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1.
Food Res Int ; 188: 114506, 2024 Jul.
Artigo em Inglês | MEDLINE | ID: mdl-38823846

RESUMO

The characteristic aroma compounds of braised pork were identified through molecular sensory science and PLSR analysis, and the difference between two cooking methods, traditional open-fire (BPF) and induction cooker (BPC), was compared. Seventeen aroma compounds with odor activity values (OAVs) > 1 were identified in both samples. BPF revealed higher OAVs for most of the aroma compounds compared to BPC, and the higher aroma quality. Aroma recombination and omission experiments confirmed that twelve aroma compounds significantly contributed to the characteristic aroma of braised pork, and eight compounds such as hexanal, (E)-2-octenal, and methanethiol were further confirmed as important contributors by PLSR analysis. Furthermore, PLSR analysis clarified the role of aldehydes such as hexanal, (E)-2-octenal, and (E,E)-2,4-decadienal in contributing to fatty attribute, whereas methanethiol was responsible for the meaty aroma. These characteristic aroma compounds mainly derived from lean meat due to its high content of phospholipids, and the exogenous seasonings contributed to the balanced characteristic aroma profile of braised pork by altering the distribution of these characteristic aroma compounds. Variations in heating parameters affected the formation of lipid oxidation and Strecker degradation products, which might explain aroma discrepancy between braised pork cooked by two methods with different heat transfer efficiencies.


Assuntos
Aldeídos , Culinária , Odorantes , Culinária/métodos , Odorantes/análise , Animais , Suínos , Aldeídos/análise , Compostos Orgânicos Voláteis/análise , Carne de Porco/análise , Humanos , Compostos de Sulfidrila/análise
2.
Mikrochim Acta ; 191(7): 372, 2024 Jun 06.
Artigo em Inglês | MEDLINE | ID: mdl-38839678

RESUMO

A highly sensitive micelle-induced sensory has been developed for detection of long-chain aldehydes as potential biomarkers of respiratory cancers. The micelle-like sensor was fabricated through the partial self-assembly of CTAB and S2 surfactants, containing a fluorescent hydrazine-functionalized dye (Naph-NH2). In principle, long-chain aldehydes with amphiphilic character act as the induced-fit surfactants to form well-entrapped micellar particles, as well as react with Naph-NH2 to form hydrazone derivatives resulting in fluorescent enhancement. The limit of detection (LOD) of micellar Naph-NH2/CTAB/S2 platform was calculated to be ∼  64.09-80.98 µM for detection of long-chain aldehydes, which showed fluorescent imaging in lung cancer cells (A549). This micellar sensory probe demonstrated practical applicability for long-chain aldehyde sensing in human blood samples with an accepted percent recovery of ~ 94.02-102.4%. Beyond Naph-NH2/CTAB/S2 sensor, the milcellar hybrid sensor was successfully developed by incorporating a micelle-like platform with supramolecular gel regarding to carboxylate-based gelators (Gel1), which showed a tenfold improvement in sensitivity. Expectedly, the determination of long-chain aldehydes through these sensing platforms holds significant promise for point-of-care cancer diagnosis and therapy.


Assuntos
Aldeídos , Corantes Fluorescentes , Hidrogéis , Limite de Detecção , Micelas , Humanos , Aldeídos/química , Corantes Fluorescentes/química , Hidrogéis/química , Células A549 , Hidrazinas/química , Cetrimônio/química , Tensoativos/química
3.
Food Microbiol ; 122: 104550, 2024 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-38839218

RESUMO

Listeria monocytogenes presents significant risk to human health due to its high resistance and capacity to form toxin-producing biofilms that contaminate food. The objective of this study was to assess the inhibitory effect of citronella aldehyde (CIT) on L. monocytogenes and investigate the underlying mechanism of inhibition. The results indicated that the minimum inhibitory concentration (MIC) and Minimum sterilisation concentration (MBC) of CIT against L. monocytogenes was 2 µL/mL. At this concentration, CIT was able to effectively suppress biofilm formation and reduce metabolic activity. Crystalline violet staining and MTT reaction demonstrated that CIT was able to inhibit biofilm formation and reduce bacterial cell activity. Furthermore, the motility assessment assay revealed that CIT inhibited bacterial swarming and swimming. Scanning electron microscopy (SEM) and laser confocal microscopy (LSCM) observations revealed that CIT had a significant detrimental effect on L. monocytogenes cell structure and biofilm integrity. LSCM also observed that nucleic acids of L. monocytogenes were damaged in the CIT-treated group, along with an increase in bacterial extracellular nucleic acid leakage. The proteomic results also confirmed the ability of CIT to affect the expression of proteins related to processes including metabolism, DNA replication and repair, transcription and biofilm formation in L. monocytogenes. Consistent with the proteomics results are ATPase activity and ATP content of L. monocytogenes were significantly reduced following treatment with various concentrations of CIT. Notably, CIT showed good inhibitory activity against L. monocytogenes on cheese via fumigation at 4 °C.This study establishes a foundation for the potential application of CIT in food safety control.


Assuntos
Biofilmes , Queijo , Listeria monocytogenes , Testes de Sensibilidade Microbiana , Listeria monocytogenes/efeitos dos fármacos , Listeria monocytogenes/crescimento & desenvolvimento , Listeria monocytogenes/fisiologia , Queijo/microbiologia , Biofilmes/efeitos dos fármacos , Biofilmes/crescimento & desenvolvimento , Antibacterianos/farmacologia , Conservação de Alimentos/métodos , Microbiologia de Alimentos , Proteínas de Bactérias/metabolismo , Proteínas de Bactérias/genética , Aldeídos/farmacologia , Extratos Vegetais/farmacologia , Monoterpenos Acíclicos/farmacologia
4.
Planta Med ; 90(7-08): 554-560, 2024 Jun.
Artigo em Inglês | MEDLINE | ID: mdl-38843795

RESUMO

A selective Oxone-induced oxidation of oleocanthal and oleacein, the two main secoiridoids of olive oil, to their bis-oxidized products is described. This protocol is based on a Baeyer-Villiger mechanism and the concentration of Oxone in the final solution. The bis-oxidation of the aldehydic compounds could be extended for the synthesis of various semisynthetic analogs. The obtained acids exhibit strong antioxidant activity, being efficient free radical scavengers.


Assuntos
Aldeídos , Azeite de Oliva , Oxirredução , Aldeídos/química , Azeite de Oliva/química , Antioxidantes/química , Antioxidantes/farmacologia , Fenóis/química , Furanos/química , Monoterpenos Ciclopentânicos/química
5.
Cell Commun Signal ; 22(1): 309, 2024 Jun 04.
Artigo em Inglês | MEDLINE | ID: mdl-38835076

RESUMO

BACKGROUND: Neuroinflammation is widely acknowledged as a characteristic feature of almost all neurological disorders and specifically in depression- and anxiety-like disorders. In recent years, there has been significant attention on natural compounds with potent anti-inflammatory effects due to their potential in mitigating neuroinflammation and neuroplasticity. METHODS: In the present study, we aimed to evaluate the neuroprotective effects of oleacein (OC), a rare secoiridoid derivative found in extra virgin olive oil. Our goal was to explore the BDNF/TrkB neurotrophic activity of OC and subsequently assess its potential for modulating neuroinflammatory response using human neuroblastoma cells (SH-SY5Y cells) and an in vivo model of depression induced by lipopolysaccharide (LPS)-mediated inflammation. RESULTS: In SH-SY5Y cells, OC exhibited a significant dose-dependent increase in BDNF expression. This enhancement was absent when cells were co-treated with inhibitors of BDNF's receptor TrkB, as well as downstream molecules PI3K and MEK. Whole-transcriptomics analysis revealed that OC upregulated cell cycle-related genes under normal conditions, while downregulating inflammation-associated genes in LPS-induced conditions. Furthermore, surface plasmon resonance (SPR) assays demonstrated that OC exhibited a stronger and more stable binding affinity to TrkB compared to the positive control, 7,8-dihydroxyflavone. Importantly, bioluminescence imaging revealed that a single oral dose of OC significantly increased BDNF expression in the brains of Bdnf-IRES-AkaLuc mice. Furthermore, oral administration of OC at a dosage of 10 mg/kg body weight for 10 days significantly reduced immobility time in the tail suspension test compared to the LPS-treated group. RT-qPCR analysis revealed that OC significantly decreased the expression of pro-inflammatory cytokines Tnfα, Il6, and Il1ß, while simultaneously enhancing Bdnf expression, as well as both pro and mature BDNF protein levels in mice hippocampus. These changes were comparable to those induced by the positive control antidepressant drug fluoxetine. Additionally, microarray analysis of mouse brains confirmed that OC could counteract LPS-induced inflammatory biological events. CONCLUSION: Altogether, our study represents the first report on the potential antineuroinflammatory and antidepressant properties of OC via modulation of BDNF/TrkB neurotrophic activity. This finding underscores the potential of OC as a natural therapeutic agent for depression- and anxiety-related disorders.


Assuntos
Fator Neurotrófico Derivado do Encéfalo , Lipopolissacarídeos , Receptor trkB , Animais , Humanos , Receptor trkB/metabolismo , Fator Neurotrófico Derivado do Encéfalo/metabolismo , Fator Neurotrófico Derivado do Encéfalo/genética , Lipopolissacarídeos/farmacologia , Camundongos , Doenças Neuroinflamatórias/tratamento farmacológico , Linhagem Celular Tumoral , Monoterpenos Ciclopentânicos/farmacologia , Masculino , Fármacos Neuroprotetores/farmacologia , Fármacos Neuroprotetores/uso terapêutico , Camundongos Endogâmicos C57BL , Azeite de Oliva/farmacologia , Azeite de Oliva/química , Anti-Inflamatórios/farmacologia , Inflamação/tratamento farmacológico , Inflamação/patologia , Aldeídos , Glicoproteínas de Membrana , Fenóis
6.
Food Res Int ; 186: 114372, 2024 Jun.
Artigo em Inglês | MEDLINE | ID: mdl-38729730

RESUMO

The oxidation and degradation of fats lead to a decrease in the nutritional value of food and pose safety concerns. Saturated fatty acids also hold a significant position in the field of lipid oxidation. In this study, the oxidation products of methyl palmitate were investigated by using gas chromatography mass spectrometry (GC-MS). Seven monohydroperoxides and 72 secondary oxidation products were detected. Combined with density functional theory (DFT) calculations, the formation mechanisms of oxidation products can be summarized into four stages. The initial stage involved the formation of monohydroperoxides and alkanes, followed by the subsequent stage involving methyl x-oxo(hydroxy)hexadecanoates. The third stage involved the formation of methyl ketones, carboxylic acids, and aldehydes, while the final stage involved lactones. Meanwhile, methyl ketones were the most abundant oxidation product, approximately 25 times more abundant than aldehydes; the calculated results agreed well with the experimental results. The establishment of a comprehensive thermal oxidation mechanism for palmitic acid provided a new foundation for future lipid oxidation analyses.


Assuntos
Cromatografia Gasosa-Espectrometria de Massas , Temperatura Alta , Oxirredução , Aldeídos/química , Aldeídos/análise , Palmitatos/química , Ácido Palmítico/química , Cetonas/química , Ácidos Carboxílicos/química
7.
Cells ; 13(9)2024 Apr 24.
Artigo em Inglês | MEDLINE | ID: mdl-38727274

RESUMO

α-Synuclein (α-syn) can form oligomers, protofibrils, and fibrils, which are associated with the pathogenesis of Parkinson's disease and other synucleinopathies. Both the lipid peroxidation product 4-oxo-2-nonenal (ONE) and agitation can induce aggregation of α-syn and phosphorylated α-syn. Thus, clarification of the characteristics of different α-syn species could help to select suitable aggregates for diagnosis and elucidate the pathogenesis of diseases. Here, we characterized ONE-induced wild-type (WT) α-syn aggregates (OW), ONE-induced phosphorylated α-syn (p-α-syn) aggregates (OP), agitation-induced α-syn preformed fibrils (PFF), and agitation-induced p-α-syn preformed fibrils (pPFF). Thioflavin T (ThT) dying demonstrated that OW and OP had fewer fibrils than the PFF and pPFF. Transmission electron microscopy revealed that the lengths of PFF and pPFF were similar, but the diameters differed. OW and OP had more compact structures than PFF and pPFF. Aggregation of p-α-syn was significantly faster than WT α-syn. Furthermore, OW and OP were more sodium dodecyl sulfate-stable and proteinase K-resistant, suggesting greater stability and compactness, while aggregates of PFF and pPFF were more sensitive to proteinase K treatment. Both ONE- and agitation-induced aggregates were cytotoxic when added exogenously to SH-SY5Y cells with increasing incubation times, but the agitation-induced aggregates caused cell toxicity in a shorter time and more p-α-syn inclusions. Similarly, p-proteins were more cytotoxic than non-p-proteins. Finally, all four aggregates were used as standard antigens to establish sandwich enzyme-linked immunosorbent assay (ELISA). The results showed that the recognition efficiency of OW and OP was more sensitive than that of PFF and pPFF. The OW- and OP-specific ELISA for detection of p-α-syn and α-syn in plasma samples of Thy1-α-syn transgenic mice showed that the content of aggregates could reflect the extent of disease. ONE and agitation induced the formation of α-syn aggregates with distinct biophysical properties and biomedical applications.


Assuntos
Aldeídos , Agregados Proteicos , alfa-Sinucleína , alfa-Sinucleína/metabolismo , alfa-Sinucleína/química , Aldeídos/metabolismo , Fosforilação , Humanos , Animais , Camundongos , Linhagem Celular Tumoral , Doença de Parkinson/metabolismo , Doença de Parkinson/patologia , Fenômenos Biofísicos
8.
Food Res Int ; 183: 114183, 2024 May.
Artigo em Inglês | MEDLINE | ID: mdl-38760123

RESUMO

A large number of volatile compounds are formed during the baking of foods by reactions such as caramelization and Maillard reactions. Elucidating the reaction mechanisms may be useful to predict and control food quality. Ten reaction volatile markers were extracted during baking of solid model cakes implemented with known amounts of precursors (glucose with or without leucine) and then quantified by Thermal desorption-Gas chromatography-Mass spectrometry. The kinetic data showed that the level of air convection in the oven had no significant influence on the reaction rates. In contrast, increasing baking temperatures had a nonlinear accelerating impact on the generation of newly formed volatile compounds with a bell-shaped kinetic curve found for most of the markers at 200 °C. The presence of leucine triggered the activation of the Maillard and Strecker routes with a specific and very rapid formation of 3-Methylbutanal and pyrazines. A dynamic model was developed, combining evaporation flow rate and kinetic formation and consumption of reaction markers. It can be used to describe, for two furanic compounds of different volatilities, the vapor concentrations in the oven from the concentrations measured in the model cakes.


Assuntos
Culinária , Cromatografia Gasosa-Espectrometria de Massas , Glucose , Temperatura Alta , Leucina , Reação de Maillard , Compostos Orgânicos Voláteis , Cinética , Compostos Orgânicos Voláteis/análise , Compostos Orgânicos Voláteis/química , Culinária/métodos , Glucose/química , Glucose/análise , Leucina/química , Aldeídos/análise , Aldeídos/química , Pirazinas/análise , Pirazinas/química
9.
Food Res Int ; 187: 114330, 2024 Jul.
Artigo em Inglês | MEDLINE | ID: mdl-38763633

RESUMO

Processing technology plays a crucial role in the formation of tea aroma. The dynamic variations in volatile metabolites across different processing stages of fresh scent green tea (FSGT) were meticulously tracked utilizing advanced analytical techniques such as GC-E-Nose, GC-MS, and GC × GC-TOFMS. A total of 244 volatile metabolites were identified by GC-MS and GC × GC-TOFMS, among which 37 volatile compounds were concurrently detected by both methods. Spreading and fixation stages were deemed as pivotal processes for shaping the volatile profiles in FSGT. Notably, linalool, heptanal, 2-pentylfuran, nonanal, ß-myrcene, hexanal, 2-heptanone, pentanal, 1-octen-3-ol, and 1-octanol were highlighted as primary contributors to the aroma profiles of FSGT by combining odor activity value assessment. Furthermore, lipid degradation and glycoside hydrolysis were the main pathways for aroma formation of FSGT. The results not only elucidate the intricate variations in volatile metabolites but also offer valuable insights into enhancing the processing techniques for improved aroma quality of green tea.


Assuntos
Manipulação de Alimentos , Cromatografia Gasosa-Espectrometria de Massas , Odorantes , Chá , Compostos Orgânicos Voláteis , Compostos Orgânicos Voláteis/análise , Compostos Orgânicos Voláteis/metabolismo , Cromatografia Gasosa-Espectrometria de Massas/métodos , Odorantes/análise , Chá/química , Manipulação de Alimentos/métodos , Nariz Eletrônico , Aldeídos/análise , Aldeídos/metabolismo , Monoterpenos Acíclicos/metabolismo , Monoterpenos Acíclicos/análise , Camellia sinensis/química , Camellia sinensis/metabolismo , Cetonas/análise , Cetonas/metabolismo , Octanóis
10.
Food Res Int ; 187: 114323, 2024 Jul.
Artigo em Inglês | MEDLINE | ID: mdl-38763630

RESUMO

The balance regulation between characteristic aroma and hazards in high-temperature processed fish is a hot spot. This study was aimed to explore the interactive relationship between the nutritional value, microstructures, aroma, and harmful substances of hairtail under different frying methods including traditional frying (TF), air frying (AF), and vacuum frying (VF) via chemical pattern recognition. The results indicated that VF-prepared hairtail could form a crunchy mouthfeel and retain the highest content of protein (645.53 mg/g) and the lowest content of fat (242.03 mg/g). Vacuum frying reduced lipid oxidation in hairtail, resulting in the POV reaching 0.02 mg/g, significantly lower than that of TF (0.05 mg/g) and AF (0.21 mg/g), and TBARS reached 0.83 mg/g, significantly lower than that of AF (1.96 mg/g) (P < 0.05), respectively. Notable variations were observedin the aroma profileof hairtail preparedfrom different frying methods. Vacuum frying of hairtail resulted in higher levels of pyrazines and alcohols, whereas traditional frying and air frying were associated with the formation of aldehydes and ketones, respectively. Air frying was not a healthy way to cook hairtail which produced the highest concentration of harmful substances (up to 190.63 ng/g), significantly higher than VF (5.72 ng/g) and TF (52.78 ng/g) (P < 0.05), especially norharman (122.57 ng/g), significantly higher than VF (4.50 ng/g) and TF (32.63 ng/g) (P < 0.05). Norharman and acrylamide were the key harmful substances in hairtail treated with traditional frying. The vacuum frying method was an excellent alternative for deep-fried hairtail as a snack food with fewer harmful substances and a fine aroma, providing a theoretic guidance for preparing healthy hairtail food with high nutrition and superior sensory attraction.


Assuntos
Culinária , Temperatura Alta , Odorantes , Animais , Culinária/métodos , Odorantes/análise , Aldeídos/análise , Valor Nutritivo , Perciformes , Compostos Orgânicos Voláteis/análise , Pirazinas/análise , Pirazinas/química , Alimentos Marinhos/análise
11.
Food Res Int ; 187: 114357, 2024 Jul.
Artigo em Inglês | MEDLINE | ID: mdl-38763641

RESUMO

The oxidation of fish lipids and proteins is interconnected. The LOX (lipoxygenase)-catalyzed LA (linoleic acid) oxidation system on MPs (myofibrillar proteins) was established in vitro, to investigate the impact of lipoxidation on the physicochemical properties of fish MPs. By detecting HNE (4-hydroxy-2-nonenal) concentration during LA oxidation, the HNE treatment system was established to investigate the role of HNE in this process. In addition, the site specificity of modification on MPs was detected utilizing LC-MS/MS. Both treatments could induce sidechain modification, increase particle size, and cause loss of nutritional value through the reduction in amino acid content of MPs. The HNE group is more likely to alter the MPs' surface hydrophobicity compared to the LA group. By increasing the exposure of modification sites in MPs, the HNE group has more types and number of modifications compared to the LA group. LA group mainly induced the modification of single oxygen addition on MPs instead, which accounted for over 50 % of all modifications. The LA group induced a more pronounced reduction in the solubility of MPs as compared to the HNE group. In conclusion, HNE binding had a high susceptibility to Lys on MPs. Protein aggregation, peptide chain fragmentation, and decreased solubility occurred in the LA group mainly induced by peroxide generated during lipid oxidation or the unreacted LA instead of HNE. This study fills in the mechanism of lipoxidation on protein oxidation in fish and sheds light on the HNE modification sites of MPs, paving the way for the development of oxidation control technology.


Assuntos
Aldeídos , Ácido Linoleico , Oxirredução , Espectrometria de Massas em Tandem , Aldeídos/metabolismo , Animais , Ácido Linoleico/química , Ácido Linoleico/metabolismo , Cromatografia Líquida/métodos , Proteínas de Peixes/metabolismo , Proteínas Musculares/metabolismo , Peixes , Interações Hidrofóbicas e Hidrofílicas , Lipoxigenase/metabolismo , Espectrometria de Massa com Cromatografia Líquida
12.
Food Res Int ; 187: 114398, 2024 Jul.
Artigo em Inglês | MEDLINE | ID: mdl-38763656

RESUMO

Nowadays, it is important to monitor the freshness of meat during storage to protect consumers' health. Volatile organic compounds (VOCs) are responsible for odour and taste of food, and they give an indication about meat quality and freshness. This study had the aim to seek and select potential new markers of meat spoilage through a semi-quantitative analysis in five types of meat (beef, raw and baked ham, pork sausage and chicken) and then to develop a new quantitative analytical method to detect and quantify potential markers on five types of meat simultaneously. Firstly, a new headspace-solid phase microextraction-gas chromatography-mass spectrometry (HS-SPME-GC-MS) method was developed to evaluate the volatile profile of five types of meat, preserved at 4 °C for 5 days. Among the 40 compounds identified, 15 were chosen and selected as potential shelf-life markers on the basis of their presence in most of meat samples or/and for their constant increasing/decreasing trend within the sample. Afterwards, a quantitative HS-SPME-GC-MS analytical method was developed to confirm which VOCs can be considered markers of shelf-life for these meat products, stored at 4 °C for 12 days. Some of the compounds analyzed attracted attention as they can be considered markers of shelf-life for at least 4 types of meat: 1-butanol, 3-methylbutanol, 1-hexanol, 2-nonanone, nonanal, 1-octen-3-ol and linalool. In conclusion, in this study a new quantitative HS-SPME-GC-MS analytical method to quantity 15 VOCs in five types of meat was developed and it was demonstrated that some of the compounds quantified can be considered markers of shelf-life for some of the meat products analyzed.


Assuntos
Armazenamento de Alimentos , Cromatografia Gasosa-Espectrometria de Massas , Produtos da Carne , Microextração em Fase Sólida , Compostos Orgânicos Voláteis , Compostos Orgânicos Voláteis/análise , Cromatografia Gasosa-Espectrometria de Massas/métodos , Microextração em Fase Sólida/métodos , Produtos da Carne/análise , Animais , Suínos , Odorantes/análise , Bovinos , Aldeídos/análise , Galinhas , Cetonas/análise , Pentanóis/análise , Monoterpenos Acíclicos/análise , Octanóis
13.
Int J Mol Sci ; 25(10)2024 May 20.
Artigo em Inglês | MEDLINE | ID: mdl-38791607

RESUMO

This work investigated the cocatalytic activity of recently prepared guanidinium salts containing an oxanorbornane subunit in an (S)-proline-catalyzed aldol reaction. The activity was interpreted by the diastereoselectivity of the reaction (anti/syn ratio) and for the most interesting polycyclic guanidinium salt, the enantioselectivity of the reaction was determined. The results indicated a negative impact on the oxanorbornane unit if present as the flexible substituent. For most of the tested aldehydes, the best cocatalysts provided enantioselectivities above 90% and above 95% at room temperature and 0 °C, respectively, culminating in >99.5% for 4-chloro- and 2-nitrobenzaldehyde as the substrate. The barriers for forming four possible enantiomers were calculated and the results for two anti-enantiomers are qualitatively consistent with the experiment. Obtained results suggest that the representatives of furfurylguanidinium and rigid polycyclic oxanorbornane-substituted guanidinium salts are good lead structures for developing new cocatalysts by tuning the chemical space around the guanidine moiety.


Assuntos
Guanidinas , Prolina , Catálise , Prolina/química , Guanidinas/química , Estereoisomerismo , Aldeídos/química , Norbornanos/química , Guanidina/química , Estrutura Molecular
14.
Chem Pharm Bull (Tokyo) ; 72(5): 507-511, 2024.
Artigo em Inglês | MEDLINE | ID: mdl-38811194

RESUMO

Amaryllidaceae alkaloids are structurally diverse natural products with a wide range biological properties, and based on the partial identification of the biosynthetic enzymes, norbelladine would be a common intermediate in the biosynthetic pathways. Previous studies suggested that norbelladine synthase (NBS) catalyzed the condensation reaction of 3,4-dihydroxybenzaldehyde and tyramine to form norcraugsodine, and subsequently, noroxomaritidine/norcraugsodine reductase (NR) catalyzed the nicotinamide adenine dinucleotide phosphate (NADPH)-dependent reduction of norcraugsodine to generate norbelladine. However, recent studies have highlighted possible alternative Amaryllidaceae alkaloid biosynthetic pathways via the formation of isovanillin and vanillin from the 4-O- and 3-O-methylation reactions of 3,4-dihydroxybenzaldehyde, respectively. Herein, we focused on NpsNBS and NpsNR, which were initially identified from Narcissus pseudonarcissus, and explored their substrate recognition tolerance by performing condensation reactions of tyramine with various benzaldehyde derivatives, to shed light on the Amaryllidaceae alkaloid biosynthetic pathway from the viewpoint of the enzymatic properties. The assays revealed that both NpsNBS and NpsNR lacked the abilities to produce 4'-O- and 3'-O-methylnorbelladine from isovanillin and vanillin with tyramine, respectively. These observations thus suggested that Amaryllidaceae alkaloids are biosynthesized from norbelladine, formed through the condensation/reduction reaction of 3,4-dihydroxybenzaldehyde with tyramine.


Assuntos
Aldeídos , Aldeídos/química , Aldeídos/metabolismo , Hidroxilação , Estrutura Molecular , Especificidade por Substrato , Nitrato Redutase/química , Nitrato Redutase/metabolismo
15.
Int J Mol Sci ; 25(10)2024 May 13.
Artigo em Inglês | MEDLINE | ID: mdl-38791326

RESUMO

Chronic environmental exposure to toxic heavy metals, which often occurs as a mixture through occupational and industrial sources, has been implicated in various neurological disorders, including Parkinsonism. Vanadium pentoxide (V2O5) typically presents along with manganese (Mn), especially in welding rods and high-capacity batteries, including electric vehicle batteries; however, the neurotoxic effects of vanadium (V) and Mn co-exposure are largely unknown. In this study, we investigated the neurotoxic impact of MnCl2, V2O5, and MnCl2-V2O5 co-exposure in an animal model. C57BL/6 mice were intranasally administered either de-ionized water (vehicle), MnCl2 (252 µg) alone, V2O5 (182 µg) alone, or a mixture of MnCl2 (252 µg) and V2O5 (182 µg) three times a week for up to one month. Following exposure, we performed behavioral, neurochemical, and histological studies. Our results revealed dramatic decreases in olfactory bulb (OB) weight and levels of tyrosine hydroxylase, dopamine, and 3,4-dihydroxyphenylacetic acid in the treatment groups compared to the control group, with the Mn/V co-treatment group producing the most significant changes. Interestingly, increased levels of α-synuclein expression were observed in the substantia nigra (SN) of treated animals. Additionally, treatment groups exhibited locomotor deficits and olfactory dysfunction, with the co-treatment group producing the most severe deficits. The treatment groups exhibited increased levels of the oxidative stress marker 4-hydroxynonenal in the striatum and SN, as well as the upregulation of the pro-apoptotic protein PKCδ and accumulation of glomerular astroglia in the OB. The co-exposure of animals to Mn/V resulted in higher levels of these metals compared to other treatment groups. Taken together, our results suggest that co-exposure to Mn/V can adversely affect the olfactory and nigral systems. These results highlight the possible role of environmental metal mixtures in the etiology of Parkinsonism.


Assuntos
Compostos de Manganês , Manganês , Camundongos Endogâmicos C57BL , Vanádio , Animais , Camundongos , Manganês/toxicidade , Vanádio/toxicidade , Masculino , Bulbo Olfatório/metabolismo , Bulbo Olfatório/efeitos dos fármacos , Bulbo Olfatório/patologia , Dopamina/metabolismo , Compostos de Vanádio , Estresse Oxidativo/efeitos dos fármacos , Transtornos Parkinsonianos/metabolismo , Transtornos Parkinsonianos/induzido quimicamente , alfa-Sinucleína/metabolismo , Cloretos/toxicidade , Cloretos/metabolismo , Tirosina 3-Mono-Oxigenase/metabolismo , Aldeídos/metabolismo , Substância Negra/metabolismo , Substância Negra/efeitos dos fármacos , Substância Negra/patologia , Modelos Animais de Doenças , Ácido 3,4-Di-Hidroxifenilacético/metabolismo
16.
Sci Rep ; 14(1): 10905, 2024 05 13.
Artigo em Inglês | MEDLINE | ID: mdl-38740939

RESUMO

Cancer-derived cell lines are useful tools for studying cellular metabolism and xenobiotic toxicity, but they are not suitable for modeling the biological effects of food contaminants or natural biomolecules on healthy colonic epithelial cells in a normal genetic context. The toxicological properties of such compounds may rely on their oxidative properties. Therefore, it appears to be necessary to develop a dual-cell model in a normal genetic context that allows to define the importance of oxidative stress in the observed toxicity. Given that the transcription factor nuclear factor erythroid 2-related factor 2 (Nrf2) is considered to be the master regulator of antioxidant defenses, our aim was to develop a cellular model comparing normal and Nrf2-depleted isogenic cells to qualify oxidative stress-related toxicity. We generated these cells by using the CRISPR/Cas9 technique. Whole-genome sequencing enabled us to confirm that our cell lines were free of cancer-related mutations. We used 4-hydroxy-2-nonenal (HNE), a lipid peroxidation product closely related to oxidative stress, as a model molecule. Here we report significant differences between the two cell lines in glutathione levels, gene regulation, and cell viability after HNE treatment. The results support the ability of our dual-cell model to study the role of oxidative stress in xenobiotic toxicity.


Assuntos
Células Epiteliais , Fator 2 Relacionado a NF-E2 , Estresse Oxidativo , Estresse Oxidativo/efeitos dos fármacos , Fator 2 Relacionado a NF-E2/metabolismo , Fator 2 Relacionado a NF-E2/genética , Animais , Camundongos , Células Epiteliais/metabolismo , Células Epiteliais/efeitos dos fármacos , Aldeídos/metabolismo , Glutationa/metabolismo , Sobrevivência Celular/efeitos dos fármacos , Linhagem Celular , Sistemas CRISPR-Cas , Peroxidação de Lipídeos/efeitos dos fármacos
17.
Int J Mol Sci ; 25(9)2024 May 06.
Artigo em Inglês | MEDLINE | ID: mdl-38732269

RESUMO

New antimicrobial molecules effective against Pseudomonas aeruginosa, known as an antibiotic-resistant "high-priority pathogen", are urgently required because of its ability to develop biofilms related to healthcare-acquired infections. In this study, for the first time, the anti-biofilm and anti-virulence activities of a polyphenolic extract of extra-virgin olive oil as well as purified oleocanthal and oleacein, toward P. aeruginosa clinical isolates were investigated. The main result of our study was the anti-virulence activity of the mixture of oleacein and oleocanthal toward multidrug-resistant and intermediately resistant strains of P. aeruginosa isolated from patients with ventilator-associated pneumonia or surgical site infection. Specifically, the mixture of oleacein (2.5 mM)/oleocanthal (2.5 mM) significantly inhibited biofilm formation, alginate and pyocyanin production, and motility in both P. aeruginosa strains (p < 0.05); scanning electron microscopy analysis further evidenced its ability to inhibit bacterial cell adhesion as well as the production of the extracellular matrix. In conclusion, our results suggest the potential application of the oleacein/oleocanthal mixture in the management of healthcare-associated P. aeruginosa infections, particularly in the era of increasing antimicrobial resistance.


Assuntos
Aldeídos , Antibacterianos , Biofilmes , Monoterpenos Ciclopentânicos , Azeite de Oliva , Fenóis , Pseudomonas aeruginosa , Biofilmes/efeitos dos fármacos , Biofilmes/crescimento & desenvolvimento , Pseudomonas aeruginosa/efeitos dos fármacos , Azeite de Oliva/química , Azeite de Oliva/farmacologia , Fenóis/farmacologia , Fenóis/química , Aldeídos/farmacologia , Aldeídos/química , Antibacterianos/farmacologia , Antibacterianos/química , Humanos , Testes de Sensibilidade Microbiana , Infecções por Pseudomonas/tratamento farmacológico , Infecções por Pseudomonas/microbiologia , Aderência Bacteriana/efeitos dos fármacos
18.
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
19.
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
20.
Sci Total Environ ; 931: 173024, 2024 Jun 25.
Artigo em Inglês | MEDLINE | ID: mdl-38719048

RESUMO

Among the problems caused by water eutrophication, the issue of odor compounds has attracted notable attention. ß-Cyclocitral, a widely distributed and versatile odor compound, is commonly derived from both algae and aquatic plants. Planting aquatic plants is a common method of water purification. However, there is limited study on their impact on ß-cyclocitral levels in water. Here, we conducted a study on the ß-cyclocitral levels in water and the submerged plant leaves under three nutrient levels and six plant density treatments. Our findings revealed the following: (1) Chlorophyll-a (Chla), ß-cyclocitral in the water (Wcyc), ß-cyclocitral in Potamogeton lucens leaves (Pcyc) and the biomass of the submerged plants increase with rising nutrient concentration, which increased about 83 %, 95 %, 450 %, 320 % from eutrophic treatment to oligotrophic treatment, respectively. (2) In water, ß-cyclocitral is influenced not only by algae but also by submerged plants, with primary influencing factors varying across different nutrient levels and plant densities. The main source of ß-cyclocitral in water becomes from plants to algae as the water eutrophication and plant density decrease. (3) As submerged plants have the capability to emit ß-cyclocitral, the release of ß-cyclocitral increases with the density of submerged plants. Hence, when considering planting submerged plants for water purification purposes, it is crucial to carefully manage submerged plant density to mitigate the risk of odor pollution emanating from aquatic plants. This study offers fresh insights into selecting optimal water density for submerged plants and their role in mitigating the release of ß-cyclocitral.


Assuntos
Eutrofização , Odorantes , Poluentes Químicos da Água , Odorantes/análise , Poluentes Químicos da Água/análise , Aldeídos/análise , Plantas , Nutrientes/análise , Monitoramento Ambiental , Diterpenos
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