scholarly journals Synthesis, Fungitoxic Activity against Botrytis cinerea and Phytotoxicity of Alkoxyclovanols and Alkoxyisocaryolanols

2021 ◽  
Vol 7 (12) ◽  
pp. 1079
Author(s):  
Adriana de Almeida Pinto Bracarense ◽  
Jociani Ascari ◽  
Giovanni Gontijo de Souza ◽  
Thays Silva Oliveira ◽  
Antonio Ruano-González ◽  
...  
Keyword(s):  
Antifungal Activity ◽  
Botrytis Cinerea ◽  
Phytopathogenic Fungus ◽  
General Terms ◽  
Structure Activity ◽  
Antifungal Effects ◽  
Phytotoxic Effect ◽  
First Time ◽  
Further Development ◽  
Model Crop

Clovane and isocaryolane derivatives have been proven to show several levels of activity against the phytopathogenic fungus Botrytis cinerea. Both classes of sesquiterpenes are reminiscent of biosynthetic intermediates of botrydial, a virulence factor of B. cinerea. Further development of both classes of antifungal agent requires exploration of the structure–activity relationships for the antifungal effects on B. cinerea and phytotoxic effects on a model crop. In this paper, we report on the preparation of a series of alkoxy-clovane and -isocaryolane derivatives, some of them described here for the first time (2b, 2d, 2f–2h, and 4c–4e); the evaluation of their antifungal properties against B. cinerea, and their phytotoxic activites on the germination of seeds and the growth of radicles and shoots of Lactuca sativa (lettuce). Both classes of compound show a correlation of antifungal activity with the nature of side chains, with the best activity against B. cinerea for 2d, 2h, 4c and 4d. In general terms, while 2-alkoxyclovan-9-ols (2a–2e) exert a general phytotoxic effect, this is not the case for 2-arylalkoxyclovan-9-ols (2f–2i) and 8-alkoxyisocaryolan-9-ols (4a–4d), where stimulating effects would make them suitable candidates for application to plants.

scholarly journals Biocatalytic Preparation of Chloroindanol Derivatives. Antifungal Activity and Detoxification by the Phytopathogenic Fungus Botrytis cinerea

Plants ◽  
2020 ◽  
Vol 9 (12) ◽  
pp. 1648
Author(s):  
Cristina Pinedo-Rivilla ◽  
Javier Moraga ◽  
Guillermo Pérez-Sasián ◽  
Alba Peña-Hernández ◽  
Isidro G. Collado ◽  
...  
Keyword(s):  
Antifungal Activity ◽  
Botrytis Cinerea ◽  
Chemical Compounds ◽  
Phytopathogenic Fungus ◽  
Spectroscopic Techniques ◽  
Oxidation Reactions ◽  
Enantiomerically Pure ◽  
Chromatographic Techniques ◽  
Detoxification Mechanism ◽  
First Time

Indanols are a family of chemical compounds that have been widely studied due to their broad range of biological activity. They are also important intermediates used as synthetic precursors to other products with important applications in pharmacology. Enantiomerically pure chloroindanol derivatives exhibiting antifungal activity against the phytopathogenic fungus Botrytis cinerea were prepared using biocatalytic methods. As a result of the biotransformation of racemic 6-chloroindanol (1) and 5-chloroindanol (2) by the fungus B. cinerea, the compounds anti-(+)-6-chloroindan-1,2-diol (anti-(+)-7), anti-(+)-5-chloroindan-1,3-diol (anti-(+)-8), syn-(+)-5-chloroindan-1,3-diol (syn-(+)-8), syn-(-)-5-chloroindan-1,3-diol (syn-(-)-8), and anti-(+)-5-chloroindan-1,2-diol (anti-(+)-9) were isolated for the first time. These products were characterized by spectroscopic techniques and their enantiomeric excesses studied by chromatographic techniques. The results obtained in the biotransformation seem to suggest that the fungus B. cinerea uses oxidation reactions as a detoxification mechanism.

scholarly journals The Search for Quorum Sensing in Botrytis cinerea: Regulatory Activity of Its Extracts on Its Development

Plants ◽  
2020 ◽  
Vol 9 (2) ◽  
pp. 168
Author(s):  
Esteban D. Rosero-Hernández ◽  
Fernando L. Echeverri
Keyword(s):  
Quorum Sensing ◽  
Botrytis Cinerea ◽  
Biological Activities ◽  
Phytopathogenic Fungus ◽  
Effective Strategies ◽  
Promising Strategy ◽  
Phytotoxic Effect ◽  
Large Crop ◽  
Germ Tubes ◽  
Great Inhibition

Botrytis cinerea is a phytopathogenic fungus that causes large crop and post-harvest losses. Therefore, new and effective strategies are needed to control the disease and to reduce resistance to fungicides. Modulating pathogenicity and virulence by manipulating microbial communication is a promising strategy. This communication mechanism, called Quorum Sensing (QS), has already been reported in bacteria and yeasts; however, it has not yet been studied in B. cinerea. To establish the existence of this biochemical process in B. cinerea, we prepared extracts at different growth times (D1-D12), which were applied to fresh cultures of the same fungi. The chemical analysis of the extracts obtained from several fermentations showed different compositions and biological activities. We confirmed the presence of several phytotoxins, as well as compounds 1-phenylethanol and 3-phenylpropanol. Day five extract (0.1%) inhibited conidia germination and elongation of germ tubes, day seven extract (1%) produced the greatest phytotoxic effect in tomato leaves, and day nine extract (0.1%) was a sporulation inhibitor. In contrast, the extracts from days 7, 9, and 12 of fermentation (0.1% and 0.01%) promoted pellet and biofilm formation. Sporulation was slightly induced at 0.01%, while at 0.1% there was a great inhibition. At the highest extract concentrations, a biocidal effect was detected, but at the lowest, we observed a QS-like effect, regulating processes such as filamentation, morphogenesis, and pathogenesis. These results of the biological activity and composition of extracts suggest the existence of a QS-like mechanism in B. cinerea, which could lead to new non-biocidal alternatives for its control through interference in the pathogenicity and virulence mechanisms of the fungi.

Comparative analysis of Botrytis cinerea in response to the microbial secondary metabolite benzothiazole using iTRAQ-based quantitative proteomics

2020 ◽  
Author(s):  
Kaidi Cui ◽  
Leiming He ◽  
Yunhe Zhao ◽  
Wei Mu ◽  
Jin Lin ◽  
...  
Keyword(s):  
Antifungal Activity ◽  
Botrytis Cinerea ◽  
Mitochondrial Membrane ◽  
Molecular Mechanisms ◽  
Glyoxylate Cycle ◽  
Pathogenic Fungi ◽  
Phytopathogenic Fungus ◽  
Future Research ◽  
Design And Synthesis ◽  
The Glyoxylate Cycle

Benzothiazole is a microbial volatile compound with strong antifungal activity against the phytopathogenic fungus Botrytis cinerea, but its mode of action against fungi remains largely unknown. Understanding the molecular mechanisms underlying its activity could aid the design and synthesis of new similar compounds against pathogenic fungi. Based on the results of morphological and antifungal activity assays, B. cinerea was exposed to 2.5 μL/L benzothiazole for 12, 24 and 48 h, and an iTRAQ-based quantitative proteomic analysis showed that 378 out of 5,110 identified proteins were differentially expressed proteins (DEPs). The majority of these DEPs were associated with carbohydrate metabolism, oxidation-reduction processes and energy production. Further analysis showed that benzothiazole inhibited mitochondrial membrane organization and decreased the mitochondrial membrane potential of B. cinerea. In addition, the key enzymes of the glyoxylate cycle were downregulated after benzothiazole treatment, and a biochemical analysis indicated that the inhibition of the glyoxylate cycle by benzothiazole blocked nutrient availability and interfered with ATP generation. This study provides markers for future research of the molecular responses of B. cinerea to benzothiazole stress.

scholarly journals Endophytic Fungi Isolated from Plants Growing in Central Andean Precordillera of Chile with Antifungal Activity against Botrytis cinerea

2020 ◽  
Vol 6 (3) ◽  
pp. 149
Author(s):  
Araceli Vidal ◽  
Rodolfo Parada ◽  
Leonora Mendoza ◽  
Milena Cotoras
Keyword(s):  
Antifungal Activity ◽  
Volatile Compounds ◽  
Botrytis Cinerea ◽  
Endophytic Fungi ◽  
Mycelial Growth ◽  
Pathogenic Fungus ◽  
Fruit Production ◽  
Phytopathogenic Fungus ◽  
Endemic Plants ◽  
The World

Botrytis cinerea is an important phytopathogenic fungus affecting the fruit production around the world. This fungus is controlled mainly by using synthetic fungicides, but many resistant isolates have been selected by the indiscriminate use of fungicides. Endophytic fungi or secondary metabolites obtained from them become an alternative method of control for this fungus. The aim of this work was to identify endophytic fungi with antifungal activity against the plant pathogenic fungus B. cinerea isolated from plants from Central Andean Precordillera of Chile. Three endophytic fungi (Ac1, Lc1 and Ec1) with antifungal activity against B. cinerea were isolated from native and endemic plants growing in Central Andean Precordillera of Chile. The isolates Lc1 (isolated from Lithraea caustica) and Ac1 (isolated from Acacia caven) were identified as Alternaria spp. and the isolate Ec1 (isolated from Echinopsis chiloensis) was identified as Aureobasidium spp. The isolated endophytic fungi would inhibit B. cinerea through the secretion of diffusible and volatile compounds affecting the mycelial growth, conidia germination and interestingly, it was also shown that the volatile compounds produced by the three isolated endophytic fungi suppressed the sporulation of B. cinerea.

scholarly journals Antifungal Methylphenone Derivatives and 5-Methylcoumarins from Mutisia friesiana

2003 ◽  
Vol 58 (7-8) ◽  
pp. 533-540 ◽  
Author(s):  
Carmen I. Viturro ◽  
Juana R. de la Fuente ◽  
Marta S. Maier
Keyword(s):  
Antifungal Activity ◽  
Phytopathogenic Fungus ◽  
Spectroscopic Methods ◽  
Cladosporium Cucumerinum ◽  
Aerial Parts ◽  
Nmr Data ◽  
First Time ◽  
C Nmr

Abstract In addition to the known mutisicoumarin A, the aerial parts of the shrub Mutisia friesiana afforded five new methylphenones, two new 5-methylcoumarins and a new related chromone. Their structures were elucidated by spectroscopic methods. 13C NMR data for mutisicoumarin A are reported for the first time. Mutisiphenones A and B and mutisicoumarin A showed antifungal activity against the phytopathogenic fungus Cladosporium cucumerinum.

Phenolic Imidazole Derivatives with Dual Antioxidant/Antifungal Activity: Synthesis and Structure-Activity Relationship

2019 ◽  
Vol 15 (4) ◽  
pp. 341-351 ◽  
Author(s):  
Ana P. Bettencourt ◽  
Marián Castro ◽  
João P. Silva ◽  
Francisco Fernandes ◽  
Olga P. Coutinho ◽  
...  
Keyword(s):  
Antioxidant Activity ◽  
Antifungal Activity ◽  
Organic Molecules ◽  
Inhibitory Concentration ◽  
Yeast Species ◽  
Dpph Radical ◽  
Dpph Assay ◽  
Gram Negative ◽  
Structure Activity ◽  
Deoxyribose Degradation

Background: Previous publications show that the addition of a phenolic antioxidant to an antifungal agent, considerably enhances the antifungal activity. Objective: Synthesis of novel compounds combining phenolic units with linear or cyclic nitrogencontaining organic molecules with antioxidant/antifungal activity using methodologies previously developed in the group. Methods: Several N- [1,2-dicyano-2- (arylidenamino) vinyl]-O-alkylformamidoximes 3 were synthesized and cyclized to 4,5-dicyano-N- (N´-alcoxyformimidoyl)-2-arylimidazoles 4 upon reflux in DMF, in the presence of manganese dioxide or to 6-cyano-8-arylpurines 5 when the reagent was refluxed in acetonitrile with an excess of triethylamine. These compounds were tested for their antioxidant activity by cyclic voltammetry, DPPH radical (DPPH•) assay and deoxyribose degradation assay. The minimum inhibitory concentration (MIC) of all compounds was evaluated against two yeast species, Saccharomyces cerevisiae and Candida albicans, and against bacteria Bacillus subtilis (Gram-positive) and Escherichia coli (Gram negative). Their cytotoxicity was evaluated in fibroblasts. Results: Among the synthetised compounds, five presented higher antioxidant activity than reference antioxidant Trolox and from these compounds, four presented antifungal activity without toxic effects in fibroblasts and bacteria. Conclusion: Four novel compounds presented dual antioxidant/antifungal activity at concentrations that are not toxic to bacteria and fibroblasts. The active molecules can be used as an inspiration for further studies in this area.

Chemical composition and antifungal activity of essential oils and their combinations against Botrytis cinerea in strawberries

2021 ◽  
Author(s):  
Josemar Gonçalves de Oliveira Filho ◽  
Guilherme da Cruz Silva ◽  
Aline Cristina de Aguiar ◽  
Lavinia Cipriano ◽  
Henriette Monteiro Cordeiro de Azeredo ◽  
...  
Keyword(s):  
Chemical Composition ◽  
Antifungal Activity ◽  
Essential Oils ◽  
Botrytis Cinerea

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.

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