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1
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Chen L, Yu Z, Dong S, Huang Y, Xiang X, He Y, Li S, Ye L. Metabolomics unravels the formation pathway of advanced glycation end products in preserved egg yolk mediated by OH - during pickling. Food Chem 2025; 483:144217. [PMID: 40245624 DOI: 10.1016/j.foodchem.2025.144217] [Citation(s) in RCA: 0] [Impact Index Per Article: 0] [Reference Citation Analysis] [Abstract] [Key Words] [MESH Headings] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Received: 11/19/2024] [Revised: 04/02/2025] [Accepted: 04/04/2025] [Indexed: 04/19/2025]
Abstract
Metabolomics was first applied to explore the formation pathway and regulatory factors for advanced glycation end products (AGEs) in preserved egg yolk (PEY) during pickling. Most reactions that contributed to formation of AGEs, including oxidation and/or degradation of matrix/precursors and Maillard reaction, occurred primarily in PEY in early stage, and lipid oxidation occurred prior to protein oxidation. Additionally, the formation of Nε-carboxymethyl-lysine (CML) in PEY was mainly attributed to glyoxal derived from D-glucuronic acid in early stage based on the correlation between metabolites and AGEs. Reactive oxygen radicals from oxidized lipids also promoted the enrichment of CML and Nε-carboxymethyl-lysine (CEL). Moreover, during later stage, the accumulation of CEL was enhanced through methylglyoxal from Schiff bases, and acidic compounds could inhibit AGEs via hindering Maillard reaction. This manuscript pioneered the application of metabolomics to reveal the formation pathway of AGEs, and will provide new perspective on AGEs formation in foods.
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Affiliation(s)
- Le Chen
- School of Food Science and Bioengineering, Changsha University of Science and Technology, Changsha, Hunan 410114, China
| | - Zhuosi Yu
- School of Food Science and Bioengineering, Changsha University of Science and Technology, Changsha, Hunan 410114, China
| | - Shiqin Dong
- School of Food Science and Bioengineering, Changsha University of Science and Technology, Changsha, Hunan 410114, China
| | - Yiqun Huang
- School of Food Science and Bioengineering, Changsha University of Science and Technology, Changsha, Hunan 410114, China
| | - Xiaole Xiang
- School of Food Science and Bioengineering, Changsha University of Science and Technology, Changsha, Hunan 410114, China.
| | - Yu He
- School of Public Health, The Key Laboratory of Environmental Pollution Monitoring and Disease Control, Ministry of Education, Guizhou Medical University, Guiyang, 550025, China
| | - Shugang Li
- Engineering Research Center of Bio-process, Ministry of Education/Key Laboratory for Agricultural Products Processing of Anhui Province/School of Food and Biological Engineering, Hefei University of Technology, Hefei, 230601, China.
| | - Lin Ye
- College of Food Science and Engineering, Tarim University, Alar, Xinjiang 843300, China
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2
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Secco F, Le Roux E, Bosc V, Rega B. Monitoring furanic and dicarbonyl compounds in pea-based and wheat-based sponge cakes during in vitro digestion. Food Res Int 2025; 208:116099. [PMID: 40263881 DOI: 10.1016/j.foodres.2025.116099] [Citation(s) in RCA: 0] [Impact Index Per Article: 0] [Reference Citation Analysis] [Abstract] [Key Words] [MESH Headings] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Received: 10/29/2024] [Revised: 02/04/2025] [Accepted: 02/22/2025] [Indexed: 04/24/2025]
Abstract
The increasing tendency to use animal-free and gluten-free proteins leads to replacing traditional with legume-based ingredients. Of these, refined pea (Pisum sativum L.) is gaining momentum due to its availability, nutritional value and low allergenicity. However, little is known of the propensity of pea ingredients to generate process-induced compounds in high-temperature processed foods, and the reactivity of contaminant during digestion. This study explored the levels and behavior of selected newly formed compounds (NFCs) (furfural, 5-(hydroxymethyl)furfural (HMF), 3-deoxyglucosone (3-DG), 1-deoxyglucosone (1-DG), glyoxal (GO), methylglyoxal (MGO), dimethylglyoxal (DMGO), glucosone (GCO)) in a pea-based sponge cake baked at 200 °C and subjected to in vitro digestion, by comparison with a reference wheat-based cake. The pea formulation generated the highest levels of furanic and dicarbonyl compounds, with 3-DG and HMF being the most abundant (162.44 ± 2.79 and 270.61 ± 14.91 μg/g dry cake, respectively), compared to the wheat-based formulation (131.43 ± 4.34 and 166.83 ± 0.88 μg/g dry cake, respectively). The differences in NFC levels between pea- and wheat-based cakes were maintained during in vitro digestion. Generally, furanic compounds decreased, glyoxales increased and deoxyglucosones were more stable during digestion. Surprisingly, even after any decrease, NFC levels remained high at the end of digestion in both pea- and wheat-based products (up to 215.18 ± 0.42, 188.96 ± 3.02, and 15.76 ± 0.26 μg/g dry cake for HMF, 3-DG, and MGO, respectively). These amounts resulted from the balance between formation and consumption reactions, influenced by gastric and intestinal environments and cake composition. This study has therefore highlighted key safety aspects by considering the behavior during digestion of process-induced compounds in complex, legume-based food matrices.
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Affiliation(s)
- Federica Secco
- Univ. Paris-Saclay, INRAE, AgroParisTech, UMR SayFood, 91120 Palaiseau, France.
| | - Even Le Roux
- Univ. Paris-Saclay, INRAE, AgroParisTech, UMR SayFood, 91120 Palaiseau, France.
| | - Véronique Bosc
- Univ. Paris-Saclay, INRAE, AgroParisTech, UMR SayFood, 91120 Palaiseau, France.
| | - Barbara Rega
- Univ. Paris-Saclay, INRAE, AgroParisTech, UMR SayFood, 91120 Palaiseau, France.
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3
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Peng X, Hu H, Liu Y, Li J, Huang Y, Wang H, Wang Z, Wang Y. In Vitro Digestion Patterns of Advanced Glycation End Products and α-Dicarbonyls in Biscuits and the Modulatory Effects of Ferulic Acid and Epicatechin. Foods 2025; 14:1429. [PMID: 40282829 PMCID: PMC12027215 DOI: 10.3390/foods14081429] [Citation(s) in RCA: 0] [Impact Index Per Article: 0] [Reference Citation Analysis] [Abstract] [Key Words] [Grants] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Received: 02/28/2025] [Revised: 03/26/2025] [Accepted: 04/03/2025] [Indexed: 04/29/2025] Open
Abstract
The dietary intake amount of processing contaminants does not reflect their actual exposure risk due to interactions with the food matrix during gastrointestinal processes, which significantly modulate their bioaccessibility. This study systematically investigated the in vitro digestion patterns of advanced glycation end products (AGEs) and α-dicarbonyl compounds (α-DCs) in biscuits and the modulatory effects of ferulic acid and epicatechin. The results demonstrated that more than 80% of AGEs and α-DCs were present in the bioaccessible fraction of the samples after intestinal digestion. Ferulic acid (FA, 0.05%, w/w) significantly increased the AGEs content in the bioaccessible fraction after intestinal digestion compared to control samples. Conversely, FA at 0.2% and 0.5%, as well as epicatechin (EC) at 0.05%, significantly reduced the glyoxal and 3-deoxyglucosone levels during oral digestion and significantly increased these contaminants contents after gastric digestion. The higher the concentration of EC, the lower the level of methylglyoxal during oral and gastric digestion. In addition, we identified the adducts of FA with lysine and the adducts of EC with Nε-Carboxymethyl-lysine using LC-QTOF-MS, demonstrating the reactivity between polyphenols, amino acids and contaminants. This study provides guidance and suggestions for mitigating dietary exposure to AGEs and α-DCs.
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Affiliation(s)
| | | | | | | | | | | | | | - Yuting Wang
- State Key Laboratory of Food Science and Resources, China-Canada Joint Lab of Food Science and Technology (Nanchang), Nanchang University, 235 Nanjing East Road, Nanchang 330047, China; (X.P.); (H.H.); (Y.L.); (J.L.); (Y.H.); (H.W.); (Z.W.)
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4
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Zhang F, Yu X, Tian Y, Zeng J, Zhuang P, Jia W, Zhang Y. Joint control of multiple food processing contaminants in Maillard reaction: A comprehensive review of health risks and prevention. Compr Rev Food Sci Food Saf 2025; 24:e70138. [PMID: 39929674 DOI: 10.1111/1541-4337.70138] [Citation(s) in RCA: 0] [Impact Index Per Article: 0] [Reference Citation Analysis] [Abstract] [Key Words] [MESH Headings] [Grants] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Received: 08/17/2024] [Revised: 01/21/2025] [Accepted: 01/25/2025] [Indexed: 05/08/2025]
Abstract
There is an urgent need to address food safety concerns associated with multiple Maillard reaction‒derived chemical contaminants, such as acrylamide, heterocyclic aromatic amines, advanced glycation end products, and 5-hydroxymethylfurfural, which are present in processed foods. Current studies have focused on single contaminant generated by the Maillard reaction; however, there is a dearth of information regarding the interactions of multiple contaminants and their joint control methods. This review article comprehensively summarizes the state-of-the-art progress in the simultaneous analysis, coformation, joint hazardous control, and risk assessment of multiple food processing contaminants generated by the Maillard reaction. The Maillard reaction is associated with caramelization, lipid oxidation, protein oxidation, and ascorbic acid browning reactions. Mass spectrometry‒based chromatography is currently the preferred method for the simultaneous quantification of multiple contaminants, with metabolomics and indirect detection methodologies providing new insights. Mitigation strategies for multiple contaminants include optimizing pretreatment, introducing exogenous additives, regulating processing parameters, and utilizing emerging technologies. Limited animal studies on the metabolism of various contaminants have yielded diverse results, guided by biomarkers for deep understanding. Integrated risk assessment should be conducted to quantify multihazard health impacts. In future research, a unique framework should be developed for assessing multiple contaminants, characterizing their metabolic profiles, and optimizing control measures for Maillard reaction‒derived contaminants.
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Affiliation(s)
- Fan Zhang
- Zhejiang Key Laboratory of Agri-Food Resources and High-Value Utilization, National Engineering Laboratory of Intelligent Food Technology and Equipment, College of Biosystems Engineering and Food Science, Zhejiang University, Hangzhou, China
| | - Xiaomei Yu
- Zhejiang Key Laboratory of Agri-Food Resources and High-Value Utilization, National Engineering Laboratory of Intelligent Food Technology and Equipment, College of Biosystems Engineering and Food Science, Zhejiang University, Hangzhou, China
| | - Yimei Tian
- Zhejiang Key Laboratory of Agri-Food Resources and High-Value Utilization, National Engineering Laboratory of Intelligent Food Technology and Equipment, College of Biosystems Engineering and Food Science, Zhejiang University, Hangzhou, China
| | - Jia Zeng
- Zhejiang Key Laboratory of Agri-Food Resources and High-Value Utilization, National Engineering Laboratory of Intelligent Food Technology and Equipment, College of Biosystems Engineering and Food Science, Zhejiang University, Hangzhou, China
| | - Pan Zhuang
- Zhejiang Key Laboratory of Agri-Food Resources and High-Value Utilization, National Engineering Laboratory of Intelligent Food Technology and Equipment, College of Biosystems Engineering and Food Science, Zhejiang University, Hangzhou, China
| | - Wei Jia
- Zhejiang Key Laboratory of Agri-Food Resources and High-Value Utilization, National Engineering Laboratory of Intelligent Food Technology and Equipment, College of Biosystems Engineering and Food Science, Zhejiang University, Hangzhou, China
| | - Yu Zhang
- Zhejiang Key Laboratory of Agri-Food Resources and High-Value Utilization, National Engineering Laboratory of Intelligent Food Technology and Equipment, College of Biosystems Engineering and Food Science, Zhejiang University, Hangzhou, China
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Herraiz T, Salgado A, Peña A. Identification, Occurrence, and Mechanism of Formation of 1-Acetyl-β-carbolines Derived from l-Tryptophan and Methylglyoxal. JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY 2025; 73:3044-3055. [PMID: 39846416 DOI: 10.1021/acs.jafc.4c09130] [Citation(s) in RCA: 0] [Impact Index Per Article: 0] [Reference Citation Analysis] [Abstract] [Key Words] [MESH Headings] [Track Full Text] [Subscribe] [Scholar Register] [Indexed: 01/24/2025]
Abstract
β-Carbolines (βCs) are bioactive compounds present in foods and biological systems. This work describes the identification, occurrence, and mechanism of formation of 1-acetyl-β-carbolines (1-acetyl-βCs) that result from the reaction of l-tryptophan with the α-dicarbonyl compound methylglyoxal. Two β-carbolines are characterized as 1-acetyl-β-carboline (AβC) and 1-acetyl-β-carboline-3-carboxylic acid (AβC-COOH). Their formation was favored in acidic conditions and with increasing temperature, but 1-acetyl-βCs also formed in moderate temperatures and in a wide range of pH, including physiological conditions, and in human serum. The formation mechanism relies on tautomerism and cyclization to give 1-(1-hydroxyethyl)-3,4-dihydro-β-carboline-3-carboxylic acid intermediates followed by the oxidation of C1'-OH and aromatization to 1-acetyl-βCs. The formation of 1-acetyl-βCs took place in the reactions of fructose or glucose with tryptophan under heating and depended on the methylglyoxal released during carbohydrate degradation. Formation from carbohydrates increased at neutral or basic pH values as more methylglyoxal was released under those conditions. Thus, 1-acetyl-βCs could be advanced glycation end-products (AGEs). 1-Acetyl-βCs were identified and quantified for the first time in many foods. AβC ranged from undetectable to 250 ng/g with the highest amount detected in honey, bread, cookies, soy sauce, and coffee. On average, AβC-COOH generally appeared in lower concentrations than AβC but it ranged from undetectable to 323 ng/g with the highest levels found in soy sauce, honey, cookies, and fried bread. These results indicate that 1-acetyl-βCs could be relevant βCs in foods and in vivo.
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Affiliation(s)
- Tomás Herraiz
- Spanish National Research Council (CSIC), Instituto de Ciencia y Tecnología de Alimentos y Nutrición (ICTAN), Jose Antonio Nováis 6 28040, Madrid, Spain
| | - Antonio Salgado
- Centro de Espectroscopía de RMN (CERMN), Universidad de Alcalá (UAH), Campus Universitario, Ctra. Madrid-Barcelona km 33.6, Alcalá de Henares 28805, Madrid, Spain
| | - Adriana Peña
- Spanish National Research Council (CSIC), Instituto de Ciencia y Tecnología de Alimentos y Nutrición (ICTAN), Jose Antonio Nováis 6 28040, Madrid, Spain
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Chen N, Xu X, Yang X, Hu X, Chen F, Zhu Y. Polyphenols as reactive carbonyl substances regulators: A comprehensive review of thermal processing hazards mitigation. Food Res Int 2025; 200:115515. [PMID: 39779146 DOI: 10.1016/j.foodres.2024.115515] [Citation(s) in RCA: 0] [Impact Index Per Article: 0] [Reference Citation Analysis] [Abstract] [Key Words] [MESH Headings] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Received: 10/01/2024] [Revised: 12/11/2024] [Accepted: 12/11/2024] [Indexed: 01/11/2025]
Abstract
Reactive carbonyl species (RCS) are a class of compounds with one or more C = O structures with highly reactive electrophilic properties. This comprehensive review delves into the multifaceted role of RCS in thermally processed foods, where they serve as both crucial intermediates in the development of food color and flavor, as well as precursors of potentially harmful compounds. By exploring the carbonyl pool concept, the impact of RCS equilibrium on the formation and reduction of hazardous substances such as acrylamide, hydroxymethylfurfural, advanced glycation end-products, and heterocyclic amines was elucidated. The review particularly emphasizes the regulatory effects of polyphenols on the carbonyl pool, highlighting their potential to reduce the levels of RCS and their associated hazards. Furthermore, the dual role of polyphenols in both mitigating and enhancing to the formation of RCS and their associated hazards was discussed. This review offers valuable insights into strategies for inhibiting RCS and their associated hazards.
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Affiliation(s)
- Nuo Chen
- College of Food Science and Nutritional Engineering, National Engineering Research Centre for Fruits and Vegetables Processing, Key Laboratory of Storage and Processing of Fruits and Vegetables, Ministry of Agriculture, Engineering Research Centre for Fruits and Vegetables Processing, Ministry of Education, China Agricultural University, Beijing 100083, China
| | - Xinrui Xu
- College of Food Science and Nutritional Engineering, National Engineering Research Centre for Fruits and Vegetables Processing, Key Laboratory of Storage and Processing of Fruits and Vegetables, Ministry of Agriculture, Engineering Research Centre for Fruits and Vegetables Processing, Ministry of Education, China Agricultural University, Beijing 100083, China
| | - Xin Yang
- College of Food Science and Nutritional Engineering, National Engineering Research Centre for Fruits and Vegetables Processing, Key Laboratory of Storage and Processing of Fruits and Vegetables, Ministry of Agriculture, Engineering Research Centre for Fruits and Vegetables Processing, Ministry of Education, China Agricultural University, Beijing 100083, China
| | - Xiaosong Hu
- College of Food Science and Nutritional Engineering, National Engineering Research Centre for Fruits and Vegetables Processing, Key Laboratory of Storage and Processing of Fruits and Vegetables, Ministry of Agriculture, Engineering Research Centre for Fruits and Vegetables Processing, Ministry of Education, China Agricultural University, Beijing 100083, China
| | - Fang Chen
- College of Food Science and Nutritional Engineering, National Engineering Research Centre for Fruits and Vegetables Processing, Key Laboratory of Storage and Processing of Fruits and Vegetables, Ministry of Agriculture, Engineering Research Centre for Fruits and Vegetables Processing, Ministry of Education, China Agricultural University, Beijing 100083, China
| | - Yuchen Zhu
- College of Food Science and Nutritional Engineering, National Engineering Research Centre for Fruits and Vegetables Processing, Key Laboratory of Storage and Processing of Fruits and Vegetables, Ministry of Agriculture, Engineering Research Centre for Fruits and Vegetables Processing, Ministry of Education, China Agricultural University, Beijing 100083, China.
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7
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Tang Y, Huang Y, Li M, Zhu W, Zhang W, Luo S, Zhang Y, Ma J, Jiang Y. Balancing Maillard reaction products formation and antioxidant activities for improved sensory quality and health benefit properties of pan baked buns. Food Res Int 2024; 195:114984. [PMID: 39277245 DOI: 10.1016/j.foodres.2024.114984] [Citation(s) in RCA: 1] [Impact Index Per Article: 1.0] [Reference Citation Analysis] [Abstract] [Key Words] [MESH Headings] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Received: 04/05/2024] [Revised: 08/02/2024] [Accepted: 08/21/2024] [Indexed: 09/17/2024]
Abstract
This study investigated the impact of processing temperatures (190 °C, 210 °C, and 230 °C) and durations (7 min, 10 min, and 14 min) on the formation of Maillard reaction products (MRPs) and antioxidant activities in pan baked buns. Key Maillard reaction indicators, including glyoxal (GO), methylglyoxal (MGO), 5-hydroxymethylfurfural (5-HMF), melanoidins, and fluorescent advanced glycation end products (AGEs) were quantified. The results demonstrated significant increases in GO, MGO, 5-HMF contents (p < 0.05), and antioxidant activities (p < 0.05) when the buns were baked at 210 °C for 14 min, 230 °C for 10 min and 14 min. However, the interior MRPs of baked buns were minimally affected by the baking temperature and duration. Prolonged heating temperatures and durations exacerbated MRPs production (43.8 %-1038 %) in the bottom crust. Nonetheless, this process promoted the release of bound phenolic compounds and enhanced the antioxidant activity. Heating induces the thermal degradation of macromolecules in food, such as proteins and polysaccharides, which releases bound phenolic compounds by disrupting their chemical bonds within the food matrix. Appropriate selections of baking parameters can effectively reduce the formation of MRPs while simultaneously improve sensory quality and health benefit of the pan baked buns. Considering the balance between higher antioxidant properties and lower MRPs, the optimal thermal parameters for pan baked buns were 210 °C for 10 min. Furthermore, a normalized analysis revealed a consistent trend for GO, MGO, 5-HMF, fluorescent AGEs, and melanoidins. Moreover, MRPs were positively correlated with total contents of phenolic compounds, ferric-reducing antioxidant power (FRAP), and color, but negatively correlated with moisture contents and reducing sugars. Additionally, the interaction between baking conditions and Maillard reactions probably contributed to enhanced primary flavors in the final product. This study highlights the importance of optimizing baking parameters to achieve desirable MRPs levels, higher antioxidant activity, and optimal sensory attributes in baked buns.
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Affiliation(s)
- Yao Tang
- State Key Laboratory of Food Nutrition and Safety, College of Food Science and Engineering, Tianjin University of Science and Technology, Tianjin 300457, China
| | - Yuan Huang
- State Key Laboratory of Food Nutrition and Safety, College of Food Science and Engineering, Tianjin University of Science and Technology, Tianjin 300457, China
| | - Mengru Li
- State Key Laboratory of Food Nutrition and Safety, College of Food Science and Engineering, Tianjin University of Science and Technology, Tianjin 300457, China
| | - Wen Zhu
- State Key Laboratory of Food Nutrition and Safety, College of Food Science and Engineering, Tianjin University of Science and Technology, Tianjin 300457, China
| | - Wei Zhang
- State Key Laboratory of Food Nutrition and Safety, College of Food Science and Engineering, Tianjin University of Science and Technology, Tianjin 300457, China
| | - Sha Luo
- Food Safety Facility, Tianjin Centers for Disease Control and Prevention, Tianjin 300011, China
| | - Yingying Zhang
- Department of Cardiology, Tianjin Chest Hospital, Tianjin 300222, China
| | - Jie Ma
- Food Safety Facility, Tianjin Centers for Disease Control and Prevention, Tianjin 300011, China.
| | - Yuqian Jiang
- State Key Laboratory of Food Nutrition and Safety, College of Food Science and Engineering, Tianjin University of Science and Technology, Tianjin 300457, China.
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8
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Karloff DB, Stubbs RT, Ibukun OJ, Knutson SD, James SH, Heemstra JM. Glyoxal Caging of Nucleoside Antivirals toward Self-Activating, Extended-Release Prodrugs. J Am Chem Soc 2024; 146:29402-29406. [PMID: 39412404 PMCID: PMC11867213 DOI: 10.1021/jacs.4c08371] [Citation(s) in RCA: 0] [Impact Index Per Article: 0] [Reference Citation Analysis] [Abstract] [MESH Headings] [Grants] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 11/01/2024]
Abstract
Nucleoside antivirals are a leading class of compounds prescribed as a first-line treatment for viral infections. However, inherent limitations such as low solubility and circulation lifetime can necessitate multi-intraday dosing. Here, we deploy the 1,2-dialdehyde glyoxal to generate antiviral nucleoside prodrugs with enhanced pharmacokinetic properties and extended-release activity to combat poor patient adherence. The near-quantitative reaction of glyoxal with acyclovir (ACV) drastically improves ACV solubility and enables subsequent drug release with a half-life of 1.9 h under physiological conditions. Further, glyoxal caging thermoreversibly disrupts ACV activity against HIV-1 reverse transcription in vitro and HSV-1 pathology in cellulo. Finally, the amenability of a panel of nucleoside reverse transcriptase inhibitors to glyoxal caging showcases the potential of this highly versatile method for achieving timed-release activation of a clinically important class of antiviral therapeutics.
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Affiliation(s)
- Diane B. Karloff
- Department of Chemistry, Washington University, St. Louis, MO 63130, United States
- Department of Chemistry, Emory University, Atlanta, GA 30322, United States
| | - R. Trent Stubbs
- Department of Chemistry, Emory University, Atlanta, GA 30322, United States
| | - Olamilekan J. Ibukun
- Department of Chemistry, Washington University, St. Louis, MO 63130, United States
| | - Steve D. Knutson
- Department of Chemistry, Emory University, Atlanta, GA 30322, United States
| | - Scott H. James
- Department of Pediatrics, Division of Infectious Diseases, University of Alabama at Birmingham, Birmingham, AL 35233, United States
| | - Jennifer M. Heemstra
- Department of Chemistry, Washington University, St. Louis, MO 63130, United States
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Artasensi A, Mazzotta S, Sanz I, Lin L, Vistoli G, Fumagalli L, Regazzoni L. Exploring Secondary Amine Carnosine Derivatives: Design, Synthesis, and Properties. Molecules 2024; 29:5083. [PMID: 39519724 PMCID: PMC11547551 DOI: 10.3390/molecules29215083] [Citation(s) in RCA: 0] [Impact Index Per Article: 0] [Reference Citation Analysis] [Abstract] [Key Words] [MESH Headings] [Track Full Text] [Figures] [Journal Information] [Subscribe] [Scholar Register] [Received: 09/29/2024] [Revised: 10/21/2024] [Accepted: 10/22/2024] [Indexed: 11/16/2024] Open
Abstract
Carnosine is a naturally occurring dipeptide that has been advocated by some authors as an interesting scaffold for the development of potential therapeutic agents in view of the positive outcomes of its supplementation in animal models of human diseases. Its mode of action seems to depend on the quenching of toxic electrophiles, such as 4-hydroxynonenal (HNE). However, carnosine's bioavailability in humans is lower than that in other mammals. The main reason for such an unfavorable pharmacokinetic profile is the activity of the enzyme human serum carnosinase (E.C. 3.4.13.20), which rapidly hydrolyzes carnosine upon absorption. Therefore, some studies have focused on the design of carnosinase-resistant derivatives that retain binding activity toward toxic electrophiles. Nevertheless, the structural modification of the N-terminus amino group of carnosine has rarely been considered, possibly because of its key role in the electrophile scavenging mechanism. This was proven, since some carnosine N-terminus modification generated inactive compounds, despite some derivatives retaining oral bioavailability and gaining resistance to carnosinase hydrolysis. Herein, we therefore report a study aimed at exploring whether the amino group of carnosine can be conveniently modified to develop carnosinase-resistant derivatives retaining the dipeptide activity toward toxic electrophiles.
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Affiliation(s)
- Angelica Artasensi
- Department of Pharmaceutical Sciences, Università degli Studi di Milano, Via L. Mangiagalli 25, 20133 Milan, Italy
| | - Sarah Mazzotta
- Department of Pharmaceutical Sciences, Università degli Studi di Milano, Via L. Mangiagalli 25, 20133 Milan, Italy
- Department of Chemistry, Università degli Studi di Milano, Via Golgi 19, 20133 Milan, Italy
| | - Ines Sanz
- Department of Pharmaceutical Sciences, Università degli Studi di Milano, Via L. Mangiagalli 25, 20133 Milan, Italy
| | - Licheng Lin
- Department of Pharmaceutical Sciences, Università degli Studi di Milano, Via L. Mangiagalli 25, 20133 Milan, Italy
| | - Giulio Vistoli
- Department of Pharmaceutical Sciences, Università degli Studi di Milano, Via L. Mangiagalli 25, 20133 Milan, Italy
| | - Laura Fumagalli
- Department of Pharmaceutical Sciences, Università degli Studi di Milano, Via L. Mangiagalli 25, 20133 Milan, Italy
| | - Luca Regazzoni
- Department of Pharmaceutical Sciences, Università degli Studi di Milano, Via L. Mangiagalli 25, 20133 Milan, Italy
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10
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Hanna GS, Findlay VJ, Turner DP, Hamann MT. Quantitative NMR Analysis of Marine Macroalgae for AGE Inhibition by Methylglyoxal Scavenging. JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY 2024; 72:21905-21911. [PMID: 39298668 DOI: 10.1021/acs.jafc.4c04367] [Citation(s) in RCA: 0] [Impact Index Per Article: 0] [Reference Citation Analysis] [Abstract] [Key Words] [MESH Headings] [Grants] [Track Full Text] [Subscribe] [Scholar Register] [Indexed: 09/22/2024]
Abstract
Reactive carbonyl species (RCS) induce a fundamental form of biological stress that has driven the evolution of diverse mechanisms for minimizing its impact on organismal health. The complications that accompany uncontrolled hyperglycemia exemplify the health implications when RCS stress exceeds the body's capacity to prevent the excessive formation of advanced glycation end-products. Presented here is a novel quantitative NMR (qNMR) technique for evaluating scavengers of the prominent sugar-derived carbonyl methylglyoxal (MGO). This tool was employed to screen the chemical diversity of marine macroalgae extracts, with a focus on species that have a history of consumption by the World's healthiest populations and are subject to global scale aquacultural production. Fucus vesiculosus demonstrated the highest capacity for inhibiting glycation and scavenging MGO. Additionally, the Chondrus cripsus, Gracilaria vermiculophyla, and Gracilaria tikvahiae extracts had a high capacity for scavenging MGO, representing the first report of this activity. This new qNMR methodology presented is highly applicable for screening extracts and compounds from diverse sources, and the results highlight the potential of macroalgae extracts to be employed as RCS and AGE targeting therapeutics and food additives.
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Affiliation(s)
- George S Hanna
- Department of Biomedical Sciences and Drug Discovery, Medical University of South Carolina, Charleston, South Carolina 29425, United States
- Department of Public Health, Medical University of South Carolina, Charleston, South Carolina 29425, United States
| | - Victoria J Findlay
- Department of Surgery, Massey Comprehensive Cancer Center, Virginia Commonwealth University, Richmond, Virginia 23298, United States
| | - David P Turner
- Department of Surgery, Massey Comprehensive Cancer Center, Virginia Commonwealth University, Richmond, Virginia 23298, United States
| | - Mark T Hamann
- Department of Biomedical Sciences and Drug Discovery, Medical University of South Carolina, Charleston, South Carolina 29425, United States
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11
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Nyarko K, Greenlief CM. Investigations of Major α-Dicarbonyl Content in U.S. Honey of Different Geographical Origins. Molecules 2024; 29:1588. [PMID: 38611866 PMCID: PMC11013281 DOI: 10.3390/molecules29071588] [Citation(s) in RCA: 0] [Impact Index Per Article: 0] [Reference Citation Analysis] [Abstract] [Key Words] [MESH Headings] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Received: 02/19/2024] [Revised: 03/31/2024] [Accepted: 04/01/2024] [Indexed: 04/14/2024] Open
Abstract
α-Dicarbonyls are significant degradation products resulting from the Maillard reaction during food processing. Their presence in foods can indicate the extent of heat exposure, processing treatments, and storage conditions. Moreover, they may be useful in providing insights into the potential antibacterial and antioxidant activity of U.S. honey. Despite their importance, the occurrence of α-dicarbonyls in honey produced in the United States has not been extensively studied. This study aims to assess the concentrations of α-dicarbonyls in honey samples from different regions across the United States. The identification and quantification of α-dicarbonyls were conducted using reverse-phase liquid chromatography after derivatization with o-phenylenediamine (OPD) and detected using ultraviolet (UV) and mass spectrometry methods. This study investigated the effects of pH, color, and derivatization reagent on the presence of α-dicarbonyls in honey. The quantification method was validated by estimating the linearity, precision, recovery, method limit of detection, and quantification using known standards for GO, MGO, and 3-DG, respectively. Three major OPD-derivatized α-dicarbonyls including methylglyoxal (MGO), glyoxal (GO), and 3-deoxyglucosone (3-DG), were quantified in all the honey samples. 3-Deoxyglucosone (3-DG) was identified as the predominant α-dicarbonyl in all the U.S. honey samples, with concentrations ranging from 10.80 to 50.24 mg/kg. The total α-dicarbonyl content ranged from 16.81 to 55.74 mg/kg, with the highest concentration measured for Southern California honey. Our results showed no significant correlation between the total α-dicarbonyl content and the measured pH solutions. Similarly, we found that lower amounts of the OPD reagent are optimal for efficient derivatization of MGO, GO, and 3-DG in honey. Our results also indicated that darker types of honey may contain higher α-dicarbonyl content compared with lighter ones. The method validation results yielded excellent recovery rates for 3-DG (82.5%), MGO (75.8%), and GO (67.0%). The method demonstrated high linearity with a limit of detection (LOD) and limit of quantitation (LOQ) ranging from 0.0015 to 0.002 mg/kg and 0.005 to 0.008 mg/kg, respectively. Our results provide insights into the occurrence and concentrations of α-dicarbonyl compounds in U.S. honey varieties, offering valuable information on their quality and susceptibility to thermal processing effects.
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Zhang M, Huang C, Ou J, Liu F, Ou S, Zheng J. Glyoxal in Foods: Formation, Metabolism, Health Hazards, and Its Control Strategies. JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY 2024; 72:2434-2450. [PMID: 38284798 DOI: 10.1021/acs.jafc.3c08225] [Citation(s) in RCA: 20] [Impact Index Per Article: 20.0] [Reference Citation Analysis] [Abstract] [Key Words] [MESH Headings] [Track Full Text] [Subscribe] [Scholar Register] [Indexed: 01/30/2024]
Abstract
Glyoxal is a highly reactive aldehyde widely present in common diet and environment and inevitably generated through various metabolic pathways in vivo. Glyoxal is easily produced in diets high in carbohydrates and fats via the Maillard reaction, carbohydrate autoxidation, and lipid peroxidation, etc. This leads to dietary intake being a major source of exogenous exposure. Exposure to glyoxal has been positively associated with a number of metabolic diseases, such as diabetes mellitus, atherosclerosis, and Alzheimer's disease. It has been demonstrated that polyphenols, probiotics, hydrocolloids, and amino acids can reduce the content of glyoxal in foods via different mechanisms, thus reducing the risk of exogenous exposure to glyoxal and alleviating carbonyl stresses in the human body. This review discussed the formation and metabolism of glyoxal, its health hazards, and the strategies to reduce such health hazards. Future investigation of glyoxal from different perspectives is also discussed.
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Affiliation(s)
- Mianzhang Zhang
- Department of Food Science and Engineering, Jinan University, 510632 Guangzhou, Guangdong China
| | - Caihuan Huang
- Department of Food Science and Engineering, Jinan University, 510632 Guangzhou, Guangdong China
| | - Juanying Ou
- Department of Food Science and Engineering, Jinan University, 510632 Guangzhou, Guangdong China
| | - Fu Liu
- Department of Food Science and Engineering, Jinan University, 510632 Guangzhou, Guangdong China
| | - Shiyi Ou
- Department of Food Science and Engineering, Jinan University, 510632 Guangzhou, Guangdong China
- Guangzhou College of Technology and Business, 510580 Guangzhou, Guangdong China
| | - Jie Zheng
- Department of Food Science and Engineering, Jinan University, 510632 Guangzhou, Guangdong China
- Guangdong-Hong Kong Joint Innovation Platform for the Safety of Bakery Products, 510632 Guangzhou , China
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13
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Berdowska I, Matusiewicz M, Fecka I. Methylglyoxal in Cardiometabolic Disorders: Routes Leading to Pathology Counterbalanced by Treatment Strategies. Molecules 2023; 28:7742. [PMID: 38067472 PMCID: PMC10708463 DOI: 10.3390/molecules28237742] [Citation(s) in RCA: 0] [Impact Index Per Article: 0] [Reference Citation Analysis] [Abstract] [Key Words] [MESH Headings] [Track Full Text] [Figures] [Journal Information] [Subscribe] [Scholar Register] [Received: 09/29/2023] [Revised: 11/13/2023] [Accepted: 11/21/2023] [Indexed: 12/18/2023] Open
Abstract
Methylglyoxal (MGO) is the major compound belonging to reactive carbonyl species (RCS) responsible for the generation of advanced glycation end products (AGEs). Its upregulation, followed by deleterious effects at the cellular and systemic levels, is associated with metabolic disturbances (hyperglycemia/hyperinsulinemia/insulin resistance/hyperlipidemia/inflammatory processes/carbonyl stress/oxidative stress/hypoxia). Therefore, it is implicated in a variety of disorders, including metabolic syndrome, diabetes mellitus, and cardiovascular diseases. In this review, an interplay between pathways leading to MGO generation and scavenging is addressed in regard to this system's impairment in pathology. The issues associated with mechanistic MGO involvement in pathological processes, as well as the discussion on its possible causative role in cardiometabolic diseases, are enclosed. Finally, the main strategies aimed at MGO and its AGEs downregulation with respect to cardiometabolic disorders treatment are addressed. Potential glycation inhibitors and MGO scavengers are discussed, as well as the mechanisms of their action.
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Affiliation(s)
- Izabela Berdowska
- Department of Medical Biochemistry, Wroclaw Medical University, 50-368 Wroclaw, Poland;
| | | | - Izabela Fecka
- Department of Pharmacognosy and Herbal Medicines, Wroclaw Medical University, 50-556 Wroclaw, Poland
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Serin Y, Akbulut G, Yaman M. Investigating Bioaccessibility of Advanced Glycation Product Precursors in Gluten-Free Foods Using In Vitro Gastrointestinal System. MEDICINA (KAUNAS, LITHUANIA) 2023; 59:1578. [PMID: 37763697 PMCID: PMC10535651 DOI: 10.3390/medicina59091578] [Citation(s) in RCA: 2] [Impact Index Per Article: 1.0] [Reference Citation Analysis] [Abstract] [Key Words] [MESH Headings] [Track Full Text] [Download PDF] [Figures] [Subscribe] [Scholar Register] [Received: 07/05/2023] [Revised: 08/05/2023] [Accepted: 08/28/2023] [Indexed: 09/29/2023]
Abstract
Background and Objectives: Gluten-free products have been produced as part of medical therapy and have gained popularity among individuals seeking weight loss or healthier dietary options. Assessing the potential risks associated with these products is essential in optimizing their compositions and developing new dietetic approaches. This study aimed to determine the glyoxal (GO) and methylglyoxal (MGO) contents in gluten-free bread, biscuits, and cookies and to examine their bioaccessibility using an in vitro gastrointestinal model. Materials and Methods: A total of 26 gluten-free and 19 gluten-containing (control) products were analyzed for their GO and MGO levels utilizing a high-performance liquid chromatography (HPLC) device. Results: Post-digestion, the GO and MGO values increased significantly across all food groups compared with pre-digestion values (p < 0.05), and the bioaccessibility exceeded 100%. Specifically, gluten-free bread exhibited higher post-digestion GO and MGO values than the control group (p < 0.05). Conversely, gluten-containing biscuits and cookies had higher post-digestion GO and MGO values compared to gluten-free products (p < 0.05). Conclusions: The detection of precursors to advanced glycation end products (AGEs) in gluten-free products has drawn attention to the potential health risks associated with their consumption. Therefore, reevaluation of the formulations and technologies used in these products and the introduction of new strategies are crucial in mitigating AGE content.
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Affiliation(s)
- Yeliz Serin
- Department of Nutrition and Dietetics, Faculty of Health Sciences, Cukurova University, 01380 Adana, Turkey
| | - Gamze Akbulut
- Department of Nutrition and Dietetics, Faculty of Health Sciences, Gazi University, 06490 Ankara, Turkey;
- Department of Nutrition and Dietetics, Faculty of Health Sciences, Istanbul Kent University, 34433 Istanbul, Turkey
| | - Mustafa Yaman
- Department of Nutrition and Dietetics, Faculty of Health Sciences, Istanbul Sabahattin Zaim University, 34303 Istanbul, Turkey
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15
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Khan MI, Ashfaq F, Alsayegh AA, Hamouda A, Khatoon F, Altamimi TN, Alhodieb FS, Beg MMA. Advanced glycation end product signaling and metabolic complications: Dietary approach. World J Diabetes 2023; 14:995-1012. [PMID: 37547584 PMCID: PMC10401445 DOI: 10.4239/wjd.v14.i7.995] [Citation(s) in RCA: 16] [Impact Index Per Article: 8.0] [Reference Citation Analysis] [Abstract] [Key Words] [Track Full Text] [Download PDF] [Journal Information] [Submit a Manuscript] [Subscribe] [Scholar Register] [Received: 01/30/2023] [Revised: 04/08/2023] [Accepted: 04/27/2023] [Indexed: 07/12/2023] Open
Abstract
Advanced glycation end products (AGEs) are a heterogeneous collection of compounds formed during industrial processing and home cooking through a sequence of nonenzymatic glycation reactions. The modern western diet is full of heat-treated foods that contribute to AGE intake. Foods high in AGEs in the contemporary diet include processed cereal products. Due to industrialization and marketing strategies, restaurant meals are modified rather than being traditionally or conventionally cooked. Fried, grilled, baked, and boiled foods have the greatest AGE levels. Higher AGE-content foods include dry nuts, roasted walnuts, sunflower seeds, fried chicken, bacon, and beef. Animal proteins and processed plant foods contain furosine, acrylamide, heterocyclic amines, and 5-hydroxymethylfurfural. Furosine (2-furoil-methyl-lysine) is an amino acid found in cooked meat products and other processed foods. High concentrations of carboxymethyl-lysine, carboxyethyl-lysine, and methylglyoxal-O are found in heat-treated nonvegetarian foods, peanut butter, and cereal items. Increased plasma levels of AGEs, which are harmful chemicals that lead to age-related diseases and physiological aging, diabetes, and autoimmune/inflammatory rheumatic diseases such as systemic lupus erythematosus and rheumatoid arthritis. AGEs in the pathophysiology of metabolic diseases have been linked to individuals with diabetes mellitus who have peripheral nerves with high amounts of AGEs and diabetes has been linked to increased myelin glycation. Insulin resistance and hyperglycemia can impact numerous human tissues and organs, leading to long-term difficulties in a number of systems and organs, including the cardiovascular system. Plasma AGE levels are linked to all-cause mortality in individuals with diabetes who have fatal or nonfatal coronary artery disease, such as ventricular dysfunction. High levels of tissue AGEs are independently associated with cardiac systolic dysfunction in diabetic patients with heart failure compared with diabetic patients without heart failure. It is widely recognized that AGEs and oxidative stress play a key role in the cardiovascular complications of diabetes because they both influence and are impacted by oxidative stress. All chronic illnesses involve protein, lipid, or nucleic acid modifications including crosslinked and nondegradable aggregates known as AGEs. Endogenous AGE formation or dietary AGE uptake can result in additional protein modifications and stimulation of several inflammatory signaling pathways. Many of these systems, however, require additional explanation because they are not entirely obvious. This review summarizes the current evidence regarding dietary sources of AGEs and metabolism-related complications associated with AGEs.
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Affiliation(s)
- Mohammad Idreesh Khan
- Department of Clinical Nutrition, College of Applied Health Sciences in Ar Rass, Qassim University, Ar Rass 51921, Saudi Arabia
| | - Fauzia Ashfaq
- Clinical Nutrition Department, Applied Medical Sciences College, Jazan University, Jazan 82817, Saudi Arabia
| | - Abdulrahman A Alsayegh
- Clinical Nutrition Department, Applied Medical Sciences College, Jazan University, Jazan 82817, Saudi Arabia
| | - Alshaimaa Hamouda
- Clinical Nutrition Department, Applied Medical Sciences College, Jazan University, Jazan 82817, Saudi Arabia
| | - Fahmida Khatoon
- Department of Biochemistry, College of Medicine, University of Hail, Hail 2240, Saudi Arabia
| | - Tahani Nasser Altamimi
- Department of Family and Community Medicine, College of Medicine, University of Hail, Hail 2240, Saudi Arabia
| | - Fahad Saad Alhodieb
- Department of Clinical Nutrition, College of Applied Health Sciences in Ar Rass, Qassim University, Ar Rass 51921, Saudi Arabia
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Artasensi A, Salina E, Fumagalli L, Regazzoni L. A Novel Chromatographic Method to Assess the Binding Ability towards Dicarbonyls. Molecules 2023; 28:5341. [PMID: 37513213 PMCID: PMC10384793 DOI: 10.3390/molecules28145341] [Citation(s) in RCA: 0] [Impact Index Per Article: 0] [Reference Citation Analysis] [Abstract] [Key Words] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Received: 06/16/2023] [Revised: 06/29/2023] [Accepted: 07/10/2023] [Indexed: 07/30/2023] Open
Abstract
Human exposure to dicarbonyls occurs via ingestion (e.g., food), inhalation (e.g., electronic cigarettes) and dysregulation of endogenous metabolic pathways (e.g., glycolysis). Dicarbonyls are electrophiles able to induce carbonylation of endogenous substrate. They have been associated with the onset and progression of several human diseases. Several studies have advocated the use of dicarbonyl binders as food preservatives or as drugs aimed at mitigating carbonylation. This study presents the setup of an easy and cheap assay for the screening of selective and potent dicarbonyl binders. The method is based on the incubation of the candidate molecules with a molecular probe. The activity is then determined by measuring the residual concentration of the molecular probe over time by liquid chromatography (LC). However, the naturally occurring dicarbonyls (e.g., glyoxal, methylglyoxal) are not appealing as probes since they are hard to separate and detect using the most popular LC variants. Benzylglyoxal (BGO) was therefore synthesized and tested, proving to be a convenient probe that allows a direct quantification of residual dicarbonyls by reversed phase LC without derivatization. The method was qualified by assessing the binding ability of some molecules known as binders of natural occurring dicarbonyls, obtaining results consistent with literature.
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Affiliation(s)
- Angelica Artasensi
- Department of Pharmaceutical Sciences, University of Milan, via Mangiagalli 25, 20133 Milan, Italy
| | - Emanuele Salina
- Department of Pharmaceutical Sciences, University of Milan, via Mangiagalli 25, 20133 Milan, Italy
| | - Laura Fumagalli
- Department of Pharmaceutical Sciences, University of Milan, via Mangiagalli 25, 20133 Milan, Italy
| | - Luca Regazzoni
- Department of Pharmaceutical Sciences, University of Milan, via Mangiagalli 25, 20133 Milan, Italy
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17
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Acquaticci L, Angeloni S, Cela N, Galgano F, Vittori S, Caprioli G, Condelli N. Impact of coffee species, post-harvesting treatments and roasting conditions on coffee quality and safety related compounds. Food Control 2023. [DOI: 10.1016/j.foodcont.2023.109714] [Citation(s) in RCA: 0] [Impact Index Per Article: 0] [Reference Citation Analysis] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 03/06/2023]
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18
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Chumroenvidhayakul S, Thilavech T, Abeywardena M, Adisakwattana S. Dragon Fruit Peel Waste ( Hylocereus undatus) as a Potential Ingredient for Reducing Lipid Peroxidation, Dietary Advanced Glycation End Products, and Starch Digestibility in Cookies. Antioxidants (Basel) 2023; 12:antiox12051002. [PMID: 37237868 DOI: 10.3390/antiox12051002] [Citation(s) in RCA: 0] [Impact Index Per Article: 0] [Reference Citation Analysis] [Abstract] [Key Words] [Grants] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Received: 03/10/2023] [Revised: 04/21/2023] [Accepted: 04/24/2023] [Indexed: 05/28/2023] Open
Abstract
Excessive consumption of cookies has been linked to harmful health outcomes owing to the presence of refined carbohydrates and heat-induced toxicants including end products of lipid peroxidation and dietary advanced glycation end products (dAGEs). To address this issue, this study explores the addition of dragon fruit peel powder (DFP), which is rich in phytochemicals and dietary fibers, to cookies as a potential solution to mitigate their adverse effects. The results indicate that adding DFP at 1%, 2%, and 5% w/w of raw cookie dough significantly improves the total phenolic and betacyanin contents and antioxidant activity, as evidenced by increased ferric-reducing antioxidant power. DFP incorporation also led to reductions in malondialdehyde and dAGEs (p < 0.05). Furthermore, the starch digestibility, hydrolysis index, and predicted glycemic index were all reduced in the presence of DFP, with the latter estimate being due to the higher content of undigested starch. Incorporating DFP in cookies resulted in significant changes in their physical properties, including texture and color. However, sensory evaluation indicates that the overall acceptability of the cookies was not negatively impacted by the addition of up to 2% DFP, suggesting that it is a viable option for enhancing the nutritional value of cookies without compromising their palatability. These findings suggest that DFP is a sustainable and healthier ingredient that can improve the antioxidant capacity of cookies while also mitigating the harmful effects of heat-induced toxins.
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Affiliation(s)
- Siriwan Chumroenvidhayakul
- Phytochemical and Functional Food Research Unit for Clinical Nutrition, Department of Nutrition and Dietetics, Faculty of Allied Health Sciences, Chulalongkorn University, Bangkok 10330, Thailand
| | - Thavaree Thilavech
- Department of Food Chemistry, Faculty of Pharmacy, Mahidol University, Bangkok 10400, Thailand
| | | | - Sirichai Adisakwattana
- Phytochemical and Functional Food Research Unit for Clinical Nutrition, Department of Nutrition and Dietetics, Faculty of Allied Health Sciences, Chulalongkorn University, Bangkok 10330, Thailand
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19
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Wang S, Yang Y, Xiao D, Zheng X, Ai B, Zheng L, Sheng Z. Polysaccharides from banana (Musa spp.) blossoms: Isolation, identification and anti-glycation effects. Int J Biol Macromol 2023; 236:123957. [PMID: 36907309 DOI: 10.1016/j.ijbiomac.2023.123957] [Citation(s) in RCA: 6] [Impact Index Per Article: 3.0] [Reference Citation Analysis] [Abstract] [Key Words] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Received: 11/01/2022] [Revised: 01/23/2023] [Accepted: 03/04/2023] [Indexed: 03/13/2023]
Abstract
Musa spp. (banana) is consumed globally as a healthy fruit and improves the immune system. Banana blossoms are a by-product of banana harvesting rich in active substances such as polysaccharides and phenolic compounds; however, these blossoms are typically discarded as waste. In this report, a polysaccharide, MSBP11, was extracted, purified and identified from banana blossoms. MSBP11 is a neutral homogeneous polysaccharide with a molecular mass of ∼214.43 kDa and composed of arabinose and galactose at a ratio of 0.303:0.697. MSBP11 exhibited potent antioxidant and anti-glycation activities in a dose-dependent manner and can be used as a potential natural antioxidant and inhibitor of advanced glycosylation end products (AGEs). In addition, banana blossoms have been shown to decrease the levels of AGEs in chocolate brownies, which might possibly be developed as functional foods for diabetic patients. This study provides a scientific basis to further research the potential application of banana blossoms in functional foods.
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Affiliation(s)
- Shenwan Wang
- Haikou Experimental Station, Chinese Academy of Tropical Agricultural Sciences, Haikou 571101, China
| | - Yang Yang
- Haikou Experimental Station, Chinese Academy of Tropical Agricultural Sciences, Haikou 571101, China
| | - Dao Xiao
- Haikou Experimental Station, Chinese Academy of Tropical Agricultural Sciences, Haikou 571101, China
| | - Xiaoyan Zheng
- Haikou Experimental Station, Chinese Academy of Tropical Agricultural Sciences, Haikou 571101, China
| | - Binling Ai
- Haikou Experimental Station, Chinese Academy of Tropical Agricultural Sciences, Haikou 571101, China
| | - Lili Zheng
- Haikou Experimental Station, Chinese Academy of Tropical Agricultural Sciences, Haikou 571101, China.
| | - Zhanwu Sheng
- Haikou Experimental Station, Chinese Academy of Tropical Agricultural Sciences, Haikou 571101, China.
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20
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Yan S, Wu L, Xue X. α-Dicarbonyl compounds in food products: Comprehensively understanding their occurrence, analysis, and control. Compr Rev Food Sci Food Saf 2023; 22:1387-1417. [PMID: 36789800 DOI: 10.1111/1541-4337.13115] [Citation(s) in RCA: 19] [Impact Index Per Article: 9.5] [Reference Citation Analysis] [Abstract] [Key Words] [MESH Headings] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Received: 07/12/2022] [Revised: 12/31/2022] [Accepted: 01/14/2023] [Indexed: 02/16/2023]
Abstract
α-Dicarbonyl compounds (α-DCs) are readily produced during the heating and storage of foods, mainly through the Maillard reaction, caramelization, lipid-peroxidation, and enzymatic reaction. They contribute to both the organoleptic properties (i.e., aroma, taste, and color) and deterioration of foods and are potential indicators of food quality. α-DCs are also important precursors to hazardous substances, such as acrylamide, furan, advanced lipoxidation end products, and advanced glycation end products, which are genotoxic, neurotoxic, and linked to several diseases. Recent studies have indicated that dietary α-DCs can elevate plasma α-DC levels and lead to "dicarbonyl stress." To accurately assess their health risks, quantifying α-DCs in food products is crucial. Considering their low volatility, inability to absorb ultraviolet light, and high reactivity, the analysis of α-DCs in complex food systems is a challenge. In this review, we comprehensively cover the development of scientific approaches, from extraction, enrichment, and derivatization, to sophisticated detection techniques, which are necessary for quantifying α-DCs in different foods. Exposure to α-DCs is inevitable because they exist in most foods. Recently, novel strategies for reducing α-DC levels in foods have become a hot research topic. These strategies include the use of new processing technologies, formula modification, and supplementation with α-DC scavengers (e.g., phenolic compounds). For each strategy, it is important to consider the potential mechanisms underlying the formation and removal of process contaminants. Future studies are needed to develop techniques to control α-DC formation during food processing, and standardized approaches are needed to quantify and compare α-DCs in different foods.
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Affiliation(s)
- Sha Yan
- Institute of Apicultural Research, Chinese Academy of Agricultural Sciences, Beijing, China
- College of Food Science and Engineering, Shanxi Agricultural University, Taigu, China
| | - Liming Wu
- Institute of Apicultural Research, Chinese Academy of Agricultural Sciences, Beijing, China
| | - Xiaofeng Xue
- Institute of Apicultural Research, Chinese Academy of Agricultural Sciences, Beijing, China
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21
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Zhan F, Luo J, Sun Y, Hu Y, Fan X, Pan D. Antioxidant Activity and Cell Protection of Glycosylated Products in Different Reducing Sugar Duck Liver Protein Systems. Foods 2023; 12:foods12030540. [PMID: 36766069 PMCID: PMC9914316 DOI: 10.3390/foods12030540] [Citation(s) in RCA: 0] [Impact Index Per Article: 0] [Reference Citation Analysis] [Abstract] [Key Words] [Track Full Text] [Figures] [Journal Information] [Subscribe] [Scholar Register] [Received: 11/23/2022] [Revised: 01/20/2023] [Accepted: 01/23/2023] [Indexed: 01/28/2023] Open
Abstract
Duck liver is an important by-product of duck food. In this study, we investigated the effects of glucose, fructose, and xylose on the antioxidant properties of glycosylated products of duck liver protein and their protective effects on HepG2 cells. The results show that the glycosylation products of the three duck liver proteins (DLP-G, DLP-F, and DLP-X) all exhibit strong antioxidant activity; among three groups, DLP-X shows the strongest ability to scavenge DPPH, ·OH free radicals, and ABTS+ free radicals. The glycosylated products of duck liver protein are not toxic to HepG2 cells and significantly increase the activity of antioxidant enzymes such as SOD, CAT, and GSH-Px in HepG2 cells at the concentration of 2.0 g/L, reducing oxidative stress damage of cells (p < 0.05). DLP-X has a better effect in reducing oxidative damage and increasing cellular activity in HepG2 cells than DLP-G and DLP-F (p < 0.05). In this study, the duck liver protein glycosylated products by glucose, fructose, and xylose were named as DLP-G, DLP-F, and DLP-X, respectively.
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Affiliation(s)
- Feili Zhan
- Key Laboratory of Animal Protein Food Processing Technology of Zhejiang Province, College of Food and Pharmaceutical Sciences, Ningbo University, Ningbo 315211, China
- State Key Laboratory for Managing Biotic and Chemical Threats to the Quality and Safety of Agro-Products, Ningbo University, Ningbo 315211, China
| | - Jiafeng Luo
- Key Laboratory of Animal Protein Food Processing Technology of Zhejiang Province, College of Food and Pharmaceutical Sciences, Ningbo University, Ningbo 315211, China
- State Key Laboratory for Managing Biotic and Chemical Threats to the Quality and Safety of Agro-Products, Ningbo University, Ningbo 315211, China
| | - Yangying Sun
- Key Laboratory of Animal Protein Food Processing Technology of Zhejiang Province, College of Food and Pharmaceutical Sciences, Ningbo University, Ningbo 315211, China
- State Key Laboratory for Managing Biotic and Chemical Threats to the Quality and Safety of Agro-Products, Ningbo University, Ningbo 315211, China
| | - Yangyang Hu
- Key Laboratory of Animal Protein Food Processing Technology of Zhejiang Province, College of Food and Pharmaceutical Sciences, Ningbo University, Ningbo 315211, China
- State Key Laboratory for Managing Biotic and Chemical Threats to the Quality and Safety of Agro-Products, Ningbo University, Ningbo 315211, China
| | - Xiankang Fan
- Key Laboratory of Animal Protein Food Processing Technology of Zhejiang Province, College of Food and Pharmaceutical Sciences, Ningbo University, Ningbo 315211, China
- State Key Laboratory for Managing Biotic and Chemical Threats to the Quality and Safety of Agro-Products, Ningbo University, Ningbo 315211, China
| | - Daodong Pan
- Key Laboratory of Animal Protein Food Processing Technology of Zhejiang Province, College of Food and Pharmaceutical Sciences, Ningbo University, Ningbo 315211, China
- State Key Laboratory for Managing Biotic and Chemical Threats to the Quality and Safety of Agro-Products, Ningbo University, Ningbo 315211, China
- Correspondence: ; Tel.: +86-135-6789-6492
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22
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Liu W, Wang Y, Xu D, Hu H, Huang Y, Liu Y, Nie S, Li C, Xie M. Investigation on the contents of heat-induced hazards in commercial nuts. Food Res Int 2023; 163:112041. [PMID: 36596086 DOI: 10.1016/j.foodres.2022.112041] [Citation(s) in RCA: 3] [Impact Index Per Article: 1.5] [Reference Citation Analysis] [Abstract] [Key Words] [MESH Headings] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Received: 07/14/2022] [Revised: 09/24/2022] [Accepted: 10/10/2022] [Indexed: 02/03/2023]
Abstract
The purpose was to investigate the contents of heat-induced hazards by liquid chromatography-tandem mass spectrometry (LC-MS/MS) in 44 commercial nuts. Results showed that content ranges of Acrylamide (AA), 5-hydroxymethylfurfural (5-HMF), Nε-carboxymethyl-lysine (CML), Nε-carboxyethyl-lysine (CEL), 3-Deoxyglucosone (3-DG), Glyoxal (GO), and Methylglyoxal (MGO) were ND-123.57 µg/kg, 0.57-213.42 mg/kg, 3.18-18.67 mg/kg, 3.98-57.85 mg/kg, 1.5-133.86 mg/kg, 0.45-1.59 mg/kg and 0.29-13.84 mg/kg, respectively. Sunflower seeds contained more heat-induced hazards followed by pistachios, cashews, almonds, walnuts and hazelnuts. The content of 5-HMF was positively correlated with the content of 3-DG. CML exhibited positive correlation with content of GO while no correlation between CEL and MGO. Higher levels of 3-DG and 5-HMF were observed in nuts produced with sugar and honey. Deep processing had a stronger promoting effect on CML and CEL formation. These data could provide a crucial guide for consumers to select nut products which might reduce heat-induced hazards intake.
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Affiliation(s)
- Wenting Liu
- State Key Laboratory of Food Science and Technology, China-Canada Joint Lab of Food Science and Technology (Nanchang), Key Laboratory of Bioactive Polysaccharides of Jiangxi Province, Nanchang University, Nanchang 330047, Jiangxi, China
| | - Yuting Wang
- State Key Laboratory of Food Science and Technology, China-Canada Joint Lab of Food Science and Technology (Nanchang), Key Laboratory of Bioactive Polysaccharides of Jiangxi Province, Nanchang University, Nanchang 330047, Jiangxi, China.
| | - Dechang Xu
- State Key Laboratory of Food Science and Technology, China-Canada Joint Lab of Food Science and Technology (Nanchang), Key Laboratory of Bioactive Polysaccharides of Jiangxi Province, Nanchang University, Nanchang 330047, Jiangxi, China
| | - Huiyu Hu
- State Key Laboratory of Food Science and Technology, China-Canada Joint Lab of Food Science and Technology (Nanchang), Key Laboratory of Bioactive Polysaccharides of Jiangxi Province, Nanchang University, Nanchang 330047, Jiangxi, China
| | - Yilun Huang
- State Key Laboratory of Food Science and Technology, China-Canada Joint Lab of Food Science and Technology (Nanchang), Key Laboratory of Bioactive Polysaccharides of Jiangxi Province, Nanchang University, Nanchang 330047, Jiangxi, China
| | - Yuwei Liu
- State Key Laboratory of Food Science and Technology, China-Canada Joint Lab of Food Science and Technology (Nanchang), Key Laboratory of Bioactive Polysaccharides of Jiangxi Province, Nanchang University, Nanchang 330047, Jiangxi, China
| | - Shaoping Nie
- State Key Laboratory of Food Science and Technology, China-Canada Joint Lab of Food Science and Technology (Nanchang), Key Laboratory of Bioactive Polysaccharides of Jiangxi Province, Nanchang University, Nanchang 330047, Jiangxi, China
| | - Chang Li
- State Key Laboratory of Food Science and Technology, China-Canada Joint Lab of Food Science and Technology (Nanchang), Key Laboratory of Bioactive Polysaccharides of Jiangxi Province, Nanchang University, Nanchang 330047, Jiangxi, China
| | - Mingyong Xie
- State Key Laboratory of Food Science and Technology, China-Canada Joint Lab of Food Science and Technology (Nanchang), Key Laboratory of Bioactive Polysaccharides of Jiangxi Province, Nanchang University, Nanchang 330047, Jiangxi, China.
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23
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Hazardous Chemical Compounds in Cookies: The Role of Sugars and the Kinetics of Their Formation during Baking. Foods 2022; 11:foods11244066. [PMID: 36553808 PMCID: PMC9777895 DOI: 10.3390/foods11244066] [Citation(s) in RCA: 0] [Impact Index Per Article: 0] [Reference Citation Analysis] [Abstract] [Key Words] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Received: 11/07/2022] [Revised: 12/08/2022] [Accepted: 12/13/2022] [Indexed: 12/23/2022] Open
Abstract
Baking goods are an essential part of the diet worldwide and are consumed daily, so they represent ideal foods for vehicle health- and unhealth-promoting substances. This work aimed to study the influence of sugars and baking conditions of cookies on the final levels of the main reported hazardous chemical compounds such as 5-hydroxymethylfurfural (HMF), 3-deoxyglucosone (3-DG), glyoxal (GO) and methylglyoxal (MGO). The replacement of sucrose with fructose or glucose in the cookies recipe deeply modifies the levels of α-dicarbonyl compounds (DCs), particularly 3-DG, independently of the baking temperature used. A longer baking time, even a few minutes, can drastically modify the HMF level in cookies and the use of fructose or glucose in the recipe seems to ensure the optimal conditions for generating this compound. The use of sucrose is required to keep levels of the hazardous compounds below a few mg/kg. Additionally, the ability to retain water, the titratable acidity and/or the pH of the final products were influenced by the used sugars with effects on the final levels of DCs and HMF. The highest Ea values determined for DCs and HMF formation in the cookies with sucrose suggest that this system requires very high temperatures to increase meaningful levels of these molecules, limiting their accumulation.
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24
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Lu WC, Cheng YT, Chan YJ, Li PH. Food safety assessments of acrylamide formation and characterizations of flaky rolls enriched with black rice (Oryza sativa). Front Nutr 2022; 9:1027800. [PMID: 36337666 PMCID: PMC9633999 DOI: 10.3389/fnut.2022.1027800] [Citation(s) in RCA: 0] [Impact Index Per Article: 0] [Reference Citation Analysis] [Abstract] [Grants] [Track Full Text] [Download PDF] [Figures] [Journal Information] [Subscribe] [Scholar Register] [Received: 08/25/2022] [Accepted: 10/06/2022] [Indexed: 11/24/2022] Open
Abstract
This study aims to investigate the physicochemical composition, textural parameters, and chemical constituent of flaky rolls incorporated with different proportions of black rice flour. According to farinographic characteristics, the addition of black rice flour could reduce the stability and increase the dough development time and water absorption (%). While for the extensographic properties, addition of black rice flour resulted in significantly different maximum resistance to extension (BU) and extensibility (cm) vs. the control. With the addition of black rice flour in flaky rolls, the crude protein, total dietary fiber (TDF), soluble dietary fiber (SDF), and insoluble dietary fiber (IDF) were significantly improved. Glucose released was much lower with 10 and 20% black rice than the control and 5% black rice because of the higher black rice inclusion. With increasing black rice incorporation, total anthocyanin content, and antioxidant capacity was also improved. The content of asparagine, acrylamide, hydroxymethylfurfural (HMF), furfural, methylglyoxal, and glyoxal in flaky rolls was also increased. The proper content of black rice flour (5%) could significantly enhance the stability of the dough properties; control the final volume, texture, and appearance; and retain good protein and fiber composition, antioxidant capacity, and overall acceptance of the flaky roll.
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Affiliation(s)
- Wen-Chien Lu
- Department of Food and Beverage Management, Chung-Jen Junior College of Nursing, Health Sciences and Management, Chiayi City, Taiwan
| | - Yu-Tsung Cheng
- Cardiovascular Center, Taichung Veterans General Hospital, Taichung, Taiwan
| | - Yung-Jia Chan
- College of Biotechnology and Bioresources, Da-Yeh University, Changhua, Taiwan
| | - Po-Hsien Li
- Department of Food and Nutrition, Providence University, Taichung, Taiwan
- *Correspondence: Po-Hsien Li
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25
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Liu D, Chen J, Xie Y, Mei X, Xu C, Liu J, Cao X. Investigating the molecular mechanisms of glyoxal-induced cytotoxicity in human embryonic kidney cells: Insights from network toxicology and cell biology experiments. ENVIRONMENTAL TOXICOLOGY 2022; 37:2269-2280. [PMID: 35621379 DOI: 10.1002/tox.23593] [Citation(s) in RCA: 7] [Impact Index Per Article: 2.3] [Reference Citation Analysis] [Abstract] [Key Words] [MESH Headings] [Track Full Text] [Subscribe] [Scholar Register] [Received: 02/21/2022] [Revised: 04/28/2022] [Accepted: 05/14/2022] [Indexed: 06/15/2023]
Abstract
Glyoxal, a reactive carbonyl species, can be generated both endogenously (glucose metabolism) and exogenously (cigarette smoke and food system). Increasing evidence demonstrates that glyoxal exacerbates the development and progression of diabetic nephropathy, but the underlying mechanisms of glyoxal toxicity to human embryonic kidney (HEK293) cells remain unclear. In this work, the molecular mechanisms of glyoxal-induced cytotoxicity in HEK293 cells were explored with network toxicology and cell biology experiments. Network toxicology results showed that oxidative stress and advanced glycation end products (AGEs)/RAGE signaling pathways played a crucial role in glyoxal toxicity. Next, further validation was performed at the cellular level. Glyoxal activated the AGEs-RAGE signaling pathway, caused the increase of cellular ROS, and activated the p38MAPK and JNK signaling pathways, causing cellular oxidative stress. Furthermore, glyoxal caused the activation of the NF-κB signaling pathway and increased the expression of TGF-β1, indicating that glyoxal caused cellular inflammation. Moreover, glyoxal caused cellular DNA damage accompanied by the activation of DNA damage response pathways. Finally, the mitochondrial apoptosis pathway was activated. The results that obtained in cell biology were consistent with network toxicology, which corroborated each other and together indicated that glyoxal induced HEK293 cells damage via the process of oxidative stress, the AGEs-RAGE pathway, and their associated signaling pathways. This study provides the experimental basis for the cytotoxicity of glyoxal on HEK293 cells.
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Affiliation(s)
- Dan Liu
- School of life Science, Liaoning University, Shenyang, China
| | - Junliang Chen
- School of life Science, Liaoning University, Shenyang, China
| | - Yanzhen Xie
- School of life Science, Liaoning University, Shenyang, China
| | - Xueying Mei
- School of life Science, Liaoning University, Shenyang, China
| | - Chengbin Xu
- School of Environment Science, Liaoning University, Shenyang, China
| | - Jianli Liu
- School of life Science, Liaoning University, Shenyang, China
| | - Xiangyu Cao
- School of life Science, Liaoning University, Shenyang, China
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26
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Herraiz T, Peña A, Mateo H, Herraiz M, Salgado A. Formation, Characterization, and Occurrence of β-Carboline Alkaloids Derived from α-Dicarbonyl Compounds and l-Tryptophan. JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY 2022; 70:9143-9153. [PMID: 35819924 PMCID: PMC9335879 DOI: 10.1021/acs.jafc.2c03187] [Citation(s) in RCA: 20] [Impact Index Per Article: 6.7] [Reference Citation Analysis] [Abstract] [Key Words] [MESH Headings] [Grants] [Track Full Text] [Figures] [Subscribe] [Scholar Register] [Indexed: 06/15/2023]
Abstract
β-Carbolines (βCs) are naturally occurring bioactive alkaloids, whereas α-dicarbonyl compounds are reactive substances generated in foods and in vivo. In this work, l-tryptophan reacted with α-dicarbonyl compounds affording new β-carbolines. Glyoxal afforded 1-hydroxymethyl-β-carboline (HME-βC) and its 3-carboxylic acid, and methylglyoxal afforded 1-(1-hydroxyethyl)-β-carboline (HET-βC) and its 3-carboxylic acid. 3-Deoxyglucosone afforded 1-(1,3,4,5-tetrahydroxypent-1-yl)-β-carboline isomers (1a/b), 1-(1,4,5-trihydroxypent-1-yl)-β-carboline (2), and 1-(1,5-dihydroxypent-3-en-1-yl)-β-carboline (3). The formation of these βCs increased under acidic conditions and with increasing temperature. A mechanism is proposed explaining the conversion of a carbonyl into a hydroxy group based on tautomerism and cyclization to the dihydro-βC-3-COOH intermediates, which were isolated and gave the βCs. These α-dicarbonyl-derived βCs occurred in model reactions of l-tryptophan with fructose or glucose incubated under heating and can be considered as advanced glycation end products (AGEs). They were also present in foods and formed during heating processes. HET-βC appeared in processed foods, reaching up to 309 ng/g, with the highest amount found in dried tomato, fried onion, toasted bread, and Manuka honey. HME-βC was only detected in some foods with lower amounts than HET-βC. HET-βC appeared in foods as a racemic mixture of enantiomers suggesting the same mechanism of formation as the synthetized product. α-Dicarbonyl-derived βCs (HET-βC, HME-βC, and 1a/b-3) occur in foods and food processing and, therefore, they are ingested during diet.
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Affiliation(s)
- Tomás Herraiz
- Spanish
National Research Council (CSIC), Instituto
de Ciencia y Tenología de Alimentos y Nutrición (ICTAN-CSIC), Jose Antonio Novais 10, Ciudad Universitaria, 28040 Madrid, Spain
| | - Adriana Peña
- Spanish
National Research Council (CSIC), Instituto
de Ciencia y Tenología de Alimentos y Nutrición (ICTAN-CSIC), Jose Antonio Novais 10, Ciudad Universitaria, 28040 Madrid, Spain
| | - Haroll Mateo
- Spanish
National Research Council (CSIC), Instituto
de Ciencia y Tenología de Alimentos y Nutrición (ICTAN-CSIC), Jose Antonio Novais 10, Ciudad Universitaria, 28040 Madrid, Spain
| | - Marta Herraiz
- Spanish
National Research Council (CSIC), Instituto
de Ciencia y Tenología de Alimentos y Nutrición (ICTAN-CSIC), Jose Antonio Novais 10, Ciudad Universitaria, 28040 Madrid, Spain
| | - Antonio Salgado
- Centro
de Espectroscopía de RMN (CERMN), Universidad de Alcalá (UAH), Campus Universitario Ctra. Madrid-Barcelona km
33.6, 28805 Alcalá
de Henares, Madrid, Spain
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27
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Revealing inhibitory mechanism of thiamine on the formation of 2-amino-3,8-dimethylimidazo[4,5-f] quinoxaline based on quantum chemistry calculations and experimental verification. Lebensm Wiss Technol 2022. [DOI: 10.1016/j.lwt.2022.113552] [Citation(s) in RCA: 0] [Impact Index Per Article: 0] [Reference Citation Analysis] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 11/22/2022]
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28
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Effects of baking factors and recipes on the quality of butter cookies and the formation of advanced glycation end products (AGEs) and 5-hydroxymethylfurfural (HMF). Curr Res Food Sci 2022; 5:940-948. [PMID: 35677649 PMCID: PMC9168048 DOI: 10.1016/j.crfs.2022.05.012] [Citation(s) in RCA: 15] [Impact Index Per Article: 5.0] [Reference Citation Analysis] [Abstract] [Track Full Text] [Download PDF] [Figures] [Journal Information] [Subscribe] [Scholar Register] [Received: 03/07/2022] [Revised: 04/21/2022] [Accepted: 05/20/2022] [Indexed: 11/24/2022] Open
Abstract
Maillard reaction during food processing contributes to the formation of some unpleasant heat-induced toxicants including advanced glycation end products (AGEs) and 5-hydroxymethylfurfural (HMF), which have been linked to various health risks. The effects of baking factors and recipes, such as baking temperature (130°C–180 °C) and time (8 min–15 min), sucrose levels (0 g–20 g), butter levels (0 g–20 g) and egg liquid levels (0 g–12 g) on the formation of free Nε-(carboxymethyl)lysine (CML), free Nε-(carboxyethyl)lysine (CEL), protein-bound CML, protein-bound CEL, HMF, glyoxal (GO), methylglyoxal (MGO), 3-deoxyglucosone (3-DG) and on the sensory qualities were investigated in butter cookies. The results suggested that the levels of AGEs initially increased and then followed by decrease as baking temperature and time increased, HMF is very sensitive to baking temperature and time and grows sharply. The changes of protein-bound AGEs are lagging behind that of free AGEs. The proportions of sucrose, butter and egg liquid in butter cookies were positively correlated with AGEs, with sucrose greatly promoting on the formation of HMF and 3-DG. In addition, the high level of sucrose and butter in cookies is preferred by panelists, especially in terms of appearance, taste and smell.
AGEs increases and then decreases as baking temperature and time increased. HMF is very sensitive to baking temperature and time in butter cookies. The changes of protein-bound AGEs are lagging behind that of free AGEs. Sucrose greatly promotes the formation of HMF and 3-DG. Sucrose and butter promotes release of α-dicarbonyl compounds.
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29
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Nε-carboxymethyl-lysine and Nε-carboxyethyl-lysine contents in commercial meat products. Food Res Int 2022; 155:111048. [PMID: 35400433 DOI: 10.1016/j.foodres.2022.111048] [Citation(s) in RCA: 16] [Impact Index Per Article: 5.3] [Reference Citation Analysis] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Received: 07/15/2021] [Revised: 02/10/2022] [Accepted: 02/18/2022] [Indexed: 01/13/2023]
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30
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Wei J, Wu Z, Chai T, He F, Chen Y, Dong X, Shi Y. Effect of the combination of low temperature vacuum heating with tea polyphenol on AGEs in sturgeon fillets. Int J Food Sci Technol 2022. [DOI: 10.1111/ijfs.15721] [Citation(s) in RCA: 1] [Impact Index Per Article: 0.3] [Reference Citation Analysis] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 02/07/2023]
Affiliation(s)
- Jianling Wei
- School of Food Science and Biotechnology Zhejiang Gongshang University Hangzhou Zhejiang 310035 China
- Zhejiang Provincial Collaborative Innovation Center of Food Safety and Nutrition Zhejiang Gongshang University Hangzhou Zhejiang 310035 China
| | - Zhengyang Wu
- School of Food Science and Biotechnology Zhejiang Gongshang University Hangzhou Zhejiang 310035 China
- Zhejiang Provincial Collaborative Innovation Center of Food Safety and Nutrition Zhejiang Gongshang University Hangzhou Zhejiang 310035 China
| | - Tingting Chai
- School of Food Science and Biotechnology Zhejiang Gongshang University Hangzhou Zhejiang 310035 China
- Zhejiang Provincial Collaborative Innovation Center of Food Safety and Nutrition Zhejiang Gongshang University Hangzhou Zhejiang 310035 China
| | - Fanyu He
- School of Food Science and Biotechnology Zhejiang Gongshang University Hangzhou Zhejiang 310035 China
- Zhejiang Provincial Collaborative Innovation Center of Food Safety and Nutrition Zhejiang Gongshang University Hangzhou Zhejiang 310035 China
| | - Yuewen Chen
- School of Food Science and Biotechnology Zhejiang Gongshang University Hangzhou Zhejiang 310035 China
- Zhejiang Provincial Collaborative Innovation Center of Food Safety and Nutrition Zhejiang Gongshang University Hangzhou Zhejiang 310035 China
| | - Xiuping Dong
- School of Food Science and Technology Dalian Polytechnic University Dalian 116034 China
- National Engineering Research Center of Seafood Dalian 116034 China
| | - Yugang Shi
- School of Food Science and Biotechnology Zhejiang Gongshang University Hangzhou Zhejiang 310035 China
- Zhejiang Provincial Collaborative Innovation Center of Food Safety and Nutrition Zhejiang Gongshang University Hangzhou Zhejiang 310035 China
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31
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Zhang Z, Cheng W, Wang X, Wang M, Chen F, Cheng KW. A novel formation pathway of N ε-(carboxyethyl)lysine from lactic acid during high temperature exposure in wheat sourdough bread and chemical model. Food Chem 2022; 388:132942. [PMID: 35447583 DOI: 10.1016/j.foodchem.2022.132942] [Citation(s) in RCA: 7] [Impact Index Per Article: 2.3] [Reference Citation Analysis] [Abstract] [Key Words] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Received: 12/19/2021] [Revised: 03/24/2022] [Accepted: 04/07/2022] [Indexed: 11/04/2022]
Abstract
Nε-(carboxymethyl)lysine (CML) and Nε-(carboxyethyl)lysine (CEL) have been the most extensively studied advanced glycation end-products (AGEs) in foods. Their formation mechanism, especially the latter, has not been clearly delineated in fermented food. In this work, the relative contents of CEL and CML were evaluated in a sourdough-bread and a silica solid chemical model. Lactic acid (LA) content in the sourdough increased with fermentation time that was accompanied by an increase in CEL, but not CML content in the bread. The role of LA as a precursor for CEL was supported by a positive significant correlation between LA and CEL contents, and further analysis using isotope-labeled LA (LA-13C3) revealed that the three carbon atoms of LA were incorporated into CEL. These findings for the first time indicate LA may function as a precursor to promote CEL formation in sourdough bread that merits further investigation.
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Affiliation(s)
- Zhongfei Zhang
- Shenzhen Key Laboratory of Marine Microbiome Engineering, Institute for Advanced Study, Shenzhen University, Shenzhen 518060, China; Key Laboratory of Optoelectronic Devices and Systems, College of Physics and Optoelectronic Engineering, Shenzhen University, Shenzhen 518060, China; Institute for Innovative Development of Food Industry, Shenzhen University, Shenzhen 518060, China
| | - Weiwei Cheng
- Shenzhen Key Laboratory of Marine Microbiome Engineering, Institute for Advanced Study, Shenzhen University, Shenzhen 518060, China; Institute for Innovative Development of Food Industry, Shenzhen University, Shenzhen 518060, China
| | - Xiaowen Wang
- Shenzhen Key Laboratory of Marine Microbiome Engineering, Institute for Advanced Study, Shenzhen University, Shenzhen 518060, China; Institute for Innovative Development of Food Industry, Shenzhen University, Shenzhen 518060, China
| | - Mingfu Wang
- Shenzhen Key Laboratory of Marine Microbiome Engineering, Institute for Advanced Study, Shenzhen University, Shenzhen 518060, China; Institute for Innovative Development of Food Industry, Shenzhen University, Shenzhen 518060, China
| | - Feng Chen
- Shenzhen Key Laboratory of Marine Microbiome Engineering, Institute for Advanced Study, Shenzhen University, Shenzhen 518060, China; Institute for Innovative Development of Food Industry, Shenzhen University, Shenzhen 518060, China
| | - Ka-Wing Cheng
- Shenzhen Key Laboratory of Marine Microbiome Engineering, Institute for Advanced Study, Shenzhen University, Shenzhen 518060, China; Institute for Innovative Development of Food Industry, Shenzhen University, Shenzhen 518060, China.
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32
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Yaman M, Demirci M, Ede-Cintesun E, Kurt E, Faruk Mızrak Ö. Investigation of formation of well-known AGEs precursors in cookies using an in vitro simulated gastrointestinal digestive system. Food Chem 2022; 373:131451. [PMID: 34717081 DOI: 10.1016/j.foodchem.2021.131451] [Citation(s) in RCA: 6] [Impact Index Per Article: 2.0] [Reference Citation Analysis] [Abstract] [Key Words] [MESH Headings] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Received: 04/16/2021] [Revised: 09/21/2021] [Accepted: 10/18/2021] [Indexed: 02/05/2023]
Abstract
The present study investigated the influence of in vitro stimulated digestion system on the content of glyoxal and methylglyoxal in commercial cookies. Glyoxal and methylglyoxal levels in different cookie samples were analyzed before and after in vitro digestion with High Performance Liquid Chromatography. Initial glyoxal and methylglyoxal values ranged between 42.9 and 126.6 µg/100 g, and between 22.9 and 507.3 µg/100 g, respectively. After in vitro digestion, formation of glyoxal and methylglyoxal values were increased up to 645% and 698%, respectively. The results revealed that in vitro stimulated digestion conditions strongly increased the amount of glyoxal and methylglyoxal in cookies. The amount of fructose was found to be more effective on the formation of both GO and MGO than those of glucose and sucrose. Further studies are needed to extensively investigate glyoxal and methylglyoxal formation under in vitro conditions in such foods.
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Affiliation(s)
- Mustafa Yaman
- Faculty of Health Sciences, Department of Nutrition and Dietetics, Istanbul Sabahattin Zaim University, Turkey
| | - Mehmet Demirci
- Faculty of Health Sciences, Department of Nutrition and Dietetics, Istanbul Sabahattin Zaim University, Turkey
| | - Elif Ede-Cintesun
- Faculty of Health Sciences, Department of Nutrition and Dietetics, Istanbul Sabahattin Zaim University, Turkey; Institue of Health Sciences, Department of Nutrition and Dietetics, Istanbul Medipol University, Turkey.
| | - Edanur Kurt
- Faculty of Health Sciences, Department of Nutrition and Dietetics, Istanbul Sabahattin Zaim University, Turkey
| | - Ömer Faruk Mızrak
- Faculty of Health Sciences, Department of Nutrition and Dietetics, Istanbul Sabahattin Zaim University, Turkey
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33
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The Influence of Intracellular Glutathione Levels on the Induction of Nrf2-Mediated Gene Expression by α-Dicarbonyl Precursors of Advanced Glycation End Products. Nutrients 2022; 14:nu14071364. [PMID: 35405976 PMCID: PMC9003139 DOI: 10.3390/nu14071364] [Citation(s) in RCA: 6] [Impact Index Per Article: 2.0] [Reference Citation Analysis] [Abstract] [Key Words] [Track Full Text] [Download PDF] [Figures] [Journal Information] [Subscribe] [Scholar Register] [Received: 03/01/2022] [Revised: 03/18/2022] [Accepted: 03/21/2022] [Indexed: 12/03/2022] Open
Abstract
α-Dicarbonyl compounds, particularly methylglyoxal (MGO), glyoxal (GO), and 3-deoxyglucosone (3-DG), are highly reactive precursors for the formation of advanced glycation end products (AGEs). They are formed in vivo and during food processing. This study aimed to investigate the role of intracellular glutathione (GSH) levels in the induction of Nrf2-mediated gene expression by α-dicarbonyl compounds. The reactions between α-dicarbonyl compounds (MGO, GO, and 3-DG) and GSH were studied by LC-MS in a cell-free system. It was shown that these three α-dicarbonyl compounds react instantaneously with GSH, with the GSH-mediated scavenging decreasing in the order MGO > GO > 3DG. Furthermore, in a cell-based reporter gene assay MGO, GO, and 3-DG were able to induce Nrf2-mediated gene expression in a dose-dependent manner. Modulation of intracellular GSH levels showed that the cytotoxicity and induction of the Nrf2-mediated pathway by MGO, GO and 3-DG was significantly enhanced by depletion of GSH, while a decrease in Nrf2-activation by MGO and GO but not 3-DG was observed upon an increase of the cellular GSH levels. Our results reveal subtle differences in the role of GSH in protection against the three typical α-dicarbonyl compounds and in their induction of Nrf2-mediated gene expression, and point at a dual biological effect of the α-dicarbonyl compounds, being reactive toxic electrophiles and -as a consequence- able to induce Nrf2-mediated protective gene expression, with MGO being most reactive.
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34
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Food-Related Carbonyl Stress in Cardiometabolic and Cancer Risk Linked to Unhealthy Modern Diet. Nutrients 2022; 14:nu14051061. [PMID: 35268036 PMCID: PMC8912422 DOI: 10.3390/nu14051061] [Citation(s) in RCA: 16] [Impact Index Per Article: 5.3] [Reference Citation Analysis] [Abstract] [Track Full Text] [Download PDF] [Figures] [Journal Information] [Subscribe] [Scholar Register] [Received: 02/05/2022] [Revised: 02/28/2022] [Accepted: 03/01/2022] [Indexed: 02/01/2023] Open
Abstract
Carbonyl stress is a condition characterized by an increase in the steady-state levels of reactive carbonyl species (RCS) that leads to accumulation of their irreversible covalent adducts with biological molecules. RCS are generated by the oxidative cleavage and cellular metabolism of lipids and sugars. In addition to causing damage directly, the RCS adducts, advanced glycation end-products (AGEs) and advanced lipoxidation end-products (ALEs), cause additional harm by eliciting chronic inflammation through receptor-mediated mechanisms. Hyperglycemia- and dyslipidemia-induced carbonyl stress plays a role in diabetic cardiovascular complications and diabetes-related cancer risk. Moreover, the increased dietary exposure to AGEs/ALEs could mediate the impact of the modern, highly processed diet on cardiometabolic and cancer risk. Finally, the transient carbonyl stress resulting from supraphysiological postprandial spikes in blood glucose and lipid levels may play a role in acute proinflammatory and proatherogenic changes occurring after a calorie dense meal. These findings underline the potential importance of carbonyl stress as a mediator of the cardiometabolic and cancer risk linked to today’s unhealthy diet. In this review, current knowledge in this field is discussed along with future research courses to offer new insights and open new avenues for therapeutic interventions to prevent diet-associated cardiometabolic disorders and cancer.
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35
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Jana A, Baruah M, Samanta A. Activity-based fluorescent probes for sensing and imaging of Reactive Carbonyl species (RCSs). Chem Asian J 2022; 17:e202200044. [PMID: 35239996 DOI: 10.1002/asia.202200044] [Citation(s) in RCA: 5] [Impact Index Per Article: 1.7] [Reference Citation Analysis] [Abstract] [Key Words] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Received: 01/17/2022] [Revised: 03/03/2022] [Indexed: 11/08/2022]
Abstract
This review explains various strategies for developing fluorescent probes to detect reactive carbonyl species (RCS). There are sevaral number of mono and diacarbonyls among 30 varieties of reactive carbonyl species (RCSs) so far discovered, which play pivotal roles in pathological processes such as cancer, neurodegenerative diseases, cardiovascular disease, renal failure, and diabetes mellitus. These RCSs play essential roles in maintaining ion channels regulation, cellular signaling pathways, and metabolisms. Among RCSs, Carbon moxide (CO) is also utilized for its cardioprotective, anti-inflammatory, and anti-apoptotic effects. Fluorescence-based non-invasive optical tools have come out as one of the promising methods for analyzing the concentrations and co-localizations of these small metabolites. There has been a tremendous eruption in developing fluorescent probes for selective detection of specific RCSs within cellular and aqueous environments due to its high sensitivity, high spatial and temporal resolution of fluorescence imaging. Fluorescence-based sensing mechanisms such as intramolecular charge transfer (ICT), photoinduced electron transfer (PeT), excited-state intramolecular proton transfer (ESIPT), and fluorescence resonance energy transfer (FRET) are described. In particular, probes for dicarbonyls such as methylglyoxal (MGO), malondialdehyde (MDA), along with monocarbonyls that include formaldehyde (FA), carbon monoxide (CO) and phosgene are discussed. One of the most exciting advances in this review is the summary of fluorescent probes of dicarbonyl compounds.
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Affiliation(s)
- Anal Jana
- Shiv Nadar University, Chemistry, INDIA
| | | | - Animesh Samanta
- Shiv Nadar University, CHEMISTRY, NH 91, TEHSIL DADRI, GAUSTAM BUDHA NAGAR, 201314, GREATER NOIDA, INDIA
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36
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Huang Y, Lu J, Li M, Li C, Wang Y, Shen M, Chen Y, Nie S, Zeng M, Chen J, Xie M. Effect of acidity regulators on acrylamide and 5-hydroxymethylfurfural formation in French fries: The dual role of pH and acid radical ion. Food Chem 2022; 371:131154. [PMID: 34598120 DOI: 10.1016/j.foodchem.2021.131154] [Citation(s) in RCA: 10] [Impact Index Per Article: 3.3] [Reference Citation Analysis] [Abstract] [Key Words] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Received: 01/24/2021] [Revised: 08/21/2021] [Accepted: 09/14/2021] [Indexed: 11/04/2022]
Abstract
The influence of acidity regulators and buffers on the formation of acrylamide (AA) and 5-hydroxymethylfurfural (5-HMF) in French fries and the underlying mechanism were evaluated. Prior to frying, the potato strips were dipped in the corresponding acidity regulator solutions or buffers for 30 min at room temperature. The results showed that acids inhibited AA formation, but increased 5-HMF levels. The AA level decreased and 5-HMF level increased with decreasing pH of potato strips. Interestingly, increasing concentration of acid radical ions resulted in AA increase and 5-HMF decrease, which was opposite to the acidification effect of citric acid and acetic acid. Both pH and acid radical ion were important factors for AA and 5-HMF formation. Moreover, acidity regulators might impact AA formation by acting on the generation of methylglyoxal (MGO) and glyoxal (GO) and impact 5-HMF formation by acting on the generation of 3-deoxyglucosone (3-DG).
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Affiliation(s)
- Yousheng Huang
- State Key Laboratory of Food Science and Technology, China-Canada Joint Lab of Food Science and Technology (Nanchang), Nanchang University, 235 Nanjing East Road, Nanchang 330047, China; Jiangxi Institute of Analysis and Testing, Nanchang 330029, China; Institute of Development and Research, Jiangxi General Institute of Testing and Certification, Nanchang 330029, China
| | - Jingnan Lu
- State Key Laboratory of Food Science and Technology, China-Canada Joint Lab of Food Science and Technology (Nanchang), Nanchang University, 235 Nanjing East Road, Nanchang 330047, China
| | - Mingyu Li
- State Key Laboratory of Food Science and Technology, China-Canada Joint Lab of Food Science and Technology (Nanchang), Nanchang University, 235 Nanjing East Road, Nanchang 330047, China
| | - Chang Li
- State Key Laboratory of Food Science and Technology, China-Canada Joint Lab of Food Science and Technology (Nanchang), Nanchang University, 235 Nanjing East Road, Nanchang 330047, China
| | - Yuting Wang
- State Key Laboratory of Food Science and Technology, China-Canada Joint Lab of Food Science and Technology (Nanchang), Nanchang University, 235 Nanjing East Road, Nanchang 330047, China
| | - Mingyue Shen
- State Key Laboratory of Food Science and Technology, China-Canada Joint Lab of Food Science and Technology (Nanchang), Nanchang University, 235 Nanjing East Road, Nanchang 330047, China.
| | - Yi Chen
- State Key Laboratory of Food Science and Technology, China-Canada Joint Lab of Food Science and Technology (Nanchang), Nanchang University, 235 Nanjing East Road, Nanchang 330047, China
| | - Shaoping Nie
- State Key Laboratory of Food Science and Technology, China-Canada Joint Lab of Food Science and Technology (Nanchang), Nanchang University, 235 Nanjing East Road, Nanchang 330047, China
| | - Maomao Zeng
- State Key Laboratory of Food Science and Technology, Jiangnan University, Wuxi 214122, China
| | - Jie Chen
- State Key Laboratory of Food Science and Technology, Jiangnan University, Wuxi 214122, China
| | - Mingyong Xie
- State Key Laboratory of Food Science and Technology, China-Canada Joint Lab of Food Science and Technology (Nanchang), Nanchang University, 235 Nanjing East Road, Nanchang 330047, China.
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Dong L, Qiu C, Wei F, Yu Z, Zhang Y, Wang S. The Effect of Microwave Baking Conditions on the Quality of Biscuits and the Control of Thermal Processing Hazards in the Maillard Reaction. Front Nutr 2022; 9:825365. [PMID: 35284448 PMCID: PMC8914164 DOI: 10.3389/fnut.2022.825365] [Citation(s) in RCA: 12] [Impact Index Per Article: 4.0] [Reference Citation Analysis] [Abstract] [Grants] [Track Full Text] [Download PDF] [Figures] [Journal Information] [Subscribe] [Scholar Register] [Received: 11/30/2021] [Accepted: 01/27/2022] [Indexed: 11/13/2022] Open
Abstract
To reduce thermal processing hazards (TPHs), microwave baking has been extensively used in food thermal processing. In this study, the influence of microwave power and microwave time on the formation of TPHs and their precursors was explored in microwave-baked biscuits. The results indicated that the content of acrylamide, 5-hydroxymethylfurfural, methylglyoxal, and 3-deoxyglucosone increased linearly with the extension of microwave time (2, 2.5, and 3 min) and microwave power (440, 480, and 520 W). There was a significant correlation between the four TPHs. 3-Deoxyglucosone may directly or indirectly participate in the formation of the other three TPHs. The relationship between TPH levels with some heat-induced sensory characteristics was analyzed. The correlation between the sensory characteristics and the content of TPHs is L* > a* > hardness > Water activity (AW). The correlation coefficients between L* value and the four TPHs are −0.950, −0.891, −0.803, and −0.985. Furthermore, the content of TPHs produced by traditional baking and microwave baking under the same texture level was compared. Compared with traditional baking (190°C, 7 min), microwave baking at 440 W for 3 min successfully decrease methylglyoxal, 3-Deoxyglucosone, acrylamide, and 5-hydroxymethylfurfural content by 60.75, 30.19, 30.87, and 61.28%, respectively. Traditionally baked biscuits, which had a more obvious color, as characterized by lower L* value, larger a* and b* values, are more susceptible to the formation of TPHs. Therefore, microwave baking can reduce the generation of TPHs.
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38
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Natural Antioxidants and Hydrocolloids as a Mitigation Strategy to Inhibit Advanced Glycation End Products (AGEs) and 5-Hydroxymethylfurfural (HMF) in Butter Cookies. Foods 2022; 11:foods11050657. [PMID: 35267290 PMCID: PMC8909267 DOI: 10.3390/foods11050657] [Citation(s) in RCA: 4] [Impact Index Per Article: 1.3] [Reference Citation Analysis] [Abstract] [Key Words] [Track Full Text] [Download PDF] [Figures] [Journal Information] [Subscribe] [Scholar Register] [Received: 01/05/2022] [Revised: 02/17/2022] [Accepted: 02/21/2022] [Indexed: 11/24/2022] Open
Abstract
Maillard reaction during food processing contributes to the formation of some unpleasant heat-induced toxicants including advanced glycation end products (AGEs) and 5-hydroxymethylfurfural (HMF). The current study prepared butter cookies fortified with two dietary natural antioxidants (catechins and curcumin) and two dietary hydrocolloids (pectin and chitosan), and investigated their effects on formation of free Nε-(carboxymethyl)lysine (CML)/Nε-(carboxyethyl)lysine (CEL), protein-bound CML/CEL and HMF and on the sensory qualities of butter cookies. Meanwhile, three typical α-dicarbonyl compounds were also determined to identify possible correlations between α-dicarbonyl intermediates and formation of these harmful heat-induced products in butter cookies. Experimental data showed that catechin exhibited the strongest inhibitory effects on formation of AGEs and HMF, but its addition would impair the color and taste of cookies. On the other hand, chitosan was not so effective in inhibiting AGEs and HMF as compared to catechin, but its addition could increase the sensory qualities of butter cookies.
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Simultaneous Determination of Seven α-Dicarbonyl Compounds in Milk and Milk Products Based on an LC–MS/MS Method with Matrix-Matched Calibration. FOOD ANAL METHOD 2022. [DOI: 10.1007/s12161-021-02219-6] [Citation(s) in RCA: 2] [Impact Index Per Article: 0.7] [Reference Citation Analysis] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 11/04/2022]
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40
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Hernandez-Castillo C, Shuck SC. Diet and Obesity-Induced Methylglyoxal Production and Links to Metabolic Disease. Chem Res Toxicol 2021; 34:2424-2440. [PMID: 34851609 DOI: 10.1021/acs.chemrestox.1c00221] [Citation(s) in RCA: 11] [Impact Index Per Article: 2.8] [Reference Citation Analysis] [Abstract] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 01/17/2023]
Abstract
The obesity rate in the United States is 42.4% and has become a national epidemic. Obesity is a complex condition that is influenced by socioeconomic status, ethnicity, genetics, age, and diet. Increased consumption of a Western diet, one that is high in processed foods, red meat, and sugar content, is associated with elevated obesity rates. Factors that increase obesity risk, such as socioeconomic status, also increase consumption of a Western diet because of a limited access to healthier options and greater affordability of processed foods. Obesity is a public health threat because it increases the risk of several pathologies, including atherosclerosis, diabetes, and cancer. The molecular mechanisms linking obesity to disease onset and progression are not well understood, but a proposed mechanism is physiological changes caused by altered lipid peroxidation, glycolysis, and protein metabolism. These metabolic pathways give rise to reactive molecules such as the abundant electrophile methylglyoxal (MG), which covalently modifies nucleic acids and proteins. MG-adducts are associated with obesity-linked pathologies and may have potential for biomonitoring to determine the risk of disease onset and progression. MG-adducts may also play a role in disease progression because they are mutagenic and directly impact protein stability and function. In this review, we discuss how obesity drives metabolic alterations, how these alterations lead to MG production, the association of MG-adducts with disease, and the potential impact of MG-adducts on cellular function.
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Affiliation(s)
- Carlos Hernandez-Castillo
- Department of Diabetes and Cancer Metabolism, Beckman Research Institute of City of Hope, Duarte, California 91010, United States
| | - Sarah C Shuck
- Department of Diabetes and Cancer Metabolism, Beckman Research Institute of City of Hope, Duarte, California 91010, United States
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41
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Analysis of α-dicarbonyl compounds and 4-methylimidazole in coffee made with various roasting and brewing conditions. Lebensm Wiss Technol 2021. [DOI: 10.1016/j.lwt.2021.112231] [Citation(s) in RCA: 8] [Impact Index Per Article: 2.0] [Reference Citation Analysis] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 11/21/2022]
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42
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Cincotta F, Brighina S, Condurso C, Arena E, Verzera A, Fallico B. Sugars Replacement as a Strategy to Control the Formation of α-Dicarbonyl and Furanic Compounds during Cookie Processing. Foods 2021; 10:2101. [PMID: 34574211 PMCID: PMC8466310 DOI: 10.3390/foods10092101] [Citation(s) in RCA: 4] [Impact Index Per Article: 1.0] [Reference Citation Analysis] [Abstract] [Key Words] [Track Full Text] [Download PDF] [Figures] [Journal Information] [Subscribe] [Scholar Register] [Received: 07/26/2021] [Revised: 08/28/2021] [Accepted: 08/31/2021] [Indexed: 01/29/2023] Open
Abstract
In the last decade, several preventive strategies were considered to mitigate the chemical hazard accumulation in food products. This work aimed to study the effect of different sugars on the development of the main chemical hazard in cookies. For this purpose, model biscuits prepared using sucrose, fructose, and glucose were baked at different temperatures (150, 170, and 190 °C) and for different times (from 5 to 45 min), and the levels of α-dicarbonyl compounds, such as 3-deoxyglucosone (3-DG), glyoxal (GO) and methylglyoxal (MGO), 5-hydroxymethylfurfural (HMF), and furanic aromatic compounds were monitored. The replacement of sucrose in the cookie recipes with monosaccharides had as a consequence the highest accumulation of 3-DG (200-600 times higher), MGO, HMF, and furanic volatile compounds, while the use of sucrose allowed for maintaining the 3-DG, MGO, and HMF levels at less than 10 mg/kg dry matter in cookies for the estimated optimal baking time. Moreover, cookies with sucrose were characterised in terms of volatile compounds, mainly in terms of lipid oxidation products, while cookies with fructose or glucose baked at the highest temperature were characterised almost exclusively by Maillard reaction products, confirming a faster development of this reaction during baking at the studied temperatures.
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Affiliation(s)
- Fabrizio Cincotta
- Department of Veterinary Sciences, University of Messina, Polo Universitario dell’Annunziata, 98168 Messina, Italy; (F.C.); (C.C.); (A.V.)
| | - Selina Brighina
- Dipartimento di Agricoltura, Alimentazione, Ambiente (Di3A), University of Catania, Via Santa Sofia 98, 95123 Catania, Italy; (S.B.); (B.F.)
| | - Concetta Condurso
- Department of Veterinary Sciences, University of Messina, Polo Universitario dell’Annunziata, 98168 Messina, Italy; (F.C.); (C.C.); (A.V.)
| | - Elena Arena
- Dipartimento di Agricoltura, Alimentazione, Ambiente (Di3A), University of Catania, Via Santa Sofia 98, 95123 Catania, Italy; (S.B.); (B.F.)
| | - Antonella Verzera
- Department of Veterinary Sciences, University of Messina, Polo Universitario dell’Annunziata, 98168 Messina, Italy; (F.C.); (C.C.); (A.V.)
| | - Biagio Fallico
- Dipartimento di Agricoltura, Alimentazione, Ambiente (Di3A), University of Catania, Via Santa Sofia 98, 95123 Catania, Italy; (S.B.); (B.F.)
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Lu Y, Lu M, Wang J, Jiang X, Lu Y, Qiu C, Lv L, Dong W. Inhibitory Activity on the Formation of Reactive Carbonyl Species in Edible Oil by Synthetic Polyphenol Antioxidants. JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY 2021; 69:9025-9033. [PMID: 33459012 DOI: 10.1021/acs.jafc.0c07248] [Citation(s) in RCA: 7] [Impact Index Per Article: 1.8] [Reference Citation Analysis] [Abstract] [Key Words] [MESH Headings] [Track Full Text] [Subscribe] [Scholar Register] [Indexed: 06/12/2023]
Abstract
Food lipids play an important role in food quality, and their attributes contribute to texture, flavor, and nutrition. However, high-temperature processing leads to lipid peroxidation, degradation, and the formation of reactive carbonyl species (RCS), such as acrolein (ACR), glyoxal (GO), and methylglyoxal (MGO). We investigated the changes in the peroxidation value (POV), Rancimat induction time, formation and total amount of RCS, and inhibitory effects of synthetic polyphenol antioxidants on ACR/GO/MGO in plant oils during heating processing through an accelerated oxidation test using Rancimat. With increasing temperature and heating time, the amounts of ACR, GO, and MGO in oil increased and the level of ACR was about several times higher than that of GO and MGO. We also found that some amounts of ACR, GO, and MGO were produced at the initial stage before reaching the peak value of POV, even before oil oxidative rancidity, and the common antioxidant butyl hydroxyanisole (BHA)/butylated hydroxytoluene (BHT) could not remove them once they were generated. This is first time to purify PG-ACR-MGO and elucidate the structure based on analysis of their high resolution mass spectrometry and 1H, 13C, and two-dimensional nuclear magnetic resonance. We further found that PG rather than BHT and BHA efficiently trapped ACR, OG, and MGO to form adducts in oil and roasted beef burgers with corn oil. Additionally, after incubation at 80 °C, the trapping order of PG was as follows: ACR, MGO, and GO, and the adduct of PG-ACR was formed within 1 min; after 10 min, PG-MGO was generated; and three adducts formed at 15 min. However, PG could not trap ACR, GO, or MGO to form adducts at room temperature. This study provided novel knowledge to advance our understanding of the ability of synthetic polyphenol antioxidants to scavenge RCS simultaneously, such as ACR, MGO, and GO. Our findings demonstrated that PG, as an inhibitor of RCS, is suitable for medium- and high-temperature food processing but not for normal-temperature storage.
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Affiliation(s)
- Yongling Lu
- Department of Food Science and Technology, School of Food Science and Pharmaceutical Engineering, Nanjing Normal University, 2 Xuelin Road, Nanjing, Jiangsu 210023, People's Republic of China
| | - Min Lu
- Department of Food Science and Technology, School of Food Science and Pharmaceutical Engineering, Nanjing Normal University, 2 Xuelin Road, Nanjing, Jiangsu 210023, People's Republic of China
| | - Jiaqi Wang
- Department of Food Science and Technology, School of Food Science and Pharmaceutical Engineering, Nanjing Normal University, 2 Xuelin Road, Nanjing, Jiangsu 210023, People's Republic of China
| | - Xiaoyun Jiang
- Department of Food Science and Technology, School of Food Science and Pharmaceutical Engineering, Nanjing Normal University, 2 Xuelin Road, Nanjing, Jiangsu 210023, People's Republic of China
| | - Yang Lu
- Department of Food Science and Technology, School of Food Science and Pharmaceutical Engineering, Nanjing Normal University, 2 Xuelin Road, Nanjing, Jiangsu 210023, People's Republic of China
| | - Caiyi Qiu
- Department of Food Science and Technology, School of Food Science and Pharmaceutical Engineering, Nanjing Normal University, 2 Xuelin Road, Nanjing, Jiangsu 210023, People's Republic of China
| | - Lishuang Lv
- Department of Food Science and Technology, School of Food Science and Pharmaceutical Engineering, Nanjing Normal University, 2 Xuelin Road, Nanjing, Jiangsu 210023, People's Republic of China
| | - Wenjiang Dong
- Spice and Beverage Research Institute, Chinese Academy of Tropical Agricultural Sciences, Wanning, Hainan 571533, People's Republic of China
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Jana A, Baruah M, Munan S, Samanta A. ICT based water-soluble fluorescent probe for discriminating mono and dicarbonyl species and analysis in foods. Chem Commun (Camb) 2021; 57:6380-6383. [PMID: 34081065 DOI: 10.1039/d1cc02600c] [Citation(s) in RCA: 30] [Impact Index Per Article: 7.5] [Reference Citation Analysis] [Abstract] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 11/21/2022]
Abstract
A unique and highly water-soluble ICT-based fluorescent probe is developed for efficient detection and discrimination of reactive monocarbonyl formaldehyde (FA) from dicarbonyl methylglyoxal (MGO)/glyoxal (GO) by modulating the ICT process, which was confirmed by photophysical and TD-DFT analysis. The probe is applied in cellular imaging and quantifying FA in preserved food and MGO in manuka honey.
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Affiliation(s)
- Anal Jana
- Molecular Sensors and Therapeutics Research Laboratory, Department of Chemistry, School of Natural Sciences, Shiv Nadar University, NH 91, Tehsil Dadri, Gautam Buddha Nagar, Uttar Pradesh 201314, India.
| | - Mousumi Baruah
- Molecular Sensors and Therapeutics Research Laboratory, Department of Chemistry, School of Natural Sciences, Shiv Nadar University, NH 91, Tehsil Dadri, Gautam Buddha Nagar, Uttar Pradesh 201314, India.
| | - Subrata Munan
- Molecular Sensors and Therapeutics Research Laboratory, Department of Chemistry, School of Natural Sciences, Shiv Nadar University, NH 91, Tehsil Dadri, Gautam Buddha Nagar, Uttar Pradesh 201314, India.
| | - Animesh Samanta
- Molecular Sensors and Therapeutics Research Laboratory, Department of Chemistry, School of Natural Sciences, Shiv Nadar University, NH 91, Tehsil Dadri, Gautam Buddha Nagar, Uttar Pradesh 201314, India.
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45
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Feng T, Zhou Y, Wang X, Wang X, Xia S. α-Dicarbonyl compounds related to antimicrobial and antioxidant activity of maillard reaction products derived from xylose, cysteine and corn peptide hydrolysate. FOOD BIOSCI 2021. [DOI: 10.1016/j.fbio.2021.100951] [Citation(s) in RCA: 7] [Impact Index Per Article: 1.8] [Reference Citation Analysis] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 11/16/2022]
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46
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Aglago EK, Schalkwijk CG, Freisling H, Fedirko V, Hughes DJ, Jiao L, Dahm CC, Olsen A, Tjønneland A, Katzke V, Johnson T, Schulze MB, Aleksandrova K, Masala G, Sieri S, Simeon V, Tumino R, Macciotta A, Bueno-de-Mesquita B, Skeie G, Gram IT, Sandanger T, Jakszyn P, Sánchez MJ, Amiano P, Colorado-Yohar SM, Gurrea AB, Perez-Cornago A, Mayén AL, Weiderpass E, Gunter MJ, Heath AK, Jenab M. Plasma concentrations of advanced glycation end-products and colorectal cancer risk in the EPIC study. Carcinogenesis 2021; 42:705-713. [PMID: 33780524 PMCID: PMC8162627 DOI: 10.1093/carcin/bgab026] [Citation(s) in RCA: 10] [Impact Index Per Article: 2.5] [Reference Citation Analysis] [Abstract] [MESH Headings] [Grants] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Received: 12/16/2020] [Revised: 03/02/2021] [Accepted: 03/25/2021] [Indexed: 02/07/2023] Open
Abstract
Advanced glycation end-products (AGEs) are a heterogeneous group of compounds formed by the non-enzymatic reaction between amino acids and reducing sugars, or dicarbonyls as intermediate compounds. Experimental studies suggest that AGEs may promote colorectal cancer, but prospective epidemiologic studies are inconclusive. We conducted a case-control study nested within a large European cohort. Plasma concentrations of three protein-bound AGEs-Nε-(carboxy-methyl)lysine (CML), Nε-(carboxy-ethyl)lysine (CEL) and Nδ-(5-hydro-5-methyl-4-imidazolon-2-yl)-ornithine (MG-H1)-were measured by ultra-performance liquid chromatography-tandem mass spectrometry in baseline samples collected from 1378 incident primary colorectal cancer cases and 1378 matched controls. Multivariable-adjusted odds ratios (ORs) and 95% confidence intervals (CIs) were computed using conditional logistic regression for colorectal cancer risk associated with CML, CEL, MG-H1, total AGEs, and [CEL+MG-H1: CML] and [CEL:MG-H1] ratios. Inverse colorectal cancer risk associations were observed for CML (OR comparing highest to lowest quintile, ORQ5 versus Q1 = 0.40, 95% CI: 0.27-0.59), MG-H1 (ORQ5 versus Q1 = 0.73, 95% CI: 0.53-1.00) and total AGEs (OR Q5 versus Q1 = 0.52, 95% CI: 0.37-0.73), whereas no association was observed for CEL. A higher [CEL+MG-H1: CML] ratio was associated with colorectal cancer risk (ORQ5 versus Q1 = 1.91, 95% CI: 1.31-2.79). The associations observed did not differ by sex, or by tumour anatomical sub-site. Although individual AGEs concentrations appear to be inversely associated with colorectal cancer risk, a higher ratio of methylglyoxal-derived AGEs versus those derived from glyoxal (calculated by [CEL+MG-H1: CML] ratio) showed a strong positive risk association. Further insight on the metabolism of AGEs and their dicarbonyls precursors, and their roles in colorectal cancer development is needed.
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Affiliation(s)
- Elom K Aglago
- Nutrition and Metabolism Section, International Agency for Research on Cancer, Lyon, France
| | - Casper G Schalkwijk
- Department of Internal Medicine, CARIM School for Cardiovascular Diseases, Maastricht University Medical Center, Maastricht, The Netherlands
| | - Heinz Freisling
- Nutrition and Metabolism Section, International Agency for Research on Cancer, Lyon, France
| | - Veronika Fedirko
- Department of Epidemiology, Rollins School of Public Health, Emory University, Atlanta, GA, USA
| | - David J Hughes
- Cancer Biology and Therapeutics Group (CBT), Conway Institute, School of Biomolecular and Biomedical Science (SBBS), University College Dublin, Dublin, Ireland
| | - Li Jiao
- Department of Medicine, Baylor College of Medicine, Houston, TX, USA
| | | | - Anja Olsen
- Department of Public Health, Aarhus University, Aarhus, Denmark
- Danish Cancer Society Research Center, København, Denmark
| | - Anne Tjønneland
- Danish Cancer Society Research Center, København, Denmark
- Department of Public Health, University of Copenhagen, Copenhagen, Denmark
| | - Verena Katzke
- Division of Cancer Epidemiology, German Cancer Research Center (DKFZ), Heidelberg, Germany
| | - Theron Johnson
- Division of Cancer Epidemiology, German Cancer Research Center (DKFZ), Heidelberg, Germany
| | - Matthias B Schulze
- Department of Molecular Epidemiology, German Institute of Human Nutrition Potsdam-Rehbruecke, Nuthetal, Germany
- Institute of Nutrition Science, University of Potsdam, Nuthetal, Germany
| | - Krasimira Aleksandrova
- Institute of Nutrition Science, University of Potsdam, Nuthetal, Germany
- Nutrition, Immunity and Metabolism Senior Scientist Group, Department of Nutrition and Gerontology, German Institute of Human Nutrition Potsdam-Rehbruecke (DIfE), Nuthetal, Germany
| | - Giovanna Masala
- Cancer Risk Factors and Life-Style Epidemiology Unit, Institute for Cancer Research, Prevention and Clinical Network-ISPRO, Florence, Italy
| | - Sabina Sieri
- Epidemiology and Prevention Unit, Fondazione IRCCS Istituto Nazionale dei Tumori di Milano, Milano, Italy
| | - Vittorio Simeon
- Dipartimento di Salute Mentale e Fisica e Medicina Preventiva, University ‘Luigi Vanvitelli’, Napoli, Italy
| | - Rosario Tumino
- Cancer Registry and Histopathology Department, Provincial Health Authority (ASP 7), Ragusa, Italy
| | - Alessandra Macciotta
- Department of Clinical and Biological Sciences, University of Turin, Torino, Italy
| | - Bas Bueno-de-Mesquita
- Department for Determinants of Chronic Diseases (DCD), National Institute for Public Health and the Environment (RIVM), PO Box 1, 3720 BA Bilthoven, The Netherlands
| | - Guri Skeie
- Faculty of Health Sciences, Department of Community Medicine, University of Tromsø, The Arctic University of Norway, Tromsø, Norway
| | - Inger Torhild Gram
- Faculty of Health Sciences, Department of Community Medicine, University of Tromsø, The Arctic University of Norway, Tromsø, Norway
| | - Torkjel Sandanger
- Faculty of Health Sciences, Department of Community Medicine, University of Tromsø, The Arctic University of Norway, Tromsø, Norway
| | - Paula Jakszyn
- Unit of Nutrition and Cancer, Cancer Epidemiology Research Programme, Catalan Institute of Oncology, Barcelona, Spain
- Blanquerna School of Health Sciences, Ramon Llull University, Barcelona, Spain
| | - Maria-Jose Sánchez
- Escuela Andaluza de Salud Pública (EASP), Granada, Spain
- Instituto de Investigación Biosanitaria ibs.Granada, Granada, Spain
- Department of Preventive Medicine and Public Health, University of Granada, Granada, Spain
- Centro de Investigación Biomédica en Red de Epidemiología y Salud Pública (CIBERESP), Madrid, Spain
| | - Pilar Amiano
- Centro de Investigación Biomédica en Red de Epidemiología y Salud Pública (CIBERESP), Madrid, Spain
- Public Health Division of Gipuzkoa, BioDonostia Research Institute, Donostia-San Sebastian, Spain
| | - Sandra M Colorado-Yohar
- Centro de Investigación Biomédica en Red de Epidemiología y Salud Pública (CIBERESP), Madrid, Spain
- Department of Epidemiology, Murcia Regional Health Council, IMIB-Arrixaca, Murcia, Spain
- Research Group on Demography and Health, National Faculty of Public Health, University of Antioquia, Medellín, Colombia
| | - Aurelio Barricarte Gurrea
- Centro de Investigación Biomédica en Red de Epidemiología y Salud Pública (CIBERESP), Madrid, Spain
- Navarra Public Health Institute, Pamplona, Spain
- Navarra Institute for Health Research (IdiSNA), Pamplona, Spain
| | - Aurora Perez-Cornago
- Cancer Epidemiology Unit, Nuffield Department of Population Health, University of Oxford, Oxford, UK
| | - Ana-Lucia Mayén
- Nutrition and Metabolism Section, International Agency for Research on Cancer, Lyon, France
| | - Elisabete Weiderpass
- Office of the Director, International Agency for Research on Cancer (IARC), Lyon, France
| | - Marc J Gunter
- Nutrition and Metabolism Section, International Agency for Research on Cancer, Lyon, France
| | - Alicia K Heath
- Department of Epidemiology and Biostatistics, School of Public Health, Imperial College London, London, UK
| | - Mazda Jenab
- Nutrition and Metabolism Section, International Agency for Research on Cancer, Lyon, France
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47
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Liu D, He Y, Xiao J, Zhou Q, Wang M. The occurrence and stability of Maillard reaction products in various traditional Chinese sauces. Food Chem 2021; 342:128319. [PMID: 33067040 DOI: 10.1016/j.foodchem.2020.128319] [Citation(s) in RCA: 19] [Impact Index Per Article: 4.8] [Reference Citation Analysis] [Abstract] [Key Words] [MESH Headings] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Received: 01/16/2020] [Revised: 08/18/2020] [Accepted: 10/04/2020] [Indexed: 02/08/2023]
Abstract
Traditional Chinese sauces, especially soy sauce, vinegar, and oyster sauce, provide foods with special color, flavor, and taste. However, during their manufacturing process, Maillard reaction products (MRPs) might be formed and cause adverse effects on human health. This study detected the levels of some typical MRPs in these sauces. Results showed that dark soy sauce and some vinegar products were high in 5-hydroxymethylfurfural (HMF). Moreover, dark soy sauce was significantly higher in 5-methylfurfural (MF) and methylglyoxal (MGO) than oyster sauce but lower in glyoxal (GO) than vinegar and oyster sauce, while light soy sauce had significantly higher advanced glycation end products (AGEs) than the rest three types of sauces. Besides, storage stability results indicated that MRPs increased obviously in vinegar and dark soy sauce. Finally, concentration limits/regulations of MRPs in traditional Chinese sauces should be established in the future considering their high frequency of usage and high potential of insalubrity.
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Affiliation(s)
- Dongcheng Liu
- School of Biological Sciences, The University of Hong Kong, Hong Kong, PR China
| | - Yulu He
- School of Biological Sciences, The University of Hong Kong, Hong Kong, PR China
| | - Jianbo Xiao
- Institute of Food Safety and Nutrition, Jiangsu University, Zhenjiang, PR China
| | - Qian Zhou
- School of Biological Sciences, The University of Hong Kong, Hong Kong, PR China.
| | - Mingfu Wang
- School of Biological Sciences, The University of Hong Kong, Hong Kong, PR China.
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Zamora R, Hidalgo FJ. Formation of naphthoquinones and anthraquinones by carbonyl-hydroquinone/benzoquinone reactions: A potential route for the origin of 9,10-anthraquinone in tea. Food Chem 2021; 354:129530. [PMID: 33761338 DOI: 10.1016/j.foodchem.2021.129530] [Citation(s) in RCA: 4] [Impact Index Per Article: 1.0] [Reference Citation Analysis] [Abstract] [Key Words] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Received: 01/07/2021] [Revised: 02/26/2021] [Accepted: 03/02/2021] [Indexed: 11/15/2022]
Abstract
The reaction of 2-alkenals (crotonaldehyde and 2-pentenal) with hydroquinones (hydroquinone and tert-butylhydroquinone) and benzoquinones (benzoquinone, methylbenzoquinone, and methoxybenzoquinone) was studied as a potential route for the endogenous formation of naphthoquinones and anthraquinones in foods. Polycyclic quinones were produced at a low water activity, within a wide pH range, and in the presence of air. 9,10-Anthraquinone formation had an activation energy of 46.1 ± 0.1 kJ·mol-1, and a reaction pathway for the formation of the different naphthoquinones and anthraquinones is proposed. These reactions also took place in tea, therefore suggesting that the common tea pollutant 9,10-anthraquinone is also a process-induced contaminant. In fact, when four commercial teas (from a total of eight studied teas) were heated at 60 °C for 72 h, they significantly (p < 0.05) increased the amount of this toxicant. Reduction of 9,10-anthraquinone formation in teas is suggested to be carried out by reducing/scavenging its precursors.
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Affiliation(s)
- Rosario Zamora
- Instituto de la Grasa, Consejo Superior de Investigaciones Científicas, Carretera de Utrera km 1, Campus Universitario - Edificio 46, 41013 Seville, Spain
| | - Francisco J Hidalgo
- Instituto de la Grasa, Consejo Superior de Investigaciones Científicas, Carretera de Utrera km 1, Campus Universitario - Edificio 46, 41013 Seville, Spain.
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49
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Zhao S, Hu H, Xie J, Shen M. Investigation into the contents of nutrients, Nε-carboxymethyllysine and Nε-carboxyethyllysine in various commercially canned fishes to find the correlation between them. J Food Compost Anal 2021. [DOI: 10.1016/j.jfca.2020.103737] [Citation(s) in RCA: 0] [Impact Index Per Article: 0] [Reference Citation Analysis] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Indexed: 10/22/2022]
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50
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Detection of acacia honey adulteration with high fructose corn syrup through determination of targeted α‑Dicarbonyl compound using ion mobility-mass spectrometry coupled with UHPLC-MS/MS. Food Chem 2021; 352:129312. [PMID: 33652193 DOI: 10.1016/j.foodchem.2021.129312] [Citation(s) in RCA: 13] [Impact Index Per Article: 3.3] [Reference Citation Analysis] [Abstract] [Key Words] [Track Full Text] [Journal Information] [Subscribe] [Scholar Register] [Received: 09/23/2020] [Revised: 12/16/2020] [Accepted: 01/02/2021] [Indexed: 12/27/2022]
Abstract
High-value acacia honey is often adulterated with inexpensive high fructose corn syrup (HFCS), due to their similar color and sugar composition. α‑Dicarbonyl compounds formed by Maillard reaction or caramelization during heat treatment or storage, differ between HFCS and honey due to differences in starting materials and processing methods. In this study, we compared α-dicarbonyl compounds in acacia honey and HFCS by Ion Mobility-Mass Spectrometry and multivariate statistical analysis. Through α-dicarbonyl compound derivatization with o-phenylenediamine, we screened a marker with 189.1023 m/z and 139.3 Å2 Collision Cross-Section that can distinguish HFCS from acacia honey. Nuclear magnetic resonance spectra identified this marker compound as 3,4-dideoxypentosulose. We then used chromatography-coupled tandem mass spectrometry to quantitate 3,4-dideoxypentosulose in market samples of honey and HFCS and found that 3,4-dideoxypentosulose was negligible (<0.098 mg/kg) in honey, but prevalent in HFCS (≧1.174 mg/kg), indicating 3,4-dideoxypentosulose can serve as an alternative indicator of HFCS adulteration of acacia honey.
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