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

Annals of Microbiology volume 59, pages 359–368 (2009)Cite this article

Abstract

novel antifungal and antibacterial activities of new synthesized phytochemical coumarin compounds [H2L1, HL2 and H2L3] and their copper (II) complexes [L1Cu], [L2Cu(OAc)] and [(L3)Cu2(H2O)4(OAc)2] were evaluated against nine pathogenic fungal species (Alternaria alternata, Aspergillus flavus, Botrytis cinerea, Cladosporium herbarum, Fusarium moniliforme, Helminthosporium tetramera, Penicillium expansum, Rhizopus stolonifer andVerticillium albo-atrum) and eight pathogenic bacterial species, from which four Gram-positive bacteria (Bacillus subtilis, Micrococcus luteus, Staphylococcus citrus andStreptococcus pneumoniae) and four Gram-negative bacteria (Enterobacter aerogenes, Escherichia coli, Pseudomonas aeruginosa andSalmonella typhi). The phytochemical copper (II) complex [L2Cu(OAc)] was the most effective derivative, where it reaches to 90 and 100% inhibition in the most sensitive pathogens (B. subtilis and A. flavus), respectively accompanied with a significant reduction in pectinolytic and cellulytic enzyme activities in all tested pathogenic species. Addition of [L2Cu(OAc)] complex leading to leakage of sugars and electrolytes from the most sensitive microbial cells accompanied with collapsed hyphae ofA. Flavus and membrane blobbing ofB. Subtilis. The production of mycotoxins decreased with the extension exposure to [L2Cu(OAc)] complex reaching to a minimum values for the mycelium originating from the inoculum exposed to the minimum inhibitory concentration (2%). Both aflatoxin (AFB1) and citrinin were the most sensitive toxins.

References

  • Abd-Allah O.A. (2000). Synthesis and biological studies of some benzopyrano[2,3-c]pyrazole derivatves. Farmaco, 55: 641–649.

    Article  PubMed  CAS  Google Scholar 

  • Abdel-Razik A.A. (1970). The parasitism ofSclerotium cepivorum Berck., the incident of white rot of onion. Ph.D. Thesis., Faculty of Agriculture, Assiut University, Egypt.

    Google Scholar 

  • Abu-Salah K.M. (1996). Amphotericin B: an update. Brit. J. Biomed. Sci., 53: 122–133.

    CAS  Google Scholar 

  • A.O.A.C. (2000). Official Methods of Analysis. Association of Official Analytical Chemists Inc., Washington D.C., USA.

    Google Scholar 

  • 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.

    Google Scholar 

  • Avissar S., Drobey S., Pesis E. (1990). Characterization of acetaldehyde effects onRhizopus stolonifer andBotrytis cinerea, Appl. Ann. Biol. 116: 213–220.

    Article  CAS  Google Scholar 

  • Badour S.S. (1959). Analytisch-chemische under suchung des Kalium mangles beiChlorella in vergleich zustanden Diss. Goettingen, Germany.

    Google Scholar 

  • 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.

    Google Scholar 

  • 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.

    Article  PubMed  CAS  Google Scholar 

  • Barnett H.L. (1960). Illustrated Genera of Imperfect Fungi. Burgess Publishing Company, Minneapolis.

    Google Scholar 

  • Barnett H.L., Hunter B.B. (1972). Illustrated Genera of Imperfect Fungi. Burgess Publishing Company, Minneapolis.

    Google Scholar 

  • Bilai V. (1982). Methods of Experimental Mycology, Naukova Dumka, Kiev, Russian.

    Google Scholar 

  • Boutibonnes P. (1979). Determination of the antibacterial activity of various mycotoxins usingBacillus thuringiensis (Berliner). Mycopathology, 67: 45–50.

    Article  CAS  Google Scholar 

  • 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.

    Article  CAS  Google Scholar 

  • 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.

    Article  Google Scholar 

  • Chala A., Weinert J., Wolf G. (2003). An integrated approach to the evaluation of the efficacy of fungicides againstFusarium culmorum, the cause of head blight of wheat. J. Phytopathol., 151: 673–678.

    Article  CAS  Google Scholar 

  • 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.

    Google Scholar 

  • 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.

    Article  PubMed  CAS  Google Scholar 

  • Cociancich S., Ghazi A., Hetru C., Hoffmann J., Letellier L. (1993). Insect defensin, an inducible antibacterial peptide, forms voltage-dependent channels inMicrococcus luteus. J. Biol. Chem., 268: 19239–19245.

    PubMed  CAS  Google Scholar 

  • 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 degradationin vitro. Braz. Arch. Biol. Technol., 50: 725–733.

    Article  Google Scholar 

  • Day R.O., Graham G.G., Williams K.M., Brooks P.M. (1988). Variability in response to NSAIDs. Drugs, 36: 643–651.

    Article  PubMed  CAS  Google Scholar 

  • Devine D.A., Hancock R.E. (2002). Cationic peptides, distribution and mechanisms of resistance. Curr. Pharm., 8: 703–714.

    Article  CAS  Google Scholar 

  • 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.

    Article  PubMed  CAS  Google Scholar 

  • 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.

    Article  CAS  Google Scholar 

  • Emam M.M. (1982). Physiological studies on some thermophilic fungi. M.Sc. Thesis, Faculty of Science, El-Minia University, Egypt.

    Google Scholar 

  • 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 yeastCandida albicans to Amphotericin B and Miconazole. BioMetals, 17: 415–422.

    Article  PubMed  CAS  Google Scholar 

  • Fales F.W. (1951). The estimation and degradation of carbohydrates by yeast cells. J. Biol. Chem., 193: 113–124.

    PubMed  CAS  Google Scholar 

  • Fernandez M.A., Garcia M.D., Saenz M.T. (1996). Antibacterial activity of phenolic acid fractions ofScrophularia frutescens andScrophularia sambucifolia. J. Ethnopharmacol., 53: 11–14.

    Article  PubMed  CAS  Google Scholar 

  • Fischetti V.A., Nelson D., Schuch R. (2006). Reinventing phage therapy: are the parts greater than the sum. Nat. Biotechnol., 24: 1508–1511.

    Article  PubMed  CAS  Google Scholar 

  • Gabor M. (1988). The Pharmacology of Benzopyrane Derivatives and Related Compounds, Akadémiai Kiadó, Budapest.

    Google Scholar 

  • 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.

    PubMed  CAS  Google Scholar 

  • Gilman J.C. (1957). A Manual of Soil Fungi. The Lowastate College Press, Ames, Iowa, USA.

    Google Scholar 

  • Giota A.A., Fylaktakidou K.C., Hadjipavlou-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.

    Article  Google Scholar 

  • Goeger D.E., Hsie A.W., Anderson K.E. (2000). Co-mutagenicity of coumarin (1,2-benzopyrone) with aflatoxin B1 and human liver S9 in mammalian cells. Food Chem. Toxicol., 37: 581–589.

    Google Scholar 

  • Göker H., Boykin D., Yildiz S. (2005). Synthesis and potent antimicrobial activity of some novel 2-phenyl or methyl-4H-1-benzopyran-4-ones carrying amidinobenzimidazoles. Bioorg. Med. Chem., 13: 1707–1714.

    Article  PubMed  CAS  Google Scholar 

  • Gudasi K.B., Havanur V.C., Patil S.A., Patil P.R. (2007). antimicrobial study of newly synthesized lanthanide(iii) complexes of 2-[2-hydroxy-3-methoxyphenyl]-3-[2-hydroxy-3-methoxybenzylamino]-1,2-dihydroquinazolin-4(3H)-one. Metal Based Drugs, pp. 1-7.

  • 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.

    Article  CAS  Google Scholar 

  • Hawker L.E. (1966). Germination: morphological and anatomical changes in the fungus spore. In: Madelin M.F., Ed., Proc. 18th Symp. Colston Res. Soc., Univ. Bristol, Butterworth and Co. Publishers Ltd., London.

    Google Scholar 

  • Hibben C.R., Stotzky G. (1969). Effects of ozone on germination of fungus spores. Can. J. Microbiol., 15: 1187–1196.

    Article  PubMed  CAS  Google Scholar 

  • Hoult J.R., Paya M. (1996). Pharmacological and biochemical actions of simple coumarins: Natural products with therapeutic potential. Gen. Pharmacol., 27: 713–722.

    PubMed  CAS  Google Scholar 

  • Ibrahim A.E. (2005). Biocontrol ofSclerotium cepivorum Berk., the causal agent of white rot disease of onion, by the use of some biocides. MSc. thesis., Fac. Sci., Cairo Univ., Egypt.

    Google Scholar 

  • Jang H., Nde C., Toghrol F., Bentley W. (2008). Microarray analysis of toxicogenomic effects of ortho-phenylphenol inStaphylococcus aureus. BMC Genomics, 9: 411.

    Article  PubMed  CAS  Google Scholar 

  • 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.

    Article  PubMed  CAS  Google Scholar 

  • Jeyachandran R., Mahesh A., Cindrella L., Baskaran X. (2008). Screening antibacterial activity of root extract ofCocculus Hirsutus (L.) Diels used in folklore remedies in South India. J. Plant Sci., 3: 194–198.

    Article  Google Scholar 

  • 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.

    Article  CAS  Google Scholar 

  • Kalkhambkar R.G., Geeta M.K., Chandrappa M.K., Premkumar N., Asdaq S. (2007). Synthesis and biological activities of some new fluorinated coumarins and 1-aza coumarins. Eur. J. Med. Chem., 7: 1–11.

    Google Scholar 

  • Katritzky, A. (1984). Comprehensive Heterocyclic Chemistry, 4th edn., Pergamon Press, New York.

    Google Scholar 

  • 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 glutathioneS-transferase A5 and P1 subunits, and NAD (P)H: quinine oxidoreductase in rat liver. Cancer Res., 60: 957–969.

    PubMed  CAS  Google Scholar 

  • Kertesz Z.I. (1951). The Pectic Substances. Interscience Publishers, New York.

    Google Scholar 

  • 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.

    Article  PubMed  CAS  Google Scholar 

  • Kostova I. (2005). Synthetic and natural coumarins as cytotoxic agents. Curr. Med. Chem.-Anti-cancer Agents, 5: 29–46.

    Article  CAS  Google Scholar 

  • 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.

    Article  PubMed  CAS  Google Scholar 

  • Lewis J.A., Roberts D.P., Hollenbeck M.D. (1991). Induction of cytoplasmic leakage fromRhizoctonia solani hyphae byGliocladium virens and partial characterization of a leakage factor. Biocont. Sci. Technol., 1: 21–29.

    Article  Google Scholar 

  • Liu H., Webio J., Yang B., Yunbo L. (2005). Postharvest BTH treatment induces resistance of peach (Prunus persica L. Cv. Jiubao) fruit to infection byPenicillium expansum and enhances activity of fruit defense mechanisms. Postharvest Biol. Technol., 35: 263–269.

    Article  CAS  Google Scholar 

  • 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.

    Article  CAS  Google Scholar 

  • 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 hinderedo-aminophenol derivatives as antimicrobial agents. Bioorg. Med. Chem. Lett., 16: 5403–5407.

    Article  PubMed  CAS  Google Scholar 

  • Mares D., Tosi B., Romagnoli C., Poli F. (2002). Antifungal activity ofTagetes patula extracts. Pharm. Biol., 40: 400–404.

    Article  CAS  Google Scholar 

  • Maxwell A. (1993). The interaction between coumarin drugs and DNA gyrase. Mol. Microbiol., 4: 681–686.

    Article  Google Scholar 

  • McCulloch P., George W. (1989). Warfarin inhibits metastasis of Mtln3 rat mammary carcinoma without affecting primary tumour growth. Br. J. Cancer, 59: 179–183.

    PubMed  CAS  Google Scholar 

  • Moubasher A.H. (1993). Soil Fungi in Qatar and other Arab Countries. 1st edn., Scientific and Applied Research Center, University of Qatar.

  • 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.

    Article  PubMed  CAS  Google Scholar 

  • 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.

    PubMed  CAS  Google Scholar 

  • Nicolaides D.N., Fylaktakidou K.C., Litinas K.E., Hadjipavlou-Litina D.G. (1998). Eur. J. Med. Chem., 33: 715–717.

    Article  CAS  Google Scholar 

  • Nofal Z., El-Zahar M., El Karim S. (2000). Novel coumarin derivatives with expected biological activity. Bioorg. Med. Chem. Lett., 10: 1195–1198.

    Google Scholar 

  • 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.

    Article  PubMed  CAS  Google Scholar 

  • Parivuguna V., Gnanaprabhal R., Dhanabalan R., Doss A. (2008). Antimicrobial properties and phytochemical constituents ofRheo discolor Hance. Ethnobotan. Leaflets, 12: 841–45.

    Google Scholar 

  • Parry D. (1990). Plant pathology in Agriculture, Cambridge University Press, New York.

    Google Scholar 

  • Raper K.B., Fenell D.L. (1965). The genusAspergillus. Williams Comany Baltimore, USA.

    Google Scholar 

  • Refsum T., Heir E., Kapperud G., Traute V., Holstad G. (2002). Molecular epidemiology ofSalmonella 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.

    Article  CAS  Google Scholar 

  • Richmond D.V., Phillips A. (1975). Effect of benomyl and carbendazim on mitosis in hyphae ofBotrytis cinerea pers. Ex. Pr. and roots ofAllium cepa L. Pest. Biochem. Physiol., 5: 367–379.

    CAS  Google Scholar 

  • Royse D.J., Ries S.M. (1978). The influence of fungi isolated from peach twigs on the pathogenicity ofCitospora cincta. Phytopathology, 68: 603–607.

    Article  Google Scholar 

  • Samson R.A. (1979). A compilation of the Aspergilli described since 1965. Studies in Mycology, 18: 1–39.

    Google Scholar 

  • Sengupta S.K., Pandey O.P., Srivastava B.K., Sharma V.K. (1998). Langerhan cell granulomatosis with unusual FNAC findings. Diag. Cytopathol., 18: 349–351.

    Article  CAS  Google Scholar 

  • 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.

    Article  PubMed  CAS  Google Scholar 

  • Sibbald M.J., Dijl J.M. (2009). Bacterial Secreted Proteins, Secretory Mechanisms and Role in Pathogenesis. Caister Academic Press, Karl Wooldridge Centre for Biomolecular Sciences Publisher.

  • Singh D., Ramesh K., Vandna M., Parikshit T. (2007). Synthesis and characterization of complexes of cyclohexadeca-6,8,14,16-tetraene and their biological screening. Trans. Metal Chem., 32: 1051–1055.

    Article  CAS  Google Scholar 

  • Singleton P.D., Sainsbury D. (1987). Dictionary of Microbiology and Molecular Biology, 2nd edn., Wiley, New York.

    Google Scholar 

  • Tallboys P.W., Busch L.V. (1970). Peptic enzyme produced byVerticillium species. Trans. Brit. Mycol. Soc., 55: 367–381.

    Article  Google Scholar 

  • 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 onin vitro metabolism of aflatoxin B1 by their tissues. Toxicology, 50: 339–348.

    CAS  Google Scholar 

  • Usall J., Teixido N., Torres R., De Eribe X., Vinas I. (2001). Pilot tests ofCandida sake (CPA-1) applications to control postharvest blue mold on apple fruit. Post-harvest Biol. Technol., 21: 147–156.

    Article  Google Scholar 

  • 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.

    Article  CAS  Google Scholar 

  • 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.

    Article  PubMed  Google Scholar 

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    Neveen S. Geweely

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Geweely, N.S. Novel inhibition of some pathogenic fungal and bacterial species by new synthetic phytochemical coumarin derivatives. Ann. Microbiol. 59, 359–368 (2009). https://doi.org/10.1007/BF03178340

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