The antifungal strobilurins and their possible ecological role

1995 ◽  
Vol 73 (S1) ◽  
pp. 940-945 ◽  
Author(s):  
T. Anke
Keyword(s):  
Antifungal Activity ◽  
Key Words ◽  
Phytopathogenic Fungi ◽  
Ecological Role ◽  
Natural Substrate ◽  
Lead Compounds ◽  
Low Toxicity ◽  
Respiration Inhibitors ◽  
Nutrient Resources ◽  
High Antifungal Activity

The strobilurins and the closely related oudemansins are new respiration inhibitors, binding to the Qp centre of cytochrome b. Their high antifungal activity against phytopathogenic fungi and their low toxicity towards mammals make them attractive lead compounds for the synthesis of agricultural fungicides. The strobilurins have been isolated from a great number of Basidiomycetes belonging to the genera Strobilurus, Oudemansiella, Xerula, Hydropus, Mycena, Filoboletus, Crepidotus, and Cyphellopsis as well as one Ascomycete, Bolinea lutea. Strobilurin-producing species occur in Europe, the Americas, Africa, and Australia. Most of the producing fungi grow on wood. Since under sterile conditions strobilurin production could be detected in the natural substrate it appears that the strobilurins play a role in securing nutrient resources for the producers from competing fungi. Key words: strobilurins, oudemansins, antibiotics, antifungal, Basidiomycetes.

Discovery of novel obovatol-based phenazine analogs as potential antifungal agents: synthesis and biological evaluation in vitro

2021 ◽  
Vol 76 (3-4) ◽  
pp. 173-179
Author(s):  
Chun Yang ◽  
Lili Song ◽  
Zhong Miao ◽  
Lingyun Jiang ◽  
Ting Li ◽  
...  
Keyword(s):  
Antifungal Activity ◽  
Spore Germination ◽  
Plant Secondary Metabolites ◽  
Biological Evaluation ◽  
Phytopathogenic Fungi ◽  
Lead Compounds ◽  
Magnolia Obovata ◽  
Synthesis And Biological Evaluation ◽  
Positive Controls

Abstract To explore candidate fungicides from plant secondary metabolites, 16 novel obovatol-type phenazine derivatives were semi-synthesized from obovatol isolated from the leaves of Magnolia obovata Thunb. The antifungal activity of synthesized compounds was investigated in vitro against four phytopathogenic fungi using the spore germination method. The bioassay results showed that eight derivatives (8b, 8g, 8h–k, 8i′, and 8k′) exhibited better antifungal activity against Fusarium solani than two positive controls, especially compounds 8b (IC50 = 64.61 μg mL−1) and 8i′ (IC50 = 79.97 μg mL−1) showed pronounced inhibition of spore germination activity against F. solani. They could be used as lead compounds for further structural optimization. Additionally, the preliminary structure-activity relationships (SARs) illustrated that the introduction of a benzene ring monosubstituted with electron-withdrawing groups into the obovatol scaffold could lead to potentially antifungal compounds.

scholarly journals Antifungal Activity and Phytotoxicity of Vitex simplicifolia Oliv. Leaves Essential Oil

2018 ◽  
Vol 10 (11) ◽  
pp. 203
Author(s):  
Issa Gamsore ◽  
Lassina Ouattara ◽  
Paulin Ouoba ◽  
Schémaeza Bonzi ◽  
Irénée Somda
Keyword(s):  
Antifungal Activity ◽  
Essential Oil ◽  
Growth Parameters ◽  
Phytopathogenic Fungi ◽  
Curvularia Lunata ◽  
Colletotrichum Graminicola ◽  
Inhibition Rate ◽  
Significant Difference ◽  
High Antifungal Activity ◽  
Sensitive Fungus

Agriculture faces many difficulties related to phytopathogenic fungi leading to quantitative and qualitative losses of crops. The use of essential oils against these fungi is one of the alternatives. This study focused on the antifungal activity and phytotoxicity of Vitex simplicifolia Oliv. leaves essential oil. Firstly, we extracted the essential oil from the leaves by hydrodistillation. Subsequently, seven fungal isolates were evaluated for their sensitivity to the essential oil on Potato Dextrose Agar (PDA) media at 0.1; 0.25 and 0.50%. Evaluation of the phytotoxicity of the essential oil was performed on sorghum seeds on a sterilized sand substrate. At the seventh day after incubation, the most sensitive fungi to the essential oil are Fusarium moniliforme, Colletotrichum graminicola and Curvularia lunata. The most sensitive fungus to the essential oil at 0.50% is Colletotrichum graminicola with 77.21% inhibition rate at the seventh day after incubation. Phytotoxicity evaluation showed that for all biomass parameters measured there is no significant difference between treatment with the essential oil and treatment with the fungicide control. At the end of this study, it appears that Vitex simplicifolia essential oil has a high antifungal activity. This essential oil has not shown toxicity on sorghum growth parameters. Therefore, this oil can be used in organic farming.

Antifungal Activity Directed Toward the Cell Wall by 2-Cyclohexylidenhydrazo- 4-Phenyl-Thiazole Against Candida albicans

2019 ◽  
Vol 19 (4) ◽  
pp. 428-438 ◽  
Author(s):  
Nívea P. de Sá ◽  
Ana P. Pôssa ◽  
Pilar Perez ◽  
Jaqueline M.S. Ferreira ◽  
Nayara C. Fonseca ◽  
...  
Keyword(s):  
Cell Wall ◽  
Candida Albicans ◽  
Antifungal Activity ◽  
Mammalian Cells ◽  
C Elegans ◽  
Buccal Epithelial Cells ◽  
Mutant Strains ◽  
Low Toxicity ◽  
High Concentrations ◽  
Mic Value

<p>Background: The increasing incidence of invasive forms of candidiasis and resistance to antifungal therapy leads us to seek new and more effective antifungal compounds. </P><P> Objective: To investigate the antifungal activity and toxicity as well as to evaluate the potential targets of 2- cyclohexylidenhydrazo-4-phenyl-thiazole (CPT) in Candida albicans. </P><P> Methods: The antifungal activity of CPT against the survival of C. albicans was investigated in Caenorhabditis elegans. Additionally, we determined the effect of CPT on the inhibition of C. albicans adhesion capacity to buccal epithelial cells (BECs), the toxicity of CPT in mammalian cells, and the potential targets of CPT in C. albicans. </P><P> Results: CPT exhibited a minimum inhibitory concentration (MIC) value of 0.4-1.9 µg/mL. Furthermore, CPT at high concentrations (>60 x MIC) showed no or low toxicity in HepG2 cells and <1% haemolysis in human erythrocytes. In addition, CPT decreased the adhesion capacity of yeasts to the BECs and prolonged the survival of C. elegans infected with C. albicans. Analysis of CPT-treated cells showed that their cell wall was thinner than that of untreated cells, especially the glucan layer. We found that there was a significantly lower quantity of 1,3-β-D-glucan present in CPT-treated cells than that in untreated cells. Assays performed on several mutant strains showed that the MIC value of CPT was high for its antifungal activity on yeasts with defective 1,3-β-glucan synthase. </P><P> Conclusion: In conclusion, CPT appears to target the cell wall of C. albicans, exhibits low toxicity in mammalian cells, and prolongs the survival of C. elegans infected with C. albicans.</p>

Antifúngicos poliénicos. Mecanismo de acción y aplicaciones

2020 ◽  
Vol 63 (2) ◽  
pp. 7-17
Author(s):  
Evelyn Rivera-Toledo ◽  
Alan Uriel Jiménez-Delgadillo ◽  
Patricia Manzano-Gayosso
Keyword(s):  
Antifungal Activity ◽  
Key Words ◽  
Secondary Metabolism ◽  
Amphotericin B ◽  
Antifungal Agents ◽  
Fungal Infections ◽  
Variable Number ◽  
Therapeutic Failure ◽  
Morbidity And Mortality ◽  
Clinical Use

The first compounds with specific antifungal activity were identified in the middle of the last century as a product of the secondary metabolism of bacteria of the order Actinomycetales, and their clinical use significantly diminished the morbidity and mortality associated with severe fungal infections. Many of such biosynthetic compounds are characterized by a chemical polygenic structure, with a variable number of carbon-carbon double bonds. Currently, besides polygenic antimycotics, there are other antifungal agents, such as the azole compounds, that have less toxicity in patients; however, cases of therapeutic failure with such compounds have been documented, therefore, the use of polygenics is still the best alternative in such cases. This review presents data about the properties and applications of antifungal-polygenic compounds using amphotericin B as a model. Key words: Amphotericin B; antifungal polyenes; ergosterol

scholarly journals The newly synthesized thiazole derivatives as potential antifungal compounds against Candida albicans

2021 ◽  
Author(s):  
Anna Biernasiuk ◽  
Anna Berecka-Rycerz ◽  
Anna Gumieniczek ◽  
Maria Malm ◽  
Krzysztof Z. Łączkowski ◽  
...  
Keyword(s):  
Cell Wall ◽  
Candida Albicans ◽  
Antifungal Activity ◽  
Cell Membrane ◽  
Mode Of Action ◽  
Thiazole Derivatives ◽  
Fungal Cell ◽  
Erythrocyte Lysis ◽  
Low Cytotoxicity ◽  
High Antifungal Activity

Abstract Recently, the occurrence of candidiasis has increased dramatically, especially in immunocompromised patients. Additionally, their treatment is often ineffective due to the resistance of yeasts to antimycotics. Therefore, there is a need to search for new antifungals. A series of nine newly synthesized thiazole derivatives containing the cyclopropane system, showing promising activity against Candida spp., has been further investigated. We decided to verify their antifungal activity towards clinical Candida albicans isolated from the oral cavity of patients with hematological malignancies and investigate the mode of action on fungal cell, the effect of combination with the selected antimycotics, toxicity to erythrocytes, and lipophilicity. These studies were performed by the broth microdilution method, test with sorbitol and ergosterol, checkerboard technique, erythrocyte lysis assay, and reversed phase thin-layer chromatography, respectively. All derivatives showed very strong activity (similar and even higher than nystatin) against all C. albicans isolates with minimal inhibitory concentration (MIC) = 0.008–7.81 µg/mL Their mechanism of action may be related to action within the fungal cell wall structure and/or within the cell membrane. The interactions between the derivatives and the selected antimycotics (nystatin, chlorhexidine, and thymol) showed additive effect only in the case of combination some of them and thymol. The erythrocyte lysis assay confirmed the low cytotoxicity of these compounds as compared to nystatin. The high lipophilicity of the derivatives was related with their high antifungal activity. The present studies confirm that the studied thiazole derivatives containing the cyclopropane system appear to be a very promising group of compounds in treatment of infections caused by C. albicans. However, this requires further studies in vivo. Key points • The newly thiazoles showed high antifungal activity and some of them — additive effect in combination with thymol. • Their mode of action may be related with the influence on the structure of the fungal cell wall and/or the cell membrane. • The low cytotoxicity against erythrocytes and high lipophilicity of these derivatives are their additional good properties. Graphical abstract

scholarly journals Antifungal Activity of Chemical Constituents from Piper pesaresanum C. DC. and Derivatives against Phytopathogen Fungi of Cocoa

Molecules ◽  
2021 ◽  
Vol 26 (11) ◽  
pp. 3256
Author(s):  
Luis C. Chitiva-Chitiva ◽  
Cristóbal Ladino-Vargas ◽  
Luis E. Cuca-Suárez ◽  
Juliet A. Prieto-Rodríguez ◽  
Oscar J. Patiño-Ladino
Keyword(s):  
Antifungal Activity ◽  
Benzoic Acid ◽  
Chemical Constituents ◽  
Chemical Study ◽  
Positive Control ◽  
Positive Influence ◽  
Phytopathogenic Fungi ◽  
Phytochemical Study ◽  
Benzoic Acid Derivatives ◽  
First Time

In this study, the antifungal potential of chemical constituents from Piper pesaresanum and some synthesized derivatives was determined against three phytopathogenic fungi associated with the cocoa crop. The methodology included the phytochemical study on the aerial part of P. pesaresanum, the synthesis of some derivatives and the evaluation of the antifungal activity against the fungi Moniliophthora roreri, Fusarium solani and Phytophthora sp. The chemical study allowed the isolation of three benzoic acid derivatives (1–3), one dihydrochalcone (4) and a mixture of sterols (5–7). Seven derivatives (8–14) were synthesized from the main constituents, of which compounds 9, 10, 12 and 14 are reported for the first time. Benzoic acid derivatives showed strong antifungal activity against M. roreri, of which 11 (3.0 ± 0.8 µM) was the most active compound with an IC50 lower compared with positive control Mancozeb® (4.9 ± 0.4 µM). Dihydrochalcones and acid derivatives were active against F. solani and Phytophthora sp., of which 3 (32.5 ± 3.3 µM) and 4 (26.7 ± 5.3 µM) were the most active compounds, respectively. The preliminary structure–activity relationship allowed us to establish that prenylated chains and the carboxyl group are important in the antifungal activity of benzoic acid derivatives. Likewise, a positive influence of the carbonyl group on the antifungal activity for dihydrochalcones was deduced.

scholarly journals Protective Antifungal Activity of Plantago major Extract Against the Phytopathogenic Fungi Phytophthora cinnamomi, Diplodia corticola and Colletotrichum Species

Proceedings ◽  
2020 ◽  
Vol 70 (1) ◽  
pp. 94
Author(s):  
Cláudia Ferreira ◽  
Rui Oliveira
Keyword(s):  
Antifungal Activity ◽  
Secondary Metabolites ◽  
Plant Extracts ◽  
Phytophthora Cinnamomi ◽  
Fungal Infections ◽  
Petri Dish ◽  
Phytopathogenic Fungi ◽  
Colletotrichum Acutatum ◽  
Lower Probability ◽  
Plantago Major

Synthetic fungicides for crops protection raise environmental and human concerns due to accumulation in edible vegetables, showing significant toxicity to humans, and in soil, groundwater and rivers, affecting ecological balance. In addition, they are prone to the development of resistant strains because of the single target-based mechanism of action. Plant extracts provide attractive alternatives, as they constitute a rich source of biodegradable secondary metabolites, such as phenols, flavonoids and saponins, which have multiple modes of antifungal action and a lower probability of the development of resistant fungi. This work has the objective of identifying plant extracts with antifungal activity, aiming to contribute to food safety and sustainable agricultural practices. We selected a saponin-containing plant, Plantago major, and extracted secondary metabolites with 50% (v/v) ethanol, dried by evaporation, and dissolved in water. For antifungal activity, the phytopathogenic fungi Colletotrichum acutatum, Colletotrichum gloeosporioides, Colletotrichum godetiae, Colletotrichum nymphaeae, Diplodia corticola and Phytophthora cinnamomi were selected because they affect fruits and vegetables, such as strawberry, almond, apple, avocado, blueberry and chestnut trees. The aqueous extract was incorporated into PDA medium at different concentrations and mycelial discs were placed in the center of each Petri dish. Growth was measured as the radial mycelial growth at 3, 6, and 9 days incubation at 25 °C in the dark. The maximum growth inhibition (32.2%) was obtained against P. cinnamomi with 2000 µg/mL extract followed by C. gloeosporioides (25.7%) on the sixth day and by C. godetiae and C. nymphaeae (21.1%) on the ninth day. Results show that P. major presents antifungal activity in all phytopathogenic fungi tested and the extract can be used to protect important crops, by inhibiting the development of fungal infections and promoting food security and a sustainable agriculture.

N-(5-Amino-9H-benzo[a]phenoxazin-9-ylidene)propan-1-aminium chlorides as antifungal agents and NIR fluorescence probes

2021 ◽  
Author(s):  
Rui P. C. L. Sousa ◽  
João C. C. Ferreira ◽  
Maria João Sousa ◽  
M Sameiro Sameiro T T Gonçalves
Keyword(s):  
Antifungal Activity ◽  
Antifungal Agents ◽  
Nile Blue ◽  
Fluorescence Probes ◽  
Cell Labelling ◽  
Nir Fluorescence ◽  
High Antifungal Activity

The search for benzo[a]phenoxazines, Nile Blue derivatives, with high antifungal activity and cell labelling capacity based on our previously published works in this type of compounds, led us to the...

scholarly journals Activity of Alkanediol Alkanoates against Pathogenic Plant Fungi Rhizoctonia solani and Sclerotium rolfsii

2012 ◽  
Vol 7 (9) ◽  
pp. 1934578X1200700 ◽  
Author(s):  
Paraj Shukla ◽  
Suresh Walia ◽  
Vivek Ahluwalia ◽  
Balraj S. Parmar ◽  
Muraleedharan G. Nair
Keyword(s):  
Antifungal Activity ◽  
Ethylene Glycol ◽  
Rhizoctonia Solani ◽  
Diethylene Glycol ◽  
Sclerotium Rolfsii ◽  
Phytopathogenic Fungi ◽  
Dependent Manner ◽  
Acyl Chlorides ◽  
Mass Spectral ◽  
Dose Dependent

Thirty known dialkanoates of ethylene, propylene and diethylene glycols were synthesized by reacting the glycols with acyl chlorides and their structures confirmed by IR, NMR and mass spectral analyses. They exhibited significant antifungal activity against two phytopathogenic fungi Rhizoctonia solani Kuehn and Sclerotium rolfsii Sacc in a dose dependent manner. Propylene glycol dipentanoate was the most active against R. solani. followed by diethylene glycol dibutanoate and ethylene glycol dibutanoate. Against S. rolfsii ethylene glycol diheptanoate was found to be most active followed by diethylene glycol diisobutanoate As compared to the standard reference benomyl (EC50 5.16 μg/mL), the potential alkanediol dialkanoates showed EC50 in the range of 33 – 60 μg/mL.

scholarly journals In Vitro Antifungal Activity of Sanguinarine and Chelerythrine Derivatives against Phytopathogenic Fungi

Molecules ◽  
2012 ◽  
Vol 17 (11) ◽  
pp. 13026-13035 ◽  
Author(s):  
Xin-Juan Yang ◽  
Fang Miao ◽  
Yao Yao ◽  
Fang-Jun Cao ◽  
Rui Yang ◽  
...  
Keyword(s):  
Antifungal Activity ◽  
Phytopathogenic Fungi ◽  
Sanguinarine And Chelerythrine ◽  
In Vitro Antifungal Activity
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