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1.
Bioorg Chem ; 151: 107708, 2024 Oct.
Artículo en Inglés | MEDLINE | ID: mdl-39133973

RESUMEN

Pesticides play an important role in the development of agriculture, as they can prevent and control crop diseases and pests, improve crop yield and quality. However, the abuse and improper use of pesticides can lead to negative impacts such as environmental pollution and pest resistance issues. There is an urgent need to develop green, safe, and efficient pesticides. In this work, natural product arecoline was selected as parent structure, a series of arecoline derivatives were designed, synthesized, and systematically investigated antiviral activities against tobacco mosaic virus (TMV). These compounds were found to have good to excellent anti-TMV activities for the first time. The antiviral activities of 4a, 4 h, 4 l, 4p, 6a, 6c, and 6f are higher than that of ningnanmycin. Compounds 4 h (EC50 value 146 µg/mL) and 4p (EC50 value 161 µg/mL) with simple structures and excellent activities emerged as new antiviral candidates. We chose 4 h to further investigate the antiviral mechanism, which revealed that it can cause virus fragmentation by acting on the viral coat protein (CP). We further validated this result through molecular docking. These compounds also displayed broad-spectrum fungicidal activities against 8 plant pathogenic fungi. This work lays the theoretical foundation for the application of arecoline derivatives in the agricultural field.


Asunto(s)
Antivirales , Arecolina , Diseño de Fármacos , Oxadiazoles , Virus del Mosaico del Tabaco , Virus del Mosaico del Tabaco/efectos de los fármacos , Antivirales/farmacología , Antivirales/química , Antivirales/síntesis química , Oxadiazoles/química , Oxadiazoles/farmacología , Oxadiazoles/síntesis química , Relación Estructura-Actividad , Estructura Molecular , Arecolina/farmacología , Arecolina/síntesis química , Arecolina/química , Relación Dosis-Respuesta a Droga , Pruebas de Sensibilidad Microbiana , Simulación del Acoplamiento Molecular
2.
Molecules ; 29(13)2024 Jul 02.
Artículo en Inglés | MEDLINE | ID: mdl-38999100

RESUMEN

Plant diseases caused by pathogenic fungi seriously affect the yield and quality of crops, cause huge economic losses, and pose a considerable threat to global food security. Phenylpyrrole analogues were designed and synthesized based on alkaloid lycogalic acid. All target compounds were characterized by 1H NMR, 13C NMR, and HRMS. Their antifungal activities against seven kinds of phytopathogenic fungi were evaluated. The results revealed that most compounds had broad-spectrum fungicidal activities at 50 µg/mL; 14 compounds displayed more than 60% fungicidal activities against Rhizoctonia cerealis and Sclerotinia sclerotiorum, and in particular, the fungicidal activities of compounds 8g and 8h against Rhizoctonia cerealis were more than 90%, which could be further developed as lead agents for water-soluble fungicides. The molecular docking results indicate that compounds 8g and 8h can interact with 14α-demethylase (RcCYP51) through hydrogen bonding with strong affinity.


Asunto(s)
Alcaloides , Antifúngicos , Diseño de Fármacos , Simulación del Acoplamiento Molecular , Pirroles , Rhizoctonia , Antifúngicos/farmacología , Antifúngicos/síntesis química , Antifúngicos/química , Pirroles/química , Pirroles/farmacología , Pirroles/síntesis química , Alcaloides/química , Alcaloides/farmacología , Alcaloides/síntesis química , Rhizoctonia/efectos de los fármacos , Relación Estructura-Actividad , Pruebas de Sensibilidad Microbiana , Estructura Molecular , Ascomicetos/efectos de los fármacos
3.
Bioorg Chem ; 135: 106508, 2023 06.
Artículo en Inglés | MEDLINE | ID: mdl-37023583

RESUMEN

Fungal and viral diseases account for 70-80% of agricultural production losses caused by microbial diseases. Synthetic fungicides and antiviral agents have been used to treat plant diseases caused by plant pathogenic fungi and viruses, but their use has been criticized due to their adverse side effects. As alternative strategies, natural fungicides and antiviral agents have attracted many researchers' interest in recent years. Herein, we designed and synthesized a series of novel polycarpine simplified analogues. Antiviral activity research against tobacco mosaic virus (TMV) revealed that most of the designed compounds have good antiviral activities. The virucidal activities of 4, 6d, 6f, 6h, and 8c are higher than that of polycarpine and similar to that of ningnanmycin. The structure simplified compound 8c was selected for further antiviral mechanism research which showed that compound 8c could inhibit the formation of 20S protein discs by acting on TMV coat protein. These compounds also displayed broad-spectrum fungicidal activities against 7 kinds of plant fungi. This work lays the foundation for the application of polycarpine simplified analogues in crop protection.


Asunto(s)
Fungicidas Industriales , Virus del Mosaico del Tabaco , Antivirales/química , Fungicidas Industriales/química , Relación Estructura-Actividad , Hongos , Diseño de Fármacos
4.
Molecules ; 28(5)2023 Feb 26.
Artículo en Inglés | MEDLINE | ID: mdl-36903426

RESUMEN

Plant virus diseases seriously affect the yield and quality of agricultural products, and their prevention and control are difficult. It is urgent to develop new and efficient antiviral agents. In this work, a series of flavone derivatives containing carboxamide fragments were designed, synthesized, and systematically evaluated for their antiviral activities against tobacco mosaic virus (TMV) on the basis of a structural-diversity-derivation strategy. All the target compounds were characterized by 1H-NMR, 13C-NMR, and HRMS techniques. Most of these derivatives displayed excellent in vivo antiviral activities against TMV, especially 4m (inactivation inhibitory effect, 58%; curative inhibitory effect, 57%; and protection inhibitory effect, 59%), which displayed similar activity to ningnanmycin (inactivation inhibitory effect, 61%; curative inhibitory effect, 57%; and protection inhibitory effect, 58%) at 500 µg mL-1; thus, it emerged as a new lead compound for antiviral research against TMV. Antiviral mechanism research by molecular docking demonstrated that compounds 4m, 5a, and 6b could interact with TMV CP and disturb virus assembly.


Asunto(s)
Flavonas , Virus del Mosaico del Tabaco , Antivirales/farmacología , Relación Estructura-Actividad , Simulación del Acoplamiento Molecular , Flavonas/farmacología , Diseño de Fármacos
5.
Molecules ; 28(10)2023 May 18.
Artículo en Inglés | MEDLINE | ID: mdl-37241910

RESUMEN

A series of novel chiral thiourea fluorescent probes HL1-HL6 were designed and synthesized from (1R,2R)-1,2-diphenylethylenediamine, phenyl isothiocyanate, and different substituted salicylic aldehydes. All of the compounds were confirmed by 1H NMR, 13C NMR, and HRMS. They exhibit high selectivity and sensitivity to Zn2+ in the presence of nitrate ions with the detection limit of 2.3 × 10-8 M (HL5). Meanwhile, their zinc (II) complexes (L-ZnNO3) showed continuous response to H2PO4- in acetonitrile solution. The identification processes could further be verified by supramolecular chemistry data analysis, X-ray single-crystal diffraction analysis, and theoretical study. The research provides reliable evidence for an explanation of the mechanism of action of thiourea involved in coordination, which is important for the application of thiourea fluorescent probes. In short, the sensors HL1-HL6 based on chiral thiourea Schiff base will be promising detection devices for Zn2+ and H2PO4-.

6.
Molecules ; 28(7)2023 Mar 29.
Artículo en Inglés | MEDLINE | ID: mdl-37049795

RESUMEN

Pesticides are essential for the development of agriculture. It is urgent to develop green, safe and efficient pesticides. Bisindole alkaloids have unique and concise structures and broad biological activities, which make them an important leading skeleton in the creation of new pesticides. In this work, we synthesized bisindole alkaloid barakacin in a simple seven-step process, and simultaneously designed and synthesized a series of its derivatives. Biological activity research indicated that most of these compounds displayed good antiviral activities against tobacco mosaic virus (TMV). Among them, compound 14b exerted a superior inhibitory effect in comparison to commercially available antiviral agent ribavirin, and could be expected to become a novel antiviral candidate. Molecular biology experiments and molecular docking research found that the potential target of compound 14b was TMV coat protein (CP). These compounds also showed broad-spectrum anti-fungal activities against seven kinds of plant fungi.


Asunto(s)
Alcaloides , Fungicidas Industriales , Virus del Mosaico del Tabaco , Antivirales/farmacología , Antivirales/química , Relación Estructura-Actividad , Simulación del Acoplamiento Molecular , Fungicidas Industriales/farmacología , Fungicidas Industriales/química , Ribavirina/farmacología , Alcaloides/química , Diseño de Fármacos
7.
Molecules ; 27(20)2022 Oct 13.
Artículo en Inglés | MEDLINE | ID: mdl-36296469

RESUMEN

A series of oxazinyl flavonoids were synthesized on the basis of flavone. The structures of all target compounds were characterized by 1H NMR, 13C NMR, and HRMS. The effect of the different substituent on the N-position of oxazinyl flavonoids against tobacco mosaic virus (TMV) activities and plant pathogen activities was systematically investigated. In vivo anti-TMV activity showed that most of the compounds showed moderate-to-excellent antiviral activities against TMV at 500 µg/mL. Compounds 6b, 6d, 6j-6k, and 6n-6q showed better antiviral activities than ribavirin (a commercially available antiviral agent) and apigenin. In particular, compounds 6n and 6p even displayed slightly higher activities than ningnanmycin, which were expected to become new antiviral candidates. Antiviral mechanism research by molecular docking exhibited that compounds 6n and 6p could interact with TMV CP and inhibit virus assembly. Then, the antifungal activities of these compounds against six kinds of plant pathogenic fungi were tested, and the results showed that these oxazinyl flavonoids had broad-spectrum fungicidal activities. Compounds 6h exhibited antifungal activity of up to 91% against Physalospora piricola and might become a candidate drug for new fungicides.


Asunto(s)
Alcaloides , Fungicidas Industriales , Virus del Mosaico del Tabaco , Antivirales/química , Ribavirina/farmacología , Fungicidas Industriales/farmacología , Antifúngicos/farmacología , Relación Estructura-Actividad , Flavonoides/farmacología , Simulación del Acoplamiento Molecular , Apigenina/farmacología , Estructura Molecular , Alcaloides/química , Hongos , Diseño de Fármacos
8.
Molecules ; 27(23)2022 Dec 03.
Artículo en Inglés | MEDLINE | ID: mdl-36500597

RESUMEN

Three novel Ir(III) complexes, (ppy)2Ir(L-alanine) (Ir1) (ppy = 2-phenylpyridine), (F4ppy)2Ir(L-alanine) (Ir2) (F4ppy = 2-(4-fluorophenyl)pyridine), and (F2,4,5ppy)2Ir(L-alanine) (Ir3) (F2,4,5ppy = 2-(2,4,5-trifluorophenyl)pyridine), based on simple L-alanine as ancillary ligands were synthesized and investigated. Due to the introduction of fluorine substituents on the cyclometalated ligands, complexes Ir1-Ir3 exhibited yellow to sky-blue emissions (λem = 464-509 nm) in acetonitrile solution. The photoluminescence quantum yields (PLQYs) of Ir1-Ir3 ranged from 0.48-0.69, of which Ir3 with sky-blue luminescence had the highest PLQY of 0.69. The electrochemical study and density functional theory (DFT) calculations show that the highest occupied molecular orbital (HOMOs) energy of Ir1-Ir3 are stabilized by the introduction of fluorine substituents on the cyclometalated ligands, while L-alanine ancillary ligand has little contribution to HOMOs and lowest unoccupied molecular orbitals (LUMOs). Moreover, Ir1-Ir3 presented an excellent response to Cu2+ with a high selectivity, strong anti-interference ability, and short response time. Such a detection was based on significant phosphorescence quenching of their emissions, showing the potential application in chemosensors for Cu2+.


Asunto(s)
Iridio , Compuestos Organometálicos , Iridio/química , Ligandos , Compuestos Organometálicos/química , Luminiscencia , Iones , Flúor , Alanina
9.
Molecules ; 26(2)2021 Jan 13.
Artículo en Inglés | MEDLINE | ID: mdl-33450940

RESUMEN

Based on the structure of the natural product cysteine, a series of thiazolidine-4-carboxylic acids were designed and synthesized. All target compounds bearing thiazolidine-4-carboxylic acid were characterized by 1H-NMR, 13C-NMR, and HRMS techniques. The antiviral and antifungal activities of cysteine and its derivatives were evaluated in vitro and in vivo. The results of anti-TMV activity revealed that all compounds exhibited moderate to excellent activities against tobacco mosaic virus (TMV) at the concentration of 500 µg/mL. The compounds cysteine (1), 3-4, 7, 10, 13, 20, 23, and 24 displayed higher anti-TMV activities than the commercial plant virucide ribavirin (inhibitory rate: 40, 40, and 38% at 500 µg/mL for inactivation, curative, and protection activity in vivo, respectively), especially compound 3 (inhibitory rate: 51%, 47%, and 49% at 500 µg/mL for inactivation, curative, and protection activity in vivo, respectively) with excellent antiviral activity emerged as a new antiviral candidate. Antiviral mechanism research by TEM exhibited that compound 3 could inhibit virus assembly by aggregated the 20S protein disk. Molecular docking results revealed that compound 3 with higher antiviral activities than that of compound 24 did show stronger interaction with TMV CP. Further fungicidal activity tests against 14 kinds of phytopathogenic fungi revealed that these cysteine derivatives displayed broad-spectrum fungicidal activities. Compound 16 exhibited higher antifungal activities against Cercospora arachidicola Hori and Alternaria solani than commercial fungicides carbendazim and chlorothalonil, which emerged as a new candidate for fungicidal research.


Asunto(s)
Alternaria/efectos de los fármacos , Antifúngicos/farmacología , Antivirales/farmacología , Ascomicetos/efectos de los fármacos , Cisteína/farmacología , Virus del Mosaico del Tabaco/efectos de los fármacos , Antifúngicos/síntesis química , Antifúngicos/química , Antivirales/síntesis química , Antivirales/química , Cisteína/síntesis química , Cisteína/química , Descubrimiento de Drogas , Pruebas de Sensibilidad Microbiana , Estructura Molecular
10.
Mar Drugs ; 16(9)2018 Sep 03.
Artículo en Inglés | MEDLINE | ID: mdl-30177624

RESUMEN

Naamines, naamidines and various derivatives of these marine natural products were synthesized and characterized by means of nuclear magnetic resonance (NMR) spectroscopy and mass spectrometry. The activities of these alkaloids against a plant virus and phytopathogenic fungi were evaluated for the first time. A benzyloxy naamine derivative 15d displayed excellent in vivo activity against tobacco mosaic virus at 500 µg/mL (inactivation activity, 46%; curative activity, 49%; and protective activity, 41%); its activities were higher than the corresponding activities of the commercial plant virucide ribavirin (32%, 35%, and 34%, respectively), making it a promising new lead compound for antiviral research. In vitro assays revealed that the test compounds exhibited very good antifungal activity against 14 kinds of phytopathogenic fungi. Again, the benzyloxy naamine derivative 15d exhibited broad-spectrum fungicidal activity, emerging as a new lead compound for fungicidal research. Additional in vivo assays indicated that many of the compounds displayed inhibitory effects >30%.


Asunto(s)
Alcaloides/farmacología , Organismos Acuáticos/química , Hongos/efectos de los fármacos , Imidazoles/farmacología , Enfermedades de las Plantas/prevención & control , Virus del Mosaico del Tabaco/efectos de los fármacos , Alcaloides/síntesis química , Diseño de Fármacos , Hongos/patogenicidad , Fungicidas Industriales/síntesis química , Fungicidas Industriales/farmacología , Imidazoles/síntesis química , Estructura Molecular , Enfermedades de las Plantas/microbiología , Relación Estructura-Actividad , Virus del Mosaico del Tabaco/patogenicidad
11.
Water Sci Technol ; 75(7-8): 1548-1554, 2017 Apr.
Artículo en Inglés | MEDLINE | ID: mdl-28402295

RESUMEN

It is essential to control silica levels in sodium chromate solution during the process of electrolytic synthesis of sodium dichromate. On the basis of previous work, the desilication conditions were systematically studied and pH was found to have the most serious impact on the desilication process. The desilication rate under optimal conditions obtained from the orthogonal experiment results was up to 99.3%. Kinetic experiments showed that the desilication reaction was first-order in SiO2 concentration and the apparent activation energy was calculated to be 22 kJ mol-1, which is far less than the reported values. The morphology and structure of the desilication reaction product (DSP) were studied by scanning electron microscope (SEM) and X-ray diffraction (XRD). SEM showed that DSP had a loose etched structure. The pattern of XRD illustrated the crystallinity of DSP increased along the duration of the experiment. The phase of DSP was mainly Na6(AlSiO4)6. Based on the experimental data, the desilication mechanism has been discussed. The hexameric aluminosilicate ions were produced by the reaction of monomeric aluminosilicate ion, through hydrogen bond interaction, which was formed by SiO2(OH)22- and Al(OH)4-.


Asunto(s)
Compuestos de Aluminio/química , Cromatos/química , Dióxido de Silicio/química , Compuestos de Sodio/química , Concentración de Iones de Hidrógeno , Cinética , Soluciones , Difracción de Rayos X
12.
J Fungi (Basel) ; 10(2)2024 Feb 19.
Artículo en Inglés | MEDLINE | ID: mdl-38392832

RESUMEN

Plant diseases caused by pathogenic fungi or oomycetes seriously affect crop growth and the quality and yield of products. A series of novel 1,2,4-triazole derivatives containing carboxamide fragments based on amide fragments widely used in fungicides and the commercialized mefentrifluconazole were designed and synthesized. Their antifungal activities were evaluated against seven kinds of phytopathogenic fungi/oomycete. Results showed that most compounds had similar or better antifungal activities compared to mefentrifluconazole's inhibitory activity against Physalospora piricola, especially compound 6h (92%), which possessed outstanding activity. Compound 6h (EC50 = 13.095 µg/mL) showed a better effect than that of mefentrifluconazole (EC50 = 39.516 µg/mL). Compound 5j (90%) displayed outstanding anti-oomycete activity against Phytophthora capsici, with an EC50 value of 17.362 µg/mL, far superior to that of mefentrifluconazole (EC50 = 75.433 µg/mL). The result of molecular docking showed that compounds 5j and 6h possessed a stronger affinity for 14α-demethylase (CYP51). This study provides a new approach to expanding the fungicidal spectrum of 1,2,4-triazole derivatives.

13.
Pest Manag Sci ; 2024 Sep 23.
Artículo en Inglés | MEDLINE | ID: mdl-39311339

RESUMEN

BACKGROUND: The invasion of viruses and fungi can cause pathological changes in the normal growth of plants and is an important factor in causing plant infectious diseases. These pathogenic microorganisms can also secrete toxic metabolites, affecting crop quality and posing a threat to human health. In this work, we selected the natural product rutaecarpine as the lead compound to achieve the total synthesis and structural derivation. The antiphytoviral activities of these compounds were systematically studied using tobacco mosaic virus (TMV) as the tested strain, and the structure-activity relationships were summarized. RESULT: The anti TMV activities of compounds 5a, 5n, 6b, and 7c are significantly higher than that of commercial antiviral agent ningnanmycin. We chose 5n for further antiviral mechanism research, and the results showed that it can directly act on viral particles. The molecular docking results further confirmed the interaction of compound 5n and coat protein (CP). These compounds also exhibited broad-spectrum fungicidal activities against eight plant pathogens. Especially compounds 5j and 5p have significant anti-fungal activities (EC50: 5j, 1.76 µg mL-1; 5p, 1.59 µg mL-1) and can be further studied as leads for plant-based anti-fungal agents. CONCLUSION: The natural product rutaecarpine and its derivatives were synthesized, and evaluated for their anti-TMV and fungicidal activities. Compounds 5n and 5p with good activities emerged as new antiviral and anti-fungal candidates, respectively. This study provides important information for the research and development of the novel antiviral and fungicidal agents based on rutaecarpine derivatives. © 2024 Society of Chemical Industry.

14.
J Agric Food Chem ; 71(29): 10989-11000, 2023 Jul 26.
Artículo en Inglés | MEDLINE | ID: mdl-37433073

RESUMEN

Severe plant virus diseases lead to poor harvests and poor crop quality, and the lack of effective suppressive drugs makes plant disease control a huge challenge. Natural product-based structural simplification is an important strategy for finding novel pesticide candidates. According to our previous research on the antiviral activities of harmine and tetrahydroharmine derivatives, a series of chiral diamine compounds were designed and synthesized by means of structural simplification using diamines in natural products as the core structure in this work, and the antiviral and fungicidal activities were investigated. Most of these compounds displayed higher antiviral activities than those of ribavirin. Compounds 1a and 4g displayed higher antiviral activities than ningnanmycin at 500 µg/mL. The antiviral mechanism research revealed that compounds 1a and 4g could inhibit virus assembly by binding to tobacco mosaic virus (TMV) CP and interfere with the assembly process of TMV CP and RNA via transmission electron microscopy and molecular docking. Further fungicidal activity tests showed that these compounds displayed broad-spectrum fungicidal activities. Compounds 3a, 3i, 5c, and 5d with excellent fungicidal activities against Fusarium oxysporum f.sp. cucumerinum can be considered as new fungicidal candidates for further research. The current work provides a reference to the development of agricultural active ingredients in crop protection.


Asunto(s)
Productos Biológicos , Fungicidas Industriales , Virus del Mosaico del Tabaco , Antivirales/farmacología , Antivirales/química , Relación Estructura-Actividad , Diaminas/farmacología , Simulación del Acoplamiento Molecular , Fungicidas Industriales/farmacología , Fungicidas Industriales/química , Productos Biológicos/química , Diseño de Fármacos
15.
J Agric Food Chem ; 71(40): 14483-14492, 2023 Oct 11.
Artículo en Inglés | MEDLINE | ID: mdl-37751549

RESUMEN

Plant pathogenic fungi and viruses are seriously threatening agricultural production. There is an urgent need to develop novel fungicides and antiviral agents with low toxicity and high efficiency. In this study, we designed and synthesized 32 thiazole-, hydrazone-, and amide-containing derivatives of laurene and systematically evaluated their antiviral activities and fungicidal activities. Structure-simplified compounds 5a-5c, 5i, 5k, 5l, 11a, 11j, and 12c displayed higher antiviral activities than that of ningnanmycin. Compound 11a with a simple chemical structure, convenient synthetic route, and excellent antiviral activity emerged as a secondary lead compound. The docking results show that compounds 5i, 5k, and 11a have strong interactions with the tobacco mosaic virus coat protein (TMV CP). These compounds also exhibited significant fungicidal activities. Compounds 5g, 5k, 11j, and 11l displayed 9.15-17.45 µg/mL EC50 values against Pyricularia grisea, and compounds 5h (EC50: 8.01 µg/mL) and 11i (EC50: 15.23 µg/mL) exhibited a similar level of EC50 values with chlorothalonil (EC50: 7.33 µg/mL) against Physalospora piricola. Preliminary fungicidal mechanism research indicated that compound 5h has a certain destructive effect on the hyphae of P. piricola. This work lays a foundation for the application of laurene derivatives in plant protection.

16.
J Org Chem ; 77(14): 6208-14, 2012 Jul 20.
Artículo en Inglés | MEDLINE | ID: mdl-22720976

RESUMEN

A primary amine-thiourea organocatalyzed intramolecular Michael addition access was developed for the synthesis of trans-dihydrobenzofurans. Under the catalysis of an (R,R)-1,2-diphenylethylamine derived primary amine-thiourea bearing a glucosyl scaffold, the corresponding trans-dihydrobenzofurans were obtained in high yields with excellent level of enantioselectivities (94 to >99% ee). Moreover, an in situ isomerization occurring at high temperature gave good to excellent trans/cis ratios as well (trans/cis: 84/16-96/4).


Asunto(s)
Aminas/química , Benzofuranos/síntesis química , Tiourea/química , Benzofuranos/química , Estructura Molecular , Estereoisomerismo
17.
J Fungi (Basel) ; 9(1)2022 Dec 23.
Artículo en Inglés | MEDLINE | ID: mdl-36675845

RESUMEN

The interactions between plants and microorganisms, which are widely present in the microbial-dominated rhizosphere, have been studied. This association is highly beneficial to the organisms involved, as plants benefit soil microorganisms by providing them with metabolites, while microorganisms promote plant growth and development by promoting nutrient uptake and/or protecting the plant from biotic and abiotic stresses. Piriformospora indica, an endophytic fungus of Sebacinales, colonizes the roots of a wide range of host plants and establishes various benefits for the plants. In this work, an interaction between barley and the P. indica was established to elucidate microRNA (miRNA)-based regulatory changes in miRNA profiles and gene expression that occurred during the symbiosis. Growth promotion and vigorous root development were confirmed in barley colonized by P. indica. The genome-wide expression profile analysis of miRNAs in barley root showed that 7,798,928, 6,418,039 and 7,136,192 clean reads were obtained from the libraries of mock, 3 dai and 7 dai roots, respectively. Sequencing of the barley genome yielded in 81 novel miRNA and 450 differently expressed genes (DEGs). Additionally, 11, 24, 6 differentially expressed microRNAs (DEMs) in barley were found in the three comparison groups, including 3 dai vs. mock, 7 dai vs. mock and 7 dai vs. 3 dai, respectively. The predicted target genes of these miRNAs are mainly involved in transcription, cell division, auxin signal perception and transduction, photosynthesis and hormone stimulus. Transcriptome analysis of P. indica identified 667 and 594 differentially expressed genes (DEG) at 3 dai and 7 dai. Annotation and GO (Gene Ontology) analysis indicated that the DEGs with the greatest changes were concentrated in oxidoreductase activity, ion transmembrane transporter activity. It implies that reprogramming of fundamental miRNA and gene expression occurs both in barley and P. indica. Analysis of global changes in miRNA profiles of barley colonized with P. indica revealed that several putative endogenous barley miRNAs expressed upon colonization belonging to known micro RNA families involved in growth and developmental regulation.

18.
J Agric Food Chem ; 70(8): 2554-2563, 2022 Mar 02.
Artículo en Inglés | MEDLINE | ID: mdl-35179026

RESUMEN

In response to the invasion of plant viruses and pathogenic fungi, higher plants produce defensive allelochemicals. Finding candidate varieties of botanical pesticides based on allelochemicals is one of the important ways to create efficient and green pesticides. Here, a series of camalexin derivatives based on a phytoalexin camalexin scaffold were designed, synthesized, and assessed for their antiviral and fungicidal activities systematically. Most of these camalexin derivatives exhibited better antiviral activities against tobacco mosaic virus (TMV) than the control antiviral agent ribavirin. Under the same test conditions, the anti-TMV activities of compounds 3d, 5a, 5d, and 10f-10h were found to be equivalent to or better than that of ningnanmycin, an agricultural cytosine nucleoside antibiotic with excellent protective effect. The antiviral mechanism research showed that compound 5a could cause 20S CP disk fusion and disintegration, thus affecting the assembly of virus particles. The results of molecular docking indicate that there were obvious hydrogen bonds between compounds 3d, 5a, and 10f and TMV CP. The binding constants of compounds 5a and 10f to TMV CP were also calculated using fluorescence titration. These camalexin derivatives also presented broad spectrum fungicidal activities, especially for Rhizoctonia solani and Physalospora piricola. In this work, the design, synthesis, structure optimization, and mode of action of camalexin derivatives were carried out progressively. This work provides a reference for using defensive chemical compounds as novel pesticide lead compounds.


Asunto(s)
Antivirales , Virus del Mosaico del Tabaco , Antivirales/química , Diseño de Fármacos , Hongos , Indoles , Simulación del Acoplamiento Molecular , Sesquiterpenos , Relación Estructura-Actividad , Tiazoles , Fitoalexinas
19.
J Agric Food Chem ; 70(50): 15693-15702, 2022 Dec 21.
Artículo en Inglés | MEDLINE | ID: mdl-36479881

RESUMEN

Plant diseases seriously affect the growth of crops and the quality and yield of agricultural products. The search for plant-derived pesticide candidates based on natural products is a hot topic of current research. Marine natural products almazoles C-D were efficiently prepared and selected as the lead compounds in this work. Two series of almazole derivatives were designed and synthesized, and their antiviral and fungicidal activities were systematically evaluated. The results of anti-tobacco mosaic virus (anti-TMV) activity showed that almazoles C-D and their derivatives had good anti-TMV activities. Compounds 6, 15, 16a, 16b, 16g, 16l, 16n, 20a, 20d, 20i, and 20n exhibited better anti-TMV activities than the commercial antiviral agent ribavirin. Anti-TMV mechanism studies showed that compound 16b could induce the polymerization of 20S CP (coat protein, CP), thereby affecting the assembly of TMV virus particles. Molecular docking results showed that compounds 15, 16b, and 20n could combine with amino acid residues through hydrogen bonds to achieve an excellent anti-TMV effect. In addition, most of the almazole derivatives were found to have broad-spectrum fungicidal activities against eight kinds of plant pathogens (Fusarium oxysporum f. sp. cucumeris, Cercospora arachidicola Hori, Physalospora piricola, Rhizoctonia cerealis, Alternaria solani, Pyricularia grisea, Phytophthora capsici, and Sclerotinia sclerotiorum). This study provides an important evidence for the research and development of almazole alkaloids containing indole and oxazole structural groups as novel agrochemicals.


Asunto(s)
Productos Biológicos , Virus del Mosaico del Tabaco , Antivirales/farmacología , Antivirales/química , Relación Estructura-Actividad , Productos Biológicos/farmacología , Productos Biológicos/química , Simulación del Acoplamiento Molecular , Ribavirina/farmacología , Diseño de Fármacos
20.
J Agric Food Chem ; 70(20): 6006-6014, 2022 May 25.
Artículo en Inglés | MEDLINE | ID: mdl-35536647

RESUMEN

The unreasonable use or long-term use of a single variety of pesticide has led to drug resistance and made the pesticides ineffective. Therefore, the creation of new, efficient, and low-risk pesticides is imminent. Marine natural products play a vital role in serving as new lead compounds. In this work, we realized the efficient preparation of nine marine sesquiterpenes with the Stork-Danheiser reaction as the key step and designed and synthesized a series of their derivatives. The antiviral activity and antifungal activity research showed that these compounds exhibited good to excellent biological activities. Compounds 7b and 8e displayed significantly higher antiviral activities against tobacco mosaic virus (TMV) than ribavirin and could be used as new antiviral candidates. The antiviral mode of action research indicated that compound 8e inhibited the formation of the 20S protein disk by acting on the TMV coat protein and therefore inhibited the assembly of TMV particles. This work provides a new idea for the development of new pesticides based on marine sesquiterpenes.


Asunto(s)
Plaguicidas , Sesquiterpenos , Virus del Mosaico del Tabaco , Antivirales/farmacología , Diseño de Fármacos , Hongos , Plaguicidas/farmacología , Sesquiterpenos/farmacología , Relación Estructura-Actividad
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