Plakofuranolactone as a Quorum Quenching Agent from the Indonesian Sponge Plakortis cf. lita

Costantino, Valeria; Sala, Gerardo Della; Saurav, Kumar; Teta, Roberta; Bar-Shalom, Rinat; Mangoni, Alfonso; Steindler, Laura

doi:10.3390/md15030059

Cited by 35 publications

(29 citation statements)

References 43 publications

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“…QSI activity was tested using luminescence-based reporters, E. coli pSB401 and E. coli pSB1075, and was quantified on a TriStar Multimode Microplate reader (Berthold Technologies GmbH & Co. KG, Bad Wildbad, Germany) following the authors of [17,18]. The plasmids pSB401 and pSB1075 contain the luxI/R and lasI/R gene promoters, respectively, regulate luxCDABE expression, and respond well to exogenously provided Acyl Homoserine Lactones (AHLs) [17,19]. Overnight cultures of the reporter strains were diluted to OD 600 of 0.01 and 50 µL was added to each well of 96-well plates.…”

Section: Crude Extracts Preparation and Quorum Sensing Inhibitory (Qsmentioning

confidence: 99%

Isolation, Genomic and Metabolomic Characterization of Streptomyces tendae VITAKN with Quorum Sensing Inhibitory Activity from Southern India

et al. 2020

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Streptomyces are among the most promising genera in terms of production ability to biosynthesize a variety of bioactive secondary metabolites with pharmaceutical interest. Coinciding with the increase in genomic sequencing of these bacteria, mining of their genomes for biosynthetic gene clusters (BGCs) has become a routine component of natural product discovery. Herein, we describe the isolation and characterization of a Streptomyces tendae VITAKN with quorum sensing inhibitory (QSI) activity that was isolated from southern coastal part of India. The nearly complete genome consists of 8,621,231bp with a GC content of 72.2%. Sequence similarity networks of the BGCs detected from this strain against the Minimum Information about a Biosynthetic Gene Cluster (MIBiG) database and 3365 BGCs predicted by antiSMASH analysis of publicly available complete Streptomyces genomes were generated through the BiG-SCAPE-CORASON platform to evaluate its biosynthetic novelty. Crude extract analysis using high-performance liquid chromatography connected to high resolution tandem mass spectrometry (HPLC-HRMS/MS) and dereplication through the Global Natural Product Social Molecular Networking (GNPS) online workflow resulted in the identification of cyclic dipeptides (2, 5-diketopiperazines, DKPs) in the extract, which are known to possess QSI activity. Our results highlight the potential of genome mining coupled with LC-HRMS/MS and in silico tools (GNPS) as a valid approach for the discovery of novel QSI lead compounds. This study also provides the biosynthetic diversity of BGCs and an assessment of the predicted chemical space yet to be discovered.

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Section: Crude Extracts Preparation and Quorum Sensing Inhibitory (Qsmentioning

confidence: 99%

Isolation, Genomic and Metabolomic Characterization of Streptomyces tendae VITAKN with Quorum Sensing Inhibitory Activity from Southern India

et al. 2020

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“…The bioluminescence-based dose-dependent QSI assay was performed using pSB401 and pSB1075 reporters and was quantified on a TriStar Multimode Microplate reader (Berthold Technologies GmbH & Co. KG, Bad Wildbad, Germany) following References [36,60]. The stock solutions (10 mM) of compounds 1, 2 and penicillic acid (PA, positive control) were serially diluted at NIC concentrations (0.252-280 µM) for the assay.…”

Section: Dose-dependent Quantification Of Bioluminescence For Qsi Assaymentioning

confidence: 99%

“…The stock solutions (10 mM) of compounds 1, 2 and penicillic acid (PA, positive control) were serially diluted at NIC concentrations (0.252-280 µM) for the assay. The bioluminescence was recorded every 30 min for 7 h at 30 • C. The production of bioluminescence in the graphs is given as the relative light units (RLU), obtained at 4 h [36].…”

Section: Dose-dependent Quantification Of Bioluminescence For Qsi Assaymentioning

confidence: 99%

“…The inhibition of pyocyanin and protease was tested for compounds 1, 2, and PA (positive control) in a dose-dependent manner at NIC concentrations (0.252-280 µM) using P. aeruginosa PAO1 as described earlier [36]. Methanol (solvent in which test compounds were dissolved) and PA were used for negative and positive control, respectively, for both the experiments.…”

Section: Inhibition Of Production Of Virulence Factors-pyocyanin and mentioning

confidence: 99%

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

et al. 2020

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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.

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“…Few studies have searched for QSI compounds in sponges and their isolates, mainly in a biotechnological context, as such molecules could provide alternatives for antimicrobials, and presence of QSI molecules was reported [29][30][31][32][33]. Whilst AHLs have a common structure, QSI compounds are way more variable: from being structurally similar to AHLs [34,35] to cyclic peptides [36][37][38], alkaloids [31,39], lactones [23,40] and diterpenes [41][42][43]. In our recent work, a novel lactone, named plakofuranolactone, which showed a strong QSI activity at submicromolar concentration, has been discovered from the extract of the Indonesian sponge Plakortis cf.…”

mentioning

confidence: 99%

Co-existence of Quorum Sensing and Quorum Sensing Inhibitory Compounds in Marine Sponge <em>Sarcotragus spinosulus</em>

Saurav¹,

Borbone²,

Burgsdorf³

et al. 2019

Preprint

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Marine sponges, a well documented prolific source of natural products, harbors numerous microbial communities believed to possess N-acyl homoserine lactones (AHLs) mediated Quorum sensing (QS) as one of the mechanisms of interaction. 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 potential for production of both QS signal molecules as well as QS interfering molecules (QSI) in the same sponge species Sarcotragus spinosulus. A total of eighteen saturated acyl chain AHLs were identified along with six putative unsaturated acyl chain AHLs. Bioassay guided purification led to the isolation of two brominated metabolites with QS-interfering activity. The structures of these compounds were elucidated by comparative spectral analysis of 1HNMR and HR-MS data and was identified as 3-Br-N-methyltyramine (1) and 5,6-dibromo-N,N-dimethyltryptamine (2). The QSI activity of compounds 1 and 2 were evaluated using reporter gene assays for long- and short-chain signals (E. coli pSB1075 and E. coli pSB401) and was confirmed by measuring dose dependent inhibition of proteolytic activity and pyocyanin production in P. aeruginosa PAO1. The obtained results showed the co-existence of QS and QSI in S. spinosulus, a complex network which may mediate the orchestrated function of the microbiome within the sponge holobiont.

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Plakofuranolactone as a Quorum Quenching Agent from the Indonesian Sponge Plakortis cf. lita

Cited by 35 publications

References 43 publications

Isolation, Genomic and Metabolomic Characterization of Streptomyces tendae VITAKN with Quorum Sensing Inhibitory Activity from Southern India

Isolation, Genomic and Metabolomic Characterization of Streptomyces tendae VITAKN with Quorum Sensing Inhibitory Activity from Southern India

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

Co-existence of Quorum Sensing and Quorum Sensing Inhibitory Compounds in Marine Sponge <em>Sarcotragus spinosulus</em>

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