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1.
J Appl Microbiol ; 135(6)2024 Jun 03.
Artículo en Inglés | MEDLINE | ID: mdl-38802124

RESUMEN

AIMS: Anthracnose caused by Colletotrichum species is one of the most devastating diseases of fruits and crops. We isolated and identified an antifungal compound from the mushroom Coprinus comatus and investigated its inhibitory potential against anthracnose disease-causing fungi with the goal of discovering natural products that can suppress anthracnose-caused plant disease. METHODS AND RESULTS: The culture filtrate of C. comatus was subjected to a bioassay-guided isolation of antifungal compounds. The active compound was identified as orsellinaldehyde (2,4-dihydroxy-6-methylbenzaldehyde) based on mass spectroscopy and nuclear magnetic resonance analyses. Orsellinaldehyde displayed broad-spectrum inhibitory activity against different plant pathogenic fungi. Among the tested Colletotrichum species, it exhibited the lowest IC50 values on conidial germination and germ tube elongation of Colletotrichum orbiculare. The compound also showed remarkable inhibitory activity against Colletotrichum gloeosporiodes. The staining of Colletotrichum conidia with fluorescein diacetate and propidium iodide demonstrated that the compound is fungicidal. The postharvest in-vivo detached fruit assay indicated that orsellinaldehyde suppressed anthracnose lesion symptoms on mango and cucumber fruits caused by C. gloeosporioides and C. orbiculare, respectively. CONCLUSIONS: Orsellinaldehyde was identified as a potent antifungal compound from the culture filtrate of C. comatus. The inhibitory and fungicidal activities of orsellinaldehyde against different Colletotrichum species indicate its potential as a fungicide for protecting various fruits against anthracnose disease-causing fungi.


Asunto(s)
Colletotrichum , Coprinus , Enfermedades de las Plantas , Colletotrichum/efectos de los fármacos , Enfermedades de las Plantas/microbiología , Enfermedades de las Plantas/prevención & control , Benzaldehídos/farmacología , Antifúngicos/farmacología , Fungicidas Industriales/farmacología , Esporas Fúngicas/efectos de los fármacos
2.
J Nat Prod ; 87(5): 1347-1357, 2024 May 24.
Artículo en Inglés | MEDLINE | ID: mdl-38701173

RESUMEN

A chemical investigation of a cold-seep-sediment-derived fungus, Pseudallescheria boydii CS-793, resulted in characterization of 10 novel bergamotene-derived sesquiterpenoids, pseuboyenes A-J (1-10). Their structures were elucidated by spectroscopic and X-ray crystallographic analyses as well as using the modified Mosher's method. Compound 1 represents the first example of a ß-bergamotene containing a 6-oxobicyclo[3.2.1]octane nucleus adducted with a methyl lactate unit, while 8-10 involve a skeletal rearrangement from bergamotene. Compounds 2-5 showed significant antifungal activities against Colletotrichum gloeosporioides Penz. and Fusarium oxysporum with MICs ranging from 0.5 to 8 µg/mL. Compound 4 exhibited an in vitro anti-F. proliferatum effect with an EC50 value of 1.0 µg/mL.


Asunto(s)
Antifúngicos , Pruebas de Sensibilidad Microbiana , Pseudallescheria , Sesquiterpenos , Antifúngicos/farmacología , Antifúngicos/química , Sesquiterpenos/farmacología , Sesquiterpenos/química , Sesquiterpenos/aislamiento & purificación , Estructura Molecular , Colletotrichum/efectos de los fármacos , Fusarium/efectos de los fármacos , Cristalografía por Rayos X
3.
J Nat Prod ; 87(4): 705-712, 2024 Apr 26.
Artículo en Inglés | MEDLINE | ID: mdl-38547118

RESUMEN

Penicilloneines A (1) and B (2) are the first reported quinolone-citrinin hybrids. They were isolated from the starfish-derived fungus Penicillium sp. GGF16-1-2, and their structures were elucidated using spectroscopic, chemical, computational, and single-crystal X-ray diffraction methods. Penicilloneines A (1) and B (2) share a common 4-hydroxy-1-methyl-2(1H)-quinolone unit; however, they differ in terms of citrinin moieties, and these two units are linked via a methylene bridge. Penicilloneines A (1) and B (2) exhibited antifungal activities against Colletotrichum gloeosporioides, with lethal concentration 50 values of 0.02 and 1.51 µg/mL, respectively. A mechanistic study revealed that 1 could inhibit cell growth and promote cell vacuolization and consequent disruption of the fungal cell walls via upregulating nutrient-related hydrolase genes, including putative hydrolase, acetylcholinesterase, glycosyl hydrolase, leucine aminopeptidase, lipase, and beta-galactosidase, and downregulating their synthase genes 3-carboxymuconate cyclase, pyruvate decarboxylase, phosphoketolase, and oxalate decarboxylase.


Asunto(s)
Antifúngicos , Citrinina , Colletotrichum , Penicillium , Quinolonas , Penicillium/química , Colletotrichum/efectos de los fármacos , Quinolonas/farmacología , Quinolonas/química , Quinolonas/aislamiento & purificación , Estructura Molecular , Animales , Citrinina/farmacología , Citrinina/química , Citrinina/aislamiento & purificación , Antifúngicos/farmacología , Antifúngicos/química , Antifúngicos/aislamiento & purificación , Pruebas de Sensibilidad Microbiana
4.
Chem Biodivers ; 21(6): e202400327, 2024 Jun.
Artículo en Inglés | MEDLINE | ID: mdl-38446672

RESUMEN

Four new isocoumarins, alternariethers A-C (1-3) and alternariester (4) were separated from the fermentation of the fungus Alternaria malorum FL39, purified from Myoporum bontioides. Their structures were ascertained using NMR and HR-ESI-MS spectroscopy. For compound 4, the absolute configuration was solved with the help of ECD calculation and the DP4+ method. Compared with the positive control triadimefon, compound 1 showed more potent antifungal effects on Colletotrichum musae. The antifungal effects of compounds 1, 2, and 3 on Fusarium oxysporum and Fusarium graminearum, of compound 4 on F. oxysporum, were equal to those of triadimefon. Except for compound 4 which was inactive against Escherichia coli with O78 serotype, all compounds showed moderate or weak antibacterial activity against Staphylococcus aureus ATCC 6538 and E. coli with O6 or O78 serotype.


Asunto(s)
Alternaria , Antibacterianos , Escherichia coli , Fusarium , Isocumarinas , Pruebas de Sensibilidad Microbiana , Staphylococcus aureus , Alternaria/química , Alternaria/efectos de los fármacos , Staphylococcus aureus/efectos de los fármacos , Escherichia coli/efectos de los fármacos , Isocumarinas/química , Isocumarinas/farmacología , Isocumarinas/aislamiento & purificación , Antibacterianos/farmacología , Antibacterianos/química , Antibacterianos/aislamiento & purificación , Fusarium/efectos de los fármacos , Colletotrichum/efectos de los fármacos , Antifúngicos/farmacología , Antifúngicos/química , Antifúngicos/aislamiento & purificación , Myoporum/química , Myoporum/metabolismo
5.
Plant Dis ; 108(6): 1526-1532, 2024 Jun.
Artículo en Inglés | MEDLINE | ID: mdl-38105460

RESUMEN

Two previously published ripe rot prediction models, DF2-NN and GH2-DT, were evaluated for fungicide application timing efficacy in Maryland vineyards. Both models utilize leaf wetness duration (LWD), temperature, and grape cluster phenological stages as model parameters. These three parameters were tracked throughout the 2021 to 2023 seasons in three vineyards. The fungicide efficacy trials started at the veraison phenological stage and included a nontreated control, a 12-day interval treatment, and two model-triggered treatments when risk predicted by the models crossed a threshold. The severity of ripe rot on the clusters in each treatment was assessed when the fruit were mature. Ripe rot severity in the nontreated controls was higher during seasons with more LWD and more precipitation. Days in which the models were triggered by the environmental conditions primarily coincided with precipitation events and lengthy LWDs. The model-triggered treatments never had significantly higher ripe rot severity than the 12-day interval treatment but had significantly lower severities than the nontreated control in most trials which had high ripe rot pressure. Furthermore, the model-triggered treatments resulted in fewer fungicide applications than the 12-day interval treatment on average. The DF2-NN model appeared to be more accurate and useful for ripe rot prediction and treatment than the GH2-DT model because it triggered fewer fungicide applications while reducing ripe rot. This model may be useful for improving or maintaining ripe rot control with fewer fungicide inputs, which may be beneficial for the environment and the reduction of fungicide resistance selection.


Asunto(s)
Colletotrichum , Fungicidas Industriales , Enfermedades de las Plantas , Vitis , Fungicidas Industriales/farmacología , Vitis/microbiología , Colletotrichum/efectos de los fármacos , Colletotrichum/fisiología , Enfermedades de las Plantas/prevención & control , Enfermedades de las Plantas/microbiología , Maryland , Frutas/microbiología , Estaciones del Año
6.
Molecules ; 29(11)2024 May 25.
Artículo en Inglés | MEDLINE | ID: mdl-38893377

RESUMEN

Plant pathogenic fungi pose a major threat to global food security, ecosystem services, and human livelihoods. Effective and broad-spectrum fungicides are needed to combat these pathogens. In this study, a novel antifungal 2-oxyacetate hydrazide quinoxaline scaffold as a simple analogue was designed and synthesized. Their antifungal activities were evaluated against Botrytis cinerea (B. cinerea), Altemaria solani (A. solani), Gibberella zeae (G. zeae), Rhizoctonia solani (R. solani), Colletotrichum orbiculare (C. orbiculare), and Alternaria alternata (A. alternata). These results demonstrated that most compounds exhibited remarkable inhibitory activities and possessed better efficacy than ridylbacterin, such as compound 15 (EC50 = 0.87 µg/mL against G. zeae, EC50 = 1.01 µg/mL against C. orbiculare) and compound 1 (EC50 = 1.54 µg/mL against A. alternata, EC50 = 0.20 µg/mL against R. solani). The 3D-QSAR analysis of quinoxaline-2-oxyacetate hydrazide derivatives has provided new insights into the design and optimization of novel antifungal drug molecules based on quinoxaline.


Asunto(s)
Antifúngicos , Pruebas de Sensibilidad Microbiana , Relación Estructura-Actividad Cuantitativa , Quinoxalinas , Antifúngicos/farmacología , Antifúngicos/síntesis química , Antifúngicos/química , Quinoxalinas/farmacología , Quinoxalinas/química , Quinoxalinas/síntesis química , Diseño de Fármacos , Alternaria/efectos de los fármacos , Rhizoctonia/efectos de los fármacos , Botrytis/efectos de los fármacos , Estructura Molecular , Colletotrichum/efectos de los fármacos , Gibberella/efectos de los fármacos
7.
Bioorg Med Chem Lett ; 55: 128481, 2022 01 01.
Artículo en Inglés | MEDLINE | ID: mdl-34852242

RESUMEN

Structural optimization using plant secondary metabolites as templates is one of the important approach to discover pesticide molecules with novel skeletons. Xanthatin, a natural sesquiterpene lactone isolated from the Xanthium plants (Family: Compositae), exhibits important biological properties. In this work, a series of Michael-type amino derivatives were prepared from xanthatin and their structures were characterized by 1H NMR, 13C NMR and HR-MS, and their antifungal activities against several phytopathogenic fungi were evaluated according to the spore germination method and mycelium growth rate method in vitro. The results illustrated that compounds 2g (IC50 = 78.91 µg/mL) and 2o (IC50 = 64.51 µg/mL) exhibited more promising inhibition activity against spores of F. solani than precursor xanthatin, compounds 2g, 2l, and 2r exhibited remarkable antifungal effect on C. mandshurica with the average inhibition rates (AIRs) >90%, whereas the AIR of xanthatin was only 59.34%. Meanwhile, the preliminary structure-activity relationships suggested that the amino containing 2-methoxyethyl or 4-chlorophenylmethyl group appended in the C-13 position of xanthatin could yield potential compounds against fungal spores, and the exocyclic double bond of xanthatin is essential to maintain its mycelial growth inhibitory activity. Therefore, the aforementioned findings indicate that partial xanthatin amino-derivatives could be considered for further exploration as the potential lead structures toward development of the new environmentally friendly fungicidal candidates for sustainable crop protection.


Asunto(s)
Antifúngicos/farmacología , Furanos/farmacología , Xanthium/química , Alternaria/efectos de los fármacos , Antifúngicos/síntesis química , Antifúngicos/química , Botrytis/efectos de los fármacos , Colletotrichum/efectos de los fármacos , Relación Dosis-Respuesta a Droga , Furanos/síntesis química , Furanos/química , Fusarium/efectos de los fármacos , Pruebas de Sensibilidad Microbiana , Estructura Molecular , Relación Estructura-Actividad
8.
J Sci Food Agric ; 102(2): 696-706, 2022 Jan 30.
Artículo en Inglés | MEDLINE | ID: mdl-34173241

RESUMEN

BACKGROUND: Microorganism for biological control of fruit diseases is an eco-friendly alternative to the use of chemical fungicides. RESULTS: This is the first study evaluating the electrospraying process to encapsulate the biocontrol yeast Meyerozyma caribbica. The effect of encapsulating material [Wey protein concentrate (WPC), Fibersol® and Trehalose], its concentration and storage temperature on the cell viability of M. caribbica, and in vitro and in vivo control of Colletotrichum gloeosporioides was evaluated. The processing with commercial resistant maltodextrin (Fibersol®) 30% (w/v) as encapsulating material showed the highest initial cell viability (95.97 ± 1.01%). The storage at 4 ± 1 °C showed lower losses of viability compared to 25 ± 1 °C. Finally, the encapsulated yeast with Fibersol 30% w/v showed inhibitory activity against anthracnose in the in vitro and in vivo tests, similar to yeast fresh cells. CONCLUSION: Electrospraying was a highly efficient process due to the high cell viability, and consequently, a low quantity of capsules is required for the postharvest treatment of fruits. Additionally, the yeast retained its antagonistic power during storage. © 2021 Society of Chemical Industry.


Asunto(s)
Agentes de Control Biológico/química , Agentes de Control Biológico/farmacología , Carica/microbiología , Colletotrichum/efectos de los fármacos , Composición de Medicamentos/métodos , Mangifera/microbiología , Saccharomycetales/química , Antibiosis , Colletotrichum/crecimiento & desarrollo , Composición de Medicamentos/instrumentación , Frutas/microbiología , Viabilidad Microbiana , Saccharomycetales/fisiología
9.
Bioorg Med Chem Lett ; 43: 128089, 2021 07 01.
Artículo en Inglés | MEDLINE | ID: mdl-33964438

RESUMEN

Several boron-containing small molecules have been approved by the US FDA to treat human diseases. We explored potential applications of boron-containing compounds in modern agriculture by pursuing multiple research and development programs. Here, we report a novel series of multi-substitution benzoxaboroles (1-36), a compound class that we recently reported as targeting geranylgeranyl transferase I (GGTase I) and thereby inhibiting protein prenylation (Kim et al., 2020). These compounds were designed, synthesized, and tested against the agriculturally important fungal pathogens Mycosphaerella fijiensis and Colletotrichum sublineolum in a structure-activity relationship (SAR) study. Compounds 13, 28, 30, 34 and 36 were identified as active leads with excellent antifungal MIC95 values in the range of 1.56-3.13 ppm against M. fijiensis and 0.78-3.13 ppm against C. sublineolum.


Asunto(s)
Antifúngicos/farmacología , Ascomicetos/efectos de los fármacos , Compuestos de Boro/farmacología , Colletotrichum/efectos de los fármacos , Fungicidas Industriales/farmacología , Agricultura , Transferasas Alquil y Aril/antagonistas & inhibidores , Transferasas Alquil y Aril/metabolismo , Antifúngicos/síntesis química , Antifúngicos/química , Ascomicetos/metabolismo , Compuestos de Boro/síntesis química , Compuestos de Boro/química , Colletotrichum/metabolismo , Relación Dosis-Respuesta a Droga , Fungicidas Industriales/síntesis química , Fungicidas Industriales/química , Pruebas de Sensibilidad Microbiana , Estructura Molecular , Relación Estructura-Actividad
10.
Bioorg Med Chem ; 40: 116184, 2021 06 15.
Artículo en Inglés | MEDLINE | ID: mdl-33971489

RESUMEN

Plant pathogenic fungi decrease the quality and productivity of plant production. The botanical fungicides have better biocompatibility and rapid biodegradation, little or no cross resistance, and the structural diversity, and thus are beneficial to deal with plant fungal diseases. Osthole has been widely used as the commercial botanical fungicide against powdery mildew in China. In this article, a series of osthole derivatives were synthesized, which respectively contain different substituents on the benzene ring, at the C8-position and pyrone ring. All the target compounds were evaluated in vitro for their antifungal activity against resistant phytopathogenic fungi. Colletotrichum fragariae, Strawberry Botrytis Cinerea, Kiwifruit Botrytis Cinerea, Kiwifruit brown Rots, which are common in fruit fungal diseases. The compound C4 was identified as the most promising candidate with the EC50 values at 38.7 µg/mL against Colletotrichum Fragariae, 14.5 µg/mL against Strawberry Botrytis Cinerea and 24.3 µg/mL against Kiwifruit Botrytis Cinerea, respectively, whereas the antifungal activity against resistant phytopathogenic fungi. of osthole is too low to be used (EC50 > 400 ppm). The results of mycelial relative conductivity determination, PI uptake and fluorescence spectroscopy indicated that the cell membrane of fungi is the key action site of C4. Besides, C4 has the potent inhibitory activity against both of plant and human pathogenic bacteria. Our studies showed that C4 was worthy for further attention as a promising botanical fungicide candidate in crop protection.


Asunto(s)
Antifúngicos/farmacología , Botrytis/efectos de los fármacos , Colletotrichum/efectos de los fármacos , Cumarinas/farmacología , Protección de Cultivos , Fungicidas Industriales/farmacología , Antifúngicos/síntesis química , Antifúngicos/química , Cumarinas/síntesis química , Cumarinas/química , Relación Dosis-Respuesta a Droga , Fungicidas Industriales/síntesis química , Fungicidas Industriales/química , Estructura Molecular , Enfermedades de las Plantas/microbiología , Relación Estructura-Actividad
11.
Bioorg Chem ; 115: 105232, 2021 10.
Artículo en Inglés | MEDLINE | ID: mdl-34371373

RESUMEN

The strategy "IEMAHC" (Induction of Endophyte Metabolism by Adding Host Components) was applied to the fermentation of the endophytic fungus Epicoccum sorghinum L28 from Myoporum bontioides by introducing guaiol, an ingredient of M. bontioides, into the cultivation medium, which resulted in the purification of nine new diphenyl ethers, epicoccethers A-I (1-9). Their structures were determined by overall spectroscopic analysis. HPLC-MS analysis revealed that compounds 5-7 were products generated by induction of guaiol. Compounds 6 and 7 are the first members containing an ester moiety formed by the natural long-chain fatty acid and the hydroxyl group in the phenylmethanol unit of the diphenyl ether class. The antifungal activities of compounds 1, 2, and 4-7 against Fusarium oxysporum were 1, 1, 2, 1, 2 and 4 times as high as those of the positive control triadimefon, respectively. Compounds 4 and 5 showed 1.6 times the antifungal activities of triadimefon towards Colletotrichum musae.


Asunto(s)
Antifúngicos/farmacología , Ascomicetos/química , Colletotrichum/efectos de los fármacos , Fusarium/efectos de los fármacos , Éteres Fenílicos/farmacología , Antifúngicos/química , Antifúngicos/aislamiento & purificación , Relación Dosis-Respuesta a Droga , Pruebas de Sensibilidad Microbiana , Estructura Molecular , Éteres Fenílicos/química , Éteres Fenílicos/aislamiento & purificación , Relación Estructura-Actividad
12.
Chem Biodivers ; 18(3): e2000941, 2021 Mar.
Artículo en Inglés | MEDLINE | ID: mdl-33507621

RESUMEN

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.


Asunto(s)
Antifúngicos/farmacología , Colletotrichum/efectos de los fármacos , Lepidium/química , Aceites Volátiles/farmacología , Enfermedades de las Plantas/prevención & control , Sustancias Protectoras/farmacología , Antifúngicos/química , Antifúngicos/aislamiento & purificación , Suplementos Dietéticos , Frutas/química , Pruebas de Sensibilidad Microbiana , Aceites Volátiles/química , Aceites Volátiles/aislamiento & purificación , Sustancias Protectoras/química , Sustancias Protectoras/aislamiento & purificación , Solanum/química
13.
Int J Mol Sci ; 22(8)2021 Apr 14.
Artículo en Inglés | MEDLINE | ID: mdl-33919762

RESUMEN

The hemibiotrophic ascomycete fungus Colletotrichum gloeosporioides is the causal agent of anthracnose on numerous plants, and it causes considerable economic losses worldwide. Endocytosis is an essential cellular process in eukaryotic cells, but its roles in C. gloeosporioides remain unknown. In our study, we identified an endocytosis-related protein, CgEnd3, and knocked it out via polyethylene glycol (PEG)-mediated protoplast transformation. The lack of CgEnd3 resulted in severe defects in endocytosis. C. gloeosporioides infects its host through a specialized structure called appressorium, and ΔCgEnd3 showed deficient appressorium formation, melanization, turgor pressure accumulation, penetration ability of appressorium, cellophane membrane penetration, and pathogenicity. CgEnd3 also affected oxidant adaptation and the expression of core effectors during the early stage of infection. CgEnd3 contains one EF hand domain and four calcium ion-binding sites, and it is involved in calcium signaling. A lack of CgEnd3 changed the responses to cell-wall integrity agents and fungicide fludioxonil. However, CgEnd3 regulated appressorium formation and endocytosis in a calcium signaling-independent manner. Taken together, these results demonstrate that CgEnd3 plays pleiotropic roles in endocytosis, calcium signaling, cell-wall integrity, appressorium formation, penetration, and pathogenicity in C. gloeosporioides, and it suggests that CgEnd3 or endocytosis-related genes function as promising antifungal targets.


Asunto(s)
Colletotrichum/patogenicidad , Endocitosis , Proteínas Fúngicas/metabolismo , Enfermedades de las Plantas/microbiología , Populus/microbiología , Adaptación Fisiológica/efectos de los fármacos , Antifúngicos/farmacología , Señalización del Calcio/efectos de los fármacos , Pared Celular/efectos de los fármacos , Pared Celular/metabolismo , Celofán , Colletotrichum/efectos de los fármacos , Colletotrichum/crecimiento & desarrollo , Colletotrichum/metabolismo , Dioxoles/farmacología , Endocitosis/efectos de los fármacos , Eliminación de Gen , Hifa/efectos de los fármacos , Melaninas/metabolismo , Oxidantes/toxicidad , Estrés Oxidativo/efectos de los fármacos , Hojas de la Planta/microbiología , Presión , Pirroles/farmacología , Virulencia/efectos de los fármacos
14.
Molecules ; 26(22)2021 Nov 11.
Artículo en Inglés | MEDLINE | ID: mdl-34833910

RESUMEN

The greatest challenge for the avocado (Persea americana Miller) industry is to maintain the quality of the fruit to meet consumer requirements. Anthracnose is considered the most important disease in this industry, and it is caused by different species of the genus Colletotrichum, although other pathogens can be equally important. The defense mechanisms that fruit naturally uses can be triggered in response to the attack of pathogenic microorganisms and also by the application of exogenous elicitors in the form of GRAS compounds. The elicitors are recognized by receptors called PRRs, which are proteins located on the avocado fruit cell surface that have high affinity and specificity for PAMPs, MAMPs, and DAMPs. The activation of defense-signaling pathways depends on ethylene, salicylic, and jasmonic acids, and it occurs hours or days after PTI activation. These defense mechanisms aim to drive the pathogen to death. The application of essential oils, antagonists, volatile compounds, chitosan and silicon has been documented in vitro and on avocado fruit, showing some of them to have elicitor and fungicidal effects that are reflected in the postharvest quality of the fruit and a lower incidence of diseases. The main focus of these studies has been on anthracnose diseases. This review presents the most relevant advances in the use of natural compounds with antifungal and elicitor effects in plant tissues.


Asunto(s)
Colletotrichum/patogenicidad , Persea/microbiología , Enfermedades de las Plantas/microbiología , Enfermedades de las Plantas/prevención & control , Antifúngicos/farmacología , Agentes de Control Biológico/farmacología , Quitosano/farmacología , Colletotrichum/efectos de los fármacos , Resistencia a la Enfermedad/fisiología , Frutas/efectos de los fármacos , Frutas/microbiología , Frutas/fisiología , Aceites Volátiles/farmacología , Persea/efectos de los fármacos , Persea/fisiología , Compuestos Orgánicos Volátiles/farmacología
15.
J Environ Sci Health B ; 56(1): 73-81, 2021.
Artículo en Inglés | MEDLINE | ID: mdl-33131418

RESUMEN

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.


Asunto(s)
Aceites Volátiles/farmacología , Enfermedades de las Plantas/prevención & control , Vitis , Botrytis/efectos de los fármacos , Colletotrichum/efectos de los fármacos , Eucalyptus/química , Granjas , Microbiología de Alimentos , Aceites Volátiles/química , Enfermedades de las Plantas/microbiología , Vitis/química , Vitis/microbiología , Compuestos Orgánicos Volátiles/análisis , Vino/análisis
16.
Angew Chem Int Ed Engl ; 60(52): 27271-27276, 2021 12 20.
Artículo en Inglés | MEDLINE | ID: mdl-34729882

RESUMEN

Radical fluorosulfonylation is emerging as an appealing approach for the synthesis of sulfonyl fluorides, which have widespread applications in many fields, in particular in the context of chemical biology and drug development. Here, we report the first investigation of FSO2 radical generation under electrochemical conditions, and the establishment of a new and facile approach for the synthesis of ß-keto sulfonyl fluorides via oxo-fluorosulfonylation of alkynes with sulfuryl chlorofluoride as the radical precursor and air as the oxidant. This electrochemical protocol is amenable to access two different products (ß-keto sulfonyl fluorides or α-chloro-ß-keto sulfonyl fluorides) with the same reactants. The ß-keto sulfonyl fluoride products can be utilized as useful building blocks in the synthesis of various derivatives and heterocycles, including the first synthesis of an oxathiazole dioxide compound. Furthermore, some ß-keto sulfonyl fluorides and derivatives exhibited notably potent activities against Bursaphelenchus xylophilus and Colletotrichum gloeosporioides.


Asunto(s)
Alquinos/química , Sulfonas/síntesis química , Animales , Antihelmínticos/farmacología , Antifúngicos/farmacología , Colletotrichum/efectos de los fármacos , Técnicas Electroquímicas , Rabdítidos/efectos de los fármacos , Sulfonas/farmacología
17.
Fungal Genet Biol ; 135: 103289, 2020 02.
Artículo en Inglés | MEDLINE | ID: mdl-31704368

RESUMEN

The HOG (high-osmolarity glycerol) pathway is critical for the appropriate adaptation to adverse conditions. Here, we demonstrated that the deletion of CgHog1 resulted in enhanced sensitivity to osmotic stress and increased resistance to fludioxonil in the poplar anthracnose fungus Colletotrichum gloeosporioides. The accumulation of chitin around hyphal tips was obviously decreased in the ΔCgHog1 strain under sorbitol, whereas it strongly was increased in the response to fludioxonil compared with the wild type. To investigate the underlying mechanism of CgHog1-mediated adaption to osmotic stress and fludioxonil, transcriptomic profiles were performed in both the ΔCgHog1 strain and the wild type under the treatment of sorbitol and fludioxonil, respectively. Under sorbitol, genes associated with glycolysis, lipid metabolism, and accumulation of soluble sugars and amino acids were differentially expressed; under fludioxonil, vesicle trafficking-related genes were highly downregulated in the ΔCgHog1 strain, which was consistent with abnormal vacuoles distribution and morphology of hyphae, indicating that the growth defect caused by fludioxonil may be associated with disruption of endocytosis. Taken together, we elucidated the adaptation mechanisms of how CgHog1 regulates appropriate response to sorbitol and fludioxonil via different metabolism pathways. These findings extend our insights into the HOG pathway in fungi.


Asunto(s)
Colletotrichum/efectos de los fármacos , Colletotrichum/genética , Dioxoles/farmacología , Proteínas Fúngicas/genética , Proteínas Quinasas Activadas por Mitógenos/genética , Pirroles/farmacología , Sorbitol/farmacología , Adaptación Fisiológica , Regulación hacia Abajo , Regulación Fúngica de la Expresión Génica , Hifa/metabolismo , Presión Osmótica , Enfermedades de las Plantas/microbiología , Hojas de la Planta/microbiología , Populus/microbiología
18.
Appl Environ Microbiol ; 86(21)2020 10 15.
Artículo en Inglés | MEDLINE | ID: mdl-32859591

RESUMEN

In the present study, a deep-sea bacterial strain designated Bacillus sp. strain wsm-1 was screened and found to exhibit strong antifungal activity against many plant-pathogenic fungi, and corresponding antifungal agents were thereby purified and determined by tandem mass spectrometry to be two cyclic lipopeptide homologs. These homologs, which were different from any previously reported lipopeptides, were identified to possess identical amino acid sequences of ß-amino fatty acid-Asn-Ser-Asn-Pro-Tyr-Asn-Gln and deduced as two novel lipopeptides designated C14 iturin W and C15 iturin W. Electron microscopy observation indicated that both iturin W homologs caused obvious morphological changes and serious disruption of plasma membrane toward fungal cells, while C15 iturin W exhibited more serious cell damages than C14 iturin W did, which was well consistent with the results of the antifungal activity assays. To improve the yield and antifungal activity of iturin W, the effects of different carbon and nitrogen sources and amino acids on production of C14 iturin W and C15 iturin W were investigated. The results indicated that supplements of most of the detected carbon and nitrogen sources could increase the yield of C14 iturin W, but inhibit the yield of C15 iturin W, while supplements of tryptone and most of the detected amino acids could increase the yield of both C14 iturin W and C15 iturin W.IMPORTANCE Plant disease caused by pathogenic fungi is one of the most devastating diseases, which affects the food safety of the whole world to a great extent. Biological control of plant diseases by microbial natural products is more desirable than traditional chemical control. In this study, we discovered a novel lipopeptide, iturin W, with promising prospects in biological control of plant diseases. Moreover, the effects of different carbon and nitrogen sources and amino acids on production of C14 iturin W and C15 iturin W would provide a reasonable basis for the optimization of the fermentation process of lipopeptides. Notably, the structure of iturin W was different from that of any previously reported lipopeptide, suggesting that deep-sea microorganisms might produce many novel natural products and have significant potential in the development of biological products in the future.


Asunto(s)
Antifúngicos/farmacología , Proteínas Bacterianas/farmacología , Hongos/efectos de los fármacos , Lipopéptidos/farmacología , Péptidos Cíclicos/fisiología , Alternaria/efectos de los fármacos , Antifúngicos/química , Bacillus , Proteínas Bacterianas/química , Colletotrichum/efectos de los fármacos , Fungicidas Industriales/química , Fungicidas Industriales/farmacología , Fusarium/efectos de los fármacos , Lipopéptidos/química , Magnaporthe/efectos de los fármacos , Péptidos Cíclicos/química , Análisis de Secuencia de Proteína
19.
New Phytol ; 225(4): 1788-1798, 2020 02.
Artículo en Inglés | MEDLINE | ID: mdl-31598980

RESUMEN

Fruit defense against pathogens relies on induced and preformed mechanisms. The present contribution evaluated performed resistance of red and green mango fruit against the fungal pathogen Colletotrichum gloeosporioides and identified the main active antifungal components. High-performance liquid chromatography analysis of nonhydrolyzed mango peel extracts identified major anthocyanin peaks of glycosylated cyanidin and methylcyanidin, and flavonol peaks of glycosylated quercetin and kaempferol, which were more abundant on the 'red side' of red mango fruit. Organic extracts of red vs green mango peel were more efficient in inhibiting C. gloeosporioides. Transcriptome analysis of the mango-C. gloeosporioides interaction showed increased expression of glucosidase genes related to both fungal pathogenicity and host defense. Glucosidase treatment of organic peel extract increased its antifungal activity. Additionally, quercetin and cyanidin had significantly higher antifungal activity than their glycosylated derivatives. Peel extract volatiles treated with glucosidase had antifungal activity. GCMS analysis identified 15 volatiles after glucosidase hydrolysis, seven of them present only in red fruit. These results suggest that the fruit obtains a concealed arsenal of glycosylated flavonoids in its peel when they are hydrolyzed by ß-glucosidase that is induced in both fungus and host during infection process, become more toxic to the fungal pathogen, inhibiting decay development.


Asunto(s)
Colletotrichum/efectos de los fármacos , Flavonoides/farmacología , Frutas/química , Mangifera/química , Extractos Vegetales/farmacología , Flavonoides/química , Mangifera/microbiología , Fenoles/química , Fenoles/farmacología , Extractos Vegetales/química
20.
Arch Microbiol ; 202(6): 1459-1467, 2020 Aug.
Artículo en Inglés | MEDLINE | ID: mdl-32189017

RESUMEN

Sunflower is one of the most economically important oil crops. Recently, sunflower anthracnose caused by Colletotrichum destructivum was reported and suggested to be a potential threat to the quality of oil and edible seeds derived from sunflower in the field and even on the ornamentals in the residential gardens. Colletotrichum destructivum, as the causal agent of sunflower anthracnose, has been rarely studied. In this study, the vegetative growth and sporulation of this fungal species were investigated by assessing the requirements of nutrition and other environmental conditions, such as temperature, ambient pH, and lightness regime. Additionally, the sensitivity of C. destructivum to several fungicides was assessed. The results will provide a baseline for better understanding of the biology and etiology of C. destructivum. This study will be the first reference for a sustainable management strategy according to the occurrence and prevalence of the sunflower anthracnose.


Asunto(s)
Colletotrichum/crecimiento & desarrollo , Fungicidas Industriales/farmacología , Helianthus/microbiología , Enfermedades de las Plantas/microbiología , Esporas Fúngicas/crecimiento & desarrollo , Colletotrichum/clasificación , Colletotrichum/efectos de los fármacos , Colletotrichum/aislamiento & purificación
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