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
·
化学工程
·
生物技术
✓ 已验证
产品关联
DOI
PubMed
高影响因子
LWT-FOOD SCIENCE AND TECHNOLOGY
·
2023
·
IF 6
Yujie Chen,Ruhui Liu,Jingyan Li,Yanjie Wang,Chunfeng Guo,Xin Lü
1-Oleoyl-2-palmitoyl-3-linoleoylglycerol (OPL) is the most abundant triacylglycerol (TAG) molecule in Chinese human milk. The selectivity of three lipases including Rhizomucor miehei lipase (RML), Thermomyces lanuginose lipase (TL), and Candida antarctica lipase (CALB) in OPL synthesis were evaluated. The effects of different reaction conditions on selectivity were first investigated. Unexpectedly, the three sn -1,3 regioselectivity lipases, also have selectivity for the structure of product TAGs. Compared with symmetric TAGs, lipases had poor selectivity toward asymmetric OPL. Furthermore, molecular simulations were used to deeply understand the molecular factors affecting lipase selectivity. The results showed that hydrophobic interactions, lipases lid domain flexibility, and the stability of hydrogen bonds between lipases and TAGs were the main molecular factors responsible for the selectivity of lipases.
研究领域:
生物化学
·
食品科学
✓ 已验证
产品关联
DOI
高影响因子
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
✓ 已验证
DOI
高影响因子
Food & Function
·
2023
·Vol. 14
·期 9
·4092-4105
·
IF 6.1
Meng Kang,Konglong Feng,Weijie Dai,Jianyin Miao,Guo Liu,Huaiyi Fang,Yong Cao
1-Oleoyl-2-palmitoyl-3-linoleoylglycerol (OPL), a key structural lipid in the breast milk fat, plays a critical role in providing nutrients and energy for infants. OPL is more abundant in Chinese breast milk fat and might be better for Chinese infants’ growth. However, few studies have investigated the effect of OPL on the growth and intestinal health of the organism in early life. OPL-rich oil with 45.77% OPL was prepared by immobilized lipase-catalyzed synthesis and purification. The effects of OPL on the nutritional properties and the regulation of intestinal microbiota in early life were further investigated in vivo (Micropterus salmoides). Dietary OPL-rich oil significantly increased the juvenile fish weight gain rate, protein content, and muscular polyunsaturated fatty acids, which in turn markedly altered the muscle texture in springiness and cohesiveness. Dietary OPL-rich oil could also protect intestinal tissues by significantly increasing fish intestinal fold height, mucosal thickness, and intestinal wall thickness. Furthermore, dietary OPL-rich oil regulated intestinal microbiota. Particularly, OPL significantly increased the probiotics (Cetobacterium_sp014250685, Streptomyces_mutabilis, Saccharopolyspora_spinosa, and Nocardiopsis_kunsanensis) and reduced the potential pathogens (Staphylococcus_nepalensis, Salmonella_enterica, the Candidatus_berkiella). The structured OPL significantly promoted fish growth and improved nutritional composition due to its higher bioavailability relative to tripalmitate (PPP). Moreover, OPL significantly improved the growth, cholesterol metabolism, and intestinal health than the mixed oil (MO), which was attributed to the higher palmitic acid content in the sn-2 position. Overall, the structure of triacylglycerols and its distribution of fatty acids affected early growth and intestinal health, and OPL was more effective in the improvement of juvenile growth and intestinal health.
研究领域:
营养学
·
微生物学
·
水产养殖学
✓ 已验证
产品关联
DOI
PubMed
高影响因子
LWT-FOOD SCIENCE AND TECHNOLOGY
·
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
·
生物化学
✓ 已验证
产品关联
DOI
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
·
营养学
·
生物化学
✓ 已验证
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
·
生物化学
·
酶学
·
婴幼儿营养
✓ 已验证
产品关联
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
·
分子生物学
·
儿科医学
✓ 已验证
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
·
生物化学
·
儿科
✓ 已验证
产品关联
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
·
微生物学
·
代谢学
·
分子生物学
✓ 已验证
DOI
PubMed
高影响因子
ACS Sustainable Chemistry & Engineering
·
2024
·
IF 7.1
Zeqing Liu,Lingmei Dai,Dehua Liu,Wei Du
Single-crystalline ordered macro–microporous CuBTC (SOM–CuBTC) is a promising carrier for lipase immobilization due to enhanced mass transfer and stability toward fatty acids. However, the low yield per mass of the template during the preparation process and the water instability of the SOM–CuBTC carrier have posed significant limitations on its practical applications. In this study, we addressed these challenges by introducing a novel dual-solvent system consisting of dimethyl sulfoxide (DMSO) and ethanol to obtain a stable precursor solution with a concentration approximately 10 times higher than that in previous literature, yielding 21.4 mg of SOM–CuBTC per gram of the polystyrene template. However, the decomposition of SOM–CuBTC in an aqueous system of lipase immobilization was observed. We explored chemical vapor deposition and sol–gel methods for hydrophobic modification on SOM–CuBTC. SOM–CuBTC coated by hydrophobic polydimethylsiloxane (PDMS) via the sol–gel method possessed excellent chemical stability and exhibited great potential for lipase immobilization with a significant increase by 98.7% in the specific activity. The obtained immobilized lipase not only showed improved thermal stability and pH tolerance but also displayed excellent catalytic performance in the synthesis process of 1-oleoyl-2-palmitoyl-3-linoleoylglycerol (OPL) by acidolysis. This work reveals the great potential of SOM–CuBTC and provides new insights into the rational design of metal–organic frameworks for enzyme immobilization in extensive applications.
研究领域:
材料科学
·
酶工程
·
生物催化
·
化学工程
✓ 已验证
产品关联
DOI
高影响因子
FOOD RESEARCH INTERNATIONAL
·
2024
·
IF 7
Fang Wu,Yaqiong Liu,Ming Zhang,Xinlei Yuan,Tengteng Ji,Yutong Jin,Yixuan Li,Ran Wang,Yanling Hao,Bing Fang
Recent studies have shown that 1-oleo-2-palmito-3-linoleyl glycerol (OPL) is the most abundant triacylglycerol in human breast milk in China. Epidemiologic studies have shown that sn -2 palmitate improves the absorption of fatty acids and calcium in infants. However, there have been few studies of the specific mechanism by which OPL affects intestinal function. In the present study, we have characterized the effects of various levels of OPL supplementation on the development of the intestinal epithelium and the intestinal microbiota of neonatal mice. OPL supplementation increased the body masses and intestinal lengths of weaned mice and promoted defecation. These positive effects were related to the effect of OPL to promote the development of intestinal villi and crypts. OPL increased the expression of the intestinal stem cell markers Olfm4 and Sox9 in the jejunum and ileum, which promoted their differentiation into goblet cells and Paneth cells. It also promoted the integrity of the epithelial barrier by increasing the secretion of mucin 2 and lysozyme 1 and the expression of the tight junction proteins occludin, ZO1, claudin 2, and claudin 3. More importantly, we found that low dose-OPL promotes the transformation of the intestinal microbiota of neonatal mice to the mature state in 3-month-old mice, increases the proportion of Firmicutes, and reduces the proportion of Bacteroidota. The proportions of anaerobic genera of bacteria, such as Lachnospiraceae_NK4A136_group, Lachnoclostridium, Ligilactobacillus, and Bifidobacterium were higher, as were the key producers of short-chain fatty acids, such as Bacteroides and Blautia . OPL also increased the butyric acid content of the feces, which significantly correlated with the abundance of Lactobacillus . High-dose OPL tended to be more effective at promoting defecation and the development of the villi and crypts, but these effects did not significantly differ from those achieved using the lower dose. A low dose of OPL was more effective at increasing the butyric acid content and causing the maturation of microbes. In summary, the OPL supplementation of newborn mice promotes the establishment of the intestinal epithelial layer structure and barrier function, and also promotes the transformation of the intestinal microbiota to a mature state. This study lays a theoretical foundation for the inclusion of OPL in infant formula and provides a scientific basis for the development of intestinal health products.
研究领域:
营养学
·
胃肠病学
·
微生物学
·
发育生物学
✓ 已验证
产品关联
DOI
PubMed
高影响因子
危险品化学品经营许可证（带存储）