Antifungal activity of β-carbolines on Penicillium digitatum and Botrytis cinerea

Olmedo, Gabriela María; Cerioni, Luciana; Gonzalez, M. Micaela; Cabrerizo, Franco M.; Rapisarda, Viviana Andrea; Volentini, Sabrina Inès

doi:10.1016/j.fm.2016.09.011

Cited by 58 publications

(43 citation statements)

References 30 publications

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“…Harmol has antimicrobial properties against P. digitatum and B. cinerea (Olmedo et al, 2017). The exposure to this compound inhibited germination, mycelial growth, sporulation and residual infectivity of these microorganisms.…”

Section: Discussionmentioning

confidence: 99%

“…p K a values at room temperature were determined from changes in UV-vis absorption spectra of aqueous solutions of harmol, following the procedure described elsewhere (Cabrerizo et al, 2004). For antifungal assays, harmol stock solution was prepared in dimethyl sulfoxide (DMSO, Sigma-Aldrich Co.) and its concentration was calculated using the 𝜀 320nm = 18965 M -1 cm -1 , as previously described by Olmedo et al (2017).…”

Section: Methodsmentioning

confidence: 99%

“…P. digitatum was isolated from lemons (Cerioni et al, 2009) and B. cinerea from blueberries (Olmedo et al, 2017). Both strains have been previously deposited with codes ICFC 842/15 and ICFC 841/15 in the IIB-INTECH collection of Fungal Cultures (ICFC, from the Laboratory of Mycology and Mushroom Cultivation, IIB-INTECH, Chascomús, Argentina; WDCM data base reference: 826).…”

Section: Methodsmentioning

confidence: 99%

“…B. cinerea sporulation was induced by placing a sterile wood stick onto the growing colony and incubating for further 7 days (Olmedo et al, 2017). …”

Section: Methodsmentioning

confidence: 99%

“…It has been previously reported that, among six βCs tested, harmol exhibited the highest inhibitory effect on P. digitatum and B. cinerea (Olmedo et al, 2017). At a concentration of 1 mM, this full aromatic βC provoked a complete germination inhibition of B. cinerea and P. digitatum conidia.…”

Section: Introductionmentioning

confidence: 93%

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UVA Photoactivation of Harmol Enhances Its Antifungal Activity against the Phytopathogens Penicillium digitatum and Botrytis cinerea

et al. 2017

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Phytopathogenic fungi responsible for post-harvest diseases on fruit and vegetables cause important economic losses. We have previously reported that harmol (1-methyl-9H-pyrido[3,4-b]indol-7-ol) is active against the causal agents of green and gray molds Penicillium digitatum and Botrytis cinerea, respectively. Here, antifungal activity of harmol was characterized in terms of pH dependency and conidial targets; also photodynamic effects of UVA irradiation on the antimicrobial action were evaluated. Harmol was able to inhibit the growth of both post-harvest fungal disease agents only in acidic conditions (pH 5), when it was found in its protonated form. Conidia treated with harmol exhibited membrane integrity loss, cell wall disruption, and cytoplasm disorganization. All these deleterious effects were more evident for B. cinerea in comparison to P. digitatum. When conidial suspensions were irradiated with UVA in the presence of harmol, antimicrobial activity against both pathogens was enhanced, compared to non-irradiated conditions. B. cinerea exhibited a high intracellular production of reactive oxygen species (ROS) when was incubated with harmol in irradiated and non-irradiated treatments. P. digitatum showed a significant increase in ROS accumulation only when treated with photoexcited harmol. The present work contributes to unravel the antifungal activity of harmol and its photoexcited counterpart against phytopathogenic conidia, focusing on ROS accumulation which could account for damage on different cellular targets.

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Section: Discussionmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

“…B. cinerea sporulation was induced by placing a sterile wood stick onto the growing colony and incubating for further 7 days (Olmedo et al, 2017). …”

Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 93%

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UVA Photoactivation of Harmol Enhances Its Antifungal Activity against the Phytopathogens Penicillium digitatum and Botrytis cinerea

et al. 2017

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Fungicidal activity of novel quinazolin‐6‐ylcarboxylates and mode of action on Botrytis cinerea

Yan

Chen

et al. 2023

Pest Management Science

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BACKGROUND Fungal diseases remain important causes of crop failure and economic losses. As the resistance toward current selective fungicides becomes increasingly problematic, it is necessary to develop efficient fungicides with novel chemotypes. RESULTS A series of novel quinazolin‐6‐ylcarboxylates which combined the structures of pyridine or heterocyclic motif and the N‐(3‐chloro‐4‐fluorophenyl)quinazolin‐4‐amine moiety, a binding group of ATP‐binding site of gefitinib, were evaluated for their fungicidal activity on different phytopathogenic fungi. Most of these compounds showed excellent fungicidal activities against Botrytis cinerea and Exserohilum rostratum, especially compound F17 displayed the highest activity with EC50 values as 3.79 μg mL−1 against B. cinerea and 2.90 μg mL−1 against E. rostratum, which was similar to or even better than those of the commercial fungicides, such as pyraclostrobin (EC50, 3.68, 17.38 μg mL−1) and hymexazol (EC50, 4.56, 2.13 μg mL−1). Moreover, compound F17 significantly arrested the lesion expansion of B. cinerea infection on tomato detached leaves and strongly suppressed grey mold disease on tomato seedlings in greenhouse. The abilities of compound F17 to induce cell apoptosis of the non‐germinated spores, to limit oxalic acid production, to reduce malate dehydrogenase (MDH) expression, and to block the active pocket of MDH protein were demonstrated in B. cinerea. CONCLUSION The novel quinazolin‐6‐ylcarboxylates containing ATP‐binding site‐directed moiety, especially compound F17, could be developed as a potential fungicidal candidate for further study. © 2023 Society of Chemical Industry.

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Synthesis, Structural Characterization and Biological Evaluation of Rhenium(I) Tricarbonyl Complexes with β‐Carboline Ligands.

et al. 2017

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Twob-carboline rhenium(I) complexes, fac-[Re(CO) 3 (dppz)(nHo)]O 3 SCF 3 and fac-[Re(CO) 3 (nHo) 2 Cl] where dppz = dipyrido[3, 2-a:2',3'-c] phenazine and nHo = 9H-pyrido [3, 4-b] indole (norharmane), have been synthesized. These complexes were fully characterized by structural X-ray diffraction, 1 H and 13 C NMR, UV-vis absorption and FT-IR spectroscopy and mass spectrometry. Ground state geometry optimization was carried out in vacuo with the PBE0 hybrid functional using the LanL2DZ basis set. The characterization was complemented with TD-DFT calculations using several hybrid functionals. Cellular uptake and cytotoxic effect of both complexes against human lung carcinoma (A549) cells were evaluated. For comparative purpose, two related fac-[Re(CO) 3 (L)(nHo)] + complexes (L = bpy and phen) were included in the biological studies. The anti-proliferative effect of the compounds was rationalized in terms of the different extension of the ligands psystem.

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Antifungal activity of β-carbolines on Penicillium digitatum and Botrytis cinerea

Cited by 58 publications

References 30 publications

UVA Photoactivation of Harmol Enhances Its Antifungal Activity against the Phytopathogens Penicillium digitatum and Botrytis cinerea

UVA Photoactivation of Harmol Enhances Its Antifungal Activity against the Phytopathogens Penicillium digitatum and Botrytis cinerea

Fungicidal activity of novel quinazolin‐6‐ylcarboxylates and mode of action on Botrytis cinerea

Synthesis, Structural Characterization and Biological Evaluation of Rhenium(I) Tricarbonyl Complexes with β‐Carboline Ligands.

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