Eight new and four known peptaibols were isolated from a strain of the fungus, Trichoderma atroviride (NF16), which was cultured from an Axinellid sponge collected from the East Mediterranean coast of Israel. The structures of the pure compounds were determined using HRMS, MS/MS and one- and two-dimensional NMR measurements. The isolated compounds belong to the trichorzianines, a family of 19-residue linear hydrophobic peptides containing a high proportion of α-aminoisobutyric acid (Aib), an acetylated N-terminus and a C-terminal amino alcohol. These new peptaibols exhibited antimicrobial activity against environmental bacteria isolated from the Mediterranean coast of Israel.
References
[1]
Chugh, K.J.; Wallace, B.A. Peptaibols: Models for ion channels. Biochem. Soc. Trans. 2001, 29, 565–570, doi:10.1042/BST0290565.
[2]
Schuhmacher, R.; Stoppacher, N.; Zeilinger, S. Peptaibols of Trichoderma atroviride: Screening, Identification, and Structure Elucidation by Liquid Chromatography-Tandem Mass Spectrometry. In Communicating Current Research and Education Topics and Trends in Applied Microbiology; Méndez-Vilas, A., Ed.; Formatex: Badajoz, Spain, 2007; pp. 609–617.
[3]
Kleinkauf, H.; Dohren, H. Nonribosomal biosynthesis of peptide antibiotics. Eur. J. Biochem. 1990, 192, 1–15.
[4]
Peptaibol Database. Available online: http://www.cryst.bbk.ac.uk/peptaibol (accessed on 14 May 2012).
[5]
Benitez, T.; Rincon, A.M.; Limon, M.C.; Codon, A.C. Biocontrol mechanisms of Trichoderma strains. Int. Microbiol. 2004, 7, 249–260.
[6]
Bodo, B.; Rebuffat, S.; El Hajii, M.; Davoust, D. Structure of Trichorzianine A IIIC, an antifungal peptide from Trichoderma harzianum. J. Am. Chem. Soc. 1985, 107, 6011–6017, doi:10.1021/ja00307a028.
[7]
El Hajii, M.; Rebuffat, S.; Lecommandeur, D.; Bodo, B. Isolation and sequence determination of trichorzianines A antifungal peptides from Trichoderma harzianum. Int. J. Peptide Prot. Res. 1987, 29, 207–215.
[8]
Rebuffat, S.; El Hajii, M.; Hennig, P.; Davoust, D.; Bodo, B. Isolation, sequence and conformation of seven trichorzianines B from Trichoderma harzianum. Int. J. Peptide. Prot. Res. 1989, 34, 200–210.
[9]
Pocsfalvi, G.; Scala, F.; Lorito, M.; Ritieni, A.; Randazzo, G.; Ferranti, P.; Vekey, K.; Malorni, A. Microheterogeneity characterization of a trichorzianine-A mixture from Trichoderma harzianum. J. Mass. Spectrom. 1998, 33, 154–163, doi:10.1002/(SICI)1096-9888(199802)33:2<154::AID-JMS620>3.0.CO;2-0.
[10]
Carroux, A.; van Bohemen, A.-I.; Roullier, C.; du Pont, T.R.; Vansteelandt, M.; Bondon, A.; Zalouk-Vergnoux, A.; Pouchus, Y.F.; Ruiz, N. Unprecedented 17-residue peptaibiotics produced by marine-derived Trichoderma atroviride. Chem. Biodivers. 2013, 10, 772–786, doi:10.1002/cbdv.201200398.
[11]
Oh, S.U.; Lee, S.J.; Kim, J.H.; Yoo, I.D. Structural elucidation of new antibiotic peptides, atroviridins A, B and C from Trichoderma atroviride. Tetrahedron Lett. 2000, 41, 61–64, doi:10.1016/S0040-4039(99)02000-6.
[12]
Oh, S.U.; Yun, B.S.; Lee, S.J.; Kim, J.H.; Yoo, I.D. Atroviridins A–C and neoatroviridins A–D, novel peptaibol antibiotics produced by Trichoderma atroviride F80317. I. Taxonomy, fermentation, isolation and biological activity. J. Antibiot. 2002, 55, 557–564, doi:10.7164/antibiotics.55.557.
[13]
Stoppacher, N.; Reithner, B.; Omann, M.; Zeilinger, S.; Krska, R.; Schuhmacher, R. Profiling of trichorzianines in culture samples of Trichoderma atroviride by liquid chromatography/tandem mass spectrometry. Rapid Commun. Mass Spectrom. 2007, 21, 3963–3970.
[14]
Sabareesh, V.; Balaram, P. Tandem electrospray mass spectrometric studies of proton and sodium ion adducts of neutral peptides with modified N- and C-termini: Synthetic model peptides and microheterogeneous peptaibol antibiotics. Rapid Commun. Mass Spectrom. 2006, 20, 618–628, doi:10.1002/rcm.2349.
[15]
Marfey, P. Determination of d-amino acids. II. Use of a bifunctional reagent, 1,5-fluoro-2,4-dinitrobenzene. Carlsberg Res. Commun. 1987, 49, 591–596, doi:10.1007/BF02908688.
[16]
Fujii, K.; Shimoya, T.; Ikai, Y.; Oka, H.; Harada, K. Further application of Advanced Marfey’s method for determination of absolute configuration of primary amino compound. Tetrahedron Lett. 1998, 39, 2579–2582, doi:10.1016/S0040-4039(98)00273-1.
[17]
Bowden, K.; Heilbron, I.M.; Jones, E.R.H.; Weedon, B.C.L. Researches on acetylenic compounds. Part I. The preparation of acetylenic ketones by oxidation of acetylenic carbinols and glycols. J. Chem. Soc. 1946, 39–45.
[18]
Gal-Hemed, I.; Atanasova, L.; Komon-Zelazowska, M.; Druzhinina, I.S.; Viterbo, A.; Yarden, O. Marine isolates of Trichoderma as potential halotolerant agents of biological control for arid-zone agriculture. Appl. Environ. Microbiol. 2011, 77, 5100–5109.
[19]
White, T.J.; Bruns, T.; Lee, S.; Taylor, J. Amplification and Direct Sequencing of Fungal Ribosomal RNA Genes for Phylogenetics. In PCR Protocol: A Guide to Methods and Applications; Innis, M.A., Gellfand, D.H., Sninisky, J.J., White, T.J., Eds.; Academic Press: New York, NY, USA, 1990; pp. 315–322.
[20]
Paz, Z.; Komon-Zelazowska, M.; Druzhinina, I.S.; Aveskamp, M.M.; Shnaiderman, A.; Aluma, Y.; Carmeli, S.; Ilan, M.; Yarden, O. Diversity and potential antifungal properties of fungi associated with a Mediterranean sponge. Fungal Divers. 2010, 42, 17–26, doi:10.1007/s13225-010-0020-x.
[21]
International Subcommission on Trichderma and Hypocrea Taxonomy.
[22]
National Center for Biotechnology Information.
[23]
Pitcher, D.J.; Saunders, N.A.; Owen, R.J. Rapid extraction of bacterial genomic DNA with guanidinium thiocyanate. Lett. Appl. Microbiol. 1989, 8, 151–156, doi:10.1111/j.1472-765X.1989.tb00262.x.
[24]
Oh, D.C.; Jensen, P.R.; Fenical, W. Zygosporamide, a cytotoxic cyclic depsipeptide from the marine-derived fungus Zygosporium masonii. Tetrahedron Lett. 2006, 47, 8625–8628, doi:10.1016/j.tetlet.2006.08.113.
