aldehydes

醛类
  • 文章类型: Journal Article
    由于缺乏类似于肉类的特征风味,基于植物的肉类替代品的感官特性不能满足消费者的期望。为了应对这一挑战,开发了一种利用Laetigorussulfureus的发酵系统,以从蔬菜来源产生类似肉类和脂肪的味道,洋葱。通过多搅拌棒吸附萃取和气相色谱-质谱-嗅觉测定法,不饱和醛,(E,Z)-2,4-癸二烯醛,赋予动物脂类和脂肪的气味,和含硫化合物苯并噻唑,带有肉汤般的气味,这很好地促成了上清液的特征气味。(E,Z)-2,4-Decadienal作为最重要的气味剂(气味活性值=206)是通过用L.sulfureus转化亚油酸而生物合成的,正如同位素示踪实验所揭示的。第一次在担子菌,(E,提出了由亚油酸制成的Z)-2,4-癸二烯醛。
    The organoleptic properties of plant-based meat alternatives do not meet consumer expectations due to the lack of characteristic flavors resembling meat. To address this challenge, a fermentation system utilizing Laetiporussulphureus was developed to generate a meat-like and fatty flavor from a vegetable source, onion. By means of multiple stir bar sorptive extraction and gas chromatography-mass spectrometry-olfactometry, an unsaturated aldehyde, (E,Z)-2,4-decadienal, which imparts a tallow-like and fatty odor, and a sulfurous compound benzothiazole, with a broth-like odor were identified, which well contributed to the characteristic odor of the supernatant. (E,Z)-2,4-Decadienal as the most important odorant (odor activity value = 206) was biosynthesized by transformation of linoleic acid with L.sulphureus, as revealed by isotopic tracing experiments. For the first time in Basidiomycota, the biogenetic pathway of (E,Z)-2,4-decadienal from linoleic acid was proposed.
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  • 文章类型: Journal Article
    这项研究旨在评估氨基酸作为脂质抗氧化剂在减少煎炸油中挥发性醛形成方面的作用。蛋氨酸,组氨酸,将浓度为2.5、5和10mM的甘氨酸添加到高油酸葵花籽油(HOSO)中,以研究它们对饱和葵花籽油的分布和形成的影响,单不饱和,和多不饱和挥发性醛。结果表明,饱和挥发性醛的比例大于不饱和挥发性醛的比例;蛋氨酸的抑制作用最好,油炸12小时后,10mM蛋氨酸使饱和挥发性醛的含量降低24.21%,单不饱和52.4%,与对照相比,多不饱和脂肪酸降低了54.73%。蛋氨酸的含硫侧链也被证明具有很强的抗氧化活性。结合本研究的结果,这也可以为使用氨基酸作为脂质抗氧化剂提供见解。
    This research aims to assess the effect of amino acids as lipid antioxidants in reducing the formation of volatile aldehydes in frying oil. Methionine, histidine, and glycine at concentrations of 2.5, 5, and 10 mM were added to high oleic sunflower oil (HOSO) to investigate their effects on the distribution and formation of saturated, monounsaturated, and polyunsaturated volatile aldehydes. The results showed that the proportion of saturated volatile aldehydes was greater than that of unsaturated ones; Methionine exhibited the best inhibitory effect, after 12 h of frying, 10 mM methionine reduced the content of saturated volatile aldehydes by 24.21 %, monounsaturated by 52.4 %, and polyunsaturated by 54.73 % compared to the control. Methionine\'s sulfur-containing side chain was also proven to have strong antioxidant activity. Combined with the results of this study, this can also provide insights for using amino acids as lipid antioxidants.
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  • 文章类型: Journal Article
    应用水杨醛衍生物的第一个例子,以及在其结构中C8位置具有甲酰基的香豆素,作为三组分Passerini反应中的羰基伙伴,是presented。作为对Passerini反应条件研究的结果,揭示了在多组分反应过程中使用的水杨醛中羟基的重要作用。当使用具有未保护羟基的醛时,仅获得双组分α-羟基酰胺产物。相比之下,酰化醛的使用产生高效的三组分α-酰氧基酰胺产物。开发的方案以良好的产量获得结构多样化的肽模拟物。还评价了化合物作为抗选择的医院病原菌菌株的抗微生物剂。结构-活性关系表明,抑制活性与香豆素支架的不饱和内酯环中C4位的三氟甲基(CF3)或甲基的存在密切相关。对8个选定的病原菌菌株(革兰氏阳性致病性金黄色葡萄球菌菌株(ATCC23235)进行了MIC和MBC研究,以及革兰氏阴性大肠杆菌(K12(ATCC25404),R2(ATCC39544),R3(ATCC11775),和R4(ATCC39543),鲍曼不动杆菌(ATCC17978),铜绿假单胞菌(ATCC15442),和阴沟肠杆菌(ATCC49141)已经表明,所测试的化合物在低浓度下显示出强的杀菌作用。在所有被调查的特工中,5种表现出比常用抗生素更高的抗菌活性。应该注意的是,所有测试的化合物对金黄色葡萄球菌显示出非常高的活性,这是导致许多死亡的医院感染的主要来源。此外,使用MTT试验对BALB/c3T3小鼠成纤维细胞系测量了16种衍生物的细胞毒性。细胞毒性研究表明,与治疗剂量范围内常用抗生素相比,受试物质对细胞增殖的影响相似或更低。使用环丙沙星的平行MTT测定法,博来霉素,氯唑西林表明,当在哺乳动物细胞中测试时,这些抗生素的细胞毒性更大,细胞活力在85.0-89.9%的范围内。此外,我们已经表明,所研究的基于香豆素的肽模拟物,根据它们的结构特征,是非选择性的,对各种革兰氏阳性和革兰氏阴性病原体有效地发挥作用,这对住院患者非常重要。
    The first example of applying salicylaldehyde derivatives, as well as coumarin with the formyl group at the C8 position in its structure, as carbonyl partners in a three-component Passerini reaction, is presented. As a result of research on the conditions of the Passerini reaction, the important role of the hydroxyl group in the salicylaldehyde used in the course of the multicomponent reaction was revealed. When an aldehyde with an unprotected hydroxyl group is used, only two-component α-hydroxy amide products are obtained. In contrast, the use of acylated aldehyde results in three-component α-acyloxy amide products with high efficiency. The developed protocol gives access to structurally diversified peptidomimetics with good yield. The compounds were also evaluated as antimicrobial agents against selected strains of nosocomial pathogenic bacteria. The structure-activity relationship revealed that inhibitory activity is strongly related to the presence of the trifluoromethyl group (CF3) or the methyl group at the C4 position in an unsaturated lactone ring of the coumarin scaffold. MIC and MBC studies were carried out on eight selected pathogenic bacteria strains (Gram-positive pathogenic Staphylococcus aureus strain (ATCC 23235), as well as on Gram-negative E. coli (K12 (ATCC 25404), R2 (ATCC 39544), R3 (ATCC 11775), and R4 (ATCC 39543)), Acinetobacter baumannii (ATCC 17978), Pseudomonas aeruginosa (ATCC 15442), and Enterobacter cloacae (ATCC 49141) have shown that the tested compounds show a strong bactericidal effect at low concentrations. Among all agents investigated, five exhibit higher antimicrobial activity than those observed for commonly used antibiotics. It should be noted that all the compounds tested showed very high activity against S. aureus, which is the main source of nosocomial infections that cause numerous fatalities. Additionally, the cytotoxicity of sixteen derivatives was measured with the use of the MTT test on BALB/c3T3 mouse fibroblast cell lines. The cytotoxicity studies revealed that the tested substances exert a similar or lower effect on cell proliferation than that observed for commonly used antibiotics within the range of therapeutic doses. A parallel MTT assay using ciprofloxacin, bleomycin, and cloxacillin showed that these antibiotics are more cytotoxic when tested in mammalian cells, and cell viability is in the range of 85.0-89.9%. Furthermore, we have shown that the studied coumarin-based peptidomimetics, depending on their structural characteristics, are nonselective and act efficiently against various Gram-positive and Gram-negative pathogens, which is of great importance for hospitalised patients.
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  • 文章类型: Journal Article
    据报道,用醛葡聚糖修饰固定化乙二酰基-无花果蛋白可以促进空间位阻,从而大大降低固定化蛋白酶对血红蛋白的活性,而蛋白酶仍然保持对酪蛋白的合理活性水平。在本文中,我们研究了这种影响是否可能根据载体上加载的ficin量而有所不同。为此,制备了中等负载和过载的乙二酰基-无花蛋白生物催化剂,并用醛葡聚糖进行了改性。虽然中等负载的生物催化剂具有显著降低的活性,主要针对血红蛋白,过载生物催化剂的活性几乎保持不变。这表明醛葡聚糖能够修饰中等负载的酶的当酶过载时不可用的区域。这种改性促进了两种生物催化剂的生物催化剂稳定性的显着增加,但是过载生物催化剂的稳定性更高(可能是由于分子间和分子内交联的结合)。
    It has been reported that the modification of immobilized glyoxyl-ficin with aldehyde dextran can promote steric hindrances that greatly reduce the activity of the immobilized protease against hemoglobin, while the protease still maintained a reasonable level of activity against casein. In this paper, we studied if this effect may be different depending on the amount of ficin loaded on the support. For this purpose, both the moderately loaded and the overloaded glyoxyl-ficin biocatalysts were prepared and modified with aldehyde dextran. While the moderately loaded biocatalyst had a significantly reduced activity, mainly against hemoglobin, the activity of the overloaded biocatalyst was almost maintained. This suggests that aldehyde dextran was able to modify areas of the moderately loaded enzyme that were not available when the enzyme was overloaded. This modification promoted a significant increase in biocatalyst stability for both biocatalysts, but the stability was higher for the overloaded biocatalyst (perhaps due to a combination of inter- and intramolecular crosslinking).
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  • 文章类型: Journal Article
    在一项具有里程碑意义的研究中,oleocanthal(OLC),特级初榨橄榄油(EVOO)中的主要酚类物质,被发现具有类似于布洛芬的抗炎活性,涉及环氧合酶(COX)酶的抑制。EVOO是生物活性化合物的丰富来源,包括脂肪酸和酚类;然而,仅探索了一小部分与欧洲橄榄相关的化合物的生物学活性。这里,OliveNetTM文库(由600多种化合物组成)用于研究橄榄衍生化合物作为花生四烯酸途径的潜在调节剂.我们的第一个目的是进行酶测定,以评估某些酚类化合物和脂肪酸对COX同工型(COX-1和COX-2)和15-脂氧合酶(15-LOX)的抑制活性。发现橄榄化合物抑制COX亚型,对15-LOX的活性最小。随后的分子对接表明,橄榄化合物对COX亚型的活性位点具有很强的结合亲和力,和分子动力学(MD)模拟证实了结合的稳定性。此外,橄榄化合物被预测具有良好的药代动力学特性,包括准备穿过生物膜,如引导MD模拟和伞形采样所强调的。重要的是,基于膜片钳测定,将包括OLC的橄榄化合物鉴定为人醚-à-go-go相关基因(hERG)通道的非抑制剂。总的来说,这项研究扩展了我们对Olea-europaea衍生化合物的生物活性的理解,其中许多现在已知是,至少在某种程度上,对地中海饮食的有益健康影响负责。
    In a landmark study, oleocanthal (OLC), a major phenolic in extra virgin olive oil (EVOO), was found to possess anti-inflammatory activity similar to ibuprofen, involving inhibition of cyclooxygenase (COX) enzymes. EVOO is a rich source of bioactive compounds including fatty acids and phenolics; however, the biological activities of only a small subset of compounds associated with Olea europaea have been explored. Here, the OliveNetTM library (consisting of over 600 compounds) was utilized to investigate olive-derived compounds as potential modulators of the arachidonic acid pathway. Our first aim was to perform enzymatic assays to evaluate the inhibitory activity of a selection of phenolic compounds and fatty acids against COX isoforms (COX-1 and COX-2) and 15-lipoxygenase (15-LOX). Olive compounds were found to inhibit COX isoforms, with minimal activity against 15-LOX. Subsequent molecular docking indicated that the olive compounds possess strong binding affinities for the active site of COX isoforms, and molecular dynamics (MD) simulations confirmed the stability of binding. Moreover, olive compounds were predicted to have favorable pharmacokinetic properties, including a readiness to cross biological membranes as highlighted by steered MD simulations and umbrella sampling. Importantly, olive compounds including OLC were identified as non-inhibitors of the human ether-à-go-go-related gene (hERG) channel based on patch clamp assays. Overall, this study extends our understanding of the bioactivity of Olea-europaea-derived compounds, many of which are now known to be, at least in part, accountable for the beneficial health effects of the Mediterranean diet.
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  • 文章类型: Journal Article
    非小细胞肺癌(NSCLC)是全球最常见的癌症之一,也是导致癌症相关死亡的主要原因。源自NSCLC的细胞外囊泡(EV)在肺癌进展中起关键作用。我们的发现揭示了EV的丰度与转染效率之间的直接相关性。共培养两种不同的肺癌细胞系可以增强EV的形成,细胞增殖,迁移和致瘤性。mRNA芯片和代谢分析显示,来自共培养细胞的肿瘤组织中FOXO信号通路和不饱和脂肪酸代谢发生了显着变化。猎枪脂质组学研究和生物信息学分析引导我们关注4-羟基壬烯醛(4-HNE)和FOXO4。提高4-HNE或FOXO4水平可以减少EV的形成并阻碍细胞生长和迁移。而沉默FOXO4表达导致细胞克隆率增加和迁移增强。这些发现表明,调节4-HNE和FOXO4的产生可能为NSCLC的治疗提供有效的治疗方法。
    Non-small cell lung cancer (NSCLC) is among the most prevalent cancers and a leading cause of cancer-related mortality globally. Extracellular vesicles (EVs) derived from NSCLC play a pivotal role in lung cancer progression. Our findings reveal a direct correlation between the abundance of EVs and the transfection efficiencies. Co-culturing two different lung cancer cell lines could enhance EVs formation, cell proliferation, migration and tumorigenicity. mRNA chip and metabolic analyses revealed significant alterations in the FOXO signaling pathway and unsaturated fatty acid metabolism within tumor tissues derived from co-cultured cells. Shotgun lipidomics studies and bioinformatics analyses guided our attention towards 4-Hydroxynonenal (4-HNE) and FOXO4. Elevating 4-HNE or FOXO4 levels could reduce the formation of EVs and impede cell growth and migration. While silencing FOXO4 expression lead to an increase in cell cloning rate and enhanced migration. These findings suggest that regulating the production of 4-HNE and FOXO4 might provide an effective therapeutic approach for the treatment of NSCLC.
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  • 文章类型: Journal Article
    三(吡唑基)甲烷(tpm),使用2,2,2-三(吡唑基)乙醇(tpmOH)及其与布洛芬和氟比洛芬(tpmIBU和tpmFLU)的酯化衍生物作为配体,以获得[Fe(tpmX)2]Cl2(1-4)型配合物。tpmIBU和tpmFLU配体以及相应的配合物3和4通过IR和多核NMR光谱进行了表征,通过单晶X射线衍射阐明了tpmIBU的结构。还评估了配合物1-4在水性介质中的行为(在D2O中的溶解度,辛醇/水分配系数,在类似生理条件下的稳定性)。在A2780,A2780cis和A549癌细胞系以及非癌HEK293T和BJ细胞系上确定了配体和复合物的抗增殖活性。研究了配体和复合物抑制COX-2(环氧合酶)和HNE(4-羟基壬烯醛)酶的能力。复合物3和4表现出细胞毒性,这可能主要归因于它们的生物活性片段,而DNA结合和ROS产生的增强似乎没有发挥任何重要作用。
    Tris(pyrazolyl)methane (tpm), 2,2,2-tris(pyrazolyl)ethanol (tpmOH) and its esterification derivatives with ibuprofen and flurbiprofen (tpmIBU and tpmFLU) were used as ligands to obtain complexes of the type [Fe(tpmX)2]Cl2 (1-4). The tpmIBU and tpmFLU ligands and corresponding complexes 3 and 4 were characterized by IR and multinuclear NMR spectroscopy, and the structure of tpmIBU was elucidated by single crystal X-ray diffraction. Complexes 1-4 were also assessed for their behaviour in aqueous media (solubility in D2O, octanol/water partition coefficient, stability in physiological-like conditions). The antiproliferative activity of ligands and complexes was determined on A2780, A2780cis and A549 cancer cell lines and the non-cancerous HEK 293T and BJ cell lines. The ligands and complexes were investigated for their ability to inhibit COX-2 (cyclooxygenase) and HNE (4-hydroxynonenal) enzymes. Complexes 3 and 4 exhibited cytotoxicity that may be attributed predominantly to their bioactive fragments, while DNA binding and enhancement of ROS production do not appear to play any significant role.
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  • 文章类型: Journal Article
    最近,开发了各种基于气味结合蛋白(OBP)的生物传感器,用于检测气味和信息素。然而,关于各种碳数醛的灵敏和选择性检测,存在重要的数据空白。在这项工作中,一种基于OBP2a的电化学阻抗谱(EIS)生物传感器是通过将OBP2a固定在金叉指电极上而开发的,并通过EIS和原子力显微镜进行表征。EIS反应显示基于OBP2a的生物传感器对香茅醛高度敏感,百合醛,octanal,和癸醛(检出限为10-11mol/L),与小分子醇和脂肪酸等干扰气味剂相比,对醛具有选择性(选择性系数低于0.15)。此外,基于OBP2a的生物传感器具有很高的重复性(相对标准偏差:1.6%-9.1%,每种气味剂n=3),稳定性(NIC在第6天下降了3.6%),和回收率(三个实际样品为91.2%-96.6%)。更具体地说,生物传感器对醛的敏感性与气味剂的分子量和杂环分子结构呈正相关。这些结果证明了基于OBP2a的EIS生物传感器的可用性和潜在用途,用于在医学诊断等方面快速和灵敏地检测醛。食物和青睐分析,和环境监测。
    Recently, various biosensors based on odorant-binding proteins (OBPs) were developed for the detection of odorants and pheromones. However, important data gaps exist regarding the sensitive and selective detection of aldehydes with various carbon numbers. In this work, an OBP2a-based electrochemical impedance spectroscopy (EIS) biosensor was developed by immobilizing OBP2a on a gold interdigital electrode, and was characterized by EIS and atomic force microscopy. EIS responses showed the OBP2a-based biosensor was highly sensitive to citronellal, lily aldehyde, octanal, and decanal (detection limit of 10-11 mol/L), and was selective towards aldehydes compared with interfering odorants such as small-molecule alcohols and fatty acids (selectivity coefficients lower than 0.15). Moreover, the OBP2a-based biosensor exhibited high repeatability (relative standard deviation: 1.6%-9.1 %, n = 3 for each odorant), stability (NIC declined by 3.6 % on 6th day), and recovery (91.2%-96.6 % on three real samples). More specifically, the sensitivity of the biosensor to aldehydes was positively correlated to the molecular weight and the heterocyclic molecule structure of the odorants. These results proved the availability and the potential usage of the OBP2a-based EIS biosensor for the rapid and sensitive detection of aldehydes in aspects such as medical diagnostics, food and favor analysis, and environmental monitoring.
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  • 文章类型: Journal Article
    电子尼古丁递送系统(ENDS)气溶胶暴露可以在健康的年轻人和动物中诱导内皮功能障碍(ED)。ENDS溶剂的热降解,丙二醇和植物甘油(PG:VG),产生丰富的甲醛(FA)和其他羰基。因为FA可以激活瞬时受体电位锚蛋白-1(TRPA1)传感器,我们假设ENDS气溶胶中的FA会引起TRPA1介导的变化,包括ED和“呼吸制动”-伤害的生物标志物。为了测试这个,野生型(WT)和TRPA1-null小鼠通过吸入暴露于任一过滤空气,PG:VG衍生的气溶胶,或甲醛(FA,5ppm)。短期暴露于PG:VG和FA在雌性WT中诱导ED,但在雌性TRPA1缺失小鼠中不诱导ED。此外,急性暴露于PG:在WT中VG和FA刺激呼吸制动,但在TRPA1无效的雌性小鼠中没有。FA的尿代谢物(即,N-1,3-噻唑烷-4-甲酸,TCA;N-1,3-噻唑烷-4-羰基甘氨酸,TCG)和单胺通过LC-MS/MS测量。PG:VG和FA暴露显著增加WT和TRPA1缺失小鼠中TCA和TCG的尿排泄。为了确认吸入FA直接导致尿TCA,小鼠暴露于同位素13C-FA气体(1ppm,6h)。13C-FA暴露显着增加了早期收集(0-3h)中13C-TCA的尿液水平,支持吸入FA和TCA之间的直接关系。总的来说,这些数据表明,使用ENDS可能会增加依赖FA的CVD风险,TRPA1和儿茶酚胺,但独立于尼古丁或调味剂。这项研究支持应降低ENDS气溶胶中的FA水平,以减轻使用ENDS的人的CVD风险。
    Electronic Nicotine Delivery Systems (ENDS) aerosol exposures can induce endothelial dysfunction (ED) in healthy young humans and animals. Thermal degradation of ENDS solvents, propylene glycol and vegetable glycerin (PG: VG), generates abundant formaldehyde (FA) and other carbonyls. Because FA can activate the transient receptor potential ankyrin-1 (TRPA1) sensor, we hypothesized that FA in ENDS aerosols provokes TRPA1-mediated changes that include ED and \'respiratory braking\' - biomarkers of harm. To test this, wild-type (WT) and TRPA1-null mice were exposed by inhalation to either filtered air, PG: VG-derived aerosol, or formaldehyde (FA, 5 ppm). Short-term exposures to PG: VG and FA induced ED in female WT but not in female TRPA1-null mice. Moreover, acute exposures to PG: VG and FA stimulated respiratory braking in WT but not in TRPA1-null female mice. Urinary metabolites of FA (ie, N  -1,3-thiazolidine-4-carboxylic acid, TCA; N  -1,3-thiazolidine-4-carbonyl glycine, TCG) and monoamines were measured by LC-MS/MS. PG: VG and FA exposures significantly increased urinary excretion of both TCA and TCG in both WT and TRPA1-null mice. To confirm that inhaled FA directly contributed to urinary TCA, mice were exposed to isotopic 13C-FA gas (1 ppm, 6 h).13C-FA exposure significantly increased the urine level of 13C-TCA in the early collection (0-3 h) supporting a direct relationship between inhaled FA and TCA. Collectively, these data suggest that ENDS use may increase CVD risk dependent on FA, TRPA1, and catecholamines, yet independently of either nicotine or flavorants. This study supports that levels of FA in ENDS-derived aerosols should be lowered to mitigate CVD risk in people who use ENDS.
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  • 文章类型: Journal Article
    本文开发了一种基于三嗪骨架的钳形钴配合物催化的频哪醇硼烷还原醛的方法。所提出的方法允许在温和条件下转化具有多种吸电子和给电子基团的几种醛。所提出的程序允许将获得的中间体直接一步水解为相应的伯醇。提出了一种合理的反应机理。
    A method for the reduction of aldehydes with pinacolborane catalyzed by pincer cobalt complexes based on a triazine backbone is developed in this paper. The presented methodology allows for the transformation of several aldehydes bearing a wide range of electron-withdrawing and electron-donating groups under mild conditions. The presented procedure allows for the direct one-step hydrolysis of the obtained intermediates to the corresponding primary alcohols. A plausible reaction mechanism is proposed.
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