View More View Less
  • 1 Bu Ali Sina University, Hamedan, Iran
  • | 2 University of Szeged, Szeged, Hungary
Restricted access

Five Iranian Trichoderma isolates from species T. viride, T. viridescens, T. asperellum, T. longibrachiatum and T. citrinoviride — selected from the Fungal Collection of the Bu Ali Sina University, Hamedan, Iran — were investigated for their peptaibol production. All examined isolates showed remarkable antibacterial activities during the screening of their extracts for peptaibol content with a Micrococcus luteus test culture. HPLC-ESI-IT MS was used for identification and elucidation of the amino acid sequences of peptaibols. The detected peptaibol compounds contain 20 or 18 amino acid residues and belong to the trichobrachin and trichotoxin groups of peptaibols, respectively. T. longibrachiatum and T. citrinoviride produced trichobrachins, while trichotoxins could be detected in T. viride, T. viridescens and T. asperellum. Out of 37 sequences detetermined, 26 proved to be new, yet undescribed compounds, while others were identified as previously reported trichotoxins (trichotoxin A-50s and T5D2) and trichobrachins (longibrachins AI, AII, AIII, BII and BIII). Compounds within the two groups of detected peptaibols differed from each other only by a single or just a few amino acid changes.

  • 1.

    Biemann, K. (1990) Sequencing of peptides by tandem mass spectrometry and high-energy collisioninduced dissociation. Methods Enzymol. 193, 455479.

    • Search Google Scholar
    • Export Citation
  • 2.

    Boheim, G., Irmscher, G., Jung, G. (1978) Trichotoxin A-40, a new membrane-exciting peptide. Part B. Voltage-dependent pore formation in bilayer lipid membranes and comparison with other alamethicin analogues. Biochim. Biophys. Acta –Biomem. 507, 485506.

    • Search Google Scholar
    • Export Citation
  • 3.

    Brito, J. P., Ramada, M. H., De Magalhães, M. T., Silva, L. P., Ulhoa, C. J. (2014) Peptaibols from Trichoderma asperellum TR356 strain isolated from Brazilian soil. SpringerPlus 3, 600.

    • Search Google Scholar
    • Export Citation
  • 4.

    Brückner, H., König, W. A., Aydin, M, J. G. (1985) Trichotoxin A40. Purification by counter-current distribution and sequencing of isolated fragments. Biochim. Biophys. Acta 827, 5162.

    • Search Google Scholar
    • Export Citation
  • 5.

    Brückner, H., Przybylski, M. (1984) Isolation and structural characterization of polypeptide antibiotics of the peptaibol class by high-performance liquid chromatography with field desorption and fast atom bombardment mass spectrometry. J. Chromatogr. 296, 263275.

    • Search Google Scholar
    • Export Citation
  • 6.

    Chiang, Y. M., Lee, K. H., Sanchez, J. F., Keller, N. P., Wang, C. C. (2009) Unlocking fungal cryptic natural products. Nat. Prod. Commun. 4, 15051510.

    • Search Google Scholar
    • Export Citation
  • 7.

    Chugh, J. K., Wallace, B. A. (2001) Peptaibols: models for ion channels. Biochem. Soc. Trans. 29, 565.

  • 8.

    Chutrakul, C., Alcocer, M., Bailey, K., Peberdy, J. F. (2008) The production and characterisation of trichotoxin peptaibols, by Trichoderma asperellum. Chem. Biodivers. 5, 16941706.

    • Search Google Scholar
    • Export Citation
  • 9.

    Degenkolb, T., Brückner, H. (2008) Peptaibiomics: towards a myriad of bioactive peptides containing C(alpha)-dialkylamino acids? Chem. Biodivers. 5, 18171843.

    • Search Google Scholar
    • Export Citation
  • 10.

    Grodnitskaya, I. D., Sorokin, N. D. (2006) Use of micromycetes Trichoderma for soil bioremediation in tree nurseries. Biol. Bull. 33, 400403.

    • Search Google Scholar
    • Export Citation
  • 11.

    Ha, T. (2010) Using Trichoderma species for biological control of plant pathogens in Vietnam. ISSAAS J. 16, 1721.

  • 12.

    Harman, G. E., Howell, C. R., Viterbo, A., Chet, I., Lorito, M. (2004) Trichoderma species –opportunistic, avirulent plant symbionts. Nat. Rev. Microbiol. 2, 4356.

    • Search Google Scholar
    • Export Citation
  • 13.

    Hatvani, L., Manczinger, L., Vágvölgyi, C., Kredics, L. (2013) Trichoderma as a human pathogen. In: Mukherjee, P. K., Horwitz, B. A., Singh, U. S., Mukherjee, M., Schmoll, M. (eds) Trichoderma –Biology and Applications. CAB International, Wallingford, UK. pp. 292313.

    • Search Google Scholar
    • Export Citation
  • 14.

    Hou, C. T., Ciegler, A., Hesseltine, C. W. (1972) New mycotoxin, trichotoxin A, from Trichoderma viride isolated from southern leaf blight-infected corn. Appl. Microbiol. 23, 183185.

    • Search Google Scholar
    • Export Citation
  • 15.

    Kredics, L., Antal, Z., Manczinger, L., Nagy, E. (2001) Breeding of mycoparasitic Trichoderma strains for heavy metal resistance. Lett. Appl. Microbiol. 33, 112116.

    • Search Google Scholar
    • Export Citation
  • 16.

    Kredics, L., García Jimenez, L., Naeimi, S., Czifra, D., Urbán, P., Manczinger, L., Vágvölgyi, C., Hatvani, L. (2010) A challenge to mushroom growers: the green mould disease of cultivated champignons. In: Méndez-Vilas, A. (ed.) Current Research, Technology and Education Topics in Applied Microbiology and Microbial Biotechnology. Formatex Research Center, Badajoz, Spain. pp. 295305.

    • Search Google Scholar
    • Export Citation
  • 17.

    Kredics, L., Hatvani, L., Naeimi, S., Körmöczi, P., Manczinger, L., Vágvölgyi, C., Druzhinina, I. (2014) Biodiversity of the genus Hypocrea/Trichoderma in different habitats. In: Gupta, V. K., Schmoll, M., Herrera-Estrella, A., Upadhyay, R. S., Druzhinina, I., Tuohy, M. (eds) Biotechnology and Biology of Trichoderma. Elsevier Science B. V., Amsterdam, The Netherlands. pp. 324.

    • Search Google Scholar
    • Export Citation
  • 18.

    Kubicek, C. P., Komon-Zelazowska, M., Sándor, E., Druzhinina, I. S. (2007) Facts and challenges in the understanding of the biosynthesis of peptaibols by Trichoderma. Chem. Biodivers. 4, 10681082.

    • Search Google Scholar
    • Export Citation
  • 19.

    Leclerc, G., Goulard, C., Prigent, Y., Bodo, B., Wróblewski, H., Rebuffat, S. (2001) Sequences and antimycoplasmic properties of longibrachins LGB II and LGB III, two novel 20-residue peptaibols from Trichoderma longibrachiatum. J. Nat. Prod. 64, 164170.

    • Search Google Scholar
    • Export Citation
  • 20.

    Leitgeb, B., Szekeres, A., Manczinger, L., Vágvölgyi, C., Kredics, L. (2007) The history of alamethicin: a review of the most extensively studied peptaibol. Chem. Biodivers. 4, 10271051.

    • Search Google Scholar
    • Export Citation
  • 21.

    Lorito, M., Woo, S. L., Garcia, I., Colucci, G., Harman, G. E., Pintor-Toro, J. A., Scala, F. (1998) Genes from mycoparasitic fungi as a source for improving plant resistance to fungal pathogens. Proc. Natl Acad. Sci. USA 95, 78607865.

    • Search Google Scholar
    • Export Citation
  • 22.

    Marahiel, M. A., Stachelhaus T., Mootz, H. D. (1997) Modular peptide synthetases involved in nonribosomal peptide synthesis. Chem. Rev. 97, 26512674.

    • Search Google Scholar
    • Export Citation
  • 23.

    Marik, T., Szekeres, A., Druzhinina, I. S., Andersson, M. A., Salkinoja-Salonen, M., Tyagi, C., Leitgeb, B., Vágvölgyi, C., Kredics, L. (2016) Bioactive peptaibols of forest-derived Trichoderma isolates from section Longibrachiatum. In: Lukac, M., Grenni, P., Gamboni, M. (eds) Soil Biological Communities and Ecosystem Resilience, “Sustainability in Plant and Crop Protection”, Springer Int. Publ. AG, Cham (WWW), Switzerland (in press).

    • Search Google Scholar
    • Export Citation
  • 24.

    Marik, T., Szekeres, A., Várszegi, C., Czifra, D., Vágvölgyi, C., Kredics, L. (2013) Rapid bioactivitybased pre-screening method for the detection of peptaibiotic-producing Trichoderma strains. Acta Biol. Szeged 57, 17.

    • Search Google Scholar
    • Export Citation
  • 25.

    Marik, T., Várszegi, C., Kredics, L., Vágvölgyi, C., Szekeres, A. (2013) Mass spectrometric investigation of alamethicin. Acta Biol. Szeged. 57, 109112.

    • Search Google Scholar
    • Export Citation
  • 26.

    Meyer, C. E., Reusser, F. (1967) A polypeptide antibacterial agent isolated from Trichoderma viride. Experientia 23, 8586.

  • 27.

    Mikkola, R., Andersson, M. A., Kredics, L., Grigoriev, P. A., Sundell, N., Salkinoja-Salonen, M. S. (2012) 20-Residue and 11-residue peptaibols from the fungus Trichoderma longibrachiatum are synergistic in forming Na+/K+-permeable channels and adverse action towards mammalian cells. FEBS J. 279, 41724190.

    • Search Google Scholar
    • Export Citation
  • 28.

    Mohamed-Benkada, M., Montagu, M., Biard, J. F., Mondeguer, F., Verite, P., Dalgalarrondo, M., Bissett, J., Pouchus, Y. F. (2006) New short peptaibols from a marine Trichoderma strain. Rapid Commun. Mass Spectrom. 20, 11761180.

    • Search Google Scholar
    • Export Citation
  • 29.

    Mueller, P., Rudin, D. O. (1968) Action potentials induced in biomolecular lipid membranes. Nature 217, 713719.

  • 30.

    Mukherjee, P. K., Wiest, A., Ruiz, N., Keightley, A., Moran-Diez, M. E., McCluskey, K., Pouchus, Y. F., Kenerley, C. M. (2010) Two classes of new peptaibols are synthesized by a single non-ribosomal peptide synthetase of Trichoderma virens. J. Biol. Chem. 286, 45444554.

    • Search Google Scholar
    • Export Citation
  • 31.

    Nelson, E. B. (2004) Biological control of Oomycetes and fungal pathogens. In: Goodman, R. M. (ed.) Encyclopedia of Plant and Crop Science. Marcell Dekker Inc., New York, USA. pp. 137140.

    • Search Google Scholar
    • Export Citation
  • 32.

    Neumann, N. K. N., Stoppacher, N., Zeilinger, S., Degenkolb, T., Brückner, H., Schuhmacher, R. (2015) The peptaibiotics database –a comprehensive online resource. Chem. Biodivers. 12, 743751.

    • Search Google Scholar
    • Export Citation
  • 33.

    Payne, J. W., Jakes, R., Hartley, B. S. (1970) The primary structure of alamethicin. Biochem. J. 117, 757766.

  • 34.

    Pócsfalvi, G., Ritieni, A., Ferranti, P., Randazzo, G., Vékey, K., Malorni, A. (1997) Microheterogeneity characterization of a paracelsin mixture from Trichoderma reesei using high-energy collision-induced dissociation tandem mass spectrometry. Rapid Commun. Mass Spectrom. 11, 922930.

    • Search Google Scholar
    • Export Citation
  • 35.

    Roepstorff, P., Fohlman, J. (1984) Proposal for a common nomenclature for sequence ions in mass spectra of peptides. Biomed. Mass. Spectrom. 11, 601.

    • Search Google Scholar
    • Export Citation
  • 36.

    Ruiz, N., Petit, K., Vansteelandt, M., Kerzaon, I., Baudet, J., Amzil, Z., Biard, J.-F., Grovel, O., Pouchus, Y. F. (2010) Enhancement of domoic acid neurotoxicity on Diptera larvae bioassay by marine fungal metabolites. Toxicon 55, 805810.

    • Search Google Scholar
    • Export Citation
  • 37.

    Schmoll, M., Schuster, A. (2010) Biology and biotechnology of Trichoderma. Appl. Microbiol. Biotechnol. 87, 787799.

  • 38.

    Shakeri, J., Foster, H. (2007) Proteolytic activity and antibiotic production by Trichoderma harzianum in relation to pathogenicity to insects. Enzyme Microb. Technol. 40, 961968.

    • Search Google Scholar
    • Export Citation
  • 39.

    Stoppacher, N., Neumann, N. K., Burgstaller, L., Zeilinger, S., Degenkolb, T., Brückner, H., Schuhmacher, R. (2013) The comprehensive peptaibiotics database. Chem. Biodivers. 10, 734743.

    • Search Google Scholar
    • Export Citation
  • 40.

    Strieker, M., Tanovic, A., Marahiel, M. A. (2010) Nonribosomal peptide synthetases: structures and dynamics. Curr. Opin. Struct. Biol. 20, 234240.

    • Search Google Scholar
    • Export Citation
  • 41.

    Suwan, S., Isobe, M., Kanokmedhakul, S., Lourit, N., Kanokmedhakul, K., Soytong, K., Koga, K. (2000) Elucidation of high micro-heterogeneity of an acidic-neutral trichotoxin mixture from Trichoderma harzianum by electrospray ionization quadrupole time-of-flight mass spectrometry. J. Mass Spectrom. 35, 14381451.

    • Search Google Scholar
    • Export Citation
  • 42.

    Szabó, M., Csepregi, K., Gálber, M., Virányi, F., Fekete, C. (2012) Control plant-parasitic nematodes with Trichoderma species and nematode-trapping fungi: The role of chi18-5 and chi18-12 genes in nematode egg-parasitism. Biol. Control 63, 121128.

    • Search Google Scholar
    • Export Citation
  • 43.

    Szekeres, A., Leitgeb, B., Kredics, L., Antal, Z, Hatvani, L., Manczinger, L., Vágvölgyi, C. (2005) Peptaibols and related peptaibiotics of Trichoderma –a review. Acta Microbiol. Immunol. Hung. 52, 137168.

    • Search Google Scholar
    • Export Citation
  • 44.

    Verma, V. C., Gond, S. K., Kumar, A., Kharwar, R. N., Strobel, G. (2007) The endophytic mycoflora of bark, leaf, and stem tissues of Azadirachta indica A. Juss (neem) from Varanasi (India). Microb. Ecol. 54, 119125.

    • Search Google Scholar
    • Export Citation
  • 45.

    Vinale, F., Sivasithamparam, K. E. A. (2012) Trichoderma secondary metabolites that affect plant metabolism. Nat. Prod. Commun. 7, 15451550.

    • Search Google Scholar
    • Export Citation
  • 46.

    Vinale, F., Sivasithamparam, K., Ghisalberti, E. L., Woo, S. L., Nigro, M., Marra, R., Lombardi, N., Pascale, A., Ruocco, M., Lanzuise, S., Manganiello, G., Lorito, M. (2014) Trichoderma secondary metabolites active on plants and fungal pathogens. Open Mycol. J. 8, 127139.

    • Search Google Scholar
    • Export Citation
  • 47.

    Weindling, R. (1932) Trichoderma lignorum as a parasite of other soil fungi. Phytopathology 22, 837845.

  • 48.

    Whitmore, L., Chugh, J. K., Snook, C. F., Wallace, B. A. (2003) The peptaibol database: a sequence and structure resource. J. Pept. Sci. 9, 663665.

    • Search Google Scholar
    • Export Citation
  • 49.

    Whitmore, L., Wallace, B. A. (2004) The peptaibol database: a database for sequences and structures of naturally occurring peptaibols. Nucl. Acids Res. 32, D593D594.

    • Search Google Scholar
    • Export Citation
  • 50.

    Wiest, A., Grzegorski, D., Xu, B.-W., Goulard, C., Rebuffat, S., Ebbole, D. J., Bodo, B., Kenerley, C. (2002) Identification of peptaibols from Trichoderma virens and cloning of a peptaibol synthetase. J. Biol. Chem. 277, 2086220868.

    • Search Google Scholar
    • Export Citation

Editorial Board

    1. Csányi, Vilmos (Göd)
    1. Dudits, Dénes (Szeged)
    1. Falus, András (Budapest)
    1. Fischer, Ernő (Pécs)
    1. Gábriel, Róbert (Pécs)
    1. Gulya, Károly (Szeged)
    1. Gulyás, Balázs (Stockholm)
    1. Hajós, Ferenc (Budapest)
    1. Hámori, József (Budapest)
    1. Heszky, László (Gödöllő)
    1. Hideg, Éva (Szeged)
    1. E. Ito (Sanuki)
    1. Janda, Tibor (Martonvásár)
    1. Kavanaugh, Michael P. (Missoula)
    1. Kása, Péter (Szeged)
    1. Klein, Éva (Stockholm)
    1. Kovács, János (Budapest)
    1. Brigitte Mauch-Mani (Neuchâtel)
    1. Nässel, Dick R. (Stockholm)
    1. Nemcsók, János (Szeged)
    1. Péczely, Péter (Gödöllő)
    1. Roberts, D. F. (Newcastle-upon-Tyne)
    1. Sakharov, Dimitri A. (Moscow)
    1. Singh, Meharvan (Fort Worth)
    1. Sipiczky, Mátyás (Debrecen)
    1. Szeberényi, József (Pécs)
    1. Székely, György (Debrecen)
    1. Tari, Irma (Szeged)
    1. Vágvölgyi, Csaba (Szeged),
    1. L. Zaborszky (Newark)

 

Acta Biologica Hungarica
P.O. Box 35
H-8237 Tihany, Hungary
Phone: (36 87) 448 244 ext. 103
Fax: (36 87) 448 006
E-mail: elekes@tres.blki.hu

Indexing and Abstracting Services:

  • Biological Abstracts
  • BIOSIS Previews
  • CAB Abstracts
  • Chemical Abstracts
  • Current Contents: Agriculture
  • Biology and Environmental Sciences
  • Elsevier BIOBASE
  • Global Health
  • Index Medicus
  • Index Veterinarius
  • Medline
  • Referativnyi Zhurnal
  • Science Citation Index
  • Science Citation Index Expanded (SciSearch)
  • SCOPUS
  • The ISI Alerting Services
  • Zoological Abstracts

 

Acta Biologica Hungarica
Language English
Size  
Year of
Foundation
1950
Publication
Programme
changed title
Volumes
per Year
 
Issues
per Year
 
Founder Magyar Tudományos Akadémia
Founder's
Address
H-1051 Budapest, Hungary, Széchenyi István tér 9.
Publisher Akadémiai Kiadó
Publisher's
Address
H-1117 Budapest, Hungary 1516 Budapest, PO Box 245.
Responsible
Publisher
Chief Executive Officer, Akadémiai Kiadó
ISSN 0236-5383 (Print)
ISSN 1588-256X (Online)