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BioMed Research International
Volume 2014, Article ID 248656, 9 pages
http://dx.doi.org/10.1155/2014/248656
Research Article

Antibacterial and Antioxidant Activities of Derriobtusone A Isolated from Lonchocarpus obtusus

1Laboratory of Biologically Active Molecules, Biochemistry and Molecular Biology Department, Federal University of Ceará, 60.440-970 Fortaleza, CE, Brazil
2Institute for Biotechnology and Bioengineering (IBB), Centre of Biological Engineering, University of Minho, 4710-057 Braga, Portugal
3Integrated Laboratory of Biomolecules (LIBS), Department of Pathology and Legal Medicine, Federal University of Ceará, 62.042-280 Fortaleza, CE, Brazil
4Marine Natural Products Laboratory, Department of Fishing Engineering, Federal University of Ceará, 60.440-970 Fortaleza, CE, Brazil
5Centre of Exact Sciences and Technology, Acaraú Valley State University, 62.040-370 Sobral, CE, Brazil
6Department of Organic and Inorganic Chemistry, Federal University of Ceará, 60.021-940 Fortaleza, CE, Brazil

Received 27 February 2014; Accepted 9 May 2014; Published 1 June 2014

Academic Editor: Sebastien Fiorucci

Copyright © 2014 Mayron Alves Vasconcelos et al. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Linked References

  1. W. M. Dunne Jr., “Bacterial adhesion: seen any good biofilms lately?” Clinical Microbiology Reviews, vol. 15, no. 2, pp. 155–166, 2002. View at Publisher · View at Google Scholar · View at Scopus
  2. I. B. Beech, J. A. Sunner, and K. Hiraoka, “Microbe-surface interactions in biofouling and biocorrosion processes,” International Microbiology, vol. 8, no. 3, pp. 157–168, 2005. View at Google Scholar · View at Scopus
  3. P. H. Mc Cay, A. A. Ocampo-Sosa, and G. T. A. Fleming, “Effect of subinhibitory concentrations of benzalkonium chloride on the competitiveness of Pseudomonas aeruginosa grown in continuous culture,” Microbiology, vol. 156, no. 1, pp. 30–38, 2010. View at Publisher · View at Google Scholar · View at Scopus
  4. M. R. Hall, E. McGillicuddy, and L. J. Kaplan, “Biofilm: basic principles, pathophysiology, and implications for clinicians,” Surgical Infections, vol. 15, no. 1, pp. 1–7, 2014. View at Publisher · View at Google Scholar
  5. C. N. Murphy and S. Clegg, “Klebsiella pneumoniae and type 3 fimbriae: nosocomial infection, regulation and biofilm formation,” Future Microbiology, vol. 7, no. 8, pp. 991–1002, 2012. View at Publisher · View at Google Scholar · View at Scopus
  6. J. L. Brooks and K. K. Jefferson, “Staphylococcal biofilms. Quest for the magic bullet,” Advances in Applied Microbiology, vol. 81, pp. 63–87, 2012. View at Publisher · View at Google Scholar · View at Scopus
  7. F. Mika and R. Hengge, “Small regulatory RNAs in the control of motility and biofilm formation in E. coli and Salmonella,” International Journal of Molecular Sciences, vol. 14, no. 3, pp. 4560–4579, 2013. View at Publisher · View at Google Scholar · View at Scopus
  8. A. Sher, “Antimicrobial activity of natural products from medicinal plants,” Gomal Journal of Medical Sciences, vol. 7, no. 1, pp. 72–78, 2009. View at Google Scholar
  9. D. Savoia, “Plant-derived antimicrobial compounds: alternatives to antibiotics,” Future Microbiology, vol. 7, no. 8, pp. 979–990, 2012. View at Publisher · View at Google Scholar · View at Scopus
  10. V. Kuete, “Potential of Cameroonian plants and derived products against microbial infections: a review,” Planta Medica, vol. 76, no. 14, pp. 1479–1491, 2010. View at Publisher · View at Google Scholar · View at Scopus
  11. M. Artini, R. Papa, G. Barbato et al., “Bacterial biofilm formation inhibitory activity revealed for plant derived natural compounds,” Bioorganic and Medicinal Chemistry, vol. 20, no. 2, pp. 920–926, 2012. View at Publisher · View at Google Scholar · View at Scopus
  12. L. Cobrado, M. M. Azevedo, A. Silva-Dias, J. P. Ramos, C. Pina-Vaz, and A. G. Rodrigues, “Cerium, chitosan and hamamelitannin as novel biofilm inhibitors?” Journal of Antimicrobial Chemotherapy, vol. 67, no. 5, pp. 1159–1162, 2012. View at Publisher · View at Google Scholar · View at Scopus
  13. I. Hernández, L. Alegre, F. van Breusegem, and S. Munné-Bosch, “How relevant are flavonoids as antioxidants in plants?” Trends in Plant Science, vol. 14, no. 3, pp. 125–132, 2009. View at Publisher · View at Google Scholar · View at Scopus
  14. K. Asada, “Production and scavenging of reactive oxygen species in chloroplasts and their functions,” Plant Physiology, vol. 141, no. 2, pp. 391–396, 2006. View at Publisher · View at Google Scholar · View at Scopus
  15. F. van Breusegem and J. F. Dat, “Reactive oxygen species in plant cell death,” Plant Physiology, vol. 141, no. 2, pp. 384–390, 2006. View at Publisher · View at Google Scholar · View at Scopus
  16. K. Brieger, S. Schiavone, F. J. Miller Jr., and K. Krause, “Reactive oxygen species: from health to disease,” Swiss Medical Weekly, vol. 142, Article ID w13659, 2012. View at Publisher · View at Google Scholar · View at Scopus
  17. S. A. Stanner, J. Hughes, C. N. M. Kelly, and J. Buttriss, “A review of the epidemiological evidence for the ‘antioxidant hypothesis’,” Public Health Nutrition, vol. 7, no. 3, pp. 407–422, 2004. View at Publisher · View at Google Scholar · View at Scopus
  18. P. G. Waterman and E. N. Mahmoud, “Flavonoids from the seeds of Lonchocarpus costaricensis,” Phytochemistry, vol. 24, no. 3, pp. 571–574, 1985. View at Google Scholar · View at Scopus
  19. A. F. Magalhães, C. C. Santos, E. G. Magalhães, and M. A. Nogueira, “Detection of polyhydroxyalkaloids in Lonchocarpus extracts by GC-MS of acetylated derivatives,” Phytochemical Analysis, vol. 13, no. 4, pp. 215–221, 2002. View at Publisher · View at Google Scholar · View at Scopus
  20. M. C. Nascimento, R. L. V. Dias, and W. B. Mors, “Flavonoids of Derris obtusa: aurones and auronols,” Phytochemistry, vol. 15, no. 10, pp. 1553–1558, 1976. View at Google Scholar · View at Scopus
  21. E. L. Santos, E. V. Costa, F. A. Marques et al., “Toxicity and antioxidant activity of flavonoids from Lonchocarpus filipes root bark,” Quimica Nova, vol. 32, no. 9, pp. 2255–2258, 2009. View at Google Scholar · View at Scopus
  22. M. G. B. Cavalcante, R. M. Silva, P. N. Bandeira et al., “Furanoflavones and other chemical constituents of Lonchocarpus obtusos,” Journal of the Brazilian Chemical Society, vol. 23, no. 2, pp. 301–305, 2012. View at Publisher · View at Google Scholar · View at Scopus
  23. J. P. Brown, “A review of the genetic effects of naturally occurring flavonoids, anthraquinones and related compounds,” Mutation Research, vol. 75, no. 3, pp. 243–277, 1980. View at Google Scholar · View at Scopus
  24. M. H. Pan, C. S. Lai, and C. T. Ho, “Anti-inflammatory activity of natural dietary flavonoids,” Food and Function, vol. 1, no. 1, pp. 15–31, 2010. View at Publisher · View at Google Scholar · View at Scopus
  25. M. Kawai, T. Hirano, S. Higa et al., “Flavonoids and related compounds as anti-allergic substances,” Allergology International, vol. 56, no. 2, pp. 113–123, 2007. View at Publisher · View at Google Scholar · View at Scopus
  26. N. Masuoka, M. Matsuda, and I. Kubo, “Characterisation of the antioxidant activity of flavonoids,” Food Chemistry, vol. 131, no. 2, pp. 541–545, 2012. View at Publisher · View at Google Scholar · View at Scopus
  27. W. Ren, Z. Qiao, H. Wang, L. Zhu, and L. Zhang, “Flavonoids: promising anticancer agents,” Medicinal Research Reviews, vol. 23, no. 4, pp. 519–534, 2003. View at Publisher · View at Google Scholar · View at Scopus
  28. T. P. T. Cushnie and A. J. Lamb, “Antimicrobial activity of flavonoids,” International Journal of Antimicrobial Agents, vol. 26, no. 5, pp. 343–356, 2005. View at Publisher · View at Google Scholar · View at Scopus
  29. T. P. T. Cushnie and A. J. Lamb, “Recent advances in understanding the antibacterial properties of flavonoids,” International Journal of Antimicrobial Agents, vol. 38, no. 2, pp. 99–107, 2011. View at Publisher · View at Google Scholar · View at Scopus
  30. M. Roussaki, S. C. Lima, A. Kypreou, P. Kefalas, A. C. Silva, and A. Detsi, “Aurones: a promising heterocyclic scaffold for the development of potent antileishmanial agents,” International Journal of Medicinal Chemistry, vol. 2012, Article ID 196921, 8 pages, 2012. View at Publisher · View at Google Scholar
  31. T. Iwashina, “The structure and distribution of the flavonoids in plants,” Journal of Plant Research, vol. 113, no. 1111, pp. 287–299, 2000. View at Google Scholar · View at Scopus
  32. R. Haudecoeur and A. Boumendjel, “Recent advances in the medicinal chemistry of aurones,” Current Medicinal Chemistry, vol. 19, no. 18, pp. 2861–2875, 2012. View at Google Scholar · View at Scopus
  33. S. Stepanović, D. Vuković, I. Dakić, B. Savić, and M. Švabić-Vlahović, “A modified microtiter-plate test for quantification of staphylococcal biofilm formation,” Journal of Microbiological Methods, vol. 40, no. 2, pp. 175–179, 2000. View at Publisher · View at Google Scholar · View at Scopus
  34. X. J. Duan, W. W. Zhang, X. M. Li, and B. G. Wang, “Evaluation of antioxidant property of extract and fractions obtained from a red alga, Polysiphonia urceolata,” Food Chemistry, vol. 95, no. 1, pp. 37–43, 2006. View at Publisher · View at Google Scholar · View at Scopus
  35. T. Wang, R. Jónsdóttir, and G. Ólafsdóttir, “Total phenolic compounds, radical scavenging and metal chelation of extracts from Icelandic seaweeds,” Food Chemistry, vol. 116, no. 1, pp. 240–248, 2009. View at Publisher · View at Google Scholar
  36. P. Ganesan, C. S. Kumar, and N. Bhaskar, “Antioxidant properties of methanol extract and its solvent fractions obtained from selected Indian red seaweeds,” Bioresource Technology, vol. 99, no. 8, pp. 2717–2723, 2008. View at Publisher · View at Google Scholar · View at Scopus
  37. Y. L. Chew, Y. Y. Lim, M. Omar, and K. S. Khoo, “Antioxidant activity of three edible seaweeds from two areas in South East Asia,” LWT—Food Science and Technology, vol. 41, no. 6, pp. 1067–1072, 2008. View at Publisher · View at Google Scholar · View at Scopus
  38. M. R. Parsek and P. K. Singh, “Bacterial biofilms: an emerging link to disease pathogenesis,” Annual Review of Microbiology, vol. 57, pp. 677–701, 2003. View at Publisher · View at Google Scholar · View at Scopus
  39. F. M. Millezi, M. O. Pereira, N. N. Batista et al., “Susceptibility of monospecies and dual-species biofilms of Staphylococcus aureus and Escherichia coli to essential oils,” Journal of Food Safety, vol. 32, no. 3, pp. 351–359, 2012. View at Publisher · View at Google Scholar · View at Scopus
  40. D. F. Magalhães, A. M. G. A. Tozzi, E. G. Magalhães, M. Sannomiya, A. D. P. C. Soriano, and M. A. F. Perez, “Flavonoids of Lonchocarpus montanus A.M.G. Azevedo and biological activity,” Annals of the Brazilian Academy of Sciences, vol. 79, no. 3, pp. 351–367, 2007. View at Google Scholar
  41. Y. Rukayadi, K. Lee, S. Han, D. Yong, and J. K. Hwang, “In vitro activities of panduratin A against clinical Staphylococcus strains,” Antimicrobial Agents and Chemotherapy, vol. 53, no. 10, pp. 4529–4532, 2009. View at Publisher · View at Google Scholar · View at Scopus
  42. M. M. Radwan, R. Rodriguez-Guzman, S. P. Manly, M. Jacob, and S. A. Ross, “Sepicanin A—a new geranyl flavanone from Artocarpus sepicanus with activity against methicillin-resistant Staphylococcus aureus (MRSA),” Phytochemistry Letters, vol. 2, no. 4, pp. 141–143, 2009. View at Publisher · View at Google Scholar · View at Scopus
  43. L. E. Alcaraz, S. E. Blanco, O. N. Puig, F. Tomas, and F. H. Ferretti, “Antibacterial activity of flavonoids against methicillin-resistant Staphylococcus aureus strains,” Journal of Theoretical Biology, vol. 205, no. 2, pp. 231–240, 2000. View at Publisher · View at Google Scholar · View at Scopus
  44. A. Basile, S. Sorbo, S. Giordano et al., “Antibacterial and allelopathic activity of extract from Castanea sativa leaves,” Fitoterapia, vol. 71, supplement 1, pp. S110–S116, 2000. View at Publisher · View at Google Scholar · View at Scopus
  45. Y. Sato, S. Suzaki, T. Tishikawa, M. Kihara, H. Shibata, and T. Higuti, “Phytochemical flavones isolated from Scutellaria barbata and antibacterial activity against methicillin-resistant Staphylococcus aureus,” Journal of Ethnopharmacology, vol. 72, no. 3, pp. 483–488, 2000. View at Publisher · View at Google Scholar
  46. A. Vikram, G. K. Jayaprakasha, P. R. Jesudhasan, S. D. Pillai, and B. S. Patil, “Suppression of bacterial cell-cell signalling, biofilm formation and type III secretion system by citrus flavonoids,” Journal of Applied Microbiology, vol. 109, no. 2, pp. 515–527, 2010. View at Publisher · View at Google Scholar · View at Scopus
  47. H. Q. Li, L. Shi, Q. S. Li et al., “Synthesis of C(7) modified chrysin derivatives designing to inhibit β-ketoacyl-acyl carrier protein synthase III (FabH) as antibiotics,” Bioorganic and Medicinal Chemistry, vol. 17, no. 17, pp. 6264–6269, 2009. View at Publisher · View at Google Scholar · View at Scopus
  48. N. C. Gordon and D. W. Wareham, “Antimicrobial activity of the green tea polyphenol (-)-epigallocatechin-3-gallate (EGCG) against clinical isolates of Stenotrophomonas maltophilia,” International Journal of Antimicrobial Agents, vol. 36, no. 2, pp. 129–131, 2010. View at Publisher · View at Google Scholar · View at Scopus
  49. D. Wu, Y. Kong, C. Han et al., “D-alanine:D-alanine ligase as a new target for the flavonoids quercetin and apigenin,” International Journal of Antimicrobial Agents, vol. 32, no. 5, pp. 421–426, 2008. View at Publisher · View at Google Scholar · View at Scopus
  50. A. Budzyńska, M. Rózalski, W. Karolczak, M. Wieckowska-Szakiel, B. Sadowska, and B. Rózalska, “Synthetic 3-arylideneflavanones as inhibitors of the initial stages of biofilm formation by Staphylococcus aureus and Enterococcus faecalis,” Zeitschrift für Naturforschung C: Journal of Biosciences, vol. 66, no. 3-4, pp. 104–114, 2011. View at Google Scholar · View at Scopus
  51. W. F. Liljemark, C. G. Bloomquist, and G. R. Germaine, “Effect of bacterial aggregation on the adherence of oral streptococci to hydroxyapatite,” Infection and Immunity, vol. 31, no. 3, pp. 935–941, 1981. View at Google Scholar · View at Scopus
  52. J. H. Lee, S. C. Regmi, J. A. Kim et al., “Apple flavonoid phloretin inhibits Escherichia coli O157:H7 biofilm formation and ameliorates colon inflammation in rats,” Infection and Immunity, vol. 79, no. 12, pp. 4819–4827, 2011. View at Publisher · View at Google Scholar · View at Scopus
  53. M. A. Rendón, Z. Saldaña, A. L. Erdem et al., “Commensal and pathogenic Escherichia coli use a common pilus adherence factor for epithelial cell colonization,” Proceedings of the National Academy of Sciences of the United States of America, vol. 104, no. 25, pp. 10637–10642, 2007. View at Publisher · View at Google Scholar · View at Scopus
  54. K. E. Heim, A. R. Tagliaferro, and D. J. Bobilya, “Flavonoid antioxidants: chemistry, metabolism and structure-activity relationships,” Journal of Nutritional Biochemistry, vol. 13, no. 10, pp. 572–584, 2002. View at Publisher · View at Google Scholar · View at Scopus
  55. N. Balasundram, K. Sundram, and S. Samman, “Phenolic compounds in plants and agri-industrial by-products: antioxidant activity, occurrence, and potential uses,” Food Chemistry, vol. 99, no. 1, pp. 191–203, 2006. View at Publisher · View at Google Scholar · View at Scopus
  56. T. Narsinghani, M. C. Sharma, and S. Bhargav, “Synthesis, docking studies and antioxidant activity of some chalcone and aurone derivatives,” Medicinal Chemistry Research, vol. 22, no. 9, pp. 4059–4068, 2013. View at Publisher · View at Google Scholar · View at Scopus
  57. E. N. Frankel and A. S. Meyer, “The problems of using one-dimensional methods to evaluate multifunctional food and biological antioxidants,” Journal of the Science of Food and Agriculture, vol. 80, no. 13, pp. 1925–1940, 2000. View at Publisher · View at Google Scholar
  58. C. Cruces-Blanco, A. S. Carretero, E. M. Boyle, and A. F. Gutiérrez, “The use of dansyl chloride in the spectrofluorimetric determination of the synthetic antioxidant butylated hydroxyanisole in foodstuffs,” Talanta, vol. 50, no. 5, pp. 1099–1108, 1999. View at Publisher · View at Google Scholar · View at Scopus
  59. O. Farkas, J. Jakus, and K. Héberger, “Quantitative structure—antioxidant activity relationships of flavonoid compounds,” Molecules, vol. 9, no. 12, pp. 1079–1088, 2004. View at Google Scholar · View at Scopus
  60. G. Cao, E. Sofic, and R. L. Prior, “Antioxidant and prooxidant behavior of flavonoids: structure-activity relationships,” Free Radical Biology and Medicine, vol. 22, no. 5, pp. 749–760, 1997. View at Publisher · View at Google Scholar · View at Scopus
  61. S. Burda and W. Oleszek, “Antioxidant and antiradical activities of flavonoids,” Journal of Agricultural and Food Chemistry, vol. 49, no. 6, pp. 2774–2779, 2001. View at Google Scholar · View at Scopus
  62. C. A. Rice-Evans, N. J. Miller, and G. Paganga, “Structure-antioxidant activity relationships of flavonoids and phenolic acids,” Free Radical Biology and Medicine, vol. 20, no. 7, pp. 933–956, 1996. View at Publisher · View at Google Scholar · View at Scopus