RESUMEN
This research evaluated the occurrence and bioaccessibility of acrylamide and HMF in commercial instant coffees (IC) and coffee substitutes (CS), considering both isolated consumption and combination with milk. There were no significant differences in acrylamide content between IC and CS samples (median: 589 vs. 671 µg/kg), but higher variability was reported for CS, probably due to their varied composition (roasted cereals, nuts, honey, dehydrated fruits, and/or chicory). Acrylamide level were always below the EU benchmark for each category. HMF contents were similar between both groups (1354-5127 mg/kg for IC and 735-7134 mg/kg for CS; median: 2890 vs. 2960 mg/kg), with no clear ingredient relationship. Since IC consumption by the Spanish population is ten times higher than that of CS, exposure to acrylamide and HMF was higher from IC (6.8 vs. 1.07 ng/kg body weight/day for acrylamide; 39.1 vs. 4.2 µg/kg body weight/day for HMF). The standardized in vitro gastrointestinal digestion protocol (INFOGEST) was used. The gastrointestinal process reduced the bioaccessibility of acrylamide up to 27.2 % in IC and to 22.4 % in CS, regardless of the presence of milk. HMF bioaccessibility from IC significantly dropped after the gastrointestinal digestion, whereas it greatly increased for CS. The presence of milk did not affect HMF bioaccessibility. These results highlight the importance of assessing food bioaccessibility in typical consumption scenarios, providing a holistic view and a realistic evaluation of the potential risks associated with acrylamide and HMF exposure in the diet.
Asunto(s)
Acrilamida , Café , Digestión , Furaldehído , Leche , Acrilamida/análisis , Acrilamida/farmacocinética , Café/química , Leche/química , Animales , Furaldehído/análogos & derivados , Furaldehído/análisis , Disponibilidad Biológica , Contaminación de Alimentos/análisis , Humanos , España , Nueces/química , Bebidas/análisisRESUMEN
Using halloysite clay and vitamin B1 hydrochloride, a novel acidic halloysite-dendrimer catalytic composite has been developed for conversion of fructose to 5-hydroxymthylfurfural. To grow the dendritic moiety on halloysite, it was first functionalized and then reacted with melamine, epichlorohydrin and vitamin B1 hydrochloride respectively. Then, the resulting composite was treated with ZnCl2 to furnish Lewis acid sites. Use of vitamin B1 as the cationic moiety of ionic liquid obviated use of toxic chemicals and resulted in more environmentally friendly composite. Similarly, dendritic moiety of generation 2 was also grafted on halloysite and the activity of both catalysts for conversion of fructose to 5-hydroxymthylfurfural was investigated to disclose the role of dendrimer generation. For the best catalytic composite, the reaction variables were optimized via RSM and it was revealed that use of 0.035 g catalyst per 0.1 g fructose at 95 °C furnished HMF in 96% yield in 105 min. Turnover numbers (TONs) and frequencies (TOFs) were estimated to be 10,130 and 5788 h-1, respectively. Kinetic studies also underlined that Ea was 22.85 kJ/mol. The thermodynamic parameters of Δ H ≠ , Δ S ≠ and Δ G ≠ , were calculated to be 23 kJ/mol, - 129.2 J/mol and 72.14 kJ/mol, respectively. Notably, the catalyst exhibited good recyclability and hot filtration approved heterogeneous nature of catalysis.
Asunto(s)
Arcilla , Dendrímeros , Furaldehído , Tiamina , Catálisis , Arcilla/química , Furaldehído/análogos & derivados , Furaldehído/química , Dendrímeros/química , Dendrímeros/síntesis química , Tiamina/química , Tiamina/análogos & derivados , Fructosa/química , Cinética , Silicatos de Aluminio/química , Triazinas/química , Cloruros/química , Compuestos de Zinc/químicaRESUMEN
This study investigated the impact of processing temperatures (190 °C, 210 °C, and 230 °C) and durations (7 min, 10 min, and 14 min) on the formation of Maillard reaction products (MRPs) and antioxidant activities in pan baked buns. Key Maillard reaction indicators, including glyoxal (GO), methylglyoxal (MGO), 5-hydroxymethylfurfural (5-HMF), melanoidins, and fluorescent advanced glycation end products (AGEs) were quantified. The results demonstrated significant increases in GO, MGO, 5-HMF contents (p < 0.05), and antioxidant activities (p < 0.05) when the buns were baked at 210 °C for 14 min, 230 °C for 10 min and 14 min. However, the interior MRPs of baked buns were minimally affected by the baking temperature and duration. Prolonged heating temperatures and durations exacerbated MRPs production (43.8 %-1038 %) in the bottom crust. Nonetheless, this process promoted the release of bound phenolic compounds and enhanced the antioxidant activity. Heating induces the thermal degradation of macromolecules in food, such as proteins and polysaccharides, which releases bound phenolic compounds by disrupting their chemical bonds within the food matrix. Appropriate selections of baking parameters can effectively reduce the formation of MRPs while simultaneously improve sensory quality and health benefit of the pan baked buns. Considering the balance between higher antioxidant properties and lower MRPs, the optimal thermal parameters for pan baked buns were 210 °C for 10 min. Furthermore, a normalized analysis revealed a consistent trend for GO, MGO, 5-HMF, fluorescent AGEs, and melanoidins. Moreover, MRPs were positively correlated with total contents of phenolic compounds, ferric-reducing antioxidant power (FRAP), and color, but negatively correlated with moisture contents and reducing sugars. Additionally, the interaction between baking conditions and Maillard reactions probably contributed to enhanced primary flavors in the final product. This study highlights the importance of optimizing baking parameters to achieve desirable MRPs levels, higher antioxidant activity, and optimal sensory attributes in baked buns.
Asunto(s)
Antioxidantes , Culinaria , Furaldehído , Productos Finales de Glicación Avanzada , Calor , Reacción de Maillard , Piruvaldehído , Antioxidantes/análisis , Antioxidantes/química , Furaldehído/análogos & derivados , Furaldehído/análisis , Furaldehído/química , Piruvaldehído/química , Culinaria/métodos , Humanos , Glioxal/química , Gusto , Polímeros/química , Pan/análisisRESUMEN
Economically feasible ethanol production requires efficient hydrolysis of lignocellulosic biomass and high-temperature processing to enable simultaneous saccharification and fermentation. During the lignocellulolysic hydrolysate, the yeast must encounter with a multiple of inhibitors such as heat and furfural. To solve this problem, a potential fermentative yeast strain that tolerated simultaneous multistress and enhance ethanol concentration was investigated. Twenty yeast isolates were classified into two major yeast species, namely Pichia kudriavzevii (twelve isolates) and Candida tropicalis (eight isolates). All P. kudriavzevii isolates were able to grow at high temperature (45 °C) and exhibited stress tolerance toward furfural. Among P. kudriavzevii isolates, NUCG-S3 presented the highest specific growth rate under each stress condition of heat and furfural, and multistress. Morphological changes in P. kudriavzevii isolates (NUCG-S2, NUCG-S3, NUKL-P1, NUKL-P3, and NUOR-J1) showed alteration in mean cell length and width compared to the non-stress condition. Ethanol production by glucose was also determined. The yeast strain, NUCG-S3, gave the highest ethanol concentrations at 99.46 ± 0.82, 62.23 ± 0.96, and 65.80 ± 0.62 g/l (P < 0.05) under temperature of 30 °C, 40 °C, and 42 °C, respectively. The tolerant isolated yeast NUCG-S3 achieved ethanol production of 53.58 ± 3.36 and 48.06 ± 3.31 g/l (P < 0.05) in the presence of 15 mM furfural and multistress (42 °C with 15 mM furfural), respectively. Based on the results of the present study, the novel thermos and furfural-tolerant yeast strain P. kudriavzevii NUCG-S3 showed promise as a highly proficient yeast for high-temperature ethanol fermentation.
Asunto(s)
Etanol , Fermentación , Furaldehído , Pichia , Pichia/metabolismo , Pichia/crecimiento & desarrollo , Pichia/fisiología , Etanol/metabolismo , Furaldehído/metabolismo , Furaldehído/análogos & derivados , Estrés Fisiológico , Candida tropicalis/metabolismo , Candida tropicalis/crecimiento & desarrollo , Calor , Glucosa/metabolismo , Hidrólisis , Biomasa , Lignina/metabolismoRESUMEN
The process of preprocessing techniques such as acid and alkali pretreatment in lignocellulosic industry generates substantial solid residues and lignocellulosic pretreatment wastewater (LPW) containing glucose, xylose and toxic byproducts. In this study, furfural and vanillin were selected as model toxic byproducts. Kurthia huakuii as potential strain could tolerate to high concentrations of inhibitors. The results indicated that vanillin exhibited a higher inhibitory effect on K. huakuii (3.95 % inhibition rate at 1 g/L than furfural (0.45 %). However, 0.5 g/L vanillin promoted the bacterial growth (-2.35 % inhibition rate). Interestingly, the combination of furfural and vanillin exhibited antagonistic effects on bacterial growth (Q<0.85). Furfural and vanillin could be bio-transformed into less toxic molecules (furfuryl alcohol, furoic acid, vanillyl alcohol, and vanillic acid) by K. huakuii, and inhibitor degradation rate could be promoted by expression of antioxidant enzymes. This study provides important insights into how bacteria detoxify inhibitors in LPW, potentially enhancing resource utilization.
Asunto(s)
Benzaldehídos , Biomasa , Lignina , Aguas Residuales , Lignina/metabolismo , Aguas Residuales/química , Benzaldehídos/farmacología , Furaldehído/farmacología , Furaldehído/metabolismo , Furaldehído/análogos & derivados , Biodegradación Ambiental , Ácido Vanílico/farmacología , Ácido Vanílico/metabolismo , Bacterias/metabolismo , Bacterias/efectos de los fármacosRESUMEN
Foods contaminants pose a challenge for food producers and consumers. Due to its spontaneous formation during heating and storage, hydroxymethylfurfural (HMF) is a prevalent contaminant in foods rich in carbohydrates and proteins. Colorimetric assays, such as the Seliwanoff test, offer a rapid and cost-effective method for HMF quantification but require careful optimization to ensure accuracy. We addressed potential interference in the Seliwanoff assay by systematically evaluating parameters like incubation time, temperature, and resorcinol or hydrochloric acid concentration, as well as the presence of interfering carbohydrates. Samples were analyzed using a UV-Vis spectrophotometer in scan mode, and data obtained were validated using HPLC, which also enabled quantification of unreacted HMF for assessing the protocol's accuracy. Incubation time and hydrochloric acid percentage positively influenced the colorimetric assay, while the opposite effect was observed with the increase in resorcinol concentration. Interference from carbohydrates was eliminated by reducing the acid content in the working reagent. HPLC analyses corroborated the spectrophotometer data and confirmed the efficacy of the proposed method. The average HMF content in balsamic vinegar samples was 1.97 ± 0.94 mg/mL. Spectrophotometric approaches demonstrated to efficiently determine HMF in complex food matrices. The HMF levels detected in balsamic vinegars significantly exceeded the maximum limits established for honey. This finding underscores the urgent need for regulations that restrict contaminant levels in various food products.
Asunto(s)
Furaldehído , Espectrofotometría , Furaldehído/análogos & derivados , Furaldehído/análisis , Espectrofotometría/métodos , Cromatografía Líquida de Alta Presión/métodos , Resorcinoles/análisis , Resorcinoles/química , Contaminación de Alimentos/análisis , Análisis de los Alimentos/métodos , Ácido Acético/análisis , Ácido Acético/químicaRESUMEN
This study used a green validated method to evaluate the risk of exposure of individuals of different ages to acrylamide (AA) and 5-hydroxymethylfurfural (5-HMF) by consuming white and wholewheat bread. Recoveries of AA and 5-HMF were 100.7% and 100.1%, respectively, while uncertainty was 2.3% and 6.2%. Levels of AA ranged from 617.22 to 3151.8 µg/kg while levels of 5-HMF ranged from 180.5 to 648.2 µg/kg. Female adolescents were almost 2-fold exposed to AA when they consumed 100% wholewheat bread (2.93 µg/kg bw/day) by comparison with white bread (1.72 µg/kg bw/day). Estimated daily exposure to AA was 1.5-fold higher than international recommendations. These findings raise concern for health risks associated with exposure to processing contaminant as the result of bread consumption, especially made from whole grains. Since development of those compounds is inevitable during breadmaking, it is crucial to standardize processing conditions and recipes to mitigate it.
Asunto(s)
Acrilamida , Pan , Contaminación de Alimentos , Furaldehído , Acrilamida/análisis , Acrilamida/química , Furaldehído/análogos & derivados , Furaldehído/análisis , Pan/análisis , Femenino , Humanos , Contaminación de Alimentos/análisis , Adolescente , Niño , Adulto , Masculino , Adulto Joven , Preescolar , Granos Enteros/química , Persona de Mediana Edad , Triticum/químicaRESUMEN
High inhibitor concentrations in lignocellulose feedstock negatively affect the degradation rate of biodetoxification strains. This study designed two adaptive laboratory evolutions in solid substrate and liquid medium to boost the biodetoxification capacity of P. variotii to high titers of lignocellulose-derived inhibitors, resulting in two evolved strains AC70 and ZW70. The results showed that the evolutionary adaptation in liquid medium could better boost the acetic acid assimilation compared to that on solid substrate. Transcriptional analysis revealed that the evolved strains exhibited a significant upregulation of adh, acs, ach1, and ackA directly related to the initial steps of acetate and furan aldehydes metabolisms. ZW70 strain can effectively remove the high concentration inhibitors cocktail from the hydrolysates derived from pretreated wheat straw and furfural residues. The biodetoxified hydrolysates by ZW70 were successfully used for cellulose chiral L-lactic acid production with the titers of â¼110 g/L, which were over 20 % higher than that detoxified by parental strain.
Asunto(s)
Lignina , Lignina/metabolismo , Hidrólisis , Triticum , Celulosa/metabolismo , Furaldehído/análogos & derivados , Furaldehído/farmacología , Furaldehído/metabolismo , Adaptación Fisiológica/efectos de los fármacos , Ácido Láctico/metabolismoRESUMEN
Advanced glycation end products (AGEs), heterocyclic aromatic amines (HAAs), acrylamide (AA), 5-hydroxymethylfurfural (5-HMF), and polycyclic aromatic hydrocarbons (PAHs) are toxic substances that are produced in certain foods during thermal processing by using common high-temperature unit operations such as frying, baking, roasting, grill cooking, extrusion, among others. Understanding the formation pathways of these potential risk factors, which can cause cancer or contribute to the development of many chronic diseases in humans, is crucial for reducing their occurrence in thermally processed foods. During thermal processing, food rich in carbohydrates, proteins, and lipids undergoes a crucial Maillard reaction, leading to the production of highly active carbonyl compounds. These compounds then react with other substances to form harmful substances, which ultimately affect negatively the health of the human body. Although these toxic compounds differ in various forms of formation, they all partake in the common Maillard pathway. This review primarily summarizes the occurrence, formation pathways, and reduction measures of common toxic compounds during the thermal processing of food, based on independent studies for each specific contaminant in its corresponding food matrix. Finally, it provides several approaches for the simultaneous reduction of multiple toxic compounds.
Asunto(s)
Acrilamida , Contaminación de Alimentos , Manipulación de Alimentos , Productos Finales de Glicación Avanzada , Calor , Reacción de Maillard , Humanos , Contaminación de Alimentos/análisis , Furaldehído/análogos & derivados , Hidrocarburos Policíclicos Aromáticos , CulinariaRESUMEN
Roasting is necessary for bringing out the aroma and flavor of coffee beans, making coffee one of the most consumed beverages. However, this process also generates a series of toxic compounds, including acrylamide and furanic compounds (5-hydroxymethylfurfural, furan, 2-methylfuran, 3-methylfuran, 2,3-dimethylfuran, and 2,5-dimethylfuran). Furthermore, not much is known about the formation of these compounds in emerging coffee formulations containing alcohol and sugars. Therefore, this study investigated the effect of roasting time and degree on levels of acrylamide and furanic compounds in arabica coffee using fast and slow roasting methods. The fast and slow roasting methods took 5.62 min and 9.65 min, respectively, and reached a maximum of 210 °C to achieve a light roast. For the very dark roast, the coffee beans were roasted for 10.5 min and the maximum temperature reached 245 °C. Our findings showed that the levels of acrylamide (375 ± 2.52 µg kg-1) and 5-HMF (194 ± 11.7 mg kg-1) in the slow-roasted coffee were 35.0 % and 17.4 % lower than in fast-roasted coffee. Furthermore, light roast coffee had significantly lower concentrations of acrylamide and 5-HMF than very dark roast, with values of 93.7 ± 7.51 µg kg-1 and 21.3 ± 10.3 mg kg-1, respectively. However, the levels of furan and alkylfurans increased with increasing roasting time and degree. In this study, we also examined the concentrations of these pollutants in new coffee formulations consisting of alcohol-, sugar-, and honey-infused coffee beans. Formulations with honey and sugar resulted in higher concentrations of 5-HMF, but no clear trend was observed for acrylamide. On the other hand, formulations with honey had higher concentrations of furan and alkylfurans. These results indicate that optimizing roasting time and temperature might not achieve the simultaneous reduction of all the pollutants. Additionally, sugar- and honey-infused coffee beans are bound to have higher furanic compounds, posing a higher health risk.
Asunto(s)
Acrilamida , Café , Furaldehído , Furanos , Calor , Acrilamida/análisis , Furanos/análisis , Café/química , Furaldehído/análisis , Furaldehído/análogos & derivados , Culinaria/métodos , Coffea/química , Semillas/química , Manipulación de Alimentos/métodos , Factores de Tiempo , Aditivos Alimentarios/análisisRESUMEN
Southern Chile native potatoes are an interesting raw material to produce novel snacks like colored potato chips. These novel products should be comprehensively evaluated for the presence of undesirable compounds such as acrylamide, 5-hydroxymethylfurfural and furan, the main neoformed contaminants in starchy rich fried foods. This study evaluated the neoformed contaminant levels and oil content on chips made from eleven Chilean potato accessions and compared them with commercial samples. The neoformed contaminant contents were related to Maillard reaction precursor levels (reducing sugars and asparagine) and secondary metabolites (phenolic compounds and carotenoids). Neoformed contaminants correlated well among them and were weakly correlated with reducing sugars and asparagine. Acrylamide level in native potato chips ranged from 738.2 to 1998.6 µg kg-1 while from 592.6 to 2390.5 µg kg-1 in commercial samples. Thus, there is need to implement neoformed contaminant mitigation strategies at different steps of the production chain of colored potato chips.
Asunto(s)
Acrilamida , Culinaria , Contaminación de Alimentos , Reacción de Maillard , Solanum tuberosum , Solanum tuberosum/química , Solanum tuberosum/metabolismo , Contaminación de Alimentos/análisis , Acrilamida/análisis , Acrilamida/metabolismo , Chile , Calor , Metabolismo Secundario , Fenoles/metabolismo , Fenoles/análisis , Fenoles/química , Tubérculos de la Planta/química , Tubérculos de la Planta/metabolismo , Carotenoides/análisis , Carotenoides/metabolismo , Carotenoides/química , Furaldehído/análogos & derivadosRESUMEN
Furfurals, including 2-furaldehyde, 5-methylfurfural and 5-hydroxymethylfurfural, widely exist in carbohydrate-rich daily foods, and may have toxic effects on humans. Here, a new headspace extraction-paper spray mass spectrometry (HSPS-MS/MS) method was established for furfural detection, in which the extraction and derivatization of volatiles with pre-loaded derivatization agent on paper tips is combined with paper spray mass spectrometry for detection. By this simple and cheap approach, interference of non-volatile matrix compounds is prevented, and the derivatization agent improves electrospray-type ionization efficiency, thus increasing selectivity and sensitivity. The approach was optimized, by investigating positioning during extraction, extraction duration, derivatization agent, addition of internal standard for quantification and finally validated. For this, the developed method was benchmarked against HPLC-UV and could obtain detections limits of 0.32-0.40 µg mL-1 for 2-furaldehyde, 5-methylfurfural and 5-hydroxymethylfurfural in olive oil. Moreover, fast screening of free furfurals in soy sauce, coffees and teas was demonstrated with the HSPS-MS/MS method.
Asunto(s)
Furaldehído , Espectrometría de Masas en Tándem , Furaldehído/análogos & derivados , Furaldehído/análisis , Furaldehído/aislamiento & purificación , Espectrometría de Masas en Tándem/métodos , Papel , Aceite de Oliva/química , Contaminación de Alimentos/análisisRESUMEN
This work outlines the first microwave (MW)-assisted protocol for the production of biofuel precursor furfural (FF) from the raw agricultural waste almond hull (AH), olive stone (OS), and the winemaking-derived grape stalk (GS), grape marc (GM) and exhausted grape marc (EGM) through a one-pot synthesis process. To enhance the overall yield, a catalytic process was firstly developed from xylose, major constituent of hemicellulose present in lignocellulosic biomass. This method afforded FF with 100 % selectivity, yielding over 85 % in isolated product when using H2SO4, as opposed to a 37 % yield with AlCl3·6H2O, at 150 °C in only 10 min. For both catalysts, the developed methodology was further validated, proving adaptable and efficient in producing the targeted FF from the aforementioned lignocellulosic raw materials. More specifically, the employment of AlCl3·6H2O resulted in the highest selectivity (up to 89 % from GM) and FF yield (42 % and 39 % molar from OS and AH, respectively), maintaining notable selectivity for the latter (61 and 48 % from AH and OS). At this regard, and considering the environmental factor of sustainability, it is important to point out the role of AlCl3·6H2O in contrast to H2SO4, thus mitigating detrimental substances. This study provides an important management of agricultural waste through sustainable practises for the development of potential bio-based chemicals, aligning with Green Chemistry and process intensification principles.
Asunto(s)
Furaldehído , Microondas , Prunus dulcis , Vino , Furaldehído/análogos & derivados , Vino/análisis , Prunus dulcis/química , Biocombustibles/análisis , Vitis , Lignina/química , Aceites de Plantas/química , Catálisis , Cloruro de Aluminio , Olea/químicaRESUMEN
Coffee, a globally consumed beverage, has raised concerns in Islamic jurisprudence due to the possible presence of alcohol compounds. This research aims to utilise the sensitivity and reliability of 1H NMR spectroscopy in the quantification of alcohol compounds such as ethanol, furfuryl alcohol, and 5-(hydroxymethyl) furfural (HMF) in commercial instant coffee. Analysis of seven products was performed using advanced 1H Nuclear Magnetic Resonance (NMR) spectroscopy together with Statistical Total Correlation Spectroscopy (STOCSY) and Resolution-Enhanced (RED)-STORM. The analysis of the 100 mg sample revealed the absence of ethanol. The amount of furfuryl alcohol and HMF in the selected commercial instant coffee samples was 0.817 µg and 0.0553 µg, respectively. This study demonstrates the utility of 1H NMR spectroscopy in accurate quantification of trace components for various applications.
Asunto(s)
Café , Café/química , Espectroscopía de Resonancia Magnética/métodos , Islamismo , Furanos/análisis , Etanol/análisis , Furaldehído/análisis , Furaldehído/análogos & derivados , Alcoholes/análisisRESUMEN
Rapid, efficient, versatile, easy-to-use, and non-expensive analytical approaches are globally demanded for food analysis. Many ambient ionization approaches based on electrospray ionization (ESI) have been developed recently for the rapid molecular characterization of food products. However, those approaches mainly suffer from insufficient signal duration for comprehensive chemical characterization by tandem MS analysis. Here, a commercially available disposable gel loading tip is used as a low-cost emitter for the direct ionization of untreated food samples. The most important advantages of our approach include high stability, and durability of the signal (> 10 min), low cost (ca. 0.1 USD per run), low sample and solvent consumption, prevention of tip clogging and discharge, operational simplicity, and potential for automation. Quantitative analysis of sulfapyridine, HMF (hydroxymethylfurfural), and chloramphenicol in real sample shows the limit-of-detection 0.1 µg mL-1, 0.005 µg mL-1, 0.01 µg mL-1; the linearity range 0.1-5 µg mL-1, 0.005-0.25 µg mL-1, 0.01-1 µg mL-1; and the linear fits R2 ≥ 0.980, 0.991, 0.986. Moreover, we show that tip-ESI can also afford sequential molecular ionization of untreated viscous samples, which is difficult to achieve by conventional ESI. We conclude that tip-ESI-MS is a versatile analytical approach for the rapid chemical analysis of untreated food samples.
Asunto(s)
Análisis de los Alimentos , Límite de Detección , Espectrometría de Masa por Ionización de Electrospray , Espectrometría de Masa por Ionización de Electrospray/métodos , Análisis de los Alimentos/métodos , Geles/química , Cloranfenicol/análisis , Contaminación de Alimentos/análisis , Furaldehído/análisis , Furaldehído/análogos & derivadosRESUMEN
Biobased furans have emerged as chemical building blocks for the development of materials because of their diverse scaffolds and as they can be directly prepared from sugars. However, selective, efficient, and cost-effective scalable conversion of biobased furans remains elusive. Here, we report a robust transaminase (TA) from Shimia marina (SMTA) that enables the scalable amination of biobased furanaldehydes with high activity and broad substrate specificity. Crystallographic and mutagenesis analyses provide mechanistic insights and a structural basis for understanding SMTA, which enables a higher substrate conversion. The enzymatic cascade process established in this study allows one-pot synthesis of 2,5-bis(aminomethyl)furan (BAMF) and 5-(aminomethyl)furan-2-carboxylic acid from 5-hydroxymethylfurfural. The biosynthesis of various furfurylamines, including a one-pot cascade reaction for BAMF generation using whole cells, demonstrates their practical application in the pharmaceutical and polymer industries.
Asunto(s)
Biocatálisis , Furanos , Transaminasas , Furanos/química , Furanos/metabolismo , Transaminasas/metabolismo , Transaminasas/genética , Transaminasas/química , Especificidad por Sustrato , Furaldehído/análogos & derivados , Furaldehído/metabolismo , Furaldehído/química , Aminación , Aminas/química , Aminas/metabolismo , Cristalografía por Rayos XRESUMEN
The thermal treatment carried out in the processing of apple products is very likely to induce Maillard reaction to produce furfurals, which have raised toxicological concerns. This study aimed to elucidate the formation of furfural compounds in apple products treated with pasteurization and high pressure processing (HPP). The method for simultaneous determination of five furfural compounds including 5-hydroxymethyl-2-furfural (5-HMF), furfural (F), 4-hydroxy-2,5-dimethyl-3(2H)-furanone (HDMF), 2-acetylfuran (FMC), and 5-Methyl-2-furfural (MF) using high performance liquid chromatography equipped with diode array detector (HPLC-DAD) was successfully developed and validated. All five furfurals exhibited an increasing trend after the pasteurization treatment of apple clear juice, cloudy juice, and puree. 5-HMF, F, FMC, and MF were increased significantly during the precooking of apple puree. Whereas there was no significant change in the furfurals formation after apple products treated with high pressure processing (HPP) with 300 MPa and 15 min. Based on the variation of the fructose, glucose and sucrose detected in apple products after thermal treatment, it revealed that the saccharides and thermal treatment have great effect on the furfural compounds formation. The commercial fruit juice samples with different treatments and fruit puree samples treated with pasteurization were also analyzed. Five furfurals were detected more frequently in the fruit juice samples treated with pasteurization or ultra-high temperature instantaneous sterilization (UHT) than those treated with HPP. 5-HMF and FMC were detected in all fruit puree samples treated with pasteurization, followed by F, MF, and HDMF with the detection rate of 79.31 %, 72.41 %, and 51.72 %. The results could provide a reference for risk assessment of furfural compounds and dietary guidance of fruit products for human, especially for infants and young children. Moreover, moderate HPP treatment with 300 MPa and 15 min would be a worthwhile alternative processing technology in the fruit juice and puree production to reduce the formation of furfural compounds.
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Manipulación de Alimentos , Jugos de Frutas y Vegetales , Furaldehído , Malus , Pasteurización , Presión , Malus/química , Furaldehído/análisis , Furaldehído/análogos & derivados , Cromatografía Líquida de Alta Presión , Jugos de Frutas y Vegetales/análisis , Manipulación de Alimentos/métodos , Reacción de Maillard , Frutas/química , Furanos/análisisRESUMEN
Fabrication of sustainable bio-based malleable thermosets (BMTs) with excellent mechanical properties and reprocessing ability for applications in electronic devices has attracted more and more attention but remains significant challenges. Herein, the BMTs with excellent mechanical robustness and reprocessing ability were fabricated via integrating with radical polymerization and Schiff-base chemistry, and employed as the flexible substrate to prepare the capacitive sensor. To prepare the BMTs, an elastic bio-copolymer derived from plant oil and 5-hydroxymethylfurfural was first synthesized, and then used to fabricate the dynamic crosslinked BMTs through Schiff-base chemistry with the amino-modified cellulose and polyether amine. The synergistic effect of rigid cellulose backbone and the construction of dynamic covalent crosslinking network not only achieved high tensile strength (8.61 MPa) and toughness (3.77 MJ/m3) but also endowed the BMTs with excellent reprocessing ability with high mechanical toughness recovery efficiency of 104.8 %. More importantly, the BMTs were used as substrates to fabricate the capacitive sensor through the CO2-laser irradiation technique. The resultant capacitive sensor displayed excellent and sensitive humidity sensing performance, which allowed it to be successfully applied in human health monitoring. This work paved a promising way for the preparation of mechanical robustness malleable bio-thermosets for electronic devices.
Asunto(s)
Celulosa , Furaldehído , Aceites de Plantas , Celulosa/química , Furaldehído/química , Furaldehído/análogos & derivados , Aceites de Plantas/química , Capacidad Eléctrica , Temperatura , Resistencia a la Tracción , HumanosRESUMEN
A facile biphasic system composed of choline chloride (ChCl)-based deep eutectic solvent (DES) and methyl isobutyl ketone (MIBK) was developed to realize the furfural production, lignin separation and preparation of fermentable glucose from Eucalyptus in one-pot. Results showed that the ChCl/1,2-propanediol/MIBK system owned the best property to convert hemicelluloses into furfural. Under the optimal conditions (MRChCl:1,2-propanediol = 1:2, raw materials:DES:MIBK ratio = 1:4:8 g/g/mL, 0.075 mol/L AlCl3·6H2O, 140 °C, and 90 min), the furfural yield and glucose yield reached 65.0 and 92.2 %, respectively. Meanwhile, the lignin with low molecular weight (1250-1930 g/mol), low polydispersity (DM = 1.25-1.53) and high purity (only 0.08-2.59 % carbohydrate content) was regenerated from the biphasic system. With the increase of pretreatment temperature, the ß-O-4, ß-ß and ß-5 linkages in the regenerated lignin were gradually broken, and the content of phenolic hydroxyl groups increased, but the content of aliphatic hydroxyl groups decreased. This research provides a new strategy for the comprehensive utilization of lignocellulose in biorefinery process.
Asunto(s)
Celulosa , Eucalyptus , Furaldehído , Lignina , Eucalyptus/química , Eucalyptus/metabolismo , Lignina/química , Furaldehído/química , Furaldehído/análogos & derivados , Furaldehído/metabolismo , Celulosa/química , Metil n-Butil Cetona/química , Metil n-Butil Cetona/metabolismo , Colina/química , Propilenglicol/química , Glucosa/metabolismo , Glucosa/química , Fermentación , Solventes/químicaRESUMEN
The baking process has the potential to generate health-risk compounds, including products from lipid oxidation and Maillard reaction. Pre- and post-digestion levels of hydroxymethylfurfural (HMF), malondialdehyde (MDA), glyoxal (GO), and methylglyoxal (MGO) were studied in cakes formulated with hazelnut and sunflower oil, along with their oleogels as margarine substitutes. The concentration of HMF in oil and oleogel-formulated cakes increased after digestion compared to cakes formulated with margarine. The MDA values were between 82 and 120 µg/100 g in oil and oleogel formulated cakes before digestion and a decrease was observed after digestion. The substitution of margarine with oil and oleogels resulted in the production of high amounts of GO and MGO in cakes. However, the highest bioaccessibility as 318.2% was found in cakes formulated by margarine for GO. Oleogels may not pose a potential health benefit compared to margarines due to the formation of HMF, MDA, GO, and MGO.