Marine organisms as source of extracts to disrupt bacterial communication: bioguided isolation and identification of quorum sensing inhibitors from Ircinia felix

Quintana, Jairo; Brango-Vanegas, José; Costa, Geison Modesti; Castellanos, Leonardo; Arévalo, Catalina; Duque, Carmenza

doi:10.1016/j.bjp.2015.03.013

Cited by 22 publications

(11 citation statements)

References 37 publications

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“…The extract of Ircinia felix was found to be the most potent inhibitor of quorum-sensing with the activity linked to the felixinin furanosesquiterpenoid class. [708][709][710] Chemical examination of adult and bud larvae of the chemically-defended sponge Tethya maza indicated that the sterol composition of both were largely similar, suggesting that the larvae are also defended during reproduction. 711 First total syntheses were reported for many compounds including the lipids motualevic acid F, (E)-and (Z)-antazirine, [712][713][714] mycalol (revised to 1105) [715][716][717] and myrmekioside A, 718,719 and polyacetylenes callyspongynic acid, 720,721 phosphoiodyn A and placotylene A.…”

Section: Spongesmentioning

confidence: 99%

Marine natural products

et al. 2017

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Covering: 2015. Previous review: Nat. Prod. Rep., 2016, 33, 382-431This review covers the literature published in 2015 for marine natural products (MNPs), with 1220 citations (792 for the period January to December 2015) referring to compounds isolated from marine microorganisms and phytoplankton, green, brown and red algae, sponges, cnidarians, bryozoans, molluscs, tunicates, echinoderms, mangroves and other intertidal plants and microorganisms. The emphasis is on new compounds (1340 in 429 papers for 2015), together with the relevant biological activities, source organisms and country of origin. Reviews, biosynthetic studies, first syntheses, and syntheses that lead to the revision of structures or stereochemistries, have been included.

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Section: Spongesmentioning

confidence: 99%

Marine natural products

et al. 2017

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“…Known compounds that have been demonstrated to inhibit the bacterial QS system include p -coumaric acid from garlic extract27, methyl eugenol from Cuminum cyminum 28, baicalein from Scutellaria baicalensis 29, curcumin from Curcuma longa 30, maniwamycins from Streptomyces sp 31,. unidentified secondary metabolites from marine Streptomyces 32, furanosesterterpenes from the marine sponge Ircinia felix 33, sesqui- and triterpenoids from the liverwort Lepidozia chordulifera 34, and unidentified components from edible mushrooms3536.…”

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confidence: 99%

A diketopiperazine factor from Rheinheimera aquimaris QSI02 exhibits anti-quorum sensing activity

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et al. 2016

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An ethyl acetate (EtOAc) extract isolated from the marine bacterium, Rheinheimera aquimaris QSI02, was found to exhibit anti-quorum sensing (anti-QS) activity. A subsequent bioassay-guided isolation protocol led to the detection of an active diketopiperazine factor, cyclo(Trp-Ser). Biosensor assay data showed that the minimum inhibitory concentration (MIC) of cyclo(Trp-Ser) ranged from 3.2 mg/ml to 6.4 mg/m for several microorganisms, including Escherichia coli, Chromobacterium violaceum CV026, Pseudomonas aeruginosa PA01, Staphylococcus aureus, and Candida albicans. Additionally, sub-MICs of cyclo(Trp-Ser) decreased the QS-regulated violacein production in C. violaceum CV026 by 67%. Furthermore, cyclo(Trp-Ser) can decrease QS-regulated pyocyanin production, elastase activity and biofilm formation in P. aeruginosa PA01 by 65%, 40% and 59.9%, respectively. Molecular docking results revealed that cyclo(Trp-Ser) binds to CviR receptor more rigidly than C6HSL with lower docking energy −8.68 kcal/mol, while with higher binding energy of −8.40 kcal/mol than 3-oxo-C12HSL in LasR receptor. Molecular dynamics simulation suggested that cyclo(Trp-Ser) is more easy to bind to CviR receptor than natural signaling molecule, but opposite in LasR receptor. These results suggest that cyclo(Trp-Ser) can be used as a potential inhibitor to control QS systems of C. violaceum and P. aeruginosa and provide increased the understanding of molecular mechanism that influences QS-regulated behaviors.

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“…Compound (7 Z ,13 Z ,18 R ,20 Z )-felixinin acetate ( 37 ), (8 Z ,13 Z ,18 R ,20 Z )-strobilinin acetate ( 38 ), (7 E ,13 Z ,18 R ,20 Z )-felixinin acetate ( 39 ) and (8 E ,13 Z ,18 R ,20 Z )-strobilinin acetate ( 40 ) was isolated with distinct configuration along with compound (7 E ,12 E ,18 R ,20 Z )-variabilin acetate ( 41 ) using C. violaceum biosensor [43]. These compounds were previously reported from I. felix based on their antimicrobial properties [94,95].…”

Section: Qsi From Marine Spongesmentioning

confidence: 99%

Quorum Sensing Inhibitors from the Sea Discovered Using Bacterial N-acyl-homoserine Lactone-Based Biosensors

et al. 2017

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Marine natural products with antibiotic activity have been a rich source of drug discovery; however, the emergence of antibiotic-resistant bacterial strains has turned attention towards the discovery of alternative innovative strategies to combat pathogens. In many pathogenic bacteria, the expression of virulence factors is under the regulation of quorum sensing (QS). QS inhibitors (QSIs) present a promising alternative or potential synergistic treatment since they disrupt the signaling pathway used for intra- and interspecies coordination of expression of virulence factors. This review covers the set of molecules showing QSI activity that were isolated from marine organisms, including plants (algae), animals (sponges, cnidarians, and bryozoans), and microorganisms (bacteria, fungi, and cyanobacteria). The compounds found and the methods used for their isolation are the emphasis of this review.

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Marine organisms as source of extracts to disrupt bacterial communication: bioguided isolation and identification of quorum sensing inhibitors from Ircinia felix

Cited by 22 publications

References 37 publications

Marine natural products

Marine natural products

A diketopiperazine factor from Rheinheimera aquimaris QSI02 exhibits anti-quorum sensing activity

Quorum Sensing Inhibitors from the Sea Discovered Using Bacterial N-acyl-homoserine Lactone-Based Biosensors

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