scholarly journals LuxR- and LuxI-Type Quorum-Sensing Circuits Are Prevalent in Members of the Populus deltoides Microbiome

2013 ◽  
Vol 79 (18) ◽  
pp. 5745-5752 ◽  
Author(s):  
Amy L. Schaefer ◽  
Colin R. Lappala ◽  
Ryan P. Morlen ◽  
Dale A. Pelletier ◽  
Tse-Yuan S. Lu ◽  
...  
Keyword(s):  
Quorum Sensing ◽  
Populus Deltoides ◽  
Cell Communication ◽  
Homoserine Lactone ◽  
Bacterial Isolates ◽  
Content Type ◽  
Eastern Cottonwood ◽  
Bacterial Signaling ◽  
Signal Production ◽  
Plant Signals

ABSTRACTWe are interested in the root microbiome of the fast-growing Eastern cottonwood tree,Populus deltoides. There is a large bank of bacterial isolates fromP. deltoides, and there are 44 draft genomes of bacterial endophyte and rhizosphere isolates. As a first step in efforts to understand the roles of bacterial communication and plant-bacterial signaling inP. deltoides, we focused on the prevalence of acyl-homoserine lactone (AHL) quorum-sensing-signal production and reception in members of theP. deltoidesmicrobiome. We screened 129 bacterial isolates for AHL production using a broad-spectrum bioassay that responds to many but not all AHLs, and we queried the available genome sequences of microbiome isolates for homologs of AHL synthase and receptor genes. AHL signal production was detected in 40% of 129 strains tested. Positive isolates included members of theAlpha-,Beta-, andGammaproteobacteria. Members of theluxIfamily of AHL synthases were identified in 18 of 39 proteobacterial genomes, including genomes of some isolates that tested negative in the bioassay. Members of theluxRfamily of transcription factors, which includes AHL-responsive factors, were more abundant thanluxIhomologs. There were 72 in the 39 proteobacterial genomes. Some of theluxRhomologs appear to be members of a subfamily of LuxRs that respond to as-yet-unknown plant signals rather than bacterial AHLs. Apparently, there is a substantial capacity for AHL cell-to-cell communication in proteobacteria of theP. deltoidesmicrobiota, and there are alsoProteobacteriawith LuxR homologs of the type hypothesized to respond to plant signals or cues.

scholarly journals The LuxM Homologue VanM from Vibrio anguillarumDirects the Synthesis of N-(3-Hydroxyhexanoyl)homoserine Lactone and N-Hexanoylhomoserine Lactone

2001 ◽  
Vol 183 (12) ◽  
pp. 3537-3547 ◽  
Author(s):  
Debra L. Milton ◽  
Victoria J. Chalker ◽  
David Kirke ◽  
Andrea Hardman ◽  
Miguel Cámara ◽  
...  
Keyword(s):  
Quorum Sensing ◽  
Vibrio Anguillarum ◽  
Homoserine Lactone ◽  
Regulatory Elements ◽  
Sequencing Error ◽  
Infection Model ◽  
Reading Frame ◽  
Acylhomoserine Lactone ◽  
Sensing System ◽  
Quorum Sensing System

ABSTRACT Vibrio anguillarum, which causes terminal hemorrhagic septicemia in fish, was previously shown to possess a LuxRI-type quorum-sensing system (vanRI) and to produceN-(3-oxodecanoyl)homoserine lactone (3-oxo-C10-HSL). However, a vanI null mutant still activatedN-acylhomoserine lactone (AHL) biosensors, indicating the presence of an additional quorum-sensing circuit in V. anguillarum. In this study, we have characterized this second system. Using high-pressure liquid chromatography in conjunction with mass spectrometry and chemical analysis, we identified two additional AHLs as N-hexanoylhomoserine lactone (C6-HSL) andN-(3-hydroxyhexanoyl)homoserine lactone (3-hydroxy-C6-HSL). Quantification of each AHL present in stationary-phase V. anguillarum spent culture supernatants indicated that 3-oxo-C10-HSL, 3-hydroxy-C6-HSL, and C6-HSL are present at approximately 8.5, 9.5, and 0.3 nM, respectively. Furthermore,vanM, the gene responsible for the synthesis of these AHLs, was characterized and shown to be homologous to the luxLand luxM genes, which are required for the production ofN-(3-hydroxybutanoyl)homoserine lactone in Vibrio harveyi. However, resequencing of the V. harveyi luxL/luxM junction revealed a sequencing error present in the published sequence, which when corrected resulted in a single open reading frame (termed luxM). Downstream ofvanM, we identified a homologue of luxN(vanN) that encodes a hybrid sensor kinase which forms part of a phosphorelay cascade involved in the regulation of bioluminescence in V. harveyi. A mutation in vanM abolished the production of C6-HSL and 3-hydroxy-C6-HSL. In addition, production of 3-oxo-C10-HSL was abolished in the vanM mutant, suggesting that 3-hydroxy-C6-HSL and C6-HSL regulate the production of 3-oxo-C10-HSL via vanRI. However, a vanN mutant displayed a wild-type AHL profile. Neither mutation affected either the production of proteases or virulence in a fish infection model. These data indicate that V. anguillarum possesses a hierarchical quorum sensing system consisting of regulatory elements homologous to those found in both V. fischeri (the LuxRI homologues VanRI) and V. harveyi (the LuxMN homologues, VanMN).

scholarly journals The Plant Pathogen Pantoea ananatis Produces N-Acylhomoserine Lactone and Causes Center Rot Disease of Onion by Quorum Sensing

2007 ◽  
Vol 189 (22) ◽  
pp. 8333-8338 ◽  
Author(s):  
Tomohiro Morohoshi ◽  
Yuta Nakamura ◽  
Go Yamazaki ◽  
Akio Ishida ◽  
Norihiro Kato ◽  
...  
Keyword(s):  
Quorum Sensing ◽  
Biofilm Formation ◽  
Receptor Gene ◽  
Homoserine Lactone ◽  
Pantoea Ananatis ◽  
Signal Molecule ◽  
Acylhomoserine Lactone ◽  
Sensing System ◽  
Quorum Sensing System ◽  
Rot Disease

ABSTRACT A number of gram-negative bacteria have a quorum-sensing system and produce N-acyl-l-homoserine lactone (AHL) that they use them as a quorum-sensing signal molecule. Pantoea ananatis is reported as a common colonist of wheat heads at ripening and causes center rot of onion. In this study, we demonstrated that P. ananatis SK-1 produced two AHLs, N-hexanoyl-l-homoserine lactone (C6-HSL) and N-(3-oxohexanoyl)-l-homoserine lactone (3-oxo-C6-HSL). We cloned the AHL-synthase gene (eanI) and AHL-receptor gene (eanR) and revealed that the deduced amino acid sequence of EanI/EanR showed high identity to those of EsaI/EsaR from P. stewartii. EanR repressed the ean box sequence and the addition of AHLs resulted in derepression of ean box. Inactivation of the chromosomal eanI gene in SK-1 caused disruption of exopolysaccharide (EPS) biosynthesis, biofilm formation, and infection of onion leaves, which were recovered by adding exogenous 3-oxo-C6-HSL. These results demonstrated that the quorum-sensing system involved the biosynthesis of EPS, biofilm formation, and infection of onion leaves in P. ananatis SK-1.

scholarly journals Biofilm Formation and Quorum-Sensing-Molecule Production by Clinical Isolates of Serratia liquefaciens

2015 ◽  
Vol 81 (10) ◽  
pp. 3306-3315 ◽  
Author(s):  
Sara Remuzgo-Martínez ◽  
María Lázaro-Díez ◽  
Celia Mayer ◽  
Maitane Aranzamendi-Zaldumbide ◽  
Daniel Padilla ◽  
...  
Keyword(s):  
Liquid Chromatography ◽  
Quorum Sensing ◽  
Nosocomial Infections ◽  
Biofilm Formation ◽  
Acyl Chain ◽  
Homoserine Lactone ◽  
Hospital Environment ◽  
Term Survival ◽  
Content Type ◽  
Serratia Liquefaciens

ABSTRACTSerratiaspp. are opportunistic human pathogens responsible for an increasing number of nosocomial infections. However, little is known about the virulence factors and regulatory circuits that may enhance the establishment and long-term survival ofSerratia liquefaciensin the hospital environment. In this study, two reporter strains,Chromobacterium violaceumCV026 and VIR24, and high-resolution triple-quadrupole liquid chromatography–mass spectrometry (LC-MS) were used to detect and to quantifyN-acyl-homoserine lactone (AHL) quorum-sensing signals in 20S. liquefaciensstrains isolated from clinical samples. Only four of the strains produced sufficient amounts of AHLs to activate the sensors. Investigation of two of the positive strains by high-performance liquid chromatography (HPLC)-MS confirmed the presence of significant amounts of short-acyl-chain AHLs (N-butyryl-l-homoserine lactone [C4-HSL] andN-hexanoyl-l-homoserine lactone [C6-HSL]) in both strains, which exhibited a complex and strain-specific signal profile that included minor amounts of other short-acyl-chain AHLs (N-octanoyl-l-homoserine lactone [C8-HSL] andN-3-oxohexanoyl-l-homoserine lactone [OC6-HSL]) and long-acyl-chain (C10, C12, and C14) AHLs. No correlation between biofilm formation and the production of large amounts of AHLs could be established. Fimbria-like structures were observed by transmission electron microscopy, and the presence of the type 1 fimbrial adhesin genefimHin all strains was confirmed by PCR. The ability ofS. liquefaciensto adhere to abiotic surfaces and to form biofilms likely contributes to its persistence in the hospital environment, increasing the probability of causing nosocomial infections. Therefore, a better understanding of the adherence properties of this species will provide greater insights into the diseases it causes.

scholarly journals Identification of Quorum Sensing Activators and Inhibitors in The Marine Sponge Sarcotragus spinosulus

Marine Drugs ◽  
2020 ◽  
Vol 18 (2) ◽  
pp. 127 ◽  
Author(s):  
Kumar Saurav ◽  
Nicola Borbone ◽  
Ilia Burgsdorf ◽  
Roberta Teta ◽  
Alessia Caso ◽  
...  
Keyword(s):  
Quorum Sensing ◽  
Acyl Chain ◽  
Genetic Regulation ◽  
Homoserine Lactone ◽  
Marine Sponges ◽  
Complex Signal ◽  
Signal Molecules ◽  
Bacterial Gene ◽  
Eukaryotic Organisms ◽  
And Function

Marine sponges, a well-documented prolific source of natural products, harbor highly diverse microbial communities. Their extracts were previously shown to contain quorum sensing (QS) signal molecules of the N-acyl homoserine lactone (AHL) type, known to orchestrate bacterial gene regulation. Some bacteria and eukaryotic organisms are known to produce molecules that can interfere with QS signaling, thus affecting microbial genetic regulation and function. In the present study, we established the production of both QS signal molecules as well as QS inhibitory (QSI) molecules in the sponge species Sarcotragus spinosulus. A total of eighteen saturated acyl chain AHLs were identified along with six unsaturated acyl chain AHLs. Bioassay-guided purification led to the isolation of two brominated metabolites with QSI activity. The structures of these compounds were elucidated by comparative spectral analysis of 1HNMR and HR-MS data and were identified as 3-bromo-4-methoxyphenethylamine (1) and 5,6-dibromo-N,N-dimethyltryptamine (2). The QSI activity of compounds 1 and 2 was evaluated using reporter gene assays for long- and short-chain AHL signals (Escherichia coli pSB1075 and E. coli pSB401, respectively). QSI activity was further confirmed by measuring dose-dependent inhibition of proteolytic activity and pyocyanin production in Pseudomonas aeruginosa PAO1. The obtained results show the coexistence of QS and QSI in S. spinosulus, a complex signal network that may mediate the orchestrated function of the microbiome within the sponge holobiont.

scholarly journals Disruption of epithelial barrier by quorum-sensing N-3-(oxododecanoyl)-homoserine lactone is mediated by matrix metalloproteinases

2014 ◽  
Vol 306 (11) ◽  
pp. G992-G1001 ◽  
Author(s):  
Sung Yong Eum ◽  
Dima Jaraki ◽  
Luc Bertrand ◽  
Ibolya E. András ◽  
Michal Toborek
Keyword(s):  
Quorum Sensing ◽  
Lipid Raft ◽  
Intestinal Epithelium ◽  
Barrier Function ◽  
Homoserine Lactone ◽  
Gram Negative Bacteria ◽  
Intestinal Epithelial ◽  
Cell Monolayers ◽  
Acylhomoserine Lactone ◽  
The Impact

The intestinal epithelium forms a selective barrier maintained by tight junctions (TJs) and separating the luminal environment from the submucosal tissues. N-acylhomoserine lactone (AHL) quorum-sensing molecules produced by gram-negative bacteria in the gut can influence homeostasis of the host intestinal epithelium. In the present study, we evaluated the regulatory mechanisms affecting the impact of two representative long- and short-chain AHLs, N-3-(oxododecanoyl)-homoserine lactone (C12-HSL) and N-butyryl homoserine lactone (C4-HSL), on barrier function of human intestinal epithelial Caco-2 cells. Treatment with C12-HSL, but not with C4-HSL, perturbed Caco-2 barrier function; the effect was associated with decreased levels of the TJ proteins occludin and tricellulin and their delocalization from the TJs. C12-HSL also induced matrix metalloprotease (MMP)-2 and MMP-3 activation via lipid raft- and protease-activated receptor (PAR)-dependent signaling. Pretreatment with lipid raft disruptors, PAR antagonists, or MMP inhibitors restored the C12-HSL-induced loss of the TJ proteins and increased permeability of Caco-2 cell monolayers. These results indicate that PAR/lipid raft-dependent MMP-2 and -3 activation followed by degradation of occludin and tricellulin are involved in C12-HSL-induced alterations of epithelial paracellular barrier functions.

scholarly journals The Pseudomonas aeruginosa Quorum-Sensing Molecule N-3-(Oxododecanoyl)-l-Homoserine Lactone Inhibits T-Cell Differentiation and Cytokine Production by a Mechanism Involving an Early Step in T-Cell Activation

2005 ◽  
Vol 73 (3) ◽  
pp. 1648-1655 ◽  
Author(s):  
A. J. Ritchie ◽  
A. Jansson ◽  
J. Stallberg ◽  
P. Nilsson ◽  
P. Lysaght ◽  
...  
Keyword(s):  
Pseudomonas Aeruginosa ◽  
T Cells ◽  
T Cell ◽  
Quorum Sensing ◽  
Cd4 T Cells ◽  
Cytokine Production ◽  
Acyl Chain ◽  
Homoserine Lactone ◽  
Th2 Cells ◽  
Quorum Sensing Molecule

ABSTRACT The Pseudomonas aeruginosa quorum-sensing molecule N-3-(oxododecanoyl)-l-homoserine lactone (OdDHL) has been reported to have immunomodulatory activity in several systems, although the mechanism of that activity remains to be fully characterized. We demonstrate here, using a defined in vitro model of antigen responses by T-cell receptor (TCR)-transgenic mouse splenic CD4 T cells, that the effect of OdDHL on activation and cytokine production is complete within 4 h of antigen or mitogen stimulation and does not depend on the insertion of OdDHL in the cell membrane, despite a previous report that immunosuppression by homoserine lactones required a minimum acyl chain length of 11 carbons (S. R. Chhabra, C. Harty, D. S. W. Hooi, M. Daykin, B. W. Bycroft, P. Williams, and D. Pritchard, J. Med. Chem. 46:97-104, 2003). We also demonstrate that while OdDHL can have toxic effects on nonlymphoid leukocytes, it does not induce significant cell death in T cells at the concentrations (≤10 μM) used in these experiments. In addition, we show that primary and secondary antigen-specific cytokine responses are equally susceptible to inhibition by OdDHL and that the compound inhibits the differentiation of both Th1 and Th2 cells. However, the precise balance of cytokine production by CD4 T cells stimulated in the presence of OdDHL varies with both the antigen concentration and its affinity for the transgenic TCR. Thus, conflicting reports of the nature of the immunosuppression by OdDHL may be due in part to the differences in antigen affinity and concentration in different models.

scholarly journals Characterization of a Phosphotriesterase-Like Lactonase fromSulfolobus solfataricusand Its Immobilization for Disruption of Quorum Sensing

2010 ◽  
Vol 77 (4) ◽  
pp. 1181-1186 ◽  
Author(s):  
Filomena S. W. Ng ◽  
Daniel M. Wright ◽  
Stephen Y. K. Seah
Keyword(s):  
Quorum Sensing ◽  
Virulence Factors ◽  
Acyl Chain ◽  
Quorum Quenching ◽  
Homoserine Lactone ◽  
Homoserine Lactones ◽  
Specificity Constant ◽  
Chain Lengths ◽  
Quorum Sensing Signals

ABSTRACTSsoPox, a bifunctional enzyme with organophosphate hydrolase andN-acyl homoserine lactonase activities from the hyperthermophilic archaeonSulfolobus solfataricus, was overexpressed and purified from recombinantPseudomonas putidaKT2440 with a yield of 9.4 mg of protein per liter of culture. The enzyme has a preference forN-acyl homoserine lactones (AHLs) with acyl chain lengths of at least 8 carbon atoms, mainly due to lowerKmvalues for these substrates. The highest specificity constant obtained was forN-3-oxo-decanoyl homoserine lactone (kcat/Km= 5.5 × 103M−1·s−1), but SsoPox can also degradeN-butyryl homoserine lactone (C4-HSL) andN-oxo-dodecanoyl homoserine lactone (oxo-C12-HSL), which are important for quorum sensing in ourPseudomonas aeruginosamodel system. WhenP. aeruginosaPAO1 cultures were grown in the presence of SsoPox-immobilized membranes, the production of C4-HSL- and oxo-C12-HSL-regulated virulence factors, elastase, protease, and pyocyanin were significantly reduced. This is the first demonstration that immobilized quorum-quenching enzymes can be used to attenuate the production of virulence factors controlled by quorum-sensing signals.

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