Abstract
Bioassay-guided fractionation of the organic extracts of the endophyte Daldinia eschscholtzii strain GsE13 led to the isolation of several phytotoxic compounds, including two chromenone and two chromanone derivatives: 5-hydroxy-8-methoxy-2-methyl-4H-chromen-4-one, 1; 5-hydroxy-2-methyl-4H-chromen-4-one, 2; 5-methoxy-2-methyl-chroman-4-one, 3; and 5-methoxy-2-methyl-chroman-4-ol, 4; as well as other aromatic compounds: 4,8-dihydroxy-1-tetralone, 5; 1,8-dimethoxynaphthalene, 6; and 4,9-dihydroxy-1,2,11,12-tetrahydroperyl-ene-3,10-quinone, 7. Compounds 1, 4, and 7 were isolated for the first time from D. eschscholtzii. The phytotoxicity of all the compounds was determined on germination, root growth, and oxygen uptake in seedlings of a monocotyledonous (Panicum miliaceum) and three dicotyledonous plants (Medicago sativa, Trifolium pratense, and Amaranthus hypochondriacus). In general, root growth was the most affected process in all four weeds, and chromenones 1 and 2 were the most phytotoxic compounds. Phytotoxins 1–4 inhibited basal oxygen consumption rate in isolated mitochondria from M. sativa seedlings and also caused serious damage to their membrane potential (ΔΨm) in percentages greater than 50% at concentrations lower than 2 mM. Based on these results, compounds 1–4 of endophytic origin could be promising for the development of new herbicides potentially useful in agriculture or for the synthesis of promising new molecules.
Key points
• Endophytic fungus Daldinia eschscholtzii produces phytotoxic compounds.
• Phytotoxins inhibit basal oxygen consumption rate in isolated M. sativa mitochondria.
• Phytotoxins altered the mitochondrial membrane potential.
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Data Availability
All data generated or analyzed during the present study are included in this published article (and in the supplementary information files).
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Acknowledgements
The authors recognize the valuable support of Beatriz Quiroz García, Elizabeth Huerta Salazar, Ma. De los Ángeles Peña González, Ma. del Carmen García-González, Javier Pérez Flores, and Rocío Patiño Maya from the Instituto de Química, UNAM, for recording NMR, IR, UV, and MS spectra; of Julio César Montero Rojas and Samuel Aguilar Ogarrio, from the Instituto de Biología, UNAM, for their support with the culture photographs of D. eschscholtzii; of Rebeca Martínez, from the Instituto de Biología, UNAM, for her support with the bright-field micrographs; and of Diana Almaguer, from the Instituto de Biología, UNAM, for assembling the photograph plates.
Funding
This work was funded by the Consejo Nacional de Ciencia y Tecnología, Mexico (CONACyT, grant A1-S-20469), and the Programa de Apoyo a Proyectos de Investigación e Innovación Tecnológica (PAPIIT-DGAPA, UNAM IN210920). Additionally, this study used the UNAM’s NMR lab, LURMN at IQ-UNAM, co-funded by CONACyT Mexico (Project 0224747) and UNAM. Mónica Flores is a PhD student from the Programa de Doctorado en Ciencias Biomédicas, Universidad Nacional Autónoma de México (UNAM), and received fellowship 576329 from CONACyT.
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FR conducted experiments, analyzed data, and wrote the first draft of the manuscript. PL carried out the fungus identification using molecular tools and wrote its description. MR conceived and designed the research, directed data analysis, and wrote the manuscript and revision. All authors read and approved the final version of the manuscript.
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A comparative Nucleotide BLAST analysis of the ITS strain GsE13 sequence is available free of charge via the Internet at http://pubs.acs.org. The online version of this article contains supplementary material (Materials and methods and Tables S1-S3), which is available to authorized users. (PDF 538 kb).
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Flores-Reséndiz, M., Lappe-Oliveras, P. & Macías-Rubalcava, M.L. Mitochondrial damage produced by phytotoxic chromenone and chromanone derivatives from endophytic fungus Daldinia eschscholtzii strain GsE13. Appl Microbiol Biotechnol 105, 4225–4239 (2021). https://doi.org/10.1007/s00253-021-11318-7
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DOI: https://doi.org/10.1007/s00253-021-11318-7