Glyoxal

乙二醛
  • 文章类型: Journal Article
    控制美拉德反应可能会影响2-乙酰基-1-吡咯啉的生成,大米中的关键香气化合物。在这项研究中,全面研究了葡萄糖/脯氨酸模型系统中2-乙酰基-1-吡咯啉的积累动力学,并添加了额外的甲基乙二醛或乙二醛以提高大米蒸煮过程中2-乙酰基-1-吡咯啉的浓度。利用多响应动力学模型推导动力学参数,乙二醛的形成,作为反应中间体,对2-乙酰基-1-吡咯啉的总生成速率进行速率测定。此外,虽然2-乙酰基-1-吡咯啉的产生更容易发生在较低的活化能,在120°C和140°C下,2-乙酰基-1-吡咯啉的消耗速率高得多,导致在100°C的较低温度下最大的2-乙酰基-1-吡咯啉积累。此外,在米饭中加入0.05μmol/kg的甲基乙二醛可显着提高2-乙酰基-1-吡咯啉的生成。这项工作表明,可以通过在热加工之前稍微积累中间体来开发具有卓越风味品质的大米产品。
    Controlling the Maillard reaction may affect the generation of 2-acetyl-1-pyrroline, the key aroma compound in rice. In this study, the kinetics of 2-acetyl-1-pyrroline accumulation in the glucose/proline model system was comprehensively investigated and extra methylglyoxal or glyoxal was added to enhance 2-acetyl-1-pyrroline concentrations during rice cooking. Using the multi-response kinetic modeling to derive kinetic parameters, the formation of glyoxal, as the reactive intermediate, was rate-determining for the overall generation rate of 2-acetyl-1-pyrroline. Besides, although 2-acetyl-1-pyrroline generation was easier to occur with lower activation energy, much higher depletion rates of 2-acetyl-1-pyrrroline at 120 °C and 140 °C led to maximal 2-acetyl-1-pyrroline accumulation at the lower temperature of 100 °C. Furthermore, the inclusion of 0.05 μmol/kg additional methylglyoxal in cooked rice significantly enhanced 2-acetyl-1-pyrroline generation. The work suggested that the development of rice products with superior flavor quality may be achieved by the slight accumulation of intermediates prior to thermal processing.
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  • 文章类型: Journal Article
    系统性红斑狼疮(SLE)是一种慢性,自身免疫性疾病,通常以严重的病程和不清楚的病因为特征。蛋白质糖基化反应,也被称为糖化,可能与SLE的病因有关。晚期糖基化终产物(AGEs)表现出细胞毒性,影响细胞信号,削弱细胞外蛋白质的功能,并可能充当新表位。葡萄糖酮(GS),乙二醛(GO),和甲基乙二醛(MGO)是参与糖氧化的α-二羰基化合物(α-DC)的实例。该研究旨在评估这三种化合物在SLE患者血清中的浓度,并将结果与健康个体进行比较。
    31名患有SLE的妇女和26名健康个体被纳入研究。采用荧光检测的高效液相色谱法评估血清样品中α-DC的浓度。结果与疾病持续时间等参数之间的相关性,年龄,肾小球滤过率(GFR),系统性红斑狼疮疾病活动指数2000(SLEDAI-2K),和肌酐进行分析。
    SLE患者表现出较低浓度的葡萄糖酮,乙二醛,和甲基乙二醛比对照组。相关性分析显示被检查组之间存在差异。
    在患有SLE的女性中,α-DCs代谢过程发生了改变。SLE患者的特征在于低血清水平的α-DC。我们假设,在氧化条件下,蛋白酶体降解受阻或α-DC的快速消耗可能会导致观察到的这些化合物的低浓度。
    UNASSIGNED: Systemic lupus erythematosus (SLE) is a chronic, autoimmune disease, often characterised by severe course and unclear etiopathogenesis. The reaction of protein glycoxidation, also known as glycation, may be linked to etiopathogenesis of SLE. Advanced glycation end-products (AGEs) exhibit cytotoxic properties, affect cellular signalling, impair functions of extracellular proteins, and may act as neoepitopes. Glucosone (GS), glyoxal (GO), and methylglyoxal (MGO) are examples of α-dicarbonyl compounds (α-DCs) partaking in glycoxidation. The study aimed to evaluate concentrations of these three compounds in blood serum of SLE patients, and to compare the results with healthy individuals.
    UNASSIGNED: 31 women suffering from SLE and 26 healthy individuals were included in the study. High-performance liquid chromatography with fluorescence detection was applied to evaluate concentrations of α-DCs in their serum samples. Correlations between the results and parameters such as disease duration time, age, glomerular filtration rate (GFR), Systemic Lupus Erythematosus Disease Activity Index 2000 (SLEDAI-2K), and creatinine were analysed.
    UNASSIGNED: The SLE patients exhibited lower concentrations of glucosone, glyoxal, and methylglyoxal than the control group. Analysis of correlations showed a difference between the examined groups.
    UNASSIGNED: In women suffering from SLE the course of α-DCs metabolism is altered. SLE patients are characterised by low serum levels of α-DCs. We hypothesise that either hindered proteasomal degradation or fast consumption of α-DCs in oxidative conditions may cause the observed low concentration of these compounds.
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  • 文章类型: Journal Article
    背景:羰基化合物,尤其是醛,排放到大气中,可能遭受气溶胶或云层中水滴的水合作用。同时,它们可以与羟基自由基反应,羟基自由基可以从这些物种中添加或提取氢原子。使用密度泛函和量子复合理论方法研究了水合与氢提取之间的相互作用,在气相和模拟散装水中。从甲醛的醛和二元醇形式中提取H,乙醛,乙醇醛,乙二醛,甲基乙二醛,和丙烯醛进行了研究,以确定取代基对一种形式或另一种形式的抽象的偏好是否有任何明显的影响。发现在甲醛的情况下,与羰基相邻的H原子的提取比从双元二醇的相同提取产生更稳定的自由基,乙醛,和乙醇醛。在Cα中存在离域基团(乙二醛和甲基乙二醛中的羰基,和丙烯醛中的乙烯基),扭转了这种趋势,现在从双元二醇中提取H原子会产生更稳定的自由基。进行了进一步的研究,从所考虑的物种中的其他不同位置提取氢原子,醛和双元二醇形式。只有在乙醇醛的情况下,通过从-CH2OH基团提取H形成的自由基比任何其他自由基物种更稳定。对二元醇中的一个羟基中的氢原子的提取等同于向醛中添加·OH基团。它导致了,在某些情况下,分解成一个较小的自由基和一个中性分子。在这些情况下,在气相和(模拟)本体溶剂中的结果之间观察到一些有趣的理论差异,以及所选择的计算方法。
    方法:DFT(M06-2X,B2PLYP,PW6B95),CCSD(T),和复合材料(CBS-QB3,Jun-ChS,SCVECV-f12)使用Dunning基集和外推至CBS极限的方法来研究酮基和二元醇形式的闭壳醛的能量学,以及通过氢提取从它们衍生的自由基。进行了气相和模拟本体溶剂计算,在最后一种情况下使用可极化连续体模型。
    BACKGROUND: Carbonyl compounds, especially aldehydes, emitted to the atmosphere, may suffer hydration in aerosols or water droplets in clouds. At the same time, they can react with hydroxyl radicals which may add or abstract hydrogen atoms from these species. The interplay between hydration and hydrogen abstraction is studied using density functional and quantum composite theoretical methods, both in the gas phase and in simulated bulk water. The H-abstraction from the aldehydic and geminal diol forms of formaldehyde, acetaldehyde, glycolaldehyde, glyoxal, methylglyoxal, and acrolein is studied to determine whether the substituent has any noticeable effect in the preference for the abstraction of one form or another. It is found that abstraction of the H-atom adjacent to the carbonyl group gives a more stable radical than same abstraction from the geminal diol in the case of formaldehyde, acetaldehyde, and glycolaldehyde. The presence of a delocalizing group in the Cα (a carbonyl group in glyoxal and methylglyoxal, and a vinyl group in acrolein), reverts this trend, and now the abstraction of the H-atom from the geminal diol gives more stable radicals. A further study was conducted abstracting hydrogen atoms from the other different positions in the species considered, both in the aldehydic and geminal diol forms. Only in the case of glycolaldehyde, the radical formed by H-abstraction from the -CH2OH group is more stable than any of the other radical species. Abstraction of the hydrogen atom in one of the hydroxyl groups in the geminal diol is equivalent to the addition of the •OH radical to the aldehyde. It leads, in some cases, to decomposition into a smaller radical and a neutral molecule. In these cases, some interesting theoretical differences are observed between the results in gas phase and (simulated) bulk solvent, as well as with respect to the method of calculation chosen.
    METHODS: DFT (M06-2X, B2PLYP, PW6B95), CCSD(T), and composite (CBS-QB3, jun-ChS, SCVECV-f12) methods using Dunning basis sets and extrapolation to the CBS limit were used to study the energetics of closed shell aldehydes in their keto and geminal-diol forms, as well as the radical derived from them by hydrogen abstraction. Both gas phase and simulated bulk solvent calculations were performed, in the last case using the Polarizable Continuum Model.
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  • 文章类型: Journal Article
    背景:羰基应力,一种代谢状态,其特征是反应性羰基化合物(RCC)的产生增加,与氧化应激密切相关,并与各种疾病有关。本研究旨在调查无药物双相情感障碍(BD)患者与健康对照的羰基应激参数,探索它们与临床特征的关系,并评估治疗对这些参数的影响。
    方法:招募初步诊断为BD躁狂发作的患者和健康对照。排除标准包括智力障碍,神经系统疾病的存在,慢性疾病,如糖尿病和代谢综合征,和炎症的临床症状。使用高效液相色谱法测定血清羰基应激参数的水平。
    结果:治疗前后患者的乙二醛(GO)和甲基乙二醛(MGO)水平没有差异,但治疗后丙二醛(MDA)水平显着降低。治疗前MGO和MDA水平高于对照组,这些差异在治疗后仍然存在。调整BMI和腰围后,与对照组相比,患者中只有MDA水平显著高于对照组.
    结论:该研究的局限性包括排除女性患者,排除了对潜在性别差异的任何评估,以及缺乏对特定情绪稳定剂或抗精神病药物作用的分析。
    结论:这项研究首次关注BD中的羰基应激标志物,特别是GO,MGO,和MDA。患者的MDA水平仍然明显较高,提示在BD病理生理学中的潜在作用。MGO水平受代谢参数的影响,表明与BD神经毒性的潜在联系。需要对更大的队列进行进一步的研究,以更好地了解RCCs在BD中的作用及其作为治疗靶标的潜力。
    BACKGROUND: Carbonyl stress, a metabolic state characterized by elevated production of reactive carbonyl compounds (RCCs), is closely related to oxidative stress and has been implicated in various diseases. This study aims to investigate carbonyl stress parameters in drug-free bipolar disorder (BD) patients compared to healthy controls, explore their relationship with clinical features, and assess the effect of treatment on these parameters.
    METHODS: Patients with a primary diagnosis of a manic episode of BD and healthy controls were recruited. Exclusion criteria included intellectual disability, presence of neurological diseases, chronic medical conditions such as diabetes mellitus and metabolic syndrome, and clinical signs of inflammation. Levels of serum carbonyl stress parameters were determined using high-performance liquid chromatography.
    RESULTS: Levels of glyoxal (GO) and methylglyoxal (MGO) did not differ between pre- and post-treatment patients, but malondialdehyde (MDA) levels decreased significantly post-treatment. Pre-treatment MGO and MDA levels were higher in patients compared to controls, and these differences persisted post-treatment. After adjusting for BMI and waist circumference, only MDA levels remained significantly higher in patients compared to controls.
    CONCLUSIONS: The study\'s limitations include the exclusion of female patients, which precluded any assessment of potential gender differences, and the lack of analysis of the effect of specific mood stabilizers or antipsychotic drugs.
    CONCLUSIONS: This study is the first to focus on carbonyl stress markers in BD, specifically GO, MGO, and MDA. MDA levels remained significantly higher in patients, suggesting a potential role in BD pathophysiology. MGO levels were influenced by metabolic parameters, indicating a potential link to neurotoxicity in BD. Further research with larger cohorts is needed to better understand the role of RCCs in BD and their potential as therapeutic targets.
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  • 文章类型: Journal Article
    烘焙过程有可能产生健康风险化合物,包括来自脂质氧化和美拉德反应的产物。羟甲基糠醛(HMF)的消化前后水平,丙二醛(MDA),乙二醛(GO),和甲基乙二醛(MGO)在用榛子和葵花籽油配制的蛋糕中进行了研究,以及他们的油凝胶作为人造黄油的替代品。与用人造黄油配制的蛋糕相比,在消化后,油和油凝胶配制的蛋糕中HMF的浓度增加。在消化之前,在油和油凝胶配制的饼中,MDA值在82和120μg/100g之间,并且在消化之后观察到降低。用油和油凝胶代替人造黄油导致在蛋糕中产生大量的GO和MGO。然而,在用人造黄油配制的GO蛋糕中发现了最高的生物可及性,为318.2%。由于HMF的形成,与人造黄油相比,油凝胶可能不会带来潜在的健康益处,MDA,GO,和MGO。
    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.
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  • 文章类型: Journal Article
    这项研究的目的是评估模拟消化对巧克力中α-二羰基化合物(α-DC)形成的影响。为此,通过高效液相色谱(HPLC)分析在体外消化前后测定巧克力中乙二醛和丙酮醛的浓度。初始浓度范围从0.0到228.2微克/100克,乙二醛和甲基乙二醛为0.0和555.1,分别。消化后,乙二醛和甲基乙二醛水平均显着增加,达到1804%和859%,分别。研究结果表明,消化系统条件促进了糖基化终产物(AGE)前体的形成。此外,发现含有黑巧克力的巧克力样品中的乙二醛和甲基乙二醛水平较低。相比之下,发现它们含有丰富的榛子样本,杏仁,Pistache,和牛奶。进一步的研究应集中在消化系统条件下α-DCs的形成。包括结肠,来确定肠道微生物群的影响。
    The objective of this study was to assess the effects of simulated digestion on the formation of α-dicarbonyl compounds (α-DCs) in chocolates. For that purpose, the concentrations of glyoxal and methylglyoxal in chocolates were determined through High-Performance Liquid Chromatography (HPLC) analysis before and after in vitro digestion. The initial concentrations ranged from 0.0 and 228.2 µg/100 g, and 0.0 and 555.1 for glyoxal and methylglyoxal, respectively. Following digestion, there was a significant increase in both glyoxal and methylglyoxal levels, reaching up to 1804 % and 859 %, respectively. The findings indicate that digestive system conditions facilitate the formation of advanced glycation end product (AGE) precursors. Also, glyoxal and methylglyoxal levels were found to be low in chocolate samples containing dark chocolate. In contrast, they were found to be high in samples containing hazelnuts, almonds, pistache, and milk. Further studies should focus on α-DCs formation under digestive system conditions, including the colon, to determine the effects of gut microbiota.
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  • 文章类型: Journal Article
    为了从源头上减少甲醛基粘合剂中挥发性有机化合物(VOCs)的释放,使用低毒性和可生物降解的乙二醛代替甲醛来制备新型脲-乙二醛树脂是一种简单且有前途的策略。新型尿素-乙二醛树脂(UG)的耐水性和粘合强度有限,限制了其广泛应用。本研究准备了一种高性能,通过将UG预聚物与小麦面筋蛋白(WP)结合使用的耐水WP-UG木材粘合剂。FTIR,XRD,XPS证实了这两种成分之间存在化学反应,热分析表明,WP-UG胶合板具有较好的热稳定性。对胶合性能的评估表明,WP-UG胶粘胶合板的干强度和湿强度分别达到1.39和0.87MPa,分别,显著高于UG树脂的35%和314%。在63℃水中浸泡3h后,粘结强度从0增加到0.89MPa。结果表明,WP的引入促进了更复杂和紧密堆积的交联网络的形成,并开发了具有高粘结强度和耐水性的乙二醛基粘合剂。本研究为新型脲甲醛粘合剂替代有害甲醛基粘合剂提供了一条新的绿色途径,这有助于提高其在木材行业的潜在应用价值。
    To reduce the release of volatile organic compounds (VOCs) from formaldehyde-based adhesives at the source, the use of low-toxicity and biodegradable glyoxal instead of formaldehyde for the preparation of novel urea-glyoxal resins is a simple and promising strategy. The limited water resistance and adhesive strength of the new urea-glyoxal resins (UG) restrict their extensive application. This study prepared a high-performance, water-resistant WP-UG wood adhesive by combining UG prepolymer with wheat gluten protein (WP). FTIR, XRD, and XPS confirmed the existence of a chemical reaction between the two components, and thermal analysis showed that WP-UG plywood had better thermal stability. Evaluation of the gluing properties revealed that the dry and wet strengths of WP-UG adhesive bonded plywood reached 1.39 and 0.87 MPa, respectively, which were significantly higher than those of UG resin by 35 % and 314 %. The bond strength increased from 0 to 0.89 MPa after immersion in water at 63 °C for 3 h. The results indicated that the introduction of WP promoted the formation of a more complex and tightly packed crosslinking network and developed a glyoxal-based adhesive with high bond strength and water resistance. This study provides a new green pathway for novel urea-formaldehyde binders to replace harmful formaldehyde-based binders, which helps to increase their potential application value in the wood industry.
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  • 文章类型: Journal Article
    巴氏灭菌和喷雾干燥是确保配方产品安全性和保质期的关键步骤。但这些处理也诱导一些潜在有害的美拉德反应产物的形成。在这项研究中,分析了不同商业配方中潜在有害的美拉德反应产物和近似组成的发生。我们的结果表明,婴儿配方奶粉中的糠氨酸浓度明显较高,Nε-(羧甲基)赖氨酸(CML)和Nε-(羧乙基)赖氨酸(CEL)比后续/幼儿配方。特殊配方的乙二醛和CML浓度高于其他类型的配方。相关分析表明,5-羟甲基糠醛的浓度,3-脱氧葡萄糖酮,CML和CEL与脂肪含量密切相关。这些结果提供了对不同类型配方中潜在有害的美拉德反应产物浓度的了解,并为进一步优化加工提供了理论基础。
    Pasteurisation and spray drying are critical steps to ensure the safety and shelf-life of formulae, but these treatments also induce formation of some potentially harmful Maillard reaction products. In this study, the occurrence of potentially harmful Maillard reaction products and proximate compositions in different commercial formulae were analysed. Our results showed that infant formulae had significantly higher concentrations of furosine, Nε-(carboxymethyl)lysine (CML) and Nε-(carboxyethyl)lysine (CEL) than follow-on/toddler formula. Specialty formulae had higher concentrations of glyoxal and CML than other types of formulae. Correlation analysis indicated that concentrations of 5-hydroxymethylfurfural, 3-deoxyglucosone, CML and CEL were closely related to fat contents. These results provided insight into concentrations of potentially harmful Maillard reaction products in different types of formulae and provide a theoretical basis for further optimisation of processing.
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  • 文章类型: Journal Article
    丙烯醛(ACR),甲基乙二醛(MGO),乙二醛(GO)是一类反应性羰基(RCS),在慢性和年龄相关疾病的发病机制中起着至关重要的作用。这里,我们探索了一种新的RCS抑制剂(茶氨酸,THE),并通过人体实验研究了其在体内对RCS的捕获能力。证明茶氨酸在模拟生理条件下通过形成加合物可以有效捕获ACR而不是MGO/GO,我们在食用茶氨酸胶囊(200和400毫克)或绿茶(4杯,含有200毫克茶氨酸),使用超高效液相色谱-飞行时间-高分辨率质谱。定量分析显示,THE-ACR,THE-2ACR-1,THE-MGO,和THE-GO在茶氨酸胶囊组中以剂量依赖性方式形成;还测试了茶氨酸加合物的最大值。此外,除了茶氨酸的RCS加合物,在饮茶组中也可以检测到儿茶素的RCS加合物。然而,代谢物谱分析表明茶氨酸比儿茶素能更好地捕获肾代谢途径中产生的RCS。我们的发现表明,茶氨酸可以通过两种方式减少体内的RCS:作为纯成分或包含在茶叶中。
    Acrolein (ACR), methylglyoxal (MGO), and glyoxal (GO) are a class of reactive carbonyl species (RCS), which play a crucial role in the pathogenesis of chronic and age-related diseases. Here, we explored a new RCS inhibitor (theanine, THE) and investigated its capture capacity on RCS in vivo by human experiments. After proving that theanine could efficiently capture ACR instead of MGO/GO by forming adducts under simulated physiological conditions, we further detected the ACR/MGO/GO adducts of theanine in the human urine samples after consumption of theanine capsules (200 and 400 mg) or green tea (4 cups, containing 200 mg of theanine) by using ultraperformance liquid chromatography-time-of-flight-high-resolution mass spectrometry. Quantitative assays revealed that THE-ACR, THE-2ACR-1, THE-MGO, and THE-GO were formed in a dose-dependent manner in the theanine capsule groups; the maximum value of the adducts of theanine was also tested. Furthermore, besides the RCS adducts of theanine, the RCS adducts of catechins could also be detected in the drinking tea group. Whereas, metabolite profile analysis showed that theanine could better capture RCS produced in the renal metabolic pathway than catechins. Our findings indicated that theanine could reduce RCS in the body in two ways: as a pure component or contained in tea leaves.
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  • 文章类型: Journal Article
    这项研究旨在更好地了解晚期糖基化终产物(AGEs)的反应性1,2-二羰基前体是否以及如何,乙二醛(GO)和甲基乙二醛(MGO),通过研究它们在体外Caco-2transwell系统中的运输来穿越肠屏障。结果表明,GO,MGO和Nε-(羧甲基)赖氨酸(CML),后者进行了比较研究,通过主动和被动运输穿过肠细胞层,并在细胞中积累,虽然都在有限的程度上。此外,二羰基化合物的运输仅部分受到氨基酸和蛋白质的影响,这表明通过食物基质清除不会完全阻止它们的肠道吸收。我们的研究为两种主要食源性二羰基AGE前体的吸收提供了新的见解,并提供了其潜在的全身生物利用度的证据,以及限制其对整体暴露的贡献的因素。
    This study aimed to better understand whether and how the reactive 1,2-dicarbonyl precursors of advanced glycation end products (AGEs), glyoxal (GO) and methylglyoxal (MGO), cross the intestinal barrier by studying their transport in the in vitro Caco-2 transwell system. The results reveal that GO, MGO and Nε-(carboxymethyl)lysine (CML), the latter studied for comparison, are transported across the intestinal cell layer via both active and passive transport and accumulate in the cells, albeit all to a limited extent. Besides, the transport of the dicarbonyl compounds was only partially affected by the presence of amino acids and protein, suggesting that scavenging by a food matrix will not fully prevent their intestinal absorption. Our study provides new insights into the absorption of the two major food-borne dicarbonyl AGE precursors and provides evidence of their potential systemic bioavailability but also of factors limiting their contribution to the overall exposome.
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