LWT-FOOD SCIENCE AND TECHNOLOGY
·
2022
·
IF 6.056
Duan Zhou,Mouming Zhao,Jiankang Wang,Muniba Faiza,Xuefeng Chen,Junjie Cui,Ning Liu,Daoming Li
Punicic acid (PA)-enriched diacylglycerol (DAG) possesses both the beneficial effects of PA and DAG. However, few studies have focused on the preparation of PA-enriched DAG. Here, we report a novel and highly efficient method for the preparation of PA-enriched DAG through Lipozyme 435-catalyzed ethanolysis of pomegranate seed oil (PSO). Firstly, PSO was obtained through microwave-assisted extraction. Subsequently, four lipases were screened for their capability in the preparation of PA-enriched DAG through ethanolysis of PSO (containing 82.98% PA), and Lipozyme 435 was selected. Under the optimal conditions, the resultant mixture containing 32.86% DAG was obtained. Interestingly, Lipozyme 435 maintained superior operational stability after ten successive cycles. A scale-up reaction was then conducted under the optimized conditions and the purified product containing 51.83% DAG (containing 81.95% PA) was obtained. The final product with a low peroxide value (1.45 mmol/kg) and undetectable acid value reached edible quality. This is the first study for the preparation of PA-enriched DAG through ethanolysis and Lipozyme 435 exhibited superior capability and recyclability. Compared with other approaches for DAG preparation, this approach favored shorter reaction time and better quality of the product. This study provides useful information for further studies involving DAG preparation and modification of PSO.
研究领域:
食品科学
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生物化学
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DOI
高影响因子
Molecular Catalysis
·
2025
·
IF 4.9
Duan Zhou,Mouming Zhao,Xiaorong Zhong,Xuefeng Chen,Ning Liu,Daoming Li
Diacylglycerol (DAG) has extensive applications in many fields due to its health benefits and amphiphilic property. Herein, enzymatic esterification of oleic acid and glycerol in natural deep eutectic solvents (NADESs) was employed to synthesize DAG. Firstly, Novozym 435 and choline chloride: glycerol (ChCl:Gly) system were selected as the most appropriate immobilized lipase and NADES for DAG synthesis. Subsequently, the reaction conditions of Novozym 435-catalyzed esterification in ChCl:Gly system were optimized, and the content of DAG reached as high as 67.08 wt % ± 0.79 wt % under the optimal conditions (molar ratio of oleic acid to glycerol of 1:4, reaction temperature of 50 °C, enzyme dosage of 4 wt % with respect to the total weight of substrates, reaction time of 7 h). At last, the reasons why ChCl:Gly could induce a higher DAG content were explored from thermodynamics, water activity and reaction interface. The results showed that ChCl:Gly system could absorb the generated water during esterification and increase the reaction interface, thus beneficial to DAG synthesis. Moreover, the activation energy of DAG production (55.36 kJ/mol) was significantly lower than that of monoacylglycerol (MAG) production (62.60 kJ/mol), leading to the priority of DAG production. Briefly, the multiple beneficial effects of NADESs on lipase-catalyzed esterification collectively contributed to an enhancement of DAG content in esterification products.
研究领域:
生物化学
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食品科学
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DOI
高影响因子
FOOD CHEMISTRY
·
2025
·
IF 9.8
Run Liu,Yi Zhang,Yuanzhi Xu,Zhonghui Liu,Jinhang Chen,Kheng-Lim Goh,Yufei Zhang,Mingming Zheng
Diacylglycerol (DAG) is a functional lipid that is naturally present in vegetable oils in limited concentrations (1 %–5 %). This study proposed an enzymatic method to afford high-content-DAG vegetable oils via a reaction catalyzed by an immobilized lipase, PS@OMS-C 8 , using high-speed homogenization and molecular distillation. Results indicated that 48.6 % DAG was initially obtained through the enzymatic glycerolysis of rapeseed oil with glycerol, of which 90.2 % was sn -1,3-DAG. PS@OMS-C 8 maintained 35.5 % DAG content after 10 reuse cycles, confirming its catalytic stability; this was attributed to lipase immobilization on the ordered mesoporous silica that significantly improve the secondary protein structures, including α-helix and β-sheet, thereby strengthening the rigidity of PS@OMS-C 8 . In addition to producing DAG-enriched rapeseed oil, other edible oils with 39.4 %–50.2 % DAG content were obtained, as revealed via molecular docking simulation. This study offers new strategies for the sustainable synthesis of vegetable oils with a high content of functional lipids high-content functional lipids.
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
PROTEIN EXPRESSION AND PURIFICATION
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2025
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IF 1.2
Yipeng Chen,Bin Huai,Jin Chuan Wu,Ning Zhang,Yong Wang,Qingxin Li
The structural and functional investigation of bacterial membrane proteins is crucial to the development of antibiotics. Diacylglycerol kinase (DAGK) from Escherichia coli ( E. coli ) has been extensively studied as a model membrane protein. However, the DAGK from Pseudomonas aeruginosa (PAO1-DAGK) with a 44% sequence identity to E. coli -DAGK is not well characterized. To explore the properties of PAO1-DAGK, it was successfully expressed in E. coli and was purified in Decyl-β-D-maltoside (DM) micelles followed with characterizations. Chemical cross-linking studies revealed that PAO1-DAGK in DM micelles could form dimers and trimers. The kinase activity of PAO1-DAGK was determined to be 24.2 ± 2.2 U/mg protein in a mixed-micelle system. The effects of pH and temperature on the activity of PAO1-DAGK were also investigated, respectively. PAO1-DAGK in DM micelles exhibited good stability at pH 6.0–10.0 and below 45°C. Substrate specificity measurements indicated that PAO1-DAGK demonstrated a clear preference for medium-chain diacylglycerols (DAGs) in the mixed-micelle system, with sn-1,2-Dihexanoylglycerol (DiC6) being the most favored substrate. Molecular docking results demonstrated the interactions between DAGs and PAO1-DAGK.
研究领域:
微生物学
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生物化学
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产品关联
DOI
PubMed
高影响因子
FEBS Journal
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2015
·Vol. 282
·期 23
·4538-4547
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IF 4.001
Shaohua Guo,Jinxin Xu,Ioannis V. Pavlidis,Dongming Lan,Uwe T. Bornscheuer,Jinsong Liu,Yonghua Wang
Monoacylglycerol and diacylglycerol lipases are industrially interesting enzymes, due to the health benefits that arise from the consumption of diglycerides compared to the traditional triglyceride oils. Most lipases possess an α-helix (lid) directly over the catalytic pocket which regulates the activity of the enzyme. Generally, lipases exist in active and inactive conformations, depending on the positioning of this lid subdomain. However, lipase SMG1, a monoacylglycerol and diacylglycerol specific lipase, has an atypical activation mechanism. In the present study we were able to prove by crystallography, in silico analysis and activity tests that only two positions, residues 102 and 278, are responsible for a gating mechanism that regulates the active and inactive states of the lipase, and that no significant structural changes take place during activation except for oxyanion hole formation. The elucidation of the gating effect provided data enabling the rational design of improved lipases with 6-fold increase in the hydrolytic activity toward diacylglycerols, just by providing additional substrate stabilization with a single mutation (F278N or F278T). Due to the conservation of F278 among the monoacylglycerol and diacylglycerol lipases in the Rhizomucor miehei lipase-like family, the gating mechanism described herein might represent a general mechanism applicable to other monoacylglycerol and diacylglycerol lipases as well. Database Structural data are available in the Protein Data Bank under the accession numbers 4ZRE (F278D mutant) and 4ZRD (F278N mutant).
研究领域:
生物化学
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分子生物学
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酶工程
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DOI
PubMed
高影响因子
FOOD CHEMISTRY
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2018
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IF 4.946
Nanjing Zhong,Weilin Chen,Liyan Liu,Hongxiao Chen
In this study, mesoporous silica SBA-15 was modified by organic functional groups through silanization. Series of organosilane compounds were grafted onto the SBA-15, and the obtained functionalized carriers were then used to immobilize the lipase from Rhizomucor miehei (RML). The enzymatic properties of the obtained immobilized RML samples were evaluated, and the catalytic efficiencies in glycerolysis of triacylglycerols (TAG) reaction were studied. Compared with the parent SBA-15 immobilized RML, the organic modification gave a maximum improvement of enzymatic activity from 200.00 to 13211.11 U/g; in addition, TAG conversion and diacylglycerols (DAG) content increased from 21.28 to 84.24% and 15.45 to 59.03% respectively. The organic modification also decreased the sensitivity of immobilized RML in extreme pH values and increased their thermostability.
研究领域:
生物化学
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酶工程
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产品关联
DOI
PubMed
高影响因子
JOURNAL OF THE SCIENCE OF FOOD AND AGRICULTURE
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2013
·Vol. 94
·期 8
·1614-1621
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IF 1.759
Xiao-Li Qin,Dong-Ming Lan,Jin-Feng Zhong,Lu Liu,Yong-Hua Wang,Bo Yang
BACKGROUND T1 lipase has received considerable attention due to its thermostability. Fatty acid specificity of T1 lipase (crude and purified) was investigated, and its potential in the synthesis of acylglycerols was also evaluated . RESULTS Fatty acid specificity of T1 lipase (crude and purified) was investigated in the esterification of fatty acids (C6:0 to C18:3), suggesting that crude and purified T1 lipase had the lowest preference for C18:0 [specificity constant (1/ α ) = 0.08] followed by C18:1 (1/ α = 0.12) and showed the highest preference for C8:0 (1/ α = 1). A structural model was constructed to briefly explore interactions between the lipase and its substrate. Furthermore, crude T1 lipase-catalysed synthesis of diacylglycerols (DAGs) and monoacylglycerols (MAGs) by esterification of glycerol with C18:1 was studied for evaluating its potential in acylglycerols synthesis. The optimal conditions were glycerol/oleic acid molar ratio 5:1, the lipase concentration 9.7 U g −1 of substrates, water content 50 g kg −1 of substrates and temperature 50 °C, which yielded 42.25% DAGs, 26.34% MAGs and 9.18% triacylglycerols at 2 h . CONCLUSION DAGs and MAGs were synthesised in good yields although C18:1 (a much poorer substrate) was used. Our work demonstrates that T1 lipase, which was discovered to show 1,3-regio-selectivity, is a promising biocatalyst for lipids modification. © 2013 Society of Chemical Industry
研究领域:
生物化学
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酶工程
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DOI
PubMed
高影响因子
Engineering
·
2025
·
IF 11.6
Zhonghui Liu,Yi Zhang,Tieliang Liu,Qi Zhou,Yandaizi Zhou,Kheng-Lim Goh,Siew-Young Quek,Fenghong Huang,Mingming Zheng
Algae oil contains polyunsaturated fatty acids (PUFAs) that are beneficial to human health and development. Enzymatic refining is a sustainable approach that can improve the quality and nutritional value of algae oil. However, this approach involves the use of specific enzymes to remove unwanted impurities such as phospholipids (PLs) and free fatty acids (FFAs). This study proposes a novel immobilized phospholipase, immobilized phospholipase A1 (PLA1@MCM-41-C 8 ), which serves a dual purpose: it is effective for both degumming arachidonic acid (ARA)-enriched algal oil and its subsequent deacidification. The use of PLA1@MCM-41-C 8 achieved a degumming rate of 95.9% for crude algal oil, with an ARA retention rate of up to 97.3%. The acidity of the degummed oil decreased from 14.5 to 1.1 mg KOH∙g −1 , while simultaneously producing 29.2% high-value diacylglycerol (DAG). By comparing enzymatically degummed and deacidified ARA-enriched algae oil (EDDO) with crude ARA-enriched algae oil (CO), commercialized refining algae oil (CRO), it was found that enzymatic refining had minimal impact on antioxidant stability, fatty acid composition, and oil content. In particular, the flavor characteristics of algal oil before and after enzymatic refining with PLA1@MCM-41-C 8 remained unchanged and were dominated by the main volatile compounds: alcohols and aldehydes. Compared with free phospholipase A1 (PLA1), PLA1@MCM-41-C 8 exhibited significantly improved thermostability, pH tolerance, solvent tolerance, and long-term reusability. These characteristics make it a promising candidate for complex oil refining in industrial applications.
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产品关联
DOI
高影响因子
Journal of Oleo Science
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2024
·
IF 1.6
Siliang Ding,Xiaohan Chen,Bo Ouyang,Bo Yang,Weifei Wang,Yonghua Wang
In the pursuit of reducing oil separation in peanut butter, oleogels synthesized from diacylglycerol (DAG)-rich peanut oils, using glycerol monostearate (GMS) as the gelator, were examined as alternative stabilizers. In comparison to triacylglycerol (TAG)-rich peanut oils, the DAG oil-based oleogels exhibited better oil-binding capacities across increasing GMS concentrations. Intriguingly, thermal and rheological assessments pointed to a weaker network structure in DAG oil oleogels, as evidenced by their lower crystallization temperatures and reduced viscoelastic parameters (G' and G''). Insight from infrared spectroscopy revealed that this could stem from heightened intermolecular hydrogen bonding between the DAG oil and the gelator. When applied to peanut butter, DAG oil oleogels demonstrated efficacy in minimizing oil separation. Extended storage trials affirmed the long-term stability of peanut butter formulations incorporating these oleogels. Furthermore, sensory evaluations by panelists underscored favorable impressions, suggesting potential consumer acceptance. Overall, this study illuminates the promising role of DAG oleogels as effective, alternative stabilizers in peanut butter formulations.
研究领域:
食品科学
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化学工程
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材料科学
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产品关联
DOI
PubMed
高影响因子
JOURNAL OF THE SCIENCE OF FOOD AND AGRICULTURE
·
2019
·Vol. 100
·期 4
·1426-1435
·
IF 2.422
Xihong Zhao,Fenghuan Zhao,Nanjing Zhong
BACKGROUND In this study, SBA-15 was functionalized by silane coupling reagents, then lipase from Thermomyces lanuginosus (TLL) was immobilized onto the parent and the organically modified SBA-15 for diacylglycerol (DAG) production through glycerolysis. RESULTS Diacylglycerol content of 54.77 ± 0.63%, and triacylglycerol (TAG) conversion of 77.75 ± 1.24%, were obtained from the parent SBA-15 supported TLL-mediated glycerolysis reaction in a solvent-free system. However, poor performance was unexpectedly observed when co-solvents were introduced into the reaction system. After organic modification, the functionalized SBA-15 supported TLL samples all exhibited reasonable performance, producing DAG content over 40 wt% and TAG conversion over 70 wt%. Higher DAG content, up to 59.19 ± 1.10%, was observed from the phenyl group-modified SBA-15 supported TLL. The operational stability of the immobilized TLL samples in glycerolysis was also improved after organic functionalization. The phenyl group-modified SBA-15 supported TLL showed good reusability in the present glycerolysis reaction, and 95.21 ± 4.87% of the initial glycerolysis activity remained after five cycles of reuse. CONCLUSION The organic modification of SBA-15 improved the catalytic performance of its supported TLL in glycerolysis, in terms of TAG conversion, DAG content, and reusability. © 2019 Society of Chemical Industry
研究领域:
化学工程
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生物催化
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材料科学
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产品关联
DOI
PubMed
高影响因子
Foods
·
2024
·Vol. 13
·期 16
·2589
·
IF 4.7
Xiaohan Chen,Xiaoxia Chen,Daoming Li,Weifei Wang
The purpose of this study was to substitute shortening with olive diacylglycerol oil/candelilla wax (OCW)–olive diacylglycerol stearin (ODS) oleogels and evaluate their impact on starch digestibility in cookies. The in vitro digestibility study confirmed that the OCW/ODS–based cookies exhibited a notable enhancement of 14.6% in slowly digestible starch (SDS) and an increase of 3.14% in resistant starch (RS) values when contrasted with shortening cookies. The XRD pattern indicated that the existence of ODS may improve the formation of complexes between lipids and amylose. The DSC analysis demonstrated that the incorporation of ODS led to a remarkable rise in enthalpy alteration, escalating from 0.90 to 437.70 J/g, suggesting an improved ability to resist gelatinization. The FTIR spectra suggested that the incorporation of ODS might strengthen interactions between the hydrogen bonds and form the short–range ordered structure in OCW/ODS–based cookies. Overall, these results indicated that incorporating OCW/ODS–based oleogels could serve as a feasible substitute for conventional shortening in cookies with decreased starch digestibility.
研究领域:
食品科学
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营养学
·
材料科学
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DOI
PubMed
高影响因子
JOURNAL OF DAIRY SCIENCE
·
2024
·
IF 3.7
Shuang Wang,Bingbing Zhang,John Mauck,Juan J. Loor,Wenwen Fan,Yan Tian,Tianjiao Yang,Yaqi Chang,Meng Xie,Ben Aernouts,Wei Yang,Chuang Xu
ABSTRACT Hepatocellular lipid accumulation characterizes fatty liver in dairy cows. Lipid droplets (LD), specialized organelles that store lipids and maintain cellular lipid homeostasis, are responsible for the ectopic storage of lipids associated with several metabolic disorders. In recent years, non-ruminant studies have reported that LD-mitochondria interactions play an important role in lipid metabolism. Due to the role of diacylglycerol acyltransferase isoforms (DGAT1 and DGAT2) in LD synthesis, we explored mechanisms of mitochondrial fatty acid transport in ketotic cows using liver biopsies and isolated primary hepatocytes. Compared with healthy cows, cows with fatty liver had massive accumulation of LD and high protein expression of the triglyceride (TAG) synthesis-related enzymes DGAT1 and DGAT2, LD synthesis-related proteins perilipin 2 (PLIN2) and perilipin 5 (PLIN5), and the mitochondrial fragmentation-related proteins dynamin-related protein 1 (DRP1) and fission 1 (FIS1). In contrast, factors associated with fatty acid oxidation, mitochondrial fusion and mitochondrial electron transport chain complex were lower compared with those in the healthy cows. In addition, transmission electron microscopy revealed significant contacts between LD-mitochondria in liver tissue from cows with fatty liver. Compared with isolated cytoplasmic mitochondria, expression of carnitine palmitoyl transferase 1A (CPT1A) and DRP1 was lower, but mitofusin 2 (MFN2) and mitochondrial electron transport chain complex was greater in isolated peridroplet mitochondria from hepatic tissue of cows with fatty liver. In vitro data indicated that exogenous free fatty acids (FFA) induced hepatocyte LD synthesis and mitochondrial dynamics consistent with in vivo results. Furthermore, DGAT2 inhibitor treatment attenuated the FFA-induced upregulation of PLIN2 and PLIN5 and rescued the impairment of mitochondrial dynamics. Inhibition of DGAT2 also restored mitochondrial membrane potential and reduced hepatocyte reactive oxygen species production. The present in vivo and in vitro results indicated there are functional differences among different types of mitochondria in the liver tissue of dairy cows with ketosis. Activity of DGAT2 may play a key role in maintaining liver mitochondrial function and lipid homeostasis in dairy cows during the transition period.
研究领域:
动物科学
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代谢
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分子生物学
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兽医学
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DOI
PubMed
高影响因子
危险品化学品经营许可证（带存储）