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1.
Int J Biol Macromol ; 280(Pt 1): 135631, 2024 Sep 14.
Artigo em Inglês | MEDLINE | ID: mdl-39284471

RESUMO

Exploring tyrosinase inhibitors has been an effective way to find promising anti-browning agents in the food industry. Therefore, a class of thiosemicarbazide derivatives (4a-4m) were synthesized and we investigated the inhibitory mechanism on tyrosinase by fluorescence quenching, copper ion chelating and UV spectra study etc. 2-(2-Chlorobenzyl) hydrazine-1-carbothioamide (4f) (IC50 = 1.21 ± 0.02 µM) is the most active compound of all derivatives, which was defined as a mix-type inhibitor. Additionally, molecular docking and copper ions chelating studies indicated that compound 4f has the ability to inhibit the tyrosinase activity by chelating the copper ions in the active region. Furthermore, compound 4f also exhibited lower cytotoxicity, excellent aqueous solubility and outstanding anti-browning capacity in fresh apple juice. These findings indicated these derivatives could provide more possibility for developing more safer and effective anti-browning agents.

2.
Food Chem ; 460(Pt 3): 140722, 2024 Dec 01.
Artigo em Inglês | MEDLINE | ID: mdl-39106753

RESUMO

Tyrosinase (Polyphenol oxidase), a key enzyme in enzymatic browning, is an attractive target for developing new anti-browning agents in the food industry. In this work, twenty pyrazole-1,2,4-triazole derivatives (3a-3n, 4a-4f) were synthesized and tested in vitro, most of compounds showed potent anti-tyrosinase activity. Of these, 3c (IC50 = 1.02 ± 0.08 µM) was found to be 14 folds stronger than kojic acid (IC50 = 14.74 ± 1.23 µM) and behaved as a mixed type inhibitor. Besides, the disappeared peak of dopaquinone in the HPLC assay intuitively validated the inhibitory effect of 3c. Copper ions chelating, fluorescence quenching and molecular docking assays showed that coordination with copper is the key to play a role. Furthermore, 3c exhibited excellent anti-browning ability for the Rosa roxburghii Tratt, the non-enzymatic browning experiment showed that 3c could prevent browning in non-enzymatic ways. It is suggested that these derivatives could serve as the leading compounds to find more efficient anti-browning agents in the future.


Assuntos
Inibidores Enzimáticos , Simulação de Acoplamento Molecular , Monofenol Mono-Oxigenase , Pirazóis , Triazóis , Monofenol Mono-Oxigenase/antagonistas & inibidores , Monofenol Mono-Oxigenase/química , Triazóis/química , Triazóis/farmacologia , Inibidores Enzimáticos/química , Inibidores Enzimáticos/farmacologia , Pirazóis/química , Pirazóis/farmacologia , Relação Estrutura-Atividade , Desenho de Fármacos , Proteínas Fúngicas/química , Proteínas Fúngicas/antagonistas & inibidores , Estrutura Molecular , Reação de Maillard
3.
Int J Biol Macromol ; 278(Pt 1): 134611, 2024 Oct.
Artigo em Inglês | MEDLINE | ID: mdl-39127278

RESUMO

Deep eutectic solvent (DES) has been recognized as a promising plasticizer for the preparation of biodegradable food packaging films. In addition, DES-plasticized chitosan (CS) films could also serve as a favorable carrier for loading active components. In this work, a ternary composite film was fabricated by plasticizing chitosan with DES and the active ingredient proanthocyanidin (PA) was used as a cross-linking agent. The incorporation of PAs significantly enhanced the toughness, elasticity, and hydrophobicity of the ternary CS-DES-PA composite films. It achieved antioxidant and bacteriostatic functions. In particular, the ternary CS-DES-PA composite films had a thickness of 0.16 ± 0.01 µm, a tensile strength of 2.63 ± 0.48 MPa, and an elongation about 73.22 %. They also have improved water resistance, UV blocking, with a high-water contact angle of 88.4° and a low water swelling of 5 % on the surface of the film. Meanwhile, the PAs in the film could slow down the browning of litchi fruits. This ternary blended film (CS-DES-PA) achieves better compatibility of the active ingredient in the film-forming substrate. It also provides a green and biodegradable packaging material for food packaging.


Assuntos
Quitosana , Embalagem de Alimentos , Proantocianidinas , Quitosana/química , Proantocianidinas/química , Embalagem de Alimentos/métodos , Solventes Eutéticos Profundos/química , Antioxidantes/química , Antioxidantes/farmacologia , Fenômenos Químicos , Interações Hidrofóbicas e Hidrofílicas , Resistência à Tração , Antibacterianos/química , Antibacterianos/farmacologia , Água/química
4.
Food Chem ; 461: 140823, 2024 Dec 15.
Artigo em Inglês | MEDLINE | ID: mdl-39153374

RESUMO

Salicylic acid is a commonly used anti-spoilage agent to prevent browning and quality degradation during potato processing, yet its precise mechanism remains unclear. This study elucidates the role of StuPPO2, a functional protein in Favorita potato shreds, in relation to the anti-browning and starch degradation effects of 52 SA analogues. By employing molecular docking and Gaussian computing, SA localizes within the hydrophobic cavity of StuPPO2, facilitated by hydroxyl and carboxyl groups. The inhibitory effect depends on the distribution pattern of the maximal electrostatic surface potential, requiring hydroxyl ion potentials of >56 kcal/mol and carboxyl ion potentials of >42 kcal/mol, respectively. Multiomics analysis, corroborated by validation tests, indicates that SA synthetically suppresses activities linked to defense response, root regeneration, starch degradation, glycoalkaloids metabolism, and potato shred discoloration, thereby preserving quality. Furthermore, SA enhances antimicrobial and insect-repellent aromas, thereby countering biotic threats in potato shreds. These collective mechanisms underscore SA's anti-spoilage properties, offering theoretical foundations and potential new anti-browning agents for agricultural preservatives.


Assuntos
Ácido Salicílico , Solanum tuberosum , Solanum tuberosum/química , Solanum tuberosum/metabolismo , Ácido Salicílico/química , Ácido Salicílico/farmacologia , Proteínas de Plantas/química , Proteínas de Plantas/metabolismo , Simulação de Acoplamento Molecular , Tubérculos/química , Conservantes de Alimentos/farmacologia , Conservantes de Alimentos/química , Manipulação de Alimentos , Conservação de Alimentos/métodos
5.
Zhongguo Zhong Yao Za Zhi ; 49(11): 2930-2939, 2024 Jun.
Artigo em Chinês | MEDLINE | ID: mdl-39041152

RESUMO

To investigate the effects of different initial processing methods on the quality of Fritillaria taipaiensis, this study explored the effects of anti-browning treatment, drying methods, and drying temperatures on the commercial characters, chromaticity values, and alkaloid and nucleoside components of Fritillariae Taipaiensis Bulbus. The results were comprehensively evaluated through correlation analysis(CA), principal component analysis(PCA), and hierarchical clustering analysis(HCA). Compared with those of the direct drying group(WD60), the chromaticity values(ΔE*) of the groups with scraped outer skin( FHB1) and mixed lime powder treatments(FHB2) were significantly reduced, indicating the inhibition of the browning process. The total alkaloid content of the group with mixed raw soil treatment(FHB3) and the FHB2 group showed no significant change, whereas that of the group with 5%Na Cl O solution rinse treatment(FHB4) was the lowest. Compared with air-blast dried(WD50) samples, the ΔE* values of freezedried(FS6) and vacuum-dried(FS5) samples were significantly decreased, with an increase in total alkaloid contents. Conversely,the ΔE* values of shade-dried(FS1) and sun-dried(FS2) samples were significantly increased, with severe browning and low total alkaloid contents. The total alkaloid contents of heat-pump-dried(FS4) samples showed no significant change, and their ΔE* value was significantly decreased, with a light degree of browning and favorable commercial characters. The total alkaloid content of air-blast dried samples initially increased and then decreased within the range of 40-80 ℃, and the highest content was recorded at 70 ℃. The ΔE* values of high-temperature air-blast dried samples(70-80 ℃) were smaller with a light degree of browning, whereas their texture was compact and lacked powder. CA revealed a significant relationship between the uracil content and chromaticity value of the samples(P< 0. 05). The clustering relationships among samples subjected to different treatments were visualized via PCA and HCA. The results showed that FHB2 and air-blast drying(50-60 ℃) were more suitable for large-scale production, and heat pump drying could be a promising direction for future development. This study provides a scientific basis for optimizing the initial processing methods of Fritillaria taipaiensis.


Assuntos
Alcaloides , Medicamentos de Ervas Chinesas , Fritillaria , Fritillaria/química , Alcaloides/análise , Alcaloides/química , Medicamentos de Ervas Chinesas/química , Medicamentos de Ervas Chinesas/análise , Análise de Componente Principal , Dessecação/métodos
6.
Int J Biol Macromol ; 275(Pt 2): 133669, 2024 Aug.
Artigo em Inglês | MEDLINE | ID: mdl-38971289

RESUMO

Surface browning of plant-derived fresh-cut products is mainly caused by conversion of the phenolic compounds into o-quinones under tyrosinase catalysis. In this study, the rarely reported complex tannins from Euryale ferox seed shell (ECTs) constituted by the units of 35.60% condensed tannins and 64.40% hydrolysable tannins were shown to suppress the activity of tyrosinase efficiently, supporting the exploitation of ECTs into novel anti-browning agents. However, the utilization of ECTs in food preservation is often restricted because of their chemical instability to external environment. Further fabrication of nanoliposomes loaded with ECTs (ECTs-NLs) herein was carried out to improve the stability of ECTs. DLS, TEM, FTIR, DSC and XRD confirmed that ECTs were encapsulated into nanoliposomes successfully, and ECTs-NLs appeared as vesicle-like spherical morphology with favorable encapsulation efficiency, uniform particle size distribution and negative zeta-potential. The resulting ECTs-NLs were relatively stable in the dark at 4 °C. Nanoliposomal encapsulation significantly enhanced ECTs stability, thus protecting inhibitory effect of ECTs against tyrosinase. Furthermore, anti-browning evaluation proved that ECTs-NLs had distinct advantages over free ECTs in alleviating surface browning of fresh-cut asparagus lettuces. These results suggested that nanoliposomes were effective in stabilizing ECTs and ECTs-NLs could be potentially applied to the fresh-cut food industry.


Assuntos
Asparagus , Lipossomos , Monofenol Mono-Oxigenase , Sementes , Taninos , Lipossomos/química , Sementes/química , Asparagus/química , Taninos/química , Monofenol Mono-Oxigenase/antagonistas & inibidores , Nanopartículas/química , Tamanho da Partícula , Nymphaeaceae/química
7.
Int J Biol Macromol ; 269(Pt 1): 132051, 2024 Jun.
Artigo em Inglês | MEDLINE | ID: mdl-38777687

RESUMO

The impact of guar gum (GG), crude algae ethanolic extract (CAEE), and turmeric essential oil (TEO) incorporated edible coating formulations on the quality of cut potatoes was investigated at room temperature (27 ±â€¯3 °C, 70-85 % RH) storage using a rotatable central composite design. Besides, 30 % glycerol, 5 % calcium chloride, and 3 % ascorbic acid (w/w) were added to the coating solution as additives. The surface color, respiration rate, water vapor transmission rate, visible mold growth, and sensory analysis were assessed after seven days of storage. The inclusion of ascorbic acid and TEO in edible coating demonstrated a more effective delay in browning. The coated potatoes had lower OTR, CTR, and WVTR values for GG concentrations of 0.5 to 1 g/100 mL than the control. Compared to additives, higher concentrations of GG improved response parameters. The WVTR value of coated potatoes was significantly impacted by the interaction between CAEE and TEO with GG. Incorporating CAEE and TEO into the formulations of guar gum led to a reduction in the permeability of the coating to oxygen and water vapor. The seven days of extended shelf life compared to two days of control were observed with the optimized coating formulation. Furthermore, the application of the coating treatment proved effective in preventing enzymatic browning and creating a barrier against moisture and gases, contributing to prolonged freshness during extended storage periods.


Assuntos
Armazenamento de Alimentos , Galactanos , Mananas , Gomas Vegetais , Solanum tuberosum , Gomas Vegetais/química , Galactanos/química , Mananas/química , Mananas/farmacologia , Solanum tuberosum/química , Armazenamento de Alimentos/métodos , Conservação de Alimentos/métodos
8.
Food Chem ; 452: 139424, 2024 Sep 15.
Artigo em Inglês | MEDLINE | ID: mdl-38754167

RESUMO

This study explores the influence of incorporating L-cysteine (L-Cys), chitosan (CTS), and citric acid (CA) on the enzymatic modification of potato starch (EPS) films to enhance anti-browning properties. Four types of EPS composite films were evaluated for preserving fresh-cut potato slices at low temperatures to inhibit browning. Their thermal, physiochemical, mechanical, and digestibility properties were assessed. Results indicate that the addition of CTS, CA, and L-Cys improved the anti-browning activity of the EPS films by increasing film thickness and reducing water vapor permeability (WVP), oxygen transmission rate (OTR), ultraviolet (UV) transmittance, and tensile strength (TS). Furthermore, these additives improved the film's microstructure, resulting in reinforced intermolecular interactions, increased elongation at break, heightened crystallinity, enhanced thermal stability, and favorable gastrointestinal digestibility. Overall, EPS/CTS/L-Cys/CA composite films show promise as edible packaging materials with effective anti-browning properties.


Assuntos
Quitosana , Ácido Cítrico , Cisteína , Solanum tuberosum , Amido , Solanum tuberosum/química , Quitosana/química , Amido/química , Ácido Cítrico/química , Cisteína/química , Resistência à Tração , Embalagem de Alimentos/instrumentação , Permeabilidade
9.
Food Chem X ; 21: 101128, 2024 Mar 30.
Artigo em Inglês | MEDLINE | ID: mdl-38292671

RESUMO

Thirteen kojic acid-coumarin derivatives were synthesized using the principle of molecular hybridization, and their structures were characterized by 1H NMR, 13C NMR, and HRMS. In vitro enzyme inhibition experiments showed that all newly synthesized derivatives have excellent inhibition of tyrosinase (TYR) activity. As a mixed inhibitor, compound 6f has the strongest activity, with an IC50 value of 0.88 ± 0.10 µM. Multispectral experiments have confirmed that the mode of action of compound 6f on TYR was static quenching. In addition, compound 6f formed a new complex with TYR, which increased the hydrophobicity of the enzyme microenvironment, reduced the content of the α-helix in the enzyme, and changed the secondary structure. The experimental results showed that compound 6f effectively inhibited the browning of lotus root slices and had low cytotoxicity. Therefore, compound 6f is believed to have great development potential as a TYR inhibitor in the food industry.

10.
Foods ; 13(1)2024 Jan 03.
Artigo em Inglês | MEDLINE | ID: mdl-38201195

RESUMO

Browning and other undesirable effects on Agaricus bisporus (A. bisporus) during storage seriously affect its commercial value. In this study, a strain, Lactiplantibacillus plantarum NML21, that resists browning and delays the deterioration of A. bisporus was screened among 72 strains of lactic acid bacteria (LAB), and its preservative effect was analyzed. The results demonstrated that gallic acid, catechin, and protocatechuic acid promoted the growth of NML21, and the strain conversion rates of gallic acid and protocatechuic acid reached 97.16% and 95.85%, respectively. During a 15 d storage of the samples, the NML21 treatment displayed a reduction in the browning index (58.4), weight loss (2.64%), respiration rate (325.45 mg kg-1 h-1), and firmness (0.65 N). The treatment further inhibited Pseudomonas spp. growth and polyphenol oxidase activity, improved the antioxidant capacity, reduced the accumulation of reactive oxygen species, and reduced the malonaldehyde content and cell membrane conductivity. Taken together, the optimized concentrations of NML21 may extend the shelf life of A. bisporus for 3-6 d and could be a useful technique for preserving fresh produce.

11.
Food Chem ; 442: 138430, 2024 Jun 01.
Artigo em Inglês | MEDLINE | ID: mdl-38241986

RESUMO

The tyrosinase pathway takes part in the enzymatic process of food browning and is primarily responsible for food spoilage - manifesting itself from a decrease in its nutritional value to a deterioration of taste, which consequently leads to a gradual loss of shelf life. Finding safe and bio-based tyrosinase inhibitors and anti-browning agents may be of great importance in agriculture and food industries. Herein, we showed that Cyrene™ exhibits tyrosinase inhibitory activity (IC50: 268.2 µM), the 1.44 times higher than ascorbic acid (IC50: 386.5 µM). Binding mode studies demonstrated that the carbonyl oxygen of Cyrene™ coordinates with both copper ions. Surprisingly, both hydroxyl groups of Cyrene gem-diol perform a monodentate binding mode with both copper ions, at similar distances. This fact suggests that both compounds could have a similar binding mode and, as consequence, similar biological activities in tyrosinase inhibition assays and anti-browning activities.


Assuntos
Cobre , Monofenol Mono-Oxigenase , Reação de Maillard , Íons , Inibidores Enzimáticos/farmacologia , Simulação de Acoplamento Molecular
12.
Int J Biol Macromol ; 258(Pt 1): 128951, 2024 Feb.
Artigo em Inglês | MEDLINE | ID: mdl-38143054

RESUMO

In this study, the biosynthesis of phycocyanin ß-subunit (CpcB) in Escherichia coli BL21 was investigated, and its antioxidant activity and application in anti-browning of fresh-cut apples was explored. Four genes (cpcB, cpeS, hox1 and pcyA) involved in the biosynthesis of CpcB were cloned and transformed into E. coli BL21 by constructing recombinant plasmid pETDuet-5. The positive transformant was screened by ampicillin resistance. The analysis of SDS-PAGE and zinc fluorescence spectrum showed that CpcB was successfully expressed in E. coli BL21 with a molecular weight of 21 kDa. The purified CpcB had a maximum absorption peak at 615 nm, and its maximum florescence emission wavelength was 640 nm. It exhibited a stronger ability to scavenge four free radicals than Vc. The color change in fresh-cut apples was obviously delayed by the CpcB treatment. These results suggest that CpcB may be used as a potential anti-browning agent for food preservation.


Assuntos
Antioxidantes , Malus , Ficocianina , Escherichia coli/genética , Plasmídeos
13.
J Food Sci ; 88(12): 5026-5043, 2023 Dec.
Artigo em Inglês | MEDLINE | ID: mdl-37872831

RESUMO

In this study, a comprehensive approach to advance the inhibitory effect of Hibiscus sabdariffa extract on apple polyphenol oxidase (PPO) was performed. PPO was extracted, purified, and characterized for optimal activity, whereas response surface methodology generated a quadratic polynomial model to fit the experimental results for hibiscus extraction. The optimum conditions allowed to predict a maximum recovery of anthocyanins (256.11 mg delphinidin-3-O-glucoside/g), with a validated value of 272.87 mg delphinidin-3-O-glucoside/g dry weight (DW). The chromatographic methods highlighted the presence of gallic acid (36,812.90 µg/g DW extract), myricetin (141,933.84 µg/g DW extract), caffeic acid (101,394.07 µg/g DW extract), sinapic acid (1157.46 µg/g DW extract), kaempferol (2136.76 µg/g DW extract), and delphinidin 3-O-ß-d-glucoside (226,367.08 µg/g DW extract). The inactivation of PPO followed a first-order kinetic model. A temperature-mediated flexible fit between PPO and anthocyanins was suggested, whereas the molecular docking tests indicated that PPO is a good receptor for cafestol, gallic acid, and catechin, involving hydrophobic and hydrogen bond interactions. PRACTICAL APPLICATION: It is well known that enzymatic browning is one of the most important challenges in the industrial minimal processing of selected fruit and vegetable products. Novel inhibitors for polyphenol oxidase are proposed in this study by using an anthocyanin-enriched extract from Hibiscus sabdariffa L. Based on our results, combining the chemical effect of phytochemicals from hibiscus extract with different functional groups with minimal heating could be an interesting approach for the development of a new strategy to inhibit apple polyphenol oxidase.


Assuntos
Antocianinas , Hibiscus , Antocianinas/análise , Hibiscus/química , Extratos Vegetais/farmacologia , Extratos Vegetais/química , Catecol Oxidase , Simulação de Acoplamento Molecular , Ácido Gálico , Glucosídeos
14.
Molecules ; 28(18)2023 Sep 20.
Artigo em Inglês | MEDLINE | ID: mdl-37764489

RESUMO

In order to develop a new type of antioxidants with high efficiency, a series of ß-ionone thiazolylhydrazone derivatives were designed and synthesized from ß-ionone, and their structures were characterized by 1H-NMR, 13C-NMR, FT-IR, and HR-MS. The antioxidant test in vitro indicated that most of the target compounds had high biological activity. Among them, compound 1k exhibited very strong DPPH (1,1-diphenyl-2-picrylhydrazyl radical)-scavenging activity with a half-maximal effective concentration (IC50) of 86.525 µM. Furthermore, in the ABTS (2,2-azinobis (3-ethylbenzothiazoline-6-sulfonate) diammonium salt)-scavenging experiment, compound 1m exhibited excellent activity with an IC50 of 65.408 µM. Their biological activities were significantly better than those of the positive control Trolox. These two compounds, which have good free-radical-scavenging activity in vitro, were used as representative compounds in the anti-browning experiment of fresh-cut potatoes. The results showed that 1k and 1m had the same anti-browning ability as kojic acid, and they were effective browning inhibitors. In addition, it is well known that microbial infection is one of the reasons for food oxidation. Therefore, we investigated the antifungal activity of 25 target compounds against eight plant fungi at a concentration of 125 mg/L. The results indicated that these compounds all have some antifungal activity and may become new potential fungicides. Notably, compound 1u showed the best inhibitory effect against Poria vaporaria, with an inhibition rate as high as 77.71%; it is expected to become the dominant structure for the development of new antifungal agents.

15.
Int J Biol Macromol ; 253(Pt 3): 126962, 2023 Dec 31.
Artigo em Inglês | MEDLINE | ID: mdl-37722636

RESUMO

Paeonol, as one effective tyrosinase inhibitor, had been used as food preservative and clinical medication for skin disorders. In this study, the inhibition mechanism and binding behavior of paeonol to tyrosinase and its anti-browning property were investigated using multi-spectroscopic and molecular docking methods. Activity assay and kinetic results confirmed paeonol as a reversible mixed-type tyrosinase inhibitor. Results of the mechanistic studies were clarified using fluorescence quenching, synchronous fluorescence, CD spectra and 3D fluorescence, and showed that the binding of paeonol to tyrosinase might change the chromophore microenvironment and conformation of tyrosinase to inhibit enzyme catalytic activity. Molecular docking results revealed the detailed binding between paeonol and tyrosinase. Moreover, paeonol could prevent the browning of fresh-cut apples, as well as inhibiting PPO and POD activities and increasing APX activity. All above findings established a reliable basis for the inhibitory mechanism of paeonol against tyrosinase and therefore contributed to its application in anti-browning.


Assuntos
Malus , Monofenol Mono-Oxigenase , Simulação de Acoplamento Molecular , Acetofenonas/farmacologia , Acetofenonas/química , Malus/química , Inibidores Enzimáticos/farmacologia , Inibidores Enzimáticos/química , Cinética
16.
Front Plant Sci ; 14: 1176936, 2023.
Artigo em Inglês | MEDLINE | ID: mdl-37223812

RESUMO

Enzymatic browning has a considerable negative impact on the acceptability and marketability of freshly cut apples. However, the molecular mechanism by which selenium (Se) positively affects freshly cut apples in this regard is not yet clear. In this study, 0.75 kg/plant of Se-enriched organic fertilizer was applied to "Fuji" apple trees during the young fruit stage (M5, May 25), the early fruit enlargement stage (M6, June 25), and the fruit enlargement stage (M7, July 25), respectively. The same amount of Se-free organic fertilizer was applied as a control. Herein, the regulatory mechanism by which exogenous Se exerts its anti-browning effect in freshly cut apples was investigated. The results showed that the M7 treatment applied in Se-reinforced apples could remarkably inhibit their browning at 1 h after being freshly cut. Additionally, the expression of polyphenol oxidase (PPO) and peroxidase (POD) genes treated with exogenous Se was significantly reduced compared to controls. Moreover, the lipoxygenase (LOX) and phospholipase D (PLD) genes, which are involved in membrane lipid oxidation, were expressed at higher levels in the control. The gene expression levels of the antioxidant enzymes catalase (CAT), superoxide dismutase (SOD), glutathione S-transferase (GST), and ascorbate peroxidase (APX) were upregulated in the different exogenous Se treatment groups. Similarly, the main metabolites measured during the browning process were phenols and lipids; thus, it could be speculated that the mechanism by which exogenous Se produces its anti-browning effect may be by reducing phenolase activity, improving the antioxidant capacity of the fruits, and alleviating membrane lipid peroxidation. In summary, this study provides evidence regarding and insight into the response mechanism employed by exogenous Se to inhibit browning in freshly cut apples.

17.
Food Chem ; 419: 136106, 2023 Sep 01.
Artigo em Inglês | MEDLINE | ID: mdl-37030204

RESUMO

To develop new shrimp preservative agents with dual functions of anti-browning and antibacterial, thirteen hydroxypyranone-thiosemicarbazone derivatives were prepared according to molecular hybridization. Thereinto, compound 7j (IC50 = 1.99 ± 0.19 µM) shown the strongest anti-tyrosinase activity and was about twenty-three folds stronger than kojic acid (45.73 ± 4.03 µM). The anti-tyrosinase mechanism of 7j was illustrated through enzyme kinetic, copper ion chelating ability, fluorescence quenching, ultraviolet spectrum, AFM analysis, and molecular docking study. On the other hand, antibacterial assay and time-kill kinetics analysis confirmed that 7j also had good antibacterial activity against V. parahaemolyticus (MIC = 0.13 mM). PI uptake test, SDS-PAGE, and fluorescence spectrometry analysis proved that 7j can affect the bacterial cell membrane. Finally, the shrimp preservation and safety study indicated that 7j has dual effects of inhibiting bacterial growth and preventing enzyme browning, and can be applied to the preservation of fresh shrimp.


Assuntos
Agaricales , Tiossemicarbazonas , Tiossemicarbazonas/farmacologia , Simulação de Acoplamento Molecular , Inibidores Enzimáticos/farmacologia , Antibacterianos/farmacologia , Antibacterianos/química , Conservantes Farmacêuticos , Monofenol Mono-Oxigenase/metabolismo , Relação Estrutura-Atividade , Agaricales/metabolismo
18.
Food Chem X ; 18: 100640, 2023 Jun 30.
Artigo em Inglês | MEDLINE | ID: mdl-37008720

RESUMO

Rubiscolin-6 (amino acid sequence: YPLDLF) is a selective δ-opioid receptor peptide isolated from spinach Rubisco. Its synthetic analogue, peptide YPMDIV is the most potent described so far for its increased opioid activity, thus in this work it was considered as lead compound for the design of twelve new analogues e.g. LMAS1-12. Firstly all the novel compounds have been tested for their antinociceptive and anti-inflammatory capacity in vitro and in vivo in order to evaluate their ability to maintain or loss the original activity. Among them peptides LMAS5-8 gave the best results, thus their antioxidant properties have been investigated along with their enzymatic inhibitory ability. Peptide LMAS6 shows a strong antioxidant (154.25 mg TE/g CUPRAC) and inhibitor activity on tyrosinase (84.49 mg KAE/g), indicating a potential role in food industry as anti-browning agent, while peptides LMAS5 and LMAS7 possess a modest cholinesterase inhibitory activity suggesting a conceivable use for nutraceuticals production.

19.
Food Chem ; 419: 136047, 2023 Sep 01.
Artigo em Inglês | MEDLINE | ID: mdl-37018861

RESUMO

A class of new kojic acid hybrids (7a-7o) bearing a 1,2,4-triazine moiety were prepared, and their inhibitory activities and mechanism on tyrosinase were investigated. All derivatives showed good to excellent anti-tyrosinase activity with IC50 values ranging from 0.34 ± 0.06 µM to 8.44 ± 0.73 µM. In kinetic study, compound 7m was a mixed-type inhibitor with Ki and Kis of 0.73 and 1.27 µM, respectively. The interaction mechanism toward tyrosinase of compound 7m was further elaborated in combination with molecular docking and various spectral techniques. The results showed that compound 7m could change the secondary structure of tyrosinase to reduce its catalytic activity. Anti-browning assays demonstrated that 7m inhibited the browning of bananas effectively during storage. What's more, 7m was found to have low cytotoxicity in vitro. In conclusion, compound 7m has the potential to be applied as an anti-browning agent.


Assuntos
Monofenol Mono-Oxigenase , Inibidores Enzimáticos/química , Inibidores Enzimáticos/farmacologia , Agaricales/química , Simulação de Acoplamento Molecular
20.
Foods ; 12(6)2023 Mar 21.
Artigo em Inglês | MEDLINE | ID: mdl-36981261

RESUMO

The fresh-cut bulbs of the Lanzhou lily (Lilium davidii var. unicolor) experience browning problems during storage. To solve the problem of browning in the preservation of Lanzhou lily bulbs, we first investigated the optimal storage temperature and gas ratio of modified atmosphere packaging (MAP) of Lanzhou lily bulbs. Then, we tested the browning index (BD), activity of phenylalanine ammonia lyase (PAL), polyphenol oxidase (PPO) and peroxidase (POD), the content of malonaldehyde (MDA) and other physiological activity indicators related to browning. The results showed that the storage conditions of 10% O2 + 5% CO2 + 85% N2 and 4 °C were the best. To further explore the anti-browning mechanism of MAP in fresh-cut Lanzhou lily bulbs, the integration of metabolome and transcriptome analyses showed that MAP mainly retarded the unsaturated fatty acid/saturated fatty acid ratio in the cell membrane, inhibited the lipid peroxidation of the membrane and thus maintained the integrity of the cell membrane of Lanzhou lily bulbs. In addition, MAP inhibited the oxidation of phenolic substances and provided an anti-tanning effect. This study provided a preservation scheme to solve the problem of the browning of freshly cut Lanzhou lily bulbs, and discussed the mechanism of MAP in preventing browning during the storage of the bulbs.

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