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Biotechnology

Antifungal Effects of Drimane Sesquiterpenoids Isolated from Drimys winteri against Gaeumannomyces graminis var. tritici

Cristian Paz, Sharon Viscardi, Andres Iturra, Victor Marin, Felipe Miranda, Patricio Javier Barra, Isabel Mendez, Paola Duran
Irina S. Druzhinina, Editor
Cristian Paz
aLaboratorio de Productos Naturales y Descubrimiento de Fármacos, Departamento de Ciencias Básicas, Facultad de Medicina, Universidad de La Frontera, Temuco, Chile
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Sharon Viscardi
bDepartamento de Procesos Diagnósticos y Evaluación, Facultad de Ciencias de la Salud, Universidad Católica de Temuco, Temuco, Chile
eNúcleo de Investigación en Producción Alimentaria, Universidad Católica de Temuco, Temuco, Chile
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Andres Iturra
aLaboratorio de Productos Naturales y Descubrimiento de Fármacos, Departamento de Ciencias Básicas, Facultad de Medicina, Universidad de La Frontera, Temuco, Chile
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Victor Marin
aLaboratorio de Productos Naturales y Descubrimiento de Fármacos, Departamento de Ciencias Básicas, Facultad de Medicina, Universidad de La Frontera, Temuco, Chile
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Felipe Miranda
aLaboratorio de Productos Naturales y Descubrimiento de Fármacos, Departamento de Ciencias Básicas, Facultad de Medicina, Universidad de La Frontera, Temuco, Chile
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Patricio Javier Barra
cCenter of Plant, Soil Interaction and Natural Resources Biotechnology, Scientific and Technological Bioresource Nucleus, Temuco, Chile
dBiocontrol Research Laboratory, Universidad de La Frontera, Temuco, Chile
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Isabel Mendez
cCenter of Plant, Soil Interaction and Natural Resources Biotechnology, Scientific and Technological Bioresource Nucleus, Temuco, Chile
dBiocontrol Research Laboratory, Universidad de La Frontera, Temuco, Chile
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Paola Duran
cCenter of Plant, Soil Interaction and Natural Resources Biotechnology, Scientific and Technological Bioresource Nucleus, Temuco, Chile
dBiocontrol Research Laboratory, Universidad de La Frontera, Temuco, Chile
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Irina S. Druzhinina
Nanjing Agricultural University
Roles: Editor
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DOI: 10.1128/AEM.01834-20
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ABSTRACT

Gaeumannomyces graminis var. tritici is a soilborne pathogen that causes “take-all” disease, affecting cereal roots. In wheat, G. graminis var. tritici is the most important biotic factor, causing around 30 to 50% losses of yield. Chemical control of this fungal disease is difficult because G. graminis var. tritici is able to reside for a long time in soils. Therefore, the development of environmentally friendly biotechnological strategies to diminish the incidence of soilborne diseases is highly desirable. Natural products are a promising strategy for biocontrol of plant pathogens. A special emphasis is on medicinal plants due to their reported fungitoxic effects. Drimys winteri (canelo) is a medicinal plant that is widely used by the Mapuche ethnic group from Chile due to its anti-inflammatory activity. In addition, inhibitory effects of canelo against phytopathogenic fungi and pest insects have been reported. In this study, we isolated, purified, and identified six drimane sesquiterpenoid compounds from canelo (drimenin, drimenol, polygodial, isodrimeninol, valdiviolide, and drimendiol). Then, we evaluated their antimicrobial effects against G. graminis var. tritici. Compounds were identified by comparing Fourier-transform infrared spectroscopy (FTIR) data and the retention time in thin-layer chromatography (TLC) with those of pure standards. The putative antagonistic effects were confirmed by assessing hyphal cell wall damage using confocal microscopy and lipid peroxidation. Here, we reported the high potential of drimane sesquiterpenoids as natural antifungals against G. graminis var. tritici. Polygodial and isodrimeninol were the most effective, with 50% lethal concentrations (LC50s) between 7 and 10 μg ml−1 and higher levels of fungal lipid peroxidation seen. Accordingly, natural sesquiterpenoids purified from canelo are biologically active against G. graminis var. tritici and could be used as natural biofungicides for sustainable agriculture.

IMPORTANCE More than two billion tons of pesticides are used every year worldwide. An interesting sustainable alternative to control plant pathogens is the use of natural products obtained from plants, mainly medicinal plants that offer secondary metabolites important to human/animal health. In this study, we isolated and identified six pure drimane sesquiterpenoids obtained from the bark of Drimys winteri. Additionally, we evaluated their antifungal activities against Gaeumannomyces graminis (the main biotic factor affecting cereal production, especially wheat) by assessing fungal cell wall damage and lipid peroxidation. The compounds obtained showed important antifungal properties against G. graminis var. tritici, mainly isodrimenol, which was the second-most-active compound after polygodial, with an LC50 against G. graminis var. tritici of around 9.5 μg ml−1. This information could be useful for the development of new natural or hemisynthetic antifungal agents against soilborne phytopathogens that could be used in green agriculture.

FOOTNOTES

    • Received 31 July 2020.
    • Accepted 2 October 2020.
    • Accepted manuscript posted online 9 October 2020.
  • Supplemental material is available online only.

  • Copyright © 2020 American Society for Microbiology.

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Antifungal Effects of Drimane Sesquiterpenoids Isolated from Drimys winteri against Gaeumannomyces graminis var. tritici
Cristian Paz, Sharon Viscardi, Andres Iturra, Victor Marin, Felipe Miranda, Patricio Javier Barra, Isabel Mendez, Paola Duran
Applied and Environmental Microbiology Nov 2020, 86 (24) e01834-20; DOI: 10.1128/AEM.01834-20

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Antifungal Effects of Drimane Sesquiterpenoids Isolated from Drimys winteri against Gaeumannomyces graminis var. tritici
Cristian Paz, Sharon Viscardi, Andres Iturra, Victor Marin, Felipe Miranda, Patricio Javier Barra, Isabel Mendez, Paola Duran
Applied and Environmental Microbiology Nov 2020, 86 (24) e01834-20; DOI: 10.1128/AEM.01834-20
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KEYWORDS

natural products
antifungal agents
membrane disruption
take-all disease

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