Antifungal activity of eugenol derivatives against Botrytis cinerea

Andrés F. Olea, Angelica Bravo, Rolando Martínez, Mario Thomas, Claudia Sedan, Luis Espinoza, Elisabeth Zambrano, Denisse Carvajal, Evelyn Silva-Moreno, Héctor Carrasco

Resultado de la investigación: Article

1 Cita (Scopus)

Resumen

Botrytis cinerea is a worldwide spread fungus that causes the grey mold disease, which is considered the most important factor in postharvest losses in fresh fruit crops. Consequently, the control of gray mold is a matter of current and relevant interest for agricultural industries. In this work, a series of phenylpropanoids derived from eugenol were synthesized and characterized. Their effects on the mycelial growth of a virulent and multi-resistant isolate of B. cinerea (PN2) have been evaluated and IC 50 values for the most active compounds range between 31–95 ppm. The antifungal activity exhibited by these compounds is strongly related to their chemical structure, i.e., increasing activity has been obtained by isomerization of the double bond or introduction of a nitro group on the aromatic ring. Based on the relationship between the fungicide activities and chemical structure, a mechanism of action is proposed. Finally, the activity of these compounds is higher than that reported for the commercial fungicide BC-1000 that is currently employed to combat this disease. Thus, our results suggest that these compounds are potential candidates to be used in the design of new and effective control with inspired natural compounds of this pathogen.

Idioma originalEnglish
Número de artículo1239
PublicaciónMolecules
DOI
EstadoPublished - 29 mar 2019

Huella dactilar

Botrytis
Eugenol
Fungicides
Fungi
fungicides
Derivatives
Pathogens
Isomerization
Fruits
Crops
combat
pathogens
fungi
fruits
Fruit
crops
Industry
isomerization
industries
Growth

ASJC Scopus subject areas

  • Analytical Chemistry
  • Chemistry (miscellaneous)
  • Molecular Medicine
  • Pharmaceutical Science
  • Drug Discovery
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Citar esto

Olea, A. F., Bravo, A., Martínez, R., Thomas, M., Sedan, C., Espinoza, L., ... Carrasco, H. (2019). Antifungal activity of eugenol derivatives against Botrytis cinerea. Molecules, [1239]. https://doi.org/10.3390/molecules24071239
Olea, Andrés F. ; Bravo, Angelica ; Martínez, Rolando ; Thomas, Mario ; Sedan, Claudia ; Espinoza, Luis ; Zambrano, Elisabeth ; Carvajal, Denisse ; Silva-Moreno, Evelyn ; Carrasco, Héctor. / Antifungal activity of eugenol derivatives against Botrytis cinerea. En: Molecules. 2019.
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abstract = "Botrytis cinerea is a worldwide spread fungus that causes the grey mold disease, which is considered the most important factor in postharvest losses in fresh fruit crops. Consequently, the control of gray mold is a matter of current and relevant interest for agricultural industries. In this work, a series of phenylpropanoids derived from eugenol were synthesized and characterized. Their effects on the mycelial growth of a virulent and multi-resistant isolate of B. cinerea (PN2) have been evaluated and IC 50 values for the most active compounds range between 31–95 ppm. The antifungal activity exhibited by these compounds is strongly related to their chemical structure, i.e., increasing activity has been obtained by isomerization of the double bond or introduction of a nitro group on the aromatic ring. Based on the relationship between the fungicide activities and chemical structure, a mechanism of action is proposed. Finally, the activity of these compounds is higher than that reported for the commercial fungicide BC-1000 that is currently employed to combat this disease. Thus, our results suggest that these compounds are potential candidates to be used in the design of new and effective control with inspired natural compounds of this pathogen.",
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Olea, AF, Bravo, A, Martínez, R, Thomas, M, Sedan, C, Espinoza, L, Zambrano, E, Carvajal, D, Silva-Moreno, E & Carrasco, H 2019, 'Antifungal activity of eugenol derivatives against Botrytis cinerea', Molecules. https://doi.org/10.3390/molecules24071239

Antifungal activity of eugenol derivatives against Botrytis cinerea. / Olea, Andrés F.; Bravo, Angelica; Martínez, Rolando; Thomas, Mario; Sedan, Claudia; Espinoza, Luis; Zambrano, Elisabeth; Carvajal, Denisse; Silva-Moreno, Evelyn; Carrasco, Héctor.

En: Molecules, 29.03.2019.

Resultado de la investigación: Article

TY - JOUR

T1 - Antifungal activity of eugenol derivatives against Botrytis cinerea

AU - Olea, Andrés F.

AU - Bravo, Angelica

AU - Martínez, Rolando

AU - Thomas, Mario

AU - Sedan, Claudia

AU - Espinoza, Luis

AU - Zambrano, Elisabeth

AU - Carvajal, Denisse

AU - Silva-Moreno, Evelyn

AU - Carrasco, Héctor

PY - 2019/3/29

Y1 - 2019/3/29

N2 - Botrytis cinerea is a worldwide spread fungus that causes the grey mold disease, which is considered the most important factor in postharvest losses in fresh fruit crops. Consequently, the control of gray mold is a matter of current and relevant interest for agricultural industries. In this work, a series of phenylpropanoids derived from eugenol were synthesized and characterized. Their effects on the mycelial growth of a virulent and multi-resistant isolate of B. cinerea (PN2) have been evaluated and IC 50 values for the most active compounds range between 31–95 ppm. The antifungal activity exhibited by these compounds is strongly related to their chemical structure, i.e., increasing activity has been obtained by isomerization of the double bond or introduction of a nitro group on the aromatic ring. Based on the relationship between the fungicide activities and chemical structure, a mechanism of action is proposed. Finally, the activity of these compounds is higher than that reported for the commercial fungicide BC-1000 that is currently employed to combat this disease. Thus, our results suggest that these compounds are potential candidates to be used in the design of new and effective control with inspired natural compounds of this pathogen.

AB - Botrytis cinerea is a worldwide spread fungus that causes the grey mold disease, which is considered the most important factor in postharvest losses in fresh fruit crops. Consequently, the control of gray mold is a matter of current and relevant interest for agricultural industries. In this work, a series of phenylpropanoids derived from eugenol were synthesized and characterized. Their effects on the mycelial growth of a virulent and multi-resistant isolate of B. cinerea (PN2) have been evaluated and IC 50 values for the most active compounds range between 31–95 ppm. The antifungal activity exhibited by these compounds is strongly related to their chemical structure, i.e., increasing activity has been obtained by isomerization of the double bond or introduction of a nitro group on the aromatic ring. Based on the relationship between the fungicide activities and chemical structure, a mechanism of action is proposed. Finally, the activity of these compounds is higher than that reported for the commercial fungicide BC-1000 that is currently employed to combat this disease. Thus, our results suggest that these compounds are potential candidates to be used in the design of new and effective control with inspired natural compounds of this pathogen.

KW - Botrytis cinerea

KW - Chemical fungicides

KW - Eugenol

KW - Mycelial growth

KW - Reactive oxygen species

KW - Resistant isolate

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