FOOD RESEARCH INTERNATIONAL
·
2025
·
IF 8
Zeqing Liu,Ziteng Su,Lingmei Dai,Dehua Liu,Wei Du
1,3-dioleoyl-2-palmitoylglycerol (OPO) and 1-oleoyl-2-palmitoyl-3-linoleoylglycerol (OPL) are two essential types of human milk fat substitutes (HMFS). Their unique fatty acid composition and distribution play a significant role in promoting infant health, making the reaction conversion and acyl migration critical factors for developing efficient preparation methods. Promoting the conversion of the substrate while simultaneously inhibiting acyl migration is crucial for obtaining the desired HMFS products. In this study, we comparatively investigated enzymatic acidolysis and transesterification for HMFS production and revealed enzymatic kinetics as well as acyl migration mechanism during the process. Acyl migration was observed through the lipase-catalyzed mechanism, and the associated free energy changes were analyzed using density functional theory (DFT). The presence of long-chain fatty acids in the synthesis system resulted in intermediates with higher relative free energy during acyl migration. Based on these findings, we propose a novel synthesis strategy consisting of multi-step transesterification and dry fractionation, leveraging the differences in freezing points to minimize acyl migration. The resulting OPO product contains 90.42% oleic acid specifically at the sn -1,3 positions, highlighting its potential application in infant formulas. This study presents a systematic investigation of the kinetics and mechanisms involved in lipase-mediated HMFS production, providing valuable insights for rational synthesis approaches.
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JOURNAL OF SURFACTANTS AND DETERGENTS
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2024
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IF 1.6
Qinzhou Cai,Huifang Zhang,Bingshan Zhao,Lei Ren,Yonghua Wang,Fanghua Wang
Cold-adapted, alkali-stable lipases with surfactant tolerance are highly sought after in the detergent industry. In this study, we recombinantly expressed and characterized a novel lipase from Marinobacter nanhaiticus (MNL). The purified MNL exhibited high stability within a temperature range of 10–30°C and pH values of 8–10, demonstrating optimal activity at 20°C and pH 8. MNL has a preference for substrates with medium chains with the best activity being 3768.6 U/mg using p -nitrophenyl decanoate as a substrate. Remarkably, MNL showed enhanced enzymatic activity in the presence of ionic surfactants and displayed notable resilience when exposed to proteases. Washing performance analysis further revealed MNL's high proficiency in removing oil-based stains from fabrics. Collectively, these results suggest that MNL holds significant promise as a valuable component in laundry detergent formulations.
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ENZYME AND MICROBIAL TECHNOLOGY
·
2015
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IF 2.322
Xuemei Tian,Suoqin Zhang,Liangyu Zheng
The first Novozym 435 lipase-catalyzed Morita–Baylis–Hillman (MBH) reaction with amides as co-catalyst was realized. Results showed that neither Novozym 435 nor amide can independently catalyze the reaction. This co-catalytic system that used a catalytic amount of Novozym 435 with a corresponding amount of amide was established and optimized. The MBH reaction strongly depended on the structure of aldehyde substrate, amide co-catalyst, and reaction additives. The optimized reaction yield (43.4%) was achieved in the Novozym 435-catalyzed MBH reaction of 2, 4-dinitrobenzaldehyde and cyclohexenone with isonicotinamide as co-catalyst and β-cyclodextrin as additive only in 2 days. Although enantioselectivity of Novozym 435 was not found, the results were still significant because an MBH reaction using lipase as biocatalyst was realized for the first time.
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ACS Applied Nano Materials
·
2024
·
IF 5.3
Zeqing Liu,Yuhan Li,Lingmei Dai,Dehua Liu,Wei Du
Single-crystalline ordered macro-microporous CuBTC shows excellent mass transfer performance and has high fatty acid stability, making it highly promising as an enzyme immobilization carrier. However, its practical application is severely limited by its poor water stability. To address this challenge, we introduced a ligand, 1,2,3-benzotriazole (BTA), known for its hydrophobicity and strong coordination with copper. A series of CuBTC-derived dual-ligand SOM-MOFs (SOM-MIXs) was successfully synthesized with enhanced hydrophobicity and improved water stability. The CuBTC-derived SOM-MIXs demonstrated superior performance for lipase immobilization, resulting in a maximum increase of 66.9% in specific activity. To address the limitation that excessive addition of 1,2,3-benzotriazole does not further enhance the hydrophobicity of the carrier and may lead to structural damage, a sol–gel method was employed to coat the SOM-MIX with highly hydrophobic PDMS, leading to a further increase of 139.1% in the specific activity. The resulting immobilized lipase exhibited excellent catalytic performance and remarkable reusability, with 90.09% activity retention after five cycles in the synthesis process of 1-oleoyl-2-palmitoyl-3-linoleoylglycerol (OPL) by acidolysis. This work highlights the potential of SOM-MIX@PDMS and provides valuable insights into the rational design and postmodification of metal–organic frameworks (MOFs) for enzyme immobilization in diverse applications.
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COLLOIDS AND SURFACES B-BIOINTERFACES
·
2024
·
IF 5.4
Xia Jiaojiao,Feng Ting,Suo Hongbo,Yan Lishi,Zou Bin
In this study, the covalent organic framework immobilized Rhizomucor miehie lipase COF@RML as a novel biocatalyst was applied in the enzymatic synthesis of OPO structured lipids (1, 3-dioleoyl-2-palmitoylglycerol). The impact of reaction medium, substrate molar ratio, enzyme addition amount, reaction time and temperature on the enzymatic synthesis of OPO structured lipids were studied. Furthermore, the effects of ultrasonic power and ultrasonic time on the synthesis of OPO structural lipids were studied. The results showed that ultrasonication could increase the yeild of OPO structured lipids by improving substrate mass transfer and enzyme particle dispersion. The optimal process for the synthesis of OPO structured lipids was obtained. When the ultrasonic power was set at 90 W, ultrasonic time at 12 minutes, enzyme addition amount at 10 wt%, substrate molar ratio at 1:8, reaction temperature at 45 °C, and reaction time at 6 hours, the yield of OPO structured lipids reached a remarkable 51.27 %. Finally, the commercial lipase Lipozyme RM IM was compared with the COF@RML. The findings indicated that COF@RML immobilized enzyme had better application value in the synthesis of OPO structured lipids.
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JOURNAL OF FOOD ENGINEERING
·
2025
·
IF 5.8
Caiyun Wang,Changhao Liu,Zhicen Liu,Han Xu,Yue Zhang
Sugar fatty acid esters, serving as multifunctional biosurfactants, are extensively utilized in food formulations for emulsification, foam stabilization, and microbial preservation. Enzymatic transesterification using lipases offers distinct advantages over chemical synthesis, including mild reaction conditions and reduced energy consumption. In this study, we engineered a cold-adapted lipase (Lip) through lid domain truncation and mutation, yielding the optimized variant Lip-8 to alleviate substrate channel steric hindrance, coupled with tannic acid-modified magnetic nanoflowers (TA-MNFs) via a one-pot immobilization strategy to create Lip-8/TA-MNFs. This immobilized enzyme demonstrated significantly enhanced catalytic performance, achieving a 12.91-fold activity increase compared to free lipase. Under optimized conditions (40 °C, 36 h), the system synthesized fructose laurate esters with 93.07 % conversion efficiency. Structural characterization confirmed the predominant formation of mono- and di-esters, which exhibit dual surfactant and emulsifying properties suitable for food-grade applications.
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CHIRALITY
·
2024
·Vol. 36
·期 2
·e23643
·
IF 2.8
Xiaojun Li,Qi Li,Liying Yang,Liqin Huang,Chenchen Peng,Jianyong Zheng
In this study, lipase-catalyzed resolution of N-acetyl-DL-methionine methyl ester (N-Ac-DL-MetOMe) was evaluated. A lipase from Brucella thiophenivorans was prone to exhibit high activity and excellent enantioselectivity toward N-Ac-DL-MetOMe to produce the key chiral intermediate N-acetyl-L-methionine methyl ester (N-Ac-L-MetOMe). The results showed that the enzymatic reaction was carried out in 100 g/L racemic substrate for 2 h, the conversion reached 51.3%, the enantiomeric excess value N-Ac-L-MetOMe exceeded 99%, and the enantiomeric ratio value >200. Therefore, the lipase from B. thiophenivorans has potential prospects for the resolution of N-Ac-DL-MetOMe to produce the important intermediate N-Ac-L-MetOMe.
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MOLECULES
·
2025
·Vol. 30
·期 11
·2429
·
IF 4.6
Wei Wang,Xiangyao Chen,Wen-Can Huang,Simiao Di,Jie Luo
This study presents a multilayer magnetic Janus sub-micrometric particle (MMJSP) as a nanoreactor for lipase catalysis. The core of the nanoparticle is constructed from a core-shell Fe3O4@SiO2framework, which serves as a precursor for the sequential amino and aldehyde modifications using 3-aminopropyltriethoxysilane and benzaldehyde. Following localized etching and subsequent modification with N,N-dimethyldodecylamine, a Janus nanoparticle with distinct hydrophilic and hydrophobic domains is synthesized. The resulting MMJSP demonstrates a stable attachment to the reaction interface and significantly enhances lipase performance, exhibiting 1.4-fold and 1.6-fold enhancements in activity after immobilization during 1 h hydrolysis and 24 h esterification reactions, respectively. Additionally, the storage stability of the immobilized lipase is improved by 100% over a period of 30 days. Reusability assessments reveal that the immobilized enzyme retains 80.7% activity after 10 cycles of esterification and 80.6% after 50 cycles of hydrolysis, with the magnetic properties allowing for rapid separation and recovery of the immobilized enzyme.
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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
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FOOD RESEARCH INTERNATIONAL
·
2025
·
IF 8
Huanyu Zheng,Ji Zhang,Zhouliang Sun,Mengqi Wang,Yufei Zhang,Mingming Zheng
Nature employs non-catalytic scaffold proteins to achieve precise enzyme positioning and enhanced catalysis. However, mimicking this approach with food-grade macromolecular materials remains a significant challenge. Herein, we introduce a pH-tunable gliadin-chitosan matrix designed to act as a bioinspired scaffold. It spontaneously self-assembles with lipase into stable ternary complex, gliadin-chitosan-lipase (GCL), through robust hydrogen bonding and hydrophobic interactions (∆G_binding = −331.7 kJ‧mol −1 ) immobilize lipase AYS in an optimally active conformation. Upon addition to an oil-water mixture at pH 7, GCL particles adsorb at the interface, creating a highly efficient Pickering interfacial biocatalysis (PIB) system. When applied to the synthesis of sterol esters via interesterification with flaxseed oil, the GCL-stabllized PIB system achieved an 81.4 % yield within 6 h, a relative conversion rate of almost three times that of free lipase (31.8 %), and maintained 73.4 % of its initial activity after five consecutive cycles. Its compatibility extended to six commercial oils. Molecular dynamics results indicated that lipase acts as a regulatory element, suppressing global fluctuations to generate stable structures with high catalytic activity, thereby preparing the interface for biocatalysis. This work establishes a sustainable, scalable platform for functional lipid production and provides a blueprint for next-generation biomacromolecular enzyme carriers.
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Food Bioscience
·
2020
·
IF 3.067
Liang Gao,Xinyi Cheng,Xuwei Yu,Xiaosan Wang,Qingzhe Jin,Xingguo Wang
1-Oleoyl-2-palmitoyl-3-linoleoylglycerol (OPL) is a critical structured lipid in human milk fat and it plays an important role in infants' health. The development of an efficient method for such compound preparation is necessary. In this study, one- and two-step methods for OPL production by enzymatic acidolysis of fractionated palm stearin with mixed acids were compared in solvent-free and solvent systems. The results demonstrated that in the solvent system, the OPL contents by the one- and two-step methods were 45.8% and 56.7%, respectively. In the solvent-free system, the one- and two-step methods resulted in the formation of 43.7% and 54.8% OPL, respectively. Subsequently, acidolysis conditions of the two-step method were optimized. Under the optimum conditions, the content of OPL was 57.7%, and 83.2% of palmitic acid was at the sn-2 position . The prepared OPL has potential to be applied in infant formulas.
研究领域:
食品科学
·
生物化学
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Life-Basel
·
2026
·Vol. 16
·期 2
·235
·
IF 3.9
Qingfeng Guo,Xia Zhang,Hao Zhang,Mengxue Wang,Haoran Zhou,Meiru Chen,Zhenhua Yin,Juanjuan Zhang,Baocheng Yang,Li Wang,Lin Chen
Originating in East Asia, the adzuki bean (Vigna angularis) is a diploid crop mainly grown in this region that belongs to the Fabaceae family. As a potential functional food resource with both medicinal and nutritional value, it offers various health benefits. However, research on its chemical constituents, particularly key bioactive components such as triterpenoid saponins and flavonoids, remains relatively limited. In this study, a new triterpenoid saponin, adzukisaponin A (1), along with eleven known compounds (2–12), were isolated from adzuki bean (V. angularis). Among them, compounds3(yunganoside B1),6(3β-acetyl oleanolic acid), and7(β-amyrin) are reported from this source for the first time. Saponins1–3and flavonoid8exhibited significant dual inhibitory activity. Notably, saponins1–3inhibited pancreatic lipase (IC50= 0.11 ± 0.18 to 0.40 ± 0.21 mM) more strongly than the positive control orlistat, while also acting against α-glucosidase (IC50= 0.14 ± 0.11 to 0.23 ± 0.17 mM). Molecular docking supported their binding to the enzymes’ active sites. This study identifies1–3and8as dual α-glucosidase/pancreatic lipase inhibitors, underscoring the potential of adzuki bean as a source of bioactive functional food ingredients.
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