Chemical study and investigation of the larvicidal activity of metabolites produced by the endophytic fungus Colletotrichum siamense
DOI:
https://doi.org/10.5902/2179460X86053Keywords:
Colletotrichum siamense, Molecular networking, CytochalasinAbstract
Microorganisms can produce a wide range of secondary metabolites with different activities, including larvicidal activities. Colletotrichum is a widespread fungal genus worldwide, and some species of this genus can establish mutualistic interactions with plants. In this study, the endophytic fungus Colletotrichum siamense was isolated from the hemiparasitic plant Passovia stelis to evaluate the chemical profile of the microorganism and its larvicidal activity against Aedes aegypti. This mosquito is one of the main transmitters of arboviruses, and the use of synthetic insecticides to fight the mosquito has generated resistance in its populations. For the larvicidal tests, the organic extract of fungal metabolites was obtained by partitioning with ethyl acetate after the cultivation of C. siamese in potato dextrose broth. The assay results indicated that the C. Siamese extract was active against Ae. aegypti, with an LC50 of 248 µg/mL for a 72-hour treatment. The extract was then subjected to chemical dereplication using the Global Natural Products Social Molecular Networking (GNPS) platform. The metabolites culmorin and cytochalasin D were found in the extract, the latter of which is representative of a biosynthetic class with previously reported activities against Aedes aegypti larvae.
Downloads
References
Araújo, I. F., Marinho, V. H. S., Sena, I. S., Curti, J. M., Ramos, R. S., Ferreira, R. M. A., Souto, R. N. P., & Ferreira, I. M. (2022). Larvicidal activity against Aedes aegypti and molecular docking studies of compounds extracted from the endophytic fungus Aspergillus sp. isolated from Bertholletia excelsa Humn. & Bonpl. Biotechnology Letters, 44, 439–459.
Aron, A. T., Gentry, E. C., McPhail, K. L., Nothias, L., Nothias Esposito, M., Bouslimani, A., Petras, D., Gauglitz, J. M., Sikora, N., Vargas, F., van der Hooft, J. J. J., Ernst, M., Kang, K. B., Aceves, C. M., Caraballo Rodríguez, A. M., Koester, I., Weldon, K. C., Bertrand, S., Roullier, C., Sun, K., Tehan, R. M., Boya P, C. A., Christian, M. H., Gutiérrez, M., Ulloa, A. M., Mora, J. A. T., Mojica Flores, R., Lakey Beitia, J., Vásquez Chaves, V., Zhang, Y., Calderón, A. I., Tayler, N., Keyzers, R. A., Tugizimana, F., Ndlovu, N., Aksenov, A. A., Jarmusch, A. K., Schmid, R., Truman, A. W., Bandeira, N., Wang, M., & Dorrestein, P. C. (2020). Reproducible molecular networking of untargeted mass spectrometry data using GNPS. Nature Protocols, 15, 1954–1991.
Arruda, R., Fadini, R. F., Carvalho, L. N., Del Claro, K., Mourão, F. A., Jacobi, C. M., Teodoro, G. S., van den Berg, E., Caires, C. S., & Dettke, G. A. (2012). Ecology of neotropical mistletoes: An important canopy dwelling component of Brazilian ecosystems. Acta Botanica Brasilica, 26(2), 264–274.
Barbero, M., Artuso, E., & Prandi, C. (2018). Fungal anticancer metabolites: Synthesis toward drug discovery. Current Medicinal Chemistry, 25(2), 141–185.
Barabadi, H., Alizadeh, Z., Rahimi, M. T., Barac, A., Maraolo, A. E., Robertson, L. J., Masjedi, A., Shahrivar, F., & Ahmadpour, E. (2019). Nanobiotechnology as an emerging approach to combat malaria: A systematic review. Nanomedicine, 18, 221–233.
Banerjee, D. (2011). Endophytic fungal diversity in tropical and subtropical plants. Journal of Microbiology, 6(1), 54–62.
Gruber Dorninger, C., Novak, B., Nagl, V., & Berthiller, F. (2016). Emerging mycotoxins: Beyond traditionally determined food contaminants. Journal of Agricultural and Food Chemistry, 65, 7052–7070.
Garcia, A. C. G., Menezes Júnior, O. T., Mariano, L. A., Santiago, L. C., Araújo, Â. R., Monfardini, J. D., Simões, R. C., Oliveira, A. C., Roque, R. A., Tadei, W. P., Teles, H. L., & Oliveira, C. M. (2022). Endophytic fungus Phomopsis sp. as a source of 3 nitropropionic acid with larvicidal activity against Aedes aegypti (Linnaeus 1762, Diptera: Culicidae). Journal of the Brazilian Society of Tropical Medicine, 55, 1–4.
Knakiewicz, A. C., Lutinski, J. A., Busato, M. A., Roman Junior, W. A., & Simões, D. A. (2020). Larvicidal activity of aqueous extracts of Ilex paraguariensis and Ilex theezans on Aedes aegypti (L.). Ciência e Natura, 42, 1–13.
Kim, J. W., & Shim, S. H. (2019). The fungus Colletotrichum as a source for bioactive secondary metabolites. Archives of Pharmacal Research, 42, 735–753.
Li, S., Zhang, X., Wang, X., & Zhao, C. (2018). Novel natural compounds from endophytic fungi with anticancer activity. European Journal of Medicinal Chemistry, 156, 316–343.
Ma, X., Nontachaiyapoom, S., Jayawardena, S. R., Yde, K. D., Gentekaki, E., Zhou, S., Qian, Y., Wen, T., & Kang, J. (2018). Endophytic Colletotrichum species from Dendrobium spp. in China and Northern Thailand. MycoKeys, 43, 23–57.
Maier, W., Hammer, K., Dammann, U., Schulz, B., & Strack, D. (1997). Accumulation of sesquiterpenoid cyclohexenone derivatives induced by an arbuscular mycorrhizal fungus in members of the Poaceae. Planta, 202(1), 36–42.
Masi, M., Cimmino, A., Tabanca, N., Becnel, J. J., Bloomquist, J. R., & Evidente, A. (2017). A survey of bacterial, fungal and plant metabolites against Aedes aegypti (Diptera: Culicidae), the vector of yellow and dengue fevers and Zika virus. Open Chemistry, 15, 156–166.
Munasinghe, V., Kumar, N. S., Jayasinghe, L., & Fujimoto, Y. (2017). Indole 3 acetic acid production by Colletotrichum siamense, an endophytic fungus from Piper nigrum leaves. Journal of Biologically Active Products from Nature, 7(6), 475–479.
Orlandelli, R. C., Alberto, R. N., Rubin Filho, C. J., & Pamphile, J. A. (2012). Diversity of endophytic fungal community associated with Piper hispidum (Piperaceae) leaves. Genetics and Molecular Research, 11(2), 1575–1585.
Pilz Junior, H. L., Lemos, A. B., Almeida, K. N., Corção, G., Schrekker, H. S., Silva, C. E., & Silva, O. S. (2019). Microbiota potentialized larvicidal action of imidazolium salts against Aedes aegypti (Diptera: Culicidae). Scientific Reports, 9(1), 1–8.
Pilon, A. C., Grande, M. D., Silvério, M. R. S., Silva, R. R., Albernaz, L. C., Vieira, P. C., Lopes, J. L. C., Espindola, L, S., & Lopes, N. P. (2022). Combination of GC–MS molecular networking and larvicidal effect against Aedes aegypti for the discovery of bioactive substances in commercial essential oils. Molecules, 27(5), 1–17.
Segaran, G., & Sathiavelu, M. (2019). Fungal endophytes: A potent biocontrol agent and a bioactive metabolites reservoir. Biocatalysis and Agricultural Biotechnology, 21, 1–17.
Vieira, W. A. S., Michereff, S. J., Morais Jr, M. A., Hyde, K. D., & Câmara, M. P. S. (2014). Endophytic species of Colletotrichum associated with mango in northeastern Brazil. Fungal Diversity, 67, 181–202.
Wang, M., Carver, J. J., Phelan, V. V., Sanchez, L. M., Garg, N., Peng, Y., Nguyen, D. D., Watrous, J., Kapono, C. A., Luzzatto Knaan, T., Porto, C., Bouslimani, A., Melnik, A. V., Meehan, M. J., Liu, W. T., Crüsemann, M., Boudreau, P. D., Esquenazi, E., Sandoval Calderón, M., Kersten, R. D., Pace, L. A., Quinn, R. A., Duncan, K. R. & Bandeira, N. (2016). Sharing and community curation of mass spectrometry data with Global Natural Products Social Molecular Networking. Nature Biotechnology, 34(8), 828–837.
Wang, M., Carver, J. J., Phelan, V. V., Sanchez, L. M., Garg, N., Peng, Y., Nguyen, D. D., Watrous, J., Kapono, C. A., Luzzatto-Knaan, T., Porto, C., Bouslimani, A., Melnik, A. V., Meehan, M. J., Liu, W. T., Crüsemann, M., Boudreau, P. D., Esquenazi, E., Sandoval-Calderón, M., Kersten, R. D., Pace, L. A., Quinn, R. A., Duncan, K. R., Hsu, C. C., Floros, D. J., Gavilan, R. G., Kleigrewe, K., Northen, T., Dutton, R. J., Parrot, D., Carlson, E. E., Aigle, B., Michelsen, C. F., Jelsbak, L., Sohlenkamp, C., Pevzner, P., Edlund, A., McLean, J., Piel, J., Murphy, B. T., Gerwick, L., Liaw, C.-C., Yang, Y.-L., Humpf, H.-U., Maansson, M., Keyzers, R. A., Sims, A. C., Johnson, A. R., Sidebottom, A. M., Sedio, B. E., Klitgaard, A., Larson, C. B., Boya P, C. A., Torres-Mendoza, D., Gonzalez, D. J., Silva, D. B., Marques, L. M., Demarque, D. P., Pociute, E., O’Neill, E. C., Briand, E., Helfrich, E. J. N., Granatosky, E. A., Glukhov, E., Ryffel, F., Houson, H., Mohimani, H., Kharbush, J. J., Zeng, Y., Vorholt, J. A., Kurita, K. L., Charusanti, P., McPhail, K. L., Nielsen, K. F., Vuong, L., Elfeki, M., Traxler, M. F., Engene, N., Koyama, N., Vining, O. B., Baric, R., Silva, R. R., Mascuch, S. J., Tomasi, S., Jenkins, S., Macherla, V., Hoffman, T., Agarwal, V., Williams, P. G., Dai, J., Neupane, R., Gurr, J., Rodríguez, A. M. C., Lamsa, A., Zhang, C., Dorrestein, K., Duggan, B. M., Almaliti, J., Allard, P.-M., Phapale, P., Nothias, L.-F., Alexandrov, T., Litaudon, M., Wolfender, J.-L., Kyle, J. E., Metz, T. O., Peryea, T., Nguyen, D.-T., VanLeer, D., Shinn, P., Jadhav, A., Müller, R., Waters, K. M., Shi, W., Liu, X., Zhang, L., Knight, R., Jensen, P. R., Palsson, B. Ø., Pogliano, K., Linington, R. G., Gutiérrez, M., Lopes, N. P., Gerwick, W. H., Moore, B. S., Dorrestein, P. C., & Bandeira, N. (2016). Sharing and community curation of mass spectrometry data with Global Natural Products Social Molecular Networking. Nature Biotechnology, 34(8), 828–837.
Wang, Z., Perumalsamy, H., Wang, X., & Ahn, Y. (2019). Toxicity and possible mechanisms of action of honokiol from Magnolia denudata seeds against four mosquito species. Scientific Reports, 9(411), 1–19.
World Health Organization. (2013). Guidelines for efficacy testing of spatial repellents.
Published
How to Cite
Issue
Section
License
Copyright (c) 2025 Ciência e Natura

This work is licensed under a Creative Commons Attribution-NonCommercial-ShareAlike 4.0 International License.
To access the DECLARATION AND TRANSFER OF COPYRIGHT AUTHOR’S DECLARATION AND COPYRIGHT LICENSE click here.
Ethical Guidelines for Journal Publication
The Ciência e Natura journal is committed to ensuring ethics in publication and quality of articles.
Conformance to standards of ethical behavior is therefore expected of all parties involved: Authors, Editors, Reviewers, and the Publisher.
In particular,
Authors: Authors should present an objective discussion of the significance of research work as well as sufficient detail and references to permit others to replicate the experiments. Fraudulent or knowingly inaccurate statements constitute unethical behavior and are unacceptable. Review Articles should also be objective, comprehensive, and accurate accounts of the state of the art. The Authors should ensure that their work is entirely original works, and if the work and/or words of others have been used, this has been appropriately acknowledged. Plagiarism in all its forms constitutes unethical publishing behavior and is unacceptable. Submitting the same manuscript to more than one journal concurrently constitutes unethical publishing behavior and is unacceptable. Authors should not submit articles describing essentially the same research to more than one journal. The corresponding Author should ensure that there is a full consensus of all Co-authors in approving the final version of the paper and its submission for publication.
Editors: Editors should evaluate manuscripts exclusively on the basis of their academic merit. An Editor must not use unpublished information in the editor's own research without the express written consent of the Author. Editors should take reasonable responsive measures when ethical complaints have been presented concerning a submitted manuscript or published paper.
Reviewers: Any manuscripts received for review must be treated as confidential documents. Privileged information or ideas obtained through peer review must be kept confidential and not used for personal advantage. Reviewers should be conducted objectively, and observations should be formulated clearly with supporting arguments, so that Authors can use them for improving the paper. Any selected Reviewer who feels unqualified to review the research reported in a manuscript or knows that its prompt review will be impossible should notify the Editor and excuse himself from the review process. Reviewers should not consider manuscripts in which they have conflicts of interest resulting from competitive, collaborative, or other relationships or connections with any of the authors, companies, or institutions connected to the papers.


