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1.
Food Chem ; 366: 130602, 2022 Jan 01.
Artigo em Inglês | MEDLINE | ID: mdl-34314934

RESUMO

The effect of cinnamaldehyde (CA) on the structure and properties of whey protein isolate (WPI) was investigated. The resultant WPI/CA complex was used as stabilizer to form emulsions and emulsion gels, which were used for the delivery and protection of ß-carotene. The particle size and hydrophobicity of WPI solution increased and then decreased with the addition of CA. Circular dichroism showed that CA mainly changed the secondary structure of WPI, with increasing ß-fold content from 47.2% to 72.9%. The fluorescence spectra showed that both tryptophan and tyrosine in WPI were involved in the interaction with CA. WPI/CA complex as the stabilizer could form the stable emulsions and emulsion gels, which showed better protection effect on ß-carotene, and helped enhance its bioaccessibility. The knowledge provides insights into the development of new multifunctional food ingredients and the enhancement of protein modification in food system.


Assuntos
Carotenoides , beta Caroteno , Acroleína/análogos & derivados , Emulsões , Géis , Proteínas do Soro do Leite
2.
Chemosphere ; 286(Pt 2): 131791, 2022 Jan.
Artigo em Inglês | MEDLINE | ID: mdl-34371361

RESUMO

Exposure to acrolein was reported to be related with adverse health effects. However, the associations between acrolein exposure and blood lipids remain largely unknown. We assessed the associations of urinary acrolein metabolites with blood lipids using data from the National Health and Nutrition Examination Survey (NHANES) and further investigated the existence of mediation by systemic inflammation in the associations. Urinary acrolein metabolites, N-acetyl-S-(carboxyethyl)-l-cysteine (CEMA) and N-acetyl-S-(3-hydroxypropyl)-l-cysteine (3-HPMA), blood lipids, and serum high sensitivity C-reactive protein (hs-CRP) were measured in the NHANES. The associations of urinary acrolein metabolites with blood lipids and dyslipidemia and hs-CRP were estimated by multiple linear and logistic regression models. Mediation analysis was conducted to evaluate the mediating effects of hs-CRP on the associations between urinary acrolein metabolites and blood lipids. We found urinary CEMA+3-HPMA (∑acrolein) was significantly associated with higher levels of serum triglycerides (TG), hs-CRP, and lower levels of high-density lipoprotein cholesterol (HDL-C). Each 1-unit increment in ln-transformed level of ∑acrolein was associated with a 0.06 mmol/L increment in TG and 0.02 mmol/L decrement in HDL-C (all P <0.05). A positive dose-response relationship was observed between urinary ∑acrolein and dyslipidemia risk. In addition, hs-CRP significantly mediated the associations of urinary ∑acrolein with serum TG and HDL-C, with mediated proportions of 22.12% and 41.41%, respectively. In conclusion, acrolein exposure is associated with the levels of serum TG, HDL-C, and hs-CRP. Hs-CRP may mediate acrolein-associated alterations of blood lipids. Our results indicated that decreased exposure to acrolein may reduce systemic inflammation and dyslipidemia risk.


Assuntos
Acroleína , Lipídeos , HDL-Colesterol , Humanos , Inflamação/induzido quimicamente , Inquéritos Nutricionais
3.
J Agric Food Chem ; 69(45): 13628-13636, 2021 Nov 17.
Artigo em Inglês | MEDLINE | ID: mdl-34739242

RESUMO

Cinnamaldehyde is a natural antimicrobial food preservative. Previous studies have suggested that cinnamaldehyde interacts with the cell membrane, but the molecular targets of cinnamaldehyde action on foodborne pathogens are still unclear. In this study, the structural changes of Staphylococcus aureus and Escherichia coli cells were observed after cinnamaldehyde treatment. Then, quantitative real-time polymerase chain reaction (PCR) and parallel reaction monitoring were used for determining the effects of cinnamaldehyde treatment of these bacteria on the expression of genes and proteins associated with glycerophospholipid biosynthesis. Changes in fatty acids (raw materials for the biosynthesis of glycerophospholipids) and glycerophospholipids in S. aureus and E. coli after cinnamaldehyde treatment were analyzed to confirm the results of gene and protein expression experiments. Cinnamaldehyde regulated the glycerophospholipid biosynthesis pathways of these foodborne pathogens, mainly targeting phosphatidylglycerol and phosphatidylethanolamine, which resulted in the disruption of cell membrane integrity.


Assuntos
Anti-Infecciosos , Staphylococcus aureus , Acroleína/análogos & derivados , Acroleína/farmacologia , Antibacterianos/farmacologia , Escherichia coli/genética , Fosfatidiletanolaminas , Fosfatidilgliceróis
4.
Pestic Biochem Physiol ; 179: 104976, 2021 Nov.
Artigo em Inglês | MEDLINE | ID: mdl-34802526

RESUMO

Induced resistance in harvested fruit and vegetables is a superior strategy to reduce postharvest decay. In the present study, Cinnamaldehyde (CA) was applied to investigate for its induced resistance against Penicillium digitatum and Geotrichum citri-aurantii. The results showed that 5250 mg CA/L wax was effective concentration in inducing the resistance of citrus fruit to green mold and sour rot. Wax+ CA (WCA) reduced significantly green mold and sour rot incidences at different exposure times, with 24 h being the optimal exposure time. The host reactions under infection with different pathogens were similar. During initial exposure, treatment with 5250 mg CA/L wax enhanced significantly the activities of phenylalanine ammonia-lyase (PAL), peroxidase (POD), polyphenol oxidase (PPO), ß-1, 3-glucanase (GLU) and chitinase (CHT) in the presence of direct contact with the pathogen. Simultaneously, WCA induced an increase in total phenolic, flavanone and dihydroflavonol, flavone and flavonol, and lignin contents. Thus, our results suggest that treatment using 5250 mg CA/L wax can be applied early to control diseases by provoking response reactions in citrus fruit.


Assuntos
Citrus , Penicillium , Acroleína/análogos & derivados , Geotrichum , Doenças das Plantas
5.
J Agric Food Chem ; 69(40): 11937-11946, 2021 Oct 13.
Artigo em Inglês | MEDLINE | ID: mdl-34607437

RESUMO

Acrolein (ACR), the simplest α,ß-unsaturated aldehyde, possesses high reactivity and toxicity both in vitro and in vivo and results in various chronic diseases. This has attracted increasing interest from researchers to screen various bioactive compounds to control it. In this article, we attempted to discover a new attribute of cyanidin-3-O-glucoside (C3G), including its ACR-scavenging capacity, reaction pathway, and possible application. Our findings revealed that C3G could capture ACR to form mono- and diadducts at room temperature by using liquid chromatography-mass spectrometry, and we further synthesized and elucidated the structures of C3G-ACR and C3G-2ACR using HRMS and 2D NMR. The structural data validated that there were two active sites of C3G for trapping ACR: at C-6 in the A-ring and C-5' in the B-ring. In addition, we found that C3G-ACR exhibited a more remarkable clearing ability than C3G within a short time. More than 65.9% of ACR was eliminated by C3G-ACR within 5 min via further formation of C3G-2ACR, but there was no obvious effect of C3G on ACR. When the incubation time was extended to 120 min, C3G could remove up to 83.2% of ACR. Subsequently, we also observed that mynica red (>5% C3G), as a pigmented food additive, could efficiently eliminate ACR generated in the Chinese liquor model and real red bayberry wine products to form C3G-ACR and C3G-2ACR. Both adducts increased significantly, by 10 times to a 100 times, after adding mynica red to red bayberry wine products for 24 h; they also increased rapidly with prolonged incubation time in the liquor-mynica red model system. Therefore, our findings suggest that C3G or mynica red may be developed as a promising novel ACR inhibitor in fruit wine and assembled alcoholic drinks or as a health food.


Assuntos
Acroleína , Myrica , Antocianinas , Cromatografia Líquida , Glucosídeos
6.
Molecules ; 26(20)2021 Oct 19.
Artigo em Inglês | MEDLINE | ID: mdl-34684884

RESUMO

Cinnamomum verum is widely used in traditional medicines, and the different parts of the plant, such as bark, leaves, and flowers, are used for essential oil production. The present study compared the chemical composition of the essential oil of C. verum extracted from the leaves and flowers. In addition, efficacy of these essential oils against the two common pests Sitophilus oryzae and Callosobruchus maculatus was also evaluated. The results indicated the presence of cinnamaldehyde, eugenol, caryophyllene, and linalool in these essential oils, however, at different concentrations. The leaf essential oil was found to be 10-20% more effective as a fumigant against both the pests. Likewise, the leaf essential oil found to repel these pests even at lower concentrations than that of flower essential oil of C. verum. Besides, these essential oils were also effective in controlling the growth of various gram positive and gram negative microbial pathogens and possibly a safeguard for human health. On contrary, both the essential oils were found to be safe for the application on grains, as indicated by their germination potentials. It was also observed that these essential oils do not cause any significant toxicity to guppy fishes, thus confirming their ecological safety for use as a biopesticide.


Assuntos
Antibacterianos/química , Cinnamomum zeylanicum/química , Flores/química , Repelentes de Insetos/química , Inseticidas/química , Óleos Voláteis/química , Folhas de Planta/química , Acroleína/análogos & derivados , Acroleína/química , Acroleína/farmacologia , Monoterpenos Acíclicos/química , Monoterpenos Acíclicos/farmacologia , Antibacterianos/farmacologia , Repelentes de Insetos/farmacologia , Inseticidas/farmacologia , Óleos Voláteis/farmacologia , Óleos Vegetais/química , Óleos Vegetais/farmacologia
7.
BMC Musculoskelet Disord ; 22(1): 894, 2021 Oct 20.
Artigo em Inglês | MEDLINE | ID: mdl-34670524

RESUMO

BACKGROUND: Acrolein is a known pro-inflammatory toxic aldehyde, propagating cellular damage and tissue inflammation in humans and animal models of various diseases. Osteoarthritis (OA) has a significant inflammatory component; however, presence of acrolein in synovial fluid of joints with OA has not been previously reported. The first aim of this study was to evaluate evidence of acrolein in the synovial fluid of dogs with OA as well as in Control joints. The second aim was to determine if evidence of acrolein can be detected in synovial fluid samples that have been in a frozen state for long periods of time. METHODS: In this pilot clinical study, synovial fluid samples were prospectively collected (i.e., New samples) from a single joint of both clinically healthy (New Control, n = 5) and dogs with OA (New OA, n = 16) and frozen until the time of analysis. Additionally, frozen synovial fluid samples from a biobank (i.e., Old samples) were used to evaluate ability to detect evidence of acrolein in long-term stored samples (median of 4.89 years) in Old Control (n = 5) and Old OA (n = 5) samples. Measurements of acrolein in all synovial fluid samples was based on detection of its major protein adduct, N ε - (3-formyl-3, 4-dehydropiperidino)lysine (FDP-lysine), using the western blot method. Synovial fluid matrix metalloproteinase 2 (MMP2) was measured in all samples using the western blot method as a positive control of OA inflammation. RESULTS: Acrolein-lysine adduct was detected in both Control (n = 10) and OA (n = 21) groups in both Old and New samples. Acrolein-lysine adduct and MMP2 were detectable at a lower level in the Old compared to New synovial fluid samples; however, the differences were not statistically significant (p > 0.1). The measured MMP2 levels were significantly higher in the OA compared to Control group samples (p = 0.033), but not for acrolein-lysine adduct (p = 0.30). CONCLUSIONS: This study confirmed evidence of acrolein in canine synovial fluid of both OA and Control groups. Freezing of synovial fluid for up to 5 years does not appear to significantly affect the ability to detect acrolein-lysine adduct and MMP2 in these samples.


Assuntos
Osteoartrite , Líquido Sinovial , Acroleína , Animais , Biomarcadores , Cães , Metaloproteinase 2 da Matriz , Osteoartrite/diagnóstico
8.
J Agric Food Chem ; 69(44): 13143-13154, 2021 Nov 10.
Artigo em Inglês | MEDLINE | ID: mdl-34714663

RESUMO

Acrolein (ACR) derives from the external environment and the endogenous metabolism of organisms. It has super-reactivity and can induce various diseases. We investigated the capacity of cyanidin-3-O-glucoside (C3G) and its degradants/metabolites to capture ACR during thermal processing or in vivo. Our results indicated that both C3G and its degradants, including phloroglucinaldehyde (PGA) and protocatechuic acid (PCA), could efficiently trap ACR to form adducts, such as C3G-ACR, C3G-2ACR, PGA-ACR, PGA-2ACR, PCA-ACR, and PCA-2ACR. Additionally, these adducts were detected in commercial canned red bayberry products. The adducts of C3G and its metabolites conjugated with ACR, such as C3G-ACR, C3G-2ACR, PGA-ACR, and 4-hydroxybenzoic-acid-ACR (4-HBA-ACR), were also detected in mice feces treated with C3G by oral gavage, where the adduct level was dose-dependent. A similar pattern was observed in tests on human consumption of red bayberry. In human urine, only PGA-2ACR and 4-HBA-ACR, were found, whereas C3G-ACR, C3G-2ACR, myricetin-3-O-rhamnoside-ACR (M3R-ACR), PGA-2ACR, 4-HBA-ACR and ferulic acid-ACR (FA-ACR) were detected in human feces following administration of red bayberry. Our results are the first demonstration that C3G and its metabolites can capture ACR in vitro and in vivo (mice and humans) and present a novel strategy, the development of C3G as a promising ACR inhibitor.


Assuntos
Myrica , Acroleína , Animais , Antocianinas , Glucosídeos , Camundongos
9.
Aquat Toxicol ; 240: 105995, 2021 Nov.
Artigo em Inglês | MEDLINE | ID: mdl-34673467

RESUMO

As electronic cigarettes (e-cigarettes) become increasingly popular smoking devices, there is an increased risk for unintended exposure to e-cigarette liquids through improper disposal resulting in leaching into the environment, third hand vapor exposure through air, or embryonic exposure through maternal vaping. Thus, the safety of e-cigarettes for wildlife and developing embryos need to be thoroughly investigated. We examined perturbations in zebrafish embryonic development after exposures to two cinnamon flavored vaping liquids (with 12 mg/ml nicotine and without nicotine) for e-cigarettes from two different vendors, as well as the flavoring chemical cinnamaldehyde. We focused on the effects of the vaping liquids on hatching success and bone, cartilage and blood vessel development in 3-4 days old transgenic zebrafish larvae. We found that exposures to both of the vaping liquids perturbed the development of the cleithrum and craniofacial cartilage. Exposure to the liquids further caused non-overlapping and partially or completely missing intersegmental vessels. Hatching success was also reduced. Exposure to pure cinnamaldehyde replicated the effects of the vaping liquids with a 50% effect concentration (EC50) of 34-41 µM. Quantification of the amount of cinnamaldehyde in the vaping liquids by mass spectrometry revealed EC50s around 10-40 times lower than for pure cinnamaldehyde, suggesting that additional compounds or metabolites present in the vaping liquids mediate toxicity. Presence of nicotine in one of the vaping liquids decreased its EC50s about two fold compared to the liquid without nicotine. Exposure to the humectants propylene glycol and vegetable glycerin did not affect the vascular, cartilage or bone development in zebrafish embryos. In conclusion, our study shows that exposure to cinnamaldehyde containing vaping liquids causes severe tissue-specific defects in developing embryos.


Assuntos
Sistemas Eletrônicos de Liberação de Nicotina , Vaping , Poluentes Químicos da Água , Acroleína/análogos & derivados , Animais , Cartilagem , Poluentes Químicos da Água/toxicidade , Peixe-Zebra
10.
J Agric Food Chem ; 69(40): 11926-11936, 2021 Oct 13.
Artigo em Inglês | MEDLINE | ID: mdl-34587738

RESUMO

People are at high risk of exposure to endogenous and exogenous acrolein (ACR). ACR can cause a multitude of illnesses, including cardiovascular disease, Alzheimer's disease, and diabetes. In this study, we investigated the reaction pathway of cardamonin (CAR) or alpinetin (ALP) with ACR and the interconversion of CAR and ALP in vitro at 37 °C in phosphate-buffered saline using liquid chromatography-tandem mass spectrometry (LC-MS/MS). Subsequently, ACR adducts of CAR, ALP, and their metabolites, for example, CAR-ACR-1, ALP-ACR, mono-ACR-pinocembrin chalcone (PIN-ACR), and mono- and di-ACR-naringenin (NAR-ACR and NAR-2ACR), were detected in urine samples, but only CAR-ACR-1 and ALP-ACR were detected in fecal samples from the CAR- and ALP-treated mouse groups using ultraperformance liquid chromatography-MS/MS, respectively. Quantitative analyses showed that CAR, ALP, and their metabolites markedly scavenged ACR in a dose-dependent manner in vivo. Furthermore, we also found that the metabolites of CAR or ALP remained and promoted the ACR-trapping ability.


Assuntos
Acroleína , Espectrometria de Massas em Tandem , Animais , Chalconas , Cromatografia Líquida , Flavanonas , Camundongos
11.
Environ Sci Technol ; 55(19): 12809-12817, 2021 10 05.
Artigo em Inglês | MEDLINE | ID: mdl-34523924

RESUMO

Airborne carbonyl compounds such as formaldehyde, acrolein, and methyl ethyl ketone have long been chemicals-of-concern in the environment due to their reactivity and their potential for negative health effects. Standard methods for determining carbonyls in air, which focus on a set of 15 or fewer compounds, involve derivatization to form nonvolatile hydrazones, which can readily be analyzed via liquid chromatography (LC) with ultraviolet detectors. Here, we apply a new LC-high-resolution mass spectrometry (HRMS) method to natural gas and a variety of upgraded biofuels to better assess their total carbonyl profile using the inherent selectivity of the standard sampling methodology and the selectivity and sensitivity of HRMS. The standard method accounted for only 64% of the total carbonyl content in natural gas and between 26 and 45% of the total carbonyl content in biogas sources, with the balance detected by the new LC/HRMS method. An additional 540 compounds with molecular formulas consistent with carbonyl compounds were detected compared to only 14 target compounds using the standard method. These results demonstrate that the established method dramatically under-reports both the total carbonyl load and the diversity of carbonyl species in natural gas and biogas samples.


Assuntos
Biocombustíveis , Gás Natural , Acroleína , Formaldeído , Espectrometria de Massas
12.
Environ Sci Process Impacts ; 23(11): 1729-1746, 2021 Nov 17.
Artigo em Inglês | MEDLINE | ID: mdl-34591059

RESUMO

Acrolein (2-propenal) is a reactive substance undergoing multiple reaction pathways and an airborne pollutant with known corrosive, toxic and hazardous effects to the environment and to human health. So far, investigating the occurrence of acrolein in indoor air has been challenging due to analytical limitations. The classic DNPH-method has proven to be error-prone, even though it is still recommended in specific testing protocols. Thus, different approaches for an accurate determination of ambient acrolein have been introduced. In this work, an overview of already published data regarding emission sources and air concentrations is provided. In addition, a new method for the quantitative determination of acrolein in environmental test chambers and in indoor air is presented. Analysis is carried out using thermal desorption and coupled gas chromatography/mass spectrometry (TD-GC/MS) after sampling on the graphitized carbon black (GCB) Carbograph™ 5TD. All analytical steps have been carefully validated and compared with derivatization techniques (DNPH and DNSH) as well as online detection using PTR-QMS. The sampling time is short due to the low air collection volume of 4 L. Although derivatization is not applied, a detection limit of 0.1 µg m-3 can be achieved. By increasing the sampling volume to 6 L, the limit of detection can be lowered to 0.08 µg m-3. No breakthrough during sampling or analyte loss during storage of the acrolein laden sampling tubes was found. Therefore, the presented method is robust, easy-to-handle and also very suitable for routine analyses and surveys.


Assuntos
Acroleína , Atmosfera , Acroleína/análise , Cromatografia Gasosa-Espectrometria de Massas , Humanos
13.
Chemosphere ; 283: 131183, 2021 Nov.
Artigo em Inglês | MEDLINE | ID: mdl-34467940

RESUMO

Air-water interfaces are ubiquitous in nature, as manifested in the form of the surfaces of oceans, lakes, and atmospheric aqueous aerosols. The aerosol droplets interface, in particular, plays a critical role in numerous atmospheric chemistry processes. Methyl vinyl ketone (MVK) and methacrolein (MACR), two abundant volatile organic compounds, are the significant precursors of Criegee intermediates and secondary organic aerosol. In this work, the physicochemical properties of MVK and MACR at the air-water interface are studied from a theoretical perspective. The free energy wells of MVK and MACR occur at the air-water interface, and the absorption probabilities of them are 71% and 67%, respectively. Repulsion dominates the interactions between MVK/MACR and water molecules in the bulk region, while attraction is dominant at the interface. The two molecules tend to tilt at the interface, with the CC bond exposed at the outer interface. The most likely reaction scenario of O3-initiated MVK/MACR reaction in the troposphere is also determined for the first time. Based on the molecular dynamics simulation results, the activity sequence of MVK + O3 is given at four different environments by the density functional theory method: air-water interface, mineral clusters interface, bulk solution, and homogeneous gas. The interfacial water molecule can catalyze the reaction of MVK with O3, and the rate constant at the air-water interface is ~6 times larger than that on the mineral surface model. Compared with mineral particles, aqueous particles play a more significant role in modifying the reaction properties of atmospheric organic species.


Assuntos
Poluentes Atmosféricos , Água , Acroleína/análogos & derivados , Adsorção , Poluentes Atmosféricos/análise , Butanonas , Meio Ambiente , Água/análise
14.
Chem Commun (Camb) ; 57(77): 9798-9806, 2021 Sep 28.
Artigo em Inglês | MEDLINE | ID: mdl-34581321

RESUMO

Acrolein holds excellent potential as a biomarker in various oxidative stress-related diseases, including cancer, Alzheimer's, Parkinson's, and inflammatory disorders. Consequently, a direct method to target and visualize acrolein in biological systems might be essential to provide tools for diagnosis and therapeutic purposes. Previously, we discovered 1,3-dipolar cycloaddition between aryl azides and acrolein, which proceeds without a catalyst to give α-diazocarbonyl derivatives. The reaction proceeds with high reactivity and selectivity even under physiological conditions. We have successfully utilized the reaction as a robust method for detecting acrolein generated by cancer cells. This review discusses the utilization of the endogenous acrolein reaction with aryl azide to (1) distinguish breast cancer from normal tissue during breast-conserving surgery and (2) treat cancer through selective prodrug activation in a mouse model without causing adverse effects. The methods have potential clinical application for breast-conserving surgery and are highly advantageous for cancer therapy.


Assuntos
Acroleína/química , Antineoplásicos/uso terapêutico , Neoplasias da Mama , Imagem Óptica , Pró-Fármacos/uso terapêutico , Animais , Antineoplásicos/química , Neoplasias da Mama/diagnóstico por imagem , Neoplasias da Mama/tratamento farmacológico , Feminino , Humanos , Pró-Fármacos/química
15.
Phytomedicine ; 91: 153703, 2021 Oct.
Artigo em Inglês | MEDLINE | ID: mdl-34425473

RESUMO

BACKGROUND: Depressive-like behaviors are related to inflammatory immune activation. Cinnamomum verum (CV) has anti-inflammatory effects, but the molecular mechanisms underlying the antidepressant effects after immunological activation still remain elusive. PURPOSE: The aim of the present study was to investigate the effect of CV in improving depressive-like behavior and explore its underlying mechanism in T lymphocytes. METHODS: Mice were randomly divided into Control, LPS, LPS plus fluoxetine, LPS plus CV, and LPS plus MCA groups. Behavior was evaluated using forced swimming test (FST) and tail suspension test (TST). The experimental group mice were exposed to LPS to induce depressive-like behavior. Cell viability was measured upon treating splenic T lymphocytes and Jurkat T cells with CV. Cytokine activity was measured using ELISA and RT-qPCR. The components of CV were analyzed by HPLC. NFAT expression was evaluated by western blotting, immunofluorescence, and luciferase assay. To verify the half-life of NFAT mRNA, Jurkat cells were treated with actinomycin D for 1.5, 3, and 4.5 h. RESULTS: CV effectively prevents inflammation-induced depressive-like behaviors. CV dose-dependently decreased protein and mRNA levels of TNFα and IL-2. Inhibition of TNFα and IL-2 production involves an MCA-mediated decrease in NFAT mRNA level, rather than inhibition of nuclear translocation. This mechanism was independent of NFAT transcription inducer p38 MAPK; it can be attributed to the promotion of NFAT mRNA decay. CONCLUSION: Overall, MCA might be an alternative or adjuvant to existing NFAT-targeting immunosuppressants for clinical prophylaxis or therapy in the context of inflammation-induced depressive disorder or other T-cell-associated inflammatory disorders.


Assuntos
Acroleína/análogos & derivados , Cinnamomum zeylanicum , Depressão , Fatores de Transcrição NFATC , Estabilidade de RNA , Linfócitos T/efeitos dos fármacos , Acroleína/farmacologia , Animais , Comportamento Animal , Cinnamomum zeylanicum/química , Depressão/tratamento farmacológico , Lipopolissacarídeos , Camundongos , Camundongos Endogâmicos ICR
16.
Colloids Surf B Biointerfaces ; 207: 112052, 2021 Nov.
Artigo em Inglês | MEDLINE | ID: mdl-34416443

RESUMO

Chemotherapy fails to achieve an ideal gliomas therapy due to the limited delivery of chemotherapeutics across the blood brain barrier (BBB), difficult accumulation of drugs in the gliomas area, and off-target toxicity. Herein, the pH-triggered small molecule nano-prodrugs (Try-CA-NPs) emulsified from hydrophobic tryptamine (Try)-cinnamaldehyde (CA) twin drug were successfully prepared through a facile method. Try-CA-NPs exhibited long-term storage and circulation stability. Furthermore, liposoluble Try-CA-NPs could easily cross BBB and efficiently accumulate in brain, selectively target to gliomas cells via Try-mediated cellular uptake, and enhance cytotoxicity through intracellular pH-triggered endosomal escape and efficient drug release, and synergistic effect between CA and Try, therefore achieving the complete destruction of SH-SY5Y multicellular spheroids (MCs). Thus, the pH-triggered small molecule nano-prodrugs emulsified from Try-CA twin drug have the great potential for clinically targeted synergistic glioma therapy.


Assuntos
Glioma , Nanopartículas , Pró-Fármacos , Acroleína/análogos & derivados , Sistemas de Liberação de Medicamentos , Glioma/tratamento farmacológico , Humanos , Concentração de Íons de Hidrogênio , Triptaminas
17.
J Agric Food Chem ; 69(36): 10700-10708, 2021 Sep 15.
Artigo em Inglês | MEDLINE | ID: mdl-34464123

RESUMO

Synthesis of proanthocyanidin-cinnamaldehydes pyrylium products (PCPP) was achieved by the condensation reaction of proanthocyanidins (PAC) with cinnamaldehyde and four cinnamaldehyde derivatives. Matrix-assisted laser desorption/ionization time-of-flight mass spectrometry (MALDI-TOF MS) spectra of PCPP show masses that correspond to (epi)catechin oligomers attached to single, double, or triple moieties of cinnamaldehydes. Synthesized PCPP exhibited fluorescence at higher excitation and emission wavelengths than PAC. Results indicate that PCPP were more bioactive for agglutinating extra-intestinal pathogenic Escherichia coli (ExPEC) compared to PAC. Scanning electron microscopy indicates that PCPP interact with ExPEC surface structures and suggests that PCPP have a higher affinity with the fimbriae-like structures of ExPEC than PAC. Fluorescent microscopy performed on in vitro and in vivo agglutination assays show that PCPP were entrapping ExPEC in a web-like network, thus demonstrating agglutination of ExPEC. This study demonstrated the potential of PCPP to improve our understanding of the temporal and dynamic interactions of PAC in in vitro and in vivo studies.


Assuntos
Proantocianidinas , Vaccinium macrocarpon , Acroleína/análogos & derivados , Escherichia coli , Espectrometria de Massas por Ionização e Dessorção a Laser Assistida por Matriz
18.
Sci Rep ; 11(1): 16281, 2021 08 11.
Artigo em Inglês | MEDLINE | ID: mdl-34381064

RESUMO

Essential oils and their active components, referred here as plant derived antimicrobials (PDAs), have been used for their antimicrobial, anti-inflammatory and antioxidant properties. Many reports also document PDAs' cytotoxic effects on cancerous cells, raising the hope that they could be used for cancer treatments. Due to the lack of specificity, we hypothesize that PDAs are cytotoxic to both cancerous and non-cancerous cells. Trans-cinnamaldehyde (TCA), carvacrol, and eugenol were assessed for their cytotoxicity on cancerous HeLa cells and normal skin fibroblasts (CCD-1123Sk, CCD) by MTT and LDH assays, flow cytometry, and reverse transcription quantitative PCR (RT-qPCR). After 24 h of treatment, carvacrol and TCA significantly decreased cell viability (by more than 50%) at 100 µg/ml, whereas eugenol was ineffective up to 400 µg/ml. Cell detachment and significantly increased apoptosis were observed with 100 µg/ml of TCA on both cell types. RT-qPCR for apoptotic genes (BCL2, CASP3 and CASP8) and necrosis genes (MLKL, RIPK1 and RIPK3) did not show significant differences between control and treated cells of both types, with the exception of eugenol-treated HeLa cells in which expression of BCL2, MLKL and RIPK1 was significantly higher than controls. Taken together, we conclude that the three PDAs studied here exhibited similar cytotoxic effects on both cancerous and non-cancerous cells.


Assuntos
Acroleína/análogos & derivados , Cimenos/farmacologia , Citotoxinas/farmacologia , Eugenol/farmacologia , Acroleína/farmacologia , Apoptose/efeitos dos fármacos , Linhagem Celular Tumoral , Sobrevivência Celular/efeitos dos fármacos , Fibroblastos/efeitos dos fármacos , Células HeLa , Humanos , Óleos Voláteis/farmacologia
19.
Cells ; 10(8)2021 08 10.
Artigo em Inglês | MEDLINE | ID: mdl-34440820

RESUMO

The identification of cancer stem cells in brain tumors paved the way for new therapeutic approaches. Recently, a role for the transcriptional factor Runx1/Aml1 and the downstream ion channel genes in brain cancer development and progression has been suggested. This study aimed to explore the expression and the role of Runx1/Aml1, its Aml1b and Aml1c splice variants and the downstream TRPA1 and TRPV1 ion channels in undifferentiated and day-14 differentiated neural stem cells (NSCs and D-NSCs) and glioblastoma stem cells (GSCs and D-GSCs) lines with different proneural (PN) or mesenchymal (MES) phenotype. Gene and protein expression were evaluated by qRT-PCR, cytofluorimetric, western blot and confocal microscopy analyses. Moreover, by western blot, we observed that ERK phosphorylation enhances the Aml1b and Aml1c protein expression during glioma differentiation. Furthermore, the agonists of TRPA1 and TRPV1 channels stimulated apoptosis/necrosis in GSCs and D-GSCs as evaluated by Annexin V and PI staining and cytofluorimetric analysis. Finally, by qRT-PCR, the modulation of Wnt/ß catenin, FGF, and TGFß/SMAD signaling pathways in PN- and MES-GSCs was reported. Overall, our results provide new evidence regarding Runx1/Aml1 isoform overexpression and modulation in TRP channel expression during gliomagenesis, thus offering new directions for glioblastoma therapy.


Assuntos
Subunidade alfa 2 de Fator de Ligação ao Core/genética , MAP Quinases Reguladas por Sinal Extracelular/metabolismo , Células-Tronco Neoplásicas/metabolismo , Acroleína/análogos & derivados , Acroleína/farmacologia , Apoptose/efeitos dos fármacos , Neoplasias Encefálicas/metabolismo , Neoplasias Encefálicas/patologia , Diferenciação Celular , Linhagem Celular Tumoral , Subunidade alfa 2 de Fator de Ligação ao Core/metabolismo , Regulação para Baixo/efeitos dos fármacos , Glioma/metabolismo , Glioma/patologia , Humanos , Células-Tronco Neoplásicas/citologia , Fator de Crescimento Neural/genética , Fator de Crescimento Neural/metabolismo , Fosforilação , Isoformas de Proteínas/genética , Isoformas de Proteínas/metabolismo , Splicing de RNA , Transdução de Sinais/genética , Canal de Cátion TRPA1/agonistas , Canal de Cátion TRPA1/genética , Canal de Cátion TRPA1/metabolismo , Canais de Cátion TRPV/agonistas , Canais de Cátion TRPV/genética , Canais de Cátion TRPV/metabolismo , Regulação para Cima/efeitos dos fármacos
20.
Sci Total Environ ; 800: 149532, 2021 Dec 15.
Artigo em Inglês | MEDLINE | ID: mdl-34426310

RESUMO

Considering the moderate acidity of aerosols, the formation of secondary organic aerosols (SOA) through acid-catalyzed heterogeneous reactions has become a recent concern. However, the detailed information on the multiphase chemistry of organic compounds adsorbed onto acidic aerosols remains uncertain. In this work, we investigated the multiphase chemical processes between methacrolein (MACR) and sulfuric acid (SA) and their relationship with SOA formation. Results show that the aqueous nanoparticle interface, especially when it is an acidic nanoparticle interface, is a perfect area to adsorb and accommodate MACR. The occurrence percentage of MACR on the interface is more than 70%. With the increase of SA concentration, the first solvation shell changed from only water to the mixture of SA and water, which facilitates the heterogeneous hydration reaction of MACR. Compared with the neutral nanoparticle interface, the acidic nanoparticle interface exhibits a better ability to uptake and accommodate gaseous carbonyl species. Moreover, SA can catalyze the hydration reaction of MACR inside the aqueous media, and the resulting oligomers contribute to the formation and growth of SOA. The hydration reaction indirectly promotes the continuous adsorption of MACR at the acidic nanoparticle interface. The rate constant shows a positive altitude dependence, and acid-catalyzed reactions have an important impact on environmental chemistry, such as cloud SOA formation, within the range of about 2-6 km. This study reports a complete description of the heterogeneous interactions between unsaturated carbonyl species and acidic nanoparticles by using molecular dynamics and quantum chemistry methods, aiming to provide some insights for the further study on heterogeneous chemistry and its role in the formation of tropospheric SOA.


Assuntos
Poluentes Atmosféricos , Nanopartículas , Acroleína/análogos & derivados , Adsorção , Aerossóis , Poluentes Atmosféricos/análise
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