Flavonoids from Piper delineatum modulate quorum-sensing-regulated phenotypes in Vibrio harveyi

Phytochemistry

Volumn 117, Issue , 2015, Pages 98-106

  Martín Rodríguez, Alberto J ^a,b   Ticona, Juan C ^c   Jiménez, Ignacio A ^a   Flores, Ninoska ^c   Fernández, José J ^a   Bazzocchi, Isabel L ^a  

^a UNIVERSIDAD DE LA LAGUNA   (Spain)

^b OCEANIC PLATFORM OF THE CANARY ISLANDS   (Spain)

^c UNIVERSIDAD MAYOR DE SAN ANDRÉS   (Bolivia)

Author keywords

Biofilm; Flavonoids; Piper delineatum; Quorum sensing; Vibrio harveyi

Indexed keywords

BACTERIA (MICROORGANISMS); VIBRIO HARVEYI;

FLAVONOID;

BIOFILM; CHEMICAL STRUCTURE; CHEMISTRY; DRUG EFFECTS; ISOLATION AND PURIFICATION; METABOLISM; MICROBIOLOGY; NUCLEAR MAGNETIC RESONANCE; PERU; PHENOTYPE; PHYSIOLOGY; PIPER (PLANT); PLANT LEAF; QUORUM SENSING; VIBRIO;

BIOFILMS; FLAVONOIDS; MOLECULAR STRUCTURE; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; PERU; PHENOTYPE; PIPER; PLANT LEAVES; QUORUM SENSING; VIBRIO;

EID: 84930942185     PISSN: 00319422     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.phytochem.2015.06.006     Document Type: Article

References (37)

1. O.M. Andersen, and K.R. Markham Flavonoids, Chemistry, Biochemistry and Applications 2006 Taylor and Francis Boca Ratón, Florida
2. C. Anetzberger, U. Schell, and K. Jung Single cell analysis of Vibrio harveyi uncovers functional heterogeneity in response to quorum sensing signals BMC Microbiol. 12 2012 209
3. J.C. Aponte, D. Castillo, Y. Estevez, G. Gonzalez, J. Arevalo, Gerald B. Hammond, and M. Sauvain In vitro and in vivo anti-leishmania activity of polysubstituted synthetic chalcones Bioorg. Med. Chem. Lett. 20 2010 100 103
4. T. Bjarnsholt, O. Ciofu, S. Molin, M. Givskov, and N. Hoiby Applying insights from biofilm biology to drug development - can a new approach be developed? Nat. Rev. Drug Discov. 12 2013 791 808
5. A. Boumendjel, J. Boccard, P.-A. Carrupt, E. Nicolle, M. Blanc, A. Geze, L. Choisnard, D. Wouessidjewe, E.-L. Matera, and C. Dumontet Antimitotic and antiproliferative activities of chalcones: forward structure-activity relationship J. Med. Chem. 51 2008 2307 2310
6. K. Chantrapromma, Y. Rat-A-pa, C. Karalai, V. Lojanapiwatana, and V. Seechammanturakit A chalcone and a dihydrochalcone from Uvaria dulcis Phytochemistry 53 2000 511 513
7. T.P.T. Cushnie, and A.J. Lamb Recent advances in understanding the antibacterial properties of flavonoids Int. J. Antimicrob. Agents 38 2011 99 107
8. T. Defoirdt, T. Benneche, G. Brackman, T. Coenye, P. Sorgeloos, and A.A. Scheie A quorum sensing-disrupting brominated thiophenone with a promising therapeutic potential to treat luminescent Vibriosis PLoS One 7 2012 e41788
9. T. Defoirdt, N. Boon, P. Sorgeloos, W. Verstraete, and P. Bossier Quorum sensing and quorum quenching in Vibrio harveyi: lessons learned from in vivo work ISME J. 2 2008 19 26
10. T. Defoirdt, N. Boon, and P. Bossier Can bacteria evolve resistance to quorum sensing disruption? PLoS Pathog. 6 2010 e1000989
11. T. Defoirdt, G. Brackman, and T. Coenye Quorum sensing inhibitors: how strong is the evidence? Trends Microbiol. 21 2013 619 624
12. T. Defoirdt, C.M. Miyamoto, T.K. Wood, E.A. Meighen, P. Sorgeloos, W. Verstraete, and P. Bossier The natural furanone (5Z)-4-bromo-5-(bromomethylene)-3-butyl-2(5H)-furanone disrupts quorum sensing-regulated gene expression in Vibrio harveyi by decreasing the DNA-binding activity of the transcriptional regulator protein luxR Environ. Microbiol. 9 2007 2486 2495
13. S. Dobretsov, H.-U. Dahms, H. YiLi, M. Wahl, and P.-Y. Qian The effect of quorum-sensing blockers on the formation of marine microbial communities and larval attachment FEMS Microbiol. Ecol. 60 2007 177 188
14. X. Fu, T. Sevenet, F. Remy, M. Pais, A. Hadi, A. Hamid, and L.M. Zeng Flavanone and chalcone derivatives from Cryptocarya kurzii J. Nat. Prod. 56 1993 1153 1163
15. R. García-Contreras, T. Maeda, and T.K. Wood Resistance to quorum-quenching compounds Appl. Environ. Microbiol. 79 2013 6840 6846
16. M. Givskov, R. de Nys, M. Manefield, L. Gram, R. Maximilien, L. Eberl, S. Molin, P.D. Steinberg, and S. Kjelleberg Eukaryotic interference with homoserine lactone-mediated prokaryotic signaling J. Bacteriol. 178 1996 6618 6622
17. J.B. Harborne, and T.J. Mabry The Flavonoids 1975 Chapman and Hall London
18. J.M. Henke, and B.L. Bassler Three parallel quorum-sensing systems regulate gene expression in Vibrio harveyi J. Bacteriol. 186 2004 6902 6914
19. I. Joint, K. Tait, and G. Wheeler Cross-kingdom signalling: exploitation of bacterial quorum sensing molecules by the green seaweed Ulva. Philos Trans. R. Soc. Lond. B Biol. Sci. 362 2007 1223 1233
20. V.C. Kalia Quorum sensing vs quorum quenching: a battle with no end insight Biotechnol. Adv. 31 2013 224 245
21. M. Kuroyanagi, T. Noro, S. Fukushima, R. Aiyama, A. Ikuta, H. Itokawa, and M. Morita Studies on the constituents of the seeds of Alpinia katsumadai Hayata Chem. Pharm. Bull. 31 1983 1544 1550
22. A.J. Martín-Rodríguez, J.M. Babarro, F. Lahoz, M. Sansón, V.S. Martín, M. Norte, and J.J. Fernández From broad-spectrum biocides to quorum sensing disruptors and mussel repellents: antifouling profile of alkyl triphenylphosphonium salts PLoS One 10 2015 e0123652
23. B. Mielich-Suss, and D. López Molecular mechanisms involved in Bacillus subtilis biofilm formation Environ. Microbiol. 17 2015 555 565
24. M.B. Miller, and B.L. Bassler Quorum sensing in bacteria Annu. Rev. Micriobiol. 55 2001 165 169
25. Z.E. Nackerdien, A. Keynan, B.L. Bassler, J. Lederberg, and D.S. Thaler Quorum sensing influences Vibrio harveyi growth rates in a manner not fully accounted for by the marker effect of bioluminescence PLoS One 3 2008 e1671
26. F. Nazzaro, F. Fratianni, and R. Coppola Quorum sensing and phytochemicals Int. J. Mol. Sci. 14 2013 12607 12619
27. A.J. Pompeani, J.J. Irgon, M.F. Berger, M.L. Bulyk, N.S. Wingreen, and B.L. Bassler The Vibrio harveyi master quorum-sensing regulator, LuxR, a TetR-type protein is both an activator and a repressor: DNA recognition and binding specificity at target promoters Mol. Microbiol. 70 2008 76 88
28. S.T. Rutherford, and B.L. Bassler Bacterial quorum sensing: its role in virulence and possibilities for its control Cold Spring Harb. Perspect. Med. 2 2012 a012427
29. L. Tan, X.-F. Zhang, B.-Z. Yan, H.-M. Shi, L.-B. Du, Y.-Z. Zhang, L.-F. Wang, Y.-L. Tang, and Y. Liu A novel flavonoid from Lespedeza virgata (Thunb.) DC.: structural elucidation and antioxidative activity Bioorg. Med. Chem. Lett. 17 2007 6311 6315
30. M.S. Twigg, K. Tait, P. Williams, S. Atkinson, and M. Cámara Interference with the germination and growth of Ulva zoospores by quorum sensing molecules produced by Ulva-associated epiphytic bacteria Environ. Microbiol. 16 2014 445 453
31. O.M. Vandeputte, M. Kiendrebeogo, S. Rajaonson, B. Diallo, A. Mol, M. El Jaziri, and M. Baucher Identification of catechin as one of the flavonoids from Combretum albiflorum bark extract that reduces the production of quorum-sensing-controlled virulence factors in Pseudomonas aeruginosa PAO1 Appl. Environ. Microbiol. 76 2010 243 253
32. O.M. Vandeputte, M. Kiendrebeogo, T. Rasamiravaka, C. Stévigny, P. Duez, S. Rajaonson, B. Diallo, A. Mol, M. Baucher, and M. El Jaziri The flavanone naringenin reduces the production of quorum sensing-controlled virulence factors in Pseudomonas aeruginosa PAO1 Microbiology 157 2011 2120 2132
33. A. Vikram, G.K. Jayaprakasha, P.R. Jesudhasan, S.D. Pillai, and B.S. Patil Suppression of bacterial cell-cell signaling, biofilm formation and type III secretion system by citrus flavonoids J. Appl. Microbiol. 109 2010 515 527
34. S. Vogel, M. Barbic, G. Jürgenliemk, and J. Heilmann Synthesis, cytotoxicity, anti-oxidative and anti-inflammatory activity of chalcones and influence of A-ring modifications on the pharmacological effect Eur. J. Med. Chem. 45 2010 2206 2213
35. C.M. Waters, and B.L. Bassler Quorum sensing: cell-to-cell communication in bacteria Annu. Rev. Cell Dev. Biol. 21 2005 319 346
36. C.M. Waters, and B.L. Bassler The Vibrio harveyi quorum-sensing system uses shared regulatory components to discriminate between multiple autoinducers Genes Dev. 20 2006 2754 2767
37. D.M. Yebra, S. Kiil, and K. Dam-Johansen Antifouling technology-past, present and future steps towards efficient and environmentally friendly antifouling coatings Prog. Org. Coat. 50 2004 75 104