FOOD CHEMISTRY
·
2025
·
IF 9.8
Tong Zhou,Qingqing Chai,Man Zhang,Heping Cui,Ahmad Mohammad,Khizar Hayat,Xiaoming Zhang,Chi-Tang Ho
Exogenous xylose (Xyl) could promote 2-furfural formation but inhibit pyrazines generation during its co-heating with alanine (Ala)-Xyl Amadori rearrangement product (AX-ARP). The activation energy of AX-ARP formation from Ala and Xyl was considerably lower than that of pyrazine formation from Ala and glyoxal (GO). Accordingly, the preferential interaction of exogenous Xyl with regenerated Ala triggered a continuous cycle of consumption and regeneration of Ala in AX-ARP-Xyl model. In this way, functioning as a catalyst, regenerated Ala facilitated the continuous conversion of AX-ARP into deoxyxylosones (DXs). However, exogenous Xyl accelerated the pH drop during the thermal treatment of AX-ARP, which favored the conversion of DXs into 2-furfural while limiting the transformation of their α-dicarbonyl fragments into pyrazines. Model reactions of AX-ARP-[ 13 C 5 -Xyl] further confirmed that exogenous Xyl was progressively converted into 2-furfural, while its downstream products, such as GO and methylglyoxal (MGO), did not exhibit an enhanced tendency to form pyrazines.
研究领域:
食品科学
·
生物化学
✓ 已验证
产品关联
DOI
PubMed
高影响因子
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY
·
2024
·
IF 5.7
Tong Zhou,Meigui Huang,Heping Cui,Pusen Chen,Khizar Hayat,Xiaoming Zhang,Chi-Tang Ho
The involvement of exogenous alanine was observed to inhibit the generation of 2-furfural during the thermal degradation of the Amadori rearrangement product (ARP). To clarify the reason for the reduced yield of 2-furfural triggered by exogenous alanine, the evolution of the precursors of 2-furfural formed in the ARP model and ARP-alanine model was investigated, and a model including ARP and 15N-labeled alanine was used to differentiate the role of endogenous and exogenous alanine in the degradation of ARP. It was found that the condensation between ARP and 3-deoxyxylosone could occur during thermal treatment. Nevertheless, the interaction of ARP with 3-deoxyxylosone exhibited an accelerated pace in the presence of exogenous alanine. In this way, exogenous alanine blocked the recovery of endogenous alanine while simultaneously enhancing the consumption of ARP and 3-deoxyxylosone during the Maillard reaction. Hence, the yield of 2-furfural was diminished with the interference of exogenous alanine. Furthermore, the promotion of the reaction between ARP and deoxyxylosone induced by exogenous alanine blocked their retro-aldolization reaction to short-chain α-dicarbonyls (α-DCs) and consequently resulted in a lack of pyrazine formation during the ARP degradation. The present study provided a feasible method for the controlled formation of 2-furfural during the thermal treatment of ARP derived from alanine.
研究领域:
食品科学
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生物化学
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DOI
PubMed
高影响因子
Molecular Catalysis
·
2025
·
IF 4.9
Wanqing Sun,Jilei Xu,Lei Li,Zhu Liu,Zuoyi Xiao,Qingda An,Jiahui Huang
5,5′(oxy-bis(methylene)) bis-2-furfural (OBMF) is an important biobased chemical that can be synthesized through the self-etherification of 5-hydroxymethylfurfural (HMF) in the presence of either homogeneous acid or solid acid catalysts, such as p-toluenesulfonic acid (PTSA) and molecular sieves. In previous studies, all authors believed that this process follows an acid-catalyzed mechanism, even though some argued that acid strength is not the key factor in the formation of OBMF. In this work, we present a new route for the synthesis of OBMF from HMF, utilizing hydrogen-bonding catalysis with protonated ionic liquids under metal-free conditions. [NMPH][OTf] featuring a cationic hydrogen bond donor and an anionic hydrogen bond acceptor, is effective for the self-etherification of HMF. Under the optimal conditions, the yield of OBMF reached approximately 92.4 %. Based on the results of Attenuated Total Reflectance Infrared Spectroscopy (ATR-IR), Nuclear Magnetic Resonance (NMR) and Density Functional Theory (DFT) calculation, it is determined that the cations and anions of ILs could activate the C O and O H bonds of HMF via hydrogen bonds respectively. This synergistically facilitates the self-etherification of two HMF molecules to form OBMF. After recycling the catalyst four times, the yield of OBMF did not decrease significantly. According to the Arrhenius law, the apparent activation energy and reaction order for [NMPH][OTf] in the self-etherification of HMF to OBMF are determined 40.7 kJ/mol and 1.0, respectively. The results suggested that [NMPH][OTf] is an excellent catalyst for the generation of OBMF from HMF. Therefore, this study offers a simple and environmentally friendly method for the production of OBMF, which holds promising potential for broad application prospect in the future.
研究领域:
化学工程
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绿色化学
·
可再生资源利用
✓ 已验证
产品关联
DOI
高影响因子
FOOD RESEARCH INTERNATIONAL
·
2017
·
IF 3.086
Yinan Zhang,Xiaoning An
Ultra-performance liquid chromatography coupled with high-resolution tandem mass spectrometry (UPLC-HRMS/MS) was employed to investigate the inhibitory mechanism of quercetin against the formation of 5-(hydroxymethyl)-2-furaldehyde (HMF) in buckwheat flour bread. The HMF and HMF precursors (3,4-dideoxyglucosone-3-ene (3,4-DGE), 3-deoxyglucosone (3-DG), or fructofuranosyl cation dehydration products (FCDPs)) adducts of quercetin were detected in buckwheat flour bread, with the trapping of these compounds by quercetin to form corresponding adducts with HMF or its precursors in 1:1, 1:2, 1:3, and 1:4 ratios (where “1” refers to quercetin in all cases). The structures of these adducts were elucidated by UPLC-HRMS/MS. Carbohydrate module labeling (CAMOLA) techniques and the labelled quercetin in model reactions were utilized to further confirm the inhibitory mechanism. Effects of baking temperature and time on the HMF inhibition rate were investigated in wheat flour bread, and a maximum inhibition rate of 86.0% was obtained with the baking of wheat flour bread (with the added quercetin concentration of 1.90 mg/g) at 160 °C for 30 min.
研究领域:
食品科学
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分析化学
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产品关联
DOI
PubMed
高影响因子
MOLECULES
·
2024
·Vol. 29
·期 5
·1142
·
IF 4.2
Xin Wang,Jiatao Guo,Siqi Zang,Baodong Liu,Yuhuan Wu
Matteuccia struthiopterisis one of the most globally consumed edible ferns and widely used in folk medicine. Reports mainly focus on young fronds and the rhizome which are common edible medicinal parts. However, there are few detailed reports on other parts. Therefore, the volatile components of different parts based on HS-SPME-GC-MS were identified, and total flavonoid contents, antioxidant activities and acetylcholinesterase inhibitory activities were compared in order to reveal the difference of volatile components and potential medicinal value of different parts. The results showed that total flavonoid contents, antioxidant activities and volatile components of different parts were obviously different. The crozier exhibited the strongest antioxidant activities, but only underground parts exhibited a dose-dependent inhibition potential against AChE. Common volatile compounds were furfural and 2-furancarboxaldehyde, 5-methyl-. In addition, it was found that some volatile components from adventitious root, trophophyll, sporophyll and petiole were important ingredients in food, cosmetics, industrial manufacturing and pharmaceutical applications.
研究领域:
药理学
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植物学
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分析化学
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药用植物
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DOI
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高影响因子
JOURNAL OF THE SCIENCE OF FOOD AND AGRICULTURE
·
2018
·Vol. 99
·期 6
·3192-3202
·
IF 2.379
Zhisheng Zhou,Xing Hu,Guowen Zhang,Rui Wang,Deming Gong
BACKGROUND 5-Hydroxymethyl-2-furaldehyde (5-HMF), a by-product of the Maillard reaction, usually present in fried and baked food, may cause potential harm to the human body. Here, the interaction between 5-HMF and calf thymus DNA (ctDNA) under physiological buffer (pH 7.4) was studied using multi-spectroscopic methods combined with multivariate curve resolution–alternating least squares (MCR-ALS) chemometrics and molecular simulation techniques. RESULTS The concentration profiles and pure spectra of the three components (5-HMF, ctDNA and 5-HMF–ctDNA complex) were extracted from highly overlapping spectra using MCR-ALS analysis, which verified the formation of 5-HMF–ctDNA complex. The binding constant being of the order of 10 3 L mol −1 at four temperatures (292, 298, 304 and 310 K) indicated a weak affinity in the binding of 5-HMF to ctDNA. The binding interaction was mainly driven by hydrogen bonds and van der Waals forces. Viscosity analysis, melting assay, ionic strength effect and competitive fluorescence studies ascertained that 5-HMF bound to ctDNA through groove binding, and it tended to bind to guanine–cytosine rich region of ctDNA which was characterized using Fourier transform infrared spectra and molecular docking. Circular dichroism spectral analysis and DNA cleavage assays indicated that the ctDNA conformation was altered from B to A form and 5-HMF caused DNA damage at higher concentration. CONCLUSIONS The results suggested that 5-HMF bound to ctDNA through groove binding and caused DNA damage. This research may contribute to understand the binding mechanism of 5-HMF to ctDNA and to the assessment of the toxicological effect of 5-HMF in biological processes. © 2018 Society of Chemical Industry
研究领域:
化学
·
生物化学
·
毒理学
·
分子生物学
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PubMed
高影响因子
FOOD CHEMISTRY
·
2024
·
IF 8.5
Yishun Yao,Meigui Huang,Xiaomin Wang,Jingyang Yu,Heping Cui,Khizar Hayat,Xiaoming Zhang,Chi-Tang Ho
The characteristic aroma compounds of traditional braised pork were investigated by gas chromatography–mass spectrometry−olfactometry (GC–MS–O), odor-activity values, and aroma recombination and omission experiments. A total of 56 volatile compounds were detected by GC–MS, among which hexanal, octanal, nonanal, ( E )-2-octenal, 2,3-octanedione, 1-octen-3-ol, 2-pentylfuran, methanethiol, and dimethyl trisulfide were identified as the key aroma compounds by molecular sensory science. Partial least squares regression analysis indicated that some aroma compounds significantly contributed to fatty (hexanal, heptanal, 2-pentylfuran, nonanal, and ( E )-2-octenal), meaty (methanethiol, dimethyl disulfide, dimethyl trisulfide, and octanal), sauce-like flavor (3-hydroxy-2-butanone and 2-furfural), and sweet, caramel (2,3-octanedione, 1-octen-3-ol). Lean meat produced more aldehydes, alcohols, ketones, and sulfur-containing compounds than subcutaneous fat. The seasonings (saccharose, cooking wine, and soy sauce) facilitated the formation of ethyl L-lactate, 2-acetylfuran, 2-furfural, 5-methyl-2-furaldehyde, 2-methyl-pyrazine, and 2-acetylpyrrole. Meanwhile they reduced the content of lipid oxidation products, thereby stimulated the characteristic aroma of the Chinese traditional braised pork.
研究领域:
食品科学
·
分析化学
·
感官科学
✓ 已验证
产品关联
DOI
PubMed
高影响因子
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