heterocyclic amine

杂环胺
  • 文章类型: Journal Article
    2-氨基-1-甲基-6-苯基咪唑[4,5-b]吡啶(PhIP),杂环胺(HAA),在高温下加热的肉制品中发现。然而,PhIP是一种诱变和潜在的致癌化合物。决明子精液,一种药食同源植物,在中国含量丰富,用于抑制杂环胺的应用较少。
    为了在模型系统中研究决明子提取物对PhIP形成的抑制作用并阐明其抑制机制,采用70%乙醇的超声波辅助法获得决明子精液提取物,将其添加到模型系统中(0.6mmol苯丙氨酸:肌酐,1:1).通过LC-MS分析PhIP以确定抑制作用。通过将提取物添加到苯乙醛的模型混合物中,验证了该系统的副产物和PhIP抑制的机理,苯乙醛和肌酐.
    结果表明,随着决明子提取物浓度的增加,PhIP产量降低,最高抑制率为91.9%。副产品(E),在苯丙氨酸和肌酐模型系统中检测到质荷比为m/z199.9,但在其他系统中未检测到。决明子精液提取物可能与苯丙氨酸反应产生副产物(E),这防止了苯丙氨酸通过Strecker反应降解产生苯乙醛。
    决明子精液提取物消耗苯丙氨酸,这是PhIP的前身,从而抑制苯乙醛的形成并最终抑制PhIP的形成。本研究的主要目的是阐明决明子精液抑制PhIP形成的机制,并为实际控制措施建立理论和科学依据。
    UNASSIGNED: 2-Amino-1-methyl-6-phenylimidazole [4,5-b] pyridine (PhIP), a heterocyclic amine (HAA), is found in meat products heated at high temperatures. However, PhIP is a mutagenic and potential carcinogenic compound. Cassiae semen, a type of medicine and food homology plant, is abundant in China and has been less applied for inhibiting heterocyclic amines.
    UNASSIGNED: To investigate the inhibitory effect of cassiae semen extract on PhIP formation within a model system and elucidate the inhibitory mechanism, an ultrasonic-assisted method with 70% ethanol was used to obtain cassiae semen extract, which was added to a model system (0.6 mmol of phenylalanine: creatinine, 1:1). PhIP was analyzed by LC-MS to determine inhibitory effect. The byproducts of the system and the mechanism of PhIP inhibition were verified by adding the extract to a model mixture of phenylacetaldehyde, phenylacetaldehyde and creatinine.
    UNASSIGNED: The results indicated that PhIP production decreased as the concentration of cassiae semen extract increased, and the highest inhibition rate was 91.9%. Byproduct (E), with a mass-charge ratio of m/z 199.9, was detected in the phenylalanine and creatinine model system but was not detected in the other systems. The cassiae semen extract may have reacted with phenylalanine to produce byproduct (E), which prevented the degradation of phenylalanine by the Strecker reaction to produce phenylacetaldehyde.
    UNASSIGNED: Cassiae semen extract consumed phenylalanine, which is the precursor for PhIP, thus inhibiting the formation of phenylacetaldehyde and ultimately inhibiting PhIP formation. The main objective of this study was to elucidate the mechanism by which cassiae semen inhibit PhIP formation and establish a theoretical and scientific foundation for practical control measures.
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  • 文章类型: Journal Article
    本研究旨在研究脱皮芝麻含水率对芝麻酱香气形成及有害物质的影响。SP样品由水分含量为5%的去壳芝麻种子制成,10%,15%,20%,和25%,分别表示为T5、T10、T15、T20和T25。结果表明,调整水分含量对香气化合物有显著影响,颜色强度,和感官特性。预先调节至10%的含水量的SP表现出最小的L*值和最高的褐变强度。使用气相色谱-嗅觉-质谱分析,研究人员在SP中鉴定出38种芳香活性化合物,吡嗪是最丰富的,有助于烤芝麻和坚果的香气。此外,吡咯和呋喃衍生物的存在导致焦糖和杏仁的香气增强,积极影响整体感官特性。T10显示出最高水平的烤芝麻和坚果气味。此外,水分含量的调节也影响了有害化合物的形成,如杂环胺和多环芳烃(PAHs)。值得注意的是,由水分含量为10%和15%的芝麻种子制成的样品显示出最低的PAHs总含量(18.21-28.91ng/g)和PAH4含量(不可检测-0.15ng/g)。在任何样品中均未检测到致癌物苯并[a]芘,确保产品更安全。预先调整SP中的水分含量似乎是改善其风味和安全质量的有希望的方法。
    This study aimed to investigate the influence of the moisture content of dehulled sesame seeds on the aroma formation and harmful substances in sesame paste (SP). The SP samples were made of dehulled sesame seeds with moisture contents of 5%, 10%, 15%, 20%, and 25% and denoted as T5, T10, T15, T20, and T25, respectively. The results revealed that adjusting the moisture content had a significant impact on aroma compounds, color intensity, and sensory properties. SP pre-adjusted to a moisture content of 10% exhibited the smallest L* value and the highest browning strength. Using gas chromatography-olfactometry-mass spectrometry analysis, the researchers identified 38 aroma-active compounds in the SP, with pyrazines being the most abundant, contributing to roasted sesame and nutty aromas. Additionally, the presence of pyrrole and furan derivatives led to enhanced caramel and almond aromas, positively influencing the overall sensory properties. T10 demonstrated the highest levels of roasted sesame and nutty odors. Furthermore, the regulation of moisture content also affected the formation of harmful compounds, such as heterocyclic amines and polycyclic aromatic hydrocarbons (PAHs). Notably, the sample made of the sesame seeds with 10% and 15% moisture content exhibited the lowest total PAHs content (18.21-28.91 ng/g) and PAH4 content (non-detectable-0.15 ng/g). The carcinogen benzo[a]pyrene was not detected in any of the samples, ensuring a safer product. The pre-adjustment of moisture content in SP appears to be a promising approach to improve both its flavor and safety qualities.
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  • 文章类型: Journal Article
    在这项研究中,研究了水分含量(5-25%)对芝麻酱(SP)中有害物质和香气化合物的影响。结果表明,预调节水含量减少了SP中有害物质的产生。值得注意的是,SP-15中的总杂环胺含量显着低于其他样品。SP-10的总多环芳烃含量最低,而SP-5表现出最低的PAH4含量。使用溶剂辅助香气蒸发和GC-O-MS,在SP中鉴定出50种芳香化合物。SP中水含量的预调节导致杂环化合物的浓度升高,从而赋予不同的芳族特征。它增强了烤芝麻和咸糕点香气的感知强度,同时降低了发酵和烧焦香气的感知强度。研究结果表明,水分含量的预先调节在SP的香气调节和有害物质控制中起着至关重要的作用。
    In this study, the influence of pre-regulation of the water content (5-25 %) on the harmful substances and aroma compounds of sesame paste (SP) was investigated. The results indicated that pre-regulation of the water content reduced the generation of harmful substances in SP. Notably, the total heterocyclic amine content in SP-15 was significantly lower than in other samples. SP-10 had the lowest total polycyclic aromatic hydrocarbon content, while SP-5 exhibited the lowest PAH4 content. Using solvent-assisted aroma evaporation and GC-O-MS, 50 aroma compounds were identified in SP. Pre-regulation of water content in SP led to an elevated concentration of heterocyclic compounds thereby imparting a diverse aromatic profile. It enhanced the perceived intensity of roasted sesame and salty pastry aromas while reducing the perceived intensity of fermentation and burnt aromas. The findings suggested the pre-regulation of the water content played a crucial role in aroma modulation and harmful substances control in SP.
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  • 文章类型: Journal Article
    在这项研究中,回顾性分析癌症患者(n=1155)的10年饮食习惯,以及饮食之间的关系(红肉,白肉,鱼肉,炸薯条,面包,速溶咖啡,即饮咖啡,土耳其咖啡,和红茶)杂环胺,多环芳烃,丙烯酰胺,对基于N-亚硝胺的风险评分和癌症类型进行统计学评估。平均饮食热处理污染物风险得分最高和最低的食物是红肉和即饮咖啡,分别。根据癌症患者的人口统计学特征(性别,年龄,吸烟,和体重指数)(p<0.05)。根据癌症的类型,饮食热处理污染物风险评分最高和最低的系统被确定为其他(大脑,甲状腺,淋巴恶性肿瘤,皮肤,口部和下咽,和血液学)和生殖(乳房,子宫,和卵巢)系统,分别。速溶咖啡消费与呼吸系统癌症类型之间的关系,确定了薯条和泌尿系统癌症类型的消费频率以及肉制品和胃肠道系统癌症类型的消费频率。据认为,这项研究包含有关饮食习惯与癌症之间关系的重要发现,并且将成为在这种情况下进行的其他研究的良好来源。
    In this study, the 10-year dietary habits of patients diagnosed with cancer (n = 1155) were retrospectively analyzed, and the relationships between dietary (red meat, white meat, fish meat, French fries, bread, instant coffee, ready-to-drink coffee, Turkish coffee, and black tea) heterocyclic amines, polycyclic aromatic hydrocarbons, acrylamide, and N-nitrosamine-based risk scores and cancer types were statistically evaluated. The foods with the highest and lowest mean dietary heat-treatment contaminant risk scores were red meat and ready-to-drink coffee, respectively. There were statistically significant differences in the dietary heat-treatment contamination risk scores based on the cancer patients\' demographic characteristics (sex, age, smoking, and body mass index) (p < 0.05). According to the cancer types, the systems with the highest and lowest dietary heat-treatment contaminant risk scores were determined as other (brain, thyroid, lymphatic malignancies, skin, oro- and hypopharynx, and hematology) and the reproductive (breast, uterus, and ovary) system, respectively. The relationship between instant coffee consumption and respiratory system cancer types, the frequency of consumption of French fries and urinary system cancer types and the consumption of meat products and gastrointestinal system cancer types were determined. It is thought that this study contains important findings regarding the relationship between dietary habits and cancer and will be a good source for other studies to be conducted in this context.
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  • 文章类型: Journal Article
    使用HPLC和主成分分析,通过添加(0.02%)叔丁基对苯二酚(TBHQ)和(0.05%)乙醇提取的肉豆蔻(ENE)来鉴定和抑制泛烤牛肉饼中的诱变和致癌杂环胺(HCA)。十个HCA,包括六个极性和四个非极性,被评估。添加(0.05%)ENE显着(P<0.05)减少了烹饪过程中馅饼的烹饪损失和收缩,并减少了73.97%的总形成HCA,与TBHQ相比,这证明了作为天然抗氧化剂对脂质氧化和HCA形成的显着(P<0.05)抑制作用。DPPH自由基清除活性,总酚含量,并估算了ENE的可用活性代谢物。此外,pH值之间呈正相关,硫代巴比妥酸反应性物质的水平,和两组的HCA形成。TBHQ和ENE是显著的HCAs抑制剂(P<0.001),但ENE在冷藏储存过程中表现出弹性氧化稳定性。因此,ENE可用于减少平烤牛肉饼中的HCA形成。
    Identification and inhibition of mutagenic and carcinogenic heterocyclic amines (HCAs) from pan-roasted beef patties were performed by adding (0.02%) tertiary butyl hydroquinone (TBHQ) and (0.05%) ethanol-extracted nutmeg (ENE) using HPLC and principal component analysis. Ten HCAs, including six polar and four non-polar, were assessed. The addition of (0.05%) ENE significantly (P < 0.05) reduced the cooking loss and shrinkage of patties during cooking and reduced the total formation HCAs by 73.97%, which proved the significant (P < 0.05) inhibitory effect as a natural antioxidant against lipid oxidation and HCA formation compared to TBHQ. The DPPH radical-scavenging activity, total phenolic content, and available active metabolites of ENE were estimated. Furthermore, a positive correlation was observed between pH, level of thiobarbituric acid reactive substances, and HCA formation in both the groups. TBHQ and ENE were significant HCAs inhibitors (P < 0.001), but ENE showed resilient oxidative stability during refrigeration storage. Therefore, ENE can be used to reduce HCAs formation in pan-roasted beef patties.
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  • 文章类型: Journal Article
    杂环胺(HCA)是富含蛋白质的禽肉在高温下产生的一组致癌物质。花色苷(ACNs)的酶促酰化是提高其稳定性的可靠方法,我们最近发现了酰化的氰化-3-O-葡萄糖(花青素-3-6-肉桂酰基-葡萄糖苷,C3(6C)G)可以有效抑制HCAs的形成,但是下划线机制仍然模糊。因此,本研究调查了C3(6C)G对食物系统(鸡胸肉)中HCA形成的抑制作用,并探讨了潜在的机制。结果表明,不同浓度(0.1、0.5和1.0mg/mL)的C3(6C)G均能显著抑制鸡胸肉肉饼中的脂质氧化,降低烤肉肉饼中的总HCAs含量(P<0.05)。含0.1mg/mLC3(6C)G的样品对总HCAs的抑制作用最好,抑制率为28%,和智商的抑制率,哈曼,TRP-P-2、PhIP和AαC分别为34%,46%,100%,54%和41%,分别。
    Heterocyclic amines (HCAs) are a group of carcinogenic substances produced in protein-rich poultry meat under high-temperature. Enzymatic acylation of anthocyanins (ACNs) is a reliable way to improve their stability, and we recently found the acylated cyaniding-3-O-glucose (cyanidin-3-6-cinnamoyl-glucoside, C3(6C)G) could effective inhibit the HCAs formation, but the underline mechanism was still obscure. Thus, the present study investigated the inhibitory effect ofC3(6C)G on HCAs formation in the food system (chicken breast) and to explore the potential mechanism. The results showed that C3(6C)G with different concentrations (0.1, 0.5 and 1.0 mg/mL) could significantly inhibit lipid oxidation and decrease the total HCAs content (P<0.05) in chicken breast meat patty after roasting. The samples with 0.1 mg/mL C3(6C)G had the best inhibition effect on total HCAs, with an inhibition rate of 28%, and the inhibition rates for IQ, Harman, TRP-P-2, PhIP and AαC were 34%, 46%, 100%, 54% and 41%, respectively.
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  • 文章类型: Journal Article
    表面润湿性对吸附性能的影响很大,催化,和多孔材料的扩散性能。为了实现对亲水性杂环胺(HAs)吸附性能的提高,聚合物高内相乳液(聚HIPEs),可以从疏水性调整到亲水性通过容易地调节金属有机骨架(MOF)的量合成。随着酰胺改性的MOF的量从0%增加到10%,MOF和聚HIPEs杂化物(MOFs@polyHIPEs)的水接触角从133°降低到0°。通过MOFs杂交对二乙烯基苯(DVB)基聚HIPEs进行亲水化,显着提高了其吸附性能,并使其适用于亲水性HAs的固相萃取(SPE)。在优化条件下,MOFs@polyHIPEs通过π-π相互作用和氢键对HAs实现了42.89至86.71µg/g的吸附能力。吸附遵循伪二级动力学模型,咪唑环中/上的氮原子被确定为氢键的活性吸附位点。这种SPE方法,随着HPLC-MS检测,提供的HAs检测限低至0.00020-0.00040ng/mL。这项工作提供了一种可行的策略来调整聚HIPEs的表面润湿性,而无需进行后改性,以实现HAs的高效富集和分析。
    Surface wettability greatly influences the adsorptive, catalytic, and diffuse performances of a porous material. To realize the improved adsorption performance to hydrophilic heterocyclic amines (HAs), polymeric high internal phase emulsions (polyHIPEs) that can be tuned from hydrophobic to hydrophilic is synthesized by facilely regulating the amount of metal organic frameworks (MOFs). The water contact angle of the MOFs and polyHIPEs hybrids (MOFs@polyHIPEs) decreases from 133° to 0° as the amount of amide-modified MOFs increases from 0% to 10%. The hydrophilization of divinybenzene (DVB) based polyHIPEs by MOFs hybridization significantly enhances their adsorption performance and enables them to be suitable for the solid phase extraction (SPE) of hydrophilic HAs. Under the optimized conditions, the MOFs@polyHIPEs achieve adsorption capacities ranging from 42.89 to 86.71 µg/g for HAs through the π-π interaction and hydrogen bonding. The adsorption follows the pseudo-second-order kinetic model, and the nitrogen atoms in/on the imidazole ring are identified as the active adsorption sites for hydrogen bonding. This SPE method, along with HPLC-MS detection, provides detection limits of HAs as low as 0.00020-0.00040 ng/mL. This work offers a feasible strategy in tuning the surface wettability of polyHIPEs without post-modification to achieve high-efficiency enrichment and analysis of HAs.
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  • 文章类型: Journal Article
    杂环胺(HCA)是通过在高温下烹饪产生的蛋白质食品中的污染物。这项研究是首次使用韩国总饮食研究对HCA的暴露进行评估。使用六种同位素标记的内标和HPLC-MS/MS分析了1,232个合并样品中的12个HCA。根据总饮食研究样本中的HCA浓度和来自韩国国家健康和营养检查调查的个人食物消费数据,估计了韩国人口中HCA的每日摄入量。在HCA中,β-咔啉的摄入量,比如Harman和Norharman,是最高的,其次是PhIP的摄入量。HCA摄入的主要来源是肉类,鱼,贝类,和饮料,包括酒精。在韩国人口中,接触PhIP的幅度平均为2,349,000,在第95百分位数为373,000。估计韩国人口中所有HCA的每日摄入量被认为是安全的。
    Heterocyclic amines (HCAs) are contaminants in proteinaceous foods produced by cooking at high temperatures. This study was the first assessment of exposure to HCAs using the Korean total diet study. Twelve HCAs were analysed in 1,232 pooled samples using six isotope-labelled internal standards and HPLC-MS/MS. The daily intake of HCAs in the Korean population was estimated based on the concentration of HCAs in the total diet study samples and individual food consumption data from the Korean National Health and Nutrition Examination Survey. Among HCAs, the intake of β-carbolines, such as harman and norharman, was the highest, followed by the intake of PhIP. The primary sources of HCA intake were meat, fish, shellfish, and beverages, including alcohol. The margin of exposure to PhIP was 2,349,000 at the average level and 373,000 at the 95th percentile in the Korean population. The estimated daily intake of all HCAs in the Korean population was considered safe.
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  • 文章类型: Journal Article
    The effects of different kinds of chitosan, oligomer (ChiO) and monomer (Gluco), and the combinations of polymer (Chi) or ChiO with flavonoid aglycones and glycosides against the formation of major HAs were investigated to find out potential combination partners for enhanced suppression of HA formation. Results in roast beef patties showed ChiO and Gluco significantly inhibited PhIP and MeIQx formation by 43-80% and 31-57%, respectively. Of which, ChiO was the most effective. In combinations with flavonoid glycosides (phloridzin, rutin and hesperidzin, respectively), Chi, but not ChiO, generated enhanced inhibitory effects. Further analysis showed Chi and phloridzin combined at a ratio of 1:1 was the most promising, especially in inhibiting PhIP, and the mechanism behind involved: 1) water retention by Chi, and 2) reduction of phenylalanine availability by phloridzin. These findings suggest that appropriate combination of Chi and flavonoid glycosides contributes to significant improvement in the safety of meat products.
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  • 文章类型: Journal Article
    There are few studies on controlling the formation of heterocyclic amines (HAs) by adding polyphenols to roasted lamb. The aim of this study was to assess the inhibitory effect of 0.025, 0.125, and 0.625 mmol of chlorogenic acid, epicatechin, rutin, quercetin and quinic acid on the formation of HAs in charcoal roasted lamb, respectively, by UHPLC-MS/MS. The results indicated that Harman, Norharman, PhIP, IQx and 8-MeIQx were detected, but both chlorogenic acid and epicatechin greatly inhibited the formation of IQx, 8-MeIQx, Norharman, Harman and PhIP, and epicatechin had better inhibitory effect than chlorogenic acid. PLSR-VID analysis suggested the key precursors of HAs formation in roasted lamb were glucose, ribose, fructose, isoleucine, valine, and lysine. In addition, this work also implied that the potential mechanism of inhibition of HAs formation by chlorogenic acid and epicatechin in roasted lamb might attribute to competitive chemical reactions between polyphenols and key precursors of HAs.
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