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

Revista Brasileira de Farmacognosia

Volumn 25, Issue 3, 2015, Pages 199-207

  Quintana, Jairo ^a   Brango Vanegas, José ^a   Costa, Geison M ^a   Castellanos, Leonardo ^a   Arévalo, Catalina ^a   Duque, Carmenza ^a  

^a UNIVERSIDAD NACIONAL DE COLOMBIA   (Colombia)

Author keywords

Biofilm; Furanosesterterpenes; Ircinia felix; Marine products; Quorum sensing

Indexed keywords

ANTIBACTERIAL ACTIVITY; ANTIMICROBIAL ACTIVITY; ARTICLE; AUTORADIOGRAPHY; CHROMOBACTERIUM VIOLACEUM; COLUMN CHROMATOGRAPHY; DISK DIFFUSION; ESCHERICHIA COLI; EUNICEA LACINIATA; EXTRACT; EXTRACTION; GROWTH INHIBITION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; IRCINIA FELIX; MARINE SPECIES; MARINE SPECIES EXTRACT; NEOPETROSIA CARBONARIA; NONHUMAN; PROTON NUCLEAR MAGNETIC RESONANCE; QUORUM SENSING; QUORUM SENSING INHIBITION ACTIVITY; SPONGE (PORIFERA); SVENZEA TUBULOSA; THIN LAYER CHROMATOGRAPHY;

EID: 84940878603     PISSN: None     EISSN: 1981528X     Source Type: Journal    
DOI: 10.1016/j.bjp.2015.03.013     Document Type: Article

References (38)

1. Anta, C., Gonzáles, N., Santafé, G., Rodríguez, J., Jiménez, C., 2002. New Xenia diterpenoids from the Indonesian soft coral Xenia sp. J. Nat. Prod. 65, 766-768.
2. Assmann, M., Lichte, E., Pawlik, J.R., Köck, M., 2000. Chemical defenses of the Caribbean sponges Agelas wiedenmayeri and Agelas conifera. Mar. Ecol. Prog. Ser. 22, 255-262.
3. Blunt, J.W., Copp, B.R., Munro, M.H.G., Northcote, P.T., Prinsep, M.R., 2010. Marine natural products. Nat. Prod. Rep. 27, 165-237.
4. Boyer, M., Wisniewski-Dyé, F., 2009. Cell-cell signalling in bacteria: not simply a matter of quorum. FEMS Microbiol. Ecol. 21, 1-19.
5. Braekman, J.C., Daloze, D., Stoller, C., Van Soest, R.W.M., 1992. Chemotaxonomy of Agelas (Porifera: Demospongiae). Biochem. Syst. Ecol. 20, 417-431.
6. Cafieri, F., Carnuccio, R., Fattorusso, E., Taglialatela-Scafati, O., Vallefuoco, T., 1997. Anti-histaminic activity of bromopyrrole alkaloids isolated from Caribbean Agelas sponges. Bioorg. Med. Chem. Lett. 9, 2283-2288.
7. Carletti, I., Banaigs, B., Amade, P., 2000. Matemone a new bioactive brominecontaining oxindole alkaloid from the Indian Ocean sponge Iotrochota purpurea. J. Nat. Prod. 63, 981-983.
8. Cuadrado, C.T., (Master’s thesis) 2010. Aislamiento de N-acilhomoserinlactonas de algunas bacterias procedentes del Mar Caribe Colombiano, como evidencia de la existencia de circuitos de quorum sensing. Universidad Nacional de Colombia, Bogotá, 270 pp.
9. De Almeida, L.P., Carroll, A.R., Towerzey, L., King, G., McArdle, B.M., Kern, G., 2008. Exiguaquinol: a novel pentacyclic hydroquinone from Neopetrosia exigua that inhibits Helicobacter pylori MurI. Org. Lett. 19, 2585-2588.
10. Dickschat, J.S., 2010. Quorum sensing and bacterial biofilms. Nat. Prod. Rep. 27, 343-369.
11. Dobretsov, S., Teplitski, M., Paul, V., 2009. Mini-review: quorum sensing in the marine environment and its relationship to biofouling. Biofouling 25, 413-427.
12. Dobretsov, S., Teplitski, M., Bayer, M., Gunasekera, S., Proksch, P., Paul, V., 2011. Inhi-bition of marine biofouling by bacterial quorum sensing inhibitors. Biofouling 27, 893-905.
13. Fan, G., Li, Z., Shen, S., Zeng, Y., Yang, Y., Xu, M., 2010. Baculiferins A-O, O-sulfated pyrrole alkaloids with anti-HIV-1 activity, from the Chinese marine sponge Iotrochota baculifera. Bioorg. Med. Chem. 18, 5466-5474.
14. Greenberg, E.P., 2003. Bacterial communication and group behavior. J. Clin. Invest. 112, 1288-1290.
15. Gunasekera, P.S., Sennett, S.H., Kelly-Borgues, M., Bryant, R.W., 1994. Ophirapstanol trisulfate, a new biological active steroid sulfate from the deep water marine sponge Topsentia ophiraphidites. J. Nat. Prod. 57, 1751-1754.
16. Harvell, D., Jordán-Dahlgren, E., Merkel, S., Rosenberg, E., Raymundo, L., Smith, G., Weil, E., 2007. Coral disease environmental drivers, and the balance between coral and microbial associates. Oceanography 20, 172-195.
17. Keifer, P.A., Schwartz, R.E., Koker, M.E.S., Hughes Jr., R.G., Rittschof, D., Rinehart, K.L., 1991. Bioactive bromopyrrole metabolites from the Caribbean sponge Agelas conifera. J. Org. Chem. 56, 2965-2975.
18. Kim, J.S., Kim, Y.H., Seo, Y.W., Park, S., 2007. Quorum sensing inhibitors from the red alga Ahnfeltiopsis flabelliformis. Biotechnol. Bioproc. Eng. 30, 308-311.
19. Kong, F., Burgoyne, D.L., Andersen, J., Allen, T.M., 1992. Pseudoaxinellin, a cyclic heptapeptide isolated from the Papua New Guinea sponge Pseudoaxinella massa. Tetrahedron Lett. 33, 3269-3272.
20. Lhullie, C., Falkenberg, M., Ioannou, E., Quesada, A., Papazafiri, P., Antunes-Horta, P., Schenkel, E.P., Vagias, C., Roussis, V., 2010. Cytotoxic halogenated metabolites from the Brazilian red alga Laurencia catarinensis. J. Nat. Prod. 73, 27-32.
21. Lowery, C.A., Dickerson, T.J., Janda, K.D., 2008. Interspecies and interkingdom communication mediated by bacterial quorum sensing. Chem. Soc. Rev. 37, 1337-1346.
22. Martin, C.A., Hoven, A.D., Cook, A.M., 2008. Therapeutic frontiers: preventing and treating infectious diseases by inhibiting bacterial quorum sensing. Eur. J. Clin. Microbiol. 27, 635-642.
23. Martinez, A., Duque, C., Hara, N., Fujimoto, Y., 1995. Variabilin 11-metiloctadecanoate a branched-chain fatty acid ester of furanosesterpene tetronic acid, from sponge Ircinia felix. Nat. Prod. Lett. 6, 281-284.
24. Martínez, A., Duque, C., Sato, N., Fujimoto, Y., 1997. (8Z, 13Z, 20Z)-strobilinin and (7Z, 13Z, 20Z)-felixinin: new furanosesterterpene tetronic acids from marine sponges of the genus Ircinia. Chem. Pharm. Bull. 45, 181-184.
25. Meseguer, D., Kiil, S., Dam-Johansen, K., 2004. Antifouling technology past, present and future steps towards efficient and environmentally friendly antifouling coatings. Progr. Org. Coat. 50, 75-104.
26. Mora-Cristancho, J.A., Arevalo-Ferro, C., Ramos, F.A., Tello, E., Duque, C., Lhullier, C., Falkenberg, M., Schenkel, E.P., 2011. Antifouling activities against colonizer marine bacteria of extracts from marine invertebrates collected in the Colombian Caribbean Sea and on the Brazilian Coast (Santa Catarina). Z. Naturforsch. C 66, 515-526.
27. Nakao, Y., Shiroiwa, T., Murayama, S., Matsunaga, S., Goto, Y., Matsumoto, Y., 2004. Identification of Renieramycin A as an antileishmanial substance in a marine sponge Neopetrosia sp. Mar. Drugs 25, 55-62.
28. Ng, W.L., Bassler, B.L., 2009. Bacterial quorum-sensing network architectures. Annu. Rev. Genet. 17, 197-222.
29. Osorno, O., Castellanos, L., Ramos, F.A., Arévalo, C., 2012. Gas chromathography as a tool in quorum sensing studies. In: Salih, B., ¸ elikbıc¸ ak, Ö. (Org.). Gas Chromatography Biochemicals, Narcotics and Essential Oils. Intech, Croatia, pp. 67-96.
30. Peters, L., König, G.M., Wright, A.D., Pukall, R., Stackebrandt, E., Eberl, L., 2003. Secondary metabolites of Flustra foliacea and their influence on bacteria. Appl. Environ. Microbiol. 69, 3469-3475.
31. Qian, P.Y., Lau, S.C.K., Dahms, H.U., Dobretsov, S., Harder, T., 2007. Marine biofilms as mediators of colonization by marine macroorganisms: implications for antifouling and aquaculture. Mar. Biotechnol. 12, 399-410.
32. Rasmussen, T.B., Givskov, M., 2006. Quorum sensing inhibitors as anti-pathogenic drugs. Int. J. Med. Microbiol. 296, 149-161.
33. Shen, X., Perry, T.L., Dunbar, C.D., Kelly-Borges, M., Hamann, M.T., 1998. Debromosceptrin, an alkaloid from the Caribbean sponge Agelas conifera. J. Nat. Prod. 61, 1302-1303.
34. Sjöstrand, U., Kornprobst, J.M., Djerassi, C., 1981. Minor and trace sterols from marine invertebrates 29 (22E)-ergosta-5,22,25-trien-3 -ol and (22E,24R)-24,26-dimethylcholesta-5,22,25(27)-trien-3 -ol. Two new marine sterols from the sponge Pseudopxinella lunachata. Steroids 38, 355-364.
35. Skindersoe, M., Ettinger-Epstein, P., Rasmussen, T., Bjarnsholt, T., De Nys, R., Givskov, M., 2008. Quorum sensing antagonism from marine organisms. Mar. Biotechnol. 20, 56-63.
36. Teplitski, M., Ritchie, K., 2009. How feasible is the biological control of coral diseases? Trends Ecol. Evol. 24, 378-385.
37. Thale, Z., Johnson, T., Tenney, K., Wenzel, P.J., Lobkovsky, E., Clardy, J., 2002. Structures and 24 cytotoxic properties of sponge-derived bisannulated acridines. J. Org. Chem. 67, 9384-9391.
38. Yang, S.W., Chan, T.M., Pomponi, S.A., Chen, G., Wright, A.E., Patel, M., 2003. A new bicyclic guanidine alkaloid, Sch 575948, from a marine Sponge, Ptilocaulis spiculifer. J. Antibiot. 56, 970-972.