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1.
J Hazard Mater ; 421: 126744, 2022 01 05.
Artigo em Inglês | MEDLINE | ID: mdl-34333408

RESUMO

To meet the rising global demand for water, it is necessary to develop membranes capable of efficiently purifying contaminated water sources. Herein, we report a series of novel polysulfone (PSf)/GO-vanillin nanofiltration membranes highly permeable, selective, and fouling resistant. The membranes are composed of two-dimensional (2D) graphite oxide (GO) layers embedded with vanillin as porogen and PSf as the base polymer. There is a growing interest in addressing the synergistic effect of GO and vanillin on improving the permeability and antifouling characteristics of membranes. Various spectroscopic and microscopic techniques were used to perform detailed physicochemical and morphological analyses. The optimized PSf16/GO0.15-vanillin0.8 membrane demonstrated 92.5% and 25.4% rejection rate for 2000 ppm magnesium sulphate (MgSO4) and sodium chloride (NaCl) solutions respectively. Antifouling results showed over 99% rejection for BSA and 93.57% flux recovery ratio (FRR). Experimental work evaluated the antifouling characteristics of prepared membranes to treat landfill leachate wastewater. The results showed 84-90% rejection for magnesium (Mg+2) and calcium (Ca+2) with 90.32 FRR. The study experimentally demonstrated that adding GO and vanillin to the polymeric matrix significantly improves fouling resistance and membrane performance. Future research will focus on molecular sieving for industrial separations and other niche applications using mixed matrix membranes.


Assuntos
Grafite , Purificação da Água , Benzaldeídos , Membranas Artificiais , Óxidos , Polímeros , Sulfonas
2.
J Colloid Interface Sci ; 605: 648-656, 2022 Jan.
Artigo em Inglês | MEDLINE | ID: mdl-34352445

RESUMO

Pancake-like TiO2 (M-TiO2) derived from the metal-organic framework was inlaid into three-dimensional flower-like BiOI through a facile solvothermal method. M-TiO2 supplies large surface area and mesoporous structure for attachment and transfer of the substrates and products, while BiOI acts as a photosensitizer to absorb visible light and generates electrons and holes. The distinct structure of M-TiO2/BiOI gives a favorable contact between the two monomers, and promotes the transfer of charge carriers. In conjunction with the proper band positions of M-TiO2 and BiOI, the efficient separation of electron-hole pairs is attained. Benefiting from the above cooperative effects of M-TiO2 and BiOI, the performance for the vanillin generation from sodium lignosulfonate (SLS) over M-TiO2/BiOI composites has a prominent improvement under visible light. Specifically, the yield over optimal M-TiO2/BiOI sample is about 5.8 mg/gSLS, obviously superior to that over pristine M-TiO2 (~1 mg/gSLS) and BiOI (~1.1 mg/gSLS). It is found that h+ and O2- play the key role for vanillin generation from sodium lignosulfonate, and the low vanillin generation under UV-vis light sheds light on that OH is an adverse factor. We hoped that this work could inspire the studies on the photocatalytic valorization of biomass using noble metal-free catalysts.


Assuntos
Bismuto , Estruturas Metalorgânicas , Benzaldeídos , Luz , Lignina/análogos & derivados , Sódio , Titânio
3.
J Hazard Mater ; 423(Pt A): 126525, 2022 02 05.
Artigo em Inglês | MEDLINE | ID: mdl-34246521

RESUMO

A complete hydrodeoxygenation(HDO) of vanillin to yield cycloalkanes was performed using bifunctional Ru loaded HZSM-5 catalysts with different metal loadings (0.1, 0.5, 1, 3, and 5 wt%) and Si/Al2 ratios (Si/Al2 = 23,300) in n-octane/water biphasic system. Both the reaction pathway and product distribution were influenced by the metal/acid balance of the catalysts. Higher metal/acid ratio promoted Caryl-C cleavage reaction, resulting in the increased yield of cyclohexane. Synergetic effect of metal and acid sites was observed in the bifunctional catalyst, attaining as high as 40-fold increase of metal efficiency in the ring hydrogenation reaction, compared to lone metal site catalyst. The effect of solvent composition was evaluated, revealing that the presence of water promoted the overall HDO reaction. By balancing metal/acid and introducing appropriate solvent system, efficient catalytic system that minimized carbon loss and improved metal efficiency for vanillin HDO was obtained.


Assuntos
Óleos Vegetais , Polifenóis , Benzaldeídos , Catálise
4.
Braz J Biol ; 83: e250550, 2021.
Artigo em Inglês | MEDLINE | ID: mdl-34730714

RESUMO

Vanillin is the major component which is responsible for flavor and aroma of vanilla extract and is produced by 3 ways: natural extraction from vanilla plant, chemical synthesis and from microbial transformation. Current research was aimed to study bacterial production of vanillin from native natural sources including sewage and soil from industrial areas. The main objective was vanillin bio-production by isolating bacteria from these native sources. Also to adapt methodologies to improve vanillin production by optimized fermentation media and growth conditions. 47 soil and 13 sewage samples were collected from different industrial regions of Lahore, Gujranwala, Faisalabad and Kasur. 67.7% bacterial isolates produced vanillin and 32.3% were non-producers. From these 279 producers, 4 bacterial isolates selected as significant producers were; A3, A4, A7 and A10. These isolates were identified by ribotyping as A3 Pseudomonas fluorescence (KF408302), A4 Enterococcus faecium (KT356807), A7 Alcaligenes faecalis (MW422815) and A10 Bacillus subtilis (KT962919). Vanillin producers were further tested for improved production of vanillin and were grown in different fermentation media under optimized growth conditions for enhanced production of vanillin. The fermentation media (FM) were; clove oil based, rice bran waste (residues oil) based, wheat bran based and modified isoeugenol based. In FM5, FM21, FM22, FM23, FM24, FM30, FM31, FM32, FM34, FM35, FM36, and FM37, the selected 4 bacterial strains produced significant amounts of vanillin. A10 B. subtilis produced maximum amount of vanillin. This strain produced 17.3 g/L vanillin in FM36. Cost of this fermentation medium 36 was 131.5 rupees/L. This fermentation medium was modified isoeugenol based medium with 1% of isoeugenol and 2.5 g/L soybean meal. ech gene was amplified in A3 P. fluorescence using ech specific primers. As vanillin use as flavor has increased tremendously, the bioproduction of vanillin must be focused.


Assuntos
Benzaldeídos , Aromatizantes , Alcaligenes faecalis/metabolismo , Bacillus subtilis/metabolismo , Benzaldeídos/metabolismo , Meios de Cultura , Enterococcus faecium/metabolismo , Fermentação , Aromatizantes/metabolismo , Microbiologia Industrial , Pseudomonas fluorescens/metabolismo
5.
Molecules ; 26(19)2021 Sep 23.
Artigo em Inglês | MEDLINE | ID: mdl-34641313

RESUMO

Aldehyde dehydrogenase 1A3 (ALDH1A3) has recently gained attention from researchers in the cancer field. Several studies have reported ALDH1A3 overexpression in different cancer types, which has been found to correlate with poor treatment recovery. Therefore, finding selective inhibitors against ALDH1A3 could result in new treatment options for cancer treatment. In this study, ALDH1A3-selective candidates were designed based on the physiological substrate resemblance, synthesized and investigated for ALDH1A1, ALDH1A3 and ALDH3A1 selectivity and cytotoxicity using ALDH-positive A549 and ALDH-negative H1299 cells. Two compounds (ABMM-15 and ABMM-16), with a benzyloxybenzaldehyde scaffold, were found to be the most potent and selective inhibitors for ALDH1A3, with IC50 values of 0.23 and 1.29 µM, respectively. The results also show no significant cytotoxicity for ABMM-15 and ABMM-16 on either cell line. However, a few other candidates (ABMM-6, ABMM-24, ABMM-32) showed considerable cytotoxicity on H1299 cells, when compared to A549 cells, with IC50 values of 14.0, 13.7 and 13.0 µM, respectively. The computational study supported the experimental results and suggested a good binding for ABMM-15 and ABMM-16 to the ALDH1A3 isoform. From the obtained results, it can be concluded that benzyloxybenzaldehyde might be considered a promising scaffold for further drug discovery aimed at exploiting ALDH1A3 for therapeutic intervention.


Assuntos
Aldeído Oxirredutases/antagonistas & inibidores , Benzaldeídos/síntese química , Inibidores Enzimáticos/síntese química , Neoplasias/enzimologia , Células A549 , Benzaldeídos/química , Benzaldeídos/farmacologia , Linhagem Celular Tumoral , Simulação por Computador , Descoberta de Drogas , Inibidores Enzimáticos/química , Inibidores Enzimáticos/farmacologia , Humanos , Concentração Inibidora 50 , Simulação de Acoplamento Molecular , Estrutura Molecular , Neoplasias/tratamento farmacológico
6.
Molecules ; 26(18)2021 Sep 13.
Artigo em Inglês | MEDLINE | ID: mdl-34577039

RESUMO

Products of natural origin remain important in the discovery of new bioactive molecules and are less damaging to the environment. Benzaldehyde is a product of the metabolism of plants, and similarly to oxygenated terpenes, it can have antibacterial activity against Staphylococcus aureus and toxic action against Drosophila melanogaster; we aimed to verify these activities. The broth microdilution tests determined the minimum inhibitory concentration (MIC) of benzaldehyde alone and in association with antibiotics and ethidium bromide (EtBr). Toxicity against Drosophila melanogaster was determined by fumigation tests that measured lethality and damage to the locomotor system. The results indicated that there was an association of norfloxacin and ciprofloxacin with benzaldehyde, from 64 µg/mL to 32 µg/mL of ciprofloxacin in the strain K6028 and from 256 µg/mL to 128 µg/mL of norfloxacin in the strain 1199B; however, the associations were not able to interfere with the functioning of the tested efflux pumps. In addition, benzaldehyde had a toxic effect on flies. Thus, the results proved the ability of benzaldehyde to modulate quinolone antibiotics and its toxic effects on fruit flies, thus enabling further studies in this area.


Assuntos
Antibacterianos , Benzaldeídos , Drosophila melanogaster , Animais , Testes de Sensibilidade Microbiana , Staphylococcus aureus/efeitos dos fármacos
7.
Int J Mol Sci ; 22(17)2021 Sep 04.
Artigo em Inglês | MEDLINE | ID: mdl-34502503

RESUMO

Cold-adapted enzymes are useful tools in the organic syntheses conducted in mixed aqueous-organic or non-aqueous solvents due to their molecular flexibility that stabilizes the proteins in low water activity environments. A novel psychrophilic laccase gene from Kabatiella bupleuri, G3 IBMiP, was spliced by Overlap-Extension PCR (OE-PCR) and expressed in Pichia pastoris. Purified recombinant KbLcc1 laccase has an optimal temperature of 30 °C and pH of 3.5, 5.5, 6.0, and 7.0 in the reaction with 2,2'-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS), guaiacol, sinapic acid, and syringaldazine, respectively. Moreover, laccase KbLcc1 is highly thermolabile, as it loses 40% of activity after 30 min at 40 °C and is inactivated at 50 °C after the same period of incubation. The new enzyme remained active with 1 mM of Ni2+, Cu2+, Mn2+, and Zn2+ and with 2 mM of Co2+, Ca2+, and Mg2+, but Fe2+ greatly inhibited the laccase activity. Moreover, 1% ethanol had no impact on KbLcc1, although acetone and ethyl acetate decreased the laccase activity. The presence of hexane (40%, v/v) caused a 58% increase in activity. Laccase KbLcc1 could be applied in the decolorization of synthetic dyes and in the biotransformation of ferulic acid to vanillin. After 5 days of reaction at 20 °C, pH 3.5, with 1 mM ABTS as a mediator, the vanillin concentration was 21.9 mg/L and the molar yield of transformation reached 14.39%.


Assuntos
Ascomicetos/enzimologia , Ascomicetos/metabolismo , Lacase/metabolismo , Benzaldeídos/metabolismo , Biotransformação/genética , Clonagem Molecular/métodos , Temperatura Baixa , Cor , Expressão Gênica/genética , Concentração de Íons de Hidrogênio , Cinética , Lacase/genética , Pichia/genética , Proteínas Recombinantes/genética , Proteínas Recombinantes/metabolismo
9.
Nat Commun ; 12(1): 4736, 2021 08 05.
Artigo em Inglês | MEDLINE | ID: mdl-34354056

RESUMO

Chromones represent a privileged scaffold in medicinal chemistry and are an omnipresent structural motif in natural products. Chemically encoded non-natural peptidomimetics feature improved stability towards enzymatic degradation, cell permeability and binding affinity, translating into a considerable impact on pharmaceutical industry. Herein, a strategy for the sustainable assembly of chromones via electro-formyl C-H activation is presented. The rational design of the rhodaelectro-catalysis is guided by detailed mechanistic insights and provides versatile access to tyrosine-based fluorogenic peptidomimetics.


Assuntos
Cromonas/química , Peptidomiméticos/química , Benzaldeídos/síntese química , Benzaldeídos/química , Biomimética/métodos , Catálise , Cromonas/síntese química , Técnicas Eletroquímicas , Estrutura Molecular , Oxirredução , Peptidomiméticos/síntese química
10.
Analyst ; 146(18): 5658-5667, 2021 Sep 13.
Artigo em Inglês | MEDLINE | ID: mdl-34382628

RESUMO

With the rapid development of various industries, cyanide (CN-) and hypochlorite (ClO-) have a tremendously adverse effect on the health of humans and animals. In this study, a fluorescent probe HHTB based on a benzaldehyde-indole fused chromophore was designed to detect cyanide and hypochlorite simultaneously. The synthesized probe was found to have strong anti-interference ability. In addition, the designed probe could respond rapidly to ClO- in just 80 s, while the color changed visibly from red to colorless. Moreover, the response time to CN- was longer (about 160 s), with the apparent color change from red to light red. The ratiometric and colorimetric absorbance variation of HHTB was due to the nucleophilic attack of CN- on the indole CN functional group and the strong oxidization of ClO- which destroyed the CC bonds and the conjugation systems. Furthermore, the probe HHTB responding to ClO- and CN- presented high sensitivity, as the calculated detection limits were 1.18 nM and 1.40 nM, respectively. The probe was also found to have low biological toxicity and was used in living cells successfully. Therefore, it has good application prospect in the field of cell imaging and biomedicine. The binding mechanism of HHTB-CN and the reaction mechanism of HHTB and ClO- were further elucidated by a series of experiments.


Assuntos
Corantes Fluorescentes , Ácido Hipocloroso , Animais , Benzaldeídos/toxicidade , Cianetos/toxicidade , Corantes Fluorescentes/toxicidade , Humanos , Ácido Hipocloroso/toxicidade , Indóis/toxicidade
11.
Molecules ; 26(15)2021 Jul 30.
Artigo em Inglês | MEDLINE | ID: mdl-34361791

RESUMO

As a key enzyme regulating postprandial blood glucose, α-Glucosidase is considered to be an effective target for the treatment of diabetes mellitus. In this study, a simple, rapid, and effective method for enzyme inhibitors screening assay was established based on α-glucosidase catalyzes reactions in a personal glucose meter (PGM). α-glucosidase catalyzes the hydrolysis of maltose to produce glucose, which triggers the reduction of ferricyanide (K3[Fe(CN)6]) to ferrocyanide (K4[Fe(CN)6]) and generates the PGM detectable signals. When the α-glucosidase inhibitor (such as acarbose) is added, the yield of glucose and the readout of PGM decreased accordingly. This method can achieve the direct determination of α-glucosidase activity by the PGM as simple as the blood glucose tests. Under the optimal experimental conditions, the developed method was applied to evaluate the inhibitory activity of thirty-four small-molecule compounds and eighteen medicinal plants extracts on α-glucosidase. The results exhibit that lithospermic acid (52.5 ± 3.0%) and protocatechualdehyde (36.8 ± 2.8%) have higher inhibitory activity than that of positive control acarbose (31.5 ± 2.5%) at the same final concentration of 5.0 mM. Besides, the lemon extract has a good inhibitory effect on α-glucosidase with a percentage of inhibition of 43.3 ± 3.5%. Finally, the binding sites and modes of four active small-molecule compounds to α-glucosidase were investigated by molecular docking analysis. These results indicate that the PGM method is feasible to screening inhibitors from natural products with simple and rapid operations.


Assuntos
Benzaldeídos/farmacologia , Benzofuranos/farmacologia , Glicemia/análise , Catecóis/farmacologia , Depsídeos/farmacologia , Diabetes Mellitus Tipo 2/diagnóstico , Inibidores de Glicosídeo Hidrolases/farmacologia , Monitorização Ambulatorial/métodos , alfa-Glucosidases/sangue , Acarbose/química , Acarbose/farmacologia , Benzaldeídos/química , Benzaldeídos/isolamento & purificação , Benzofuranos/química , Benzofuranos/isolamento & purificação , Sítios de Ligação , Técnicas Biossensoriais/instrumentação , Catecóis/química , Catecóis/isolamento & purificação , Depsídeos/química , Depsídeos/isolamento & purificação , Diabetes Mellitus Tipo 2/sangue , Diabetes Mellitus Tipo 2/tratamento farmacológico , Inibidores de Glicosídeo Hidrolases/química , Humanos , Hidrólise , Cinética , Maltose/metabolismo , Simulação de Acoplamento Molecular , Monitorização Ambulatorial/instrumentação , Extratos Vegetais/química , Plantas Medicinais , Ligação Proteica , Conformação Proteica em alfa-Hélice , Conformação Proteica em Folha beta , Domínios e Motivos de Interação entre Proteínas , Bibliotecas de Moléculas Pequenas/química , Bibliotecas de Moléculas Pequenas/farmacologia , Termodinâmica , Dispositivos Eletrônicos Vestíveis , alfa-Glucosidases/química
12.
Int J Pharm ; 607: 121047, 2021 Sep 25.
Artigo em Inglês | MEDLINE | ID: mdl-34450226

RESUMO

Carboxylation chitosan achieved by alkalization linked with ethyl vanillin to obtain Chitosan-ethyl vanillin (EV-CMCS) compound through Schiff base reaction and confirmed by FT-IR, UV, XRD, TG and NMR. EV-CMCS refluxed with GNRs for acquisition of EV-CMCS@GNRs nanocomposites for PTX Loading and release. Results demonstrated that both EV-CMCS and EV-CMCS@GNRs are nanoscale composites with excellent solubilization due to their micelle structure taking CMC values of 0.06683 mg/mL and 0.06537 mg/mL. It was found that the loading and encapsulation rate of EV-CMCS and EV-CMCS@GNRs for PTX are 19.59~37.64% and 60.36~80.79% as well as 20.99~37.02% and 58.78~79.77%. Compared with only the delayed release of EV-CMCS that it have 11.5% and 18.7% accumulative release amount for 24 h and 14.9% and 23.7% for 48 h under both pH 6.8 and 7.4, the EV-CMCS@GNRs represent sudden release that it have an accumulative release amount of 90.2% for 24 h and 96.0% for 48 h at pH 6.8. It deduced that the broken Schiff base under acidic condition can increase CMC of EV-CMCS@GNRs, which offered an alternative way for paclitaxel delivery for tumor therapy.


Assuntos
Quitosana , Nanocompostos , Benzaldeídos , Concentração de Íons de Hidrogênio , Paclitaxel , Espectroscopia de Infravermelho com Transformada de Fourier
13.
J Cachexia Sarcopenia Muscle ; 12(5): 1333-1351, 2021 10.
Artigo em Inglês | MEDLINE | ID: mdl-34427055

RESUMO

BACKGROUND: Cancer cachexia (CCx) is a multifactorial wasting disorder characterized by involuntary loss of body weight that affects many cancer patients and implies a poor prognosis, reducing both tolerance to and efficiency of anticancer therapies. Actual challenges in management of CCx remain in the identification of tumour-derived and host-derived mediators involved in systemic inflammation and tissue wasting and in the discovery of biomarkers that would allow for an earlier and personalized care of cancer patients. The aim of this study was to identify new markers of CCx across different species and tumour entities. METHODS: Quantitative secretome analysis was performed to identify specific factors characteristic of cachexia-inducing cancer cell lines. To establish the subsequently identified phospholipase PLA2G7 as a marker of CCx, plasma PLA2G7 activity and/or protein levels were measured in well-established mouse models of CCx and in different cohorts of weight-stable and weight-losing cancer patients with different tumour entities. Genetic PLA2G7 knock-down in tumours and pharmacological treatment using the well-studied PLA2G7 inhibitor darapladib were performed to assess its implication in the pathogenesis of CCx in C26 tumour-bearing mice. RESULTS: High expression and secretion of PLA2G7 were hallmarks of cachexia-inducing cancer cell lines. Circulating PLA2G7 activity was increased in different mouse models of CCx with various tumour entities and was associated with the severity of body wasting. Circulating PLA2G7 levels gradually rose during cachexia development. Genetic PLA2G7 knock-down in C26 tumours only partially reduced plasma PLA2G7 levels, suggesting that the host is also an important contributor. Chronic treatment with darapladib was not sufficient to counteract inflammation and tissue wasting despite a strong inhibition of the circulating PLA2G7 activity. Importantly, PLA2G7 levels were also increased in colorectal and pancreatic cancer patients with CCx. CONCLUSIONS: Overall, our data show that despite no immediate pathogenic role, at least when targeted as a single entity, PLA2G7 is a consistent marker of CCx in both mice and humans. The early increase in circulating PLA2G7 levels in pre-cachectic mice supports future prospective studies to assess its potential as biomarker for cancer patients.


Assuntos
Caquexia , Neoplasias Pancreáticas , 1-Alquil-2-acetilglicerofosfocolina Esterase , Animais , Benzaldeídos , Biomarcadores , Caquexia/tratamento farmacológico , Caquexia/etiologia , Humanos , Camundongos , Oximas , Estudos Prospectivos
14.
Microb Cell Fact ; 20(1): 151, 2021 Aug 03.
Artigo em Inglês | MEDLINE | ID: mdl-34344380

RESUMO

BACKGROUND: The aromatic compounds vanillin and vanillic acid are important fragrances used in the food, beverage, cosmetic and pharmaceutical industries. Currently, most aromatic compounds used in products are chemically synthesized, while only a small percentage is extracted from natural sources. The metabolism of vanillin and vanillic acid has been studied for decades in microorganisms and many studies have been conducted that showed that both can be produced from ferulic acid using bacteria. In contrast, the degradation of vanillin and vanillic acid by fungi is poorly studied and no genes involved in this metabolic pathway have been identified. In this study, we aimed to clarify this metabolic pathway in Aspergillus niger and identify the genes involved. RESULTS: Using whole-genome transcriptome data, four genes involved in vanillin and vanillic acid metabolism were identified. These include vanillin dehydrogenase (vdhA), vanillic acid hydroxylase (vhyA), and two genes encoding novel enzymes, which function as methoxyhydroquinone 1,2-dioxygenase (mhdA) and 4-oxo-monomethyl adipate esterase (omeA). Deletion of these genes in A. niger confirmed their role in aromatic metabolism and the enzymatic activities of these enzymes were verified. In addition, we demonstrated that mhdA and vhyA deletion mutants can be used as fungal cell factories for the accumulation of vanillic acid and methoxyhydroquinone from guaiacyl lignin units and related aromatic compounds. CONCLUSIONS: This study provides new insights into the fungal aromatic metabolic pathways involved in the degradation of guaiacyl units and related aromatic compounds. The identification of the involved genes unlocks new potential for engineering aromatic compound-producing fungal cell factories.


Assuntos
Aspergillus niger/genética , Aspergillus niger/metabolismo , Hidroquinonas/metabolismo , Lignina/metabolismo , Redes e Vias Metabólicas/genética , Ácido Vanílico/metabolismo , Aspergillus niger/enzimologia , Benzaldeídos/metabolismo , Hidroquinonas/química , Oxigenases de Função Mista , Ácido Vanílico/análise
15.
J Oleo Sci ; 70(8): 1109-1114, 2021.
Artigo em Inglês | MEDLINE | ID: mdl-34349087

RESUMO

In this study, we aimed to investigate imine emulsification using Raman spectroscopy with chemometrics. The imine emulsification samples were obtained by mixing aldehydes and amines in methanol and aqueous methanol. The Raman spectra of the samples were measured over time between 400 and 2300 cm-1 every 40 s using a Raman spectrometer. The obtained spectra were regarded as a dataset matrix. A multivariate curve resolution with alternating least squares was applied to the dataset. A multivariate analysis based on the Raman spectrum revealed that raw materials, emulsions, and products were decomposed when the water-rich samples were emulsified. Additionally, we evaluated the kinetics of the synthesis. The effect of water content on emulsification was investigated using Raman spectroscopy. The molecular dynamics of the co-solvent model were also investigated. The phase-layer construction was consistent with the phase transition in the water-methanol imine samples.


Assuntos
Benzaldeídos/química , Benzilaminas/química , Emulsões/síntese química , Bases de Schiff/síntese química , Metanol/química , Transição de Fase , Análise Espectral Raman , Água/química
16.
Molecules ; 26(12)2021 Jun 11.
Artigo em Inglês | MEDLINE | ID: mdl-34208150

RESUMO

Protocatechuic aldehyde (PCAL) and protocatechuic acid (PCAC) are catechol derivatives and have broad therapeutic effects associated with their antiradical activity. Their pharmacological and physicochemical properties have been improved via the cyclodextrin (CD) encapsulation. Because the characteristics of ß-CD inclusion complexes with PCAL (1) and PCAC (2) are still equivocal, we get to the bottom of the inclusion complexation by an integrated study of single-crystal X-ray diffraction and DFT full-geometry optimization. X-ray analysis unveiled that PCAL and PCAC are nearly totally shielded in the ß-CD wall. Their aromatic rings are vertically aligned in the ß-CD cavity such that the functional groups on the opposite side of the ring (3,4-di(OH) and 1-CHO/1-COOH groups) are placed nearby the O6-H and O2-H/O3-H rims, respectively. The preferred inclusion modes in 1 and 2 help to establish crystal contacts of OH⋅⋅⋅O H-bonds with the adjacent ß-CD OH groups and water molecules. By contrast, the DFT-optimized structures of both complexes in the gas phase are thermodynamically stable via the four newly formed host-guest OH⋯O H-bonds. The intermolecular OH⋅⋅⋅O H-bonds between PCAL/PCAC 3,4-di(OH) and ß-CD O6-H groups, and the shielding of OH groups in the ß-CD wall help to stabilize these antioxidants in the ß-CD cavity, as observed in our earlier studies. Moreover, PCAL and PCAC in distinct lattice environments are compared for insights into their structural flexibility.


Assuntos
Antioxidantes/química , Benzaldeídos/química , Catecóis/química , Hidroxibenzoatos/química , beta-Ciclodextrinas/química , Antioxidantes/administração & dosagem , Benzaldeídos/administração & dosagem , Catecóis/administração & dosagem , Cristalografia por Raios X , Sistemas de Liberação de Medicamentos/métodos , Ligação de Hidrogênio , Hidroxibenzoatos/administração & dosagem , Termodinâmica , beta-Ciclodextrinas/administração & dosagem
17.
Molecules ; 26(12)2021 Jun 12.
Artigo em Inglês | MEDLINE | ID: mdl-34204654

RESUMO

Vanilla (Vanilla planifolia) is a precious natural flavoring that is commonly used throughout the world. In the past, all vanilla used in Taiwan was imported; however, recent breakthroughs in cultivation and processing technology have allowed Taiwan to produce its own supply of vanilla. In this study, headspace solid-phase microextraction (HS-SPME) combined with GC-FID and GC-MS was used to analyze the volatile components of vanilla from different origins produced in Taiwan under different cultivation and processing conditions. The results of our study revealed that when comparing different harvest maturities, the composition diversity and total volatile content were both higher when the pods were matured for more than 38 weeks. When comparing different killing conditions, we observed that the highest vanillin percentage was present after vanilla pods were killed three times in 65 °C treatments for 1 min each. From the experiment examining the addition of different strains, the PCA results revealed that the volatiles of vanilla that was processed with Dekkera bruxellensis and Bacillus subtilis was clearly distinguished from which obtained by processing with the other strains. Vanilla processed with B. subtilis contained 2-ethyl-1-hexanol, and this was not detected in other vanillas. Finally, when comparing the vanillin percentage from seven different regions in Taiwan, vanilla percentage from Taitung and Taoyuan Longtan were the highest.


Assuntos
Vanilla/química , Vanilla/metabolismo , Compostos Orgânicos Voláteis/química , Agricultura/métodos , Benzaldeídos/química , Benzaldeídos/isolamento & purificação , Cromatografia Gasosa/métodos , Aromatizantes/análise , Cromatografia Gasosa-Espectrometria de Massas/métodos , Extratos Vegetais/análise , Microextração em Fase Sólida/métodos , Taiwan , Compostos Orgânicos Voláteis/análise
18.
J Food Sci ; 86(8): 3645-3657, 2021 Aug.
Artigo em Inglês | MEDLINE | ID: mdl-34287910

RESUMO

To better control the quality of synthetic vanillin obtained by using the guaiacol synthesis method, the olfactory impacts of byproducts on the aroma of the synthetic vanillin samples were evaluated and their optimum concentration ranges were determined. Four byproducts (guaiacol, ortho-vanillin, 5-methyl-vanillin, and 5-formyl-vanillin) were identified by gas chromatography-mass spectrometry (GC-MS) and quantified by gas chromatography-flame ionization detection (GC-FID) in the synthetic vanillin samples with different degrees of purity. The aroma intensities (AIs) of the four byproducts obtained by gas chromatography-olfactometry (GC-O) were: guaiacol (AI: 3.5-4.0, smoke), ortho-vanillin (AI: 1.6-2.5, almond), 5-methyl-vanillin (AI: 2.5-3.3, aldehyde), and 5-formyl-vanillin (AI: 3.2-3.8, green). The aroma perceptual interactions of the four byproducts and the vanillin in the synthetic vanillin samples were determined by S-curve analysis. Guaiacol and 5-methyl-vanillin showed synergistic effects by Feller's additive model. Combined with the results of an addition experiment, when the contents of guaiacol, ortho-vanillin, 5-methyl-vanillin, and 5-formyl-vanillin were within 50, 10, 400, and 1,000 mg/kg respectively, the byproducts had no effects on the aroma quality of the synthetic vanillin samples. PRACTICAL APPLICATION: Synthetic vanillin is one of the most commonly used food additives. Currently, the purity of synthetic vanillin can reach 99.9%, but trace byproducts are still present. Continuing to improve the purity of synthetic vanillin will significantly increase its production costs. Therefore, it is necessary to determine whether the presence of these byproducts affects the aroma quality of the synthetic vanillin samples or not. If they have a negative effect on its aroma, it will be important to reduce their content. If they have no influence or positive role, there is no need to control the content of these byproducts to very low levels. This study determined the content of the byproducts produced during the synthesis of vanillin by guaiacol glyoxylic acid method, judged the perceptual interaction between the byproducts and the vanillin in the synthetic vanillin samples, and determined the optimum range within which the byproducts had no effects on the aroma quality. This study provides a theoretical basis for improving the aroma quality of synthetic vanillin while controlling the production costs.


Assuntos
Guaiacol , Compostos Orgânicos Voláteis , Benzaldeídos , Cromatografia Gasosa-Espectrometria de Massas , Odorantes/análise , Olfatometria , Compostos Orgânicos Voláteis/análise
19.
Biomed Res Int ; 2021: 6108999, 2021.
Artigo em Inglês | MEDLINE | ID: mdl-34327232

RESUMO

Protocatechualdehyde (PCA), an important component of Salvia miltiorrhiza, has many activities, such as anti-inflammatory and antisepsis activities. However, the role of PCA in osteoclasts is not clear. We used RAW264.7 cells (a mouse leukemic monocyte/macrophage cell line) and bone marrow macrophages (BMMs) to probe the role of PCA in osteoclasts and the underlying mechanism. The effects of PCA on cell activity were evaluated with CCK-8 assays. TRAP staining detected mature osteoclasts. Corning Osteo Assay Surface plates were used to examine absorption. The levels of RNA and protein were analyzed, respectively, using RT-PCR and Western blotting. PCA (5 µg/ml) was not toxic to the two cell types but reduced the formation of osteoclasts and bone absorption. Furthermore, PCA restrained the expression of mRNAs encoding proteins associated with osteoclasts and reduced the phosphorylation of proteins in important signaling pathways. The results indicate that PCA inhibits osteoclast differentiation by suppressing NF-κB and MAPK activity.


Assuntos
Benzaldeídos/farmacologia , Catecóis/farmacologia , Diferenciação Celular/efeitos dos fármacos , Macrófagos/citologia , Macrófagos/enzimologia , Proteínas Quinases Ativadas por Mitógeno/metabolismo , NF-kappa B/metabolismo , Osteoclastos/citologia , Osteoclastos/enzimologia , Actinas/metabolismo , Animais , Apoptose/efeitos dos fármacos , Biomarcadores/metabolismo , Regulação da Expressão Gênica/efeitos dos fármacos , Sistema de Sinalização das MAP Quinases/efeitos dos fármacos , Macrófagos/efeitos dos fármacos , Masculino , Camundongos , Camundongos Endogâmicos BALB C , Osteoclastos/efeitos dos fármacos , Ligante RANK/farmacologia , Células RAW 264.7 , RNA Mensageiro/genética , RNA Mensageiro/metabolismo
20.
Am J Physiol Heart Circ Physiol ; 321(2): H400-H411, 2021 08 01.
Artigo em Inglês | MEDLINE | ID: mdl-34213392

RESUMO

Therapeutic agents that increase the Hb affinity for oxygen (O2) could, in theory, lead to decreased O2 release from Hb and impose a hypoxic risk to tissues. In this study, GBT1118, an allosteric modifier of Hb affinity for O2, was used to assess the impact of increasing Hb affinity for O2 on brain tissue oxygenation, blood pressure, heart rate, O2 delivery, and tolerance to hypoxia in Townes transgenic sickle cell disease (SCD) mice. Brain oxygenation and O2 delivery were studied during normoxia and severe hypoxic challenges. Chronic treatment with GBT1118 increased Hb affinity for O2, reducing the Po2 for 50% HbO2 saturation (P50) in SCD mice from 31 mmHg to 18 mmHg. This treatment significantly reduced anemia, increasing hematocrit by 33%, improved cardiac output (CO), and O2 delivery and extraction. Chronically increasing Hb affinity for O2 with GBT1118 preserved cortical O2 tension during normoxia, improved cortical O2 tension during hypoxia, and increased tolerance to severe hypoxia in SCD mice. Independent of hematological changes induced by chronic treatment, a single dose of GBT1118 significantly improved tolerance to hypoxia, highlighting the benefits of increasing Hb affinity for O2 and consequently reducing sickling of RBCs in blood during hypoxia in SCD.NEW & NOTEWORTHY Chronic pharmacologically increased hemoglobin affinity for oxygen in sickle cell disease mice alleviated hematological consequences of sickle cell disease, increasing RBC half-life, hematocrit, and hemoglobin concentration, while also decreasing reticulocyte count. Additionally, chronically increased hemoglobin affinity for oxygen significantly improved survival as well as cortical tissue oxygenation in sickle cell disease mice during hypoxia, suggesting that oxygen delivery and utilization is improved by increased hemoglobin affinity for oxygen.


Assuntos
Anemia Falciforme/metabolismo , Benzaldeídos/farmacologia , Córtex Cerebral/metabolismo , Eritrócitos/efeitos dos fármacos , Fármacos Hematológicos/farmacologia , Hemoglobina Falciforme/efeitos dos fármacos , Hipóxia/metabolismo , Niacinamida/análogos & derivados , Oxigênio/metabolismo , Regulação Alostérica , Animais , Encéfalo/metabolismo , Modelos Animais de Doenças , Hematócrito , Hemoglobina Falciforme/metabolismo , Camundongos , Camundongos Transgênicos , Niacinamida/farmacologia , Pressão Parcial
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