Abstract
Pseudomonas aeruginosa PGPR2 was found to protect mungbean plants from charcoal rot disease caused by Macrophomina phaseolina. Secondary metabolites from the culture supernatant of P. aeruginosa PGPR2 were extracted with ethyl acetate and the antifungal compound was purified by preparative HPLC using reverse phase chromatography. The purified compound showed antifungal activity against M. phaseolina and other phytopathogenic fungi (Fusarium sp., Rhizoctonia sp. Alternaria sp., and Aspergillus sp.). The structure of the purified compound was determined using 1H, 13C, 2D NMR spectra and liquid chromatography-mass spectrometry (LC-MS). Spectral data suggest that the antifungal compound is 3,4-dihydroxy-N-methyl-4-(4-oxochroman-2-yl)butanamide, with the chemical formula C14H17NO5 and a molecular mass of 279. Though chemically synthesized chromanone derivatives have been shown to have antifungal activity, we report for the first time, the microbial production of a chromanone derivative with antifungal activity. This ability of P. aeruginosa PGPR2 makes it a suitable strain for biocontrol.
Similar content being viewed by others
References
Howell, C. R., & Stipanovic, R. D. (1980). Phytopathology, 70, 712–715.
Bhattacharyya, P. N., & Jha, D. K. (2012). World Journal of Microbiology and Biotechnology, 28, 1327–1350.
Lee, J. Y., Moon, S. S., & Hwang, B. K. (2003). Applied Environmental Microbiology, 69, 2023–2021.
Sorensen, D., Nielsen, T. H., Christophersen, C., Sorensen, J., & Gajhede, M. (2001). Acta Crystallographica C, 57, 1123–1124.
Paulitz, T., Nowak-Thompson, B., Gamard, P., Tsang, E., & Loper, J. (2000). Journal of Chemical Ecology, 26, 1515–24.
Slininger, P. J., Burkhead, K. D., Schisler, D. A., & Bothast, R. J. (2000). Applied Microbiology and Biotechnology, 54, 376–381.
Kim, B. S., Lee, J. Y., & Hwang, B. K. (2000). Pest Management Science, 56, 1029–1035.
Gamard, P., Sauriol, F., Benhamou, N., Belanger, R. R., & Paulitz, T. C. (1997). Journal of Antibiotics, 50, 742–749.
Jiao, Y., Yoshihara, T., Ishikuri, S., Uchino, H., & Ichihara, A. (1996). Tetrahedron Letters, 37, 1039–1042.
Howie, W. J., & Suslow, T. V. (1991). Molecular Plant-Microbe Interactions, 4, 393–399.
Thomas, F. C., Chin-A-Woeng, Bloemberg, G. V., Mulders, H.M., Dekkers, L.C., & Lugtenberg, J.J. (2000). Molecular Plant-Microbe interactions, 13, 1340–1345.
Voisard, C., Keel, C., Haas, D., & Defago, G. (1989). EMBO Journal, 8, 351–358.
Garagulia, A. D., Kiprianova, E. A., & Boiko, O. I. (1974). MikrobioL Zh. (Kiev), 36, 197–202.
Siddiqui, Z. A., & Akhtar, M. S. (2007). Journal of Plant Pathology, 89, 67–77.
Laville, J., Blumer, C., Schroetter, C. V., Gaia, V., Défago, G., Keel, C., & Haas, D. (1998). The Journal of Bacteriology, 180, 3187–3196.
Nakkeeran, S., Kavitha, K., Chandrasekar, G., Renukadevi, P., & Fernando, W. G. D. (2006). Biocontrol Science and Technology, 16, 403–416.
Kavitha, K., Nakkeeran, S., Chandrasekar, G., Fernando, W. G. D., Mathiyazhagan, S., Renukadevi, P., & Krishnamoorthy, A. S. (2003). Proceedings of the 6th international workshop on PGPR (pp 493–497). Calicut: Organised by IISR.
Nakkeeran, S., Kavitha, K., Mathiyazhagan, S., Fernando, W. G. D., Chandrasekar, G., & Renukadevi, P. (2004). Canadian Journal of Plant Pathology, 26, 417–418.
Indera, K., Sing, T., Machado, C. C., & Sinclair, J. B. (1986). Phytopathology, 76, 532–535.
Illakkiam, D., Anuj, L.P., Ponraj, P., Shankar, M., Rajendhran, J.,& Gunasekaran, P. (2012). Indian journal of Experimental Biology (in press).
Ashoub, A. H., & Amara, M. T. (2009). Journal of American Science, 6, 321–328.
Hicks, R. E., Amann, R. I., & Stahl, D. A. (1992). Applied Environmental Microbiology, 58, 2158–2163.
White, T. J., Bruns, T., Lee, S., & Taylor, J. (1990). In PCR Protocols: a guide to methods and applications (pp. 315–322). Academic Press: San Diego, CA, USA.
Altschul, S. F., Gish, W., Miller, W., Myers, E. W., & Lipman, D. L. (1990). Molecular Biology, 215, 403–410.
Sadfi, N., Cherif, M., Fliss, I., Boudabous, A., & Antoun, H. (2001). Journal of Plant Pathology, 83, 101–118.
Akhtar, M. S., & Siddiqui, Z. A. (2009). Australasian Plant Pathology, 38, 44–50.
Lichtenthaler, H. K. (1987). Methods in Enzymology, 148, 350–382.
Raaijmakers, J. M., & Weller, D. M. (2001). Applied Environmental Microbiology, 67, 2545–2554.
Keel, C., Schnider, U., Maurhofer, M., Voisard, C., Burger, M., Wirthner, P., Haas, D., & Defago, G. (1992). Molecular Plant-Microbe Interactions, 5, 4–13.
Kavitha, K., Mathiyazhagan, S., Sendhilvel, V., Nakkeeran, S., Chandrasekar, G., & Fernando, W. G. D. (2005). Archives of Phytopathology and Plant Protection, 38, 69–76.
Ahmad, F., Ahmad, I., & Khan, M. S. (2008). Microbiological Research, 163, 173–181.
Buysens, S., Heungens, K., Poppe, J., & Hofte, M. (1996). Applied Environmental Microbiology, 62, 865–871.
Anjaiah, V., Cornelis, P., & Koedam, N. (2003). Candian Journal of Microbiology, 49, 85–91.
Bano, N., & Musarrat, J. (2003). Current Microbiology, 46, 324–328.
Kumar, R. S., Ayyadurai, N., Pandiaraja, P., Reddy, A. V., Venkateswarlu, Y., Prakash, O., & Sakthivel, N. (2005). Journal of Applied Microbiology, 98, 145–154.
Wu, D. Q., Ye, J., Ou, H. Y., Wei, X., Huang, X. Q., He, Y. W., & Xu, Y. Q. (2011). BMC Genomics, 12, 438–455.
Patel, C. M., Nilesh, N. G., & Rajani, D. P. (2011). Der Pharma Chemica, 3, 422–432.
Siddiqui, Z. N., & Farooq, F. (2012). Journal of Chemical Sciences, 124, 1097–1105.
Ayati, A., Falahati, M., Irannejad, H., & Saeed. (2012). DARU Journal of Pharmaceutical Sciences, 20, 46–53.
Acknowledgements
The work was financially supported by the Indian Council for Agricultural Research (NBAIM/AMAAS/2007-2012/MG (5)/PG/BG/3), India. The central facilities from CAS, CEGS, UGC-NRCBS and DBT- IPLS at MKU are gratefully acknowledged.
Author information
Authors and Affiliations
Corresponding author
Electronic supplementary material
Below is the link to the electronic supplementary material.
ESM 1
(DOC 960 kb)
Rights and permissions
About this article
Cite this article
Illakkiam, D., Ponraj, P., Shankar, M. et al. Identification and Structure Elucidation of a Novel Antifungal Compound Produced by Pseudomonas aeruginosa PGPR2 Against Macrophomina phaseolina . Appl Biochem Biotechnol 171, 2176–2185 (2013). https://doi.org/10.1007/s12010-013-0469-7
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s12010-013-0469-7