• Journal of the Korean Society of Food Science and Nutrition
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• v.38 no.11
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• pp.1559-1563
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• 2009

Scaled-up production of oil containing diacylglycerol (DAG), so called diacylglycerol-oil, was produced by lipase-catalyzed reaction. Mixture of soybean oil and glyceryl monooleate with 1:2 molar ratio was esterified with Lipozyme RMIM in a batch-type reactor at 55$^{\circ}C$ and 300 rpm during 6 hr. After short-path distillation for removal of monoacylglycerol and free fatty acid as reaction by-products, diacylglycerol-oil mainly consisted of DAG (29 area%) and TAG (71 area%). The major compositional fatty acids in diacylglycerol-oil were oleic (44.36 wt%), and linoleic acids (37.36 wt%). Acid value and iodine value of diacylglycerol-oil were 0.13 and 112.6, respectively. Solid fat content (SFC) of diacylglycerol-oil was observed after differential scanning calorimetry (DSC) analysis in which three melting peaks at -25.0, 0.1, and 11.2$^{\circ}C$ were shown.

• Korean Journal of Agricultural Science
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• v.41 no.2
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• pp.141-147
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• 2014

Diacylglycerol-oil (DAG oil) and four kinds of fatty acids [C16:0, C18:0, perillar oil-hydrolyzate(C18:3, 59.7%) and docosahexaenoic acid(DHA, C22:6, 63.7%)] were enzymatically esterified with 1:0.5, 1:1 and 1:1.5 molar ratio (DAG oil: fatty acids) to produce structured DAG. The reaction mixture were catalyzed by addition of sn-1,3 specific Lipozyme RMIM with 10 wt% of total substrates, and reacted for 1, 3, 6 and 24 hr at $62^{\circ}C$ with 220 rpm on the shaking water bath. The produced DAG were analyzed by TLC. In the result, the proportion of each fatty acid [(C16:0, C18:0, perilla oil-hydrolysate(C18:3, 59.7%) and DHA(C22:6, 63.7%)] on DAG products were increased as molar ratios of substrate increased. Among them, DHA showed the least reaction rate in which 24.2 % of DHA was found in the structured DAG molecules after 24 hr reaction with 1:1.5 molar substrate amount ratio.

• Korean Journal of Food Science and Technology
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• v.42 no.2
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• pp.246-249
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• 2010

Diacylglycerol (DAG) was produced from lipase by the catalyzed synthesis of soybean oil (SBO) and glyceryl monooleate (GMO) with Lipozyme TLIM (Thermomyces lanuginosa). Effects of reaction time, molar ratio and enzyme road were studied. When 2:1, 1:1 and 1:2 (SBO:GMO) molar ratios with 20% Lipozyme TLIM were applied in a 1-hr reaction, the concentrations of DAG produced were 17.8, 20.0 and 20.4 g/100 g oil, respectively. Different amounts (2, 5, 10 and 20%) of Lipozyme TLIM were used at a 1:2 (SBO:GMO) molar ratio, and the concentrations of DAG produced in a 1-hr reaction were 10.8, 14.0, 16.9 and 20.4 g/100 g oil, respectively. During a 72-hr reaction, 10.8-22.7 g/100 g oil of DAG were produced under the reaction conditions in this study.

• Korean Journal of Agricultural Science
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• v.41 no.1
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• pp.47-58
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• 2014

The effect of conjugated linoleic acid (CLA) isomers esterified in diacylglycerol (DAG)-rich oil on lipid metabolism was investigated. Since dietary DAG has been known to induce the regression of atherosclerosis, CLA-DAG and olive-DAG oils containing similar levels of DAG (51.4~54.2%) were synthesized from olive oil. Hyperlipidemic C57BL/6J mice were then fed high-fat high-cholesterol diets supplemented with these oils (5% each) for 7 wk. The CLA-DAG diet containing 2.1% CLA isomers (0.78% c9,t11-CLA; 1.18% t10,c12-CLA) remarkably increased the levels of total plasma cholesterol and glutamic oxaloacetic transaminase (GOT) along with hepatic cholesterol and triacylglycerol (TAG) contents. Furthermore, the CLA-DAG diet inhibited fat uptake into adipose tissue whereas fat deposition (especially in the liver) was increased, resulting in the development of fatty livers. Hepatic fatty acid composition in the CLA-DAG mice was different from that of the olive-DAG mice, showing higher ratios of C16:1/C16:0 and C18:1/C18:0 in the liver. The activity of hepatic acyl-CoA:cholesterol acyltransferase (ACAT) was higher in CLA-DAG mice while plasma lecithin:cholesterol acyltransferase (LCAT) activity and the ferric reducing ability of plasma (FRAP) were lower in CLA-DAG mice compared to the olive-DAG animals. Results of the present study suggest that CLA incorporation into DAG oil could induce atherosclerosis in mice.

• Korean Journal of Food Science and Technology
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• v.36 no.2
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• pp.211-216
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• 2004

Mono-and diacylglycerol-enriched oil was produced from corn oil through enzymatic glycerolysis using 1,3-specific immobilized lipase in solvent-free system and stirred-tank batch reactor. HPLC analysis revealed enriched oil was respectively composed of: 45.05, 16.27, 23.05, and 14.98% triacylglycerol, 1,3-diacylglycerol, 1,2-diacylglycerol, and monoacylglycerol; 13.21, 0.15, 2.02, 34.36, 49.12, and 1.14 mol% palmitic, palmitoleic, stearic, oleic, linoleic, and linolenic acids; and 0.014, 0.029, 0.010 and 0.053% ${\alpha},\;{\gamma},\;{\delta}-$, and total tocopherols. Physiochemical and melting properties of enriched oil were evaluated. Oxidative stability study revealed enriched oil showed higher peroxide and p-anisidine values than corn oil. Rosemary extracts (100 to 300 ppm) reduce oxidation.

• Food Science and Preservation
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• v.16 no.2
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• pp.246-252
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• 2009

Diacylglycerol(DAG) was produced by enzymatic esterification of glyceryl mono-oleate(GMO) and conjugated linoleic acid(CLA) in a stirred-batch type reactor. The reaction was catalyzed by lipozyme RMIM(an immobilized lipase from Rizomucor miehei). DAG was isolated by a short-path distillation process and decolorized. DAG oil was composed of 87.3% DAG, 11.4% triacylglycerol(TAG), and 1.5% monoacylglycerol(MAG)(all w/w). Major fatty acids in DAG oil were oleic acid(54%), CLA(31.1%), and linoleic acid(7%). DAG oil iodine,and acid values were 108.8, 2.57, and 1, respectively. The DAG oil solid fat index(SFI) and thermograms were obtained using differential scanning calorimetry.

• Journal of Nutrition and Health
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• v.31 no.1
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• pp.21-27
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• 1998

The objective of this study was to observe the effect of dietary calcium(Ca) level on colonic mucosal levels of cell proliferation, 1, 2-diacylglycerol(DAG), TXB2, PGE2 and phospholipid fatty acid composition which have been known as biomarkers for colon cancer. One hundred male Sprague Dawley rats, at 7 weeks of age, were divided into two fat type groups. Each group of which was further divided into two Ca level groups. Each rt was intramuscularly injected with 1, 2,-dimenthylhydrazine(DMH) for 6 weeks (total dose of 180mg/kg body weight) and simultaneously fed one of four experimental diets containing 15% dietary fat(corn oil or perilla oil )and 0.3% or 1.0% Ca by weight for 20 weeks. Compared to corn oil, perilla oil significantly reduced cell proliferation by decreasing labeling index, proliferating zone, crypt length in colonic mucosa and colonic mucosa and colonic mucosal levels of DAG, TXB2 . PGE2 and phospolipid (PL) arachidonic acid distribution. The effect of Ca on biomarketrs was different depending on the type of dietary fat comsumed . Ca effect of Ca on biomarkers was different depending on the type of dietary fat comsumed. Ca effect was not significantly shown in the PO group, but it was significant in the CO group in which high Ca(1.0%) decreased the levels of levels of PL-C20 : 4(%), DAG and PGE2 . However , high Ca supplementation had shown only the trends of improving cell proliferation. Overall , high dietary Ca significantly reduced cell proliferation by inhibiting the synthesis of eicosanoid and DAG with reduced distribution of PL-C20 : 4 , which may have resulted in lower activation of PKC through reduced signal transduction. Since a high level of dietary Ca was more effective in reducing the risk factor against colon cancer in corn oil fed rats, it could be suggested that a higher amount of dietary Ca be consumed , especially when more vegetable oil rich in linoleic acid is included in the diet.

• Korean Journal of Food Science and Technology
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• v.51 no.3
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• pp.272-277
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• 2019

The effects of medium-chain enriched diacylglycerol (MCE-DAG) oil on hepatic cholesterol homeostasis were investigated. HepG2 hepatocytes were treated with either 0.5, 1.0, or $1.5{\mu}g/mL$ of MCE-DAG for 48 h. There was no evidence of cytotoxicity by MCE-DAG up to $1.5{\mu}g/mL$. The level of proteins for cholesterol uptake including CLATHRIN and LDL receptor increased by MCE-DAG in a dose-dependent manner (p<0.05). Furthermore, proprotein convertase subtilisin/kexin type 9, an inhibitor of LDLR, was dose-dependently diminished (p<0.05), indicating cholesterol clearance raised. MCE-DAG significantly increased 3-hydroxy-3-methylglutaryl-coenzyme A reductase and acetyl-CoA acetyltransferase2 (p<0.05), required for cholesterol synthesis, and their transcriptional regulator sterol regulatory element-binding protein2 (p<0.05). These findings suggest that given conditions of prolonged sterol fasting in the current study activated both hepatic cholesterol synthesis and clearance by MCE-DAG. However, total intracellular level of cholesterol was not altered by MCE-DAG. Taken together, MCE-DAG has the potential to prevent hypercholesterolemia by increasing hepatic cholesterol uptake without affecting intracellular cholesterol level.

• Food Science of Animal Resources
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• v.37 no.6
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• pp.813-822
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• 2017

The aim of this study was to prepare diacylglycerol (DAG) by enzymatic glycerolysis of lard. The effects of reaction parameters such as lipase type, reaction temperature, enzyme amount, substrate molar ratio (lard/glycerol), reaction time, and magnetic stirring speed were investigated. Lipozyme RMIM was found to be a more active biocatalyst than Novozym 435, and the optimal reaction conditions were 14:100 (W/W) of enzyme to lard substrate ratio, 1:1 of lard to glycerol molar ratio, and 500 rpm magnetic stirring speed. The reaction mixture was first incubated at $65^{\circ}C$ for 2 h and then transferred to $45^{\circ}C$ for 8 h. At the optimum reaction conditions, the conversion rate of triacylglycerol (TAG) and the content of DAG in the reaction mixture reached 76.26% and 61.76%, respectively, and the DAG content in purified glycerolized lard was 82.03% by molecular distillation. The distribution of fatty acids and Fourier transform infrared spectra in glycerolized lard samples were similar to those in lard samples. The results revealed that enzymatic glycerolysis and molecular distillation can be used to prepare more highly purified DAG from lard.

• Journal of the Korean Society of Food Science and Nutrition
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• v.38 no.8
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• pp.1062-1068
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• 2009

Diacylglycerol (DAG) were synthesized by enzymatic esterification of glyceryl monooleate (GMO) and conjugated linoleic acid (CLA) in a shaking water bath. The reaction was catalyzed by Lipozyme TLIM (immobilized lipase from Thermomyces lanuginosa). Effects of reaction time, molar ratio, enzyme road and molecular sieves were studied. Results of normal-phase high performance liquid chromatography (NP-HPLC) analysis were performed. At 1:1, 2:1 and 3:1 (GMO : CLA) molar ratio and Lipozyme TLIM of 20% amount, DAG were produced in 42.6, 54.4 and 54.6 area% in 1 hr, respectively. When different Lipozyme TLIM amounts (2, 5, 10, 20%) were used with 2:1 (GMO : CLA) molar ratio, DAG were produced 21.4 (24 hr), 51.7 (12 hr), 56.2 (6 hr) and 54.4 (1 hr) area%, respectively. The reaction in the absence of molecular sieves increased DAG contents. The maximum DAG concentration conditions were obtained with molar ratio of 2:1 (GMO : CLA), lipase concentration of 10% (of substrate), 10% molecular sieves and reaction time of 6 hours at 55$^{\circ}C$. Under this reaction condition, produced DAG-rich oil was composed of 69 area% DAG, 7.9 area% TAG, 2 area% FFA, and 21.1 area% MAG.