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Purification and characterization of new fatty acids with antibiotic activity produced bySporothrix flocculosa

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Abstract

Chloroform extracts from a culture broth of the biocontrol fungusSporothrix flocculosa were separated by thin-layer chromatography (TLC). Compounds with antifungal activity were revealed with theCladosporium cucumerinum bioassay on TLC plates and were isolated by using silica gel column, preparative TLC, and reverse-phase high-performance liquid chromatography (RP-HPLC). They were identified by standard methods of nuclear magnetic resonance (NMR), gas chromatography (GC), mass spectrometry (MS), and infrared spectrum (IR). In addition to an active molecule previously described, two new fatty acids with antibiotic activity were characterized, 9-heptadecenoic acid and 6-methyl-9-heptadecenoic acid, the latter displaying the strongest activity among all three active molecules. This high number of active metabolites produced byS. flocculosa would explain its rapid and strong activity as a biocontrol agent of powdery mildews. In this context, screening ofS. flocculosa isolates for increased production of these molecules should help in selection of candidates with superior biocontrol properties.

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References

  • Andersson, B. A., andHolman, R. T. 1975. Mass spectrometric localization of methyl branching in fatty acids using acylpyrrolidines.Lipids 10:716–718.

    PubMed  CAS  Google Scholar 

  • Bayliss, M. 1936. Effect of the chemical constitution of soaps upon their germicidal properties.J. Bacteriol. 31:489–504.

    PubMed  CAS  Google Scholar 

  • Bélanger, R. R., Labbé, C., andJarvis, W. R. 1994. Commercial-scale control of rose powdery mildew with a fungal antagonist.Plant Dis. 78:420–424.

    Google Scholar 

  • Black, S. 1985. Inhibition of the reductive activation of valyl-tRNA synthethase from yeast by unsaturated fatty acids and associated observations on newly found lipohilic substances from yeast.J. Biol. Chem. 260:433–440.

    PubMed  CAS  Google Scholar 

  • Choudhury, S. R., Traquair, J. A., andJarvis, W. R. 1994. 4-Methyl-7,11-heptadecadenal and 4-methyl-7,11-heptadecadienoic acid: New antibiotics fromSporothrix flocculosa andSporothrix regulosa.J. Nat. Prod. 57:700–704.

    Article  PubMed  CAS  Google Scholar 

  • Choudhury, S. R., Traquair, J. A., andJarvis, W. R. 1995. New extracellular fatty acids in culture filtrates ofSporothrix flocculosa andS. rugulosa.Can. J. Chem. 73:84–87.

    CAS  Google Scholar 

  • Conley, A. J., andKabara, J. J. 1973. Antimicrobial action of esters of polyhydric alcohols.Antimicrob. Agents Chemother. 4:501–506.

    PubMed  CAS  Google Scholar 

  • Frans, J. E., Knowles, W. S., andOsuch, C. 1965. Ozonolysis of cyclic olefins.J. Org. Chem. 30:4328–4330.

    Google Scholar 

  • Fravel, D. R. 1988. Role of antibiosis in the biocontrol of plant diseases.Annu. Rev. Phytopathol. 26:75–91.

    CAS  Google Scholar 

  • Hajlaoui, M. R., andBélanger, R. R. 1991. Comparative effects of temperature and humidity on the activity of three potential antagonists of rose powdery mildew.Neth. J. Plant Pathol. 97:203–208.

    Article  Google Scholar 

  • Hajlaoui, M. R., andBélanger, R. R. 1993. Antagonism of the yeast-like phylloplane fungusSporothrix flocculosa againstErysiphe graminis vartritici.Biocont. Sci. Technol. 3:427–434.

    Google Scholar 

  • Hajlaoui, M. R., Benhamou, N., andBélanger, R. R. 1992. Cytochemical study of the antagonistic activity ofSporothrix flocculosa on rose powdery mildew,Sphaerotheca pannosa var.rosae.Phytopathology 82:583–589.

    Google Scholar 

  • Hajlaoui, M. R., Traquair, J. A., Jarvis, W. R., andBélanger, R. R. 1994. Antifungal activity of extracellular metabolites produced bySporothrix flocculosa.Biocont. Sci. Technol. 4:229–237.

    Article  Google Scholar 

  • Homans, A. L., andFuchs, A. 1970. Direct bioautography on thin layer chromatograms as a method for detecting fungitoxic substances.J. Chromatogr. 51:327–329.

    Article  PubMed  CAS  Google Scholar 

  • Ikawa, M., Hartshorne, T., Caron, L., Iannitelli, R. C., Barbero, L. J., andWegener, K. 1984. Inhibition of growth of the green algaChlorella pyrenoidosa by unsaturated fatty acids.J. Am. Oil. Chem. Soc. 12:1877–1878.

    Google Scholar 

  • Jarvis, W. R., Shaw, L. A., andTraquair, J. A. 1989. Factors affecting antagonism of cucumber powdery mildew byStephanoascus flocculosus andS. rugulosus.Mycol. Res. 92:162–165.

    Article  Google Scholar 

  • Kabara, J. J. 1987. Fatty acids and esters as antimicrobial/insecticidal agents, pp. 220–238,in G. F. Fuller and W. D. Nes (eds.). Ecology and Metabolism of Plant Lipids. American Chemical Society, Washington, D.C.

    Google Scholar 

  • Kabara, J. J., Swieczkowski, D. M., Conley, A. J., andTruant, J. P. 1972. Fatty acids and derivatives as antimicrobial agents.Antimicrob. Agents Chemother. 2:23–28.

    PubMed  CAS  Google Scholar 

  • Kabara, J. J., Vrable, R., andLie Ken Jie, M. S. F. 1977. Antimicrobial lipids: natural and synthetic fatty acids and monoglycerides.Lipids 12:753–759.

    PubMed  CAS  Google Scholar 

  • Ko, Y., Frost, D., Ho, C., Ludescher, R., andWasserman, B. 1994. Inhibition of yeast (1,3)-beta-glucan synthase by phospholipase A2 and its reaction-products.Biochim. Biophys. Acta 1193:31–40.

    PubMed  CAS  Google Scholar 

  • Nieman, C. 1954. Influence of trace amounts of fatty acids on the growth of microorganisms.Bacteriol. Rev. 18:147–163.

    PubMed  CAS  Google Scholar 

  • Traquair, J. A., Shaw, L. A., andJarvis, W. R. 1988. New species ofStephanoascus withSporothrix anamorphs.Can. J. Bot. 66:926–933.

    Google Scholar 

  • Watson, K., andRose, A. 1980. Fatty-acyl composition of the lipids ofSaccharomyces cerevisiae grown aerobically and anaerobically in media containing different fatty acids.J. Gen. Microbiol. 117:225–233.

    CAS  Google Scholar 

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Contribution no. 150 du Centre de recherche en horticulture.

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Benyagoub, M., Bel Rhlid, R. & Bélanger, R.R. Purification and characterization of new fatty acids with antibiotic activity produced bySporothrix flocculosa . J Chem Ecol 22, 405–413 (1996). https://doi.org/10.1007/BF02033644

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