Characterization of volatile secondary metabolites from Trichoderma asperellum
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Abstract
Many Trichoderma isolates are known to secrete several secondary metabolites with different biological activities towards plants and other microbes. The production of such compounds varies according to the strain. In the present study, volatile secondary metabolites from the culture filtrate of Trichoderma asperellum strain were characterized using Gas chromatography-Mass spectrometry (GC-MS). Results of GC-MS detected 43 secondary metabolites in the T. asperellum strain including many important volatile secondary metabolites such as 1,2-Benzenedicarboxylic acid, 2-butoxy-2-oxoethyl butyl ester (peak area-3.59%), 1,2-Benzenedicarboxylic acid dibutyl ester (peak area-2.02 %), 2H-Pyran-2-one (peak area-66.63 %), palmitic acid (peak area-2.86 %), several phenolic isomers, methyl cyclohexane etc., all reportedly having effective pesticidal activity. The results indicated that these secondary metabolites could be useful for biological control applications of T. asperellum strain against diverse plant pathogens.
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Keywords
GC-MS, Metabolites, Trichoderma, Volatile
References
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Dubey, S.C., Tripathi, A., Dureja, P. and Grover, A. (2011). Characterization of secondary metabolites and enzymes produced by Trichoderma species and their efficacy against plant pathogenic fungi. Indian Journal of
Agricultural Research. 81(5): 455-461
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Korpi, A., Jarnberg, J. and Pasanen, A.L. (2009). Microbial volatile organic compounds; Critical Reviews in Toxicology, 39: 139–193
Leitgeb, B., Szekeres, A., Manczinger, L., Vagvolgyi, C. and Kredics, L. (2007). The history of alamethicin: a review of the most extensively studied peptaibol. Chem.
Biodivers. 4: 1027–1051
Osorio, E.J., Robledo, S.M., Bastida, J. (2008). Alkaloids with antiprotozoal activity. The Alkaloids, 66: 113- 190
Reino, J.L., Guerrero, R.F., Hernandez-Galan, R. and Collado, I.G. (2008) Secondary metabolites from species of the biocontrol agent Trichoderma. Phytochem. Rev., 2008; 7: 89-123
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Schnurer, J., Olsson, J. and Borjesson, T. (1999). Fungal volatiles as indicators of food and feeds spoilage. Fungal Genetics and Biology, 27: 209–217
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Siddiquee, S., Cheong, B.E., Taslima, K., Kausar, H. and Hasan, Md. M. (2012). Separation and identification of volatile compounds from liquid cultures of Trichoderma harzianum by GC-MS using three different capillary columns. Journal of Chromatographic Science, 50: 358-367
Singh, U.S., Zaidi, N.W., Joshi, D., Varshney, S. and Khan, T. (2006). Current status of Trichoderma as a biocontrol agent. In: Ramanujam B, Rabindra RJ (eds) Current status of biological control of plant diseases using antagonistic organisms in India, Project Directorate of Biological Control, Bangalore.
Sivasithamparam, K. and Ghisalberti, E.L. (1998). Trichoderma and Gliocladium. Kubicek, C.P. and Harman, G.E. (eds), Vol. 1. Taylor & Francis Ltd., London, Pp. 139–188
TajickGhanbari, M.A., Mohammaskhani, H.S. and Babaeizad, V. (2014). Identification of some secondary metabolites produced by four Penicillium species. MycologiaIranica, 1(2): 107-113
Tarus, P.K., Langat-Thoruwa, C.C., Wanyonyi, A.W. and Chhabra, S.C. (2003). Bioactive metabolites from Trichoderma harzianum and Trichoderma longibrachiatum. Bull. Chem. Soc. Ethiop., 17(2): 185-190
Tucci, M., Ruocco, M., De Masi, L., De Palma, M. &Lorito, M. (2011). The beneficial effect of Trichoderma spp. on tomato is modulated by the plant genotype. Mol. Plant. Pathol., 12: 341–354
Vey, A., Hoagland, R. E. and Butt, T.M. (2001). Toxic metabolites of fungal biocontrol agents. Fungi as Biocontrol Agents: Progress, Problems and Potential. Butt, T.M. and Jackson, C. (eds), Pp. 311-346. CAB International, Bristol.
Vinale, F., Sivasithamparam, K., Ghisalberti, E.L., Marra, R., Barbetti, M.J. and Li, H. (2008). A novel role for Trichoderma secondary metabolites in the interactions with plants. Physiological and Molecular Plant Pathology, 72: 80–86
Viterbo, A., Landau, U., Kim, S., Chernin, L. & Chet, I. (2010). Characterization of ACC deaminase from the biocontrol and plant growth-promoting agent Trichoderma asperellum T203. FEMS Microbiol. Lett., 305: 42–48
Viterbo, A., Wiest, A., Brotman, Y., Chet, I. and Kenerley, C. (2007). The 18mer peptaibols from Trichoderma virens elicit plant defence responses. Mol. Plant. Pathol., 8: 737–746
Claydon, N., Allan, M., Hanson, J.R. and Avent, A.G. (1987). Antifungal alkyl pyrones of Trichoderma
harzianum. Trans. Br. mycol. Soc., 88: 503–13
Cooney, J.M., Lauren, D.R. and Di Menna, M.E. (2001). Impact of competitive fungi on trichothecene production by Fusarium graminearum. Journal of Agricultural and Food Chemistry. 49: 522–526
Dubey, S.C., Tripathi, A., Dureja, P. and Grover, A. (2011). Characterization of secondary metabolites and enzymes produced by Trichoderma species and their efficacy against plant pathogenic fungi. Indian Journal of
Agricultural Research. 81(5): 455-461
Ghisalberti, E.L., Narbey, M.J., Dewan, M.M., Sivasithamparam, K. (1990). Variability among strains of Trichoderma harzianum in their ability to reduce take-all and to produce pyrones. Plant and Soil. 121: 287–291
Goulard, C., Hlimi, S.. Rebuffat, S. and Bodo, B. (1995). Trichorzins HA and MA antibiotic peptides from Trichoderma harzianum. I. Fermentation, isolation and biological properities. J. Antibiot.,48: 1248–53
Harman, G. E., Howell, C.R., Viterbo, A., Chet, I. and Lorito, M. (2004). Trichoderma species: opportunistic avirulant plant symbionts. Nature rev. microbiol., 2: 43-56
Harman, G.E. and Bjorkmann, T. (1998). Potential and existing uses of Trichoderma and Gliocladium for plant disease control and plant growth enhancement. Edited by G. E. Harman and C. P. Kubicek. London: Taylor and Francis. Trichoderma and Gliocladium, vol.2. Enzymes, biological control and commercial applications, Pp. 229–265
Hlimi, S., Rebuffat, S., Goulard, C., Duchamp, S., and Bodo, B. (1995). Trichorzins HA and MA, antibiotic peptides from Trichodermaharzianum. II. Sequence Determination. J. Antibiot., 48: 1254–61
Howell, C. R. (2006). Understanding the mechanisms employed by Trichoderma virens to effect biological control of cotton diseases. Phytopathology. 96: 178–180
Korpi, A., Jarnberg, J. and Pasanen, A.L. (2009). Microbial volatile organic compounds; Critical Reviews in Toxicology, 39: 139–193
Leitgeb, B., Szekeres, A., Manczinger, L., Vagvolgyi, C. and Kredics, L. (2007). The history of alamethicin: a review of the most extensively studied peptaibol. Chem.
Biodivers. 4: 1027–1051
Osorio, E.J., Robledo, S.M., Bastida, J. (2008). Alkaloids with antiprotozoal activity. The Alkaloids, 66: 113- 190
Reino, J.L., Guerrero, R.F., Hernandez-Galan, R. and Collado, I.G. (2008) Secondary metabolites from species of the biocontrol agent Trichoderma. Phytochem. Rev., 2008; 7: 89-123
Reithner, B., Brunner, K., Schuhmacher, R., Peissl, I., Seidl, V., Krska, R. and Zeilinger, S. (2005). The G protein a subunit Tga1 of Trichoderma atroviride is involved in chitinase formation and differential production of antifungal metabolites. Fungal Genet. Biol., 42: 749–760
Reithner, B., Schuhmacher, R., Stoppacher, N., Pucher, M., Brunner, K. and Zeilinger, S. (2007). Signaling via the Trichoderma atroviride mitogen-activated protein kinase Tmk 1 differentially affects mycoparasitism and plant protection. Fungal Genet. Biol., 44: 1123–1133
Scarselletti, R. and Faull, J. L. (1994). In Vitro activity of 6-pentyl-a-pyrone, a metabolite of Trichoderma harzianum, in the inhibition of RhizoctoniasolaniandFusarium oxysporumf. sp. lycopersici. Mycol. Res., 98:1207-09
Schnurer, J., Olsson, J. and Borjesson, T. (1999). Fungal volatiles as indicators of food and feeds spoilage. Fungal Genetics and Biology, 27: 209–217
Senthilkumar, G., Madhanraj, P. and Panneerselvam, A. (2011). Studies on the compounds and its antifungal potentiality of fungi isolated from paddy field soils of Jenbagapuram Village, Thanjavur District, and South India. Asian journal of pharmaceutical research. 1 (1): 19-21
Shoresh, M., Harman, G. E. and Mastouri, F. (2010). Induced systemic resistance and plant responses to fungal biocontrol agents. Annu. Rev. Phytopathol., 48: 21–43
Siddiquee, S., Cheong, B.E., Taslima, K., Kausar, H. and Hasan, Md. M. (2012). Separation and identification of volatile compounds from liquid cultures of Trichoderma harzianum by GC-MS using three different capillary columns. Journal of Chromatographic Science, 50: 358-367
Singh, U.S., Zaidi, N.W., Joshi, D., Varshney, S. and Khan, T. (2006). Current status of Trichoderma as a biocontrol agent. In: Ramanujam B, Rabindra RJ (eds) Current status of biological control of plant diseases using antagonistic organisms in India, Project Directorate of Biological Control, Bangalore.
Sivasithamparam, K. and Ghisalberti, E.L. (1998). Trichoderma and Gliocladium. Kubicek, C.P. and Harman, G.E. (eds), Vol. 1. Taylor & Francis Ltd., London, Pp. 139–188
TajickGhanbari, M.A., Mohammaskhani, H.S. and Babaeizad, V. (2014). Identification of some secondary metabolites produced by four Penicillium species. MycologiaIranica, 1(2): 107-113
Tarus, P.K., Langat-Thoruwa, C.C., Wanyonyi, A.W. and Chhabra, S.C. (2003). Bioactive metabolites from Trichoderma harzianum and Trichoderma longibrachiatum. Bull. Chem. Soc. Ethiop., 17(2): 185-190
Tucci, M., Ruocco, M., De Masi, L., De Palma, M. &Lorito, M. (2011). The beneficial effect of Trichoderma spp. on tomato is modulated by the plant genotype. Mol. Plant. Pathol., 12: 341–354
Vey, A., Hoagland, R. E. and Butt, T.M. (2001). Toxic metabolites of fungal biocontrol agents. Fungi as Biocontrol Agents: Progress, Problems and Potential. Butt, T.M. and Jackson, C. (eds), Pp. 311-346. CAB International, Bristol.
Vinale, F., Sivasithamparam, K., Ghisalberti, E.L., Marra, R., Barbetti, M.J. and Li, H. (2008). A novel role for Trichoderma secondary metabolites in the interactions with plants. Physiological and Molecular Plant Pathology, 72: 80–86
Viterbo, A., Landau, U., Kim, S., Chernin, L. & Chet, I. (2010). Characterization of ACC deaminase from the biocontrol and plant growth-promoting agent Trichoderma asperellum T203. FEMS Microbiol. Lett., 305: 42–48
Viterbo, A., Wiest, A., Brotman, Y., Chet, I. and Kenerley, C. (2007). The 18mer peptaibols from Trichoderma virens elicit plant defence responses. Mol. Plant. Pathol., 8: 737–746
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Characterization of volatile secondary metabolites from Trichoderma asperellum. (2017). Journal of Applied and Natural Science, 9(2), 954-959. https://doi.org/10.31018/jans.v9i2.1303
