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1.
Food Chem ; 463(Pt 3): 141279, 2024 Sep 18.
Artículo en Inglés | MEDLINE | ID: mdl-39326317

RESUMEN

Proanthocyanidin (PAC) is recognized as a potent natural antioxidant that prevents various diseases. As societal awareness increases, eco-friendly and efficient natural product extraction technologies are gaining more attention. In this study, an electron beam irradiation (EBI) coupled with ultrasound-assisted natural deep eutectic solvents (NADES) extraction method was developed to enable the green and highly efficient extraction of PAC from walnut green husk (WGH). NADES, prepared with choline chloride and ethylene glycol, demonstrated excellent extraction capacity and storage stability for PAC. Molecular dynamics simulations elucidated the high compatibility between NADES and PAC, attributed mainly to a higher SASA value (207.85 nm2), a greater number of hydrogen bonds (330.99), an extended hydrogen bonding lifetime (4.54 ps), and lower inter-molecular interaction energy. Based on these findings, the optimal conditions (13 kGy EBI, 42 mL/g liquid-solid ratio, 38 °C extraction temperature, 70 min extraction time) resulted in a maximum PAC extraction yield of 56.34 mg/g. Notably, this yield was 32.93 % higher than that observed in samples not treated with EBI and ultrasound-assisted extraction (UAE). Analysis of tissue morphology, extract functional groups and thermal behavior suggested a possible mechanism for the synergistically enhanced PAC extraction by the EBI-NADES-UAE method. Additionally, the PAC extracted using the NADES by the EBI coupled with ultrasound-assisted method exhibited outstanding antioxidant activity (comparable to Vc), digestive enzyme inhibition (IC50: 17-0.61 mg/mL), and anti-glycation capacity (IC50: 86.49 µg/mL). Overall, this work provided a green and efficient strategy for PAC extraction from WGH, elucidated the extraction mechanism and bioactivities, and offered valuable insights for potential industrial applications.

2.
Int J Biol Macromol ; 279(Pt 2): 135198, 2024 Aug 30.
Artículo en Inglés | MEDLINE | ID: mdl-39216575

RESUMEN

The effects of electron beam irradiation (EBI) pretreatment on the alkaline extraction of pectic polysaccharides from Diaphragma juglandis fructus (DJF) are highly dependent on the irradiation dosage. Comprehensive characterizations encompassing physicochemical, structural, and functional properties were conducted on crude pectic polysaccharide extract from DJF subjected to various EBI doses. EBI pretreatment significantly increased the yields of crude pectic polysaccharides extract (increasing by 41.89 %), also facilitating the extraction of uronic acid, RG-I structure, and protein content, despite causing a decrease in total sugar content. EBI pretreatment induced the degradation of pectin, resulting in decreased molecular weight, particle size, crystallinity, viscosity, thermal stability, and water holding capacity, while enhancing solubility and oil holding capacity. Variations in physicochemical and structural properties induced by different EBI doses influenced the functional activities of DJF pectic polysaccharides. Low-dose EBI (at 5 kGy) pretreatment markedly improved the emulsifying activity/stability (increasing by 20.82/74.10 %) and ABTS/DPPH radical scavenging activity (increasing by 27.91/12.40 %), whereas high-dose EBI pretreatment (50 kGy) greatly enhanced foaming capacity/stability (increasing by 259.99/175.56 %). These findings provide a novel regulatory strategy for the functional activity of pectic polysaccharides.

3.
J Food Sci ; 89(1): 121-134, 2024 Jan.
Artículo en Inglés | MEDLINE | ID: mdl-38010731

RESUMEN

This study aimed to optimize the temperature adaptive conditions of pulsed vacuum drying (PVD) for green walnut husk (GWH) to tackle the issues of severe environmental pollution and limited utilization of GWH. The results of the single-factor experiment revealed that the optimal drying temperature for PVD of GWH was 65°C, with a pulsed ratio of 9 min: 3 min. The drying time decreased from 10.87 to 6.32 h with increasing drying temperature and from 8.83 to 6.23 kW·h/kg with increasing pulsed ratio. Energy consumption also decreased with shorter drying time and shorter vacuum time. Under this optimal variable temperature drying condition, GWH exhibited the highest total active substance content, with respective values of 9.43 mg/g for total triterpenes, 35.68 mg/g for flavonoids, 9.51 mg/g for polyphenols, and 9.55 mg/g for quinones. The experimental drying data of GWH were best fitted by a logarithmic model, with R2 values ranging from 0.9927 to 0.9943. Furthermore, the observed microstructure of GWH corresponded to the variations in total active substance content. This study provided valuable theoretical guidance for addressing environmental pollution associated with GWH and facilitating the industrialization and refinement of GWH drying processes. PRACTICAL APPLICATION: There is a growing interest in harnessing the potential value of agricultural waste to transform low-cost raw materials into high-value products while mitigating environmental pollution. In this study, for the first time, the effects of variable temperature pulsed vacuum drying on the content of active substances, drying time, and energy consumption of green walnut husk (GWH) were investigated. The findings serve as a theoretical foundation for addressing environmental pollution issues associated with GWH and enabling the industrialization and precision drying of GWH.


Asunto(s)
Juglans , Vacio , Temperatura , Desecación/métodos , Polifenoles/análisis
4.
J Food Sci ; 88(3): 1060-1074, 2023 Mar.
Artículo en Inglés | MEDLINE | ID: mdl-36695779

RESUMEN

Walnut green husk (WGH) is rich in natural compounds and is valued as a potential source of antioxidant and antimicrobial properties. In this study, the antioxidant and antimicrobial activities of petroleum ether polar fraction, dichloromethane polar fraction, ethyl acetate polar fraction (EAPF), and n-butanol polar fraction from WGH were analyzed. The results showed that EAPF exhibited the highest total flavonoid content (65.74 ± 1.01 mg rutin equivalents [RE]/g dry weight [DW]) and total phenol content (48.73 ± 1.09 mg gallic acid equivalent [GAE]/g DW), with the highest 2,2-diphenyl-1-picrylhydrazyl, hydroxyl radical (•OH), and 2,2-azino-bis-3-ethylbenzothiazoline-6-sulfonate scavenging activity compared with other fractions. EAPF also showed good antibacterial activity against Escherichia coli and Bacillus cereus vegetative cells, with a diameter of inhibition zones of 33.5 and 37.6 mm, respectively, a minimum inhibitory concentration of 31.25 mg/ml and a minimum bactericidal concentration of 62.5 mg/ml, which inhibited the growth of both bacteria. Analysis of the antibacterial mechanism demonstrated that EAPF damaged the integrity of the cell membrane, increased the membrane permeability, and triggered the leakage of intracellular material. In addition, ultrahigh performance liquid chromatography-tandem with mass spectrometry analysis revealed that 8 polyphenols and 14 flavonoids were mainly present in EAPF, such as chlorogenic acid (C16 H18 O9 ), gallic acid (C7 H6 O5 ), vanillic acid (C8 H8 O4 ), ferulic acid (C10 H10 O4 ), epicatechin (C15 H14 O6 ), catechin (C15 H14 O6 ), hesperetin (C16 H14 O6 ), naringenin (C15 H12 O5 ), hyperin (C21 H20 O12 ), luteolin (C15 H10 O6 ), and so on. Therefore, WGH had the potential to be developed as a natural antioxidant and antibacterial material. PRACTICAL APPLICATION: Our work indicates that WGH contains abundant flavonoids and polyphenols compounds. Therefore, the plant byproducts like WGH may have a promising application as a source of antimicrobial and antioxidant additives.


Asunto(s)
Antiinfecciosos , Juglans , Antioxidantes/química , Extractos Vegetales/farmacología , Extractos Vegetales/química , Antiinfecciosos/farmacología , Flavonoides/análisis , Antibacterianos/farmacología , Antibacterianos/análisis , Polifenoles , Ácido Gálico/farmacología
5.
Spectrochim Acta A Mol Biomol Spectrosc ; 285: 121797, 2023 Jan 15.
Artículo en Inglés | MEDLINE | ID: mdl-36115306

RESUMEN

Inhibiting the activity of α-amylase has been considered an effective strategy to manage hyperglycemia. Hyperoside and quercetin are the main natural flavonoids in various plants, and the inhibition mechanism on α-amylase remains unclear. In this study, the structure-activity relationships between hyperoside/quercetin and α-amylase were evaluated by enzyme kinetic analysis, multi-spectroscopic techniques, and molecular docking analysis. Results showed that hyperoside and quercetin exhibited significant α-amylase inhibitory activities with IC50 values of 0.491 and 0.325 mg/mL, respectively. The α-amylase activity decreased in the presence of hyperoside and quercetin in a competitive and noncompetitive manner, respectively. UV-vis spectra suggested that the aromatic amino acid residues (Trp and Tyr) microenvironment of α-amylase changed in the presence of these two flavonoids. FTIR and CD spectra showed the vibrations of the amide bands and the secondary structure content changes. The fluorescence quenching mechanism of α-amylase by hyperoside and quercetin belonged to the static quenching type. Finally, molecular docking intuitively showed that hyperoside/quercetin formed hydrogen bonds with the key active site residues (Asp197, Glu233, and Asp300) in α-amylase. MD simulation indicated hyperoside/quercetin-α-amylase docked complexes had good stability. Taken together, this research provides new sights to developing potent drugs or functional foods with hyperoside and quercetin, offering new avenues for hyperglycemia treatment.


Asunto(s)
Hiperglucemia , alfa-Amilasas , Humanos , alfa-Amilasas/metabolismo , Simulación del Acoplamiento Molecular , Quercetina/química , Cinética , Flavonoides/química , Relación Estructura-Actividad , Análisis Espectral
6.
Molecules ; 27(21)2022 Oct 28.
Artículo en Inglés | MEDLINE | ID: mdl-36364167

RESUMEN

Antibacterial hand sanitizers could play a prominent role in slowing down the spread and infection of hand bacterial pathogens; luteolin (LUT) is potentially useful as an antibacterial component. Therefore, this study elucidated the antibacterial mechanism of LUT against Escherichia coli (E. coli) and Staphylococcus aureus (S. aureus) and developed an antibacterial hand sanitizer. The results showed that LUT had excellent antibacterial activity against both E. coli (minimum inhibitory concentration (MIC) = 312.5 µg/mL, minimal bactericidal concentration (MBC) = 625 µg/mL), and S. aureus (MIC = 312.5 µg/mL, MBC = 625 µg/mL). Furthermore, LUT induced cell dysfunction in E. coli and S. aureus, changed membrane permeability, and promoted the leakage of cellular contents. Confocal laser scanning microscopy (CLSM) and scanning electron microscopy (SEM) analysis showed that LUT treatment affected cell structure and disrupted cell membrane integrity. The Fourier transform infrared analysis (FTIR) also confirmed that the LUT acted on the cell membranes of both E. coli and S. aureus. Overall, the application of LUT in hand sanitizer had better inhibition effects. Therefore, this study could provide insight into expanding the application of LUT in the hand sanitizer markets.


Asunto(s)
Desinfectantes para las Manos , Staphylococcus aureus , Escherichia coli , Desinfectantes para las Manos/farmacología , Luteolina/farmacología , Pruebas de Sensibilidad Microbiana , Antibacterianos/farmacología , Antibacterianos/química
7.
Foods ; 11(17)2022 Aug 24.
Artículo en Inglés | MEDLINE | ID: mdl-36076744

RESUMEN

Foodborne disease caused by Listeria monocytogenes is a major global food safety problem. A potential solution is the antimicrobial development of the highly bioactive natural product juglone, yet few studies exist on its antibacterial mechanism against L. monocytogenes. Thus, we aimed to elucidate the antibacterial mechanism of action of juglone against L. monocytogenes by determining the resultant cell morphology, membrane permeability, membrane integrity, and proteome changes. The minimum inhibitory concentration of juglone against L. monocytogenes was 50 µg/mL, and L. monocytogenes treated with juglone had longer lag phases compared to controls. Juglone induced L. monocytogenes cell dysfunction, leakage of potassium ions, and membrane potential hyperpolarization. Confocal laser scanning microscopy and field-emission-gun scanning electron microscope assays revealed clear membrane damage due to juglone treatment. Fourier transform infrared analyses showed that L. monocytogenes responded to juglone by some conformational and compositional changes in the molecular makeup of the cell membrane. Sodium dodecyl sulfate-polyacrylamide gel electrophoresis analysis showed that juglone either destroyed proteins or inhibited proteins synthesis in L. monocytogenes. Therefore, our findings established juglone as a natural antibacterial agent with potential to control foodborne L. monocytogenes infections.

8.
Food Chem ; 373(Pt B): 131520, 2022 Mar 30.
Artículo en Inglés | MEDLINE | ID: mdl-34753662

RESUMEN

Green walnut husk (GWH) contains abundant active compounds and is valued as a potential source of natural antioxidants. This study aimed at assessing the impact of electron beam irradiation (EBI) pretreatment on the extraction yield and antioxidant activity of active compounds in GWH. The ultrasonic extraction of active substances was optimized by response surface method (RSM). Scanning electron microscopy, Fourier-transform infrared spectroscopy, and X-ray diffraction revealed physical structure changes in GWH powder. After EBI pretreatment, the content of polyphenols, flavonoids, and triterpenes in GWH increased by 18.88%, 43.00%, and 11.08%, respectively. Irradiation doses up to 30 kGy, DPPH, OH, and ABTS radical scavenging activity and reducing power of the crude extract were enhanced by 9.56%, 15.62%, 15.60%, and 36.98%, respectively. This was significantly different (P < 0.05) than the non-irradiated GWH. Therefore, EBI is a new pretreatment technology with potential application in the extraction and utilization of GWH.


Asunto(s)
Antioxidantes , Juglans , Electrones , Flavonoides , Extractos Vegetales , Polifenoles
9.
Chemistry ; 26(49): 11199-11208, 2020 Sep 01.
Artículo en Inglés | MEDLINE | ID: mdl-32227410

RESUMEN

Liquid crystalline block copolymers (LCBCPs) are promising for developing functional materials owing to an assembly of better functionalities. Taking advantage of differences in reactivity between alkynyl and vinyl over temperature during hydrosilylation, a series of LCBCPs with modular functionalization of the block copolymers (BCPs) are reported by independently and site-selectively attaching azobenzene moieties containing alkynyl (LC1 ) and Si-H (LC2 ) terminals into well-designed poly(styrene)-block-polybutadienes (PS-b-PBs) and poly(4-vinylphenyldimethylsilane)-block-polybutadienes (PVPDMS-b-PBs) produced from living anionic polymerization (LAP). By the principle of modular functionalization, it is demonstrated that mono-functionalized (PVPDMS-g-LC1 )-b-PB and PS-b-(PB-g-LC2 ) not only maintain independence but also have cooperative contributions to bi-functionalized (PVPDMS-g-LC1 )-b-(PB-g-LC2 ) in terms of mesomorphic performances and microphase separation, which is evident from differential scanning calorimetry (DSC) and polarized optical morphologies (POM) and identified by powder X-ray diffractions. With the application of the new principle of modular functionalization, local-crosslinked liquid crystalline networks (LCNs) with controlled functionality are successfully synthesized, which show well-controlled phase behaviors over molecular compositions.

10.
Angew Chem Int Ed Engl ; 57(50): 16538-16543, 2018 12 10.
Artículo en Inglés | MEDLINE | ID: mdl-30362659

RESUMEN

Reported is an intriguing advance in living anionic polymerization (LAP) by a "locked-unlocked" mechanism in which the living anionic species can be quantitatively locked by end-capping with 1-(tri-isopropoxymethylsilylphenyl)-1-phenylethylene (DPE-Si(O-iPr)3 ) and can be unlocked by adding the key, sodium 2,3-dimethylpentan-3-olate (NaODP). These new insights into this mechanism were carefully confirmed by designing reactions involving sequential feeding of quantitative DPE-Si(O-iPr)3 and traditional monomers mixed with NaODP, and subsequently characterizing the corresponding samples, taken during the feeding process, by GPC, NMR, and MALDI-TOF-MS techniques. The switch from the locked to unlocked state was clearly confirmed by these characterization techniques. The putative locked-unlocked mechanism in the LAP was simulated by the Gaussian method. This intriguing mechanistic finding of LAP reactions is expected to supplement the existing knowledge and facilitate the tailoring of specific structures for these polymerizations.


Asunto(s)
Aniones/química , Pentanos/química , Polimerizacion , Silanos/química , Estireno/química , Espectroscopía de Resonancia Magnética , Modelos Moleculares , Espectrometría de Masa por Láser de Matriz Asistida de Ionización Desorción
11.
Macromol Rapid Commun ; 38(18)2017 Sep.
Artículo en Inglés | MEDLINE | ID: mdl-28759143

RESUMEN

By combining living anionic polymerization and the highly efficient Ugi four-component reaction (Ugi-4CR), in-chain, multicomponent, functionalized polymers are facilely synthesized with efficient conversation and abundant functionality. l-[4-[N,N-Bis(trimethylsilyl)-amino]phenyl]-l-phenylethylene, which is redefined as Ugi-DPE, is anionically copolymerized to synthesize the well-defined in-chain, multi-amino functionalized polystyrene (P(St/DPE-NH2 )), the backbone for the Ugi-4CR, via hydrolysis of the copolymerization (P(St/Ugi-DPE)). Subsequently, several functionalized components are facilely clicked onto P(St/DPE-NH2 ) to investigate the model reactions of the in-chain, multicomponent functionalization via the Ugi-4CR. In contrast to conventional postpolymerization modifications, this approach proceeds under mild reaction conditions without the use of a catalyst and meanwhile an efficient conversation is obtained. Finally, the modified experimental results investigated in this research show the promising potential of the combination of well-defined amino functionalized polymers and Ugi-4CR in the field of multicomponent, functionalized postpolymerization modification.


Asunto(s)
Aniones/química , Polímeros/síntesis química , Polimerizacion
12.
Polymers (Basel) ; 9(5)2017 May 11.
Artículo en Inglés | MEDLINE | ID: mdl-30970850

RESUMEN

A 1,1-diphenylethylene (DPE) derivative with an alkoxysilyl group (DPE-SiOEt) was synthesized. It was end-capped with poly(styryl)lithium (PSLi) and then copolymerized with styrene via living anionic polymerization (LAP) in a non-polar solvent at room temperature. The observed side coupling reaction was carefully investigated by end-capping the polymer. Changes in molecular weight support the plausibility of a mechanism involving living anionic species (PSLi or lithiated DPE-end-capped polystyrene, PSDLi) and the alkoxysilyl groups. Through a series of copolymerizations with different feed ratios, the kinetics of the side coupling reaction were also studied. The results showed that the side reactions could be controlled using an excess feed of DPE-SiOEt, a potentially useful strategy for the synthesis and application of well-defined alkoxysilyl-functionalized polymers via LAP.

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