Fungitoxicity against Botrytis cinerea of a Flavonoid Isolated from Pseudognaphalium robustum

Cotoras, Milena; Mendoza, Leonora; Muñoz, Alexis; Yáñez, Karen P.; Castro, Paulo de Tarso Oliveira e; Aguirre, Marı́a J.

doi:10.3390/molecules16053885

Cited by 26 publications

(24 citation statements)

References 27 publications

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“…Conidial germination assay was carried out as described by Cotoras et al 25 using the synthesized compound, syringic acid, or aniline dissolved in acetone at a final concentration of 0.16mM. The final acetone concentration was identical in the control and treatment assays.…”

Section: Effect On Conidial Germinationmentioning

confidence: 99%

Improvement of the Antifungal Activity Against Botrytis Cinerea of Syringic Acid, a Phenolic Acid From Grape Pomace

Mendoza

Castro

Melo

et al. 2016

J. Chil. Chem. Soc.

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The aim of this study was to improve the antifungal activity against Botrytis cinerea of syringic acid by using the enzyme laccase to synthesize a heterodimeric compound by a coupling reaction with aniline. The synthesized heterodimer is a quinone-imine like compound (2,6-dimethoxy-4-(phenylimino)benzenone), which was characterized by using 1 H and 13 C NMR, IR, and mass spectrometry. The antifungal activity of the heterodimeric compound against B. cinerea was determined in vitro and showed a higher antifungal effect than the substrates (syringic acid and aniline), inhibiting the mycelial growth with an IC 50 value of 0.14mM and delayed 2 hours the conidial germination. Also, using the fluorochrome calcofluor white, cell wall damage was observed when B. cinerea was incubated with the compound. This is the first report on antifungal activity of this type of compound against B. cinerea.

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Section: Effect On Conidial Germinationmentioning

confidence: 99%

Improvement of the Antifungal Activity Against Botrytis Cinerea of Syringic Acid, a Phenolic Acid From Grape Pomace

Mendoza

Castro

Melo

et al. 2016

J. Chil. Chem. Soc.

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“…To analyze if Sclareol and 13-epi-Sclareol are able to produce alteration of the integrity of B. cinerea cytoplasmic membrane, SYTOX Green uptake assay according to described by Cotoras et al (2011) 10 was used. B. cinerea conidia at a final concentration of 1x10 5 conidia / mL were inoculated in 24-well plates (lined with 12-mm glass coverslips) containing 1 mL of liquid minimum medium.…”

Section: Determination Of the Effect Of Diterpenoids On The Membrane mentioning

confidence: 99%

“…Oxygen consumption was determined polarographically at 25 °C with a Hansatech oxygen electrode by using germinating conidia in a total volume of 1 mL according the protocol previously described 10 . To obtain conidia in suspension, Murashige and Skoog´s basal medium at 4.4 (g/L) (Phytotechnology Laboratories, Lenexa, KS, USA) was added to Petri dishes containing conidia.…”

Section: Determination Of the Effect Of Diterpenoids On The Oxygen Comentioning

confidence: 99%

“…These compounds are widely distributed in nature and it has been described that some have antibacterial 7 , antiviral 8 and antifungal activities 9 . Cotoras et al (2001) reported the effect of the diterpenoid 3β -hydroxykaurenoic acid on the mycelial growth and conidia germination of B. cinerea 10 . Later, the same group reported that the mechanism of action of 3β-hydroxykaurenoic acid was based on the permeabilization of plasmatic membrane 11 .…”

Section: Introductionmentioning

confidence: 99%

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Characterization of the Antifungal Activity Against Botrytis Cinerea of Sclareol and 13-Epi-Sclareol, Two Labdane-Type Diterpenoids

Mendoza

Sepúlveda

Melo

et al. 2015

J. Chil. Chem. Soc.

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The antifungal activity of Sclareol and 13-epi-Sclareol, two labdane-type diterpenoids, on mycelial growth of the phytopathogenic fungus Botrytis cinerea was evaluated. Diterpenoid fungitoxicity was assessed using the radial growth test method. Both diterpenoids inhibited the mycelial growth of B. cinerea in solid medium; however the inhibitory activity of Sclareol was slightly higher than 13-epi-Sclareol with IC 50 value of 237.6 µg/mL and 268.8 µg/mL, respectively. On the other hand, both labdane-type diterpenoids did not alter the plasmatic membrane integrity; however the oxygen consumption of B. cinerea germinating conidia was affected. The evidence suggests that action mechanism of these molecules would be related to the uncoupling of mitochondrial oxidative phosphorylation. Finally, biotransformation of Sclareol by B. cinerea was analysed and the main biotransformed metabolite was identified as 3β-hydroxysclareol.

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“…Furthermore, they apparently are more biodegradable and less toxic to humans and the environment than the commercial fungicides in use (COTORAS et al, 2011). Naturally occurring chalcones are key intermediates in flavonoid biosynthesis by plants, which can be easily synthesized through several procedures (MCMURRY 2000;SEBTI et al, 2001;EDDARIR et al, 2003;PETROV;IVANOVA;GEROVA, 2008).…”

Section: Introductionmentioning

confidence: 99%

Chalcones to control Alternaria alternata in murcott tangor fruits

Camargos¹,

Perina²,

Carvalho³

et al. 2016

Biosci. J.

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Alternaria brown spot (ABS), caused by the fungus Alternaria alternata pathotype tangerine, is one of the main phytosanitary problems for mandarin growers. About 15 applications per year of harmful fungicides are required for controlling ABS disease in citrus orchards. As chalcones seem to be less toxic to humans and environment than the commercial fungicides in use, this study initially aimed at synthesizing 137 chalcones through aldolic condensations between benzaldehydes and acetophenones. The resulting chalcones were screened for activity against A. alternata through a fungal growth assay that was carried out in 96-cell polypropylene plates, using the same concentration to all studied substances. The four active chalcones underwent conidia germination and mycelial growth, which confirmed the antifungal activity of the compounds. These chalcones were then poured onto Murcott tangor fruit that had been inoculated with conidia of the fungus. All four chalcones reduced the ABS progress to values significantly smaller (P≤0.05) than that observed for the control. Statistical calculations showed that the best results were afforded by two compounds, bearing a 2,4,5-trimethoxyphenyl group at position 3 of prop-2-enal and a 3-nitro-or 3-hydroxyphenyl group at position 1 of the aldehyde. Such compounds reduced the incidence of the disease in Murcott tangor fruit to values that did not differ statistically from those obtained with a commercial fungicide.

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Fungitoxicity against Botrytis cinerea of a Flavonoid Isolated from Pseudognaphalium robustum

Cited by 26 publications

References 27 publications

Improvement of the Antifungal Activity Against Botrytis Cinerea of Syringic Acid, a Phenolic Acid From Grape Pomace

Improvement of the Antifungal Activity Against Botrytis Cinerea of Syringic Acid, a Phenolic Acid From Grape Pomace

Characterization of the Antifungal Activity Against Botrytis Cinerea of Sclareol and 13-Epi-Sclareol, Two Labdane-Type Diterpenoids

Chalcones to control Alternaria alternata in murcott tangor fruits

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