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1.
Food Chem ; 367: 130659, 2022 Jan 15.
Artigo em Inglês | MEDLINE | ID: mdl-34343800

RESUMO

This study presents a sensitive approach for electrochemical determination of 5-hydroxymethylfurfural (5-HMF) in food. The electrochemical sensor was fabricated on a copper electrode (CuE) modified with co-electrodeposited Cu-Ni bimetallic particles. This sensor, fabricated by 30 cycles of cyclic voltametric scanning with a scan rate of 50 mV s-1, exhibits good electrocatalytic ability to 5-HMF oxidation. Under the optimal conditions, linear scan voltammetry (LSV) and chronoamperometry were conducted for the determination of 5-HMF. The results of LSV show that a linear dependency within the 0.4-10 mM range with a detection limit (LOD) of 3.51 µM (S/N = 3) was achieved, while a linear range in 1 × 10-4-11 mM with a LOD of 0.043 µM (S/N = 3) was obtained by chronoamperometric measurement. The electrochemical sensor was finally applied in determination of 5-HMF in various foods, and the reliability and accuracy of the method were assessed by adopting an UV method as a standard method. Results show that the concentrations of 5-HMF in real samples are close to those measured by the standard method. In addition, standard addition method was further performed to evaluate the accuracy of our approach. The recoveries ranged from 90.0% to 110.0% are calculated, demonstrating good accuracy of the electrochemical sensor.


Assuntos
Cobre , Técnicas Eletroquímicas , Eletrodos , Furaldeído/análogos & derivados , Limite de Detecção , Reprodutibilidade dos Testes
2.
Food Chem ; 368: 130814, 2022 Jan 30.
Artigo em Inglês | MEDLINE | ID: mdl-34428689

RESUMO

Furfural compounds are produced during infant formula production when heat treatment is involved. In this study, a robust method was established for determining potential and free furfural compounds (furfural, 5-methyl-2-furfural, 2-acetylfuran and 5-hydroxymethyl-2-furfural) using a modified QuEChERS technique coupled with GC-MS/MS. Further, 36 samples of two batches, covering the whole infant formula production chain were analyzed by the method to investigate how furfurals evolved during process. Then risk assessment was conducted using the Toxtree and T.E.S.T. software and evaluated by hazard quotient. Results showed the contents of bound and free 5-hydroxymethyl-2-furfural demonstrated largest increase during spray-drying (6-11 times) and homogenization stages (12-33 times), respectively. As the sum up of bound and free 5-hydroxymethyl-2-furfural, potential 5-hydroxymethyl-2-furfural was found can cause safety risks in the production chain due to the high hazard quotient value (3.11), indicating it should be controlled in homogenization and spray-drying stages.


Assuntos
Furaldeído , Fórmulas Infantis , Furaldeído/análise , Humanos , Medição de Risco , Espectrometria de Massas em Tandem
3.
Food Chem ; 370: 131271, 2022 Feb 15.
Artigo em Inglês | MEDLINE | ID: mdl-34788952

RESUMO

5-Hydroxymethylfurfural (HMF) and acrylamide (AA) are neoformed food contaminants. In this study, the simultaneous inhibition of HMF and AA by histidine (His) were investigated. In the asparagine (Asn)/glucose (Glc) model system, the inhibition ratios of HMF and AA were in the range of 28-58% and 0-71% when 20 mmol/L His was added. In cookies, His also exhibited excellent inhibition effects on both HMF and AA. At the His concentration of 2% (w/w), the inhibition ratios of HMF and AA reached 90% and 65%. Additionally, the sensory quality of cookies was not affected significantly. Qualitative results suggested that His inhibited the formation of AA by the competitive reaction between His and Asn for Glc, as well as directly eliminated the formed HMF and AA via the carbonyl-amine reaction and the Michael addition, respectively. This study revealed that His could be applied for the inhibition of HMF and AA in heated food.


Assuntos
Acrilamida , Histidina , Asparagina , Furaldeído/análogos & derivados
4.
Food Chem ; 369: 130944, 2022 Feb 01.
Artigo em Inglês | MEDLINE | ID: mdl-34464834

RESUMO

A headspace-solid phase microextraction - gas chromatography-flame ionisation detector (HS-SPME-GC/FID) method was developed for the simultaneous determination of furan, 2-methylfuran and 2-furaldehyde in thermally processed Mopane worms, corn, and peanuts. The optimal HS-SPME conditions with polydimethylsiloxane/carboxen/divinylbenzene (PDMS/CAR/DVB) fiber were 30 °C, 40 min and 600 rpm stirring speed. The recoveries, detection and quantification limits for the analytes in food samples were 67-106%, 0.54-3.5 µg kg-1, and 1.8-12 µg kg-1, respectively. These results showed that the developed method was accurate, reproducible, and sensitive for the determination of furan, 2-methylfuran and 2-furaldehyde in complex food matrices with limited interference from other components. The optimised analytical method was applied for monitoring the presence of the furanic compounds in heat-processed South African foods. Although 2-furaldehyde was not detected in food samples, the maximum concentrations of 24 and 95 µg kg-1 were found for furan and 2-methylfuran, respectively.


Assuntos
Microextração em Fase Sólida , Zea mays , Arachis , Cromatografia Gasosa , Furaldeído , Reprodutibilidade dos Testes
5.
Food Chem ; 371: 131155, 2022 Mar 01.
Artigo em Inglês | MEDLINE | ID: mdl-34571410

RESUMO

The volatile products (VPs) formation from the self-degradation of l-ascorbic acid (ASA) in hot compressed water (HCW) was investigated with different reaction parameters, such as time, temperature, pH and ratio of ASA/water. The results showed that various reaction parameters had varying degrees of influence on the reaction, while the most significant effect factor was the initial pH of the solution. Furfural was the major product under acidic conditions, while furan derivatives were the main products under alkaline conditions. The above results showed that pH played the dominant role for yields and distribution of VPs in HCW. In the HCW system, the yields and classifications of VPs and conversion rate of ASA were not the same as those of VPs and ASA under traditional conditions. Based on the experimental results, the possible formation mechanism of VPs from the self-degradation of ASA was proposed in HCW.


Assuntos
Temperatura Alta , Água , Ácido Ascórbico , Furaldeído , Temperatura
6.
Food Chem ; 371: 131154, 2022 Mar 01.
Artigo em Inglês | MEDLINE | ID: mdl-34598120

RESUMO

The influence of acidity regulators and buffers on the formation of acrylamide (AA) and 5-hydroxymethylfurfural (5-HMF) in French fries and the underlying mechanism were evaluated. Prior to frying, the potato strips were dipped in the corresponding acidity regulator solutions or buffers for 30 min at room temperature. The results showed that acids inhibited AA formation, but increased 5-HMF levels. The AA level decreased and 5-HMF level increased with decreasing pH of potato strips. Interestingly, increasing concentration of acid radical ions resulted in AA increase and 5-HMF decrease, which was opposite to the acidification effect of citric acid and acetic acid. Both pH and acid radical ion were important factors for AA and 5-HMF formation. Moreover, acidity regulators might impact AA formation by acting on the generation of methylglyoxal (MGO) and glyoxal (GO) and impact 5-HMF formation by acting on the generation of 3-deoxyglucosone (3-DG).


Assuntos
Acrilamida , Solanum tuberosum , Furaldeído/análogos & derivados , Temperatura Alta , Concentração de Íons de Hidrogênio , Íons
7.
Chemosphere ; 287(Pt 1): 132114, 2022 Jan.
Artigo em Inglês | MEDLINE | ID: mdl-34481171

RESUMO

The adsorption techniques are extensively used in dyes, metronidazole, aniline, wastewater treatment methods to remove certain pollutants. Furfural is organic in nature, considered a pollutant having a toxic effect on humans and their environment and especially aquatic species. Due to distinct characteristics of the adsorption technique, this technique can be utilized to adsorb furfural efficiently. As an environmentally friendly technique, the pomegranate peel was used to synthesized activated carbon and nanostructure of zerovalent iron impregnated on the synthesized activated carbon. The physicochemical and crystallinity characterization was done using Fourier transmission infrared spectroscopy (FTIR), X-ray diffraction (XRD), Brunauer-Emmett-Teller (BET), and Field emission scanning electron microscopy (FESEM). The nanoparticles are porous in structure having 821.74 m2/g specified surface area. The maximum amount of the adsorbent pores in the range of 3.08 nm shows the microporous structure and enhancement in adsorption capacity. The effects of increment in concentration of adsorbent, pH, reaction contact time and adsorbent dose, isothermal and kinetic behaviour were investigated. At the UV wavelength of 227 nm furfural adsorption was detected. The separation of the furfural from the aqueous solution was calculated at the 1 h reaction time at the composite dosage of 4 g/L, 250 mg/L adsorbent concentration and pH kept at 7. The 81.87% is the maximum removal attained by the nanocomposite in comparison to the activated carbon is 62.06%. Furfural adsorption was also analyzed by using the equations of isothermal and kinetics models. The adsorption process analysis depends on the Freundlich isotherm and Intra-particle diffusion than the other models. The maximum adsorbent of the composite was determined by the Langmuir model which is 222.22 mg/g. The furfural removal enhances as the adsorbent dose enhances. The developed zerovalent iron nanoparticles incorporated on activated carbon (AC/nZVI) from pomegranate peel extract are feasible as an efficient and inexpensive adsorbent to eliminate furfural from a liquid solution.


Assuntos
Nanopartículas , Poluentes Químicos da Água , Adsorção , Carvão Vegetal , Furaldeído , Humanos , Ferro , Cinética , Espectroscopia de Infravermelho com Transformada de Fourier , Poluentes Químicos da Água/análise
8.
J Sci Food Agric ; 102(1): 250-258, 2022 Jan 15.
Artigo em Inglês | MEDLINE | ID: mdl-34091922

RESUMO

BACKGROUND: Sesame oil has an excellent flavor and is widely appreciated. It has a higher price than other vegetable oils because of the high price of its raw materials, and different processing techniques also result in products of different quality levels, which can command different prices. In the market, there is a persistent problem of adulteration of sesame oil, driven by economic interests. The screening of volatile markers used to distinguish the authenticity of sesame oil raw materials and production processes is therefore very important. RESULTS: In this work, six markers related to the production processes and raw materials of sesame oil were screened by gas chromatography-tandem mass spectrometry (GC-MS/MS) combined with chemometric analysis. They were 3-methyl-2-butanone, 2-ethyl-5-methyl-pyrazine, guaiacol, 2,6-dimethyl-pyrazine, 5-methyl furfural, and ethyl-pyrazine. The concentration of these markers in sesame oil is between 10 and1000 times that found in other vegetable oils. However, only 3-methyl-2-butanone and 2-ethyl-5-methyl-pyrazine differed significantly as the result of the use of different production processes. Except for guaiacol, which was mainly derived from raw materials, the other five compounds mentioned above all result from the Maillard reaction during thermal processing. The six compounds mentioned above are sufficient to distinguish fraud involving sesame oil raw materials and production processes, and can identify accurately adulteration levels of 30% concentration. CONCLUSION: In this study, the classification markers can identify the adulteration of sesame oil accurately. These six compounds are therefore important for the authenticity of sesame oil and provide a theoretical basis for the rapid and accurate identification of the authenticity of sesame oil. © 2021 Society of Chemical Industry.


Assuntos
Contaminação de Alimentos/análise , Produtos Finais de Glicação Avançada/análise , Guaiacol/análise , Óleo de Gergelim/análise , Aromatizantes/análise , Furaldeído/análise , Cromatografia Gasosa-Espectrometria de Massas , Reação de Maillard
9.
Appl Microbiol Biotechnol ; 105(21-22): 8313-8327, 2021 Nov.
Artigo em Inglês | MEDLINE | ID: mdl-34643786

RESUMO

The development of enzymatic processes for the environmentally friendly production of 2,5-furandicarboxylic acid (FDCA), a renewable precursor for bioplastics, from 5-hydroxymethylfurfural (HMF) has gained increasing attention over the last years. Aryl-alcohol oxidases (AAOs) catalyze the oxidation of HMF to 5-formyl-2-furancarboxylic acid (FFCA) through 2,5-diformylfuran (DFF) and have thus been applied in enzymatic reaction cascades for the production of FDCA. AAOs are flavoproteins that oxidize a broad range of benzylic and aliphatic allylic primary alcohols to the corresponding aldehydes, and in some cases further to acids, while reducing molecular oxygen to hydrogen peroxide. These promising biocatalysts can also be used for the synthesis of flavors, fragrances, and chemical building blocks, but their industrial applicability suffers from low production yield in natural and heterologous hosts. Here we report on heterologous expression of a new aryl-alcohol oxidase, MaAAO, from Moesziomyces antarcticus at high yields in the methylotrophic yeast Pichia pastoris (recently reclassified as Komagataella phaffii). Fed-batch fermentation of recombinant P. pastoris yielded around 750 mg of active enzyme per liter of culture. Purified MaAAO was highly stable at pH 2-9 and exhibited high thermal stability with almost 95% residual activity after 48 h at 57.5 °C. MaAAO accepts a broad range of benzylic primary alcohols, aliphatic allylic alcohols, and furan derivatives like HMF as substrates and some oxidation products thereof like piperonal or perillaldehyde serve as building blocks for pharmaceuticals or show health-promoting effects. Besides this, MaAAO oxidized 5-hydroxymethyl-2-furancarboxylic acid (HMFCA) to FFCA, which has not been shown for any other AAO so far. Combining MaAAO with an unspecific peroxygenase oxidizing HMFCA to FFCA in one pot resulted in complete conversion of HMF to FDCA within 144 h. MaAAO is thus a promising biocatalyst for the production of precursors for bioplastics and bioactive compounds. KEY POINTS: • MaAAO from M. antarcticus was expressed in P. pastoris at 750 mg/l. • MaAAO oxidized 5-hydroxymethyl-2-furancarboxylic acid (HMFCA). • Complete conversion of HMF to 2,5-furandicarboxylic acid by combining MaAAO and UPO.


Assuntos
Furaldeído , Oxirredutases do Álcool , Basidiomycota , Furanos , Oxirredução , Saccharomycetales
10.
PLoS Genet ; 17(10): e1009826, 2021 10.
Artigo em Inglês | MEDLINE | ID: mdl-34624020

RESUMO

Development of cell factories for conversion of lignocellulosic biomass hydrolysates into biofuels or bio-based chemicals faces major challenges, including the presence of inhibitory chemicals derived from biomass hydrolysis or pretreatment. Extensive screening of 2526 Saccharomyces cerevisiae strains and 17 non-conventional yeast species identified a Candida glabrata strain as the most 5-hydroxymethylfurfural (HMF) tolerant. Whole-genome (WG) transformation of the second-generation industrial S. cerevisiae strain MD4 with genomic DNA from C. glabrata, but not from non-tolerant strains, allowed selection of stable transformants in the presence of HMF. Transformant GVM0 showed the highest HMF tolerance for growth on plates and in small-scale fermentations. Comparison of the WG sequence of MD4 and GVM1, a diploid segregant of GVM0 with similarly high HMF tolerance, surprisingly revealed only nine non-synonymous SNPs, of which none were present in the C. glabrata genome. Reciprocal hemizygosity analysis in diploid strain GVM1 revealed AST2N406I as the only causative mutation. This novel SNP improved tolerance to HMF, furfural and other inhibitors, when introduced in different yeast genetic backgrounds and both in synthetic media and lignocellulose hydrolysates. It stimulated disappearance of HMF and furfural from the medium and enhanced in vitro furfural NADH-dependent reducing activity. The corresponding mutation present in AST1 (i.e. AST1D405I) the paralog gene of AST2, also improved inhibitor tolerance but only in combination with AST2N406I and in presence of high inhibitor concentrations. Our work provides a powerful genetic tool to improve yeast inhibitor tolerance in lignocellulosic biomass hydrolysates and other inhibitor-rich industrial media, and it has revealed for the first time a clear function for Ast2 and Ast1 in inhibitor tolerance.


Assuntos
Antifúngicos/farmacologia , Farmacorresistência Fúngica/genética , Tolerância a Medicamentos/genética , Furaldeído/análogos & derivados , Mutação/genética , Saccharomyces cerevisiae/genética , Transformação Genética/genética , Biomassa , Fermentação/genética , Furaldeído/farmacologia , Saccharomyces cerevisiae/efeitos dos fármacos , Proteínas de Saccharomyces cerevisiae/genética
11.
Nutrients ; 13(10)2021 Sep 29.
Artigo em Inglês | MEDLINE | ID: mdl-34684449

RESUMO

5-Hydroxymethylfurfural (5-HMF) is known to increase hemoglobin oxygen affinity (Hb-O2 affinity) and to induce a left shift of the oxygen dissociation curve (ODC). It is under investigation as a therapeutic agent in sickle cell anemia and in conditions where pulmonary oxygen uptake is deteriorated or limited (e.g., various clinical conditions or altitude exposure). The combination of 5-HMF and α-ketoglutaric acid (αKG) is commercially available as a nutritional supplement. To further elucidate dose effects, ODCs were measured in vitro in venous whole blood samples of 20 healthy volunteers (10 female and 10 male) after the addition of three different doses of 5-HMF, αKG and the combination of both. Linear regression analysis revealed a strong dose-dependent increase in Hb-O2 affinity for 5-HMF (R2 = 0.887; p < 0.001) and the commercially available combination with αKG (R2 = 0.882; p < 0.001). αKG alone increased Hb-O2 affinity as well but to a lower extent. Both the combination (5-HMF + αKG) and 5-HMF alone exerted different P50 and Hill coefficient responses overall and between sexes, with more pronounced effects in females. With increasing Hb-O2 affinity, the sigmoidal shape of the ODC was better preserved by the combination of 5-HMF and αKG than by 5-HMF alone. Concerning the therapeutic effects of 5-HMF, this study emphasizes the importance of adequate dosing in various physiological and clinical conditions, where a left-shifted ODC might be beneficial. By preserving the sigmoidal shape of the ODC, the combination of 5-HMF and αKG at low (both sexes) and medium (males only) doses might be able to better maintain efficient oxygen transport, particularly by mitigating potentially deteriorated oxygen unloading in the tissue. However, expanding knowledge on the interaction between 5-HMF and Hb-O2 affinity in vitro necessitates further investigations in vivo to additionally assess pharmacokinetic mechanisms.


Assuntos
Furaldeído/análogos & derivados , Hemoglobinas/metabolismo , Ácidos Cetoglutáricos/farmacologia , Micronutrientes/farmacologia , Oxigênio/metabolismo , Adulto , Análise de Variância , Relação Dose-Resposta a Droga , Eritrócitos/efeitos dos fármacos , Eritrócitos/metabolismo , Feminino , Furaldeído/administração & dosagem , Furaldeído/farmacologia , Humanos , Ácidos Cetoglutáricos/administração & dosagem , Masculino , Micronutrientes/administração & dosagem , Ligação Proteica/efeitos dos fármacos , Fatores Sexuais , Adulto Jovem
12.
J Agric Food Chem ; 69(43): 12807-12817, 2021 Nov 03.
Artigo em Inglês | MEDLINE | ID: mdl-34672546

RESUMO

Glycation and caramelization reactions in malt lead to the formation of 1,2-dicarbonyl compounds, which come in contact with yeast during fermentation. In the present study, the metabolic fate of 5-hydroxymethylfurfural (HMF) and 1,2-dicarbonyl compounds (3-deoxyglucosone, 3-deoxygalactosone, 3-deoxypentosone, 3,4-dideoxyglucosone-3-ene) was assessed in the presence of Saccharomyces cerevisiae. HMF is degraded very fast by yeast with the formation of 2,5-bis(hydroxymethyl)furan (BHMF). By contrast, only 7-30% of 250 µM dicarbonyl compounds is degraded within 48 h. The respective deoxyketoses, 3-deoxyfructose (3-DF), 3-deoxytagatose, 3-deoxypentulose, and 3,4-dideoxyfructose, were identified as metabolites. While 17.8% of 3-deoxyglucosone was converted to 3-deoxyfructose, only about 0.1% of 3-deoxypentosone was converted to 3-deoxypentulose during 48 h. Starting with the parent dicarbonyl compounds, the synthesis of all deoxyketose metabolites was achieved by applying a metal-catalyzed reduction in the presence of molecular hydrogen. In a small set of commercial beer samples, BHMF and all deoxyketoses were qualitatively detected. 3-DF was quantitated in the four commercial beer samples at concentrations between 0.4 and 10.1 mg/L.


Assuntos
Cerveja , Saccharomyces cerevisiae , Cerveja/análise , Fermentação , Furaldeído/análogos & derivados , Furaldeído/análise
13.
Phys Chem Chem Phys ; 23(35): 19729-19739, 2021 Sep 15.
Artigo em Inglês | MEDLINE | ID: mdl-34524307

RESUMO

The fundamental understanding of glucose conversion to 5-ethoxymethylfurfural (EMF) and ethyl levulinate (EL) (value-added chemicals from biomass) in ethanol solution catalyzed by a Brønsted acid is limited at present. Consequently, here, the reaction pathways and mechanism of glucose conversion to EMF and EL catalyzed by a Brønsted acid were studied, using an experimental method and quantum chemical calculations at the B3LYP/6-31G(D) and B2PLYPD3/Def2TZVP level under a polarized continuum model (PCM-SMD). By further verification through GC/MS tests, the mechanism and reaction pathways of glucose conversion in ethanol solution catalyzed by a Brønsted acid were revealed, showing that glucose is catalyzed by proton and ethanol, and ethanol plays a bridging role in the process of proton transfer. There are three main reaction pathways: through glucose and ethyl glucoside (G/EG), through fructose, 5-hydroxymethylfurfural (HMF), levulinic acid (LA), and EL (G/F/H/L/EL), and through fructose, HMF, EMF, and EL (G/F/H/E/EL). The G/F/H/E/EL pathway with an energy barrier of 20.8 kcal mol-1 is considered as the thermodynamic and kinetics primary way, in which the reaction rate of this is highly related to the proton transfer in the isomerization of glucose to fructose. The intermediate HMF was formed from O5 via a ring-opening reaction and by the dehydration of fructose, and was further converted to the main product of EMF by etherification or by LA through hydrolysis. EMF and LA are both unstable, and can partially be transformed to EL. This study is beneficial for the insights aiding the understanding of the process and products controlling biomass conversion in ethanol solution.


Assuntos
Etanol/química , Furaldeído/análogos & derivados , Glucose/química , Modelos Moleculares , Ácidos Sulfúricos/química , Biocombustíveis , Catálise , Teoria da Densidade Funcional , Furaldeído/química , Ácidos Levulínicos/química , Termodinâmica
14.
Enzyme Microb Technol ; 150: 109895, 2021 Oct.
Artigo em Inglês | MEDLINE | ID: mdl-34489048

RESUMO

5-Hydroxymethylfurfural oxidase (HMFO) can catalyze both hydroxyl and aldehyde oxidations. It catalyzes 5-hydroxymethylfurfural into 2,5-furandicarboxylic acid. However, the application of HMFO encountered two problems: the expressed HMFO in Escherichia coli. is largely in the form of inclusion bodies, and the by-product of H2O2 has a negative effect on HMFO stability. To solve these problems, recombinant HMFO was generated by fusing the C-terminus to an elastin-like polypeptide (ELP). ELP-HMFO can be expressed with significantly reduced inclusion bodies. ELP-HMFO exhibited improved stability and tolerance toward H2O2. Further recombination is carried out by fusing the N-terminus of HMFO to a glutamic acid-rich leucine zipper motif (ZE). Similarly, recombinant catalase (CAT) is generated by fusing the N-terminus to ELP and fusing the C-terminus to an arginine-rich leucine zipper motif (ZR). ELP-HMFO-ZE can interact specifically with ZR-CAT-ELP, ascribing to the coiled-coil association of ZE and ZR. ELP-HMFO-ZE#ZR-CAT-ELP coordinates the respective catalytic activities of the two enzymes. ELP-HMFO-ZE catalyzes the oxidation of HMF, and the generated hydrogen peroxide is decomposed by ZR-CAT-ELP into H2O and oxygen. During the oxidation of HMF, the cofactor FAD of HMFO is reduced, and molecular oxygen is needed to reoxidize the reduced FAD. The evolved oxygen from the decomposing of H2O2 can just meet the requirement, which can be diffused efficiently from ZR-CAT-ELP to ELP-HMFO-ZE due to the short distance between the two enzymes.


Assuntos
Furaldeído , Peróxido de Hidrogênio , Catalase , Ácidos Dicarboxílicos , Elastina , Furaldeído/análogos & derivados , Furanos
15.
J Agric Food Chem ; 69(32): 9419-9433, 2021 Aug 18.
Artigo em Inglês | MEDLINE | ID: mdl-34374283

RESUMO

Usage of sprouted grains is an increasing trend in thermally processed foods. Sprouting alters the composition of sugars and amino acids, which are Maillard reaction precursors. Free asparagine, total free amino acids, and sugars were monitored during sprouting and yeast and sourdough fermentations. Acrylamide and 5-hydroxymethylfurfural (HMF) were analyzed in heated samples. The asparagine concentration decreased up to 40% after 24-36 h of sprouting, except for buckwheat, and then increased to the initial concentration after 48 h and several folds after 72 h. The increased amount of reducing sugars after sprouting caused higher acrylamide and HMF formation even if the asparagine concentration was lower. Acrylamide and HMF formation decreased after fermentation of sprouted wholemeal because sugars and asparagine were consumed by yeast. A pH drop of 3 units by sourdough fermentation decreased acrylamide formation but increased HMF formation. Results indicated that sprouted cereal products should be produced under controlled conditions to be used in heated foods.


Assuntos
Fagopyrum , Hordeum , Acrilamida , Asparagina , Avena , Fermentação , Furaldeído/análogos & derivados , Calefação , Temperatura Alta , Reação de Maillard , Secale , Açúcares , Triticum
16.
Nat Commun ; 12(1): 4946, 2021 08 16.
Artigo em Inglês | MEDLINE | ID: mdl-34400632

RESUMO

5-Hydroxymethylfurfural (HMF) has emerged as a crucial bio-based chemical building block in the drive towards developing materials from renewable resources, due to its direct preparation from sugars and its readily diversifiable scaffold. A key obstacle in transitioning to bio-based plastic production lies in meeting the necessary industrial production efficiency, particularly in the cost-effective conversion of HMF to valuable intermediates. Toward addressing the challenge of developing scalable technology for oxidizing crude HMF to more valuable chemicals, here we report coordinated reaction and enzyme engineering to provide a galactose oxidase (GOase) variant with remarkably high activity toward HMF, improved O2 binding and excellent productivity (>1,000,000 TTN). The biocatalyst and reaction conditions presented here for GOase catalysed selective oxidation of HMF to 2,5-diformylfuran offers a productive blueprint for further development, giving hope for the creation of a biocatalytic route to scalable production of furan-based chemical building blocks from sustainable feedstocks.


Assuntos
Furaldeído/análogos & derivados , Furaldeído/metabolismo , Galactose Oxidase/genética , Galactose Oxidase/metabolismo , Engenharia de Proteínas , Biocatálise , Catálise , Domínio Catalítico , Furanos , Galactose Oxidase/química , Mutagênese , Oxirredução
17.
Molecules ; 26(16)2021 Aug 05.
Artigo em Inglês | MEDLINE | ID: mdl-34443330

RESUMO

5-Hydroxymethylfurfural (5-HMF) is a harmful substance generated during the processing of black garlic. Our previous research demonstrated that impregnation of black garlic with epigallocatechin gallate (EGCG) could reduce the formation of 5-HMF. However, there is still a lack of relevant research on the mechanism and structural identification of EGCG inhibiting the production of 5-HMF. In this study, an intermediate product of 5-HMF, 3-deoxyglucosone (3-DG), was found to be decreased in black garlic during the aging process, and impregnation with EGCG for 24 h further reduced the formation of 3-DG by approximately 60% in black garlic compared with that in the untreated control. The aging-mimicking reaction system of 3-DG + EGCG was employed to determine whether the reduction of 3-DG was the underlying mechanism of decreased 5-HMF formation in EGCG-treated black garlic. The results showed that EGCG accelerated the decrease of 3-DG and further attenuated 5-HMF formation, which may be caused by an additional reaction with 3-DG, as evidenced by LC-MS/MS analysis. In conclusion, this study provides new insights regarding the role of EGCG in blocking 5-HMF formation.


Assuntos
Catequina/análogos & derivados , Desoxiglucose/análogos & derivados , Furaldeído/análogos & derivados , Alho/efeitos dos fármacos , Alho/metabolismo , Catequina/farmacologia , Desoxiglucose/biossíntese , Desoxiglucose/metabolismo , Relação Dose-Resposta a Droga , Furaldeído/metabolismo
18.
Bioresour Technol ; 340: 125691, 2021 Nov.
Artigo em Inglês | MEDLINE | ID: mdl-34358983

RESUMO

Using acid-treated corn stalk (CS) as biobased carrier, heterogeous SO42-/SnO2-CS catalyst was firstly prepared to catalyze CS into fufural in deep eutectic solvent-water system. The physical properties of SO42-/SnO2-CS were captured by FT-IR, NH3-TPD, XRD, XPS, and BET. SO42-/SnO2-CS (1.2 wt%) could be used to catalyze CS (75.0 g/L) with MgCl2 (15.0 g/L) to produce furfural (102.3 mM) in the yield of 68.2% for 0.5 h at 170 °C in ChCl:EG-water (20:80, v:v). Moreover, enhanced synthesis of furfural was explored based on the structure changes of CS, furfural yields and formation of byproducts. Finally, the potential catalytic mechanism for catalyzing CS into furfural and byproducts was proposed using SO42-/SnO2-CS as catalyst in ChCl:EG-water containing MgCl2. In summary, this established ChCl:EG-water system and optimized catalytic condition facillitated to synthesize furfural from biomass with biobased solid acid catalyst.


Assuntos
Furaldeído , Zea mays , Catálise , Solventes , Espectroscopia de Infravermelho com Transformada de Fourier , Água
19.
Chem Asian J ; 16(20): 3194-3201, 2021 Oct 18.
Artigo em Inglês | MEDLINE | ID: mdl-34402200

RESUMO

The development of efficient, stable, and cost-effective heterogeneous catalysts for catalytic transfer hydrogenation (CTH) of biomass-derived furfural (FAL) is highly desired. Herein, series of N-doped graphitic carbon embedded CoNi bimetallic alloy nanoparticles were fabricated and used for the CTH of FAL to value-added furfuryl alcohol (FOL) with renewable isopropanol as hydrogen donor. Intrinsic catalytic activity examination indicated the catalytic performance of Nix Coy @NGC (x:y=1 : 3, 1 : 1, 3 : 1) nanocatalysts were sensitive to their chemical compositions. The optimal Ni1 Co1 @NGC nanocatalyst with Ni/Co mole ratio of 1 : 1 afforded a largest FOL yield of 89.3% with nearly full conversion of FAL. The synergistic effect enabled by bimetallic alloys and the abundant N-based Lewis base sites and surface Co-N active species were revealed based on systematic structural characterization, responsible for the excellent catalytic efficiency of bimetallic Ni1 Co1 @NGC nanocatalyst for CTH of FAL.


Assuntos
Ligas/química , Cobalto/química , Furaldeído/química , Furanos/síntese química , Grafite/química , Níquel/química , Biomassa , Catálise , Furanos/química , Hidrogenação , Tamanho da Partícula
20.
Angew Chem Int Ed Engl ; 60(42): 22908-22914, 2021 10 11.
Artigo em Inglês | MEDLINE | ID: mdl-34405508

RESUMO

Nickel hydroxide (Ni(OH)2 ) is a promising electrocatalyst for the 5-hydroxymethylfurfural oxidation reaction (HMFOR) and the dehydronated intermediates Ni(OH)O species are proved to be active sites for HMFOR. In this study, Ni(OH)2 is modified by platinum to adjust the electronic structure and the current density of HMFOR improves 8.2 times at the Pt/Ni(OH)2 electrode compared with that on Ni(OH)2 electrode. Operando methods reveal that the introduction of Pt optimized the redox property of Ni(OH)2 and accelerate the formation of Ni(OH)O during the catalytic process. Theoretical studies demonstrate that the enhanced Ni(OH)O formation kinetics originates from the reduced dehydrogenation energy of Ni(OH)2 . The product analysis and transition state simulation prove that the Pt also reduces adsorption energy of HMF with optimized adsorption behavior as Pt can act as the adsorption site of HMF. Overall, this work here provides a strategy to design an efficient and universal nickel-based catalyst for HMF electro-oxidation, which can also be extended to other Ni-based catalysts such as Ni(HCO3 )2 and NiO.


Assuntos
Furaldeído/análogos & derivados , Hidróxidos/química , Níquel/química , Platina/química , Adsorção , Biomassa , Catálise , Furaldeído/química , Cinética , Nanopartículas Metálicas/química , Oxirredução , Análise Espectral Raman
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