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Medicinas Complementárias
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1.
Molecules ; 27(3)2022 Feb 08.
Artículo en Inglés | MEDLINE | ID: mdl-35164398

RESUMEN

Fungal infections of cultivated food crops result in extensive losses of crops at the global level, while resistance to antifungal agents continues to grow. Supercritical fluid extraction using CO2 (SFE-CO2) has gained attention as an environmentally well-accepted extraction method, as CO2 is a non-toxic, inert and available solvent, and the extracts obtained are, chemically, of greater or different complexities compared to those of conventional extracts. The SFE-CO2 extracts of Achillea millefolium, Calendula officinalis, Chamomilla recutita, Helichrysum arenarium, Humulus lupulus, Taraxacum officinale, Juniperus communis, Hypericum perforatum, Nepeta cataria, Crataegus sp. and Sambucus nigra were studied in terms of their compositions and antifungal activities against the wheat- and buckwheat-borne fungi Alternaria alternata, Epicoccum nigrum, Botrytis cinerea, Fusarium oxysporum and Fusarium poae. The C. recutita and H. arenarium extracts were the most efficacious, and these inhibited the growth of most of the fungi by 80% to 100%. Among the fungal species, B. cinerea was the most susceptible to the treatments with the SFE-CO2 extracts, while Fusarium spp. were the least. This study shows that some of these SFE-CO2 extracts have promising potential for use as antifungal agents for selected crop-borne fungi.


Asunto(s)
Fungicidas Industriales/química , Fungicidas Industriales/farmacología , Enfermedades de las Plantas/prevención & control , Extractos Vegetales/química , Extractos Vegetales/farmacología , Botrytis/efectos de los fármacos , Dióxido de Carbono/química , Cromatografía con Fluido Supercrítico/métodos , Productos Agrícolas/microbiología , Fagopyrum/microbiología , Hongos/efectos de los fármacos , Fungicidas Industriales/aislamiento & purificación , Enfermedades de las Plantas/microbiología , Extractos Vegetales/aislamiento & purificación , Triticum/microbiología
2.
Eur J Med Chem ; 227: 113937, 2022 Jan 05.
Artículo en Inglés | MEDLINE | ID: mdl-34710744

RESUMEN

Evodiamine and rutaecarpine are two alkaloids isolated from traditional Chinese herbal medicine Evodia rutaecarpa, which have been reported to have various biological activities in past decades. To explore the potential applications for evodiamine and rutaecarpine alkaloids and their derivatives, various kinds of evodiamine and rutaecarpine derivatives were designed and synthesized. Their antifungal profile against six phytopathogenic fungi Rhizoctonia solani, Botrytis cinerea, Fusarium graminearum, Fusarium oxysporum, Sclerotinia sclerotiorum, and Magnaporthe oryzae were evaluated for the first time. Furthermore, a series of modified imidazole derivatives of rutaecarpine were synthesized to investigate the structure-activity relationship. The results of antifungal activities in vitro showed that imidazole derivative of rutaecarpine A1 exhibited broad-spectrum inhibitory activities against R. solani, B. cinerea, F. oxysporum, S. sclerotiorum, M. oryzae and F. graminearum with EC50 values of 1.97, 5.97, 12.72, 2.87 and 16.58 µg/mL, respectively. Preliminary mechanistic studies showed that compound A1 might cause mycelial abnormalities of S. sclerotiorum, mitochondrial distortion and swelling, and inhibition of sclerotia formation and germination. Moreover, the curative effects of compound A1 were 94.7%, 81.5%, 80.8%, 65.0% at 400, 200, 100, 50 µg/mL in vivo experiments, which was far more effective than the positive control azoxystrobin. Significantly, no phytotoxicity of compound A1 on oilseed rape leaves was observed obviously even at a high concentration of 400 µg/mL. Therefore, compound A1 is expected to be a novel leading structure for the development of new antifungal agents.


Asunto(s)
Antifúngicos/farmacología , Diseño de Fármacos , Alcaloides Indólicos/farmacología , Quinazolinas/farmacología , Antifúngicos/síntesis química , Antifúngicos/química , Ascomicetos/efectos de los fármacos , Botrytis/efectos de los fármacos , Relación Dosis-Respuesta a Droga , Fusarium/efectos de los fármacos , Alcaloides Indólicos/síntesis química , Alcaloides Indólicos/química , Pruebas de Sensibilidad Microbiana , Estructura Molecular , Quinazolinas/síntesis química , Quinazolinas/química , Rhizoctonia/efectos de los fármacos , Relación Estructura-Actividad
3.
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
4.
Biomed Res Int ; 2021: 9930210, 2021.
Artículo en Inglés | MEDLINE | ID: mdl-34395628

RESUMEN

The present study was aimed at isolating endophytic fungi from the Asian culinary and medicinal plant Lilium davidii and analyzing its antifungal and plant growth-promoting effects. In this study, the fungal endophyte Acremonium sp. Ld-03 was isolated from the bulbs of L. davidii and identified through morphological and molecular analysis. The molecular and morphological analysis confirmed the endophytic fungal strain as Acremonium sp. Ld-03. Antifungal effects of Ld-03 were observed against Fusarium oxysporum, Botrytis cinerea, Botryosphaeria dothidea, and Fusarium fujikuroi. The highest growth inhibition, i.e., 78.39 ± 4.21%, was observed for B. dothidea followed by 56.68 ± 4.38%, 43.62 ± 3.81%, and 20.12 ± 2.45% for B. cinerea, F. fujikuroi, and F. oxysporum, respectively. Analysis of the ethyl acetate fraction through UHPLC-LTQ-IT-MS/MS revealed putative secondary metabolites which included xanthurenic acid, valyl aspartic acid, gancidin W, peptides, and cyclic dipeptides such as valylarginine, cyclo-[L-(4-hydroxy-Pro)-L-leu], cyclo(Pro-Phe), and (3S,6S)-3-benzyl-6-(4-hydroxybenzyl)piperazine-2,5-dione. Other metabolites included (S)-3-(4-hydroxyphenyl)-2-((S)-pyrrolidine-2-carboxamido)propanoic acid, dibutyl phthalate (DBP), 9-octadecenamide, D-erythro-C18-Sphingosine, N-palmitoyl sphinganine, and hydroxypalmitoyl sphinganine. The strain Ld-03 showed indole acetic acid (IAA) production with or without the application of exogenous tryptophan. The IAA ranged from 53.12 ± 3.20 µg ml-1 to 167.71 ± 7.12 µg ml-1 under different tryptophan concentrations. The strain was able to produce siderophore, and its production was significantly decreased with increasing Fe(III) citrate concentrations in the medium. The endophytic fungal strain also showed production of organic acids and phosphate solubilization activity. Plant growth-promoting effects of the strain were evaluated on in vitro seedling growth of Allium tuberosum. Application of 40% culture dilution resulted in a significant increase in root and shoot length, i.e., 24.03 ± 2.71 mm and 37.27 ± 1.86 mm, respectively, compared to nontreated control plants. The fungal endophyte Ld-03 demonstrated the potential of conferring disease resistance and plant growth promotion. Therefore, we conclude that the isolated Acremonium sp. Ld-03 should be further investigated before utilization as a biocontrol agent and plant growth stimulator.


Asunto(s)
Acremonium/química , Antifúngicos/farmacología , Ascomicetos/crecimiento & desarrollo , Botrytis/crecimiento & desarrollo , Fusarium/crecimiento & desarrollo , Lilium/microbiología , Reguladores del Crecimiento de las Plantas/farmacología , Acetatos/química , Acetatos/farmacología , Acremonium/aislamiento & purificación , Acremonium/fisiología , Antifúngicos/química , Ascomicetos/efectos de los fármacos , Botrytis/efectos de los fármacos , Cebollino/efectos de los fármacos , Cebollino/crecimiento & desarrollo , Cromatografía Líquida de Alta Presión , Resistencia a la Enfermedad , Endófitos/aislamiento & purificación , Endófitos/fisiología , Fusarium/efectos de los fármacos , Ácidos Indolacéticos/química , Ácidos Indolacéticos/aislamiento & purificación , Ácidos Indolacéticos/farmacología , Metabolómica/métodos , Pruebas de Sensibilidad Microbiana , Viabilidad Microbiana/efectos de los fármacos , Desarrollo de la Planta , Reguladores del Crecimiento de las Plantas/química , Reguladores del Crecimiento de las Plantas/aislamiento & purificación , Raíces de Plantas/microbiología , Metabolismo Secundario , Espectrometría de Masas en Tándem
5.
Molecules ; 26(15)2021 Jul 29.
Artículo en Inglés | MEDLINE | ID: mdl-34361746

RESUMEN

New agricultural strategies aim to reduce the use of pesticides due to their damage to the environment and humans, and the caused resistance to pathogens. Therefore, alternative sources of antifungal compounds from plants are under investigation lately. Extracts from plants have a wide composition of chemical compounds which may complicate the development of pathogen resistance. Botrytis cinerea, causing grey mould, is an important horticultural and ornamental pathogen, responsible for the relevant yield and quality losses. B. cinerea isolated from a different plant host may differ in the sensitivity to antifungal substances from plants. Assessing the importance of research covering a wide range of pathogens for the rapid development of biopesticides, this study aims to determine the sensitivity of the B. cinerea isolate complex (10 strains) to plant extracts, describe morphological changes caused by the extract treatment, and detect differences between the sensitivity of different plant host isolates. The results showed the highest sensitivity of the B. cinerea isolates complex to cinnamon extract, and the lowest to laurel extract. In contrast, laurel extract caused the most changes of morphological attributes in the isolates. Five B. cinerea isolates from plant hosts of raspberry, cabbage, apple, bell pepper, and rose were grouped statistically according to their sensitivity to laurel extract. Meanwhile, the bell pepper isolate separated from the isolate complex based on its sensitivity to clove extract, and the strawberry and apple isolates based on their sensitivity to cinnamon extract.


Asunto(s)
Antifúngicos/farmacología , Agentes de Control Biológico/farmacología , Botrytis/efectos de los fármacos , Cinnamomum zeylanicum/química , Hifa/efectos de los fármacos , Enfermedades de las Plantas/prevención & control , Antifúngicos/aislamiento & purificación , Agentes de Control Biológico/aislamiento & purificación , Botrytis/crecimiento & desarrollo , Botrytis/aislamiento & purificación , Brassica/microbiología , Capsicum/microbiología , Cinnamomum camphora/química , Fragaria/microbiología , Humanos , Hifa/crecimiento & desarrollo , Hifa/aislamiento & purificación , Malus/microbiología , Pruebas de Sensibilidad Microbiana , Enfermedades de las Plantas/microbiología , Extractos Vegetales/química , Syzygium/química , Vitis/microbiología
6.
Molecules ; 26(11)2021 Jun 02.
Artículo en Inglés | MEDLINE | ID: mdl-34199618

RESUMEN

This study determined the antimicrobial and antioxidant activity of lemongrass (LO), thyme (TO), and oregano (OO) essential oils and ethanolic extracts of pomegranate peel (PPE) and grape pomace (GPE) as candidate ingredients for edible coatings. Antifungal effects against Botrytis cinerea and Penicillium spp. were tested using paper disc and well diffusion methods. Radical scavenging activity (RSA) was evaluated using 2,2-diphenyl-1-picrylhydrazyl and 2,2'-azinobis-3-ethylbenzothiazoline-6-sulfonic acid assays. Gas chromatography-mass spectrometry analysis identified limonene (16.59%), α-citral (27.45%), ß-citral (27.43%), thymol (33.31%), paracymene (43.26%), 1,8-cineole (17.53%), and trans-caryphellene (60.84%) as major compounds of the essential oils. From both paper disc and well diffusion methods, LO recorded the widest zone of inhibition against tested microbes (B. cinerea and Penicillium spp.). The minimum inhibitory concentrations of LO against B. cinerea and Penicillium spp., were 15 µL/mL and 30 µL/mL, respectively. The highest (69.95%) and lowest (1.64%) RSA at 1 mg/mL were recorded for PPE and OO. Application of sodium alginate and chitosan-based coatings formulated with LO (15 or 30 µL/mL) completely inhibited spore germination and reduced the decay severity of 'Wonderful' pomegranate. Lemongrass oil proved to be a potential antifungal agent for edible coatings developed to extend shelf life of 'Wonderful' pomegranate.


Asunto(s)
Antiinfecciosos/farmacología , Antioxidantes/farmacología , Cymbopogon/química , Aceites Volátiles/farmacología , Origanum/química , Thymus (Planta)/química , Antiinfecciosos/química , Antioxidantes/química , Botrytis/efectos de los fármacos , Cromatografía de Gases y Espectrometría de Masas , Pruebas de Sensibilidad Microbiana , Aceites Volátiles/química , Penicillium/efectos de los fármacos , Aceites de Plantas/química , Aceites de Plantas/farmacología , Esporas Fúngicas/efectos de los fármacos , Terpenos
7.
Fungal Biol ; 125(2): 143-152, 2021 02.
Artículo en Inglés | MEDLINE | ID: mdl-33518204

RESUMEN

There is a growing interest in finding safe and natural anti-microbial compounds as a valid alternative to conventional chemical treatments for managing post-harvest fruit diseases. This study investigated the anti-fungal capacity of orange peel polyphenolic extract (OPE) against three relevant post-harvest fungal pathogens, Monilinia fructicola, Botrytis cinerea and Alternaria alternata. OPE extract at 1.5 g/L inhibited (100%) the mycelial growth and conidial germination of the three target fungi. At lower concentration, the effect varied, depending on the dose applied and target fungi. When the anti-fungal activity of the main phenolic compounds in sweet orange peel, namely, the flavonoids (naringin, hesperidin and neohesperidin) and phenolic acids (ferulic and p-coumaric), were evaluated, ferulic acid and p-coumaric acid displayed significantly higher inhibitory capacity in synthetic medium, while the activity of flavonoids was limited. Synergism between compounds was not detected, and the inhibitory activity of OPE may be attributed to an additive effect of phenolic acids. Interestingly, in peach-based medium, ferulic acid remained active against M. fructicola and A. alternata and was more efficient than p-coumaric to control B. cinerea. These results highlight peel orange waste as an excellent source of anti-fungal compounds, suggesting the possibility of using ferulic acid or ferulic acid-rich extracts, either alone or in combination with other post-harvest treatment, as a natural alternative to reduce post-harvest losses and, also, enhance the shelf-life of fruit.


Asunto(s)
Citrus sinensis , Microbiología de Alimentos , Frutas , Hongos , Extractos Vegetales , Alternaria/efectos de los fármacos , Ascomicetos/efectos de los fármacos , Botrytis/efectos de los fármacos , Citrus sinensis/química , Frutas/química , Frutas/microbiología , Hongos/efectos de los fármacos , Fenol/química , Extractos Vegetales/farmacología
8.
Plant J ; 105(5): 1309-1325, 2021 03.
Artículo en Inglés | MEDLINE | ID: mdl-33617106

RESUMEN

Secretions from glandular trichomes potentially protect plants against a variety of aggressors. In the tomato clade of the Solanum genus, glandular trichomes of wild species produce a rich source of chemical diversity at the leaf surface. Previously, 7-epi-zingiberene produced in several accessions of Solanum habrochaites was found to confer resistance to whiteflies (Bemisia tabaci) and other insect pests. Here, we report the identification and characterisation of 9-hydroxy-zingiberene (9HZ) and 9-hydroxy-10,11-epoxyzingiberene (9H10epoZ), two derivatives of 7-epi-zingiberene produced in glandular trichomes of S. habrochaites LA2167. Using a combination of transcriptomics and genetics, we identified a gene coding for a cytochrome P450 oxygenase, ShCYP71D184, that is highly expressed in trichomes and co-segregates with the presence of the zingiberene derivatives. Transient expression assays in Nicotiana benthamiana showed that ShCYP71D184 carries out two successive oxidations to generate 9HZ and 9H10epoZ. Bioactivity assays showed that 9-hydroxy-10,11-epoxyzingiberene in particular exhibits substantial toxicity against B. tabaci and various microorganisms including Phytophthora infestans and Botrytis cinerea. Our work shows that trichome secretions from wild tomato species can provide protection against a wide variety of organisms. In addition, the availability of the genes encoding the enzymes for the pathway of 7-epi-zingiberene derivatives makes it possible to introduce this trait in cultivated tomato by precision breeding.


Asunto(s)
Hemípteros/metabolismo , Sesquiterpenos Monocíclicos/metabolismo , NADPH-Ferrihemoproteína Reductasa/metabolismo , Solanum/metabolismo , Animales , Botrytis/efectos de los fármacos , Botrytis/patogenicidad , Hemípteros/genética , Hemípteros/microbiología , Sesquiterpenos Monocíclicos/toxicidad , NADPH-Ferrihemoproteína Reductasa/genética , Phytophthora infestans/efectos de los fármacos , Phytophthora infestans/patogenicidad , Solanum/genética
9.
Mol Genet Genomics ; 296(1): 131-140, 2021 Jan.
Artículo en Inglés | MEDLINE | ID: mdl-33052533

RESUMEN

Aegerolysins are small secreted pore-forming proteins that are found in both prokaryotes and eukaryotes. The role of aegerolysins in sporulation, fruit body formation, and in lysis of cellular membrane is suggested in fungi. The aim of the present study was to characterize the biological function of the aegerolysin gene agl1 in the mycoparasitic fungus Trichoderma atroviride, used for biological control of plant diseases. Gene expression analysis showed higher expression of agl1 during conidiation and during growth in medium supplemented with cell wall material from the plant pathogenic fungus Rhizoctonia solani as the sole carbon source. Expression of agl1 was supressed under iron-limiting condition, while agl1 transcript was not detected during T. atroviride interactions with the prey fungi Botrytis cinerea or R. solani. Phenotypic analysis of agl1 deletion strains (Δagl1) showed reduced conidiation compared to T. atroviride wild type, thus suggesting the involvement of AGL1 in conidiation. Furthermore, the Δagl1 strains display reduced antagonism towards B. cinerea and R. solani based on a secretion assay, although no difference was detected during direct interactions. These data demonstrate the role of AGL1 in conidiation and antagonism in the mycoparasitic fungus T. atroviride.


Asunto(s)
Antibiosis/genética , Cuerpos Fructíferos de los Hongos/genética , Proteínas Fúngicas/genética , Regulación Fúngica de la Expresión Génica , Proteínas Hemolisinas/genética , Hypocreales/genética , Esporas Fúngicas/genética , Botrytis/efectos de los fármacos , Botrytis/crecimiento & desarrollo , Pared Celular/química , Mezclas Complejas/farmacología , Cuerpos Fructíferos de los Hongos/efectos de los fármacos , Cuerpos Fructíferos de los Hongos/metabolismo , Cuerpos Fructíferos de los Hongos/patogenicidad , Proteínas Fúngicas/metabolismo , Proteínas Fúngicas/toxicidad , Proteínas Hemolisinas/metabolismo , Proteínas Hemolisinas/toxicidad , Hypocreales/efectos de los fármacos , Hypocreales/metabolismo , Hypocreales/patogenicidad , Deficiencias de Hierro , Filogenia , Enfermedades de las Plantas/microbiología , ARN Mensajero/genética , ARN Mensajero/metabolismo , Rhizoctonia/efectos de los fármacos , Rhizoctonia/crecimiento & desarrollo , Solanum tuberosum/microbiología , Esporas Fúngicas/efectos de los fármacos , Esporas Fúngicas/metabolismo , Esporas Fúngicas/patogenicidad
10.
Fitoterapia ; 148: 104778, 2021 Jan.
Artículo en Inglés | MEDLINE | ID: mdl-33242534

RESUMEN

Four new meroterpenes named as guignardones U-X (1-4), along with eleven known meroterpenes (5-15) and three known dioxolanone derivatives (16-18), were obtained from the endophytic fungus Phyllosticta sp. WGHL2. The structural elucidation was conducted by HRESIMS, NMR, single crystal X-ray diffraction, along with ECD calculations and comparison. In antifungal tests, compound 16 possessed broad-spectrum antifungal activities against Rhizoctonia solani, Fusarium graminearum and Botrytis cinerea with inhibition ratio of 48.43%, 40.98%, and 49.53% at 50 µg/mL, respectively. Moreover, compound 16 showed moderate protective effect against B. cinerea in vivo at 200 µg/mL and exhibited effective inhibition on the spore germination of B. cinerea.


Asunto(s)
Ascomicetos/química , Botrytis/efectos de los fármacos , Fungicidas Industriales/farmacología , Fusarium/efectos de los fármacos , Rhizoctonia/efectos de los fármacos , China , Endófitos/química , Fungicidas Industriales/aislamiento & purificación , Pruebas de Sensibilidad Microbiana , Estructura Molecular , Oleaceae/microbiología
11.
Molecules ; 25(20)2020 Oct 16.
Artículo en Inglés | MEDLINE | ID: mdl-33081360

RESUMEN

The aim of this work was to evaluate the antifungal activity in vapor phase of thymol, p-cymene, and γ-terpinene, the red thyme essential oil compounds (RTOCs). The Minimum Inhibitory Concentration (MIC) of RTOCs was determined against postharvest spoilage fungi of the genera Botrytis, Penicillium, Alternaria, and Monilinia, by measuring the reduction of the fungal biomass after exposure for 72 h at 25 °C. Thymol showed the lowest MIC (7.0 µg/L), followed by γ-terpinene (28.4 µg/L) and p-cymene (40.0 µg/L). In the case of P. digitatum ITEM 9569, resistant to commercial RTO, a better evaluation of interactions among RTOCs was performed using the checkerboard assay and the calculation of the Fractional Inhibitory Concentration Index (FICI). During incubation, changes in the RTOCs concentration were measured by GC-MS analysis. A synergistic effect between thymol (0.013 ± 0.003 L/L) and γ-terpinene (0.990 ± 0.030 L/L) (FICI = 0.50) in binary combinations, and between p-cymene (0.700 ± 0.010 L/L) and γ-terpinene (0.290 ± 0.010 L/L) in presence of thymol (0.008 ± 0.001 L/L) (FICI = 0.19), in ternary combinations was found. The synergistic effect against the strain P. digitatum ITEM 9569 suggests that different combinations among RTOCs could be defined to control fungal strains causing different food spoilage phenomena.


Asunto(s)
Antifúngicos/química , Aceites Volátiles/farmacología , Aceites de Plantas/química , Thymus (Planta)/química , Antifúngicos/farmacología , Botrytis/efectos de los fármacos , Botrytis/patogenicidad , Sinergismo Farmacológico , Cromatografía de Gases y Espectrometría de Masas , Pruebas de Sensibilidad Microbiana , Monoterpenos/química , Monoterpenos/farmacología , Aceites Volátiles/química , Penicillium/efectos de los fármacos , Penicillium/patogenicidad , Aceites de Plantas/farmacología
12.
J Agric Food Chem ; 68(24): 6739-6747, 2020 Jun 17.
Artículo en Inglés | MEDLINE | ID: mdl-32379969

RESUMEN

This study aimed to reveal the effects and possible mechanism of terpinen-4-ol, the main component of tea tree oil (TTO), on the disease resistance of strawberry fruit. When the effects of TTO and its components were compared on the decay development in fruit inoculated with Botrytis cinerea after treatment, strawberry treated with terpinen-4-ol showed the lowest disease incidence (44.4%) after 48 h and also the smallest lesion diameter during the whole storage. This indicates that terpinen-4-ol induces the highest disease resistance in strawberry compared with TTO and other components. Untargeted metabolomic analysis showed that terpinen-4-ol treatment strongly activated phenylpropanoid biosynthesis and flavonoid metabolism pathway by increasing the accumulation of cinnamaldehyde, coniferyl aldehyde, naringenin, taxifolin, quercetin, and quercitrin in fruit at 12 h after treatment. In addition, terpinen-4-ol treatment also caused the accumulation of total phenolics and lignin by enhancing activities and relative gene expression of key enzymes in the phenylpropanoid metabolism pathway. These results suggest that terpinen-4-ol, as the key component of TTO, is the most important contributor to the effectiveness of TTO in improving disease resistance of strawberry fruit through activating the phenylpropanoid metabolism pathway.


Asunto(s)
Antifúngicos/farmacología , Fragaria/microbiología , Fenilpropionatos/inmunología , Enfermedades de las Plantas/inmunología , Aceite de Árbol de Té/farmacología , Terpenos/farmacología , Botrytis/efectos de los fármacos , Botrytis/crecimiento & desarrollo , Resistencia a la Enfermedad , Fragaria/inmunología , Frutas/inmunología , Frutas/microbiología , Pruebas de Sensibilidad Microbiana , Enfermedades de las Plantas/microbiología
13.
Molecules ; 25(6)2020 Mar 13.
Artículo en Inglés | MEDLINE | ID: mdl-32182987

RESUMEN

The aim of this paper is to evaluate the physicochemical and microbiological properties of active thermoplastic starch-based materials. The extract obtained from grape cane waste was used as a source of stilbene bioactive components to enhance the functional properties of thermoplastic starch (TPS). The biomaterials were prepared by the compression molding technique and subjected to mechanical, thermal, antioxidant, and microbiological tests. The results showed that the addition of grape cane extract up to 15 wt% (TPS/WE15) did not significantly influence the thermal stability of obtained biomaterials, whereas mechanical resistance decreased. On the other side, among all tested pathogens, thermoplastic starch based materials showed antifungal activity toward Botrytis cinerea and antimicrobial activity toward Staphylococcus aureus, suggesting potential application in food packaging as an active biomaterial layer.


Asunto(s)
Embalaje de Alimentos , Extractos Vegetales/química , Plásticos/química , Almidón/química , Temperatura , Vitis/química , Antioxidantes/análisis , Botrytis/efectos de los fármacos , Botrytis/crecimiento & desarrollo , Pruebas de Sensibilidad Microbiana , Extractos Vegetales/farmacología , Espectroscopía Infrarroja por Transformada de Fourier , Staphylococcus aureus/efectos de los fármacos , Almidón/farmacología , Termogravimetría
14.
Bioorg Chem ; 97: 103696, 2020 04.
Artículo en Inglés | MEDLINE | ID: mdl-32135360

RESUMEN

Xanthatin, a natural sesquiterpene lactone, occurs as one of the major constituents of Xanthium plants (Compositae) and exhibits many important biological properties. To discover natural products-based pesticides, forty-nine Michael-type thiol/amino adducts of xanthatin were synthesized and characterized, while their pesticidal activities were investigated. Among them, compounds 2c, 2h, 2i, and 2t exhibited more potent antifungal activity against Botrytis cinerea (IC50 = 0.96, 0.38, 6.33, and 7.21 µg/mL, respectively) than xanthatin and the two commercial fungicides. Compounds 2t and 2u displayed broad-spectrum and excellent antifungal effects against all tested phytopathogenic fungi, while their IC50 values ranged from 7.21 to 75.88 µg/mL. Compounds 2a, 2f, 2l, 2m, 2v, 7c, 7e, 7h, 7i, and 7j showed moderate larvicidal activity against Plutella xylostella Linnaeus. Furthermore, compounds 2b, 7g, and 7h demonstrated significant ovicidal activity against P. xylostella with the LC50 values of 14.04, 10.00, and 11.95 mg/L, respectively. These findings suggest that thiol/amino appended in the C-13 position of xanthatin may improve antifungal and ovicidal activities for the derivatives. It was also noticed that the exocyclic double bond of xanthatin is crucial for its larvicidal activity. This work also provides some important hints for further design, synthesis, and structural modification of the xanthanolides sesquiterpene lactones toward development of the new environmentally friendly pesticides for sustainable agricultural production.


Asunto(s)
Botrytis/efectos de los fármacos , Fungicidas Industriales/toxicidad , Furanos/toxicidad , Enfermedades de las Plantas/microbiología , Xanthium/química , Aminación , Fungicidas Industriales/síntesis química , Fungicidas Industriales/química , Furanos/síntesis química , Furanos/química , Modelos Moleculares , Enfermedades de las Plantas/prevención & control , Compuestos de Sulfhidrilo/síntesis química , Compuestos de Sulfhidrilo/química , Compuestos de Sulfhidrilo/toxicidad
15.
J Agric Food Chem ; 68(8): 2306-2315, 2020 Feb 26.
Artículo en Inglés | MEDLINE | ID: mdl-31995378

RESUMEN

Neocryptolepine is an alkaloid isolated from traditional African herbal medicine Cryptolepis sanguinolenta, and its broad spectrum of biological activities has been illuminated in past decades. In this study, neocryptolepine and its derivatives (1-49) were designed and synthesized from economical and readily available starting materials. Their structures were confirmed by proton nuclear magnetic resonance, carbon nuclear magnetic resonance, and mass spectrometry. The synthesized compounds were screened for their antifungal profile against six agriculturally important fungi Rhizoctonia solani, Botrytis cinerea (B. cinerea), Fusarium graminearum, Mycosphaerella melonis, Sclerotinia sclerotiorum, and Magnaporthe oryzae. The results of in vitro assay revealed that compounds 5, 21, 24, 35, 40, 45, and 47 presented remarkable antifungal activity against the fungi tested with EC50 values lower than 1 µg/mL. Significantly, compound 24 displayed the most effective inhibitory potency against B. cinerea (EC50 = 0.07 µg/mL), and the data from in vivo experiments revealed that compound 24 demonstrated comparable protective activity with the positive control boscalid. Preliminary mechanism studies indicated that compound 24 showed impressive spore germination inhibitory effectiveness and lower cytotoxicity than azoxystrobin, imparted on normal function of the cell membrane and cell wall, and arrested the normal function of the nucleus. Besides the excellent inhibitory activity against agriculturally important phytopathogenic fungi tested, the designed assemblage possesses several benefits with a high profile of variation in synthesized molecules, the ease of synthesis, and good cost-effectiveness of commercially available synthetic reagents, all of these have highlighted the potential worth of compound 24 as a new and highly efficient agricultural fungicide.


Asunto(s)
Antifúngicos/farmacología , Fungicidas Industriales/farmacología , Enfermedades de las Plantas/microbiología , Antifúngicos/síntesis química , Antifúngicos/química , Botrytis/efectos de los fármacos , Botrytis/crecimiento & desarrollo , Fungicidas Industriales/síntesis química , Fungicidas Industriales/química , Fusarium/efectos de los fármacos , Fusarium/crecimiento & desarrollo , Estructura Molecular , Rhizoctonia/efectos de los fármacos , Rhizoctonia/crecimiento & desarrollo , Relación Estructura-Actividad
16.
Appl Microbiol Biotechnol ; 104(5): 2163-2178, 2020 Mar.
Artículo en Inglés | MEDLINE | ID: mdl-31980918

RESUMEN

Tea tree oil (TTO) and its two characteristic components (terpinen-4-ol and 1,8-cineole) have been shown to inhibit Botrytis cinerea growth. In this study, we conducted a transcriptome analysis to determine the effects of TTO and its characteristic components, alone and in combination, against B. cinerea. Most differentially expressed genes (DEGs) from B. cinerea cells treated with terpinen-4-ol participated in the biosynthesis of secondary metabolites, and the metabolism of amino acids, carbohydrates, and lipids. All treatments containing terpinen-4-ol potentially induced mitochondrial dysfunction and oxidative stress. These were further confirmed by the decreased activities of several enzymes (e.g., succinate dehydrogenase (SDH), malate dehydrogenase (MDH), α-ketoglutarate dehydrogenase (α-KGDH), isocitrate dehydrogenase (ICDH)), the increased activities of certain enzymes (e.g., catalase (CAT), peroxidase (POD), superoxide dismutase (SOD)), and increased content of hydrogen peroxide (H2O2). 1,8-Cineole mainly affected DEGs involved in genetic information processing, resulting in cell death. This study provides insight into the molecular mechanism of B. cinerea inhibition by TTO, and explains the synergistic effect of terpinen-4-ol and 1,8-cineole on B. cinerea.


Asunto(s)
Antifúngicos/farmacología , Botrytis/efectos de los fármacos , Botrytis/genética , Aceite de Árbol de Té/farmacología , Antifúngicos/química , Botrytis/crecimiento & desarrollo , Sinergismo Farmacológico , Eucaliptol/farmacología , Proteínas Fúngicas/genética , Proteínas Fúngicas/metabolismo , Perfilación de la Expresión Génica , Peróxido de Hidrógeno/metabolismo , Aceite de Árbol de Té/química , Terpenos/farmacología , Transcriptoma/efectos de los fármacos
17.
Curr Protein Pept Sci ; 21(5): 497-506, 2020.
Artículo en Inglés | MEDLINE | ID: mdl-31746293

RESUMEN

Latex, a milky fluid found in several plants, is widely used for many purposes, and its proteins have been investigated by researchers. Many studies have shown that latex produced by some plant species is a natural source of biologically active compounds, and many of the hydrolytic enzymes are related to health benefits. Research on the characterization and industrial and pharmaceutical utility of latex has progressed in recent years. Latex proteins are associated with plants' defense mechanisms, against attacks by fungi. In this respect, there are several biotechnological applications of antifungal proteins. Some findings reveal that antifungal proteins inhibit fungi by interrupting the synthesis of fungal cell walls or rupturing the membrane. Moreover, both phytopathogenic and clinical fungal strains are susceptible to latex proteins. The present review describes some important features of proteins isolated from plant latex which presented in vitro antifungal activities: protein classification, function, molecular weight, isoelectric point, as well as the fungal species that are inhibited by them. We also discuss their mechanisms of action.


Asunto(s)
Antifúngicos/farmacología , Quitinasas/farmacología , Látex/química , Péptido Hidrolasas/farmacología , Peroxidasas/farmacología , Lectinas de Plantas/farmacología , Proteínas de Plantas/farmacología , Antifúngicos/clasificación , Antifúngicos/aislamiento & purificación , Botrytis/efectos de los fármacos , Botrytis/crecimiento & desarrollo , Candida albicans/efectos de los fármacos , Candida albicans/crecimiento & desarrollo , Quitinasas/clasificación , Quitinasas/aislamiento & purificación , Quitinasas/fisiología , Fusarium/efectos de los fármacos , Fusarium/crecimiento & desarrollo , Punto Isoeléctrico , Pruebas de Sensibilidad Microbiana , Peso Molecular , Péptido Hidrolasas/clasificación , Péptido Hidrolasas/aislamiento & purificación , Péptido Hidrolasas/fisiología , Peroxidasas/clasificación , Peroxidasas/aislamiento & purificación , Peroxidasas/fisiología , Enfermedades de las Plantas/microbiología , Extractos Vegetales/química , Lectinas de Plantas/clasificación , Lectinas de Plantas/aislamiento & purificación , Lectinas de Plantas/fisiología , Proteínas de Plantas/clasificación , Proteínas de Plantas/aislamiento & purificación , Proteínas de Plantas/fisiología , Plantas/química
18.
Zhongguo Zhong Yao Za Zhi ; 44(18): 3954-3959, 2019 Sep.
Artículo en Chino | MEDLINE | ID: mdl-31872730

RESUMEN

Through investigation,it was found that the main disease of leaves was grey mold on Dendrobium officinale in Hubei province,which has a great impact on the yield and quality of D. officinale. The identification of morphological and molecular biological was used to prove that the pathogen was Botrytis cinerea. Through test the effect of 5 plant source fungicides and 4 antibiotic fungicides on mycelial growth of strain HS1,which proved 0. 3% eugenol had the best inhibitory effect,EC50 was 0. 29 mg·L-1,the second was1% osthol and EC50 was 1. 12 mg·L-1,the EC50 of 0. 5% matrine was 9. 16 mg·L-1,the EC50 of the other six fungicides was higher than 10 mg·L-1. The field control effect test proved that 0. 3% eugenol had the best control effect,reaching 89. 44%,secondly for 1%osthole,which was 77. 17%,0. 5% matrine was in the third place with 62. 37% of effective rate. However,the control effect of the other fungicides was less than 60%. The three plant-derived fungicides were safe for the produce of D. officinale and showed no phytotoxicity. The effect of these fungicides on the growth of D. candidum was tested,and proved that all the fungicides were safe and harmless to D. candidum. This study provides a research basis for the safe and effective prevention and control gray mold of D. officinale.


Asunto(s)
Botrytis/patogenicidad , Dendrobium/microbiología , Fungicidas Industriales , Enfermedades de las Plantas/microbiología , Alcaloides , Botrytis/efectos de los fármacos , Cumarinas , Eugenol , Enfermedades de las Plantas/prevención & control , Hojas de la Planta/microbiología , Quinolizinas , Matrinas
19.
J Sci Food Agric ; 99(14): 6552-6561, 2019 Nov.
Artículo en Inglés | MEDLINE | ID: mdl-31321781

RESUMEN

BACKGROUND: Essential oils (EOs) are volatile natural compounds produced by plant secondary metabolism, and some of them exhibit antimicrobial activity. The objective of the present study was to determine the chemical composition the EOs of Eucalyptus staigeriana and Eucalyptus globulus, and their effect in vitro and in vivo against Botrytis cinerea and Colletotrichum acutatum, the most important fungal rot diseases of grapes. Moreover, grapes collected from field experiments were used to evaluate the impact of the alternative control on the alcoholic fermentation and wine composition. RESULTS: The major compound of E. staigeriana EO were citral 30.91% (19.74% geranial, 11.17% neral), 1.8-cineole (24.59%) and limonene (19.47%), while 1.8-cineole represented 68.26% of E. globulus EO. The two EOs showed in vitro antifungal activity against both pathogens. Eucalyptus staigeriana EO exhibited the highest activity inhibiting mycelial growth (MG) and conidial germination at 0.5 µL mL-1 . Moreover, this EO was able to reduce the incidence and severity of grey rot caused by B. cinerea and the severity of ripe rot caused by C. acutatum The alternative control did not significantly influence alcoholic fermentation, the physicochemical characteristics, and the volatile composition of wines. CONCLUSION: These results are promising and indicate that E. staigeriana EO might be further investigated as a natural alternative for the control of fungal rots on wine grapes. © 2019 Society of Chemical Industry.


Asunto(s)
Antifúngicos/farmacología , Eucalyptus/química , Aceites Volátiles/farmacología , Enfermedades de las Plantas/prevención & control , Extractos Vegetales/farmacología , Vitis/microbiología , Antifúngicos/química , Botrytis/efectos de los fármacos , Botrytis/crecimiento & desarrollo , Colletotrichum/efectos de los fármacos , Colletotrichum/crecimiento & desarrollo , Pruebas de Sensibilidad Microbiana , Micelio/efectos de los fármacos , Micelio/crecimiento & desarrollo , Aceites Volátiles/química , Enfermedades de las Plantas/microbiología , Extractos Vegetales/química
20.
Food Chem ; 293: 263-270, 2019 Sep 30.
Artículo en Inglés | MEDLINE | ID: mdl-31151610

RESUMEN

Gray mold caused by Botrytis cinerea is the most important disease in postharvest tomato fruit. Inducing resistance to fungal pathogens in the harvested fruit and vegetable is a promising approach to control postharvest losses. In the present study, the effect of l-glutamate on induction of resistance to B. cinerea and the underlying mechanisms were investigated. The results indicated that l-glutamate at 100 ppm was effective in reducing the gray mold of tomatoes after inoculation of the pathogen. Gene expressions of nine glutamate receptors, four pathogenesis-related proteins and the content of amino acids were affected by l-glutamate treatment. Furthermore, the metabolites of l-glutamate, including GABA, Met, Lys and Arg, could also induce significant resistance against B. cinerea in tomato fruit. Our findings suggested that l-glutamate treatment may represent a promising method for managing postharvest decay of tomato fruit.


Asunto(s)
Aminoácidos/metabolismo , Botrytis/efectos de los fármacos , Ácido Glutámico/farmacología , Micosis/prevención & control , Enfermedades de las Plantas/prevención & control , Receptores de Glutamato/metabolismo , Solanum lycopersicum/inmunología , Resistencia a la Enfermedad , Frutas/química , Solanum lycopersicum/genética , Solanum lycopersicum/microbiología , Micosis/microbiología , Enfermedades de las Plantas/microbiología , Proteínas de Plantas/genética , Regulación hacia Arriba/efectos de los fármacos
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