Antimicrobial activity of euplotin C, the sesquiterpene taxonomic marker from the marine ciliate Euplotes crassus

Antimicrobial Agents and Chemotherapy

Volumn 48, Issue 10, 2004, Pages 3828-3833

  Savoia, Dianella ^a   Avanzini, Claudio ^a   Allice, Tiziano ^a   Callone, Emanuela ^b   Guella, Graziano ^b   Dini, Fernando ^c  

^a UNIVERSITY OF TURIN   (Italy)

^b UNIVERSITY OF TRENTO   (Italy)

^c UNIVERSITY OF PISA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

EUPLOTIN C; PLANT MEDICINAL PRODUCT; SESQUITERPENE; TERPENOID; UNCLASSIFIED DRUG;

ANTIMICROBIAL ACTIVITY; ANTIPROTOZOAL ACTIVITY; ARTICLE; BURKHOLDERIA CEPACIA; CANDIDA ALBICANS; CELL CULTURE; CELL LINE; CYTOTOXICITY; DOSE RESPONSE; ESCHERICHIA COLI; EUPLOTES; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; INCUBATION TIME; INTRACELLULAR KILLING; LD 50; LEISHMANIA INFANTUM; LEISHMANIA MAJOR; MICROCOCCUS LUTEUS; NONHUMAN; PRIORITY JOURNAL; PROMASTIGOTE; PROTEUS VULGARIS; PSEUDOMONAS AERUGINOSA; SOLUBILITY; STAPHYLOCOCCUS AUREUS; STREPTOCOCCUS PYOGENES; TAXONOMIC IDENTIFICATION;

ANIMALS; ANTI-INFECTIVE AGENTS; BIOLOGICAL MARKERS; CANDIDA ALBICANS; CELL LINE; DOSE-RESPONSE RELATIONSHIP, DRUG; EUPLOTES; GRAM-NEGATIVE BACTERIA; GRAM-POSITIVE BACTERIA; KINETICS; LEISHMANIA INFANTUM; LEISHMANIA MAJOR; MACROPHAGES; MICE; SESQUITERPENES;

EID: 4644248186     PISSN: 00664804     EISSN: None     Source Type: Journal    
DOI: 10.1128/AAC.48.10.3828-3833.2004     Document Type: Article

References (46)

1. Akendengue, B., F. Roblot, P. M. Loiseau, C. Bories, E. Ngou-Milama, A. Laurens, and R. Hocquemiller. 2002. Klaivanolide, an antiprotozoal lactone from Uvaria klaineana. Phytochemistry 59:885-888.
2. Aungst, R. A., Jr., and R. L. Funk. 2001. Synthesis of (Z)-2-acyl-2-enals via retrocycloadditions of 5-acyl-4-alkyl-4H-1,3-dioxins: application in the total synthesis of the cytotoxin (±)-euplotin A. J. Am. Chem. Soc. 123:9455-9456.
3. Bidwell, J., and S. Spotte. 1985. Artificial seawaters: formulas and methods. Jones and Barlett Publishers, Boston, Mass.
4. Brendle, J. J., A. Outlaw, A. Kumar, D. W. Boykin, D. A. Patrick, R. R. Tidwell, and K. A. Werbovetz. 2002. Antileishmanial activities of several classes of aromatic dications. Antimicrob. Agents Chemother. 46:797-807.
5. Camacho, M. R., R. Mata, P. Castaneda, G. C. Kirby, D. C. Warhust, S. L. Croft, and J. D. Phillipson. 2000. Bioactive compounds from Celaenodendron mexicanum. Planta Med. 66:463-468.
6. Chan-Bacah, M. J., and L. M. Pena-Rodriguez. 2001. Plant natural products with leishmanicidal activity. Nat. Prod. Rep. 18:674-688.
7. Choi, D. H., S. Shin, and I. K. Park. 1999. Characterization of antimicrobial agents extracted from Asterina pectifera. Int. J. Antimicrob. Agents 11:65-68.
8. Cosentino, S., C. I. Tuberoso, B. Pisano, M. Satta, V. Mascia, E. Arzedi, and F. Palmas. 1999. In-vitro antimicrobial activity and chemical composition of Sardinian Thymus essential oils. Lett. Appl. Microbiol. 29:130-135.
9. Cowan, M. M. 1999. Plant products as antimicrobial agents. Clin. Microbiol. Rev. 12:564-582.
10. Croft, S. L., D. Snowdon, and V. Yardley. 1996. The activities of four anticancer alkyllysophospholipids against Leishmania donovani, Trypanosoma cruzi and Trypanosoma brucei. J. Antimicrob. Chemother. 38:1041-1047.
11. Croft, S. L., K. Seifert, and M. Duchene. 2002. Antiprotozoal activities of phospholipid analogues. Mol. Biochem. Parasitol. 126:165-172.
12. Debitus, C., G. Guella, I. I. Mancini, J. Waikedre, J. P. Guemas, J. L. Nicolas, and F. Pietra. 1998. Quinolones from a bacterium and tyrosine metabolites from its host sponge, Suberea creba from the Coral Sea. J. Mar. Biotechnol. 6:136-141.
13. Delorenzi, J. C., M. Attias, C. R. Gattass, M. Andrade, C. Rezende, A. da Cunha Pinto, A. T. Henriques, D. C. Bou-Habib, and E. M. Saraiva. 2001. Antileishmanial activity of an indole alkaloid from Peschiera australis. Antimicrob. Agents Chemother. 45:1349-1354.
14. Delorenzi, J. C., L. Freire-de-Lima, C. R. Gattass, D. de Andrade Costa, L. He, M. E. Kuehne, and E. M. Saraiva. 2002. In vitro activities of iboga alkaloid congeners coronaridine and 18-methoxycoronaridine against Leishmania amazonensis. Antimicrob. Agents Chemother. 46:2111-2115.
15. Di Giorgio, C., F. Delmas, N. Filloux, M. Robin, L. Seferian, N. Azas, M. Gasquet, M. Costa, P. Timon-David, and J. P. Galy. 2003. In vitro activity of 7-substituted 9-chloro and 9-amino-2-methoxyacridines and their bis- and tetra-acridine complexes against Leishmania infantum. Antimicrob. Agents Chemother. 47:174-180.
16. Dini, F., G. Guella, P. Giubbilini, I. Mancini, and F. Pietra. 1993. Control of interspecific relationships in marine ciliate protists by most evolved natural products. Naturwiss. Organ Max. 80:84-86.
17. Dini, F., and D. Nyberg. 1999. Growth rates of marine ciliates on diverse organisms reveal ecological specialization within morphospecies. Microb. Ecol. 37:13-22.
18. El-Tahir, A., G. M. Satti, and S. A. Khalid. 1999. Antiplasmodial activity of selected Sudanese medicinal plants with emphasis on Acacia nilotica. Phytother. Res. 13:474-478.
19. Guella, G., F. Dini, A. Tomei, and F. Pietra. 1994. Preuplotin, a putative biogenetic precursor of the euplotins, bioactive sesquiterpenoids of the marine ciliated protist Euplotes crassus. J. Chem. Soc., Perkin Trans. 1:161-166.
20. Guella, G., F. Dini, and F. Pietra. 1996. Rarisetenolide, epoxyrarisetenolide and epirarisetenolide, new skeleton sesquiterpene lactones as taxonomic markers and defensive agents of the marine ciliated morphospecies Euplotes rariseta. Helvet. Chim. Acta 79:2180-2189.
21. Guella, G., F. Dini, and F. Pietra. 1996. Epoxyfocardin and its putative biogenetic precursor, focardine, bioactive, new skeleton diterpenoids of the marine ciliate Euplotes focardii from Antarctica. Helvet. Chim. Acta 79:439-448.
22. Guella, G., F. Dini, and F. Pietra. 1996. Hydrolytic breakdown of the euplotins, highly strained, adaptive, hemiacetal esters of the marine ciliate Euplotes crassus: a mimic of degradative pathway in nature and a trick for the assignment of the absolute configuration. Helvet. Chim. Acta 79:710-717.
23. 30 backbone from marine ciliates. Angew. Chem. 38:1134-1136.
24. Guella, G., E. Callone, I. Mancini, G. Uccello-Barretta, F. Balzano, and F. Dini. 2004. Chemical and structural properties of the inclusion complex of euplotin C with heptakis(2,6 di-O-methyl)-β-cyclodextrin through NMR. Electrospray mass spectrometry and molecular mechanics investigations. Eur. J. Org. Chem., in press.
25. Hentschel, U., M. Schmid, M. Wagner, L. Fieseler, C. Gernert, and J. Hacker. 2001. Isolation and phylogenetic analysis of bacteria with antimicrobial activities from the Mediterranean sponges Aplysina aerophoba and Aplysina cavernicola. FEMS Microbiol. Ecol. 35:305-312.
26. Isnansetyo, A., and Y. Kamei. 2003. Pseudoalteromonas phenolica sp. nov., a novel marine bacterium that produces phenolic anti-methicillin-resistant Staphylococcus aureus substances. Int. J. Syst. Evol. Microbiol. 53:583-588.
27. Jiang, S., J. Meadows, S. A. Anderson, and A. J. Mukkada. 2002. Antileishmanial activity of the antiulcer agent omeprazole. Antimicrob. Agents Chemother. 46:2569-2574.
28. Kayser, O., A. F. Kiderlen, H. Laatsch, and S. L. Croft. 2000. In vitro leishmanicidal activity of monomeric and dimeric naphthoquinones. Acta Trop. 77:307-314.
29. Kayser, O., A. F. Kiderlen, S. Bertels, and K. Siems. 2001. Antileishmanial activities of aphidicolin and its semisynthetic derivatives. Antimicrob. Agents Chemother. 45:288-292.
30. Kayser, O., A. F. Kiderlen, and S. L. Croft. 2003. Antileishmanial activity of two γ-pyrones from Podolepsis hieracioides (Asteraceae). Acta Trop. 86:105-107.
31. Keysari, Y. 1992. A colorimetric microtiter assay for the quantitation of cytokine activity on adherent cells in tissue culture. J. Immunol. Methods 146:155-161.
32. Laurent, D., G. Guella, M. F. Roquebert, F. Farinole, I. Mancini, and F. Pietra. 2000. Cytotoxins, mycotoxins and drugs from a new deuteromycete, Acremonium neo-caledoniae, from the southwestern lagoon of New Caledonia. Planta Med. 66:63-66.
33. Lazaro, J. E., J. Nitcheu, R. Z. Predicala, G. C. Mangalindan, F. Nesslany, D. Marzin, G. P. Concepcion, and B. Diquet. 2002. Heptyl prodigiosin, a bacterial metabolite, is antimalarial in vivo and non-mutagenic in vitro. J. Nat. Toxins 11:367-377.
34. Mangena, T., and N. Y. Muyima. 1999. Comparative evaluation of the antimicrobial activities of essential oils of Artemisia afra, Pteronia incana and Rosmarinus officinalis on selected bacteria and yeast strains. Lett. Appl. Microbiol. 28:291-296.
35. Nagaraj, G., M. V. Uma, M. S. Shivayogi, and H. Balaram. 2001. Antimalarial activities of peptide antibiotics isolated from fungi. Antimicrob. Agents Chemother. 45:145-149.
36. Nakatsu, T., B. N. Ravi, and D. J. Faulkner. 1981. Antimicrobial constituents of Udotea flabellum. J. Org. Chem. 46:2435-2438.
37. NCCLS. 2002. Performance standards for antimicrobial susceptibility testing. Suppl. M 100-S12. NCCLS, Wayne, Pa.
38. Neal, R. A., S. L. Croft, and D. J. Nelson. 1985. Anti-leishmanial effect of allopurinol ribonucleoside and the related compounds, allopurinol, thiopurinol, thiopurinol ribonucleoside, and of formycin B, sinefungin and the lepidine WR6026. Trans. R. Soc. Trop. Med. Hyg. 79:122-128.
39. Oketch-Rabah, H. A., S. F. Dossaji, S. B. Christensen, K. Frydenvang, E. Lemmich, C. Cornett, C. E. Olsen, M. Chen, A. Kharazmi, and T. Theander. 1997. Antiprotozoal compounds from Asparagus africanus. J. Nat. Prod. 60:1017-1022.
40. Pant, B., Y. Kato, T. Kumagai, T. Matsuoka, and M. Sugiyama. 1997. Blepharismin produced by a protozoan Blepharisma functions as an antibiotic against methicillin-resistant Staphylococcus aureus. FEMS Microbiol. Lett. 155:67-71.
41. Pietra, F. 1995. Structurally similar natural products in phylogenetically distant marine organisms, and a comparison with terrestrial species. Chem. Soc. Rev. 1995:65-71.
42. Ricci, N., C. Capovani, and F. Dini. 1999. Behavioural modifications imposed to ciliate protist, Euplotes crassus, by caulerpenyne: the major toxic terpenoid of the green seaweed, Caulerpa taxifolia. Eur. J. Protistol. 35:290-303.
43. Rosa, M. D. S. S., R. R. Mendonca-Filho, H. R. Bizzo, I. de Almeida Rodrigues, R. M. Soares, T. Souto-Padron, C. Sales Alviano, and A. H. Lopes. 2003. Antileishmanial activity of a linalool-rich essential oil from Croton cajucara. Antimicrob. Agents Chemother. 47:1895-1901.
44. Savoia, D., C. Avanzini, S. Conti, V. Magliani, R. Frazzi, and L. Polonelli. 2002. In vitro leishmanicidal activity of a monoclonal antibody mimicking a yeast killer toxin. J. Eukatyot. Microbiol. 49:319-323.
45. Sundar, S., T. K. Jha, C. P. Thakur, J. Engel, H. Sindermann, C. Fischer, K. Junge, A. Bryceson, and J. Berman. 2002. Oral miltefosine for Indian visceral leishmaniasis. N. Engl. J. Med. 347:1739-1746.
46. Taylor, A. E. R., and J. R. Baker. 1978. Methods of cultivating parasites in vitro, p. 55-58. Academic Press, New York, N.Y.