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1.
Langmuir ; 40(1): 647-656, 2024 Jan 09.
Artigo em Inglês | MEDLINE | ID: mdl-38153972

RESUMO

Natural small molecules have demonstrated tremendous potential for the construction of supramolecular chiral nanostructures owing to their unique molecular structures and chirality. In this study, novel CO2-responsive supramolecular hydrogels were constructed using a series of rosin-based surfactants (CnMPAN, n = 10, 12, and 14). The macroscopic properties, rheological properties, nanostructures, and intermolecular interactions of the hydrogels were investigated using differential scanning calorimetry, rotational rheometry, cryogenic transmission electron microscopy, and Fourier transform infrared spectroscopy. Interestingly, diverse nanostructures containing helical nanofibers, interwoven nanofibers, and twisted nanoribbons were formed in the hydrogels, which were rarely observed in reported supramolecular hydrogels, and the strength of the hydrogels was significantly enhanced by increasing the CnMPAN concentration and the alkyl chain length. The obtained hydrogels exhibited excellent CO2-responsiveness, with no obvious variation in the nanostructures and rheological properties after response to CO2/N2 for five cycles. Taking advantage of the chiral nanostructures of hydrogels, gold nanoparticles (GNPs) were further prepared. The average particle sizes of the resulting GNPs were as low as 2.5 nm, and the GNPs also had a chiral structure. It is worth noting that no additional reductants and UV-light irradiation were used during the reduction process of GNPs. This study emphasizes that the unique molecular structure and chirality of rosin are critical for the preparation of hydrogels with chiral nanostructures. In addition, this study enriches the applications of forest resources.

2.
Langmuir ; 40(21): 10992-11010, 2024 May 28.
Artigo em Inglês | MEDLINE | ID: mdl-38743441

RESUMO

The exploration of environmentally friendly, less toxic, sustained-release insecticide is increasing with the growing demand for food to meet the requirements of the expanding population. As a sustained-release carrier, the unique, environmentally friendly intelligent responsive hydrogel system is an important factor in improving the efficiency of insecticide utilization and accurate release. In this study, we developed a facile approach for incorporating the natural compound rosin (dehydroabietic acid, DA) and zinc ions (Zn2+) into a poly(N-isopropylacrylamide) (PNIPAM) hydrogel network to construct a controlled-release hydrogel carrier (DA-PNIPAM-Zn2+). Then, the model insecticide avermectin (AVM) was encapsulated in the carrier at a drug loading rate of 36.32% to form AVM@DA-PNIPAM-Zn2+. Surprisingly, the smart controlled carrier exhibited environmental responsiveness, strongly enhanced mechanical properties, self-healing ability, hydrophobicity, and photostability to ensure a balance between environmental friendliness and the precision of the drug release. The release experiments showed that the carboxyl and amide groups in the polymer chains alter the intermolecular forces within the hydrogel meshes and ingredient diffusion by changing temperatures (25 and 40 °C) and pH values (5.8, 7.4, and 8.5), leading to different release behaviors. The insecticidal activity of the AVM@DA-PNIPAM-Zn2+ against oriental armyworms was good, with an effective minimum toxicity toward aquatic animals. Therefore, AVM@DA-PNIPAM-Zn2+ is an effective drug delivery system against oriental armyworms. We anticipate that this ecofriendly, sustainable, smart-response carrier may broaden the utilization rosin and its possible applications in the agricultural sector.


Assuntos
Portadores de Fármacos , Hidrogéis , Inseticidas , Ivermectina , Resinas Vegetais , Ivermectina/análogos & derivados , Ivermectina/química , Ivermectina/farmacologia , Ivermectina/toxicidade , Hidrogéis/química , Hidrogéis/farmacologia , Animais , Concentração de Íons de Hidrogênio , Inseticidas/química , Inseticidas/farmacologia , Resinas Vegetais/química , Portadores de Fármacos/química , Temperatura , Preparações de Ação Retardada/química , Preparações de Ação Retardada/farmacologia , Liberação Controlada de Fármacos , Mariposas/efeitos dos fármacos , Rosaceae/química , Zinco/química , Zinco/farmacologia , Resinas Acrílicas
3.
J Fluoresc ; 2024 Apr 23.
Artigo em Inglês | MEDLINE | ID: mdl-38652360

RESUMO

In this paper, molecules with AIE red light properties were designed by coupling dehydroabietic acid diarylamine and 2,3-diphenylfumaronitrile, which were designated 2DTPA-CN and 2TPA-CN. The emission wavelengths were 683 nm and 701 nm, respectively. The 2DTPA-CN and 2TPA-CN showed typical AIE characteristics with large Stokes shifts of 7.4 × 104 cm-1 and 6.7 × 104 cm-1, respectively. The obvious solvatochromism and electron cloud distributions of HOMO/LUMO in the ground and excited states both reveal the intramolecular charge transfer (ICT) effect. The 2DTPA-CN, boasting exceptional biocompatibility, was successfully prepared into nanoparticles (NPs), which were applied to tumor cell imaging, showing good bioimaging effects both in vitro imaging in live cells and in vivo imaging in live mice. The results demonstrated that it possesses significant potential as an effective bioimaging reagent for the detection of tumor cells. Furthermore, the incorporation of 2,3-diphenylfumaronitrile moieties to dehydroabietic acid diarylamine emerged as a proficient approach to broaden the emission wavelengths of rosin-based fluorescent materials.

4.
Environ Res ; 251(Pt 2): 118651, 2024 Jun 15.
Artigo em Inglês | MEDLINE | ID: mdl-38479718

RESUMO

To rapidly remove dyes from wastewater, iron-based metal-organic frameworks modified with phenolated lignin (NH2-MIL@L) were prepared by a one-step hydrothermal method. Analyses of the chemical structure and adsorption mechanism of the NH2-MIL@L proved the successful introduction of lignin and the enhancement of its adsorption sites. Compared with NH2-MIL-101-Fe without phenolated lignin, the modification with lignin increased the methyl orange (MO) adsorption rate of NH2-MIL@L. For the best adsorbent, NH2-MIL@L4, the MO adsorption efficiency in MO solution reached 95.09% within 5 min. NH2-MIL@L4 reached adsorption equilibrium within 90 min, exhibiting an MO adsorption capacity of 195.31 mg/g. The process followed pseudo-second-order kinetics and the Dubinin-Radushkevich model. MO adsorption efficiency of NH2-MIL@L4 was maintained at 89.87% after six adsorption-desorption cycles. In mixed solutions of MO and methylene blue (MB), NH2-MIL@L4 achieved an MO adsorption of 94.02% at 5 min and reached MO adsorption equilibrium within 15 min with an MO adsorption capacity of 438.6 mg/g, while the MB adsorption equilibrium was established at 90 min with an MB adsorption rate and capacity of 95.60% and 481.34 mg/g, respectively. NH2-MIL@L4 sustained its excellent adsorption efficiency after six adsorption-desorption cycles (91.2% for MO and 93.4% for MB). The process of MO adsorption by NH2-MIL@L4 followed the Temkin model and pseudo-second-order kinetics, while MB adsorption followed the Dubinin-Radushkevich model and pseudo-second-order kinetics. Electrostatic interactions, π-π interactions, hydrogen bonding, and synergistic interactions affected the MO adsorption process of NH2-MIL@L4.


Assuntos
Compostos Azo , Lignina , Poluentes Químicos da Água , Adsorção , Lignina/química , Compostos Azo/química , Poluentes Químicos da Água/química , Poluentes Químicos da Água/análise , Estruturas Metalorgânicas/química , Cinética , Ferro/química , Corantes/química
5.
Biomacromolecules ; 23(7): 2856-2866, 2022 07 11.
Artigo em Inglês | MEDLINE | ID: mdl-35694860

RESUMO

Low-k dielectrics are urgently needed in modern integrated circuits. The introduction of free volume instead of porous structures has become a powerful strategy to reduce the k value. According to this strategy, the biomass resource rosin-containing hydrogenated phenanthrene ring was introduced into benzocyclobutene (BCB) resin to reduce the k value; then a rosin-based BCB monomer was successfully synthesized. Meanwhile, the BCB monomer without a rosin skeleton was prepared. After converting the monomers into thermo-crosslinked materials, notably that the rosin skeleton has a great influence on the free volume and k value of the material. The fractional free volume and k value of the former are 26% and 2.44, respectively, and those of the latter are 14% and 2.84, respectively. In addition, the distances between molecular chains and the density of the former are 0.60 nm and 1.06 g cm-3, respectively; those of the latter are 0.56 nm and 1.28 g cm-3, respectively. These data show that introducing hydrogenated phenanthrene rings occupies part of the space and hinders the packing of molecular chains, which increases the distance between molecular chains and reduces the density of the polymer, resulting in an increasing free volume and a reducing k value. Notably that introducing hydrogenated phenanthrene rings cannot affect other properties of the material. Therefore, this research indicates that introducing rosin skeletons can prepare high-performance materials, which provide some promising low-k materials for the development of electronics and microelectronics.


Assuntos
Fenantrenos , Resinas Vegetais , Fenantrenos/química , Polímeros , Resinas Vegetais/química
6.
Molecules ; 24(17)2019 Aug 29.
Artigo em Inglês | MEDLINE | ID: mdl-31470567

RESUMO

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.


Assuntos
Alternaria/efeitos dos fármacos , Monoterpenos Bicíclicos/síntese química , Colletotrichum/efeitos dos fármacos , Fungicidas Industriais/síntese química , Fusarium/efeitos dos fármacos , Phytophthora/efeitos dos fármacos , Sordariales/efeitos dos fármacos , Alternaria/crescimento & desenvolvimento , Amidas/química , Monoterpenos Bicíclicos/farmacologia , Colletotrichum/crescimento & desenvolvimento , Fungicidas Industriais/farmacologia , Fusarium/crescimento & desenvolvimento , Testes de Sensibilidade Microbiana , Phytophthora/crescimento & desenvolvimento , Doenças das Plantas/microbiologia , Doenças das Plantas/terapia , Plantas/microbiologia , Sordariales/crescimento & desenvolvimento , Relação Estrutura-Atividade , Tioureia/química
7.
Chemistry ; 24(36): 9033-9040, 2018 Jun 26.
Artigo em Inglês | MEDLINE | ID: mdl-29672958

RESUMO

The phase behavior and aggregates of a catanionic system have been investigated. The anionic surfactants in the mixed systems were sodium N-alkylmaleimidepimaric carboxylate (Cn -MPA-Na, n=12, 14, 16), which were prepared from rosin and contain a large rigid skeleton and a flexible alkane chain, and the cationic surfactant was cetyltrimethylammonium bromide (CTAB). The phase behavior of the C14 -MPA-Na/CTAB system transformed sequentially from a viscoelastic solution to an aqueous surfactant two-phase system (ASTP), an aqueous surfactant three-phase system (AS3P), and an anisotropic homogeneous phase as the concentration of C14 -MPA-Na was continuously increased from 10 to 35 mm. The C16 -MPA-Na/CTAB system showed similar phase behavior, whereas the C12 -MPA-Na/CTAB system did not form the AS3P system. The corresponding microstructures in the different phases were investigated by using rheology and cryogenic transmission electron microscopy (Cryo-TEM). The aggregates in the viscoelastic solutions are thread-like, annular, and worm-like micelles. The microstructures in the upper phase of the ASTP are worm-like micelles, and in the lower phase are spherical and rod-like micelles. The aggregates in the upper and lower phases of the AS3P are worm-like micelles and spherical and rod-like micelles, respectively. The aggregates in the middle phase of the AS3P and the anisotropic homogeneous phase are sponge-like micelles. The clear Cryo-TEM images of the sponge-like micelles are presented.

8.
Soft Matter ; 14(4): 499-507, 2018 Jan 24.
Artigo em Inglês | MEDLINE | ID: mdl-29303202

RESUMO

A novel bio-based anionic surfactant containing a large rigid group and a flexible alkyl chain, namely, sodium N-dodecyl-maleimidepimaric carboxylate (C12-MPA-Na), was synthesized from rosin. The molecular structure of C12-MPA-Na was identified using 1H NMR, FT-IR spectroscopy and MS. Despite containing 36 carbon atoms, C12-MPA-Na showed good water solubility at room temperature. Large spherical aggregates with diameters of 100-200 nm were formed by C12-MPA-Na when its concentration was above 0.1 mM, which was slightly higher than the critical micelle concentration (0.078 mM). Annular wormlike micelles were discovered with increasing C12-MPA-Na concentration, and began to change into extremely long threadlike wormlike micelles when the C12-MPA-Na concentration reached approximately 58 mM. The viscoelastic properties of the wormlike micelle solutions were investigated using steady state and oscillatory shear sweep rheological measurements. The zero-shear viscosity (η0) strongly depended on the concentration of C12-MPA-Na, and the scaling exponent was 34.1. Cryo-TEM confirmed the formation of large spherical aggregates and wormlike micelles. 1H-1H 2D nuclear Overhauser effect spectroscopy (NOESY) was used to detect the molecular interactions of C12-MPA-Na. The results indicated that the alkyl chain of C12-MPA-Na was partially overlapped with its non-planar rigid structure in aqueous solution, and the possible aggregation process for C12-MPA-Na was proposed.

9.
Molecules ; 23(2)2018 Feb 08.
Artigo em Inglês | MEDLINE | ID: mdl-29419733

RESUMO

Turpentine is a volatile component of resin, which is an abundant forest resource in Southern China. As one of the most important components, the integrated application of ß-pinene has been studied. The broad-spectrum evaluation of ß-pinene and its analogues has, therefore, been necessary. In an attempt to expand the scope of agro-activity trials, the preparation and the evaluation of the herbicidal activity of a series of ß-pinene analogues against three agricultural herbs were carried out. In accordance with the overall herbicidal activity, it is noteworthy that compounds 6k, 6l, and 6m demonstrated extreme activity with IC50 values of 0.065, 0.065, and 0.052 mol active ingredients/hectare against E. crus-galli. The preliminary structure-activity relationship (SAR) was analyzed and the compounds with the appropriate volatility and substituent type that had beneficial herbicidal activity were analyzed. Simultaneously, the quantitative structure-activity relationship (QSAR) model was built and the most important structural features were indicated, which was, to a certain extent, in line with the SAR study. The study aimed to study the application of the forest resource turpentine in agriculture as a potential and alternative approach for comprehensive utilization.


Assuntos
Produção Agrícola , Terebintina/análise , Terebintina/química , Monoterpenos Bicíclicos , Compostos Bicíclicos com Pontes/síntese química , Compostos Bicíclicos com Pontes/química , Herbicidas/química , Herbicidas/farmacologia , Modelos Moleculares , Estrutura Molecular , Monoterpenos/síntese química , Monoterpenos/química , Relação Quantitativa Estrutura-Atividade , Eletricidade Estática , Terebintina/farmacologia
10.
Bioorg Med Chem Lett ; 26(6): 1512-1515, 2016 Mar 15.
Artigo em Inglês | MEDLINE | ID: mdl-26898336

RESUMO

A series of novel 3-cyanopyridine derivatives of (-)-ß-pinene were designed and synthesized by one-pot four-component domino reactions. The targeted compounds were evaluated for their antimicrobial activity against four bacteria (Klebsiella pneumoniae, Enterobacter aerogenes, Staphylococcus aureus, Staphylococcus epidermidis) and a fungus (Candida albicans). The results showed that most of the minimal inhibitory concentrations (MICs) of these 3-cyanopyridine derivatives against the tested strains was in the range of 15.6-125 mg/L. Among these 3-cyanopyridine derivatives, the MICs of compound 5h against S. epidermidis and C. albicans were 15.6 mg/L, which revealed that compound 5h featured double fluoro substituents at meta- and para-position was the most active compound. In addition, the preliminary structure-activity relationship analysis indicated that the change of substituents on the pyridine ring and benzene ring of 3-cyanopyridine derivatives was an important factor for inducing antimicrobial activity. This research would promote the development of heterocyclic derivatives of ß-pinene with antimicrobial activity.


Assuntos
Antibacterianos/síntese química , Antibacterianos/farmacologia , Antifúngicos/síntese química , Antifúngicos/farmacologia , Compostos Bicíclicos com Pontes/química , Compostos Bicíclicos com Pontes/farmacologia , Monoterpenos/química , Monoterpenos/farmacologia , Piridinas/química , Antibacterianos/química , Antifúngicos/química , Bactérias/efeitos dos fármacos , Monoterpenos Bicíclicos , Compostos Bicíclicos com Pontes/síntese química , Relação Dose-Resposta a Droga , Fungos/efeitos dos fármacos , Testes de Sensibilidade Microbiana , Estrutura Molecular , Monoterpenos/síntese química , Piridinas/farmacologia , Estereoisomerismo , Relação Estrutura-Atividade
11.
Bioorg Med Chem Lett ; 24(3): 773-9, 2014 Feb 01.
Artigo em Inglês | MEDLINE | ID: mdl-24418774

RESUMO

Molecular interactions between terpenoid mosquito repellents and three typical human-secreted attractants, ammonia, 1-octen-3-ol, and formic acid were studied. Relative energies, bond distances, and bond angles of the molecular interactions were obtained at HF level to evaluate the interaction intensity and types. The effects of molecular interactions on repellency were investigated by the subsequent quantitative structure-activity relationship (QSAR) study. The results of this study suggest that attractant-repellent interaction should not be ignored and could be helpful for future research on the repelling mechanism of mosquito repellents.


Assuntos
Amônia/química , Formiatos/química , Repelentes de Insetos/química , Octanóis/química , Terpenos/química , Animais , Complexos de Coordenação/química , Humanos , Estrutura Molecular , Controle de Mosquitos , Relação Quantitativa Estrutura-Atividade
12.
Int J Biol Macromol ; 274(Pt 1): 133050, 2024 Aug.
Artigo em Inglês | MEDLINE | ID: mdl-38880451

RESUMO

Practical employment of silicon (Si) electrodes in lithium-ion batteries (LIBs) is limited due to the severe volume changes suffered during charging-discharging process, causing serious capacity fading. Here, a composite polymer (CP-10) containing sodium carboxymethyl cellulose (CMC-Na) and poly-lysine (PL) is proposed for the binder of Si-based anodes, and a multifunctional strategy of "in-situ crosslinking" is achieved to alleviate the severe capacity degradation effectively. A cross-linked three-dimensional (3D) network is established through the strong hydrogen bonding interaction and reversible electrostatic interactions within CP-10, offering favorable mechanical tolerance for the extreme volume expansion of Si. Moreover, hydrogen bonding interaction along with ion-dipole interaction formed between CP-10 and Si surface enhance the bonding capability of Si-based anodes, promoting the maintenance of anodes' integrity. Consequently, over 800 cycles are achieved for the Si@CP-10 at 0.5C while maintaining a fixed discharge specific capacity of 1000 mAh g-1. Moreover, the Si/C@CP-10 can stably operate over 500 cycles with a capacity retention of 77.12 % at 1C. The prolonged cycling lifetime of Si/C and Si anodes suggests great potential for this strategy in promoting the implementation of high-capacity LIBs.


Assuntos
Carboximetilcelulose Sódica , Eletrodos , Polilisina , Silício , Carboximetilcelulose Sódica/química , Silício/química , Polilisina/química , Fontes de Energia Elétrica , Reagentes de Ligações Cruzadas/química , Lítio/química
13.
ACS Appl Mater Interfaces ; 16(5): 6523-6532, 2024 Feb 07.
Artigo em Inglês | MEDLINE | ID: mdl-38275160

RESUMO

Thermosetting foams have limited capabilities for recycling, reprocessing, or reshaping. Moreover, most of the foaming agents currently employed in these foams are derived from organic compounds sourced from petrochemicals, thereby posing a significant environmental threat due to heightened pollution. To solve these problems, a fully biobased degradable vitrimer foam (EPC-X) was fabricated using an environmentally friendly all-in-one foaming strategy by cross-linking epoxidized malepimaric anhydride (EMPA), 1,5-diaminopentane (PDA), and 1,5-diaminopentane carbamate (PDAC) as a latent curing-blowing agent. To our delight, the vitrimer foams exhibit excellent mechanical properties (2.86 ± 0.11 MPa compressive strength) owing to their unique rigid rosin backbone and cross-linking networks. The presence of dynamic ß-hydroxy ester bonds and the self-catalytic behavior of tertiary amine groups facilitate network rearrangement without requiring additional catalysts, thereby resulting in the development of EPC-X with rapid self-healing and shape memory properties. The self-healing foam could support a weight of 500 g (approximately 562 times its own mass). Moreover, these high-performance vitrimer foams can also be easily degraded in an ethanolamine (EA) or NaOH solution under mild conditions. Such a design strategy offers an alternative approach for developing superior degradable and thermal stimuli-responsive thermosetting foams.

14.
J Agric Food Chem ; 72(2): 973-982, 2024 Jan 17.
Artigo em Inglês | MEDLINE | ID: mdl-38166361

RESUMO

To develop new antioomycete agents against plant pathogens, two series of acrylopimaric acid triazole derivatives from rosin were synthesized. The in vitro antioomycete activity of these derivatives was evaluated and screened against Pseudoperonospora cubensisi, Plasmopara viticola, Phytophthora sojae, Phytophthora infestans, and Phytophthora capsici. Compound 5m showed the highest antioomycete activity against P. capsici, with a half-maximal effective concentration (EC50) value that was lower than that of the positive control metalaxyl (1.391 and 1.815 mg/L, respectively). Compound 5m demonstrated satisfactory protective and curative efficacy against P. capsici in pepper in in vivo antioomycete activity studies. Physiological and biochemical testing showed that the action mechanism of compound 5m on P. capsici involved altering the morphology and ultrastructure of the mycelium, increasing cell membrane permeability, inducing dysfunction of the nucleus and mitochondria, and ultimately causing cell necrosis. In addition, the analysis of three-dimensional quantitative structure-activity relationship (3D-QSAR) revealed the significance of the molecular structure and charge distribution in the interaction between compound 5m and its target. Collectively, these findings indicate that compound 5m has the potential as an antioomycete candidate.


Assuntos
Phytophthora infestans , Estrutura Molecular , Plantas , Alimentos , Relação Quantitativa Estrutura-Atividade , Doenças das Plantas
15.
Artigo em Inglês | MEDLINE | ID: mdl-38597955

RESUMO

A nanomicrocapsule system was constructed through the polymerization of tannic acid (TA) and emulsifier OP-10 (OP-10), followed by the chelation of iron ions, to develop a safe and effective method for controlling Rhizoctonia solani in agriculture. The encapsulated active component is a rosin-based triazole derivative (RTD) previously synthesized by our research group (RTD@OP10-TA-Fe). The encapsulation efficiency of the nanomicrocapsules is 82.39%, with an effective compound loading capacity of 96.49%. Through the encapsulation of the RTD via nanomicrocapsules, we improved its water solubility, optimized its stability, and increased its adhesion to the leaf surface. Under acidic conditions (pH = 5.0), the release rate of nanomicrocapsules at 96 h is 96.31 ± 0.8%, which is 2.04 times higher than the release rate under normal conditions (pH = 7.0). Additionally, the results of in vitro and in vivo antifungal assays indicate that compared with the original compound, the nanomicrocapsules exhibit superior antifungal activity (EC50 values of RTD and RTD@OP10-TA-Fe are 1.237 and 0.860 mg/L, respectively). The results of field efficacy trials indicate that compared with RTD, RTD@OP10-TA-Fe exhibits a more prolonged period of effectiveness. Even after 3 weeks, the antifungal rate of RTD@OP10-TA-Fe remains at 40%, whereas RTD, owing to degradation, shows an antifungal rate of 11.11% during the same period. Furthermore, safety assessment results indicate that compared with the control, RTD@OP10-TA-Fe has almost no impact on the growth of rice seedlings and exhibits low toxicity to zebrafish. This study provides valuable insights into controlling R. solani and enhancing the compound performance.

16.
J Agric Food Chem ; 72(9): 4630-4638, 2024 Mar 06.
Artigo em Inglês | MEDLINE | ID: mdl-38407939

RESUMO

To investigate the potential application value of dehydroabietic acid, 27 novel dehydroabietyl-1,2,4-triazole-5-thioether-based derivatives were designed and characterized by IR, 1H NMR, 13C NMR, and LC-MS. Their antifungal activities were evaluated against five plant fungi, namely, Valsa mali, Colletotrichum orbiculare, Fusarium graminearum, Sclerotinia sclerotiorum, and Gaeumannomyces graminis; the results showed that compound 5h-1 (Co. 5h-1) exhibited a considerable inhibitory effect against V. mali. Moreover, in vivo experiments indicated that Co. 5h-1 had a certain protective effect on apple branches. The preliminary structure-activity relationship analysis suggested that the electron-withdrawing group on the benzyl group was significantly better than that of other substituent derivatives. Through electron microscopy analysis, it was found that Co. 5h-1 hindered the growth of mycelia, damaged their cell structure, and caused the large accumulation of reactive oxygen species (ROS). Preliminary research on the mode of action indicated that Co. 5h-1 could affect the activity of CAT by increasing the α-helix (0.790%), decreasing the ß-sheet (0.170%), which led to the accumulation of ROS. In addition, Co. 5h-1 also affected the activity of CYP51, hindered the biosynthesis of ergosterol, and increased cell membrane permeability. Overall, this above research proposed that Co. 5h-1 can be a novel leading structure for development of a fungicide agent.


Assuntos
Antifúngicos , Ascomicetos , Fungicidas Industriais , Resinas Vegetais , Antifúngicos/química , Proteção de Cultivos , Espécies Reativas de Oxigênio , Relação Estrutura-Atividade , Triazóis/farmacologia , Triazóis/química , Fungicidas Industriais/farmacologia , Fungicidas Industriais/química
17.
Pest Manag Sci ; 2024 Jul 19.
Artigo em Inglês | MEDLINE | ID: mdl-39032014

RESUMO

BACKGROUND: Utilizing fungicides to protect crops from diseases is an effective method, and novel eco-friendly plant-derived fungicides with high efficiency and low toxicity are urgent requirements for sustainable crop protection. RESULT: Two series of rosin-based fungicides (totally 35) were designed and synthesized. In vitro fungicidal activity revealed that Compound 6a (Co. 6a) effectively inhibited the growth of Valsa mali [median effective concentration (EC50) = 0.627 µg mL-1], and in vivo fungicidal activity suggested a significant protective efficacy of Co. 6a in protecting both apple branches (35.12% to 75.20%) and apples (75.86% to 90.82%). Quantum chemical calculations (via density functional theory) results indicated that the primary active site of Co. 6a lies in its amide structure. Mycelial morphology and physiology were investigated to elucidate the mode-of-action of Co. 6a, and suggested that Co. 6a produced significant cell membrane damage, accelerated electrolyte leakage, decreased succinate dehydrogenase (SDH) protein activity, and impaired physiological and biochemical functions, culminating in mycelial mortality. Molecular docking analysis revealed a robust binding energy (ΔE = -7.29 kcal mol-1) between Co. 6a and SDH. Subsequently, biosafety evaluations confirmed the environmentally-friendly nature of Co. 6a via the zebrafish model, yet toxicological results indicated that Co. 6a at median lethal concentration [LC50(96)] damaged the gills, liver and intestines of zebrafish. CONCLUSION: The above research offers a theoretical foundation for exploiting eco-friendly rosin-based fungicidal candidates in sustainable crop protection. © 2024 Society of Chemical Industry.

18.
Pest Manag Sci ; 80(8): 3988-3996, 2024 Aug.
Artigo em Inglês | MEDLINE | ID: mdl-38529554

RESUMO

BACKGROUND: To further develop potential natural fungicides, two series of new acrylopimaric acid triazole derivatives were synthesized, and their antifungal activities were tested and evaluated. RESULTS: In vitro antifungal activity results indicated that compound 5m exhibited significant inhibitory activity against Rhizoctonia solani with an half maximal effective concentration (EC50) value of 1.528 mg/L. Its antifungal effect was comparable to that of the commercially available fungicide fluconazole, epoxiconazole and propiconazole (EC50 values of 1.441, 0.815 and 1.173 mg/L). Subsequently, in vivo studies were conducted on compound 5m, which revealed its significant protective and curative effects against R. solani. In addition, physiological and biochemical studies showed that compound 5m could disrupt the morphology and ultrastructure of R. solani mycelium, increase cell membrane permeability, inhibit ergosterol synthesis, and enhance the activity of defense enzymes in rice plants. Three-dimensional quantitative structure-activity relationship (3D-QSAR) studies revealed that the molecular structure significantly influenced the binding of compound 5m to the receptor, thereby enhancing its antifungal activity. CONCLUSION: Compound 5m exhibits excellent antifungal activity against R. solani, making it a promising candidate fungicide for the prevention and control of R. solani. © 2024 Society of Chemical Industry.


Assuntos
Fungicidas Industriais , Rhizoctonia , Triazóis , Triazóis/farmacologia , Triazóis/química , Rhizoctonia/efeitos dos fármacos , Fungicidas Industriais/farmacologia , Fungicidas Industriais/química , Relação Quantitativa Estrutura-Atividade , Oryza , Antifúngicos/farmacologia , Antifúngicos/química , Doenças das Plantas/microbiologia , Doenças das Plantas/prevenção & controle
19.
Int J Biol Macromol ; 267(Pt 2): 131536, 2024 May.
Artigo em Inglês | MEDLINE | ID: mdl-38608993

RESUMO

Cellulosic hydrogels are widely used in various applications, as they are natural raw materials and have excellent degradability. However, their poor mechanical properties restrict their practical application. This study presents a facile approach for fabricating cellulosic hydrogels with high strength by synergistically utilizing salting-out and ionic coordination, thereby inducing the collapse and aggregation of cellulose chains to form a cross-linked network structure. Cellulosic hydrogels are prepared by soaking cellulose in an Al2(SO4)3 solution, which is both strong (compressive strength of up to 16.99 MPa) and tough (compressive toughness of up to 2.86 MJ/m3). The prepared cellulosic hydrogels exhibit resistance to swelling in different solutions and good biodegradability in soil. The cellulosic hydrogels are incorporated into strain sensors for human-motion monitoring by introducing AgNWs. Thus, the study offers a promising, simple, and scalable approach for preparing strong, degradable, and anti-swelling hydrogels using common biomass resources with considerable potential for various applications.


Assuntos
Celulose , Hidrogéis , Hidrogéis/química , Celulose/química , Força Compressiva , Humanos , Íons/química
20.
Bioorg Med Chem Lett ; 23(7): 2254-9, 2013 Apr 01.
Artigo em Inglês | MEDLINE | ID: mdl-23481652

RESUMO

A new fluorescent probe (methyl 13-(α-naphthalene)aminodeisopropyldehydroabietate) has been synthesized, and its structure was optimized by theoretical DFT calculation and determinated by single-crystal X-ray diffraction analysis. The optimized data are in agreement with the experimental values. The fluorescence properties, photostability, cell toxicity and in vitro fluorescence imaging of the compound have been investigated. The results indicated that it can be effectively taken up by HeLa, 7721, 7901 and A549 cells and strong blue fluorescence signals were detected in these cells.


Assuntos
Abietanos/química , Aminas/química , Corantes Fluorescentes/química , Abietanos/síntese química , Abietanos/farmacologia , Aminas/síntese química , Aminas/farmacologia , Linhagem Celular Tumoral , Sobrevivência Celular/efeitos dos fármacos , Cristalografia por Raios X , Fluorescência , Corantes Fluorescentes/síntese química , Corantes Fluorescentes/farmacologia , Células HeLa , Humanos , Modelos Moleculares , Estrutura Molecular , Teoria Quântica , Espectrometria de Fluorescência
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