NEW JOURNAL OF CHEMISTRY
·
2022
·Vol. 46
·期 44
·21287-21300
·
IF 3.925
Yawen Yin,Xu Fei,Jing Tian,Longquan Xu,Yao Li,Yi Wang
The main challenge of rice bran oil (RBO) as a highly nutritional edible oil is the high content of free fatty acids. Biocatalytic esterification is an effective strategy to reduce acid value of RBO. In this study, polydopamine/hydroxyethyl methacrylate/acrylamide hydrogel microspheres (PHAMs) are designed and synthesized to immobilize lipase. The PHAMs have excellent water retention and provide an oil–water interface for the biocatalytic esterification of lipase. The catalytically active center of lipase is induced to open by the oil–water interface and its catalytic activity is fully developed. At the same time, the micro-water environment provided by hydrogel microspheres prevents hydrolysis of lipid products. Lipase-polydopamine/hydroxyethyl methacrylate/acrylamide hydrogel microspheres (L-PHAMs) exhibit strong immobilization capacity (enzymatic loading is 13.34 mg g−1), enhanced activity (1.11-fold that of free lipase), and excellent reusability (it maintained 37.8% of the free lipase activity after 10 cycles). The L-PHAMs still maintain 86.24% of the initial enzymatic activity after 15 days, while the free lipase activity is only 25.31%. In addition, kinetic determination shows an increased affinity between L-PHAMs and the substrate (Km is 1.07 μmol L−1). High-acid rice bran oil (HBRO) is successfully deacidified by an esterification reaction using L-PHAMs as catalysts. This process enabled an unprecedented deacidification efficiency of up to 98.19% in a short time (2 h). Overall, biocatalytic esterification by L-PHAMs is an economical and sustainable deacidification method.
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JOURNAL OF THE SCIENCE OF FOOD AND AGRICULTURE
·
2022
·Vol. 102
·期 15
·7115-7125
·
IF 4.125
Wen-Sen He,Yuying Sun,Zhishuo Li,Haonan Yang,Junjie Li,Qingzhi Wang,Chen Tan,Bin Zou
BACKGROUND α-Lipoic acid has excellent antioxidant activity, but its poor lipid solubility greatly limits its practical application. This study was undertaken (i) to develop a novel and efficient enzymatic synthesis of lipophilic lipoic acid esters using Candida sp. 99-125 lipase as a catalyst; and (ii) to systematically evaluate their antioxidant potential against bulk oil, oil-in-water emulsion (O/W) and cooked ground meat. RESULTS Lipophilic lipoic acid esters were successfully and efficiently synthesized using phytosterols as acyl receptor in the presence of Candida sp . 99-125 lipase. The product was identified as phytosterol lipoate by mass spectrometry, Fourier transform infrared spectroscopy and nuclear magnetic resonance. The maximum conversion of phytosterol lipoate surpassed 90% within 12 h and its final yield exceeded 81%. Interestingly, the oil solubility of lipoic acid was increased at least 25-fold and other physicochemical properties were significantly improved. Most importantly, phytosterol lipoate exhibited higher antioxidant activity than lipoic acid in bulk oil, O/W emulsions and cooked ground meat. CONCLUSION The antioxidant capacity of lipoic acid can be significantly enhanced by esterification with phytosterols. Therefore, phytosterol lipoate could be further developed as a new antioxidant for use in oil- and fat-based foods. © 2022 Society of Chemical Industry.
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Sustainable Chemistry and Pharmacy
·
2022
·
IF 5.464
Cheng-Kun Wu,Jin-Zheng Wang,Cheng-Hai Yan,Can-Yang Shi,Huan Chen,Sheng Sheng,Shuai You,Fu-An Wu,Jun Wang
Silkworm pupae-derived structured lipids are expected to promote the absorption of unsaturated fatty acids, however, low efficiency of bioprocess and low reusability of biocatalyst limit the corresponding biocatalysis technology . Thus, a novel strategy combining magnetic response immobilized lipase and continuous-flow microchannel reactor was proposed to modify silkworm pupae oil. The lipase from Aspergillus niger was immobilized on the surface of chitosan cross-linked magnetic nanoparticles , with increased esterification activity from 151.51 to 418.10 U/g due to the hydrophobic microenvironment. In the microchannel, the enzyme activity could be increased to 2371.3 U/g because of the strengthening effect of the microfluidic field. Furthermore, the employment of chitosan cross-linked magnetic nanoparticles leads to good reusability, and the remaining activity could stay above 90% after 13 cycles. Moreover, the immobilized lipase could be removed and loaded easily due to the employment of magnetically responsive nanoparticles. In addition, 2 min was required to rearrange the unsaturated fatty acids, increasing the relative content of sn -1.3 unsaturated fatty acids from 59.91% to 74.8% and sn -2 palmitic acid from 2.69% to 18.88%, which indicated the improved nutritional value of modified silkworm pupae oil. Therefore, the combination of microfluidic field and hydrophobic microenvironment formed by the chitosan layer on the surface of the nanoparticles effectively strengthens the biocatalysis in a solvent-free system, while the developed strategy provides a convenient biocatalysis strategy for the quality improvement of edible insect oil.
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ACS Food Science & Technology
·
2023
·
IF 2.3
Huaqing Hou,Shan Zhang,Baozhu Zhao,Jin Mao,Qi Zhou,Qianchun Deng,Lei Zheng,Jie Shi
Enzymatic esterification of phytosterols is essential for their stability and bioavailability in lipophilic foods. In this study, we created a new polydopamine-based bowl-like mesoporous carrier (BLM-PDA) for lipase loading and catalyzed the esterification of phytosterols and oleic acid to produce oleate sterol ester. Candida rugosa lipase (CRL) was selected to immobilize the polymer using physical adsorption. SEM, TEM, XRD, TGA, XPS, FT-IR, and BET were used to characterize it in order to confirm the successful preparation. These less-studied asymmetric bowl-like particles showed much enhanced performance in all aspects. According to the findings, BLM-PDA had a lipase loading of around 126.05 mg g–1, and the thermal stability and reusability of BLM-PDA@CRL fared particularly well in activity tests. After 55 h, the catalyst successfully completed the oleate sterol ester yield of 81.07% of the transesterification cycle at 40 °C. Therefore, it offers more suggestions for using an immobilized lipase nanoreactor to the biosynthesis of sterol esters.
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JOURNAL OF MOLECULAR LIQUIDS
·
2023
·
IF 6
Guangzheng Ma,Zihan Zhang,Zeping Lu,Yuan Qi,Binbin Nian,Yi Hu
The low tolerance of lipases in organic solvents limits the industrial applications of enzymatic synthesis of Vitamin E succinate (VES). In this study, the deep eutectic solvents (DESs) were adopted as mediums to achieve the high efficiency and low-cost enzymatic synthesis of VES. Several kinds of commonly used DESs, including hydrophilic and hydrophobic DESs were screened firstly and fortunately found that the decanoic acid: lidocaine (DecA: Lid 2:1) performed best in the enzymatic synthesis of VES with a yield of 98.21 ± 0.63 % at 50 ℃ in only 6 h, which was significantly improved compared to previous studies. Interestingly, a synergistic effect of lipase and DESs was found in the enzymatic synthesis of VES, and the results of molecular simulations and density functional calculation suggested that it can be attributed to that 1) the hydrogen bonds interaction between DecA:Lid (2:1) and succinic anhydride enhances the electrophilicity of succinic anhydride and promotes the esterification reaction, 2) DecA:Lid (2:1) causes conformational changes of CRL via hydrogen bonds, which improves its capacity to capture and locate substrate molecules and thus enhancing its catalytic efficiency.
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JOURNAL OF FOOD BIOCHEMISTRY
·
2023
·
IF 4
Wenjing Jiang,Qun Huang,Xiangxing Meng,Rizwan-ur Rehman,Kun Qian,Xu Yang,Xiaozhi Liu,Jingnan Chen,Ye Zhang,Jing Li,Jilite Wang,Qingbin Guo,Suwen Liu,Hao Wang
Ursolic acid (UA) is a natural triterpene carboxylic acid with an underlying anti-hyperlipidemia effect. This study examined the mechanism of interactions of UA with cholesterol esterase (CEase), pancreatic lipase (PL), and micellar cholesterol solubility in vitro. The half-maximal inhibitory concentration (IC50) of CEase, PL, and micellar cholesterol solubility was determined to be 0.07 ± 0.01 mg/mL, 1.81 ± 0.13 mg/mL, and 1.73 ± 0.08 mg/mL, respectively. Multispectral combination revealed that UA changed the secondary structure and quenched the intrinsic fluorescence by static quenching of the two enzymes. The interactions were exothermic reaction as determined by enthalpy. Furthermore, molecular docking confirmed that UA was bound to amino acids of two enzymes at active site through hydrophobic interaction and van der Waals forces. Molecular dynamics (MD) simulation found that CEase and PL rearranged with UA to form stable complexes. The strong inhibition effect of CEase and PL mediated by UA might provide additional insight into understanding the role of UA in the hypolipidemic effect.
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BIOTECHNOLOGY PROGRESS
·
2021
·Vol. 38
·期 1
·e3218
·
IF 2.681
Xiao-Jian Zhang,Feng-Yu Qi,Jia-Mei Qi,Fei Yang,Jiang-Wei Shen,Xue Cai,Zhi-Qiang Liu,Yu-Guo Zheng
The Candida antarctica lipase B (CALB) was embedded in the metal-organic framework, zeolitic imidazolate framework-8 (ZIF-8), and applied in the enzymatic synthesis of L -ascorbic acid palmitate (ASP) for the first time. The obtained CALB@ZIF-8 achieved the enzyme loading of 80 mg g −1 with 11.3 U g −1 (dry weight) unit activity, 59.8% activity recovery, and 92.7% immobilization yield. Under the optimal condition, ASP was synthesized with over 75.9% conversion of L -ascorbic acid in a 10-batch reaction. Continuous synthesis of ASP was subsequently performed in a packed bed bioreactor with an outstanding average space–time yield of 58.1 g L −1 h −1 , which was higher than ever reported continuous ASP biosynthesis reactions.
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PubMed
高影响因子
MATERIALS LETTERS
·
2021
·
IF 3.423
Chunyun Ma,Yan Zhang,Chuankai Yang,Miaorong Zhang,Jianguo Tang
Lipase was immobilized with Cu 3 (PO 4 ) 2 ⋅3H 2 O to synthesize lipase-Cu 3 (PO 4 ) 2 ⋅3H 2 O hybrid microflowers (Lip-MFs). Surfactants (Tween 80, Triton X-100 and CTAB) were added to study their effect on the morphology and activity of Lip-MFs. SEM images revealed that surfactants can increase the size of Lip-MFs and make the hierarchical structure more compact. Further, compared with other surfactants, the activity of CTAB-Lip-MFs was 1.45 times of that of free lipase, demonstrating CTAB is conducive to improve the activity of lipase.
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Food & Function
·
2021
·Vol. 12
·期 16
·7440-7447
·
IF 5.396
Ying Li,Bo Chen,Hai-Yan Cao,Jing-En Li,Ling-Li Chen,Qing-Feng Zhang
Bambusa multiplex cv Fernleaf (B. multiplex) is a species of bamboo. In the present study, B. multiplex leaf extract was prepared through the resin absorption/desorption procedure and analyzed by HPLC. C-Glycosyl flavonoids are the main constituents of B. multiplex extract, and the content of isoorientin and vitexin was 51.8 and 23.1 mg g−1, respectively. Besides, the extract exhibited inhibitory activities on pancreatic lipase and α-glucosidase with IC50 values of 0.91 and 1.16 mg mL−1, respectively. The extract could bind to pancreatic lipase and showed mixed-type inhibition. An in vivo study showed that pre-administration of B. multiplex extract significantly reduced the fat absorption in rats and increased fat excretion through feces. The change in the C-glycosyl flavonoid content in feces was the same as that in the triglyceride content. The inhibitory activity of B. multiplex leaf extract on pancreatic lipase was confirmed both in vitro and in vivo.
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PubMed
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Catalysts
·
2020
·Vol. 10
·期 4
·432
·
IF 3.52
Li-Hua Du,Rui-Jie Long,Miao Xue,Ping-Feng Chen,Meng-Jie Yang,Xi-Ping Luo
A continuous-flow procedure for the synthesis of β-amino acid esters has been developed via lipase-catalyzed Michael reaction of various aromatic amines with acrylates. Lipase TL IM fromThermomyces lanuginosuswas first used to catalyze Michael addition reaction of aromatic amines. Compared with other methods, the salient features of this work include green reaction conditions (methanol as reaction medium), short residence time (30 min), readily available catalyst and a reaction process that is easy to control. This enzymatic synthesis of β-amino acid esters performed in continuous-flow microreactors is an innovation that provides a new strategy for the fast biotransformation of β-amino acid esters.Keywords:enzymatic synthesis;β-amino acid esters;microreactor;aromatic amines;Michael addition
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ORGANIC PROCESS RESEARCH & DEVELOPMENT
·
2020
·
IF 3.023
Yuanyuan Zhang,Yangjian Sun,Hui Tang,Qiuxiang Zhao,Wenjie Ren,Kuiying Lv,Fengke Yang,Fanye Wang,Junhong Liu
The dynamic covalent kinetic resolution protocol was efficiently used for the synthesis of the enantiopure ((R)-5-acetoxy-1,3-oxathiolan-2-yl)ethyl benzoate (PR) from substrates 2-(phenylmethoxy)acetaldehyde (A), 1,4-dithiane-2,5-diol (B), and phenyl acetate (D) by a one-pot process with 99.6% conversion, 97.3% yield, and 96.5% ee through the combination of reversible hemithioacetal transformation and enantiomer-selective lactonization catalyzed by immobilized lipase from Trichosporon laibachii. A proposed kinetic model consisting of transformation and lactonization was developed herein for the first time, fitting the experimental data very well. It was concluded that (1) the transformation in a chemical fashion may follow a power law. (2) The enzymatic lactonization may follow a sequential mechanism with product inhibition. The reaction kinetic data reveal that phenol (P1) would have strong product inhibition, while noncompetitive inhibition, product inhibition of PR, and substrate inhibition were not recognized. The model suggests that there is a common limitation of both enzyme and chemistry in the chemo-enzymatic system, and thus the amount of lipase was increased to accelerate the enzymatic lactonization and to reduce the limitation caused by the enzymatic reaction, resulting in the increase of the yield of PR significantly. The experimental results demonstrate that both the internal and external mass diffusion resistance could be negligible, and thus the kinetic model developed is the inherent kinetic one.
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Processes
·
2020
·Vol. 8
·期 5
·629
·
IF 2.753
Yanhong Bi,Zhaoyu Wang,Rui Zhang,Yihan Diao,Yaoqi Tian,Zhengyu Jin
In this study, magnetic Fe3O4nanoparticles coated with polydopamine possessing abundant amino groups (Fe3O4@PDA) were conveniently prepared, detailed, and characterized, and then firstly used as a supporting matrix for immobilizingThermomyces lanuginosuslipase (Fe3O4@PDA@TLL). The effects of some crucial factors on the immobilization efficiency were investigated and the optimal protein loading and activity recovery were found to be 156.4 mg/g and 90.9%, respectively. Characterization studies revealed that Fe3O4@PDA@TLL displayed a broader pH and temperature adaptability as compared to the free TLL, which allows its use at wider ranges of reaction conditions. With regard to the stabilities, the immobilized TLL clearly displayed improved pH, thermal, and solvent tolerance stabilities compared to the free enzyme, suggesting that the biocompatible Fe3O4@PDA might be an outstanding material for immobilizing TLL and acting as alternative support for different enzymes.Keywords:magnetic nanoparticle;immobilization;Thermomyces lanuginosuslipase;stability
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