Characterization of Peptaibols Produced by a Marine Strain of the Fungus Trichoderma endophyticum via Mass Spectrometry, Genome Mining and Phylogeny-Based Prediction
Abstract
:1. Introduction
2. Materials and Methods
2.1. Collection and Fungal Acquisition
2.2. Fungal Identification
2.3. Phylogenetic Analyses
2.4. Fungal Fermentation and Extraction
2.5. Genome Mining and Prediction of the Peptaibol Modular Assembly
2.6. LC-MS/MS Analysis
2.7. Molecular Networking
3. Results
3.1. Fungal Phylogenetic Identificatio
3.2. Genome Mining
3.3. Analysis of 14-Module NRPS and Prediction of Peptaibol Assembly
3.4. Analysis of 15-Module NRPS and Prediction of Peptaibol Assembly
3.5. Annotation of the Peptaibols
4. Discussion
5. Conclusions
Supplementary Materials
Author Contributions
Funding
Data Availability Statement
Conflicts of Interest
References
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Ac-Aib-Ala-Aib-Ala-AA1-Gln-AA2-AA3-Aib-Ala-Aib-Aib-AA4-AA5-AA6ol | |||||||||
---|---|---|---|---|---|---|---|---|---|
Peptaibols | Compound a | Exp. m/z Δm/z (in ppm) | Chemical Formula | AA1 | AA2 | AA3 | AA4 | AA5 | AA6 |
Endophytins Series A | |||||||||
Endophytin A1 | 1 | 1394.8370 (−0.07) | C63H111N17O18 | Ala | Aib | Lxx | Ala | Gln | Lxxol |
Endophytin A2 | 2 | 1394.8322 (−3.51) | C63H111N17O18 | Aib | Aib | Vxx | Ala | Gln | Lxxol |
Endophytin A3 | 5 | 1408.8505 (1.56) | C64H113N17O18 | Aib | Aib | Vxx | Aib | Gln | Lxxol |
Endophytin A4 | 7 | 1408.8424 (1.06) | C64H113N17O18 | Aib | Vxx | Vxx | Ala | Gln | Lxxol |
Endophytin A5 | 8 | 1422.8657 (1.89) | C65H115N17O18 | Aib | Aib | Lxx | Aib | Gln | Lxxol |
Endophytin A6 | 12 | 1422.8665 (1.56) | C64H112N16O19 | Vxx | Aib | Vxx | Ala | Gln | Lxxol |
Endophytin | 11 | 1409.8345 (1.33) | C65H115N17O18 | Aib | Aib | Vxx | Aib | Glu | Lxxol |
Endophytin A8 | 14 | 1436.8805 (2.43) | C66H117N17O18 | Aib | Vxx | Lxx | Aib | Gln | Lxxol |
Endophytin A9 | 22 | 1436.8827 (8.28) | C65H114N16O19 | Vxx | Vxx | Lxx | Ala | Gln | Lxxol |
Endophytin A10 | 15 | 1423.8642 (0.07) | C65H114N16O19 | Vxx | Vxx | Vxx | Ala | Glu | Lxxol |
Endophytin A11 | 19 | 1423.8525 (0.90) | C66H117N17O18 | Aib | Vxx | Vxx | Aib | Glu | Lxxol |
Endophytin A12 | 23 | 1450.8867 (−1.51) | C67H119N17O18 | Vxx | Vxx | Lxx | Aib | Gln | Lxxol |
Endophytin A13 | 24 | 1437.8672 (0.55) | C66H116N16O19 | Vxx | Aib | Lxx | Aib | Glu | Lxxol |
Endophytins series B | |||||||||
Endophytin B1 | 25 | 1484.8862 (1.48) | C70H117N17O18 | Vxx | Vxx | Lxx | Aib | Gln | Pheol |
Endophytin B2 | 26 | 1471.8369 (3.05) | C69H114N16O19 | Vxx | Aib | Lxx | Aib | Glu | Pheol |
Endophytin B3 | 6 | 1442.8390 (6.72) | C67H111N17O18 | Aib | Aib | Vxx | Aib | Gln | Pheol |
Endophytin B4 | 10 | 1456.8501 (1.78) | C68H113N17O18 | Aib | Aib | Lxx | Aib | Gln | Pheol |
Endophytin B5 | 18 | 1456.8505 (2.37) | C69H115N17O18 | Vxx | Vxx | Vxx | Ala | Gln | Pheol |
Endophytin B6 | 17 | 1470.8676 (−1.51) | C68H113N17O18 | Aib | Vxx | Vxx | Aib | Gln | Pheol |
Endophytin B7 | 20 | 1470.8673 (0.74) | C69H115N17O18 | Vxx | Vxx | Vxx | Aib | Gln | Pheol |
Endophytin B8 | 27 | 1485.8639 (−2.75) | C70H116N16O19 | Vxx | Vxx | Lxx | Aib | Glu | Pheol |
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Castro, G.S.; Sousa, T.F.; da Silva, G.F.; Pedroso, R.C.N.; Menezes, K.S.; Soares, M.A.; Dias, G.M.; Santos, A.O.; Yamagishi, M.E.B.; Faria, J.V.; et al. Characterization of Peptaibols Produced by a Marine Strain of the Fungus Trichoderma endophyticum via Mass Spectrometry, Genome Mining and Phylogeny-Based Prediction. Metabolites 2023, 13, 221. https://doi.org/10.3390/metabo13020221
Castro GS, Sousa TF, da Silva GF, Pedroso RCN, Menezes KS, Soares MA, Dias GM, Santos AO, Yamagishi MEB, Faria JV, et al. Characterization of Peptaibols Produced by a Marine Strain of the Fungus Trichoderma endophyticum via Mass Spectrometry, Genome Mining and Phylogeny-Based Prediction. Metabolites. 2023; 13(2):221. https://doi.org/10.3390/metabo13020221
Chicago/Turabian StyleCastro, Gleucinei S., Thiago F. Sousa, Gilvan F. da Silva, Rita C. N. Pedroso, Kelly S. Menezes, Marcos A. Soares, Gustavo M. Dias, Aline O. Santos, Michel E. B. Yamagishi, Jéssica V. Faria, and et al. 2023. "Characterization of Peptaibols Produced by a Marine Strain of the Fungus Trichoderma endophyticum via Mass Spectrometry, Genome Mining and Phylogeny-Based Prediction" Metabolites 13, no. 2: 221. https://doi.org/10.3390/metabo13020221