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1.
Molecules ; 29(15)2024 Jul 26.
Artigo em Inglês | MEDLINE | ID: mdl-39124920

RESUMO

Here, we report for the first time on the mechanisms of action of the essential oil of Ruta graveolens (REO) against the plant pathogen Colletotrichum gloeosporioides. In particular, the presence of REO drastically affected the morphology of hyphae by inducing changes in the cytoplasmic membrane, such as depolarization and changes in the fatty acid profile where straight-chain fatty acids (SCFAs) increased by up to 92.1%. In addition, REO induced changes in fungal metabolism and triggered apoptosis-like responses to cell death, such as DNA fragmentation and the accumulation of reactive oxygen species (ROS). The production of essential enzymes involved in fungal metabolism, such as acid phosphatase, ß-galactosidase, ß-glucosidase, and N-acetyl-ß-glucosaminidase, was significantly reduced in the presence of REO. In addition, C. gloeosporioides activated naphthol-As-BI phosphohydrolase as a mechanism of response to REO stress. The data obtained here have shown that the essential oil of Ruta graveolens has a strong antifungal effect on C. gloeosporioides. Therefore, it has the potential to be used as a surface disinfectant and as a viable replacement for fungicides commonly used to treat anthracnose in the postharvest testing phase.


Assuntos
Antifúngicos , Colletotrichum , Óleos Voláteis , Espécies Reativas de Oxigênio , Ruta , Colletotrichum/efeitos dos fármacos , Óleos Voláteis/farmacologia , Óleos Voláteis/química , Ruta/química , Antifúngicos/farmacologia , Antifúngicos/química , Espécies Reativas de Oxigênio/metabolismo , Doenças das Plantas/microbiologia , Testes de Sensibilidade Microbiana , Fragmentação do DNA/efeitos dos fármacos
2.
J Agric Food Chem ; 72(27): 15256-15264, 2024 Jul 10.
Artigo em Inglês | MEDLINE | ID: mdl-38935555

RESUMO

A study targeting novel antifungal metabolites identified potent in vitro antifungal activity against key plant pathogens in acetone extracts of Streptomyces sp. strain CA-296093. Feature-based molecular networking revealed the presence in this extract of antimycin-related compounds, leading to the isolation of four new compounds: escuzarmycins A-D (1-4). Extensive structural elucidation, employing 1D and 2D NMR, high-resolution mass spectrometry, Marfey's analysis, and NOESY correlations, confirmed their structures. The bioactivity of these compounds was tested against six fungal phytopathogens, and compounds 3 and 4 demonstrated strong efficacy, particularly against Zymoseptoria tritici, with compound 3 exhibiting the highest potency (EC50: 11 nM). Both compounds also displayed significant antifungal activity against Botrytis cinerea and Colletotrichum acutatum, with compound 4 proving to be the most potent. Despite moderate cytotoxicity against the human cancer cell line HepG2, compounds 3 and 4 emerge as promising fungicides for combating Septoria tritici blotch, anthracnose, and gray mold.


Assuntos
Ascomicetos , Colletotrichum , Fungicidas Industriais , Doenças das Plantas , Streptomyces , Fungicidas Industriais/farmacologia , Fungicidas Industriais/química , Doenças das Plantas/microbiologia , Doenças das Plantas/prevenção & controle , Ascomicetos/efeitos dos fármacos , Ascomicetos/química , Streptomyces/química , Streptomyces/metabolismo , Humanos , Colletotrichum/efeitos dos fármacos , Botrytis/efeitos dos fármacos , Estrutura Molecular
3.
Sci Rep ; 14(1): 11228, 2024 05 16.
Artigo em Inglês | MEDLINE | ID: mdl-38755187

RESUMO

Antimicrobial resistance in fungal pathogens (both human and plant) is increasing alarmingly, leading to massive economic crises. The existing anti-fungal agents are becoming ineffective, and the situation worsens on a logarithmic scale. Novel antifungals from unique natural sources are highly sought to cope sustainably with the situation. Metabolites from endophytic microbes are the best-fitted alternatives in this case. Endophytes are the untapped sources of 'plants' internal microbial population' and are promising sources of effective bio-therapeutic agents. Fungal endophytes were isolated from Tropaeolum majus and checked for antifungal activity against selected plant and human pathogens. Bioactive metabolites were identified through chromatographic techniques. The mode of action of those metabolites was evaluated through various spectroscopic techniques. The production of antifungal metabolite was optimized also. In particular VOCs (volatile organic compounds) of TML9 were tested in vitro for their anti-phytopathogenic activity. Ethyl acetate (EA) extract of cell-free culture components of Colletotrichum aenigma TML3 exhibited broad-spectrum antifungal activity against four species of Candida and the major constituents reported were 6-pentyl-2H-pyran-2-one, 2-Nonanone, 1 propanol 2-amino. The volatile metabolites, trans-ocimene, geraniol, and 4-terpinyl acetate, produced from Curvularia lunata TML9, inhibited the growth of some selected phyto pathogens. EA extract hampered the biofilm formation, minimised the haemolytic effect, and blocked the transformation of Candida albicans (MTCC 4748) from yeast to hyphal form with a Minimum Fungicidal Concentration (MFC) of 200-600 µg mL-1. Central carbohydrate metabolism, ergosterol synthesis, and membrane permeability were adversely affected and caused the lethal leakage of necessary macromolecules of C. albicans. Volatile metabolites inhibited the growth of phytopathogens i.e., Rhizoctonia solani, Alternaria alternata, Botrytis cinerea, Cercospora beticola, Penicillium digitatum, Aspergillus fumigatus, Ceratocystis ulmi, Pythium ultimum up to 89% with an IC50 value of 21.3-69.6 µL 50 mL-1 and caused leakage of soluble proteins and other intracellular molecules. Citrusy sweet odor volatiles of TML9 cultured in wheat-husk minimised the infections of Penicillium digitatum (green mold), in VOC-exposed sweet oranges (Citrus sinensis). Volatile and non-volatile antifungal metabolites of these two T. majus endophytes hold agricultural and pharmaceutical interests. Metabolites of TML3 have strong anti-Candida activity and require further assessment for therapeutic applications. Also, volatile metabolites of TML9 can be further studied as a source of antifungals. The present investigational outcomes bio-prospects the efficacy of fungal endophytes of Garden Nasturtium.


Assuntos
Antifúngicos , Endófitos , Compostos Orgânicos Voláteis , Compostos Orgânicos Voláteis/farmacologia , Compostos Orgânicos Voláteis/química , Antifúngicos/farmacologia , Antifúngicos/química , Endófitos/metabolismo , Endófitos/química , Testes de Sensibilidade Microbiana , Colletotrichum/efeitos dos fármacos , Fungos/efeitos dos fármacos , Alternaria/efeitos dos fármacos , Rhizoctonia/efeitos dos fármacos , Humanos , Candida/efeitos dos fármacos
4.
Phytochemistry ; 222: 114078, 2024 Jun.
Artigo em Inglês | MEDLINE | ID: mdl-38574958

RESUMO

Six undescribed infrequent eremophilane derivatives including diaportheremopholins A - F and its previously undescribed side chain (E)-2-methyloct-2-enoic acid, together with three known compounds (testacein, xestodecalactones B and C), were isolated from the endophytic fungus Diaporthe sp. BCC69512. The chemical structures were determined based on NMR spectroscopic information in conjunction with the evidence from NOESY spectrum, Mosher's application, and chemical reactions for corroborating the absolute configurations. The isolated compounds were evaluated for biological properties such as antimalarial, anti-TB, anti-phytopathogenic fungal, antibacterial activities and for cytotoxicity against malignant (MCF-7 and NCI-H187) and non-malignant (Vero) cells. Diaportheremopholins B (2) and E (5) possessed broad antimicrobial activity against Mycobacterium tuberculosis, Bacillus cereus, Alternaria brassicicola and Colletotrichum acutatum with MICs in a range of 25.0-50.0 µg/mL. Testacein (7) exhibited strong anti-A. brassicicola and anti-C. acutatum activities with equal MIC values of 3.13 µg/mL. Moreover, diaportheremopholin F (6) and compound 8 displayed antitubercular activity with equal MIC values of 50.0 µg/mL. All tested compounds were non-cytotoxic against MCF-7, NCI-H187, and Vero cells, except those compounds 2 and 5-7 exhibited weak cytotoxicity against both malignant and non-malignant cells with IC50 values in a range of 15.5-115.5 µM.


Assuntos
Alternaria , Ascomicetos , Testes de Sensibilidade Microbiana , Mycobacterium tuberculosis , Humanos , Ascomicetos/química , Chlorocebus aethiops , Alternaria/química , Células Vero , Mycobacterium tuberculosis/efeitos dos fármacos , Antibacterianos/farmacologia , Antibacterianos/química , Antibacterianos/isolamento & purificação , Bacillus cereus/efeitos dos fármacos , Animais , Estrutura Molecular , Ensaios de Seleção de Medicamentos Antitumorais , Colletotrichum/efeitos dos fármacos , Antifúngicos/farmacologia , Antifúngicos/química , Antifúngicos/isolamento & purificação , Antineoplásicos/farmacologia , Antineoplásicos/química , Antineoplásicos/isolamento & purificação , Antimaláricos/farmacologia , Antimaláricos/química , Antimaláricos/isolamento & purificação , Relação Estrutura-Atividade , Células MCF-7 , Anti-Infecciosos/farmacologia , Anti-Infecciosos/química , Anti-Infecciosos/isolamento & purificação , Relação Dose-Resposta a Droga
5.
Chem Biodivers ; 18(3): e2000941, 2021 Mar.
Artigo em Inglês | MEDLINE | ID: mdl-33507621

RESUMO

The essential oil from the annual plant Lepidium virginicum L. was chemically characterized in three consecutive years (2018-2020). The essential oils were evaluated in vitro and in situ on the causal agent of anthracnose in tamarillo fruits (Solanum betaceum). The main volatile constituents were phenylacetonitrile (>60 %), linalool (>10 %), limonene (>7 %) and α-terpineol (>5 %). The essential oil (MIC, 19-30 µg mL-1 ), phenylacetonitrile (MIC, 45 µg mL-1 ) and α-terpineol (MIC, 73 µg mL-1 ) caused a significant inhibition in the conidial viability from a wild strain of Colletotrichum acutatum, which was isolated and identified as a causal agent of anthracnose. The inoculation of conidia from C. acutatum in non-symptomatic tamarillo fruits, followed by the in situ treatment with different concentrations of the essential oil (>30 µg mL-1 ), phenylacetonitrile and α-terpineol, significantly (p<0.01) avoided the degradation of anthocyanins (delphinidin 3-O-rutinoside, cyanidin 3-O-rutinoside and pelargonidin 3-O-rutinoside) and carotenoids (ß-cryptoxanthin and ß-carotene) as well as retarded yellowing and necrosis triggered by anthracnose at least for 10 days. Our results suggest the potential use of the essential oil from L. virginicum as a natural component to preserve the nutraceutical content of tamarillo fruits against C. acutatum infection.


Assuntos
Antifúngicos/farmacologia , Colletotrichum/efeitos dos fármacos , Lepidium/química , Óleos Voláteis/farmacologia , Doenças das Plantas/prevenção & controle , Substâncias Protetoras/farmacologia , Antifúngicos/química , Antifúngicos/isolamento & purificação , Suplementos Nutricionais , Frutas/química , Testes de Sensibilidade Microbiana , Óleos Voláteis/química , Óleos Voláteis/isolamento & purificação , Substâncias Protetoras/química , Substâncias Protetoras/isolamento & purificação , Solanum/química
6.
J Environ Sci Health B ; 56(1): 73-81, 2021.
Artigo em Inglês | MEDLINE | ID: mdl-33131418

RESUMO

This study aimed to determine the chemical composition of Eucalyptus staigeriana essential oil (EO) and its effect in vivo against Botrytis cinerea and Colletotrichum acutatum in postharvest of grapes and in a vineyard. Moreover, grapes collected from de field experiments were used to evaluate the impact of the alternative control on the alcoholic fermentation and wine composition. The major compounds of E. staigeriana EO were citral (30.91%), 1,8-cineole (24.59%), and limonene (19.47%). In the postharvest experiment, EO was efficient, reducing the incidence and severity of disease caused by B. cinerea and the incidence of disease caused by C. acutatum, both in preventive and curative treatment. Moreover, this EO reduced the incidence and severity of gray rot caused by B. cinerea and the severity of ripe rot caused by C. acutatum in the field. The alternative control did not significantly influence the alcoholic fermentation and volatile composition of wines, except for the residual presence of 1,8-cineole that can contribute to the aroma complexity of 'Isabella' wine. These results are promising and indicate that E. staigeriana EO might be further investigated as a natural alternative to control fungal rots on grapes.


Assuntos
Óleos Voláteis/farmacologia , Doenças das Plantas/prevenção & controle , Vitis , Botrytis/efeitos dos fármacos , Colletotrichum/efeitos dos fármacos , Eucalyptus/química , Fazendas , Microbiologia de Alimentos , Óleos Voláteis/química , Doenças das Plantas/microbiologia , Vitis/química , Vitis/microbiologia , Compostos Orgânicos Voláteis/análise , Vinho/análise
7.
Molecules ; 25(22)2020 Nov 16.
Artigo em Inglês | MEDLINE | ID: mdl-33207599

RESUMO

We investigated alpha-mangostin (α-mangostin, α-MG), a xanthone natural product extracted from the pericarp of mangosteen (Garcinia mangostana), for its antifungal activities and possible mechanism against Colletotrichum gloeosporioides, which causes mango anthracnose. The results demonstrated that α-MG had a relatively high in vitro inhibitory activity against C. gloeosporioides among 20 plant pathogenic fungi. The median effective concentration (EC50) values of α-MG against mycelial growth were nearly 10 times higher than those of spore germination inhibition for both strains of C. gloeosporioides, the carbendazim-sensitive (CBD-s) and carbendazim-resistant (CBD-r). The results suggested that α-MG exhibited a better inhibitory effect on spore germination than on the mycelial growth of C. gloeosporioides. Further investigation indicated that the protective effect could be superior to the therapeutic effect for mango leaves for scab development. The morphological observations of mycelium showed that α-MG caused the accumulation of dense bodies. Ultrastructural observation further revealed that α-MG caused a decrease in the quantity and shape of the swelling of mitochondria in the mycelium cells of C. gloeosporioides. In addition, bioassays disclosed that the inhibitory activity of α-MG on spore germination was reduced by adding exogenous adenosine triphosphate (ATP). These results suggested that the mode of action of α-MG could be involved in the destruction of mitochondrial energy metabolism. The current study supports α-MG as a natural antifungal agent in crop protection.


Assuntos
Antifúngicos/farmacologia , Colletotrichum/efeitos dos fármacos , Xantonas/farmacologia , Trifosfato de Adenosina/farmacologia , Antifúngicos/química , Colletotrichum/ultraestrutura , Testes de Sensibilidade Microbiana , Micélio/efeitos dos fármacos , Micélio/crescimento & desenvolvimento , Micélio/ultraestrutura , Folhas de Planta/química , Esporos Fúngicos/efeitos dos fármacos , Xantonas/química , Xantonas/toxicidade
8.
Molecules ; 25(19)2020 Sep 28.
Artigo em Inglês | MEDLINE | ID: mdl-32998189

RESUMO

One of the principal etiological agents associated with losses in horticultural crops is the fungus Colletotrichum sp. This study aimed to evaluate the in vitro effectiveness of the essential oil (EO) from Cymbopogon citratus in chitosan supports for the control of Colletotrichum gloeosporioides isolated from sweet pepper plants. METHODS: The extraction and phytochemical analysis of the EO of C. citratus were performed along with its encapsulation in chitosan-agar in order to compare it with other techniques and determine its effect on C. gloeosporioides. RESULTS: The EO from the citral chemotype (58%) encapsulated in the chitosan-agar, with an 83% encapsulation efficiency in mass percentage, resulted in the total inhibition of mycelial growth at a minimum inhibitory concentration of 1370 ppm. This concentration was effective in controlling the disease under greenhouse conditions. The effectivity of the capsules containing EO was superior to that of other controls using EO evaluated in vitro. The capsules demonstrated an effective period of 51 days, with an additional 30 days of effectiveness after a reinfection cycle, thus providing similar results to the control with Trichoderma sp. CONCLUSIONS: Chitosan capsules present a promising strategy in the use of C. citratus EO on C. gloeosporioides, and they are highly effective and stable under in vitro and field conditions.


Assuntos
Capsicum/microbiologia , Quitosana/química , Colletotrichum/efeitos dos fármacos , Colletotrichum/isolamento & purificação , Cymbopogon/química , Óleos Voláteis/farmacologia , Ágar/química , Antifúngicos/farmacologia , Cápsulas , Colletotrichum/patogenicidade , DNA Intergênico/genética , Testes de Sensibilidade Microbiana , Virulência/efeitos dos fármacos
9.
Plant Cell Rep ; 39(8): 1095-1107, 2020 Aug.
Artigo em Inglês | MEDLINE | ID: mdl-32399673

RESUMO

KEY MESSAGE: Overexpression of HbWRKY40 induces ROS burst in tobacco and increases disease resistance in Arabidopsis; RNA-seq and ChIP assays revealed the regulatory network of HbWRKY40 in plant defense. WRKY, a family of plant transcription factors, are involved in the regulation of numerous biological processes. In rubber tree Hevea brasiliensis, the roles of WRKYs remain poorly understood. In the present study, a total of 111 genes encoding putative HbWRKY proteins were identified in the H. brasiliensis genome. Among these genes, HbWRKY40 transcripts were significantly induced by Colletotrichum gloeosporioides and salicylic acid. To assess its roles in plant defense, HbWRKY40 was over-expressed in Nicotiana benthamiana and Arabidopsis thaliana. The results showed that HbWRKY40 significantly induced reactive oxygen species burst in N. benthamiana and increased resistance of Arabidopsis against Botrytis cinerea. Transient expression in mesophyll cell protoplasts of H. brasiliensis showed that HbWRKY40 localizes at nuclei. In addition, transcripts of 145 genes were significantly up-regulated and 6 genes were down-regulated in the protoplasts over-expressing HbWRKY40 based on the RNA-seq analysis. Among these potential downstream targets, 12 genes contain potential WRKY-binding sites at the promoter regions. Further analysis through chromatin immunoprecipitation revealed that 10 of these 12 genes were the downstream targets of HbWRKY40. Taken together, our findings indicate that HbWRKY40 plays an important role in the disease resistance by regulating defense-associated genes in H. brasiliensis.


Assuntos
Resistência à Doença , Hevea/metabolismo , Hevea/microbiologia , Doenças das Plantas/microbiologia , Proteínas de Plantas/metabolismo , Arabidopsis/genética , Botrytis/efeitos dos fármacos , Botrytis/fisiologia , Colletotrichum/efeitos dos fármacos , Colletotrichum/fisiologia , Resistência à Doença/genética , Perfilação da Expressão Gênica , Regulação da Expressão Gênica de Plantas/efeitos dos fármacos , Genes de Plantas , Hevea/efeitos dos fármacos , Hevea/genética , Peróxido de Hidrogênio/metabolismo , Filogenia , Doenças das Plantas/genética , Reguladores de Crescimento de Plantas/farmacologia , Folhas de Planta/efeitos dos fármacos , Folhas de Planta/metabolismo , Proteínas de Plantas/genética , Plantas Geneticamente Modificadas , Regiões Promotoras Genéticas/genética , Protoplastos/efeitos dos fármacos , Protoplastos/metabolismo , Espécies Reativas de Oxigênio/metabolismo , Frações Subcelulares/metabolismo , Superóxidos/metabolismo , Nicotiana/genética
10.
Food Chem ; 326: 126997, 2020 Oct 01.
Artigo em Inglês | MEDLINE | ID: mdl-32422511

RESUMO

The increased demand for pesticide-free foods has also increased the search for healthier and environmentally friendly alternatives in agriculture. Essential oils are known to possess natural antifungal properties, becoming a reliable alternative for commercial fungicides, especially for postharvest decay control. However, essential oils are volatile and photodegradable, which reduces their long-term activities. This work presents the development of a lemongrass essential oil-containing poly(lactic acid) nanocapsules. They have shown in vitro antifungal activity against Colletotrichum acutatum and Colletotrichum gloeosporioides with a MIC dosage of 0.1% (v/v) for both phytopathogens. In the in vivo assay with postharvest apples, the ones treated with encapsulated essential oil showed bitter rot lesions three times smaller than the ones treated with non-encapsulated essential oil, or in comparison to the apples in positive control. The methodology led to stable nanocapsules with spherical morphology, a mean diameter of 96.4 nm, and with an encapsulation efficiency of 99%.


Assuntos
Antifúngicos/farmacologia , Colletotrichum/efeitos dos fármacos , Cymbopogon/química , Fungicidas Industriais/farmacologia , Nanocápsulas/química , Óleos Voláteis/química , Poliésteres/farmacologia , Malus/efeitos dos fármacos , Malus/microbiologia , Poliésteres/química
11.
Int J Food Microbiol ; 326: 108649, 2020 Aug 02.
Artigo em Inglês | MEDLINE | ID: mdl-32402917

RESUMO

In this study we assessed the efficacy of chitosan (CHI) (2%) emulsion added with Ruta graveolens L. essential oil (REO) at different concentrations (0.5%, 1.0% and 1.5%) to control C. gloesporioides grows both "in situ" and "in vitro" in papaya Maradol (Carica papaya L.). In vitro studies showed a decrease on fungal growth (mycelia diameter) with the increase of REO concentration, while 0.5% of REO induce a reduction of 56.42%, REO at 1.0% and 1.5% induced a reduction of 97%. Microscopic analysis showed irreversible deleterious morphological and ultrastructural alterations as well as changes in conidia morphology, and conidia germination inhibition up to 90%. Among the most abundant REO constituents, 2-Nonanol showed strong antifungal activity followed by 2-Undecanone, Benzyl acetate, 2-Nonanone, 2-Tridecanone and 2-Dodecanone. Studies "in situ" on papaya fruit during 12 days at 20 °C, showed a reduction of the C. gloesporioides lesion expansion by 50% using CHI-REO 0.5% emulsions and by 100% with treatments of CHI-REO 1.0 and 1.5%, in addition the emulsions were efficacious to reduce the fruit surface microbiota. On the other hand, physicochemical analysis of the papaya fruits demonstrated that CHI-REO emulsions treatment delayed papaya ripening without affecting the organoleptic characteristics. All these results demonstrated for the first time the application of coatings CHI-REO as a postharvest treatment for the control of anthracnose on papaya fruit.


Assuntos
Antifúngicos/farmacologia , Carica/microbiologia , Quitosana/farmacologia , Colletotrichum/efeitos dos fármacos , Óleos Voláteis/farmacologia , Ruta/metabolismo , Emulsões , Frutas/microbiologia , Micélio/crescimento & desenvolvimento , Esporos Fúngicos/crescimento & desenvolvimento
12.
J Antibiot (Tokyo) ; 73(8): 534-541, 2020 08.
Artigo em Inglês | MEDLINE | ID: mdl-32393809

RESUMO

Iseolides A-C (1-3), three new glycosylated macrolides, were identified from the culture extract of Streptomyces sp. DC4-5 isolated from a stony coral Dendrophyllia. Extensive analysis of one- and two-dimensional NMR data, coupled with MS/MS analytical data, revealed that iseolides are new congeners of 36-membered macrolides, PM100117 and PM100118, previously reported from a marine-derived Streptomyces. Iseolides showed potent antifungal activity against a plant pathogen Glomerella cingulata and human pathogens Candida albicans and Trichophyton rubrum with MIC in the range of 0.19-6.25 µg/mL.


Assuntos
Actinobacteria/química , Antozoários/química , Antifúngicos/química , Macrolídeos/química , Streptomyces/química , Animais , Antifúngicos/farmacologia , Arthrodermataceae/efeitos dos fármacos , Candida albicans/efeitos dos fármacos , Linhagem Celular Tumoral , Colletotrichum/efeitos dos fármacos , Humanos , Macrolídeos/farmacologia , Imageamento por Ressonância Magnética/métodos , Camundongos , Testes de Sensibilidade Microbiana/métodos , Espectrometria de Massas em Tandem/métodos
13.
Food Chem ; 327: 127060, 2020 Oct 15.
Artigo em Inglês | MEDLINE | ID: mdl-32454280

RESUMO

OBJECTIVES: This study set out to highlight the in vitro and in vivo antifungal activity of an Ethanolic Extract of Red Brazilian Propolis (EERBP) and identify bioactive fractions effective against Colletotrichum musae. METHODS: Active fractions were detected by the thin-layer chromatography-bioautography method and characterised by HPLC-MSn. RESULTS: The in vitro results showed that EERBP had strong antifungal properties againstC. musae (81 ± 1% inhibition at 1.6 g GAE L-1). Medicarpin, (3S)-vestitol and (3S)-neovestitol were the main compounds identified in the EERBP extract (45% of all detected peaks). Two isolated fractions displayed inhibition percentages of 35 ± 4 and 42 ± 1%, respectively, on C. musae mycelial growth compared to the EERBP extract. The biological activity of the two fractions displayed an additive effect. CONCLUSION: A further in vivo investigation revealed that EERBP is a potential natural alternative for controlling banana crown rot.


Assuntos
Antifúngicos/química , Extratos Vegetais/química , Própole/química , Antifúngicos/isolamento & purificação , Antifúngicos/farmacologia , Brasil , Cromatografia Líquida de Alta Pressão , Cromatografia em Camada Fina , Colletotrichum/efeitos dos fármacos , Testes de Sensibilidade Microbiana , Própole/metabolismo , Espectrometria de Massas por Ionização por Electrospray
14.
Braz J Microbiol ; 51(3): 989-997, 2020 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-32333271

RESUMO

Fungi in the genus Trichoderma are notorious producers of secondary metabolites with diverse applications, such as antibacterial, antifungal, and plant growth-promoting properties. Peptaibols are linear peptides produced by such fungi, with more than 440 compounds described to date, including tricholongins, longibrachins, trichobrachins, and trichovirins. Peptaibols are synthesized by non-ribosomal peptide synthetases and they have several biological activities. Our research group isolated four peptaibols (6DP2, 6DP3, 6DP4, and 6DP5) with antifungal activity against the plant pathogen Colletotrichum gloeosporioides and the proteasome (a cancer chemotherapy target) from Trichoderma sp. P8BDA1F1, an endophytic fungus from Begonia venosa. The ethyl acetate extract of this endophyte showed activity of 6.01% and 75% against C. gloeosporioides and the proteasome, respectively. The isolated compounds were identified by MS/MS and compared to literature data, suggesting the presence of trilongins BI, BII, BIII, and BIV, which are peptaibols containing 20 amino acid residues. The minimum inhibitory concentration against C. gloeosporioides was 40 µM for trilongin BI, 320 µM for trilongin BII, 160 µM for trilongin BIII, and 310 µM for trilongin BIV. BI-BIV trilongins inhibited proteasome ChTL activity, with IC50 values of 6.5 ± 2.7; 4.7 ± 1.8; 6.3 ± 2.2; and 2.7 ± 0.5 µM, respectively. The compounds were tested ex vivo against the intracellular amastigotes of Leishmania (L.) infantum but showed no selectivity. It is the first report of trilongins BI-BIV with antifungal activity against C. gloeosporioides and the proteasome target.


Assuntos
Antifúngicos/farmacologia , Antineoplásicos/farmacologia , Begoniaceae/microbiologia , Peptaibols/farmacologia , Trichoderma/química , Antifúngicos/química , Antifúngicos/isolamento & purificação , Antineoplásicos/química , Antineoplásicos/isolamento & purificação , Colletotrichum/efeitos dos fármacos , Endófitos , Concentração Inibidora 50 , Testes de Sensibilidade Microbiana , Peptaibols/química , Peptaibols/isolamento & purificação , Filogenia , Inibidores de Proteassoma/farmacologia , Trichoderma/classificação , Trichoderma/genética , Trichoderma/isolamento & purificação
15.
Folia Microbiol (Praha) ; 65(2): 381-392, 2020 Apr.
Artigo em Inglês | MEDLINE | ID: mdl-31401763

RESUMO

Citrus black spot (CBS) and post-bloom fruit drop (PFD), caused by Phyllosticta citricarpa and Colletotrichum abscissum, respectively, are two important citrus diseases worldwide. CBS depreciates the market value and prevents exportation of citrus fruits to Europe. PFD under favorable climatic conditions can cause the abscission of flowers, thereby reducing citrus production by 80%. An ecofriendly alternative to control plant diseases is the use of endophytic microorganisms, or secondary metabolites produced by them. Strain LGMF1631, close related to Diaporthe cf. heveae 1, was isolated from the medicinal plant Stryphnodendron adstringens and showed significant antimicrobial activity, in a previous study. In view of the potential presented by strain LGMF1631, and the absence of chemical data for secondary metabolites produced by D. cf. heveae, we decided to characterize the compounds produced by strain LGMF1631. Based on ITS, TEF1, and TUB phylogenetic analysis, strain LGMF1631 was confirmed to belong to D. cf. heveae 1. Chemical assessment of the fungal strain LGMF1631 revealed one new seco-dihydroisocoumarin [cladosporin B (1)] along with six other related, already known dihydroisocoumarin derivatives and one monoterpene [(-)-(1S,2R,3S,4R)-p-menthane-1,2,3-triol (8)]. Among the isolated metabolites, compound 5 drastically reduced the growth of both phytopathogens in vitro and completely inhibited the development of CBS and PFD in citrus fruits and flowers. In addition, compound 5 did not show toxicity against human cancer cell lines or citrus leaves, at concentrations higher than used for the inhibition of the phytopathogens, suggesting the potential use of (-)-(3R,4R)-cis-4-hydroxy-5-methylmellein (5) to control citrus diseases.


Assuntos
Ascomicetos/efeitos dos fármacos , Citrus/microbiologia , Fungicidas Industriais/farmacologia , Isocumarinas/farmacologia , Saccharomycetales/química , Ascomicetos/fisiologia , Colletotrichum/efeitos dos fármacos , Colletotrichum/fisiologia , Fabaceae/microbiologia , Frutas/microbiologia , Fungicidas Industriais/química , Fungicidas Industriais/metabolismo , Isocumarinas/química , Isocumarinas/metabolismo , Filogenia , Doenças das Plantas/microbiologia , Folhas de Planta/microbiologia , Saccharomycetales/classificação , Saccharomycetales/genética , Saccharomycetales/isolamento & purificação
16.
J Food Sci ; 84(12): 3418-3428, 2019 Dec.
Artigo em Inglês | MEDLINE | ID: mdl-31762032

RESUMO

In order to study the effect of volatile organic compounds (VOCs) produced by Bacillus subtilis CF-3 combined with heat treatment on Monilinia fructicola in peach and Colletotrichum gloeosporioides in litchi fruit, fruits were treated with B. subtilis CF-3 VOCs and hot air alone or in combination. The quality indexes of peach and litchi fruit after treatment and the changes in defense-related enzymes were measured. The results showed that the B. subtilis CF-3 VOCs combined with heat treatment could significantly reduce the rot index of peach and litchi fruit, and effectively maintain firmness and soluble solids content, as well as reduce weight loss of fruits. The combined treatment effectively enhanced the activity of peroxidase (POD), polyphenol oxidase (PPO), catalase (CAT), and superoxide dismutase (SOD) than either treatment alone, and enhanced the resistance of fruit to pathogenic fungi by activating disease-resistant enzymes (phenylalanine ammonia-lyase [PAL], chitinase [CHI], ß-1, 3-glucanase [GLU]) activity. In this study, B. subtilis CF-3 VOCs combined with heat treatment maintained the quality and delayed the decline of peach and litchi fruit, providing a theoretical basis for future applications. PRACTICAL APPLICATION: The combination of B. subtilis CF-3 VOCs and heat treatment reduce the extent of M. fructicola and C. gloeosporioides. The combination maintain the quality of peach and litchi better. The combination obviously improve the activity of defense-related enzyme in fruit.


Assuntos
Ascomicetos/efeitos dos fármacos , Bacillus subtilis/química , Colletotrichum/efeitos dos fármacos , Conservação de Alimentos/métodos , Litchi/microbiologia , Doenças das Plantas/microbiologia , Prunus persica/microbiologia , Compostos Orgânicos Voláteis/farmacologia , Ascomicetos/crescimento & desenvolvimento , Bacillus subtilis/metabolismo , Catecol Oxidase/metabolismo , Quitinases/metabolismo , Colletotrichum/crescimento & desenvolvimento , Frutas/enzimologia , Frutas/microbiologia , Temperatura Alta , Litchi/enzimologia , Fenilalanina Amônia-Liase/metabolismo , Proteínas de Plantas/metabolismo , Prunus persica/enzimologia , Compostos Orgânicos Voláteis/metabolismo
17.
J Agric Food Chem ; 67(43): 11877-11882, 2019 Oct 30.
Artigo em Inglês | MEDLINE | ID: mdl-31597038

RESUMO

The investigation of the metabolites from different cocultures of Nigrospora oryzae and Irpex lacteus in solid medium revealed two new squalenes (1 and 2); one new azaphilone (3); two new tremulane sesquiterpenes (4 and 5); and three known compounds, conocenol B (6), conocenol C (7), and 4-(4-dihydroxymethylphenoxy)benzaldehyde (8). The antagonistic relationship was examined by studying metabolite production. The production of compounds 6 and 8 by I. lacteus after the induction of coculture indicated significant selectivity for antifungal activity against phytopathogenic N. oryzae, with MICs of 16 µg/mL; compounds 6 and 8 also exhibited antifungal activities in vivo against Cerasus cerasoides infected by N. oryzae at concentrations of 100 µg/mL. New compounds 2 and 4 showed antifungal activities against Colletotrichum gloeosporioides, with MICs of 8 µg/mL, and compound 4 showed antifungal activity against Didymella glomerata with an MIC of 1 µg/mL. These results indicate that the mutually antagonistic relationship in the coculture of the phytopathogen and the endophyte can result in antibiotics that inhibit the phytopathogen and downregulate the production of phytotoxins by phytopathogenic N. oryzae. New compound 5 from I. lacteus showed weak activity against acetylcholinesterase (AChE), with an inhibition ratio of 16% at a concentration of 50 µM.


Assuntos
Antifúngicos/metabolismo , Ascomicetos/efeitos dos fármacos , Fungicidas Industriais/metabolismo , Polyporales/metabolismo , Esqualeno/metabolismo , Antifúngicos/química , Antifúngicos/farmacologia , Ascomicetos/crescimento & desenvolvimento , Técnicas de Cocultura , Colletotrichum/efeitos dos fármacos , Colletotrichum/crescimento & desenvolvimento , Fermentação , Fungicidas Industriais/química , Fungicidas Industriais/farmacologia , Doenças das Plantas/microbiologia , Polyporales/química , Polyporales/crescimento & desenvolvimento , Prunus/microbiologia , Esqualeno/química , Esqualeno/farmacologia
18.
Biomolecules ; 9(9)2019 08 22.
Artigo em Inglês | MEDLINE | ID: mdl-31443462

RESUMO

Guava is a fruit appreciated worldwide for its high content of bioactive compounds. However, it is considered a highly perishable fruit, generally attacked by pathogenic species such as the fungi Colletotrichum gloeosporioides, which causes anthracnosis. To diminish the losses caused by pathogenic fungi, coatings of chitosan (CS) with Ruta graveolens essential oil (RGEO) in different concentrations (0.5, 1.0, 1.5% v/v) were applied in situ and their effects on the physical properties and microbiological quality of the guavas were studied. The CS+RGEO coated fruits exhibited better physicochemical behavior and lower microbiological decay as compared to the uncoated guavas, demonstrating the effectiveness of the coatings, especially those with 1.5% of RGEO content. All the fruits coated had greater acceptance and quality than the controls, being more those with essential oil incorporation. In situ investigation of C. gloesporioides infection of guavas demonstrated that the CS+RGEO coated guavas showed a high percentage of inhibition in the development of anthracnose lesions. In the present investigation, an alternative method has been proposed to extend the stability of the guavas fruit up to 12 days with application in the food industry.


Assuntos
Quitosana/química , Quitosana/farmacologia , Colletotrichum/efeitos dos fármacos , Armazenamento de Medicamentos , Psidium/química , Ruta/química , Temperatura , Antifúngicos/química , Antifúngicos/farmacologia , Fenômenos Químicos , Materiais Revestidos Biocompatíveis/química , Materiais Revestidos Biocompatíveis/farmacologia , Indústria Alimentícia , Concentração de Íons de Hidrogênio , Fenômenos Mecânicos , Óleos Voláteis/química , Sensação , Solubilidade
19.
Hig. Aliment. (Online) ; 33(288/289): 2774-2778, abr.-maio 2019. tab
Artigo em Português | LILACS, VETINDEX | ID: biblio-1482335

RESUMO

O objetivo deste trabalho foi determinar a atividade antimicrobiana do carvacrol e sua combinação com tiabendazol no controle de fungos patogênicos deteriorantes de frutas (Colletotrichum gloesporioides, Fusarium solani e Alternaria alternata). O carvacrol apresentou uma concentração inibitória mínima (CIM) de 282 a 563 μg mL-1 para os fungos testados. Quando avaliado em conjunto com o tiabendazol apresentou efeito aditivo contra C. gloesporioides e F. solani (FICI 0,5 e 1,0, respectivamente) e sinérgico contra a A.alternata (FICI 0,1). Houve redução da CIM do carvacrol de 50 a 88%. Este estudo mostra o potencial do uso.


Assuntos
Alternaria/efeitos dos fármacos , Colletotrichum/efeitos dos fármacos , Fungicidas Industriais/administração & dosagem , Fungicidas Industriais/análise , Fungos/efeitos dos fármacos , Fusarium/efeitos dos fármacos , Microbiologia de Alimentos , Tiabendazol/administração & dosagem , Sinergismo Farmacológico
20.
Microb Pathog ; 130: 71-80, 2019 May.
Artigo em Inglês | MEDLINE | ID: mdl-30844473

RESUMO

Mandacaru (Cereus jamacaru DC.), is a cactaceous symbol of caatinga vegetation at Brazilian Northeast region, however, there are no much studies about biochemical properties of this species. Here, the pioneering study brings very relevant data to highlight the importance of research with endemic plants of the caatinga. Afterward, the presence of enzymes such as peroxidase, protease, chitinase, ß-1,3-glucanase, and serine (trypsin) and cysteine (papain) protease inhibitors were evaluated. The peroxidase activity was higher in roots than other tissues. The ß-1,3-glucanase and proteolytic activity were prominent in stem and roots. The chitinase activity and protease inhibitor for both classes analyzed were detected in the stem and fruit peel. Antifungal activity against Colletotrichum gloeosporioides showed the root extract has a promising inhibitory activity on this economical important phytopathogenic fungus. After the contact of the hyphae with root extract increase in membrane permeability, based on Propidium Iodide (PI) uptake, and production of reactive oxygen species (ROS) were detected, compared to negative control. In addition, Scanning Electron Microscopy (SEM) analysis showed morphological damage on hyphae structure indicating that the treatment debilitates either cell membrane or cell wall leading to the cell death C. gloeosporioides.


Assuntos
Antifúngicos/farmacologia , Cactaceae/química , Membrana Celular/efeitos dos fármacos , Membrana Celular/patologia , Colletotrichum/crescimento & desenvolvimento , Proteínas de Plantas/farmacologia , Espécies Reativas de Oxigênio/metabolismo , Antifúngicos/isolamento & purificação , Cactaceae/enzimologia , Colletotrichum/efeitos dos fármacos , Colletotrichum/enzimologia , Colletotrichum/ultraestrutura , Enzimas/análise , Frutas/química , Frutas/enzimologia , Hifas/ultraestrutura , Viabilidade Microbiana/efeitos dos fármacos , Microscopia Eletrônica de Varredura , Permeabilidade/efeitos dos fármacos , Proteínas de Plantas/isolamento & purificação , Raízes de Plantas/química , Raízes de Plantas/enzimologia , Caules de Planta/química , Caules de Planta/enzimologia
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