New insights into the antibacterial activity of hydroxycoumarins against ralstonia solanacearum

Molecules

Volumn 21, Issue 4, 2016, Pages

  Yang, Liang ^a   Ding, Wei ^a   Xu, Yuquan ^b   Wu, Dousheng ^a   Li, Shili ^a   Chen, Juanni ^a   Guo, Bing ^a  

^a SOUTHWEST UNIVERSITY   (China)

^b INSTITUTE OF PLANT PROTECTION   (China)

Author keywords

Antibacterial activity; Bacterial wilt; Biofilm inhibition; Daphnetin; Esculetin; Hydroxycoumarins; Ralstonia solanacearum

Indexed keywords

ANTIINFECTIVE AGENT; BACTERIAL PROTEIN; COUMARIN DERIVATIVE; DAPHNETIN; FLIA PROTEIN, BACTERIA; SIGMA FACTOR; UMBELLIFERONE DERIVATIVE;

BIOFILM; BIOSYNTHESIS; CELL MEMBRANE; DRUG EFFECTS; GENE EXPRESSION REGULATION; GROWTH, DEVELOPMENT AND AGING; MICROBIAL SENSITIVITY TEST; MICROBIOLOGY; PATHOGENICITY; PLANT DISEASE; RALSTONIA SOLANACEARUM; TOMATO; TRANSMISSION ELECTRON MICROSCOPY; ULTRASTRUCTURE;

ANTI-BACTERIAL AGENTS; BACTERIAL PROTEINS; BIOFILMS; CELL MEMBRANE; COUMARINS; GENE EXPRESSION REGULATION, BACTERIAL; LYCOPERSICON ESCULENTUM; MICROBIAL SENSITIVITY TESTS; MICROSCOPY, ELECTRON, TRANSMISSION; PLANT DISEASES; RALSTONIA SOLANACEARUM; SIGMA FACTOR; UMBELLIFERONES;

EID: 84969528830     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules21040468     Document Type: Article

References (49)

1. Genin, S. Molecular traits controlling host range and adaptation to plants in Ralstonia solanacearum. New Phytologist. 2010, 187, 920-928.
2. De Oliveira Monteiro, F.M. Environmental Cues Controlling the Pathogenicity of "Ralstonia Solanacearum" on Plants: Señales Ambientales Que Determinan la Patogenicidad de "Ralstonia Solanacearum" en Plantas. Ph.D. Thesis, Universitat de Barcelona, Barcelona, Spain, 2013.
3. Elphinstone, J.G.; Allen, C.; Prior, P.; Hayward, A.C. The current bacterial wilt situation: A global overview. In Bacterial Wilt Disease and the Ralstonia Solanacearum Species Complex; American Phytopathological Society: St Paul, MN, USA, 2005; pp. 9-28.
4. Yuliar, Y.A.N.; Toyota, K. Recent trends in control methods for bacterial wilt diseases caused by Ralstonia solanacearum. Microbes Environ. 2015, 30, 1. [CrossRef] [PubMed]
5. Denny, T. Plant pathogenic Ralstonia species. In Plant-Associated Bacteria; Springer: Dordrecht, The Netherlands, 2006; pp. 573-644.
6. Lin, Y.; He, Z.; Rosskopf, E.N.; Conn, K.L.; Powell, C.A; Lazarovits, G. A nylon membrane bag assay for determination of the effect of chemicals on soilborne plant pathogens in soil. Plant Dis. 2010, 94, 201-206.
7. Wang, X.; Liu, X.; Han, H. Evaluation of antibacterial effects of carbon nanomaterials against copper-resistant Ralstonia solanacearum. Colloids Surf. B Biointerfaces 2013, 103, 136-142.
8. Álvarez, B.; Biosca, E.G.; López, M.M. On the life of Ralstonia solanacearum, a destructive bacterial plant pathogen. In Current Research, Technology and Education Topics in Applied Microbiology and Microbial Biotechnology; Formatex Research Center: Badajoz, Spain, 2010; Volume 1.
9. Hayward, A.C. Biology and epidemiology of bacterial wilt caused by Pseudomonas solanacearum. Annu. Rev. Phytopathol. 1991, 29, 65-87.
10. Li, L.; Feng, X.; Tang, M.; Hao, W.; Han, Y.; Zhang, G.; Wan, S. Antibacterial activity of Lansiumamide B to tobacco bacterial wilt (Ralstonia solanacearum). Microbiol. Res. 2014, 169, 522-526.
11. Zhao, X.; Mei, W.; Gong, M.; Zuo, W.; Bai, H.; Dai, H. Antibacterial activity of the flavonoids from Dalbergia odorifera on Ralstonia solanacearum. Molecules 2011, 16, 9775-9782.
12. Hassan, M.A.E.; Bereika, M.F.F.; Abo-Elnaga, H.I.G.; Sallam, M.A.A. Direct antimicrobial activity and induction of systemic resistance in potato plants against bacterial wilt disease by plant extracts. Plant Pathol. J. 2009, 25, 352-360
13. Abo-Elyousr, K.A.; Seleim, M.A.; Abd-El-Moneem, K.M.; Saead, F.A. Integrated effect of Glomus mosseae and selected plant oils on the control of bacterial wilt disease of tomato. Crop Prot. 2014, 66, 67-71.
14. Paret, M.L.; Cabos, R.; Kratky, B.A.; Alvarez, A.M. Effect of plant essential oils on Ralstonia solanacearum race 4 and bacterial wilt of edible ginger. Plant Dis. 2010, 94, 521-527.
15. Fan, W.W.; Yuan, G.Q.; Li, Q.Q.; Lin, W. Antibacterial mechanisms of methyl gallate against Ralstonia solanacearum. Australas. Plant Pathol. 2014, 43, 1-7.
16. Barot, K.P.; Jain, S.V.; Kremer, L.; Singh, S.; Ghate, M.D. Recent advances and therapeutic journey of coumarins: Current status and perspectives. Med. Chem. Res. 2015, 24, 2771-2798.
17. Céspedes, C.L.; Avila, J.G.; Martínez, A.; Serrato, B.; Calderón-Mugica, J.C.; Salgado-Garciglia, R. Antifungal and antibacterial activities of Mexican tarragon (Tagetes lucida). J. Agric. Food Chem. 2006, 54, 3521-3527.
18. Saleem, M.; Nazir, M.; Ali, M.S.; Hussain, H.; Lee, Y.S.; Riaz, N.; Jabbar, A. Antimicrobial natural products: An update on future antibiotic drug candidates. Nat. Prod. Rep. 2010, 27, 238-254.
19. Yu, Y.M. The Antibacterial Effects and Mechanism of Several Botanical Compounds against Ralstonia solanacearum. Master's Thesis, Southwest University, Chongqing, China, 2015.
20. Lin, M.H.; Chou, Y.S.; Tsai, Y.J.; Chou, D.S. Antioxidant properties of 5, 7-dihydroxycoumarin derivatives in in vitro cell-free and cell-containing systems. J. Exp. Clin. Med. 2011, 3, 126-131.
21. Jurd, L.; Corse, J.; King, A.D.; Bayne, H.; Mihara, K. Antimicrobial properties of 6,7-dihydroxy-, 7,8-dihydroxy-, 6-hydroxy-and 8-hydroxycoumarins. Phytochemistry 1971, 10, 2971-2974.
22. Nazari, Z.E.; Iranshahi, M. Biologically active sesquiterpene coumarins from Ferula species. Phytother. Res. 2011, 25, 315-323.
23. Konc, J.T.; Hejchman, E.; Kruszewska, H.; Wolska, I.; Maciejewska, D. Synthesis and pharmacological activity of O-aminoalkyl derivatives of 7-hydroxycoumarin. Eur. J. Med. Chem. 2011, 46, 2252-2263.
24. Khan, R.; Bhat, K.A.; Raja, A.F.; Shawl, A.S.; Alam, M.S. Isolation, characterisation and antibacterial activity studies of coumarins from Rhododendron lepidotum Wall. ex G. Don, Ericaceae. Rev. Bras. Farmacogn. 2010, 20, 886-890.
25. Kabeya, L.M.; da Silva, C.H.; Kanashiro, A.; Campos, J.M.; Azzolini, A.E.C.; Polizello, A.C.M.; Pupo, M.T.; Lucisano-Valim, Y.M. Inhibition of immune complex-mediated neutrophil oxidative metabolism: A pharmacophore model for 3-phenylcoumarin derivatives using GRIND-based 3D-QSAR and 2D-QSAR procedures. Eur. J. Med. Chem. 2008, 43, 996-1007.
26. Tan, F.; Shi, B.; Li, J.; Wu, W.; Zhang, J. Design and synthesis of new 2-aryl-4, 5-dihydro-thiazole analogues: In vitro antibacterial activities and preliminary mechanism of action. Molecules 2015, 20, 20118-20130.
27. Witaicenis, A.; Seito, L.N.; da Silveira Chagas, A.; de Almeida, L.D.; Luchini, A.C.; Rodrigues-Orsi, P.; Cestari, S.H.; Di Stasi, L.C. Antioxidant and intestinal anti-inflammatory effects of plant-derived coumarin derivatives. Phytomedicine 2014, 21, 240-246.
28. Turkmen, N.; Velioglu, Y.S.; Sari, F.; Polat, G. Effect of extraction conditions on measured total polyphenol contents and antioxidant and antibacterial activities of black tea. Molecules 2007, 12, 484-496.
29. Maddox, C.E.; Laur, L.M.; Tian, L. Antibacterial activity of phenolic compounds against the phytopathogen Xylella fastidiosa. Curr. Microbiol. 2010, 60, 53-58.
30. Xu, J.; Zhou, F.; Ji, B.P.; Pei, R.S.; Xu, N. The antibacterial mechanism of carvacrol and thymol against Escherichia coli. Lett. Appl. Microbiol. 2008, 47, 174-179.
31. Hassan, S.; Mathesius, U. The role of flavonoids in root-rhizosphere signalling: Opportunities and challenges for improving plant-microbe interactions. J. Exp. Bot. 2012, 63, 3429-3444.
32. Kawase, M.; Sakagami, H.; Hashimoto, K.; Tani, S.; Hauer, H.; Chatterjee, S.S. Structure-cytotoxic activity relationships of simple hydroxylated coumarins. Anticancer Res. 2002, 23, 3243-3246.
33. Yao, J.; Allen, C. The plant pathogen Ralstonia solanacearum needs aerotaxis for normal biofilm formation and interactions with its tomato host. J. Bacteriol. 2007, 189, 6415-6424.
34. Kai, K.; Shimizu, B.I.; Mizutani, M.; Watanabe, K.; Sakata, K. Accumulation of coumarins in Arabidopsis thaliana. Phytochemistry 2006, 67, 379-386.
35. Gnonlonfin, G.B.; Sanni, A.; Brimer, L. Review scopoletin-A coumarin phytoalexin with medicinal properties. Crit. Rev. Plant Sci. 2012, 31, 47-56. [CrossRef]
36. Cowan, M.M. Plant products as antimicrobial agents. Clin. Microbiol. Rev. 1999, 12, 564-582.
37. Strathmann, M.; Wingender, J.; Flemming, H.C. Application of fluorescently labelled lectins for the visualization and biochemical characterization of polysaccharides in biofilms of Pseudomonas aeruginosa. J. Microbiol. Methods 2002, 50, 237-248.
38. Genin, S.; Denny, T.P. Pathogenomics of the Ralstonia solanacearum species complex. Annu. Rev. Phytopathol. 2012, 50, 67-89.
39. Peeters, N.; Guidot, A.; Vailleau, F.; Valls, M. Ralstonia solanacearum, a widespread bacterial plant pathogen in the post-genomic era. Mol. Plant Pathol. 2013, 14, 651-662.
40. Zhang, L.; Xu, J.; Xu, J.; Zhang, H.; He, L.; Feng, J. TssB is essential for virulence and required for type VI secretion system in Ralstonia solanacearum. Microb. Pathog. 2014, 74, 1-7.
41. Wu, D.; Ding, W.; Zhang, Y.; Liu, X.; Yang, L. Oleanolic acid induces the type III secretion system of Ralstonia solanacearum. Front. Microbiol. 2015, 6, 1466. [CrossRef] [PubMed]
42. Yoshimochi, T.; Zhang, Y.; Kiba, A.; Hikichi, Y.; Ohnishi, K. Expression of hrpG and activation of response regulator HrpG are controlled by distinct signal cascades in Ralstonia solanacearum. J. Gen. Plant Pathol. 2009, 75, 196-204.
43. Dalgaard, P.; Ross, T.; Kamperman, L.; Neumeyer, K.; McMeekin, T.A. Estimation of bacterial growth rates from turbidimetric and viable count data. Int. J. Food Microbiol. 1994, 23, 391-404.
44. Andrews, J.M. Determination of minimum inhibitory concentrations. J. Antimicrob. Chemother. 2001, 48 (Suppl. 1), 5-16.
45. Smyth, T.; Ramachandran, V.N.; Smyth, W.F. A study of the antimicrobial activity of selected naturally occurring and synthetic coumarins. Int. J. Antimicrob. Agents 2009, 33, 421-426.
46. Galal, A.A.; Kehil, Y.E.I.; El-Daoudi, Y.H.; Shihata, Z.A.; Ouf, M.F. A Comparative Study on the Identification of Races and Biovars of some Egyptian Isolates of Ralsionia solanaceamm. Egypt J. Phytopathol. 2003, 31, 103-117.
47. Tans-Kersten, J.; Brown, D.; Allen, C. Swimming motility, a virulence trait of Ralstonia solanacearum, is regulated by FlhDC and the plant host environment. Mol. Plant Microbe Interact. 2004, 17, 686-695.
48. Chen, J.; Peng, H.; Wang, X.; Shao, F.; Yuan, Z.; Han, H. Graphene oxide exhibits broad-spectrum antimicrobial activity against bacterial phytopathogens and fungal conidia by intertwining and membrane perturbation. Nanoscale 2014, 6, 1879-1889.
49. Monteiro, F.; Genin, S.; van Dijk, I.; Valls, M. A luminescent reporter evidences active expression of Ralstonia solanacearum type III secretion system genes throughout plant infection. Microbiology 2012, 158, 2107-2116.