COLLOIDS AND SURFACES B-BIOINTERFACES
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2024
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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.
研究领域:
生物化学
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食品科学
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酶工程
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DOI
PubMed
高影响因子
INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES
·
2025
·
IF 8.5
Xiang Zhou,Jiahao Xu,Jiayao Sun,Hao Chen,Dechun Huang,Wei Chen,Hongliang Qian
1,3-Dioleoyl-2-palmitoylglycerol (OPO) is crucial for infant nutrition; however, conventional immobilized lipase requires high-purity enzymes, which increases costs and limits industrial scalability. Herein, Rhizomucor miehei lipase (RML) was immobilized on surface-modified magnetic nanoparticles using cross-linked enzyme aggregates (CLEAs) technology to produce Fe 3 O 4 @SiO 2 @TPOAC@RML CLEAs. This approach combines the separation and immobilization of enzymes, allowing for the use of lower-purity lipase, which enhances its suitability for industrial-scale processes. The optimized Fe 3 O 4 @SiO 2 @TPOAC@RML CLEAs exhibited excellent thermal, pH, and storage stability. The performance of Fe 3 O 4 @SiO 2 @TPOAC@RML CLEAs was evaluated by catalyzing the synthesis of OPO through the enzymatic hydrolysis of glycerol tripalmitate (PPP) and oleic acid (OA). Under optimal conditions, the OPO content in products reached 63.33 ± 0.30%, highlighting the high efficiency of the enzymatic process. After eight reuse cycles, the Fe 3 O 4 @SiO 2 @TPOAC@RML CLEAs retained around 75% of their relative activity. Therefore, this strategy of lipase immobilization using CLEA technology, coupled with magnetic nanoparticles, offers a promising approach for OPO synthesis.
研究领域:
生物催化
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纳米技术
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酶固定化
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食品化学
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工业生物技术
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产品关联
DOI
PubMed
高影响因子
Food Biophysics
·
2022
·Vol. 17
·期 4
·495-507
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IF 3.34
Ghide Michael Kidane,Li Kai,Wang Jianhua,Abdulmalek Saadiah A.,Yan Yunjun
1,3-Dioleoyl-2-palmitoyl glycerol (OPO)-supplemented infant formulas mimic the nutritional properties of human milk, and thus are the best nutritional alternatives to breast feeding. Herein, structured triacyl glycerides rich in sn-1,3 oleic acid (OA) and sn-2 palmitic acid (PA) are synthesized via a new strategy by employing Rhizomucor miehei lipase (RML) adsorbed on magnetized multiwalled carbon nanotubes (mMWCNT) and synthesizing OPO-rich fats in a two-step enzymatic acidolysis. The results showed that the immobilized lipase (mMWCNT-COOH-RML) exhibited improved pH and thermal stability, and it could be separated conveniently from the reaction system via an external magnetic field. It also possessed a much better performance in catalysis of tripalmitin (PPP) with OA to synthesize OPO-rich fats in a two-step enzymatic acidolysis. Under optimized conditions, the content of palmitic acid at the sn-2 position and incorporation of OA at the sn-1,3 positions respectively reached 92.93% and 57.82%. mMWCNT-COOH-RML also exhibited better reusability and catalytic activity than the conventionally used commercial Lipozyme RM IM. The results indicate the employed new strategy for synthesis of OPO-rich fats has a prosperous potential in the application of infant formula formulations.
研究领域:
食品科学
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化学工程
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生物技术
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DOI
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
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生物技术
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DOI
PubMed
高影响因子
LWT-FOOD SCIENCE AND TECHNOLOGY
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2019
·
IF 3.714
Xiaosan Wang,Cong Jiang,Wendi Xu,Zhicheng Miu,Qingzhe Jin,Xingguo Wang
Structured triacylglycerols (TAGs), rich in 1,3-dioleoyl-2-palmitoylglycerol (OPO) and 1-oleoyl-2-palmitoyl-3-linoleoylglycerol (OPL), were prepared by enzymatic acidolysis of fractionated palm stearin with free fatty acids . The effects of enzyme type, substrate molar ratio, enzyme load, temperature, and reaction time on the yields of OPO and OPL, palmitic acid (PA) content at the sn- 2 position of TAG, and the percentage of PA at the sn- 2 position relative to total PA content were investigated. Under optimal reaction conditions (palm stearin/oleic acid/linoleic acid molar ratio of 1:8:4, lipase NS 40086 loading of 8%, 60 °C, 4 h), the combined yields of OPO and OPL was 69.26%, PA content at the sn- 2 position reached 87.75%, and the relative percentage of PA at the sn- 2 position was up to 71.07%. The synthesized TAGs have potential to be used in infant formulas.
研究领域:
食品科学
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生物化学
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产品关联
DOI
高影响因子
JOURNAL OF THE AMERICAN OIL CHEMISTS SOCIETY
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2016
·Vol. 93
·期 10
·1347-1354
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IF 1.505
Siyun Gu,Fengqin Feng,Yang Li,Wei Wei,Rongrong Lu
Dioleoyl; palmitoyl-rich triacylglycerols (OPO-rich TAG) were synthesized through Aspergillus oryzae lipase (AOL)-catalyzed acidolysis of palm stearin with commercial oleic acid by a one-step process in a stirred tank reactor and continuous packed bed reactor to evaluate the feasibility of using immobilized AOL. AOL was found to be valuable for the synthesis of OPO-rich TAG when compared with commercial lipase from Thermomyces lanuginose (Lipozyme ® TL IM; Novozymes A/S, Bagsvaerd, Denmark). The C52 (triglycerides with a carbon number of 52, stands for OPO, OPL, LPL and their isomers) content of AOL was higher (45.65 %), and the intensity of treatment (IOT: lipase amount × reaction time/TAG amount) of AOL was just 6.25 % of that of Lipozyme ® TL IM under similar reaction conditions in the stirred tank reactor. Response surface methodology were used to optimize the reaction conditions of the AOL-catalyzed acidolysis is reaction in the packed bed reactor. The optimal point for the set of experimental conditions generated were as follows: residence time 3.0 h; temperature 62.09 °C; substrate molar ratio 7.13 mol/mol. The highest C52 content obtained was 48.60 ± 2.36 %, with 57.46 ± 1.72 % total palmitic acid at the sn -2 position and 74.21 ± 2.45 % oleic acid at the sn -1,3 positions. The half-life of AOL was 24 h in the stirred tank reactor and 140 h in the packed bed reactor. The immobilized AOL achieved similar conversion and selectivity to commercial lipases for the catalyzed synthesis of OPO-rich TAG and may offer a cheaper alternative.
研究领域:
生物化学
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食品科学
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酶工程
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DOI
高影响因子
FOOD CHEMISTRY
·
2017
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IF 4.529
Mingming Zheng,Shi Wang,Xia Xiang,Jie Shi,Juan Huang,Qianchun Deng,Fenghong Huang,Junyong Xiao
In this study, Candida lipolytica lipase ( CLL ) was immobilized on magnetic multi-walled carbon nanotubes (mMWCNTs) via hydrophobic and cation-exchange interaction. The resultant immobilized CLL showed much better thermal stability, biocatalyst activity and easier recycling than the free form. A method for efficient enzymatic acidolysis of tripalmitin (PPP) with oleic acid (OA), to produce OPO-rich TAGs, was developed, using the immobilized CLL as the biocatalyst. Under optimized conditions (2% water, 20 mg/ml enzyme, 1:6 PPP/OA, 50 °C, 2 h), the content of OPO in the final product reached 46.5%. CLL @mMWCNTs had a better activity and manipulative stability than commercial lipases. More importantly, the feasibility of CLL @mMWCNTs was also validated in the practical production of OPO-rich TAGs, using lard and restructured palm oil as the raw material. These results suggest that CLL @mMWCNTs is a promising biocatalyst for the OPO-rich TAGs production and will be helpful for the infant formula industry.
研究领域:
生物催化
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食品科学
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酶工程
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产品关联
DOI
PubMed
高影响因子
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.
研究领域:
食品科学
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生物化学
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酶学
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婴幼儿营养
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DOI
PubMed
高影响因子
Food & Function
·
2023
·Vol. 14
·期 16
·7574-7585
·
IF 6.1
Lin Zhu,Shuaizhen Fang,Wenwen Liu,Hong Zhang,Yaqiong Zhang,Zhuohong Xie,Puyu Yang,Jianchun Wan,Boyan Gao,Liangli (Lucy) Yu
In this study, the effect of sn-2 palmitic triacylglycerols (sn-2 palmitic TAGs) and the ratio between the two major sn-2 palmitic TAGs (OPL to OPO ratio) in a human milk fat substitute (HMFS) on growth, fatty acid and calcium absorptions, and lipid and bile acid metabolic alterations was investigated in Sprague-Dawley rats. After 4 weeks of high-fat feeding, rats fed with the HMFS containing a sn-2 palmitic acid content of 57.87% and an OPL to OPO ratio of 1.4 showed the lowest TAG accumulation in their livers and hypertrophy of perirenal adipocytes, compared to the groups fed with fats containing a lower sn-2 palmitic acid content or a lower OPL to OPO ratio. Meanwhile, synergistically improved absorption of fatty acids and calcium and increased levels of total bile acids (BAs), especially for the tauro-conjugated BAs (TCDCA, TUDCA, TαMCA, TβMCA, TDCA and TωMCA), were observed in rats by both increasing the sn-2 palmitic acid content and the OPL to OPO ratio in HMFS. In addition, the levels of total BAs and tauro-conjugated BAs were negatively correlated with serum TAG, TC, and LDL-c levels and positively correlated with HDL-c levels according to Spearman's correlation analysis (P < 0.05). Collectively, these findings present new nutritional evidence for the potential effects of the TAG structure and composition of a human milk fat substitute on the growth and lipid and bile acid metabolism of the host in infancy.
研究领域:
营养学
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分子生物学
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儿科医学
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产品关联
DOI
PubMed
高影响因子
FOOD RESEARCH INTERNATIONAL
·
2023
·
IF 8.1
Dongyin Liu,Jingtao Cui,Ruibing Zhou,Chen He,Jun Cao,Chuan Li
Triacylglycerols (TAG) are differences in fatty acid distributions between infant formula and human milk. In this study, fish oil (Tilapia, Golden pompano, Tiger grouper, and Basa) showed the potential as the source of human milk fat substitutes by comparing TAG profiles with infant formula and human milk. The total lipids and TAG of fish were concentrated in the by-products of fish (head and viscera) and contained high levels of palmitic acid, oleic acid, and linoleic acid. Compared with infant formula, fish oil was closer to human milk in sn -2 fatty acid distribution, and sn -2 palmitic acid level in fish oil exceeded 52 % of total palmitic acid, Golden pompano head was the highest (64.46 %). Further research showed that the content of sn -2 palmitoyl TAG (OPO and OPL dominated) increased from 157.16 mg/g TAG to 305.18 mg/g TAG by isopropanol enrichment (solid–liquid ratio: 1:4, temperature: −12 °C, time: 4 h).
研究领域:
食品科学
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营养学
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生物化学
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产品关联
DOI
PubMed
高影响因子
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY
·
2020
·
IF 4.192
Niu Zhang,Jun-Peng Zeng,Yan-Ping Wu,Meng Wei,Hong Zhang,Liufeng Zheng,Ze-Yuan Deng,Jing Li
The digestion and absorption of different structural lipids in human milk may be different. Hence, by simulating in vitro infant digestion and Caco-2 cells to explore the effects of 1-oleoyl-2-palmitoyl-3-linoleoylglycerol (OPL)/1,3-dilinoleoyl-2-palmitoylglycerol (LPL)/1,3-dioleoyl-2-palmitoylglycerol (OPO) and their mixtures (M) (OPL/LPL/OPO in M1, M2, and M3 were 1.5/0.5/1, 1.2/1.2/1, and 0.5/0.2/1, respectively) on digestion and absorption. The digestibility of the OPO group was higher than those of the OPL and LPL groups, and the M3 group was higher than the M1 and M2 groups. The synthesis and transport of triglycerides in Caco-2 cells in OPL and LPL groups were higher than the OPO group, and the M1 group was significantly higher than that of M3. The expression of FABP1, PPARα, and MTT protein in OPL and M1 groups was significantly higher than OPO and M3, respectively. There are differences in the digestion and absorption of differently structured lipids from this study.
研究领域:
营养学
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生物化学
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儿科
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DOI
PubMed
高影响因子
Nutrients
·
2023
·Vol. 15
·期 23
·4929
·
IF 5.9
Lin Zhu,Shuaizhen Fang,Hong Zhang,Xiangjun Sun,Puyu Yang,Jianchun Wan,Yaqiong Zhang,Weiying Lu,Liangli Yu
In this study, the impact ofsn-2 palmitic triacyclglycerols (TAGs) in combination with their ratio of two major TAGs (1-oleoyl-2-palmitoyl-3-linoleoylglycerol (OPL) to 1,3-dioleoyl-2-palmitoylglycerol (OPO)) in human milk fat substitute (HMFS) on bile acid (BA) metabolism and intestinal microbiota composition was investigated in newly-weaned Sprague–Dawley rats after four weeks of high-fat feeding. Compared to those of control group rats, HMFS-fed rats had significantly increased contents of six hepatic primary BAs (CDCA, αMCA, βMCA, TCDCA, TαMCA and TβMCA), four ileal primary BAs (UDCA, TCA, TCDCA and TUDCA) and three secondary BAs (DCA, LCA and ωMCA), especially for the HMFS with the highestsn-2 palmitic acid TAGs of 57.9% and OPL to OPO ratio of 1.4. Meanwhile, the inhibition of ileal FXR-FGF15 and activation of TGR5-GLP-1 signaling pathways in HMFS-fed rats were accompanied by the increased levels of enzymes involved in BA synthesis (CYP7A1, CYP27A1 and CYP7B1) in the liver and two key thermogenic proteins (PGC1α and UCP1) in perirenal adipose tissue, respectively. Moreover, increasingsn-2 palmitic TAGs and OPL to OPO ratio in HMFS also altered the microbiota composition both on the phylum and genus level in rats, predominantly microbes associated with bile-salt hydrolase activity, short-chain fatty acid production and reduced obesity risk, which suggested a beneficial effect on host microbial ecosystem. These observations provided important nutritional evidence for developing new HMFS products for infants.Keywords:sn-2 palmitic triacylglycerols;human milk fat substitute;BA metabolism;FXR;TGR5;gut microbiota
研究领域:
营养学
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微生物学
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代谢学
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分子生物学
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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）