Abstract
Pseudomonas aureofaciens (= P. chlororaphis) strain 63-28 is a biocontrol agent active against many soil-borne fungal plant pathogens and shows antifungal activity in culture assays. 3-(1-Hexenyl)-5-methyl-2-(5H)furanone was isolated from culture filtrates of this bacterium. The purified furanone showed antifungal activity against Pythium ultimum, Fusarium solani, Fusarium oxysporum, and Thielaviopsis basicola. The ED50S for spore germination of these fungi were 45, 54, 56, and 25 μg/ml, respectively. The compound also inhibited the germ tube growth of Rhizoctonia solani growing from microsclerotia, with an ED50 of 61 μg/ml. The compound is the reduced form of furanones previously described from this bacterium: 3-(1-hexenyl)-5-hydroxy-5-methyl-2-(5H)-furanone and 3-(1-hexenyl)-5-hydroxymethyl-2-(5H)-furanone. This volatile antifungal furanone has structural similarity to other antifungal furanones produced by actinomycetes (Streptomyces spp.), fungi (Trichoderma harzianum), and higher plants (Pulsatilla and Ranuculus spp.). This is the first report of 3-(1-hexenyl)-5-methyl-2-(5H)-furanone produced by a bacterium.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
REFERENCES
Almassi, F., Ghisalberti, E. L., and Narbey, M. 1991. New antibiotics from strains of Trichoderma harzianum. J. Nat. Prod. 54:396–402.
Benhamou, N., BÉlanger, R. R., and Paulitz, T. C. 1996. Pre-inoculation of Ri T-DNA-transformed pea roots with Pseudomonas fluorescens inhibits colonization by Pythium ultimum Trow: An ultrastructural and cytochemical study. Planta 199:105–117.
Braun, D., Pauli, N., SÉquin, U., and ZÅhner, H. 1995. New butenolides from the photoconductivity screening of Streptomyces antibioticus (Waksman and Woodruff) Waksman and Henrici 1948. FEMS Microbiol. Lett. 126:37–42.
Christie, W. W. 1982. Lipid Analysis. Isolation, Separation, Identification and Structural Analysis of Lipids, 2nd ed. Pergamon Press, Oxford, p. 79.
Chun, W., Cui, J., and Poplawsky, A. 1997. Purification, characterization and biological role of a pheromone produced by Xanthomonas campestris pv. campestris. Physiol. Mol. Plant Pathol. 51:1–14.
Dal Pozzo, A., Dansi, A., Mariotti, V., and Meneghini, E. 1972. Boll. Chim. Farm. 111:342–352.
Els, H., Sobin, B. A., and Celmer, W. D. 1958. PA-147 (3-carboxy-4-pentadienal lactol)—a new antibiotic. J. Am. Chem. Soc. 80:878–880.
GagnÉ, S., Dehbi, L., Le quÉrÉ, D., Cayer, F., Morin, J.-L., Lemay, R., and Fournier, N. 1993. Increase of greenhouse tomato fruit yields by plant growth-promoting rhizobacteria (PGPR) inoculated into the peat-based growth media. Soil Biol. Biochem. 25:269–273.
Gamard, P., Bel-Rhlid, R., LabbÉ, C., BÉlanger, R., and Paulitz, T. 1996. Production of multiple antifungal compounds by PGPR strains of Pseudomonas fluorescens and Serratia plymuthica. Can. J. Plant Pathol. 18:89.
Gamard, P., Sauriol, F., Benhamou, N., BÉlanger, R. R., and Paulitz, T. C. 1997. Novel butyrolactones with antifungal activity produced by Pseudomonas aureofaciens strain 63–28. J. Antibiot. 50:742–749.
Hill, D. J., and Peng, G. 1999. Evaluation of AtEze for suppression of fusarium wilt of chrysanthemum. Can. J. Plant Pathol. 21:194–195.
Hisao, Y. 1966. Antimicrobial activity of crotonic acid. I. Influence of crotonic acid on the growth of molds. Hakko Kogaku Zasshi 44:210–215.
Horinouchi, S., and Beppu, T. 1994. A factor as a microbial hormone that controls cellular differentiation and secondary metabolism in Streptomyces griseus. Mol. Microbiol. 12:859–864.
Howell, C. R., and Stipanovic, R. D. 1980. Suppression of Pythium ultimum-induced damping-off of cotton seedlings by Pseudomonas fluorescens and its antibiotic, pyoluteorin. Phytopathology 70:712–715.
Kelemen, G. H., and Buttner, M. J. 1998. Initiation of aerial mycelium formation in Streptomyces. Curr. Opin. Microbiol. 1:656–662.
King, E. O., Ward, M. K., and Raney, D. E. 1954. Two simple media for the demonstration of pyocyanin and fluorescin. J. Lab. Clin. Med. 44:301–307.
Lifshitz, R., Windham, M. T., and Baker, R. 1986. Mechanism of biological control of preemergence damping-off of pea by seed treatment with Trichoderma spp. Phytopathology 76:720–725.
Lorenzen, K., Anke, T., Konetschny-Rapp, S., and Scheuer, W. 1995. 5-Hydroxy-3-vinyl-2(5H)-furanone—a new inhibitor of human synovial phospholipase A2 and platelet aggregation from fermentations of a Calyptella species (Basidiomycetes). Z. Naturforsch. 50:403–409.
Lorimer, S. D., Mawson, S. D., Perry, N. B., and Weavers, R. T. 1995. Isolation and synthesis of β-miroside, and antifungal furanone glucoside from Prumnopitys ferruginea. Tetrahedron 51:7287–7300.
Mares, D. 1987. Antimicrobial activity of protoanemonin, a lactone from ranunculaceous plants. Mycopathologia 98:133–140.
Mares, D. 1989. Electron microscopy of Microsporum cookei after “in vitro” treatment with protoanemonin: A combined SEM and TEM study. Mycopathologia 108:37–46.
Mares, D., and Fasulo, M. P. 1990. Ultrastructural alterations in Epidermophyton floccosum and Trichophyton mentagrophytes exposed in vitro to protoanemonin. Cytobios 61:89–95.
Martin, M. L., San Roman, L., and Dominguez, A. 1990. In vitro activity of protoanemonin, and antifungal agent. Planta Med. 56:66–69.
Maurhofer, M., Keel, C., Schnider, U., Voisard, C., Hass, D., and DÉfago, G. 1992. Influence of enhanced antibiotic production in Pseudomonas fluorescens strain CHAO on its disease suppressive capacity. Phytopathology 82:190–195.
McCullagh, M., Utkhede, R., Menzies, J., Punja, Z., and Paulitz, T. C. 1996. Evaluation of plant growth-promoting rhizobacteria for biological control of Pythium root rot of cucumbers grown in rockwool and effects on yield. Eur. J. Plant Pathol. 102:747–755.
Misra, S. B., and Dixit, S. N. 1980. Antifungal principle of Ranunculus sceleratus. Econ. Bot. 34:362–367.
Ordentlich, A., Wiesman, Z., Gottlieb, H. E., Cojocaru, M., and Chet, I. 1992. Inhibitory furanone produced by the biocontrol agent Trichoderma harzianum. Phytochemistry 31:485–486.
Pfender, W. F., Kraus, J., and Loper, J. E. 1993. A genomic region form Pseudomonas fluorescens Pf-5 required for pyrrolnitrin production and inhibition of Pyrenophora tritici-repentis in wheat straw. Phytopathology 83:1223–1228.
Pierson, L. S., Wood, D. W., and Pierson, E. A. 1998. Homoserine lactone-mediated gene regulation in plant-associated bacteria. Annu. Rev. Phytopathol. 36:207–225.
Rezanka, T., LÍbalovÁ, D., Votruba, J., and VÍden, I. 1994. Identification of odorous compounds from Streptomyces avermitilis. Biotechnol. Lett. 16:75–78.
Sakurai, K., Matsumoto, H. and Adachi, J. 1968. Antifungal studies on drugs. I. Antifungal activity of five-membered lactone derivatives. Yakugaku Zasshi 88:919–924.
Seresinhe, N., Reyes, A. A., and Brown, G. L. 1997. Suppression of rhizoctonia stem rot on poinsettias with Pseudomonas aureofaciens, strain 63–28. Can. J. Phytopathol. 19:116.
Seto, H., Watanabe, H., and Furihata, K. 1996. Simultaneous operation of the mevalonate and non-mevalonate pathways in the biosynthesis of isopentenyl diphosphate in Streptomyces aeriouvifer. Tetrahedron Lett. 37:7979–7982.
Thomashow, L. S., and Weller, D. M. 1988. Role of a phenazine antibiotic from Pseudomonas fluorescens in biological control of Gaeumannomyces graminis var. tritici. J. Bacteriol. 170:3499–3508.
Thomashow, L. S., and Weller, D. M. 1996. Current concepts in the use of introduced bacteria for biological disease control: Mechanisms and antifungal metabolites, pp. 187–235, in G. Stacey and N. T. Keen (ed.). Plant-Microbe Interactions, Vol. 1. Chapman & Hall, New York.
Van Bruggen, A. H. C., and Arneson, P. A. 1986. Quantitative recovery of Rhizoctonia solani from soil. Plant Dis. 70:320–323.
Wu, G., Wu, Y., Zhang, C., Wang, Z., and Zhang, G. 1995. Control of wheat scab with an alkyl derivative of γ-methylene-γ-butyrolactone. Zhongguo Kexue Jishu Daxue Xuebao 25:382–386.
Yamada, Y., Sugamura, K., Kondo, K., Yanagimoto, M., and Okada, H. 1987. The structure of inducing factors of virginiamycin production in Streptomyces virginiae. J. Antibiot. 40:496–504.
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Paulitz, T., Nowak-Thompson, B., Gamard, P. et al. A Novel Antifungal Furanone from Pseudomonas aureofaciens, a Biocontrol Agent of Fungal Plant Pathogens. J Chem Ecol 26, 1515–1524 (2000). https://doi.org/10.1023/A:1005595927521
Issue Date:
DOI: https://doi.org/10.1023/A:1005595927521