• Journal of the Korean Society of Food Science and Nutrition
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• v.39 no.8
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• pp.1156-1164
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• 2010

Structured lipids (SLs) were synthesized by enzymatic interesterification with evening primrose oil (EPO) and rice bran oil (RBO) in a batch-type reactor. The interesterification was performed using a water shaker for 24 hr at $55^{\circ}C$. Mixing speed was set at 200 rpm and Lipozyme RM IM (immobilized lipase from Rhizomucor miehei, 10% by weight of total substrates) was used as a biocatalyst. Rice bran oil and evening primrose oil were interesterified with various molar ratios (RBO : EPO, 1:3, 1:4, and 1:5 mol/mol). Reversed-phase high performance liquid chromatography connected with evaporative light-scattering detector was performed to separate the triacylglycerol (TAG) species of SLs. In the fatty acid analysis, $\gamma$-linolenic acid (7.9 mol%), linoleic acid (67.3 mol%) and oleic acid (13.2 mol%) were the most abundant fatty acids in the SLs. During 24 hr reaction, most of the reaction occurred within 3 hr. TAG compositions, tocopherols and phytosterols were also analyzed. In the TAG species analysis, LLL (ECN=42, L=linoleic acid) dramatically decreased when the reaction time increased.

• Korean Journal of Food Science and Technology
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• v.43 no.6
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• pp.689-695
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• 2011

1,3-Dioleoyl-2-palmitoylglycerol (OPO)-rich human milk fat substitute (HMFS) was synthesized from tripalmitin (PPP)-rich fraction and oleic ethyl ester by a lipase-catalyzed interesterification. Response surface methodology (RSM) was employed to optimize the presence of palmitic acid at sn-2 position ($Y_1$, %) and of oleic acid at sn-1,3 ($Y_2$, %), with the reaction factors as substrate molar ratio of PPP-rich fraction to oleic ethyl ester ($X_1$, 1:4, 1:5 and 1:6), reaction temperature ($X_2$, 50, 55 and $60^{\circ}C$), and time ($X_3$, 3, 7.5 and 12 h). The optimal conditions for HMFS synthesis were predicted at the reaction combination of $55^{\circ}C$, 3 h and 1:6 substrate ratio. HMFS re-synthesized under the same conditions displayed 70.70% palmitic acid at the sn-2 position and 69.58% oleic acid at the sn-1,3 position. Reaction product was predominantly (90.35%) triacylglycerol (TAG) was observed in which the major TAG species, OPO, comprised 31.24%.

• Food Science and Preservation
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• v.15 no.3
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• pp.437-444
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• 2008

Structured lipids(SLs) were synthesized by enzymatic interesterification with DHA-enriched fish oil(containing 27% docosahexaenoic acid) and soybean oil in the hatch-type reactor. The interesterification was performed for 24 hr at $55^{\circ}C$ and TLIM(immobilized lipase from Thermonyces lanuginosa, 10% by weight of total substrates) was mixed with 180 rpm of shaking. The fish oil and soybean oil were interesterifed with several weight ratio(fish oil : soybean oil, 2:8, 3:7, 4:6, 5:5, w:w), Reverse-phase high performance liquid chromatography with an evaporative light-scattering detector separated the triglyceride species of SLs. The products contained the newly synthesized peaks. Especially, one of peaks was distinctively increased with the increasing weight ratio from 2:8 to 5:5 while the peak of trilinolein (LLL) decreased vice versa. The effect of antioxidants such as catechin, BHT(Butylated hydroxytoluene), and their combinations on the oxidative stability in SL were investigated. Oxidative stability was carried out under oven test at $60^{\circ}C$ over 72 hr thereafter SLs were analyzed for total fatty acid content, rancimat, peroxide value, electronic nose and TBARS value. Among all combinations of antioxidant, the highest stability was obtained from 200 ppm of catechin. Besides, total tocopherol ($\alpha$, $\gamma$, and $\delta$-tocopherol), iodine and saponification value were analyzed in which iodine and saponification value of SLs were 151.19 and 182.35.

• Food Science and Preservation
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• v.10 no.3
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• pp.370-375
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• 2003

To obtain the oil sesame, walnut, whole wheat, and rice bran were extracted for 1, 3, or 6 hr by a shanking water bath(35$^{\circ}C$ and 100 rpm), and by soxhlet extractor(80$^{\circ}C$) for 1, 3 or 6 hr, respectively. The highest yield of extracted oil was obtained from the walnut(63.07％ weight) and the whole wheat showed the lowest extraction yield of oil(1.13％ weight). Major fatty acids from the extracted oils were linoleic, oleic, and palmitic acid. The maximum contents of total phytosterol in sesame, walnut, whole wheat, and rice bran were 0.44, 1.57, 2.25, and 2.03(％ weight), respectively. Besides, total tocopherol contents in sesame, walnut, whole wheat, and rice bran were maxima 3.42, 0.16, 2.92, and 0.07(％ weight), respectively. From the extracted oils, structured lipids(SL) were synthesized by the interesterification reaction with conjugated linoleic acid(CLA) in a shanking water bath at 55$^{\circ}C$. When the reactions(1:3 substrate molar ratio, extracted oil:CLA) were conducted for 24 hr, maxima 23.75 mol％ of CLA incorporation was obtained from walnut oil and, in other cases, 16.28 - 19.15 mol％ of CLA was found in the produced SL triacylglycerol molecules.

• Journal of Microbiology and Biotechnology
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• v.27 no.9
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• pp.1617-1627
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• 2017

Dietary approaches using structured lipids, including medium-chain fatty acids and diacylglycerols, have been adopted for the prevention of obesity-induced chronic inflammation. In an extension to previous studies, medium-chain fatty acid-diacylglycerol enriched dietary oil (MCDG) was prepared by interesterification of canola oil and medium-chain fatty acid-triacylglycerols. The consequent MCDG product was applied to RAW264.7 macrophages followed by the assessment of multiple inflammatory responses. Compared with conventionally used canola and olive oil controls, MCDG suppressed macrophage phagocytosis, as assessed by the uptake of microsphere beads. Furthermore, the production of IL-6 and $TNF-{\alpha}$, transcription of COX-2 and iNOS, and expression of CD80 on cell surfaces were downregulated by MCDG in LPS-stimulated macrophages. Subsequently, differentiated 3T3-L1 adipocytes were evaluated for proinflammatory cytokine production and lipid accumulation. IL-6 production was marginally affected and lipid accumulation was inhibited by MCDG. Taken together, these results suggest that MCDG has potential as an alternative oil for cooking in order to prevent obesity-induced inflammation.

• Korean Journal of Food Science and Technology
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• v.24 no.3
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• pp.251-255
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• 1992

Lard was randomly interesterified to improve handling efficiency with increase of plasticity, and it's physicochemical properties and adaptability for making pie were investigated. Fatty acid and triacylglycerol composition were not changed after interesterification. Interesterified lard could be useful during winter because the handling was convenient due to drop in the temperature range of $18{\sim}23.5^{\circ}C$ in lard and $13{\sim}19.5^{\circ}C$ in interesterified lard with SFI $15{\sim}25$. Interesterified lard was decreased in the extensibility by change of crystal form, and not suitable for making pie as the inferior characters for layers forming, appearance and shortness. But interesterified lard mixed with plastic fat of high extensibility showed the possibility of making pie, and the maximum mixture ratio was 50% for good pie quality.

• Microbiology and Biotechnology Letters
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• v.15 no.2
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• pp.122-128
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• 1987

Lipases from Candida rogosa and Rhizopus arrhizus were immobilized by entrapment with photo-crosslinkable resin prepolymer for the study of fat splitting and interesterification in isooctane-two phase system. Dioctylsulfosuccinate was selected as the most suitable surfactant during the immobilization. Lipase entrapped with hydrophobic photo-crosslinkable resin prepolymer(ENTP-3000) exhibited the highest activity, whereas lipase entrapped with hydrophilic gel(ENT-4000) was more stable in organic solvent. As the degree of hydrophobicity of the immobilization matrix was increased, Vm(app) of the lipase entrapped was increased, but Km(app) was approximately constant. While the optimum pH of the lipases entrapped on hydrophilic gel (ENT-4000) were around pH 7.0 for Candida lipase and Rhizopus lipase, the reaction rate of the lipases entrapped on hydrophobic gel were less dependent on pH variations for short reaction time. However, for longer reaction time, the lipnses from C. rugosa and R. arrhizus entrapped on hydrophobic gel yielded maximum rate at pH 6.0 and 6.5, respectively, Entrapment method endowed the lipase with thermal stability.

• Journal of the Korean Society of Food Science and Nutrition
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• v.39 no.9
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• pp.1328-1334
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• 2010

Low-trans spread fat (LTSF) was produced by lipase-catalyzed synthesis of canola (CO) and fully hydrogenated soybean oil (FHSBO) at 65:35 (w/w). Blend of CO and FHSBO with 65:35 ratio was interesterified using Lipozyme TLIM (immobilized Thermomyces lanuginosus, 20% of total substrate) in a 1 L-batch type reactor at $70^{\circ}C$ with 500 rpm for 24 hr. Then, physicochemical melting properties of LTSF were compared with commercial spread fat. At $20^{\circ}C$, solid fat contents (SFC) of commercial spread fat as a control and LTSF were similar, showing 19.1 and 18.1%, respectively. Major compositional fatty acids of LTSF were C18:0, C18:1 and C18:2 (29.2, 41.8 and 13.3 wt%, respectively). Trans fatty acid content of the LTSF (0.2 wt%) was lower than that of commercial spread fat (5.5 wt%). In the RP-HPLC analysis from LTSF, major triacylglycerol (TAG) molecules were SOL (stearoyl-oleoyl-linoleyl), SOO, POS/PSP, and SOS. Also, polymorphic form and x-ray diffraction of LTSF showed coexistence of $\beta$' and $\beta$ form crystals.

• Journal of Mushroom
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• v.13 no.1
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• pp.56-62
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• 2015

A lipase producing bacterium was isolated from button mushroom bed, which showing high clear zone on agar media containing Tributyrin as the substrate. The strain was identified as Burkholderia cepacia by analysis of 16S rDNA gene sequence. Crude lipase (CL) was partially purified from 70% ammonium sulfate precipitation using the culture filtrate of B. cepacia. Immobilized lipases were prepared by cross-linking method with CL from B. cepacia and Novozyme lipase (NL) onto silanized Silica-gel as support. Residual activitiy of the immobilized CL (ICL) and immobilized NL (INL) was maintained upto 61% and 72%, respectively. Biodiesel (Fatty acid methyl ester, FAME) was recovered by transesterification and methanolysis of Canola oil using NaOH, CL and ICL as the catalysts to compare the composition of fatty acids and the yield of FAME. Total FAME content was NaOH $781mg\;L^{-1}$, CL $681mg\;L^{-1}$ and ICL $596mg\;L^{-1}$, in which the highest levels of FAME was observed to 50% oleic acid (C18:1) and 22% stearic acid (C18:0). In addition, the unsaturated FAME (C18:1, C18:2) decreased, while saturated FAME (C16:0, C18:0) increased according to increasing the reaction times with both CL and ICL, supporting CL possess both transesterification and interesterification activity. When reusability of ICL and INL was estimated by using the continuous reaction of 4 cycles, the activity of ICL and INL was respectively maintained 66% and 79% until the fourth reaction.

• Journal of the Korean Society of Food Science and Nutrition
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• v.43 no.6
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• pp.842-853
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• 2014

For developing indigestible lipids, symmetric triacylglycerol (ST) and asymmetric triacylglycerol (AT) were produced by enzymatic interesterification using high oleic sunflower oil, palmitic ethyl ester, and stearic ethyl ester in a shaking water bath. Used enzymes were Lipozyme RMIM for ST and Lipozyme TLIM for AT. To remove ethyl ester from reactants, methanol fractionation (reactant : methanol=1:5, w/v, $25^{\circ}C$) and florisil separation (reactant : florisil=1:8, w/w) were applied. Acetone fractionation (reactant : acetone=1:9, w/v) was implemented to separate triacylglcerol (TAG) species into ST and AT. Fractions I (before fractionation), II (after fractionation, liquid phase) and III (after fractionation, solid phase) were separated from ST, whereas fractions IV (after 1st fractionation, liquid phase) and V (after 2nd fractionation, solid phase) were from AT. From sn-2 fatty acid composition analysis, the sum of palmitic acid (C16:0) and stearic acid (C18:0) was 4.9~6.5 area% in ST (I, II, III), and 41.9~43.9 area% in AT (IV, V). In vitro digestion was performed for 0, 15, 30, 60, and 120 minutes at $37^{\circ}C$ in a shaking water bath. For the digestion results, hydrolysis of V was only 40% compared to others (I, II, III, IV) at 120 minutes due to its melting point ($49^{\circ}C$). However, initially (15 minutes), hydrolysis (%) was as follows: V$32.5^{\circ}C$, $31.8^{\circ}C$) and different slip melting points ($31.3^{\circ}C$, $19.5^{\circ}C$). Even though IV has a lower TAG content composed of two saturated fatty acids than III, it had a similar melting point.