FOOD CONTROL
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2025
·
IF 6.3
Yaoyao Zhang,Zhaohan Feng,Shangde Sun
The 3-monochloropropane-1, 2-diol esters (3-MCPDEs) and glycidyl esters (GEs), which are recognized as contaminants often produced during the deodorization process of refined edible oils, have garnered widespread attention and research interest in recent years due to their potential health risks to humans. Although there have been studies on the formation mechanisms of 3-MCPDEs and GEs, further clarification is still needed in the intrinsic synergistic effects of precursors. Herein, the synergistic effects of acylglycerols, including monoacylglycerols (MAGs), diacylglycerols (DAGs), and triacylglycerols (TAGs) on the formation of 3-MCPDEs and GEs were innovatively investigated through simulated deodorization experiments in model soybean oil systems. Additionally, the effects of simulated deodorization conditions, including temperatures, heating duration, chloride contents, and acylglycerol compositions on the production of 3-MCPDEs and GEs, were also investigated. The results indicated that under the simulated deodorization process and in the presence of chloride ions, the formation of 3-MCPDEs and GEs was facilitated by the synergistic interaction among MAGs, DAGs and TAGs. It is noteworthy that MAGs were more susceptible to forming 3-MCPDEs in the presence of chloride ions, whereas GEs predominantly resulted from the cyclization reaction of DAGs. Concurrently, when the MAGs content was less than 1%, or the presence of DAGs was less than 4% in the model system, the formation of both 3-MCPDEs and GEs was found to be below the EU regulatory limits, thus offering a solid theoretical basis for the control of 3-MCPDEs and GEs in refined oils.
研究领域:
食品科学
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毒理学
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DOI
高影响因子
Reaction Kinetics Mechanisms and Catalysis
·
2017
·Vol. 122
·期 2
·1031-1047
·
IF 1.264
Meng Chen,Cao Gui-Ping,Yan Yi-Zhen,Zhao En-You,Hou Lin-Yi,Shi Hua-Yi
In this work, during the synthesis and hydrolysis of cellulose acetate propionate (CAP), the research not only focused on the contents, but also the distributions of acetyl and propionyl groups in the different positions of anhydroglucose unit, i.e. C2, C3 and C6. It was investigated that cellulose propionylation was more difficult than acetylation, which required larger amounts of reagents. At the same temperature, the reaction rate constant of cellulose acetylation was much higher than that of propionylation. Furthermore, the partial degrees of propionyl substitution in CAP were 0.54, 0.54, and 0.48 for C2, C3, and C6. The contents of propionyl distributed on C2 and C3 positions were higher than that on C6 indicating that acetyl took the position of C6 preferentially. During the hydrolysis of CAP, the degrees of hydrolysis were 0.1 for acetyl and 0.3 for propionyl. Acetyl groups in the C6 position and propionyls in the C2 position were hydrolyzed much easier with the degrees of hydrolysis of 0.16 and 0.32, respectively. In addition, it has been investigated that hydroxyl groups in the C3 position exhibited the lowest reactivity during the synthesis of CAP, while acyl groups on C3 was also the hardest to be hydrolyzed.
研究领域:
材料科学
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化学工程
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高影响因子
FOOD RESEARCH INTERNATIONAL
·
2022
·
IF 7.425
Yali Li,Yi Zhang,Yibin Zhou,Yufei Zhang,Mingming Zheng
A novel and effective approach based on the two-step ethanolysis-esterification strategy was proposed for the controllable and simultaneous preparation of 1-oleoyl-2-palmitoyl-3-linoleoylglycerol (OPL), 1,3-dioleoyl-2-palmitoyl-glycerol (OPO) and 1,3-dilinoleoyl-2-palmitoyl-glycerol (LPL) with adjustable proportions. Enzymatic ethanolysis of fractionated palm stearin was carried out to yield 2-monopalmitoylglycerol (79.4 ± 0.6 %) with over 91.0 % purity at the optimal conditions. The immobilized Candida sp. lipase (CSL) on octyl-functionalized ordered mesoporous silica (OMS-C 8 ) was applied to re-esterify 2-monopalmitoylglycerol with oleic acid and linoleic acid for the simultaneous production of OPL, OPO, and LPL. The total content in the final products was 81.5 %, with 91.3 % of palmitic acid (PA) content at the sn -2 position. Besides, OPL/OPO/LPL was conveniently prepared with suitable proportions for worldwide infants by adjusting the ratio of acyl donors. This paper provides a novel and effective two-step ethanolysis-esterification strategy for the development of human milk fat substitutes (HMFS).
研究领域:
食品科学
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化学工程
·
生物技术
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DOI
PubMed
高影响因子
JOURNAL OF THE AMERICAN OIL CHEMISTS SOCIETY
·
2020
·Vol. 97
·期 6
·603-614
·
IF 1.659
Jia Luo,Zeping Wang,Shangzhi Deng,Fan Zhang,Guirong Bao,Junni Mao,Wenjing Yang
Direct glycerolysis of novel edible Sacha Inchi ( Plukenetia volubilis L.) seed oil (PvLO) into diacylglycerols (DAG) and monoacylglycerols (MAG) was studied over solid Na 2 SiO 3 with or without microwave assistance. The glycerolysis yield was calculated by qualitative and semiquantitative analyses of 1 H NMR, 13 C NMR, and FT-IR spectra. The yields of ~33% 1, 3-DAG, ~16% 1, 2-DAG, ~40% 1-MAG, and ~2.3% 2-MAG were achieved after 16 hours at 120 °C in three consecutive cycles using acetone, with an interesterification rate of 92%. The modified oil showed enhanced gelation ability at low temperatures. The yield of 1, 2-DAG can be increased by adding acetone as solvent. The fatty acid compositions and unsaturated structure of lipids were less destroyed after alkaline glycerolysis. However, more α-linolenic and linoleic acids were transferred to the sn -2 position of glyceryl skeleton. The oxidative stability of the modified oil was still controllable. In summary, this work provides a feasible method to convert polyunsaturated plant oils into oils rich in DAG and MAG with less destructive impact on the olefinic structure of oil. Also, it provides a useful example of how to quickly evaluate the influence of chemical modification on the chemical structure of plant oils by using various spectral technologies.
研究领域:
食品科学
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化学工程
·
植物油脂加工
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高影响因子
Current Pharmaceutical Analysis
·
2023
·Vol. 19
·期 6
·511-520
·
IF 0.6
Zhang Mengmeng,Zou Qiaogen
Background: Atopic dermatitis (AD) is an allergic skin disease that can be inherited. Crisaborole is a specific drug developed to deal with this disease. The compounds of 4-(4- Bromo-3-formyl-phenoxy)-benzonitrile and 4-(4-(4-bromo-3-formylphenoxy)-3- formylphenoxy) benzonitrile
are the representative impurities in the synthesis of Crisaborole active pharmaceutical in gradient (API). Owing to the genotoxic impurities that could lead to cancer and gene mutations, it is necessary to develop a simple, efficient, sensitive, and accurate method to detect these impurities.
In this study, the 4-(4-Bromo-3-formyl-phenoxy)-benzonitrile and 4-(4-(4- bromo-3-formylphenoxy)-3-formylphenoxy)benzo- nitrile present in Crisaborole API were detected using UPLC-MS/MS. Methods: The separation was made on a ZORBAX Eclipse XDB-Pheny column (4.6 mm ×75mm, 3.5
μm) with the mobile phase of acetonitrile solution containing 0.1% trifluoroacetic acid (A) and water containing 0.1% formic acid (B) in gradient elution mode. Quantification was performed using positive ion electrospray ionization (ESI), and the contents of two compounds were determined
using the multiple reaction monitoring (MRM) modes. Results: The quantitative analytical method was fully validated with respect to linearity (r > 0.9998), sensitivity, precision, accuracy (the average recovery of two impurities was 84.1% to 90.7%), and robustness. Conclusion:
Three batches of samples were detected by UPLC-MS/MS, indicating that the proposed approach was applicable for the quality evaluation of Crisaborole.
研究领域:
药物分析
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皮肤病学
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毒理学
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DOI
高影响因子
LWT-FOOD SCIENCE AND TECHNOLOGY
·
2020
·
IF 4.006
Xianrui Liang,Yan Jiang,Zili Guo,Sheng Fang
Trapa quadrispinosa , commonly known as water caltrop, has long been consumed as a food in Asian countries and its pericarp is discarded as waste after the fruit is harvested. In this study, a reliable method was established using UPLC-QTOF-MS/MS to identify the main compounds in Trapa quadrispinosa pericarps (TQP). The UPLC parameters including column, mobile phase, and temperature were optimized. The extraction parameters including solvents, temperatures and solid-to-liquid ratios were also optimized. A total of 35 compounds were tentatively assigned. The QTOF-MS/MS fragmentation pathways of these compounds were proposed. The most abundant compound (1,2,3,6-tetra-O-galloyl- β - d -glucose) was further purified by a semi-preparative HPLC and confirmed by 1 H- and 13 C-NMR. Hydrolyzable tannins (gallotannins and ellagitannins) consisting of almost 90% polyphenols were obtained from the TQP extracts. Three of the main hydrolyzable tannins were 1,2,3,6-tetra-O-galloyl- β - d -glucose, tri-O-galloyl-hexahydroxydiphenoyl- d -glucose, and tri-O-galloyl- d -glucose. The TQP extracts exhibited better antioxidant activity in the DPPH assay than that of the ascorbic acid standard. This study provides valuable information for the utilization of TQP as an alternative source of plant-derived antioxidants.
研究领域:
分析化学
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植物化学
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食品科学
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药理学
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DOI
高影响因子
FOOD RESEARCH INTERNATIONAL
·
2025
·
IF 8
Duan Zhou,Mouming Zhao,Xiaorong Zhong,Ning Liu,Xuefeng Chen,Daoming Li
1,3-diacylglycerol (DAG) is a natural lipid and known as functional oil. Here, we evaluated the potential of different natural deep eutectic solvents (NADESs) in synthesis of 1,3-DAG through Candida antarctica lipase B (CALB)-catalyzed esterification. Interestingly, we found that the 1,3-DAG content could be increased by 19.21 %, 13.10 %, and 8.74 % in three choline chloride (ChCl)-based NADESs, respectively, compared with that in solvent-free system. Confirmatory experiments demonstrated that NADESs could inhibit the acyl transfer of 1,3-DAG through modulating the water activity of the reaction system. Meanwhile, circular dichroism spectra and fluorescence spectroscopy results indicated that NADESs could not change the secondary structure of CALB, but could affect the tertiary conformation of CALB. Furthermore, molecular dynamics studies showed that the NADESs could induce a more compact tertiary conformation of CALB and enhance the sn -1,3 positional selectivity of CALB. Overall, the NADESs could induce a higher 1,3-DAG yield through inhibiting the acyl transfer of 1,3-DAG and enhancing the sn -1,3 positional selectivity of CALB. This study provides theoretical support for enzymatic production of structural lipids in NADESs.
研究领域:
生物化学
·
酶工程
·
食品科学
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DOI
PubMed
高影响因子
Phytochemistry Letters
·
2016
·
IF 1.353
Yangyang Xiao,Haihui Xie,Li Zhao,Ping Gou
Two new acyl flavone glucosides, luteolin-4⿲- O -(6- p -hydroxybenzoyl)-β- d -glucopyranoside (leontopodioside A, 1 ) and luteolin-4⿲- O -[6-(2-methylbutyryl)]-β- d -glucopyranoside (leontopodioside B, 2 ), and a new acyl lignan glucoside, lariciresinol-9-angeloyl-4- O -β- d -glucopyranoside (leontopodioside C, 3 ) were isolated from the whole plants of Leontopodium leontopodioides (Asteraceae). Their structures were determined by spectroscopic and chemical methods. Compounds 1 ⿿ 3 exhibited α-glucosidase inhibitory activity with the half maximal inhibitory concentration (IC 50 ) values of 55.6, 39.7, and 474.9 μM, respectively, in comparison with acarbose (626.3 μM).
研究领域:
药用植物学
·
天然产物化学
·
生物化学
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DOI
高影响因子
Journal of Oleo Science
·
2022
·
IF 1.628
Lihong He,Jiawei Zheng,Siting Feng,Li Xu,Nanjing Zhong
In this study, lipase A from Candida antarctica (CALA) was immobilized onto the macroporous resin NKA-9. Immobilization conditions (pH, time and CALA concentration) were studied, enzymatic activity and immobilization efficiency (IE) up to 968.89 U/g and 53.19% were respectively obtained under optimal conditions (immobilization pH 5.0, time 5 h and CALA concentration at 30 mg/mL). Then, the NKA-9 supported CALA (CALA@NKA-9) samples were used to catalyze glycerolysis in solvent-free system. With 0.25 g of the present CALA@NKA-9 (soybean oil 3.52 g and glycerol 0.184 g) and after 12 h reaction at 50 °C, diacylglycerols (DAG) content up to 64.37% and triacylglycerols (TAG) conversion at 83.33% were obtained. The relationship between temperature and TAG conversion was LnV 0 = 13.9310-6.4212/T for CALA@NKA-9. Meanwhile, the activation energy (Ea) of CALA@NKA-9 was calculated to be 53.39 kJ/mol. In addition, reusability in the glycerolysis reaction was also evaluated, and 57.82% of the initial glycerolysis activity was retained after 9 consecutive applications. Furthermore, the CALA@NKA-9 was also used to catalyze the esterification (esterification of fatty acids with glycerol), however, the present CALA@NKA-9 cannot initiate the esterification. Therefore, the present CALA@NKA-9 is shown to be potential for DAG production through glycerolysis reaction.
研究领域:
生物技术
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酶工程
·
化学工程
·
生物化学
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DOI
PubMed
高影响因子
PROCESS BIOCHEMISTRY
·
2023
·
IF 4.4
Meng Zhang,QingYan Li,Feiyu Fan,Fuping Lu,XueLi Zhang
This study highlights an effective strategy based on the synergistic complementarity of metabolic engineering and adaptive evolution.First, the chassis strain YL013 was obtained by deleting five acyl-CoA oxidase genes to reduce the degradation of γ-decalactone(GDL). Then, adaptive laboratory evolution with increasing concentrations of γ-decalactone was employed to obtain the strain YL013–250 with increased γ-decalactone tolerance of up to 250 mg/L. Moreover, this strain produced 664.5 mg/L γ-decalactone, representing a 142 % improvement over the parental strain YL013. Furthermore, four candidate fatty acyl-CoA synthetase genes, FAA1 , FAA2 FAA3 and FAT1, were modulated using the strong, constitutive TEFin promoter to investigate their roles in GDL production. The results showed that overexpression of FAA1 , FAA2 and FAA3 can effectively improve the ability of Yarrowia lipolytica to synthesize GDL using ricinoleic acid as substrate, among which overexpression of FAA1 had the most significant effect on GDL yield. Finally, gene of alcohol acyltransferase ( AAT1 ) from Prunus persica was introduced into Y. lipolytica , leading to a GDL titer of 2.2 g/L, which was a 1.32-fold increase compared with the parental strain without AAT1 . Taken together, this study provides a combinatorial strategy to improve GDL production through rational regulation of pathway genes and non-rational adaptive laboratory evolution.
研究领域:
代谢工程
·
微生物生物技术
·
生物过程工程
·
生物化学
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高影响因子
JOURNAL OF BIOTECHNOLOGY
·
2015
·
IF 2.871
Wei Li,Huan Wu,Benguo Liu,Xuedan Hou,Duanji Wan,Wenyong Lou,Jian Zhao
Dihydromyricetin is the principle component of the Chinese herbal tea Teng-cha and a promising ingredient for functional food and nutraceuticals, but its low solubility limits its application potentials. This study explored enzymatic acylation of dihydromyricetin to improve its solubility in lipid systems. Acylation was achieved with several lipases with the synthesis of a major (>86%) product and a minor product. Isolation and purification of the products by preparative HPLC followed by LC–MS, 13 C NMR, 1 H NMR and 2 D-HSQC NMR analyses showed that the major product was a dihydromyricetin monoester with the acylation site at the 3-OH group of C ring. Quantum chemical calculations revealed that the 3-OH had the lowest antioxidant activity , and therefore acylation at this site was expected to have minimum impact on the antioxidant activity. Several factors, including solvent, acyl donor, enzyme origin, molar ratio of substrates and reaction temperature and time, exhibited significant effects on the initial rate, conversion yield and regioselectivity of the reaction. Acylation occurred only with vinyl acetate as the acyl donor, and highest conversion yields were achieved with immobilized Penicillium expansum lipase and Novozyme 435 with DMSO and acetonitrile being the best solvents. In general, the acylation results were found to be superior to previous reports on acylation of aglycone flavonoids with respects to conversion yield and regioselectivity.
研究领域:
生物化学
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食品科学
·
药理学
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DOI
PubMed
高影响因子
Journal of the Taiwan Institute of Chemical Engineers
·
2025
·
IF 6.3
Xiaodao Liang,Yaorong He,Chao Xiong,Hongbing Ji,Yan Yang
Background Oxygen activation is a critical step in oxidation reactions for energy conversion and fine chemical synthesis, with its efficiency directly determining catalytic performance and industrial applicability. The main challenges are the high activation energy barriers and low target product selectivity caused by the inherent inertness of molecular oxygen. To address these issues, this study draws on the advantages of biomimetic catalysis using metal porphyrins and synthesizes a series of porphyrin-based organic polymers (Metal-Por-POPs) to achieve efficient aerobic epoxidation of olefins. Method A series of metalloporphyrin-based organic polymers were synthesized and thoroughly characterized using techniques such as SEM, XRD, and XPS. The catalytic performance was systematically evaluated under various conditions, including catalyst types, oxidant amount, reaction time, and temperature. Significant finding Using Mn-Por-POP as a catalyst, isobutylene was converted to the corresponding epoxide within 1 h at room temperature with a selectivity of up to 96.4 %. The catalyst also demonstrated excellent recyclability and broad substrate adaptability, maintaining over 96 % epoxide selectivity after five consecutive reaction cycles. Mechanistic studies via EPR and HRMS revealed that Mn-Por-POP promoted the generation of acyl radicals from isobutyraldehyde under aerobic conditions. These radicals subsequently reacted with molecular oxygen to form acylperoxy radicals, which facilitate the highly selective epoxidation of alkenes.
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高影响因子
危险品化学品经营许可证（带存储）