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Rice sheath blight, caused by the fungus Rhizoctonia solani, poses a significant threat to rice cultivation globally. This study aimed to investigate the potential mechanisms of action of camphor derivatives against R. solani. Compound 4o exhibited superior fungicidal activities in vitro (EC50 = 6.16 mg/L), and in vivo curative effects (77.5%) at 500 mg/L were significantly (P < 0.01) higher than the positive control validamycin·bacillus (66.1%). Additionally, compound 4o exhibited low cytotoxicity and acute oral toxicity for adult worker honeybees of Apis mellifera L. Mechanistically, compound 4o disrupted mycelial morphology and microstructure, increased cell membrane permeability, and inhibited both PDH and SDH enzyme activities. Molecular docking and molecular dynamics analyses indicated a tight interaction of compound 4o with PDH and SDH active sites. In summary, compound 4o exhibited substantial antifungal efficacy against R. solani, serving as a promising lead compound for further optimization of antifungal agents.
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Alcanfor , Fungicidas Industriales , Simulación del Acoplamiento Molecular , Oryza , Enfermedades de las Plantas , Rhizoctonia , Rhizoctonia/efectos de los fármacos , Oryza/microbiología , Enfermedades de las Plantas/microbiología , Fungicidas Industriales/farmacología , Fungicidas Industriales/química , Animales , Alcanfor/farmacología , Alcanfor/química , Abejas/microbiología , Proteínas Fúngicas/metabolismo , Proteínas Fúngicas/química , Antifúngicos/farmacología , Antifúngicos/química , Antifúngicos/síntesis química , Relación Estructura-ActividadRESUMEN
BACKGROUND: Rice sheath blight caused by Rhizoctonia solani is a severe threat to the yield and quality of rice. Due to the unscientific abuse of common fungicides causing resistance and environmental issues, the development of new fungicides is necessary. In this study, we used citral as the lead compound, designed and synthesized a series of novel citral amide derivatives, and evaluated their antifungal activity and mode of action against R. solani. RESULT: Bioassay results indicated that the antifungal activities of most citral amide derivatives against R. solani were significantly improved compared to citral, with EC50 values ranging from 9.50-27.12 mg L-1. Among them, compound d21 containing the N-(pyridin-4-yl)carboxamide group exhibited in vitro and in vivo fungicidal activities, with curative effects at 500 mg L-1 as effectively as the commercial fungicide validamycin·bacillus. Furthermore, d21 prolonged the lag phase of the growth curve of R. solani, reduced the amount of growth, and inhibited sclerotium germination and formation. Mechanistically, d21 deformed the mycelia, increased cell membrane permeability, and inhibited the activities of antioxidant and tricarboxylic acid cycle (TCA)-related enzymes. Metabolome analysis showed the abundance of some energy-related metabolites within R. solani increased, and simultaneously the antifungal substances secreted by itself reduced. Transcriptome analysis showed that most genes encoding ATP-binding cassette (ABC) transporters and peroxisomes upregulated after the treatment of d21 and cell membrane destruction. CONCLUSION: This study indicates that novel citral amide derivatives possess antifungal activity against R. solani and are expected to develop an alternative option for chemical control of rice sheath blight. © 2024 Society of Chemical Industry.
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Monoterpenos Acíclicos , Amidas , Fungicidas Industriales , Rhizoctonia , Rhizoctonia/efectos de los fármacos , Fungicidas Industriales/farmacología , Fungicidas Industriales/síntesis química , Fungicidas Industriales/química , Monoterpenos Acíclicos/farmacología , Amidas/farmacología , Amidas/química , Amidas/síntesis química , Enfermedades de las Plantas/microbiología , Enfermedades de las Plantas/prevención & control , Antifúngicos/farmacología , Antifúngicos/síntesis química , Antifúngicos/químicaRESUMEN
Background: Plant essential oils have long been regarded as repositories of antimicrobial agents. In recent years, they have emerged as potential alternatives or supplements to antimicrobial drugs. Although literature reviews and previous studies have indicated that cinnamon essential oil (CIEO) and its major component, cinnamaldehyde (CID), possess potent antibacterial activities, their antibacterial mechanisms, especially the in vivo antibacterial mechanisms, remain elusive. Methods: In this study, we utilized the in vivo assessment system of Caenorhabditis elegans (C. elegans) to investigate the effects and mechanisms of high dose (100 mg/L) and low dose (10 mg/L) CIEO and CID in inhibiting Pseudomonas aeruginosa (P. aeruginosa). In addition, we also examined the in vitro antibacterial abilities of CIEO and CID against other common pathogens including P. aeruginosa and 4 other strains. Results: Our research revealed that both high (100 mg/L) and low doses (10 mg/L) of CIEO and CID treatment significantly alleviated the reduction in locomotion behavior, lifespan, and accumulation of P. aeruginosa in C. elegans infected with the bacteria. During P. aeruginosa infection, the transcriptional expression of antimicrobial peptide-related genes (lys-1 and lys-8) in C. elegans was upregulated with low-dose CIEO and CID treatment, while this trend was suppressed at high doses. Further investigation suggested that the PMK-1 mediated p38 signaling pathway may be involved in the regulation of CIEO and CID during nematode defense against P. aeruginosa infection. Furthermore, in vitro experimental results also revealed that CIEO and CID exhibit good antibacterial effects, which may be associated with their antioxidant properties. Conclusion: Our results indicated that low-dose CIEO and CID treatment could activate the p38 signaling pathway in C. elegans, thereby regulating antimicrobial peptides, and achieving antimicrobial effects. Meanwhile, high doses of CIEO and CID might directly participate in the internal antimicrobial processes of C. elegans. Our study provides research basis for the antibacterial properties of CIEO and CID both in vivo and in vitro.
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Nanocapsule preparation technology, as an emerging technology with great development prospects, has uniqueness and superiority in various industries. In this paper, the preparation technology of nanocapsules was systematically divided into three categories: physical methods, chemical methods, and physicochemical methods. The technological innovation of different methods in recent years was reviewed, and the mechanisms of nanocapsules prepared via emulsion polymerization, interface polymerization, layer-by-layer self-assembly technology, nanoprecipitation, supercritical fluid, and nano spray drying was summarized in detail. Different from previous reviews, the renewal iteration of core-shell structural materials was highlighted, and relevant illustrations of their representative and latest research results were reviewed. With the continuous progress of nanocapsule technology, especially the continuous development of new wall materials and catalysts, new preparation technology, and new production equipment, nanocapsule technology will be used more widely in medicine, food, cosmetics, pesticides, petroleum products, and many other fields.
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Litsea cubeba (Lour.) Pers. is an important woody spice tree in southern China, and its fruit is a rich source of valuable essential oil. We surveyed and sampled L. cubeba germplasm resources from 36 provenances in nine Chinese provinces, and detected rich phenotypic diversity. The survey results showed that plants of SC-KJ, SC-HJ, and SC-LS provenance presented higher leaf area (LA); YN-SM and YN-XC plants had larger thousand-grain fresh weight (TFW); and HN-DX plants had the highest essential oil content (EOC). To explain the large differences in the phenotypes of L. cubeba among different habitats, we used Pearson's correlation analysis, multiple stepwise regression path analysis, and redundancy analysis to evaluate the phenotypic diversity of L. cubeba. It was found that compared to other traits, leaf and fruit traits had more significant geographical distributions, and that leaf phenotypes were correlated to fruit phenotypes. The results showed that elevation, latitude, longitude, total soil porosity (SP), soil bulk density (SBD), and average annual rainfall (AAR, mm) contributed significantly to the phenotypic diversity of L. cubeba. Geographical factors explained a higher percentage of variation in phenotypic diversity than did soil factors and climate factors. Plants of SC-KJ and HN-DX provenances could be important resources for domestication and breeding to develop new high-yielding varieties of this woody aromatic plant. This study describes significant phenotypic differences in L. cubeba related to adaptation to different environments, and provides a theoretical basis for the development of a breeding strategy and for optimizing L. cubeba cultivation.
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In order to develop a new type of antioxidants with high efficiency, a series of ß-ionone thiazolylhydrazone derivatives were designed and synthesized from ß-ionone, and their structures were characterized by 1H-NMR, 13C-NMR, FT-IR, and HR-MS. The antioxidant test in vitro indicated that most of the target compounds had high biological activity. Among them, compound 1k exhibited very strong DPPH (1,1-diphenyl-2-picrylhydrazyl radical)-scavenging activity with a half-maximal effective concentration (IC50) of 86.525 µM. Furthermore, in the ABTS (2,2-azinobis (3-ethylbenzothiazoline-6-sulfonate) diammonium salt)-scavenging experiment, compound 1m exhibited excellent activity with an IC50 of 65.408 µM. Their biological activities were significantly better than those of the positive control Trolox. These two compounds, which have good free-radical-scavenging activity in vitro, were used as representative compounds in the anti-browning experiment of fresh-cut potatoes. The results showed that 1k and 1m had the same anti-browning ability as kojic acid, and they were effective browning inhibitors. In addition, it is well known that microbial infection is one of the reasons for food oxidation. Therefore, we investigated the antifungal activity of 25 target compounds against eight plant fungi at a concentration of 125 mg/L. The results indicated that these compounds all have some antifungal activity and may become new potential fungicides. Notably, compound 1u showed the best inhibitory effect against Poria vaporaria, with an inhibition rate as high as 77.71%; it is expected to become the dominant structure for the development of new antifungal agents.
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At present, the technology used for the extraction and purification of Camellia oleifera saponins generally has the problems of high cost and low purity, and the quantitative detection of Camellia oleifera saponins also has the problems of low sensitivity and easy interference from impurities. To solve these problems, this paper aimed to use liquid chromatography for the quantitative detection of Camellia oleifera saponins, and to adjust and optimize the related conditions. In our study, the average recovery of Camellia oleifera saponins obtained was 100.42%. The RSD of precision test was 0.41%. The RSD of the repeatability test was 0.22%. The detection limit of the liquid chromatography was 0.06 mg/L, and the quantification limit was 0.2 mg/L. In order to improve the yield and purity, the Camellia oleifera saponins were extracted from Camellia oleifera Abel. seed meal by methanol extraction. Then, the extracted Camellia oleifera saponins were extracted with an ammonium sulfate/propanol aqueous two-phase system. We optimized the purification process of formaldehyde extraction and aqueous two-phase extraction. Under the optimal purification process, the purity of Camellia oleifera saponins extracted by methanol was 36.15%, and the yield was 25.24%. The purity of Camellia oleifera saponins obtained by aqueous two-phase extraction was 83.72%. Thus, this study can provide a reference standard for rapid and efficient detection and analysis of Camellia oleifera saponins for industrial extraction and purification.
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Camellia , Saponinas , Camellia/química , Saponinas/química , Metanol/análisis , Semillas/química , Agua/análisisRESUMEN
Acetaminophen (AC) is one of the most common over-the-counter drugs, and its pollutant in groundwater has attracted more attention due to its serious risk to human health. Currently, the research on AC is mainly focused on its detection, but few are concerned about its removal. In this work, for the first time, nitrogen-doped Soulangeana sepals derived biochar/ß-cyclodextrin-Metal-organic frameworks (N-SC/ß-CD-MOFs) composite was proposed for the simultaneous efficient removal and detection of AC. N-SC/ß-CD-MOFs combined the properties of host-guest recognition of ß-CD-MOFs and porous structure, high porosity, and large surface area of N-SC. Their synergies endowed N-SC/ß-CD-MOFs with a high adsorption capacity toward AC, which was up to 66.43 mg/g. The adsorption type of AC on the surface of N-SC/ß-CD-MOFs conformed to the Langmuir adsorption model, and the study of the adsorption mechanism showed that AC adsorption on N-SC was mainly achieved through hydrogen bonding. In addition, the high conductivity, large specific surface area and abundant active sites of N-SC/ß-CD-MOFs were of great significance to the high-performance detection of AC. Accordingly, the sensor prepared with N-SC/ß-CD-MOFs presented a wide linear range (1.0-30.0 µM) and a low limit of detection of 0.3 nM (S/N = 3). These excellent performances demonstrate that N-SC/ß-CD-MOFs could act as an efficient dual-functional material for the detection and removal of AC.
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Estructuras Metalorgánicas , Nitrógeno , Humanos , Porosidad , Acetaminofén , Estructuras Metalorgánicas/química , AdsorciónRESUMEN
Pollution caused by both forestry wastes and heavy metals has increasingly drawn attention owing to environmental safety concerns. After essential oil is extracted from Cinnamomum camphoras (L.), the branches are used as forestry wastes to prepare a phosphorus-doped biochar-attapulgite/bismuth film electrode decorated with magnetic Fe3O4 nanoparticles (MBA-BiFE). The smartphone-operated wireless portable sensor is employed for the simultaneous ultratrace voltammetric detection of multiple heavy metal ions (Cd2+, Pb2+, and Hg2+). Cd2+, Pb2+, and Hg2+ exhibit excellent electrochemical responses in linear ranges of 0.1 nM-5 µM, 0.01 nM-7 µM, and 0.1 nM-3 µM with limits of detection equal to 0.036, 0.003, and 0.011 nM, respectively. The recoveries of MBA-BiFE for Cd2+, Pb2+, and Hg2+ are 93.6-109.9%, 86.0-107.5%, and 94.8-104.6%, respectively, and the RSD values for repeated measurements of Cd2+, Pb2+, and Hg2+ are 4.2%, 2.8%, and 3.3%, respectively. A machine learning model based on an artificial neural network algorithm is constructed to enable a smart determination of ultratrace hazardous multiple metal ions. The portable sensor based on the screen-printed integrated three-electrode sensor modified using MBA-BiFE demonstrates advantages and practicability in outdoor detection, compared with conventional sensors based on MBA-BiFE. This study provides a smartphone-operated wireless portable sensing technique for high-potential applications in environmetallomics or agrometallomics using forestry waste-derived biochar as substrate for electrode preparation. HIGHLIGHTS: ⢠Fe3O4 decorated phosphorus-doped biochar-attapulgite/bismuth film electrode. ⢠A smartphone-operated sensor for analysis of multiple heavy metal ions. ⢠An Artificial neural network model for smart analysis of Cd2+, Pb2+, and Hg2+.
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Although much progress has been made in developing botanical fungicides to combat fungal diseases in crops, there remains a great need to improve the efficiency and long-term safety of these fungicides. This study proposes a novel strategy for designing citral-thiourea derivatives that feature such desirable properties. The motivation of the work herein was to enhance the antifungal activity of citral against C. gloeosprioides by exploiting the synergistic effect that arises from combining citral and thiourea compounds, thereby producing citral-thiourea derivatives that exhibit good long-term safety. The results revealed that the generated compounds e1, e3, e6, e18, and g showed remarkable antifungal activities against C. gloeosprioides, with corresponding EC50 values reaching 0.16, 1.66, 1.37, 4.76, and 4.60 mg/L, respectively, showing that the compounds significantly outperformed both the positive control kresoxim-methyl and the commercially available fungicide carbendazim. Furthermore, compound g showed stronger protective efficacy against C. gloeosprioides than carbendazim on mango fruit at 25 mg/L. Investigating the preliminary structure-activity relationship (SAR) of the compounds also revealed that the citral-thiourea derivatives exhibited higher antifungal activities against C. gloeosprioides compared to citral and thiourea compounds. This reinforcement of antifungal activity observed in the derivatives was found to be attributable to the two characteristics of low molecular size and the presence of a fluorine atom in the meta-position of the benzene ring. Beyond this, it was determined from QSAR that two molecular descriptors (the Kier-Hall index (order 3) and Tot dipole of the molecules) were negatively related to the antifungal activity of the citral-thiourea derivatives, while one other (the maximum resonance energy of a C-H bond) was positively related to their antifungal activity. More importantly, the citral-thiourea derivatives with high antifungal activities (i.e., compounds e1, e3, e6, e14, e15, e18, and g) exhibited negligible cytotoxicity to LO2 and HEK293T cell lines. The antifungal mechanism of the generated citral-thiourea derivatives was investigated by scanning electron microscopy (SEM) and relative conductivity. The derivatives were found to affect mycelial morphology and increase fungal cell membrane permeability, thereby resulting in the destruction of fungal cell membranes. These promising results provide novel insights into the study and potential application value of citral-thiourea derivatives as high-efficiency antifungal agents against C. gloeosprioides.
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Cinnamomum camphora is a traditional aromatic plant used to produce linalool and borneol flavors in southern China; however, its leaves also contain many other unutilized essential oils. Herein, we report geographic relationships for the yield and compositional diversity of C. camphora essential oils. The essential oils of 974 individual trees from 35 populations in 13 provinces were extracted by hydrodistillation and analyzed qualitatively and quantitatively by gas chromatography-mass spectrometry and gas chromatography-flame ionization detection, respectively. Oil yields ranged from 0.01% to 3.46%, with a significantly positive correlation with latitude and a significantly negative correlation with longitude. In total, 41 compounds were identified, including 15 monoterpenoids, 24 sesquiterpenoids, and two phenylpropanoids. Essential oil compositions varied significantly among individuals and could be categorized into various chemotypes. The six main chemotypes were eucalyptol, nerolidol, camphor, linalool, selina, and mixed types. The other 17 individual plants were chemotypically rare and exhibited high levels of methyl isoeugenol, methyl eugenol, δ-selinene, or borneol. Eucalyptol-type plants had the highest average oil yield of 1.64%, followed in decreasing order by linalool-, camphor-, mixed-, selina-, and nerolidol-type plants. In addition, the five main compounds exhibited a clear geographic gradient. Eucalyptol and linalool showed a significantly positive correlation with latitude, while selina-6-en-4-ol was significantly and negatively correlated with latitude. trans-Nerolidol and selina-6-en-4-ol showed significantly positive correlations with longitude, whereas camphor was significantly and negatively correlated with longitude. Canonical correspondence analysis indicated that environmental factors could strong effect the oil yield and essential oil profile of C. camphora.
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Cinnamomum camphora , Cinnamomum , Aceites Volátiles , Humanos , Aceites Volátiles/química , Cinnamomum camphora/química , Eucaliptol/análisis , Alcanfor/química , Cromatografía de Gases y Espectrometría de Masas , Hojas de la Planta/químicaRESUMEN
BACKGROUND: Euryale ferox is an important cash crop and valuable tonic in traditional medicine. The seeds of E. ferox are rich in starch, which is hard to digest, and the digestion speed is significantly slower than that of rice starch. The goal of this study was to evaluate the effects of E. ferox seed-coat phenolics (EFCPs) on the digestion of E. ferox seed starch. RESULTS: EFCPs were extracted and identified by ultra-high performance liquid chromatography coupled with quadrupole time-of-flight mass spectrometry. We optimized the extraction parameters, and the final extraction yield was about 1.49%. We identified seven phenolics from the E. ferox seed-coat extracts: gallic acid, digalloylhexoside, catechin, procyanidin B2, epicatechin, ellagic acid, and epicatechin gallate. Quantitative analysis results showed that the E. ferox seed phenolics mainly distributed in the seed coat and the gallic acid, digalloylhexoside, and epicatechin gallate were three main phenolic compounds. The phenolics displayed strong inhibitory activities on α-glucosidase and α-amylase with an IC50 of 3.25 µg mL-1 and 1.36 mg mL-1 respectively. Furthermore, these phenolics could interact with starch by hydrogen bonds, which might make its starch more difficult to digest. CONCLUSION: Our investigation suggests that the EFCPs can strongly inhibit the digestion of E. ferox seed starch by inhibiting the α-amylase and α-glucosidase activities and interacting with starch by hydrogen bonds; therefore, E. ferox seeds have a promising application prospect in foods for hypoglycemia. © 2023 Society of Chemical Industry.
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Extractos Vegetales , Almidón , Almidón/análisis , Extractos Vegetales/química , alfa-Glucosidasas , Fenoles/análisis , Semillas/química , Ácido Gálico/análisis , alfa-Amilasas/análisis , DigestiónRESUMEN
We synthesized a series of quinazolinone derivates as tyrosinase inhibitors and evaluated their inhibition constants. We synthesized 2-(2,6-dimethylhepta-1,5-dien-1-yl)quinazolin-4(3H)-one (Q1) from the natural citral. The concentration, which led to 50% activity loss of Q1, was 103 ± 2 µM (IC50 = 103 ± 2 µM). Furthermore, we considered Q1 to be a mixed-type and reversible tyrosinase inhibitor, and determined the KI and KIS inhibition constants to be 117.07 µM and 423.63 µM, respectively. Our fluorescence experiment revealed that Q1 could interact with the substrates of tyrosine and L-DOPA in addition to tyrosinase. Molecular docking studies showed that the binding of Q1 to tyrosinase was driven by hydrogen bonding and hydrophobicity. Briefly, the current study confirmed a new tyrosinase inhibitor, which is expected to be developed into a novel pigmentation drug.
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Agaricales , Monofenol Monooxigenasa , Agaricales/metabolismo , Inhibidores Enzimáticos/química , Cinética , Simulación del Acoplamiento Molecular , Quinazolinonas/farmacología , Relación Estructura-ActividadRESUMEN
Control of fungal phytopathogens affecting crops and woodlands is an important goal in environmental management and the maintenance of food security. This work describes the synthesis of 37 camphor derivatives, of which 27 were new compounds. Their antifungal effects on six fungi were evaluated in vitro. Compounds 3a, 4a and 5k showed strong antifungal activity against Trametes versicolor, with EC50 values of 0.43, 6.80 and 4.86 mg/L, respectively, which were better than that of tricyclazole (EC50 118.20 mg/L) and close to or better than that of carbendazim (EC50 1.20 mg/L). The most potent compound, 3a, exhibited broad-spectrum antifungal activity towards six fungi with EC50 values within the range of 0.43-40.18 mg/L. Scanning electron microscopy demonstrated that compounds 3a, 4a and 5k gave irregular growth and shriveling of the mycelia. In vitro cytotoxicity evaluation revealed that the tested camphor derivatives had mild or no cytotoxicity for LO2 and HEK293T cell lines. Quantitative structure-activity relationship (QSAR) analysis revealed that the number of F atoms, relative molecular weight, the atomic orbital electronic population and total charge on the positively charged surfaces of the molecules of camphor derivatives have effects on antifungal activity. The present study may provide a theoretical basis for a high-value use of camphor and could be helpful for the development of novel potential antifungals.
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The simultaneous detection of multiple biological small molecules is critical for human health evaluation and disease prevention. In this study, a nano-ZnS decorated hierarchically porous carbon (ZSHPC) electrocatalyst with multiple enzyme-like activities as a nanozyme sensing platform for simultaneous derivative voltametric detection of four important biological small molecules, dopamine (DA), uric acid (UA), guanine (G), and adenine (A), is successfully synthesized via an in situ hydrothermal reaction using leaves of Cinnamomum camphora (L.) after the extraction of essential oil as a carbon source, ZnCl2 as both zinc source and an activator, sulfuric acid as a sulfur source, and silica gel as a hard template. Activator together with the introduction of silica gel is beneficial for tuning pore structure. The in situ synthesized ZnS nanoparticles and sulfur doping improve the conductivity and cycling stability of the material. The ZSHPC electrode with multiple enzyme-like activities and oxidase-like characteristics was employed for the simultaneous detection of multiple target molecules in linear ranges of 0.3-500 µM with detection limits of 0.12 µM for DA, 0.26 µM for UA, 0.07 µM for G, and 0.075 µM for A. A derivative technique was selected for enhancing the peak resolution of the partial overlapped voltammograms and eliminating human error. Both the coefficient of determination and residual prediction deviation were used to evaluate this technique.
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Dopamina , Ácido Úrico , Adenina , Ácido Ascórbico , Carbono , Técnicas Electroquímicas , Guanina , Humanos , PorosidadRESUMEN
To develop new antifungal agents against phytopathogenic fungi, a series of citral-thiazolyl hydrazine derivatives were designed, synthesized, and characterized by FT-IR, 1H NMR, 13C NMR, and HRMS. Antifungal activity results showed that most synthetic compounds exhibited broad-spectrum antifungal activities against six phytopathogenic fungi in vitro. Notably, compounds b and c15 exhibited remarkable antifungal activity against Colletotrichum gloeosprioides, Rhizoctonia solani, Phytophthora nicotianae var. nicotianae, Diplodia pinea, Colletotrichum acutatum, and Fusarium oxysporum f. sp. niveum, which were all superior to the positive control tricyclazole. Structure-activity relationship (SAR) studies demonstrated that introducing electron-withdrawing groups such as F on the benzene ring exhibited outstanding antifungal activities against all the tested fungi. Furthermore, compound b could effectively control rice sheath blight and showed higher curative activities against R. solani than validamycin·bacillus in vivo. In addition, the in vitro cytotoxicity results indicated that compound b possessed moderate cytotoxicity activity, and all citral-thiazolyl hydrazine derivatives exhibited lower or no cytotoxicity to the LO2 and HEK293 cell lines. In addition, the acute oral toxicity test showed that compound b had moderate toxicity (level II) with an LD50 value of 310 mg/kgâ¯bw (95% confidence limit: 175-550 mg/kgâ¯bw). Finally, a preliminary action mechanism study showed that causing obvious malformation of mycelium and increasing cell membrane permeability are two of the potential mechanisms by which compound b exerts antifungal activity. The present work indicates that some of these derivatives may serve as novel potential fungicides, and compound b is expected to be the leading structure for the development of new antifungal agents.
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Antifúngicos , Hongos , Monoterpenos Acíclicos , Antifúngicos/farmacología , Células HEK293 , Humanos , Hidrazinas/farmacología , Espectroscopía Infrarroja por Transformada de Fourier , Relación Estructura-ActividadRESUMEN
ß-pinene is a monoterpene isolated from turpentine oil and numerous other plants' essential oils, which has a broad spectrum of biological activities. In the current work, six novel ß-pinene quaternary ammonium (ß-PQA) salts were synthesized and evaluated in vitro for their antifungal, antibacterial and anticancer activities. The in vitro assay results revealed that compounds 4a and 4b presented remarkable antimicrobial activity against the tested fungi and bacteria. In particular, compound 4a showed excellent activities against F. oxysporum f.sp. niveum, P. nicotianae var.nicotianae, R. solani, D. pinea and Fusicoccumaesculi, with EC50 values of 4.50, 10.92, 9.45, 10.82 and 6.34 µg/mL, respectively. Moreover, compound 4a showed the best antibacterial action against E. coli, P. aeruginosa, S. aureus and B. subtilis, with MIC at 2.5, 0.625, 1.25 and 1.25 µg/mL, respectively. The anticancer activity results demonstrated that compounds 4a, 4b, 4c and 4f exhibited remarkable activity against HCT-116 and MCF-7 cell lines, with IC50 values ranged from 1.10 to 25.54 µM. Notably, the compound 4c displayed the strongest cytotoxicity against HCT-116 and MCF-7 cell lines, with the IC50 values of 1.10 and 2.46 µM, respectively. Furthermore, preliminary antimicrobial mechanistic studies revealed that compound 4a might cause mycelium abnormalities of microbial, cell membrane permeability changes and inhibition of the activity of ATP. Altogether, these findings open interesting perspectives to the application of ß-PQA salts as a novel leading structure for the development of effective antimicrobial and anticancer agents.
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Antibacterianos/farmacología , Antifúngicos/farmacología , Antineoplásicos/farmacología , Diseño de Fármacos , Neoplasias/tratamiento farmacológico , Compuestos de Amonio Cuaternario/farmacología , Antibacterianos/química , Antifúngicos/química , Antineoplásicos/química , Apoptosis , Proliferación Celular , Células HCT116 , Humanos , Células MCF-7 , Estructura Molecular , Neoplasias/patología , Compuestos de Amonio Cuaternario/química , Relación Estructura-ActividadRESUMEN
BACKGROUND: The development of new antifungal agents has always been a hot research topic in pesticide development. In this study, a series of derivatives of natural compound ß-pinene were prepared, and the antifungal activities of these derivatives were evaluated. The purpose of this work is to develop some novel molecules as promising new fungicides. METHODS: Through a variety of chemical reactions, ß-pinene was transformed into a series of ß-pinene-based derivatives containing amide moieties and acylthiourea moieties. The antifungal activities of these derivatives against five plant pathogens including Colletotrichum gloeosporioides, Fusarium proliferatum, Alternaria kikuchiana, Phomopsis sp. and Phytophthora capsici were tested; preliminary structure-activity relationship was discussed. RESULTS: Some derivatives exhibited moderate or significant antifungal activity due to the fusion of the amide moiety or the acylthiourea moiety with the pinane skeleton. The structure-activity relationship analysis showed that the fluorine atom and the strong electron withdrawing nitro group, or trifluoromethyl group on the benzene ring of the derivatives had a significant effect on the improvement of the antifungal activity against Colletotrichum gloeosporioides, Fusarium proliferatum, Alternaria kikuchiana and Phomopsis sp. Meanwhile, the introduction of an ethyl group at the meta-position on the benzene ring of the derivatives could improve the antifungal activity against Phytophthora capsici. Compounds 4e, 4h, 4q, 4r exhibited broad-spectrum antifungal activity against the tested strains. Compound 4o had significant antifungal activity against Phytophthora capsici (IC50 = 0.18 µmol/L). These derivatives were expected to be used as precursor molecules for novel pesticide development in further research.
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Alternaria/efectos de los fármacos , Monoterpenos Bicíclicos/síntesis química , Colletotrichum/efectos de los fármacos , Fungicidas Industriales/síntesis química , Fusarium/efectos de los fármacos , Phytophthora/efectos de los fármacos , Sordariales/efectos de los fármacos , Alternaria/crecimiento & desarrollo , Amidas/química , Monoterpenos Bicíclicos/farmacología , Colletotrichum/crecimiento & desarrollo , Fungicidas Industriales/farmacología , Fusarium/crecimiento & desarrollo , Pruebas de Sensibilidad Microbiana , Phytophthora/crecimiento & desarrollo , Enfermedades de las Plantas/microbiología , Enfermedades de las Plantas/terapia , Plantas/microbiología , Sordariales/crecimiento & desarrollo , Relación Estructura-Actividad , Tiourea/químicaRESUMEN
Using a mixture of neutral primary amine dehydroabietylamine (DHAA) and long-chain cetyltrimethyl ammonium bromide (CTAB) as the template, ordered lamellar supermicroporous silicas were synthesized with NaOH as the base source and tetraethylorthosilicate (TEOS) as the silica source. The concentrations of DHAA, CTAB, and NaOH in the synthesis system had great effects on the structural properties of the samples. When the molar ratio of components was nTEOS:nCTAB:nDHAA:nNaOH:nH2O = 1:0.114:0.00457:0.5:60, the material showed a lamellar phase with the highest ordering degree. By adding only a trace amount of DHAA into the synthesis system, the structure of the samples could be transformed from cubic phase to lamellar phase, since the added DHAA solubilized in CTAB micelles to change the effective surfactant ion pair packing parameter. The dosage of CTAB should be moderate; too high or too low will decay the ordering degree of the lamellar structure.A much higher concentration of NaOH resulted in an ethanol-rich solvent in which the DHAA did not solubilize in the micelles of CTAB, but adsorbed at the hydrophilic headgroup-solvent interface. Accordingly, a structural transformation from lamellar phase to hexagonal phase occurred.
Asunto(s)
Dióxido de Silicio/química , Dióxido de Silicio/síntesis química , Abietanos/química , Cationes , Cetrimonio/química , Nitrógeno/química , Porosidad , Hidróxido de Sodio/química , Temperatura , Difracción de Rayos XRESUMEN
By using dehydroabietyltrimethyl ammonium bromine (DTAB), a novel rosin-derived quaternary ammonium salt, as template and peroxotitanium acid as precursor, ordered lamellar supermicroporous titania has been synthesized via a hydrothermal process. The template agent:titanium source molar ratio in the synthesis system and the hydrothermal temperature have great impact on the microstructure characteristics of the samples. The increase of DTAB:TiO2 molar ratio from 0.04:1 to 0.10:1 is favorable to the increase of regularity of pore structures, but has no significant effects on the crystalline structures. The increase of the hydrothermal temperature from 343 to 393 K can induce an increase in crystallinity of the samples. However, the exorbitant hydrothermal temperature will reduce the regularity of pore structures. When the mole ratio of DTAB:TiO2 is 0.10:1 and the hydrothermal temperature is 373 K, the as-synthesized sample possesses pore structure with the highest level of long-range order, as well as pore wall with semicrystallized anatase phase. The pore size and the pore wall thickness are about 2.0 nm and 1.0 nm, respectively.