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JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY · 2023 · IF 6.1

Mechanism of Carbon Skeleton Formation of 2,3,5-Trimethylpyrazine via a Conversion Reaction between Methylglyoxal and Glyoxal

Wei Jiang,Xiaoyuan Wang,YunJiao Ma,Ming Du,Chao Wu,Xianbing Xu

Maillard flavor compounds, such as 2,3,5-trimethylpyrazine, have been frequently identified in thermally processed food products, such as popcorn and peanuts. However, the origin of the carbon atoms in 2,3,5-trimethylpyrazine has not been clearly elucidated. Herein, a model reaction showed that precursor methylglyoxal and intermediates glyoxal and formaldehyde contributed to the formation of 2,3,5-trimethylpyrazine via a conversion reaction between methylglyoxal and glyoxal. In addition, carbon module labeling technology and model response validation experiments indicated that this transformation reaction between methylglyoxal and glyoxal brought formaldehyde into the methyl group carbon atoms of the 2,3,5-trimethylpyrazine ring. The proposed novel route provides a new perspective for approaches to control the formation of flavor compounds, such as 2,3,5-trimethylpyrazine.

研究领域: 食品科学 · 有机化学
✓ 已验证 产品关联 DOI PubMed 高影响因子
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JOURNAL OF HAZARDOUS MATERIALS · 2018 · IF 6.434

Adducts formed during protein digestion decreased the toxicity of five carbonyl compounds against Caco-2 cells

Kaiyu Jiang,Caihuan Huang,Rui Jiao,Weibin Bai,Jie Zheng,Shiyi Ou

Acrolein (ACR), glyoxal (GO), methylglyoxal (MGO), hydroxymethylfurfural (HMF), and malondialdehyde (MDA) are toxic contaminants for humans. This work aimed to investigate whether intake of proteins can mitigate their toxicity. Simulated gastrointestinal digestion of proteins from pork, chicken, milk powder and soy protein isolate eliminated amount of ACR, GO, MGO, HMF, and MDA. Among six amino acids, cysteine showed highest capacity for elimination of these toxic compounds through the formation of adducts; it reached the highest elimination capacity for GO, MGO, ACR, MDA, and HMF in 40 min at pH 2.0, and 20 min at pH 7.0. The formed adducts between cysteine and GO, MGO, or ACR showed much lower toxicity against Caco-2 cells. Incubation of the cells with 8 mM GO and MGO for 48 h decreased the cell viability to 16.1%, 16.9% respectively; while incubation of the same concentration of their adducts still kept the cell viability at 82.2% and 81.6% respectively. Cysteine showed much higher detoxifying capacity for ACR than GO and MGO, which can lower the toxicity of ACR toward Caco-2 cells by 80 times.

研究领域: 食品科学 · 毒理学 · 细胞生物学
✓ 已验证 DOI PubMed 高影响因子
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JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY · 2024 · IF 5.7

Theanine Capture of Reactive Carbonyl Species in Humans after Consuming Theanine Capsules or Green Tea

Yuqing Zhong,Chen Yang,Yongling Lu,Lishuang Lv

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.

CAS / MDL: 3081-61-6
研究领域: 药理学 · 营养学 · 生物化学 · 代谢组学
✓ 已验证 产品关联 DOI PubMed 高影响因子
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CHINESE JOURNAL OF POLYMER SCIENCE · 2013 ·Vol. 31 ·期 3 ·399-406 · IF 1.27

Facile regulation of glutaraldehyde-modified graphene oxide for preparing free-standing papers and nanocomposite films

Tan Ye-qiang,Song Yi-hu,Zheng Qiang

Colloidal suspensions of glutaraldehyde (GA) crosslinked or grafted graphene oxide (GO) sheets were fabricated by simply tailoring the feed sequence. The different structures were confirmed by Fourier transform infrared spectra and X-ray diffraction. As demonstration of the utilities, the different colloidal suspensions were used to prepare free-standing papers by flow-directed filtration and poly(vinyl alcohol) (PVA)-based nanocomposite films by casting. Free-standing papers from GA crosslinked GO sheets exhibited better mechanical properties than unmodified GO paper, while nanocomposite films from GA grafted GO exhibit higher tensile strength and Young’s modulus.

研究领域: 材料科学 · 纳米技术 · 高分子化学
✓ 已验证 DOI 高影响因子
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Food & Function · 2014 ·Vol. 6 ·期 2 ·584-589 · IF 2.907

Inhibitory effect of leonurine on the formation of advanced glycation end products

Lianqi Huang,Xin Yang,Anlin Peng,Hui Wang,Xiang Lei,Ling Zheng,Kun Huang

Long-term hyperglycemia is a typical symptom of diabetes mellitus (DM) which can cause a high level of protein glycation and lead to the formation of advanced glycation end products (AGEs). The accumulation of AGEs in turn deteriorates DM and its complications. Insulin, the only hormone that directly decreases blood sugar in vivo, is vulnerable to glycation which causes the loss of its biological activity. In this study, we used a porcine insulin (PI)–methylglyoxal (MGO) model to investigate the inhibitory effect of leonurine (LN), a natural alkaloid extracted from Herba leonuri, on AGE formation. Assays including AGE-specific fluorescence, and fructosamine level and carbonyl group content determination showed that LN can dose-dependently suppress PI glycation. A significantly decreased cross-linking level on the glycated PI was also proven by SDS-PAGE electrophoresis. A further liquid chromatography-mass spectrometry study suggested that LN may inhibit PI glycation through trapping MGO and keeping it from reacting with PI. Our results thus indicate that LN is a promising anti-glycation agent for the prevention of diabetes and its complications via inhibiting AGE formation.

研究领域: 药理学 · 糖尿病研究
✓ 已验证 产品关联 DOI PubMed 高影响因子
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Food Bioscience · 2024 · IF 4.8

Protein glycosylation inhibitory effects and mechanisms of phloretin and phlorizin

Yushi Wei,Jianmei Wu,Xi Peng,Xing Hu,Deming Gong,Guowen Zhang

The anti-glycation potential and mechanism of phloretin and phlorizin were investigated in the study. In the methylglyoxal (MGO)-human serum albumin (HSA) glycosylation system, the inhibition against fluorescent advanced glycosylation end products (AGEs) was more than 60% at 960 μM phloretin and phlorizin. They decreased carbonylation and oxidative damage of protein, protected thiol groups and secondary structure of protein and inhibited protein aggregates. Treated with 1.37 mM phloretin or phlorizin, O 2 − · scavenging was more than 80%, and 1 mM phloretin or phlorizin chelated 60.08% or 28.11% of Fe 2+ , respectively. Analysis of HPLC and LC-QqQ-MS shown phloretin captured MGO by forming adducts with MGO, with capture rates of 92.67% within 24 h. The capture rate of phlorizin to MGO was 56.40%. The anti-glycosylation mechanisms of them could include the structural protection of HSA, capture of MGO, O 2 − · and ·OH scavenging and chelation of Fe 2+ . These findings may provide a theoretical basis for the application of phloretin and phlorizin as novel anti-glycosylation agents.

研究领域: 生物化学 · 药理学
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FOOD CHEMISTRY · 2021 · IF 7.514

Food matrixes play a key role in the distribution of contaminants of lipid origin: A case study of malondialdehyde formation in vegetable oils during deep-frying

Lukai Ma,Qiuxuan He,Yuanxin Qiu,Huifan Liu,Jihong Wu,Guoqin Liu,Charles Brennan,Margaret Anne Brennan,Lixue Zhu

Vegetable oils are increasingly replacing animal fats in diets, but malondialdehyde (MDA), a peroxidation product of these oils, has been regarded as toxic; this necessitated investigation of MDA formation during consumption. This study investigated MDA formation in four vegetable oils during frying French fries (FF) and fried chicken breast meat (FCBM) at 180 °C for 7 h. Results showed that MDA contents were lower in oils used for frying foods than in control oils, mainly because MDA was incorporated into the foods. MDA content was lower in FF, but higher in FCBM, due to the different food components. Model oil and food system analyses yielded similar results. MDA bound the hydrophobic helical structure in starch-based FF, but was exhibited greater reactivity with nucleophilic groups in protein-based FCBM, resulting in stronger interaction with FCBM than with FF. Our results indicated the existence of distinct mechanisms underlying MDA migration in different food matrixes.

研究领域: 食品科学 · 毒理学 · 营养学
✓ 已验证 产品关联 DOI PubMed 高影响因子
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JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY · 2022 · IF 5.895

Controlled Formation of Pyrazines: Inhibition by Ellagic Acid Interaction with N-(1-Deoxy-d-xylulos-1-yl)-glycine and Promotion through Ellagic Acid Oxidation

Ziyan Wang,Heping Cui,Mengyu Ma,Khizar Hayat,Xiaoming Zhang,Chi-Tang Ho

The effect of ellagic acid on the formation of pyrazine, methylpyrazine, 2,3-methylpyrazine, 2,6-methylpyrazine, 2,5-methylpyrazine, and trimethylpyrazine in the xylose–glycine Maillard reaction model was researched. Ellagic acid could either inhibit or promote pyrazine formation, depending on its addition time point and the pH of the system. The addition of ellagic acid during the accumulation period of an Amadori compound inhibited pyrazine formation by capturing the Amadori compound in the xylose–glycine Maillard system and decreasing the pyrazine precursors. The inhibitory effect of ellagic acid on pyrazine formation got more obvious with an increase in the pH of the system. However, when ellagic acid was added at the beginning of the xylose and glycine Maillard system and when the oxidizing substances such as glyoxal and methylglyoxal were significantly formed in the Maillard system, its oxidation could promote the formation of pyrazines.

研究领域: 食品化学 · 有机化学 · 美拉德反应
✓ 已验证 产品关联 DOI PubMed 高影响因子
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Water Cycle · 2023 · IF 0

Removal of tetracycline from water using ethylenediamine-modified magnetic chitosan

Yuankun Liu,Xinxia Zhang,Liyuan Zhao

In this work, the magnetic chitosan nanoparticles were prepared by in-situ co-precipitation method and then modified by glutaraldehyde and ethylenediamine. The effect dose of crosslinking agents for adsorbent preparation on tetracycline (TC) adsorption was investigated. The experiment results showed that the modified chitosan (EMMCS-G) had the best adsorption performance, which was more than twice that of raw magnetic chitosan. EMMCS-G was characterized by SEM, TEM, VSM, FTIR, XRD and XPS. The effects of experimental parameters such as time, temperature, pH, adsorbent dosage and Cu 2+ on TC adsorption by EMMCS-G were discussed. The result indicated that the optimal pH was 6.5. Under the conditions of an initial TC concentration of 50 ​mg/L and an EMMCS-G dosage of 50 ​mg, the removal rate reached an impressive 94%. The isotherm and kinetic studies of adsorption process illustrated that adsorption of TC onto EMMCS corresponded to Freundlich isotherm and pseudo-second-order kinetic models. The maximum adsorption capacity was 84 ​mg/g. Thermodynamic analysis revealed that adsorption process was both endothermic and spontaneous. The regeneration experiment suggested that the adsorbent possessed excellent reusability for further use. Moreover, the adsorption mechanisms of TC onto EMMCS-G mainly involved pore filling, π-π interactions, hydrogen bonding and electrostatic attraction.

研究领域: 环境科学 · 材料科学 · 化学工程
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Catalysts · 2020 ·Vol. 10 ·期 11 ·1266 · IF 3.52

Preparation of Immobilized Lipase on Silica Clay as a Potential Biocatalyst on Synthesis of Biodiesel

Ting Zou,You-dan Duan,Qiao-e Wang,Hai-ming Cheng

Biodiesel offers an important alternative to fossil fuel. In this work,Eversa Transform2.0 lipase was immobilized onto 3-aminopropyltriethoxysilane (APTES) modified silica clay (SC) by glutaraldehyde. The characteristics of the functionalized supports and the immobilized lipase were investigated by FTIR, TEM, BET, and XRD. The results show that the optimal conditions of lipase immobilization are as follows: 2% glutaraldehyde concentration, 15 mg/mL lipase concentration and incubating at 25 °C for 60 min. The immobilized lipase showed a high tolerance to temperature and pH variation in comparison to the free lipase. The immobilized lipase on SC was applied as a biocatalyst for the synthesis of biodiesel from methanol and canola oil. A biodiesel yield of 86% was obtained at a temperature of 45 °C via a three-step methanol addition. A conversion yield of 67% was maintained after reusing the immobilized lipase for five cycles. This work provides a strategy for the preparation of an efficient biocatalyst for the synthesis of biodiesel.Keywords:lipase;silica clay;biodiesel;immobilization;APTES;glutaraldehyde

CAS / MDL: 919-30-2 110-54-3
研究领域: 生物化学 · 能源科学
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SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY · 2019 · IF 2.931

Optical properties investigation of the reactions between methylglyoxal and glycine/ammonium sulfate

Yan Gao,Yunhong Zhang

In recent years, “brown carbon” (BrC), as an important contributor to light absorption and climate forcing as aerosols, has been one of the forefronts in the field of atmospheric research. Aqueous BrC aerosols can be formed through aqueous reactions of methylglyoxal (MG) with nitrogen compounds, such as glycine (Gly) and ammonium sulfate (AS). When exposed to nitrogen compounds for several days, aqueous carbonyl compound MG became absorbent and fluorescent in the ultraviolet and near visible regions, according to UV/Vis and fluorescence spectroscopies. Experiment results showed that optical absorption of two aqueous BrC solutions in the spectral range of 250–480 nm significantly increased with increasing reaction time. After the reactions of MG with Gly and AS, the product absorbance followed the order of MG-Gly>MG-AS. For H 2 O 2 oxidation photolysis, the atmospheric aqueous BrC showed the dynamic nature. Reaction kinetic, effective quantum yields and size distribution studies were conducted in the paper. Fluorescence lifetime values of the two BrC solutions were calculated. LC/MS analysis results clearly indicated that complicated organic compounds were formed in the reactions of MG with Gly and AS.

CAS / MDL: 7439-95-4
研究领域: 大气科学 · 环境化学
✓ 已验证 产品关联 DOI PubMed 高影响因子
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LWT-FOOD SCIENCE AND TECHNOLOGY · 2022 · IF 6.056

Mechanical, microstructural, and rheological characterization of gelatin-dialdehyde starch hydrogels constructed by dual dynamic crosslinking

Tianqi Cui,Yuxue Sun,Yue Wu,Jiarong Wang,Yangyue Ding,Jianjun Cheng,Mingruo Guo

Novel gelatin/dialdehyde starch (GDS) hydrogels based on gelatin were prepared using dialdehyde starch as a macromolecular crosslinking agent. Fourier transform infrared spectroscopy , Raman spectroscopy , and X-ray diffraction showed that the dynamic hydrogel network was formed by covalent imine bonds and hydrogen bonds between dialdehyde starch and gelatin. The synergistic physical and chemical cross-linking endowed the hydrogels with excellent mechanical properties (maximum compressive stress was 0.55 MPa), fatigue resistance (they maintained their shape after ten compression cycles), toughness (54.6 kN/m 2 ), and self-recoverability of the polymeric network. In the rheological tests, all the storage modulus were higher than loss modulus, indicating that they are elastic gels and not viscous sols. The polymer network of GDS hydrogels could recover rapidly when subjected to oscillating shear strain. In addition, with increasing dialdehyde starch concentration, the hydrogels had higher swelling stability and a denser microstructure. Given these excellent properties, the hydrogels have potential application prospects as cell culture scaffolds and carriers of bioactive substance.

CAS / MDL: 9000-70-8
研究领域: 材料科学 · 生物医学工程
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