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1.
Food Res Int ; 188: 114325, 2024 Jul.
Artigo em Inglês | MEDLINE | ID: mdl-38823824

RESUMO

In this study, inactivation of mushroom polyphenol oxidase (PPO) by low intensity direct current (DC) electric field and its molecular mechanism were investigated. In the experiments under 3 V/cm, 5 V/cm, 7 V/cm and 9 V/cm electric fields, PPOs were all completely inactivated after different exposure times. Under 1 V/cm, a residual activity of 11.88 % remained. The inactivation kinetics confirms to Weibull model. Under 1-7 V/cm, n value closes to a constant about 1.3. The structural analysis of PPO under 3 V/cm and 5 V/cm by fluorescence emission spectroscopy and molecular dynamics (MD) simulation showed that the tertiary structure was slightly changed with increased radius of gyration, higher potential energy and rate of C-alpha fluctuation. After exposure to the electric field, most of the hydrophobic tryptophan (TRP) residues turned to the hydrophilic surface, resulting the fluorescence red-shifted and quenched. Molecular docking indicated that the receptor binding domain of catechol in PPO was changed. PPO under electric field was MD simulated the first time, revealing the changing mechanism of the electric field itself on PPO, a binuclear copper enzyme, which has a metallic center. All these suggest that the low intensity DC electric field would be a promising option for enzymatic browning inhibition or even enzyme activity inactivation.


Assuntos
Catecol Oxidase , Simulação de Acoplamento Molecular , Simulação de Dinâmica Molecular , Catecol Oxidase/metabolismo , Catecol Oxidase/química , Espectrometria de Fluorescência , Cinética , Eletricidade , Agaricales/enzimologia , Catecóis/química , Catecóis/metabolismo
2.
Yakugaku Zasshi ; 144(6): 643-650, 2024.
Artigo em Japonês | MEDLINE | ID: mdl-38825473

RESUMO

Inspired by the mechanism by which microorganisms utilize siderophores to ingest iron, four different FeIII complexes of typical artificial siderophore ligands containing catecholate and/or hydroxamate groups, K3[FeIII-LC3], K2[FeIII-LC2H1], K[FeIII-LC1H2], and [FeIII-LH3], were prepared. They were modified on an Au substrate surface (Fe-L/Au) and applied as microorganism immobilization devices for fast, sensitive, selective detection of microorganisms, where H6LC3, H5LC2H1, H4LC1H2, and H3LH3 denote the tri-catecholate, biscatecholate-monohydroxamate, monocatecholate-bishydroxamate, and tri-hydroxamate type of artificial siderophores, respectively. Their adsorption properties for the several microorganisms were investigated using scanning electron microscopy (SEM), quartz crystal microbalance (QCM), and electric impedance spectroscopy (EIS) methods. The artificial siderophore-iron complexes modified on the Au substrates Fe-LC3/Au, Fe-LC2H1/Au, Fe-LC1H2/Au, and Fe-LH3/Au showed specific microorganism immobilization behavior with selectivity based on the structure of the artificial siderophores. Their specificities corresponded well with the structural characteristics of natural siderophores that microorganisms release from the cell and/or use to take up an iron. These findings suggest that release and uptake are achieved through specific interactions between the artificial siderophore-FeIII complexes and receptors on the cell surfaces of microorganisms. This study revealed that Fe-L/Au systems have specific potential to serve as effective immobilization probes of microorganisms for rapid, selective detection and identification of a variety of microorganisms.


Assuntos
Sideróforos , Ouro , Ferro , Adsorção , Células Imobilizadas , Técnicas de Microbalança de Cristal de Quartzo , Microscopia Eletrônica de Varredura , Ligantes , Catecóis , Ácidos Hidroxâmicos
3.
J Mass Spectrom ; 59(6): e5036, 2024 Jun.
Artigo em Inglês | MEDLINE | ID: mdl-38726689

RESUMO

Turmeric and ginger are extensively employed as functional ingredients due to their high content of curcuminoids and gingerols, considered the key bioactive compounds found in these roots. In this study, we present an innovative and fast method for the assay of curcuminoids and gingerols in different foods containing the two spices, with the aim of monitoring the quality of products from a nutraceutical perspective. The proposed approach is based on paper spray tandem mass spectrometry coupled with the use of a labeled internal standard, which has permitted to achieve the best results in terms of specificity and accuracy. All the calculated analytical parameters were satisfactory; accuracy values are around 100% for all spiked samples and the precision data result lower than 15%. The protocol was applied to several real samples, and to demonstrate its robustness and reliability, the results were compared to those arising from the common liquid chromatographic method.


Assuntos
Curcuma , Álcoois Graxos , Espectrometria de Massas em Tandem , Zingiber officinale , Zingiber officinale/química , Curcuma/química , Espectrometria de Massas em Tandem/métodos , Álcoois Graxos/análise , Reprodutibilidade dos Testes , Limite de Detecção , Catecóis/análise , Análise de Alimentos/métodos , Curcumina/análise , Curcumina/análogos & derivados , Papel
4.
Molecules ; 29(9)2024 May 03.
Artigo em Inglês | MEDLINE | ID: mdl-38731606

RESUMO

The polyphenol-Maillard reaction is considered one of the important pathways in the formation of humic-like substances (HLSs). Glucose serves as a microbial energy source that drives the humification process. However, the effects of changes in glucose, particularly its concentration, on abiotic pathways remain unclear. Given that the polyphenol-Maillard reaction requires high precursor concentrations and elevated temperatures (which are not present in soil), gibbsite was used as a catalyst to overcome energetic barriers. Catechol and glycine were introduced in fixed concentrations into a phosphate-buffered solution containing gibbsite using the liquid shake-flask incubation method, while the concentration of glucose was controlled in a sterile incubation system. The supernatant fluid and HLS components were dynamically extracted over a period of 360 h for analysis, thus revealing the influence of different glucose concentrations on abiotic humification pathways. The results showed the following: (1) The addition of glucose led to a higher degree of aromatic condensation in the supernatant fluid. In contrast, the supernatant fluid without glucose (Glu0) and the control group without any Maillard precursor (CK control group) exhibited lower degrees of aromatic condensation. Although the total organic C (TOC) content in the supernatant fluid decreased in all treatments during the incubation period, the addition of Maillard precursors effectively mitigated the decreasing trend of TOC content. (2) While the C content of humic-like acid (CHLA) and the CHLA/CFLA ratio (the ratio of humic-like acid to fulvic-like acid) showed varying increases after incubation, the addition of Maillard precursors resulted in a more noticeable increase in CHLA content and the CHLA/CFLA ratio compared to the CK control group. This indicated that more FLA was converted into HLA, which exhibited a higher degree of condensation and humification, thus improving the quality of HLS. The addition of glycine and catechol without glucose or with a glucose concentration of 0.06 mol/L was particularly beneficial in enhancing the degree of HLA humification. Furthermore, the presence of glycine and catechol, as well as higher concentrations of glucose, promoted the production of N-containing compounds in HLA. (3) The presence of Maillard precursors enhanced the stretching vibration of the hydroxyl group (-OH) of HLA. After the polyphenol-Maillard reaction of glycine and catechol with glucose concentrations of 0, 0.03, 0.06, 0.12, or 0.24 mol/L, the aromatic C structure in HLA products increased, while the carboxyl group decreased. The presence of Maillard precursors facilitated the accumulation of polysaccharides in HLA with higher glucose concentrations, ultimately promoting the formation of Al-O bonds. However, the quantities of phenolic groups and phenols in HLA decreased to varying extents.


Assuntos
Glucose , Substâncias Húmicas , Reação de Maillard , Polifenóis , Substâncias Húmicas/análise , Glucose/química , Glucose/metabolismo , Polifenóis/química , Catecóis/química
5.
Breast Dis ; 43(1): 99-110, 2024.
Artigo em Inglês | MEDLINE | ID: mdl-38758988

RESUMO

INTRODUCTION: Indonesian civilization extensively uses traditional medicine to cure illnesses and preserve health. The lack of knowledge on the security and efficacy of medicinal plants is still a significant concern. Although the precise chemicals responsible for this impact are unknown, ginger is a common medicinal plant in Southeast Asia that may have anticancer qualities. METHOD: Using data from Dudedocking, a machine-learning model was created to predict possible breast anticancer chemicals from ginger. The model was used to forecast substances that block KIT and MAPK2 proteins, essential elements in breast cancer. RESULT: Beta-carotene, 5-Hydroxy-74'-dimethoxyflavone, [12]-Shogaol, Isogingerenone B, curcumin, Trans-[10]-Shogaol, Gingerenone A, Dihydrocurcumin, and demethoxycurcumin were all superior to the reference ligand for MAPK2, according to molecular docking studies. Lycopene, [8]-Shogaol, [6]-Shogaol, and [1]-Paradol exhibited low toxicity and no Lipinski violations, but beta carotene had toxic predictions and Lipinski violations. It was anticipated that all three substances would have anticarcinogenic qualities. CONCLUSION: Overall, this study shows the value of machine learning in drug development and offers insightful information on possible anticancer chemicals from ginger.


Assuntos
Neoplasias da Mama , Aprendizado de Máquina , Simulação de Acoplamento Molecular , Zingiber officinale , Zingiber officinale/química , Humanos , Neoplasias da Mama/tratamento farmacológico , Feminino , Extratos Vegetais/farmacologia , Simulação por Computador , Antineoplásicos Fitogênicos/farmacologia , Catecóis/farmacologia
6.
Anal Chim Acta ; 1311: 342739, 2024 Jul 04.
Artigo em Inglês | MEDLINE | ID: mdl-38816161

RESUMO

BACKGROUND: Catechol (CC), a prevalent phenolic compound, is a byproduct in various agricultural, chemical, and industrial processes. CC detection is crucial for safeguarding water quality and plays a pivotal role in enhancing the overall quality of life of individuals. Electrochemical biosensors exhibit rapid responses, have small sizes, and can be used for real-time monitoring. Therefore, the development of a fast and sensitive electrochemical biosensor for CC detection is crucial. RESULT: In this study, a laccase-based electrochemical biosensor for detection of CC is successfully developed using Fe3O4 nanoparticles as medium and optimized by applying a magnetic field. This research proposes a unique strategy for biosensor enhancement by actively controlling the distribution of magnetic materials on the electrode surface through the application of a magnetic field, resulting in a visibly alternating stripe pattern. This approach effectively disperses magnetic particles, preventing their aggregation and reducing the boundary layer thickness, enhancing the electrochemical response of the biosensor. After fabrication condition optimization, CC is successfully detected using this biosensor. The fabricated sensor exhibits excellent performance with a wide linear detection range of 10-1000 µM, a low detection limit of 1.25 µM, and a sensitivity of 7.9 µA/mM. The fabricated sensor exhibits good selectivity and reliable detection in real water samples. In addition, the laccase-based sensor has the potential for the fast and accurate monitoring of CC in olive oil. SIGNIFICANCE: The magnetic field optimization in this study significantly improved the performance of the electrochemical biosensor for detecting CC in environmental samples. Overall, the sensor developed in this study has the potential for fast and accurate monitoring of CC in environmental samples, highlighting the potential importance of a magnetic field environment in improving the performance of catechol electrochemical biosensors.


Assuntos
Técnicas Biossensoriais , Catecóis , Técnicas Eletroquímicas , Lacase , Catecóis/análise , Catecóis/química , Lacase/química , Lacase/metabolismo , Campos Magnéticos , Nanopartículas de Magnetita/química , Eletrodos , Propriedades de Superfície , Limite de Detecção , Enzimas Imobilizadas/química , Enzimas Imobilizadas/metabolismo , Poluentes Químicos da Água/análise
7.
Food Chem ; 452: 139425, 2024 Sep 15.
Artigo em Inglês | MEDLINE | ID: mdl-38744128

RESUMO

Effect of puffing on conversion of gingerols to shogaols, physicochemical properties as well as antioxidant and anti-inflammatory activities of puffed ginger was investigated. Puffing significantly increased extraction yield and the highest value was 12.52% at 980 kPa. The significant decrease in gingerols and increase in shogaols were occurred after puffing, respectively. Especially, 6-shogaol was dramatically increased from 4.84 to 99.10 mg/g dried ginger. Puffed ginger exhibited the higher antioxidant activities (analyzed by DPPH, ABTS, TPC, and TFC) than those of control, and they were significantly increased with increasing puffing pressure. In case of anti-inflammatory activity, puffed ginger did not inhibit NO production, but significantly inhibited TNF-α and IL-6 productions. Among gingerols and shogaols, 6-shogaol showed significantly strong correlations with both antioxidant and anti-inflammatory activities. Consequently, puffed ginger can be applied to functional food industry, which dramatically increased the contents of 6, 8, 10-shogaols, the main bioactive compounds in ginger.


Assuntos
Anti-Inflamatórios , Antioxidantes , Catecóis , Álcoois Graxos , Extratos Vegetais , Zingiber officinale , Zingiber officinale/química , Catecóis/química , Catecóis/análise , Antioxidantes/química , Anti-Inflamatórios/química , Anti-Inflamatórios/farmacologia , Álcoois Graxos/química , Álcoois Graxos/análise , Álcoois Graxos/farmacologia , Extratos Vegetais/química , Extratos Vegetais/farmacologia , Animais , Camundongos
8.
Nutrients ; 16(9)2024 Apr 26.
Artigo em Inglês | MEDLINE | ID: mdl-38732549

RESUMO

Oleocanthal (OC) is a monophenol of extra-virgin olive oil (EVOO) endowed with antibiotic, cardioprotective and anticancer effects, among others, mainly in view of its antioxidant and anti-inflammatory properties. OC has been largely investigated in terms of its anticancer activity, in Alzheimer disease and in collagen-induced arthritis; however, the possibility that it can also affect muscle biology has been totally overlooked so far. This study is the first to describe that OC modulates alterations induced in C2C12 myotubes by stimuli known to induce muscle wasting in vivo, namely TNF-α, or in the medium conditioned by the C26 cachexia-inducing tumor (CM-C26). C2C12 myotubes were exposed to CM-C26 or TNF-α in the presence or absence of OC for 24 and 48 h and analyzed by immunofluorescence and Western blotting. In combination with TNF-α or CM-C26, OC was revealed to be able to restore both the myotube's original size and morphology and normal levels of both atrogin-1 and MuRF1. OC seems unable to impinge on the autophagic-lysosomal proteolytic system or protein synthesis. Modulations towards normal levels of the expression of molecules involved in myogenesis, such as Pax7, myogenin and MyHC, were also observed in the myotube cultures exposed to OC and TNF-α or CM-C26. In conclusion, the data presented here show that OC exerts a protective action in C2C12 myotubes exposed to TNF-α or CM-C26, with mechanisms likely involving the downregulation of ubiquitin-proteasome-dependent proteolysis and the partial relief of myogenic differentiation impairment.


Assuntos
Catecóis , Monoterpenos Ciclopentânicos , Fibras Musculares Esqueléticas , Proteínas Musculares , Atrofia Muscular , Fator de Necrose Tumoral alfa , Animais , Fibras Musculares Esqueléticas/efeitos dos fármacos , Fibras Musculares Esqueléticas/metabolismo , Camundongos , Fator de Necrose Tumoral alfa/metabolismo , Atrofia Muscular/prevenção & controle , Atrofia Muscular/metabolismo , Proteínas Musculares/metabolismo , Monoterpenos Ciclopentânicos/farmacologia , Catecóis/farmacologia , Linhagem Celular , Proteínas Ligases SKP Culina F-Box/metabolismo , Proteínas Ligases SKP Culina F-Box/genética , Desenvolvimento Muscular/efeitos dos fármacos , Proteínas com Motivo Tripartido/metabolismo , Proteínas com Motivo Tripartido/genética , Ubiquitina-Proteína Ligases/metabolismo , Autofagia/efeitos dos fármacos , Fenóis/farmacologia , Caquexia/prevenção & controle , Meios de Cultivo Condicionados/farmacologia , Aldeídos
9.
Nutrients ; 16(9)2024 Apr 25.
Artigo em Inglês | MEDLINE | ID: mdl-38732529

RESUMO

The Mediterranean diet, renowned for its health benefits, especially in reducing cardiovascular risks and protecting against diseases like diabetes and cancer, emphasizes virgin olive oil as a key contributor to these advantages. Despite being a minor fraction, the phenolic compounds in olive oil significantly contribute to its bioactive effects. This review examines the bioactive properties of hydroxytyrosol and related molecules, including naturally occurring compounds (-)-oleocanthal and (-)-oleacein, as well as semisynthetic derivatives like hydroxytyrosyl esters and alkyl ethers. (-)-Oleocanthal and (-)-oleacein show promising anti-tumor and anti-inflammatory properties, which are particularly underexplored in the case of (-)-oleacein. Additionally, hydroxytyrosyl esters exhibit similar effectiveness to hydroxytyrosol, while certain alkyl ethers surpass their precursor's properties. Remarkably, the emerging research field of the effects of phenolic molecules related to virgin olive oil on cell autophagy presents significant opportunities for underscoring the anti-cancer and neuroprotective properties of these molecules. Furthermore, promising clinical data from studies on hydroxytyrosol, (-)-oleacein, and (-)-oleocanthal urge further investigation and support the initiation of clinical trials with semisynthetic hydroxytyrosol derivatives. This review provides valuable insights into the potential applications of olive oil-derived phenolics in preventing and managing diseases associated with cancer, angiogenesis, and atherosclerosis.


Assuntos
Inibidores da Angiogênese , Azeite de Oliva , Fenóis , Álcool Feniletílico , Azeite de Oliva/química , Humanos , Fenóis/farmacologia , Inibidores da Angiogênese/farmacologia , Álcool Feniletílico/análogos & derivados , Álcool Feniletílico/farmacologia , Dieta Mediterrânea , Aterosclerose/prevenção & controle , Aterosclerose/tratamento farmacológico , Monoterpenos Ciclopentânicos , Neoplasias/prevenção & controle , Neoplasias/tratamento farmacológico , Catecóis/farmacologia , Aldeídos/farmacologia , Animais , Antineoplásicos/farmacologia , Anti-Inflamatórios/farmacologia
10.
Food Chem ; 453: 139638, 2024 Sep 30.
Artigo em Inglês | MEDLINE | ID: mdl-38781898

RESUMO

As primary polyphenol oxidant products, the occurrence of o-quinone is greatly responsible for quality deterioration in wine, including browning and aroma loss. The high reactivity of o-quinone causes huge difficulty in its determination. Herein, a derivative strategy combined with UHPLC-MS/MS analysis was established with chlorogenic acid quinone (CQAQ) and 4-methylcatechol quinone (4MCQ) as model compounds. Method validation demonstrated its efficiency for two analytes (R2 > 0.99, accuracy 98.71-106.39 %, RSD of precision 0.46-6.11 %, recovery 85.83-99.37 %). This approach was successfully applied to detect CQAQ and 4MCQ, suggesting its applicability in food analysis. CQAQ in coffee was much more than 4MCQ and with the deepening of baking degree, CQAQ decreased and 4MCQ increased. The amounts of CQAQ in various vegetables were markedly different, seemingly consistent with their respective browning degrees in practical production. This study developed an accurate and robust analytical approach for o-quinones, providing technical support for their further investigation in foods.


Assuntos
Quinonas , Espectrometria de Massas em Tandem , Cromatografia Líquida de Alta Pressão , Quinonas/química , Quinonas/análise , Verduras/química , Análise de Alimentos , Café/química , Ácido Clorogênico/análise , Ácido Clorogênico/química , Catecóis/análise , Catecóis/química
11.
ACS Appl Mater Interfaces ; 16(21): 26998-27010, 2024 May 29.
Artigo em Inglês | MEDLINE | ID: mdl-38748642

RESUMO

A coating that can be activated by moisture found in respiratory droplets could be a convenient and effective way to control the spread of airborne pathogens and reduce fomite transmission. Here, the ability of a novel 6-hydroxycatechol-containing polymer to function as a self-disinfecting coating on the surface of polypropylene (PP) fabric was explored. Catechol is the main adhesive molecule found in mussel adhesive proteins. Molecular oxygen found in an aqueous solution can oxidize catechol and generate a known disinfectant, hydrogen peroxide (H2O2), as a byproduct. However, given the limited amount of moisture found in respiratory droplets, there is a need to enhance the rate of catechol autoxidation to generate antipathogenic levels of H2O2. 6-Hydroxycatechol contains an electron donating hydroxyl group on the 6-position of the benzene ring, which makes catechol more susceptible to autoxidation. 6-Hydroxycatechol-coated PP generated over 3000 µM of H2O2 within 1 h when hydrated with a small amount of aqueous solution (100 µL of PBS). The generated H2O2 was three orders of magnitude higher when compared to the amount generated by unmodified catechol. 6-Hydroxycatechol-containing coating demonstrated a more effective antimicrobial effect against both Gram-positive (Staphylococcus aureus and Staphylococcus epidermidis) and Gram-negative (Pseudomonas aeruginosa and Escherichia coli) bacteria when compared to unmodified catechol. Similarly, the self-disinfecting coating reduced the infectivity of both bovine viral diarrhea virus and human coronavirus 229E by as much as a 2.5 log reduction value (a 99.7% reduction in viral load). Coatings containing unmodified catechol did not generate sufficient H2O2 to demonstrate significant virucidal effects. 6-Hydroxycatechol-containing coating can potentially function as a self-disinfecting coating that can be activated by the moisture present in respiratory droplets to generate H2O2 for disinfecting a broad range of pathogens.


Assuntos
Catecóis , Peróxido de Hidrogênio , Peróxido de Hidrogênio/química , Peróxido de Hidrogênio/farmacologia , Catecóis/química , Catecóis/farmacologia , Humanos , Staphylococcus aureus/efeitos dos fármacos , Desinfetantes/farmacologia , Desinfetantes/química , Polipropilenos/química , Antibacterianos/farmacologia , Antibacterianos/química , Escherichia coli/efeitos dos fármacos
12.
Int J Biol Macromol ; 270(Pt 2): 132174, 2024 Jun.
Artigo em Inglês | MEDLINE | ID: mdl-38750842

RESUMO

Hydrogels containing catechol group have received attention in the biomedical field due to their robust adhesive/cohesive capabilities, biocompatibility, and hemostatic abilities. Catechol-functionalized chitosan holds promise for preparing self-assembly hydrogels. However, issues of inefficient gelation and instability still persist in these hydrogels. In the current study, we synthesized chitosan catechol (CC) of high catechol substitution (∼28 %) and combined CC with tannic acid (TA, which also contains catechol) to form self-healing CC-TA hydrogels. The catechol-enriched CC-TA composite hydrogels showed rapid gelation and mechanical reinforcement (shear modulus ∼110 Pa). In situ coherent small-angle X-ray scattering (SAXS) coupled with rheometry revealed a morphological feature of mesoscale clusters (∼20 nm) within CC-TA hydrogel. The clusters underwent dynamic destruction under large-amplitude oscillatory shear, corresponding with the strain-dependent and self-healing behavior of the CC-TA hydrogel. The composite hydrogel had osmotic-responsive and notable adhesive properties. Meanwhile, CC-TA composite cryogel prepared simply through freeze-thawing procedures exhibited distinctive macroporous structure (∼200 µm), high water swelling ratio (∼7000 %), and favorable compressive modulus (∼8 kPa). The sponge-like cryogel was fabricated into swabs, demonstrating hemostatic capacity. The CC-TA composites, in both hydrogel and cryogel forms, possessed ROS scavenging ability, antimicrobial activity, and cell compatibility with potentials in biological applications.


Assuntos
Catecóis , Quitosana , Criogéis , Hemostáticos , Hidrogéis , Taninos , Quitosana/química , Quitosana/farmacologia , Catecóis/química , Catecóis/farmacologia , Taninos/química , Taninos/farmacologia , Criogéis/química , Hidrogéis/química , Hidrogéis/farmacologia , Hemostáticos/química , Hemostáticos/farmacologia , Anti-Infecciosos/farmacologia , Anti-Infecciosos/química , Animais , Reologia
13.
Int J Biol Macromol ; 270(Pt 1): 132294, 2024 Jun.
Artigo em Inglês | MEDLINE | ID: mdl-38735602

RESUMO

Polycyclic aromatic hydrocarbons (PAHs) are molecules with two or more fused aromatic rings that occur naturally in the environment due to incomplete combustion of organic substances. However, the increased demand for fossil fuels in recent years has increased anthropogenic activity, contributing to the environmental concentration of PAHs. The enzyme chlorocatechol 1,2-dioxygenase from Pseudomonas putida (Pp 1,2-CCD) is responsible for the breakdown of the aromatic ring of catechol, making it a potential player in bioremediation strategies. Pp 1,2-CCD can tolerate a broader range of substrates, including halogenated compounds, than other dioxygenases. Here, we report the construction of a chimera protein able to form biomolecular condensates with potential application in bioremediation. The chimera protein was built by conjugating Pp 1,2-CCD to low complex domains (LCDs) derived from the DEAD-box protein Dhh1. We showed that the chimera could undergo liquid-liquid phase separation (LLPS), forming a protein-rich liquid droplet under different conditions (variable protein and PEG8000 concentrations and pH values), in which the protein maintained its structure and main biophysical properties. The condensates were active against 4-chlorocatechol, showing that the chimera droplets preserved the enzymatic activity of the native protein. Therefore, it constitutes a prototype of a microreactor with potential use in bioremediation.


Assuntos
Biodegradação Ambiental , Dioxigenases , Hidrocarbonetos Policíclicos Aromáticos , Dioxigenases/metabolismo , Dioxigenases/química , Hidrocarbonetos Policíclicos Aromáticos/química , Hidrocarbonetos Policíclicos Aromáticos/metabolismo , Pseudomonas putida/enzimologia , Catecóis/metabolismo , Catecóis/química , Proteínas de Bactérias/química , Proteínas de Bactérias/metabolismo
14.
J Neuroimmune Pharmacol ; 19(1): 20, 2024 May 17.
Artigo em Inglês | MEDLINE | ID: mdl-38758335

RESUMO

Neuroinflammation has emerged as a crucial factor in the development of depression. Despite the well-known anti-inflammatory properties of 6-gingerol, its potential impact on depression remains poorly understood. This study aimed to investigate the antidepressant effects of 6-gingerol by suppressing microglial activation. In vivo experiments were conducted to evaluate the effect of 6-gingerol on lipopolysaccharide (LPS)-induced behavioral changes and neuroinflammation in rat models. In vitro studies were performed to examine the neuroprotective properties of 6-gingerol against LPS-induced microglial activation. Furthermore, a co-culture system of microglia and neurons was established to assess the influence of 6-gingerol on the expression of synaptic-related proteins, namely synaptophysin (SYP) and postsynaptic density protein 95 (PSD95), which are influenced by microglial activation. In the in vivo experiments, administration of 6-gingerol effectively alleviated LPS-induced depressive behavior in rats. Moreover, it markedly suppressed the activation of rat prefrontal cortex (PFC) microglia induced by LPS and the activation of the NF-κB/NLRP3 inflammatory pathway, while also reducing the levels of inflammatory cytokines IL-1ß and IL-18. In the in vitro experiments, 6-gingerol mitigated nuclear translocation of NF-κB p65, NLRP3 activation, and maturation of IL-1ß and IL-18, all of which were induced by LPS. Furthermore, in the co-culture system of microglia and neurons, 6-gingerol effectively restored the decreased expression of SYP and PSD95. The findings of this study demonstrate the neuroprotective effects of 6-gingerol in the context of LPS-induced depression-like behavior. These effects are attributed to the inhibition of microglial hyperactivation through the suppression of the NF-κB/NLRP3 inflammatory pathway.


Assuntos
Catecóis , Depressão , Álcoois Graxos , Lipopolissacarídeos , Microglia , Plasticidade Neuronal , Ratos Sprague-Dawley , Animais , Álcoois Graxos/farmacologia , Microglia/efeitos dos fármacos , Microglia/metabolismo , Ratos , Lipopolissacarídeos/toxicidade , Masculino , Catecóis/farmacologia , Plasticidade Neuronal/efeitos dos fármacos , Depressão/tratamento farmacológico , Depressão/induzido quimicamente , Depressão/metabolismo , Técnicas de Cocultura , Proteína 3 que Contém Domínio de Pirina da Família NLR/metabolismo , Modelos Animais de Doenças , Fármacos Neuroprotetores/farmacologia , Células Cultivadas , Antidepressivos/farmacologia
15.
Food Funct ; 15(11): 6054-6067, 2024 Jun 04.
Artigo em Inglês | MEDLINE | ID: mdl-38753306

RESUMO

6-Gingerol (6-G), an active ingredient of ginger with anti-inflammation and anti-oxidation properties, can treat ulcerative colitis (UC). However, its underlying mechanism is still unclear. In this study, the pharmacodynamic evaluation of 6-G for treating UC was performed, and the mechanism of 6-G in ameliorating UC was excavated by plasma metabolomics and network pharmacology analysis, which was further validated by experimental and molecular docking. The results showed that 6-G could notably reduce diarrhea, weight loss, colonic pathological damage, and inflammation in UC mice. Plasma metabolomic results indicated that 6-G could regulate 19 differential metabolites, and its metabolic pathways mainly involved linoleic acid metabolism and arachidonic acid metabolism, which were closely associated with ferroptosis. Moreover, 60 potential targets for 6-G intervention on ferroptosis in UC were identified by network pharmacology, and enrichment analysis revealed that 6-G suppressed ferroptosis by modulating lipid peroxidation. Besides, the integration of metabolomics and network pharmacology showed that the regulation of 6-G on ferroptosis focused on 3 key targets, including ALOX5, ALOX15, and PTGS2. Further investigation indicated that 6-G significantly inhibited ferroptosis by decreasing iron load and malondialdehyde (MDA), and enhanced antioxidant capacity by reducing the content of glutathione disulfide (GSSG) and increasing the levels of superoxide dismutase (SOD) and glutathione (GSH) in UC mice and RSL3-induced Caco-2 cells. Furthermore, molecular docking showed the high affinity of 6-G with the identified 3 key targets. Collectively, this study elucidated the potential of 6-G in ameliorating UC by inhibiting ferroptosis. The integrated strategy also provided a theoretical basis for 6-G in treating UC.


Assuntos
Catecóis , Colite Ulcerativa , Álcoois Graxos , Ferroptose , Metabolômica , Simulação de Acoplamento Molecular , Farmacologia em Rede , Animais , Ferroptose/efeitos dos fármacos , Camundongos , Álcoois Graxos/farmacologia , Colite Ulcerativa/tratamento farmacológico , Colite Ulcerativa/metabolismo , Catecóis/farmacologia , Masculino , Humanos , Modelos Animais de Doenças , Zingiber officinale/química , Camundongos Endogâmicos C57BL , Células CACO-2
16.
Pestic Biochem Physiol ; 200: 105802, 2024 Mar.
Artigo em Inglês | MEDLINE | ID: mdl-38582605

RESUMO

Aphids are a major problem in agriculture, horticulture, and forestry by feeding on leaves and stems, causing discoloration, leaf curling, yellowing, and stunted growth. Although urushiol, a phenolic compound containing a catechol structure, is known for its antioxidant and anticancer properties, using small molecules to control aphids via catechol-mediated mechanisms is poorly understood. In this study, we investigated the effects of 3-methylcatechol (3-MC) on Myzus persicae fecundity. Our results showed that treatment with 3-MC significantly reduced the intrinsic transcriptional activity of the aphid estrogen-related receptor (MpERR), which regulates the expression of glycolytic genes. Additionally, 3-MC treatment suppressed the promoter activity of MpERR-induced rate-limiting enzymes in glycolysis, such as phosphofructokinase and pyruvate kinase, by inhibiting MpERR binding. Finally, 3-MC also suppressed MpERR-induced glycolytic gene expression and reduced the number of offspring produced by viviparous female aphids. Overall, our findings suggest that 3-MC has the potential to be used as a new strategy for managing aphid populations by controlling their offspring production.


Assuntos
Afídeos , Animais , Afídeos/genética , Catecóis/farmacologia , Expressão Gênica , Estrogênios/farmacologia
17.
J Med Chem ; 67(8): 6705-6725, 2024 Apr 25.
Artigo em Inglês | MEDLINE | ID: mdl-38596897

RESUMO

Cefiderocol is the first approved catechol-conjugated cephalosporin against multidrug-resistant Gram-negative bacteria, while its application was limited by poor chemical stability associated with the pyrrolidinium linker, moderate potency against Klebsiella pneumoniae and Acinetobacter baumannii, intricate procedures for salt preparation, and potential hypersensitivity. To address these issues, a series of novel catechol-conjugated derivatives were designed, synthesized, and evaluated. Extensive structure-activity relationships and structure-metabolism relationships (SMR) were conducted, leading to the discovery of a promising compound 86b (Code no. YFJ-36) with a new thioether linker. 86b exhibited superior and broad-spectrum in vitro antibacterial activity, especially against A. baumannii and K. pneumoniae, compared with cefiderocol. Potent in vivo efficacy was observed in a murine systemic infection model. Furthermore, the physicochemical stability of 86b in fluid medium at pH 6-8 was enhanced. 86b also reduced potential the risk of allergy owing to the quaternary ammonium linker. The improved properties of 86b supported its further research and development.


Assuntos
Antibacterianos , Catecóis , Desenho de Fármacos , Bactérias Gram-Negativas , Testes de Sensibilidade Microbiana , Antibacterianos/farmacologia , Antibacterianos/síntese química , Antibacterianos/química , Catecóis/química , Catecóis/farmacologia , Catecóis/síntese química , Animais , Relação Estrutura-Atividade , Camundongos , Bactérias Gram-Negativas/efeitos dos fármacos , Klebsiella pneumoniae/efeitos dos fármacos , Acinetobacter baumannii/efeitos dos fármacos , beta-Lactamas/farmacologia , beta-Lactamas/síntese química , beta-Lactamas/química , Cefalosporinas/farmacologia , Cefalosporinas/síntese química , Cefalosporinas/química , Descoberta de Drogas
18.
Sci Rep ; 14(1): 7747, 2024 04 02.
Artigo em Inglês | MEDLINE | ID: mdl-38565569

RESUMO

6-Gingerol, the main bioactive compound of ginger, has antioxidant, anti-inflammatory, anti-cancer and neuroprotective effects. However, it is unclear whether 6-Gingerol has protective effects against hepatic ischemia/reperfusion (I/R) injury. In this study, the mouse liver I/R injury model and the mouse AML12 cell hypoxia/reoxygenation (H/R) model were established by pretreatment with 6-Gingerol at different concentrations to explore the potential effects of 6-Gingerol. Serum transaminase levels, liver necrotic area, cell viability, inflammatory response, and cell apoptosis were used to assess the effect of 6-Gingerol on hepatic I/R or cell H/R injury. Quantitative polymerase chain reaction (qPCR) and Western blotting were used to detect the mRNA and protein expression. The results show that 6-Gingerol decreased serum alanine aminotransferase (ALT), aspartate aminotransferase (AST) levels, liver necrosis, inflammatory cytokines IL-1ß, IL-6, MCP-1, TNF-α expression, Ly6g+ inflammatory cell infiltration, protein phosphorylation of NF-κB signaling pathway, Terminal deoxynucleotidyl transferase dUTP nick-end labeling (TUNEL) positive cells, cell apoptosis rate, the protein expression of pro-apoptotic protein BAX and C-Caspase3, increased cell viability, and expression of anti-apoptotic protein BCL-2. Moreover, 6-Gingerol could increase the mRNA and protein expression of mitogen activated protein kinase phosphatase 5 (MKP5) and inhibit the activation of P38/JNK signaling pathway. In MKP5 knockout (KO) mice, the protective effect of 6-gingerol and the inhibition of P38/JNK pathway were significantly weakened. Therefore, our results suggest that 6-Gingerol exerts anti-inflammatory and anti-apoptotic effects to attenuate hepatic I/R injury by regulating the MKP5-mediated P38/JNK signaling pathway.


Assuntos
Catecóis , Álcoois Graxos , Sistema de Sinalização das MAP Quinases , Traumatismo por Reperfusão , Camundongos , Animais , Traumatismo por Reperfusão/tratamento farmacológico , Fígado , Isquemia , Anti-Inflamatórios/farmacologia , Proteínas Reguladoras de Apoptose/farmacologia , Apoptose , RNA Mensageiro/farmacologia
19.
Biosens Bioelectron ; 256: 116275, 2024 Jul 15.
Artigo em Inglês | MEDLINE | ID: mdl-38603839

RESUMO

Constructing relatively inexpensive nanomaterials to simulate the catalytic performance of laccase is of great significance in recent years. Although research on improving laccase-like activity by regulating ligands of copper (amino acids or small organic molecules, etc.) have achieved remarkable success. There are few reports on improving laccase-like activity by adjusting the composition of metal Cu. Here, we used perovskite hydroxide AB(OH)6 as a model to evaluate the relationship between Cu based alloys and their laccase-like activity. We found that when the Cu/Mn alloy ratio of the perovskite hydroxide A point is greater than 1, the laccase-like activity of the binary alloy perovskite hydroxide is higher than that of the corresponding single Cu. Based on the measurements of XPS and ICP-MS, we deduced that the improvements of laccase-like activity mainly attribute to the ratio of Cu+/Cu2+and the content of Cu. Moreover, two types of substrates (toxic pollutants and catechol neurotransmitters) were used to successfully demonstrated such nanozymes' excellent environmental protecting function and biosensing property. This work will provide a novel approach for the construction and application of laccase-like nanozymes in the future.


Assuntos
Técnicas Biossensoriais , Cobre , Lacase , Óxidos , Titânio , Lacase/química , Lacase/metabolismo , Técnicas Biossensoriais/métodos , Cobre/química , Titânio/química , Óxidos/química , Hidróxidos/química , Compostos de Cálcio/química , Recuperação e Remediação Ambiental/métodos , Catecóis/análise , Catecóis/química , Materiais Biomiméticos/química , Catálise
20.
Int J Biol Macromol ; 267(Pt 2): 131662, 2024 May.
Artigo em Inglês | MEDLINE | ID: mdl-38636754

RESUMO

In this study, we investigated detailedly the contribution of catechol in tuning the formation and adhesive properties of coacervates. We have constructed a series of catechol-grafted Chitosan (Chitosan-C), and investigated their coacervation with gum arabic (GA) and the corresponding adhesion. We demonstrate that, increasing catechol grafting ratio from 0 %-44 % impacted the coacervation moderately, while enhanced the adhesion of the coacervate up to 438 % when the catechol faction was 37 %. Further increasing the grafting ratio to 55 % led to precipitated coacervates associated with a declined adhesion. Our findings identify the optimal grafting threshold for coacervation and adhesion, providing insights into the underlying mechanism of coacervate binding. Moreover, the catechol enhancement on adhesion of coacervates tolerates different substrates and diverse polyelectrolyte pairs. The revealed principles shall be helpful for designing adhesive coacervates and boosting their applications in various industrial and biomedical areas.


Assuntos
Catecóis , Quitosana , Quitosana/química , Catecóis/química , Goma Arábica/química , Adesividade , Adesivos/química
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