Novel inhibition of some pathogenic fungal and bacterial species by new synthetic phytochemical coumarin derivatives

Annals of Microbiology

Volumn 59, Issue 2, 2009, Pages 359-368

  Geweely, Neveen S ^a  

^a CAIRO UNIVERSITY   (Egypt)

Author keywords

Antibacterial; Antifungal; Coumarin; Enzymes; Toxin

Indexed keywords

ALTERNARIA ALTERNATA; ASPERGILLUS FLAVUS; BACILLUS SUBTILIS; BACTERIA (MICROORGANISMS); BOTRYOTINIA FUCKELIANA; CITRUS; CLADOSPORIUM; DAVIDIELLA TASSIANA; ENTEROBACTER AEROGENES; ESCHERICHIA COLI; FUNGI; GIBBERELLA FUJIKUROI; MICROCOCCUS LUTEUS; NEGIBACTERIA; PENICILLIUM EXPANSUM; POSIBACTERIA; PSEUDOMONAS AERUGINOSA; RHIZOPUS; RHIZOPUS STOLONIFER; SALMONELLA TYPHI; STAPHYLOCOCCUS; STREPTOCOCCUS PNEUMONIAE;

EID: 77955492722     PISSN: 15904261     EISSN: 18692044     Source Type: Journal    
DOI: 10.1007/BF03178340     Document Type: Article

References (82)

1. Abd-Allah O.A. (2000). Synthesis and biological studies of some benzopyrano[2,3-c]pyrazole derivatves. Farmaco, 55: 641-649.
2. Abdel-Razik A.A. (1970). The parasitism of Sclerotium cepivorum Berck., the Incident of white rot of onion. Ph.D. Thesis., Faculty of Agriculture, Assiut University, Egypt.
3. Abu-Salah K.M. (1996). Amphotericin B: an update. Brit. J. Biomed. Sci., 53: 122-133.
4. A.O.A.C. (2000). Official Methods of Analysis. Association of Official Analytical Chemists Inc., Washington D.C., USA.
5. Atef N.M. (2000). In vitro antagonistic action of egg plant and sweet potato phylloplane bacteria to some parasitic fungi. Phytopathol. Mediterr. 39: 366-375.
6. Avissar S., Drobey S., Pesis E. (1990). Characterization of acetaldehyde effects on Rhizopus stolonifer and Botrytis cinerea, Appl. Ann. Biol. 116: 213-220.
7. Badour S.S. (1959). Analytisch-chemische under suchung des Kalium mangles bei Chlorella in vergleich zustanden Diss. Goettingen, Germany.
8. Bagihalli G.B., Avaji P.G., Patil S.A., Badami P.S. (2008). Synthesis, spectral characterization, in vitro antibacterial, antifungal and cytotoxic activities of Co(II), Ni(II), and Cu(II) complexes with 1,2,4-triazole Schiff bases. Eur. J. Med. Chem., 10: 10-16.
9. Balasubramanian K.P., Parameswari K., Chinnusamy V., Prabhakaran R., Natarajan K. (2006). Synthesis, characterization, electro chemistry, catalytic and biological activities of ruthenium(III) complexes with bidentate N, O/S donor ligands. Spectrochimica Acta, 65: 678-683.
10. Barnett H.L. (1960). Illustrated Genera of Imperfect Fungi. Burgess Publishing Company, Minneapolis.
11. Barnett H.L., Hunter B.B. (1972). Illustrated Genera of Imperfect Fungi. Burgess Publishing Company, Minneapolis.
12. Bilai V. (1982). Methods of Experimental Mycology, Naukova Dumka, Kiev, Russian.
13. Boutibonnes P. (1979). Determination of the antibacterial activity of various mycotoxins using Bacillus thuringiensis (Berliner). Mycopathology, 67: 45-50.
14. Budzisz E., Brzezinska E., Krajewska U., Rozalski M. (2003). European cytotoxic effects, alkylating properties and molecular modelling of coumarin derivatives and their phosphonic analogues. J. Med. Chem., 38: 597-603.
15. Castoria R., De Curtis F., Lima, G., Caputo L., Pacifico S., Cicco V. (2001). Aureobasidium pullulans (LS-30) an antagonist of post-harvest pathogens of fruits: study on its modes of action. Post-harvest Biol. Technol., 22: 7-17.
16. Chala A., Weinert J., Wolf G. (2003). An integrated approach to the evaluation of the efficacy of fungicides against Fusarium culmorum, the cause of head blight of wheat. J. Phytopathol., 151: 673-678.
17. Chandra S., Raizada S., Tyagi M., Gautam A. (2007). Synthesis, spectroscopic, and antimicrobial studies on bivalent nickel and copper complexes of bis(thiosemicrbazone). Bioinorg. Chem. Appl., 17: 514-583.
18. Chimenti F., Secci D., Bolasco A., Chimenti P., Granese A., Befani O., Turini P., Alcaro S., Ortuso F. (2004). Inhibition of monoamine oxidases by coumarin-3-acyl derivatives: biological activity and computational study. Bioorg. Med. Chem. Lett., 14: 3697-3703.
19. Cociancich S., Ghazi A., Hetru C., Hoffmann J., Letellier L. (1993). Insect defensin, an inducible antibacterial peptide, forms voltage-dependent channels in Micrococcus luteus. J. Biol. Chem., 268: 19239-19245.
20. Coelho A.R., Celli M.G., Ono E.Y., Wosiacki G., Hoffmann F.L., Pagnocca F.C., Hirooka E.Y. (2007). Penicillium expansum versus antagonist yeasts and patulin degradation in vitro. Braz. Arch. Biol. Technol., 50: 725-733.
21. Day R.O., Graham G.G., Williams K.M., Brooks P.M. (1988). Variability in response to NSAIDs. Drugs, 36: 643-651.
22. Devine D.A., Hancock R.E. (2002). Cationic peptides, distribution and mechanisms of resistance. Curr. Pharm., 8: 703-714.
23. Ellis G.A., Blake D.R. (1993). Why are non-steroidal anti-inflammatory drugs so variable in their efficacy, a description of ion trapping. Ann. Rheum. Dis., 52: 241-243.
24. El-Tabl A., El-saied F., Alhakimi A. (2008). Spectroscopic characterization and biological activity of metal complexes with an ONO trifunctionalized hydrozone ligand. J. Coord. Chem., 61: 2380-2401.
25. Emam M.M. (1982). Physiological studies on some thermophilic fungi. M.Sc. Thesis, Faculty of Science, El-Minia University, Egypt.
26. Eshwika A., Coyle B., Devereux M., McCann M., Kavanagh K. (2004). Metal complexes of 1,10-phenanthroline-5,6-dione alter the susceptibility of the yeast Candida albicans to Amphotericin B and Miconazole. BioMetals, 17: 415-422.
27. Fales F.W. (1951). The estimation and degradation of carbohydrates by yeast cells. J. Biol. Chem., 193: 113-124.
28. Fernandez M.A., Garcia M.D., Saenz M.T. (1996). Antibacterial activity of phenolic acid fractions of Scrophularia frutescens and Scrophularia sambucifolia. J. Ethnopharmacol., 53: 11-14.
29. Fischetti V.A., Nelson D., Schuch R. (2006). Reinventing phage therapy: are the parts greater than the sum. Nat. Biotechnol., 24: 1508-1511.
30. Gabor M. (1988). The Pharmacology of Benzopyrane Derivatives and Related Compounds, Akadémiai Kiadó, Budapest.
31. Gao Y. Belkum M.J., Stiles M.E. (1999). The outer membrane of Gram-negative bacteria inhibits antibacterial activity of brochocin-C. Appl. Environ. Microbiol., 65, 4329-4333.
32. Gilman J.C. (1957). A Manual of Soil Fungi. The Lowastate College Press, Ames, Iowa, USA.
33. Giota A.A., Fylaktakidou K.C., Hadjlpavlou-Litina D.J., Litinas K.E., Nicolaides D.N. (2001). Synthesis and biological evalution of several 3-(coumarin-4-yl)tetrahydroisoxazole and 3-(coumarin-4-yl)dihydropyrazole derivatives. J. Heterocycl. Chem., 38: 717-722.
34. 1 and human liver S9 in mammalian cells. Food Chem. Toxicol., 37: 581-589.
35. Göker H., Boykin D., Yildiz S. (2005). Synthesis and potent antimicrobial activity of some novel 2-phenyl or methyl-4H-1benzopyran-4-ones carrying amidinobenzimidazoles. Bioorg. Med. Chem., 13: 1707-1714.
36. Gudasi K.B., Havanur V.C., Patli S.A., Patil P.R. (2007). antimicrobial study of newly synthesized lanthanide(iii) complexes of 2-[2-hydroxy-3- methoxyphenyl]-3-[2hydroxy-3-methoxybenzylamino]-1,2-dihydroquinazolin4(3H)-one. Metal Based Drugs, pp. 1-7.
37. Groopman J.D., Cain L.G., Kensler T.W. (1988). Aflatoxin exposure in human populations: measurements and relationship to cancer, CRC Crit. Rev. Toxicol., 19: 113-145.
38. th Symp. Colston Res. Soc., Univ. Bristol, Butterworth and Co. Publishers Ltd., London.
39. Hibben C.R., Stotzky G. (1969). Effects of ozone on germination of fungus spores. Can. J. Microbiol., 15: 1187-1196.
40. Hoult J.R., Paya M. (1996). Pharmacological and biochemical actions of simple coumarins: Natural products with therapeutic potential. Gen. Pharmacol., 27: 713-722.
41. Ibrahim A.E. (2005). Blocontrol of Sclerotium cepivorum Berk., the causal agent of white rot disease of onion, by the use of some biocides. MSc. thesis., Fac. Sci., Cairo Univ., Egypt.
42. Jang H., Nde C., Toghrol F., Bentley W. (2008). Microarray analysis of toxicogenomic effects of ortho-phenylphenol in Staphylococcus aureus. BMC Genomics, 9: 411.
43. Janisiewicz W.J., Tworkoski T.J., Sharer C.A. (2000). Characterizing the mechanism of biological control of post-harvest diseases on fruits with a simple method to study competition for nutrients. Phytopathology, 90: 1196-1200.
44. Jeyachandran R., Mahesh A., Cindrella L., Baskaran X. (2008). Screening antibacterial activity of root extract of Cocculus hirsutus (L.) Diels used in folklore remedies in South India. J. Plant Sci., 3: 194-198.
45. Jian L., Tingting L., Sulan C., Xin W., Lei L., Yongmei W. (2006). Synthesis, structure and biological activity of cobalt(II) and copper(II) complexes of valine-derived schiff bases. J. Inorg. Biochem., 100: 1888-1896.
46. Kalkhambkar R.G., Geeta M.K., Chandrappa M.K., Premkumar N., Asdaq S. (2007). Synthesis and biological activities of some new fluorinated coumarlns and 1-aza coumarins. Eur. J. Med. Chem., 7: 1-11.
47. th edn., Pergamon Press, New York.
48. Kelly V.P., Ellis E.M., Manson M.M., Chanas S.A., Moffat G.J., McLeod R., Judah D.J., Neal G.E., Hayes J.D. (2000). Chemoprevention of aflatoxin B1 hepatocarcinogenesis by coumarin, a natural benzopyrone that is a potent inducer of aflatoxIn B1-aldehyde reductase, the glutathione S-transferase A5 and P1 subunits, and NAD (P)H: quinine oxidoreductase in rat liver. Cancer Res., 60: 957-969.
49. Kertesz Z.I. (1951). The Pectic Substances. Interscience Publishers, New York.
50. Kontogiorgis C.A., Hadjipavlou-Litina D.J. (2004). Synthesis and biological evaluation of novel coumarin derivatives with a 7-azomethine linkage. Bioorg. Med. Chem. Lett., 14: 611-614.
51. Kostova I. (2005). Synthetic and natural coumarins as cytotoxic agents. Curr. Med. Chem.-Anti-cancer Agents, 5: 29-46.
52. Krivobok S., Olivier P., Marzin D., Seigle-Murandi F., Steiman R. (1987). Study of the genotoxic potential of 17 mycotoxins with the SOS Chromotest. Mutagenesis, 2: 433-439.
53. Lewis J.A., Roberts D.P., Hollenbeck M.D. (1991). Induction of cytoplasmic leakage from Rhizoctonia solani hyphae by Gliocladlum virens and partial characterization of a leakage factor. Biocont. Sci. Technol., 1: 21-29.
54. Liu H., Webio J., Yang B., Yunbo L. (2005). Postharvest BTH treatment induces resistance of peach (Prunus persica L. Cv. Jiubao) fruit to infection by Penicillium expansum and enhances activity of fruit defense mechanisms. Postharvest Biol. Technol., 35: 263-269.
55. Loginova N.V., Koval'chuk T.V., Polozov G.I., Osipovich N.P. Rytik P.G., Kucherov I.I., Chernyavskaya A.A., Sorokin V.L., Shadyro O.I. (2006a). Synthesis, characterization, antifungal and anti-HIV activities of metal(II) complexes of 4,6-di-tertbutyl-3-[(2-hydroxyethyl)thio]benzene-1,2-diol. Polyhedron, 25: 3603-3610.
56. Loginova N.V., Koval'chuk T.V., Zheldakova R.A., Osipovich N.P., Sorokin V.L., Polozov G.I., Ksendzova G.A., Glushonok G.K., Chernyavskaya A.A., Shadyro O.I. (2006b). Synthesis and biological evaluation of copper (II) complexes of sterically hindered o-aminophenol derivatives as antimicrobial agents. Bioorg. Med. Chem. Lett., 16: 5403-5407.
57. Mares D., Tosi B., Romagnoll C., Poli F. (2002). Antifungal activity of Tagetes patula extracts. Pharm. Biol., 40: 400-404.
58. Maxwell A. (1993). The interaction between coumarin drugs and DNA gyrase. Mol. Microbiol., 4: 681-686.
59. McCulloch P., George W. (1989). Warfarin Inhibits metastasis of Mtln3 rat mammary carcinoma without affecting primary tumour growth. Br. J. Cancer, 59: 179-183.
60. st edn., Scientific and Applied Research Center, University of Qatar.
61. Musicki B., Periers A., Laurin P., Ferroud D., Benedetti Y., Lachaud S., Chatreaux F., Haesslein J., Iltis A., Pierre C., Khider J., Tessot N., Airault M., Demassey J., Dupuis-Hamelin C., Lassaigne P., Bonnefoy A., Vicat P., Klich M. (2000). Improved antibacterial activities of coumarin antibiotics bearing 50, 50-dialkylnoviose. Bioorg. Med. Chem. Lett., 10: 1695-1699.
62. Nakajima Y., Ishibashi J., Yukuhiro F., Asaoka A., Taylor D., Yamakawa M. (2003). Antibacterial activity and mechanism of action of tick defensin against Gram-positive bacteria. Biochim. Biophys. Acta, 1624: 125-130.
63. Nicolaides D.N., Fylaktakidou K.C., Litinas K.E., HadjipavlouLitina D.G. (1998). Eur. J. Med. Chem., 33: 715-717.
64. Nofal Z., El-Zahar M., El Karim S. (2000). Novel coumarin derivatives with expected biological activity. Bioorg. Med. Chem. Lett., 10: 1195-1198.
65. Panneerselvam P., Rajasree R., Gudaparthi V., Ekambaram H., Subramanian S., Krishnan S. (2005). Synthesis of Schiff bases of 4-(4-aminophenyl)- morpholine as potential antimicrobial agents. Eur. J. Med. Chem., 40: 225-229.
66. Parivuguna V., Gnanaprabhal R., Dhanabalan R., Doss A. (2008). Antimicrobial properties and phytochemical constituents of Rheo discolor Hance. Ethnobotan. Leaflets, 12: 841-45.
67. Parry D. (1990). Plant pathology in Agriculture, Cambridge University Press, New York.
68. Raper K.B., Fenell D.L. (1965). The genus Aspergillus. Williams Comany Baltimore, USA.
69. Refsum T., Heir E., Kapperud G., Traute V., Holstad G. (2002). Molecular epidemiology of Salmonella enterica serovar Typhimurium Isolates determined by pulsed-field gel electrophoresis: comparison of isolates from avian wildlife, domestic animals, and the environment in Norway. Appl. Environ. Microbiol., 11: 5600-5606.
70. Richmond D.V., Phillips A. (1975). Effect of benomyl and carbendazim on mitosis in hyphae of Botrytis cinerea pers. Ex. Pr. and roots of Allium cepa L Pest. Biochem. Physiol., 5: 367-379.
71. Royse D.J., Ries S.M. (1978). The influence of fungi isolated from peach twigs on the pathogenicity of Citospora cincta. Phytopathology, 68: 603-607.
72. Samson R.A. (1979). A compilation of the Aspergilli described since 1965. Studies in Mycology, 18: 1-39.
73. Sengupta S.K., Pandey O.P., Srlvastava B.K., Sharma V.K. (1998). Langerhan cell granulomatosis with unusual FNAC findings. Diag. Cytopathol., 18: 349-351.
74. Shen Q., Peng Q., Shao J., Liu X., Huang Z., Pu X., Ma L., Li Y., Chan A., Gu L. (2005). Synthesis and biological evaluation of functionalized coumarins as acetylcholinesterase inhibitors. Eur. J. Med. Chem., 40: 1307-1315.
75. Sibbald M.J., Diji J.M. (2009). Bacterial Secreted Proteins, Secretory Mechanisms and Role in Pathogenesis. Caister Academic Press, Karl Wooldridge Centre for Blomolecular Sciences Publisher.
76. Singh D., Ramesh K., Vandna M., Parikshit T. (2007). Synthesis and characterization of complexes of cyclohexadeca6,8,14,16-tetraene and their biological screening. Trans. Metal Chem., 32: 1051-1055.
77. nd edn., Wiley, New York.
78. Tallboys P.W., Busch L.V. (1970). Peptic enzyme produced by Verticillium species. Trans. Brit. Mycol. Soc., 55: 367-381.
79. Tulayakul P., Dong K., Li J., Manabe N., Kumagai S. (2007). The effect of feeding piglets with the diet containing green tea extracts or coumarin on In vitro metabolism of aflatoxin B1 by their tissues. Toxicology, 50: 339-348.
80. Usall J., Teixido N., Torres R., De Eribe X., Vinas I. (2001). Pilot tests of Candida sake (CPA-1) applications to control postharvest blue mold on apple fruit. Post-harvest Biol. Technol., 21: 147-156.
81. Venkateswarlu B., Ramesh K. (1993). Cell membrane stability and biochemical response of cultured cells of groundnut under polyethylene glycol-induced water stress, Plant Sci., 90: 179-185.
82. Yu J., Cleveland T., Nierman W., Bennett J. (2005). Aspergillus flavus genomics: gateway to human and animal health, food safety, and crop resistance to diseases. Rev. Iberoam. Micol., 22: 194-202.