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RSC Advances · 2018 ·Vol. 8 ·期 63 ·35870-35877 · IF 2.936

The digestibility of hydrothermally-treated bovine serum albumin glycated by glyoxal

Guoying Su,Lin Li,Di Zhao,Bing Li,Xia Zhang

The digestion of dietary advanced glycation end products (AGEs) largely determines their absorption in humans. To help elucidate the health effects of dietary AGEs, changes in the digestive behavior of bovine serum albumin (BSA, dietary protein) caused by glycation derived from glyoxal (GO, an important precursor of AGEs) in a simulated food heating system have been investigated. The hydrothermal aggregation of BSA was suppressed by GO derived glycation, generating glycated aggregates of loose and branched structures, according to dynamic light scattering (DLS), circular dichroism (CD) spectroscopy, free sulfhydryl group, transmission electron microscopy (TEM) and small angle X-ray scattering (SAXS) results. Analysis of protein digests showed that glycation reduced the gastric and gastrointestinal digestibility of BSA and the bioavailability of all seven detected amino acids. A comparative analysis of the distribution of CML and lysine in glycated BSA digests with different molecular weights showed that carboxymethylation directly blocked the action of proteases on Lys residues.

CAS / MDL: 107-22-2
研究领域: 食品科学 · 营养学 · 生物化学
✓ 已验证 产品关联 DOI PubMed 高影响因子
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JOURNAL OF THE TEXTILE INSTITUTE · 2021 · IF 1.88

Anti-wrinkle finishing of Tencel fabric with glyoxal using response surface methodology

Guizhen Ke,Chunliang Chen,Lixiang Yu,Huixia Zhang

In this study, formaldehyde-free anti-wrinkle finishing agent glyoxal was applied on Tencel fabrics. Box Behnken experimental design in conjunction with response surface analysis and regression methods were used to study the effects of process parameters on their wrinkle resistant angle (WRA) as well as tensile strength. It was found that WRA increased with the increase of glyoxal and catalyst MgCl2 concentration and curing temperature, along with the increase of breaking strength loss. Variance analysis showed glyoxal concentration and curing temperature played significant role on the recovery angle and tensile strength of the treated fabrics. The established regression model was reliable and can predict the response value accurately. The Tencel fabric obtained good WRA and tensile strength retention when treated with optimum finishing recipe: glyoxal 49.35 g/L, MgCl2 18.64g/L and curing temperature 136.38 °C. FTIR confirmed the crosslinking reaction between Tencel fibre and glyoxal. SEM observation revealed the treatment produced no damage to the Tencel fibre. The treated Tencel fabrics kept high whiteness retention and glyoxal finishing resulted in no yellowing of Tencel fabrics.

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CHINESE JOURNAL OF CHEMICAL ENGINEERING · 2026 · IF 3.5

Development of a high-performance glyoxal–tannin–epoxy wood adhesive modified with triethylenetetramine

Bao Yang,Zhi Li,Antonio Pizzi,Xingran Wang,Yun Lu,Guanben Du,Xianghong Li,Shuduan Deng

➢ Construction of a robust 3D cross-linked network within TGT-TETA. ➢ Optimal R=8: 2: 1: 1.5 yields max strength: 1.75/1.66/1.12 MPa (dry/hot/boiled). ➢ Inherent antifungal properties are integrated into the TGT-TETA adhesive system. ➢ Significant enhancement in flame retardancy is achieved through the cross-linked network. Due to challenges such as fossil resource scarcity and tightening environmental regulations, the wood industry requires the development of formaldehyde-free adhesives based on renewable resources. This study reports the development of a formaldehyde-free wood adhesive based on biomass-derived tannin, glyoxal, triethylenetetramine (TETA), and glycerol triglycidyl ether (GTE). By introducing GTE as an epoxy-functionalized modifier to the TETA-modified system, the TG resin system (tannin–glyoxal prepolymer) achieves a highly crosslinked three-dimensional network through a synergistic mechanism involving amine–aldehyde condensation and the ring-opening reaction of epoxy groups. Optimization studies revealed that a mass ratio of TETA to tannin of 1:1.5, combined with a precise dosage of GTE, facilitates the formation of a stable C–N and C–O–C covalent network, which significantly improves both mechanical strength and thermal stability. Plywood samples bonded with this adhesive demonstrated superior performance, achieving shear strengths of 1.75 MPa (dry), 1.66 MPa (hot water), and 1.12 MPa (boiling water). These values comfortably exceed the Chinese National Standard (GB/T 17657) requirements for Type II panels (≥ 0.7 MPa), outperforming most previously reported tannin-based adhesives. This work provides a reliable, high-performance technical pathway for the industrial manufacturing of formaldehyde-free wood-based panels. Download: Download high-res image (288KB) Download: Download full-size image

CAS / MDL: 13236-02-7
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Journal of Environmental Sciences · 2025 · IF 6.3

pH-dependent reaction kinetics between glyoxal and ammonium sulfate in simulated cloud droplets

Kun Liu,Tao Wang,Guohua Zhang,Wei Sun,Ye Yang,Mingjin Tang,Xinming Wang,Xinhui Bi

Aqueous-phase reactions between carbonyls and reduced nitrogen compounds play a considerable role in the formation of secondary organic aerosols and brown carbon in the atmosphere. However, the reported reaction rate constants for these reactions have largely been limited to bulk aqueous-phase simulations, which may not accurately represent the real state of atmospheric cloud droplets. We employed an integration of optical tweezers and Raman spectroscopy to manipulate and analyze simulated cloud droplets (size range 8000-10000 nm), comprising a mixture of glyoxal and ammonium sulfate. This approach enabled us to delve into the intricate realm of their reaction kinetics at individual droplet level mimicking cloud droplets. Raman spectroscopy provided high temporal resolution (20 s) measurements of the changes in the amount of nitrogen-containing organics (or NOCs as represented by the C-N bond) within the droplets. The results indicate that the reaction follows first-order kinetics throughout the monitoring over 80-400 minutes. The average reaction rate constant for the formation of NOCs within the single droplet was determined to be (6.77 ± 0.98) × 10 -5 s -1 , up to three orders of magnitude higher than those through the bulk aqueous-phase simulations, especially at lower pH levels. Additionally, the reaction rate constant in single droplet increases with increasing pH, consistent with the trend previously reported for the aqueous-phase simulations. The results highlight the difference of the reaction rate constant between bulk aqueous phase and droplets, which would improve our understanding on the formation and impacts of secondary organic aerosols and brown carbon in atmospheric aqueous phase.

CAS / MDL: 56-40-6
研究领域: 大气科学 · 化学动力学
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Food Bioscience · 2026 · IF 6.2

Systematic evaluation of the immunological, neurological, gastrointestinal, and hepatic toxicity of glyoxal in food

Qiaosi Wei,Xiangxin Wang,Dongying Cui,Jufang Li,Qinggang Xie,Yajun Xu

Glyoxal dietary exposure caused multi-organ toxicity in zebrafish larvae. • MNLC (2.37 μL/mL) and LC10 (5.60 μL/mL) of glyoxal were defined in zebrafish. • Glyoxal at LC10 impaired innate and adaptive immune cell populations. • Glyoxal triggered CNS apoptosis, liver enlargement, and hepatic lesions. Glyoxal is a reactive dicarbonyl compound that is widely detected in carbohydrate- and lipid-rich foods; however, its systemic toxicological effects remain incompletely characterized. Therefore, this study employed wild-type and transgenic zebrafish models to evaluate the systemic toxicity of glyoxal, determining its maximum non-lethal concentration (MNLC) and 10% lethal concentration (LC 10 ). The immunological, neurological, gastrointestinal, and hepatic toxicities of glyoxal at different concentrations were systematically evaluated. Acute toxicity analysis showed that the MNLC of glyoxal was 40.84 mM, and the LC10 was 96.49 mM. Glyoxal produced endpoint-specific toxic effects rather than a uniform continuous dose-response pattern. At the LC 10 concentration, glyoxal significantly reduced neutrophil abundance, T-cell-associated fluorescence, and macrophage-associated fluorescence; decreased gastrointestinal area; increased liver area and residual yolk-sac area; and induced marked hepatic pathological alterations. At the MNLC concentration, glyoxal significantly reduced macrophage-associated fluorescence and increased residual yolk-sac area. Increased residual yolk-sac area was also observed at 1/3 MNLC. In the nervous system, increased central nervous system apoptosis was detected at selected concentrations, whereas no significant changes were observed in motor-neuron development or locomotor distance. Glyoxal also had no significant effect on gastrointestinal neutrophil density or mean liver brightness. Collectively, these findings indicate that the toxicity of glyoxal is characterized by organ- and endpoint-specific threshold-like responses, with most overt toxic effects occurring at or near the LC 10 concentration. This study provides experimental evidence for the hazard characterization of glyoxal and supports further investigation of its relevance to food-safety risk assessment. Download: Download high-res image (245KB) Download: Download full-size image

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Journal of Physical Chemistry C · 2023 · IF 3.7

The Role of Glyoxal as an Intermediate in the Electrochemical CO2 Reduction Reaction on Copper

Ernest Pahuyo Delmo,Yian Wang,Shangqian Zhu,Tiehuai Li,Yinuo Wang,Juhee Jang,Qinglan Zhao,Alexander Perez Roxas,Gabriel Sikukuu Nambafu,Zhengtang Luo,Lu-Tao Weng,Minhua Shao

The C2 product formation mechanism in the electrochemical reduction reaction of CO2 (CO2RR) is still poorly understood. This work aims to analyze the copper-catalyzed electroreduction of aqueous glyoxal to understand its role as a potential reaction intermediate during CO2RR. Multiple reaction pathways are observed during glyoxal reduction, including its electroreduction to ethanol and ethylene glycol, disproportionation to glycolate and formate, and further coupling toward the formation of C4 compounds and graphitic carbon. A significantly high ethylene glycol to ethanol ratio indicates that glyoxal may not be the main intermediate toward ethanol production in CO2RR on Cu, contradicting previous hypotheses. Density functional theory calculations show that the hydration of aldehyde functional groups can shift the ethylene glycol vs ethanol selectivity, in which the former is preferred when the carbonyl groups remain unhydrated. A CO2-to-glycolate pathway is also possible as a consequence of the base-catalyzed internal Cannizzaro disproportionation of glyoxal. Finally, C–C coupling during glyoxal reduction may open up a CO2RR pathway toward C4 products such as tetroses and 1,4-butanediol that have not been previously observed in electrochemical CO2RR. The formation of graphitic carbon also suggests that the carbon deposits usually observed during CO2RR may originate from glyoxal-derived C–C coupling. Our findings offer valuable insights onto the glyoxal pathway of CO2RR and the various multicarbon products that result from the further conversion of glyoxal.

CAS / MDL: 79-14-1
研究领域: 化学 · 材料科学 · 环境科学
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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
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International Journal of Green Energy · 2026 · IF 3.1

Highly soluble glyoxal-modified guanine as a green corrosion inhibitor for Q235 carbon steel in seawater environments

Wei Liu,Caihang Liang,Ronghui Qi

Q235 carbon steel is widely used in seawater cooling systems but suffers severe corrosion in high-salinity environments. Conventional inhibitors are limited by poor water solubility and environmental risks. Here, we synthesized glyoxal-modified guanine (GGO) by introducing hydrophilic – OH groups and coordination-active (C = N/C – N) sites, increasing aqueous solubility from < 1 mg/L (guanine) to 3.289 g/L. Electrochemical and weight loss tests showed that GGO achieved a corrosion inhibition efficiency of 96.15% at 200 ppm in 3.5 wt.% NaCl, greatly surpassing unmodified guanine. SEM, contact angle, and 3D profilometry revealed that GGO formed a compact, hydrophobic protective film, significantly reducing corrosion pits and surface roughness. Adsorption isotherms and thermodynamic analysis indicated that GGO adsorption involves both chemisorption and physisorption, with a more negative Gibbs free energy than guanine. Quantum chemical calculations and molecular dynamics simulations demonstrated that polar functional groups promote strong adsorption and coordination with the steel surface, blocking chloride attack and stabilizing the inhibitor layer. XPS confirmed Fe – N coordination bonds and organic species in the protective film. This study provides a high-efficiency, eco-friendly corrosion inhibition strategy for Q235 carbon steel in saline environments and guides the rational design of green inhibitors for industrial applications.

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JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY · 2019 · IF 3.571

Degradation of Peptide-Bound Maillard Reaction Products in Gastrointestinal Digests of Glyoxal-Glycated Casein by Human Colonic Microbiota

Dan Xu,Lin Li,Xia Zhang,Hong Yao,Mingquan Yang,Zuoqi Gai,Bing Li,Di Zhao

A large portion of Maillard reaction products (MRPs) cannot be absorbed in the upper gut and therefore may be further decomposed and utilized by colonic microbiota (CM). This work reported the stability of UV-absorbent MRPs, fluorescent MRPs and peptide-bound N(ε)-(carboxymethyl)-lysine (CML) in high molecular weight (HMW, >10 kDa), medium molecular weight (MMW, 1–10 kDa), and low molecular weight (LMW, <1 kDa) gastrointestinal digests of glyoxal-glycated casein in the presence of CM. Fluorescent MRPs showed high stability, whereas UV-absorbent MRPs may be partially decomposed. A higher depletion rate of CML was found in the LMW fraction (38.7%) than in the MMW (21.7%) and HMW (9.6%) fractions. The 16S rRNA sequencing results revealed both beneficial and detrimental changes in CM composition induced by the glycated fractions. Generation of short-chain and branched-chain fatty acids in fermentation solutions with glycated fractions was significantly suppressed compared with that in fermentation solution with unglycated digests. This work revealed the possible interplay between peptide-bound MRPs and CM.

研究领域: 食品科学 · 微生物学 · 营养学
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Journal of Materials Research and Technology-JMR&T · 2020 · IF 5.289

Lightweight, hydrophobic and recyclable carbon foam derived from lignin–resorcinol–glyoxal resin for oil and solvent spill capture

Gui-Shi Rao,Hafezeh Nabipour,Ping Zhang,Xin Wang,Weiyi Xing,Lei Song,Yuan Hu

This study reported synthesis of carbon foam from lignin–resorcinol–glyoxal (LRG) resin as carbon source and polyurethane (PU) foam as sacrificial template for effective removal of oils and organic solvents from water. The carbon foam with large surface area and high porosity was fabricated by carbonization of resin impregnated PU foam. The carbon foam can effectively absorb various oil or organic solvents from the aqueous media due to hydrophobic nature. Also, it can be recycled by completely burning the oil or organic solvents without destroying the foam structure. The carbon foam with high absorption capacity and good recyclability properties in the present work suggests promising applications in removal of oils and organic solvent spill from water.

研究领域: 材料科学 · 环境科学
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PLoS Pathogens · 2024 ·Vol. 20 ·期 7 ·e1012431 · IF 5.5

Glyoxal oxidase-mediated detoxification of reactive carbonyl species contributes to virulence, stress tolerance, and development in a pathogenic fungus

Xiaoyu Liu,Nemat O. Keyhani,Hong Liu,Yue Zhang,Yuxian Xia,Yueqing Cao

Reactive carbonyl and oxygen species (RCS/ROS), often generated as metabolic byproducts, particularly under conditions of pathology, can cause direct damage to proteins, lipids, and nucleic acids. Glyoxal oxidases (Gloxs) oxidize aldehydes to carboxylic acids, generating hydrogen peroxide (H 2 O 2 ). Although best characterized for their roles in lignin degradation, Glox in plant fungal pathogens are known to contribute to virulence, however, the mechanism underlying such effects are unclear. Here, we show that Glox in the insect pathogenic fungus, Metarhizium acridum , is highly expressed in mycelia and during formation of infection structures (appressoria), with the enzyme localizing to the cell membrane. MaGlox targeted gene disruption mutants showed RCS and ROS accumulation, resulting in cell toxicity, induction of apoptosis and increased autophagy, inhibiting normal fungal growth and development. The ability of the MaGlox mutant to scavenge RCS was significantly reduced, and the mutant exhibited increased susceptibility to aldehydes, oxidative and cell wall perturbing agents but not toward osmotic stress, with altered cell wall contents. The Δ MaGlox mutant was impaired in its ability to penetrate the host cuticle and evade host immune defense resulting in attenuated pathogenicity. Overexpression of MaGlox promoted fungal growth and conidial germination, increased tolerance to H 2 O 2 , but had little to other phenotypic effects. Transcriptomic analyses revealed downregulation of genes related to cell wall synthesis, conidiation, stress tolerance, and host cuticle penetration in the Δ MaGlox mutant. These findings demonstrate that MaGlox -mediated scavenging of RCS is required for virulence, and contributes to normal fungal growth and development, stress resistance. The ability of organisms to detoxify reactive metabolic byproducts is crucial for normal development, stress resistance, and where applicable, pathogenesis. Here, using the insect pathogenic fungus, Metarhizium acridum , we show that a glyoxal oxidase acts to detoxify cellular reactive carbonyl species (RCS) as well as leading to decreased reactive oxygen species (ROS) levels by alleviating aldehydes accumulation which can trigger ROS production. Mutants deficient in MaGlox showed increased levels of RCS/ROS leading to increased autophagy and apoptosis, resulting in impaired fungal growth, development, and reduced virulence. These findings link Glox mediated RCS/ROS detoxification to cell degradation/turnover processes and cell death, impacting fungal pathogenicity and development.

CAS / MDL: 62-31-7
研究领域: 微生物学 · 真菌学 · 病理学 · 细胞生物学 · 植物病理学
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BIOORGANIC CHEMISTRY · 2020 · IF 4.831

Mulberry anthocyanins exert anti-AGEs effects by selectively trapping glyoxal and structural-dependently blocking the lysyl residues of β-lactoglobulins

Ibrahim Khalifa,Du Xia,Kunal Dutta,Jinmeng Peng,Yangyang Jia,Chunmei Li

Advanced glycation end-products (AGEs), which instigate many disorders, are mostly mediated by dicarbonyl rearrangements. We studied the corresponding mechanisms of the anti-glycation effects of two anthocyanins purified from mulberry fruits, namely cyanidin 3-glucoside (C3G) and cyanidin 3-rutinoside (C3R), on glycated β-lactoglobulins (β-Lg). Both mulberry anthocyanins (MAs) inhibited the AGEs-formation in a dose-dependent manner, but the effect of C3R was significantly stronger than that of C3G (p < 0.05). MAs inhibited AGEs-formation by selectively trapping dicarbonyls, especially glyoxal. The UPLC-ESI-Q-TOF-MS results characterized that C3R formed mono- and di-glyoxal adducts, where C3G only created di-glyoxal adducts. Additionally, C3R could directly interact with some of the glycation sites of β-Lg. Overall, GO-trapping and β-Lg-MAs covalent/noncovalent binding are disclosed as the key mechanisms of the anti-AGEs activity of MAs on β-Lg, which could be valorised as effectual AGEs inhibitors in proteins-rich matrices.

研究领域: 食品科学 · 生物化学
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