Citronellal Exerts Its Antifungal Activity by Targeting Ergosterol Biosynthesis in Penicillium digitatum

Ouyang, Qi; Liu, Yangmei; Reymick, Okwong Oketch; Zhang, Miaoling; Shao, Xingfeng; Tao, Nengguo

doi:10.3390/jof7060432

Cited by 40 publications

(31 citation statements)

References 40 publications

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“…The activity of citronellal, the principal constituent (93Á97%) of the essential oil extracted from Eucalyptus citriodora in this study, has already been studied against several fungi, and it has shown interference in membrane integrity and reduction in ergosterol levels as a mechanism of antifungal activity. This substance negatively regulates the ergosterol genes responsible for the conversion of lanosterol to ergosterol (Yang et al 2021). The same mechanisms of antifungal action described above for the chemical constituents of essential oils might have occurred with the fungus Hemileia vastatrix after treatments with Eucalyptus essential oils because these oils also contain these same substances.…”

Section: In Vitro Antifungal Activity Of Essential Oils and Nanoparti...mentioning

confidence: 82%

“…This substance negatively regulates the ergosterol genes responsible for the conversion of lanosterol to ergosterol (Yang et al . 2021). The same mechanisms of antifungal action described above for the chemical constituents of essential oils might have occurred with the fungus Hemileia vastatrix after treatments with Eucalyptus essential oils because these oils also contain these same substances.…”

Section: Resultsmentioning

confidence: 99%

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Antifungal activity of poly(ε-caprolactone) nanoparticles incorporated with Eucalyptus essential oils against Hemileia vastatrix

Caetano

Cardoso

Resende

et al. 2022

Letters in Applied Microbiology

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Coffee (Coffea L.) is one of the main crops produced globally. Its contamination by the fungus Hemileia vastatrix Berkeley and Broome has been economically detrimental for producers. The objective of this work was to extract and characterize the essential oils from Eucalyptus citriodora Hook, Eucalyptus camaldulensis Dehn and Eucalyptus grandis Hill ex Maiden, produce and characterize nanoparticles containing these essential oils and evaluate the in vivo and in vitro antifungal activity of free and nanoencapsulated essential oils. The principal constituent of the essential oil from E. citriodora was citronellal; that from E. grandis was α‐pinene; and that from E. camaldulensis was 1,8‐cineol. The in vitro antifungal activity against the fungus H. vastatrix was 100% at a concentration of 1000 μl l−1 for all the oils and nanoparticles containing these natural products. The sizes of the nanoparticles produced with the essential oils from E. citriodora, E. camaldulensis and E. grandis were 402·13 nm, 275·33 nm and 328·5 nm, respectively, with surface charges of −11·8 mV, −9·24 mV and − 6·76 mV, respectively. Fourier transform infrared analyses proved that the encapsulation of essential oils occurred in the polymeric matrix of poly(ε‐caprolactone). The incorporation of essential oils into biodegradable poly(ε‐caprolactone) nanoparticles increased their efficiency as biofungicides in the fight against coffee rust, decreasing the severity of the disease by up to 90·75% after treatment with the nanoparticles containing the essential oil from E. grandis.

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Section: In Vitro Antifungal Activity Of Essential Oils and Nanoparti...mentioning

confidence: 82%

Section: Resultsmentioning

confidence: 99%

Antifungal activity of poly(ε-caprolactone) nanoparticles incorporated with Eucalyptus essential oils against Hemileia vastatrix

Caetano

Cardoso

Resende

et al. 2022

Letters in Applied Microbiology

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“…Since cell membrane of fungi in constituents and structures is different from mammalian, using it as a target is attractive for developing selective antifungal agents [47]. Currently, the majority of the available antifungals interfere with its functions either by binding with membrane ergosterol or through inhibition of various steps in ergosterol biosynthesis [48,49].…”

Section: Discussionmentioning

confidence: 99%

Isoflavaspidic Acid PB Extracted from Dryopteris fragrans (L.) Schott Inhibits Trichophyton rubrum Growth via Membrane Permeability Alternation and Ergosterol Biosynthesis Disruption

Zhang

Liu

Shen

et al. 2022

BioMed Research International

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Isoflavaspidic acid PB (PB), a phloroglucinol derivative extracted from aerial parts of Dryopteris fragrans (L.) Schott, had antifungal activity against several dermatophytes. This study was aimed at exploring the antifungal mechanism of PB against Trichophyton rubrum (T. rubrum). The effectiveness of PB in inhibiting T. rubrum growth was detected by time-kill kinetics study and fungal biomass determination. Studies on the mechanism of action were investigated using scanning electron microscopy (SEM), transmission electron microscopy (TEM), sorbitol and ergosterol assay, nucleotide leakage measurement, and UPLC-based test and enzyme-linked immunosorbent assay. Fungicidal activity of PB was concentration- and time-dependent at 2 × MIC (MIC: 20 μg/mL) after 36 h. The total biomass of T. rubrum was reduced by 64.17%, 77.65%, and 84.71% in the presence of PB at 0.5 × MIC , 1 × MIC , and 2 × MIC , respectively. SEM analysis showed that PB changed mycelial morphology, such as shrinking, twisting, collapsing, and even flattening. TEM images of treated cells exhibited abnormal distributions of polysaccharide particles, plasmolysis, and cytoplasmic content degradation accompanied by plasmalemma disruption. There were no changes in the MIC of PB in the presence of sorbitol. However, the MIC values of PB were increased by 4-fold with exogenous ergosterol. At 4 h and 8 h, PB increased nucleotide leakage. Besides, ergosterol content in T. rubrum membrane treated with PB at 0.5 × MIC , 1 × MIC , and 2 × MIC was decreased by 9.58%, 15.31%, and 76.24%, respectively. There was a dose-dependent decrease in the squalene epoxidase (SE) activity. And the reduction in the sterol 14α-demethylase P450 (CYP51) activity was achieved after PB treatments at 1 × MIC and 2 × MIC . These results suggest that PB displays nonspecific action on the cell wall. The membrane damaging effects of PB were attributed to binding with ergosterol to increase membrane permeability and interfering ergosterol biosynthesis involved with the reduction of SE and CYP51 activities. Further study is needed to develop PB as a natural antifungal candidate for clinical use.

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“…In our study, the repressed tendency found in a gene ( ERG2, ERG3, ERG4 ) encoding ergosterol biosynthesis was downregulated by 2.62-, 3.57-, and 2.71-fold, respectively. Previous research reported that ERG3 gene downregulation caused P. digitatum cells to lose the capacity to convert lanosterol to ergosterol ( 61 ).…”

Section: Discussionmentioning

confidence: 99%

Mining RNA-Seq Data to Depict How Penicillium digitatum Shapes Its Transcriptome in Response to Nanoemulsion

et al. 2021

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Penicillium digitatum is the most severe pathogen that infects citrus fruits during storage. It can cause fruit rot and bring significant economic losses. The continuous use of fungicides has resulted in the emergence of drug-resistant strains. Consequently, there is a need to develop naturally and efficiently antifungal fungicides. Natural antimicrobial agents such as clove oil, cinnamon oil, and thyme oil can be extracted from different plant parts. They exhibited broad-spectrum antimicrobial properties and have great potential in the food industry. Here, we exploit a novel cinnamaldehyde (CA), eugenol (EUG), or carvacrol (CAR) combination antifungal therapy and formulate it into nanoemulsion form to overcome lower solubility and instability of essential oil. In this study, the antifungal activity evaluation and transcriptional profile of Penicillium digitatum exposed to compound nanoemulsion were evaluated. Results showed that compound nanoemulsion had a striking inhibitory effect on P. digitatum in a dose-dependent manner. According to RNA-seq analysis, there were 2,169 differentially expressed genes (DEGs) between control and nanoemulsion-treated samples, including 1,028 downregulated and 1,141 upregulated genes. Gene Ontology (GO) analysis indicated that the DEGs were mainly involved in intracellular organelle parts of cell component: cellular respiration, proton transmembrane transport of biological process, and guanyl nucleotide-binding molecular function. KEGG analysis revealed that metabolic pathway, biosynthesis of secondary metabolites, and glyoxylate and dicarboxylate metabolism were the most highly enriched pathways for these DEGs. Taken together, we can conclude the promising antifungal activity of nanoemulsion with multiple action sites against P. digitatum. These outcomes would deepen our knowledge of the inhibitory mechanism from molecular aspects and exploit naturally, efficiently, and harmlessly antifungal agents in the citrus postharvest industry.

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Citronellal Exerts Its Antifungal Activity by Targeting Ergosterol Biosynthesis in Penicillium digitatum

Cited by 40 publications

References 40 publications

Antifungal activity of poly(ε-caprolactone) nanoparticles incorporated with Eucalyptus essential oils against Hemileia vastatrix

Antifungal activity of poly(ε-caprolactone) nanoparticles incorporated with Eucalyptus essential oils against Hemileia vastatrix

Isoflavaspidic Acid PB Extracted from Dryopteris fragrans (L.) Schott Inhibits Trichophyton rubrum Growth via Membrane Permeability Alternation and Ergosterol Biosynthesis Disruption

Mining RNA-Seq Data to Depict How Penicillium digitatum Shapes Its Transcriptome in Response to Nanoemulsion

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