• 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.18 no.5
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• pp.721-728
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• 2011

1(3)-palmitoyl-2-oleoyl-3(1)-stearoyl-(POS)-glycerol-enriched reaction products were synthesized from camellia oil, palmitic ethyl ester, and stearic ethyl ester via lipase-catalyzed interesterification. Response surface methodology (RSM) was employed to optimize the production of the POS-enriched reaction product (Y1, %) and the stearicand palmitic-acid contents at the sn-2 position due to acyl migration (Y2, %). The reaction factors were the enzyme amount (X1, 2-6%), reaction time (X2, 60-360 min), and substrate molar ratio of camellia oil to palmitic ethyl ester and stearic ethyl ester (X3, 1-3 mol). The predictive models for Y1 and Y2 were adequate and reproducible as no lack of fit was signified (0.128 and 0.237) and as there were satisfactory levels of R2 (0.968 and 0.990, respectively). The optimal conditions for the reaction product for maximizing Y1 while minimizing Y2 were predicted at the reaction combination of 5.86% enzyme amount, 60 min reaction time, and 1:3 substrate molar ratio (3 moles of palmitic ethyl ester and 3 moles of stearic ethyl ester). Actual reaction was performed under the same conditions as above, and the resulting product contained 20.19% TAG-P/O/S and 12.71% saturated fatty acids at the sn-2 position.

• Journal of the Korean Chemical Society
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• v.35 no.1
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• pp.85-89
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• 1991

Various sterols and uncommon fatty acids have been isolated from the three species of Korean marine sponges. Odd-numbered pentadecanoic, heptadecanoic methyl ester and branched 12-methyltetradecanoic, 14-methylpentadecanoic, 15-methylhexadecanoic and 14-methylhexadecanoic methyl ester were isolated along with common tetradecanoic and hexadecanoic methyl ester from Heteropiidae sponge Vosmaeropsis japonica Hozawa collected from Sohuksan island of the Korea sea. Futher elution with more polar solvent gave 5${\alpha}$-cholestan-3${\beta}$-ol along with minor amount of ergost-25-ene-3${\beta}$,5${\alpha}$,6${\beta}$-triol. On the other hand, marine sponge Hymeniacidon sinapium collected from Yesu Dolsan island of the Korea sea was shown to contain 5${\alpha}$-cholestan-3${\beta}$-ol, along with minor amount of cholesterol, palmitic, palmitoleic, oleic, stearic, linolenic, and arachidonic acid ethyl ester. Unknown marin sponge collected from the same region was shown to contain large amount of tetradecanoic tetradecyl and hexadecyl ester and cholesteryl acetic and fatty acid ester.

• 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.

• Journal of the Korean Society of Food Science and Nutrition
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• v.40 no.8
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• pp.1113-1120
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• 2011

Enzymatic interesterification was conducted with the palm mid fraction (PMF) and stearic ethyl ester for 1, 5, and 9 hr at 46$^{\circ}C$. The reaction was catalyzed by Lipozyme TLIM (2, 3, and 4% by weight of total substrates) in a shaking water bath at 180 rpm. As the reaction continued, oleic acid (C18:1) content at the sn-2 position decreased, whereas saturated fatty acid (C16:0 and C18:0) content increased. In the high performance chromatography analysis, 1,3-dipalmitoyl-2-oleoyl glycerol content decreased, whereas 1(3)-palmitoyl-2-oleoyl-3(1)-stearoyl glycerol (POS) content increased up to the reaction equilibrium. The rate of acyl migration increased with increasing molar ratio and enzyme load as well as reaction time. The optimal reaction conditions for maximizing POS content (53.5 area%) and minimizing acyl migration (23.1 area%) were obtained with a PMF : stearic ethyl ester=1:2 (molar ratio), Lipozyme TLIM 3 wt%, and a reaction time of 5 hr.

• Journal of the Korean Society of Food Science and Nutrition
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• v.43 no.1
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• pp.93-101
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• 2014

Asymmetric 1,2-distearoyl-3-oleoyl-rac-glycerol (SSO) triacylglycerol (TAG) is used as a cocoa butter replacer (CBR). In this study, it was produced by lipase-catalyzed interesterification of fully hydrogenated soybean oil (FHSBO) and oleic ethyl ester (OEE) in a batch type reactor at $75^{\circ}C$, 250 rpm. Different molar ratios (FHSBO : OEE=1:1, 1:2 and 1:3, w/w) and various reaction times (1, 2, 3, 4, and 5 hr) were also tested. The optimized condition for SSO was a FHSBO : OEE molar ratio of =1:1 at reaction times of 2, 3, 4, and 5 hr. Enzymatic synthesis generated SSO/SOS, as well as the other TAGs (e.g., PSO/POS, SOO/OSO, SSS), ethyl esters, monoacylglycerol (MAG), and diacylglycerol (DAG). After scale-up, fractionation by solvent (methanol and acetone) fractionation and column chromatography was applied. To reduce ethyl esters, high-melting TAGs (e.g., SSS), and SOO/OSO in reactants, solvent fractionation was applied. Using a silica gel column (sample : silica gel=2:1, wt%), MAG and DAG were removed at $25^{\circ}C$. The major fatty acid composition of the final products (with a high SSO/SOS content) was palmitic acid (C16:0, 10.9~12.9 area%), stearic acid (C18:0, 52.2~54.9 area%), and oleic acid (C18:1, 34.2~35.5 area%). In reversed-phase HPLC analysis, the major TAG species of the final product (FHSBO : OEE=1:1, 2 hr) were SSO/SOS (82.31 area%) and PSO/POS (14.51 area%). Based on the $[SS]^+$ : $[SO]^+$ ratio obtained by RP-HPLC/APCI-MS, the final product had a higher SSO (AAB type TAG) content than cocoa butter (CB). The solid fat index (SFI) of CB and the final product obtained were similar with a narrow melting point range around ~32 to $35^{\circ}C$.

• Preventive Nutrition and Food Science
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• v.17 no.4
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• pp.310-314
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• 2012

Thirty-two different volatile oils were identified from Allomyrina dichotoma (A. dichotoma) larvae by gas chromatography/mass spectrometry (GC/MS). The major volatile components were 2,2,4-trimethyl-3-carboxyisopropyl pentanoic acid isobutyl ester (5.83%), phenol,2,6-bis(a,a-dimethyl ethyl)-4-(1-methyl-1-phenylethyl) (5.72%), heptacosane (5.49%) and phenol,2,4-bis(1-methyl-1-phenylethyl) (5.47%). The composition of the fatty acids in A. dichotoma larvae was also determined by gas chromatography (GC) and fourteen constituents were identified. Oleic acid (19.13%) was the most abundant fatty acid followed by palmitic acid (12.52%), palmitoleic acid (3.71%) and linoleic acid (2.08%) in 100 g of A. dichotoma larvae on a dry weight basis. The quantity of unsaturated fatty acids (64.00%) were higher than that of saturated ones (36.00%). The predominant fatty acids in A. dichotoma consist of monounsaturated fatty acid (MUFA, 57.70%) such as oleic acid, myristoleic acid and palmitoleic acid, followed by saturated fatty acids (36.00%) and polyunsaturated fatty acids (PUFA, 6.50%). In particular, the presence of essential fatty acids, such as linoleic (5.30%) and linolenic acid (0.40%) give A. dichotoma larvae considerable nutritional and functional value and it may be a useful source for food and/or industrial utilization.

• Applied Biological Chemistry
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• v.40 no.2
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• pp.144-147
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• 1997

Different isolation methods for the volatile components of Anise(Pimpinella anisum L.) are compared in terms of the difference of components obtained with each analytical procedure. These methods include headspace(purge & trap) sampling procedure, simultaneous distillation extraction(SDE), steam distillation and solvent extraction. Total 43 components were identified by? comparing gas chromatography retention time and mass spectral data. Different isolation techniques result in compositionally different isolates. The headspace(purge & trap) sampling procedure was found to be the best method of choice for a qualitative analysis of the volatile components.

• 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.

• Journal of the Korean Applied Science and Technology
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• v.18 no.3
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• pp.214-232
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• 2001

CTA ester bonds in TG molecules were not attacked by pancreatic lipase and lipases produced by microbes such as Candida cylindracea, Chromobacterium viscosum, Geotricum candidium, Pseudomonas fluorescens, Rhizophus delemar, R. arrhizus and Mucor miehei. An aliquot of total TG of all the seed oils and each TG fraction of the oils collected from HPLC runs were deuterated prior to partial hydrolysis with Grignard reagent, because CTA molecule was destroyed with treatment of Grignard reagent. Deuterated TG (dTG) was hydrolyzed partially to a mixture of deuterated diacylglycerols (dDG), which were subsequently reacted with (S)-(+)-1-(1-naphthyl)ethyl isocyanate to derivatize into dDG-NEUs. Purified dDG-NEUs were resolved into 1, 3-, 1, 2- and 2, 3-dDG-NEU on silica columns in tandem of HPLC using a solvent of 0.4% propan-1-o1 (containing 2% water)-hexane. An aliquot of each dDG-NEU fraction was hydrolyzed and (fatty acid-PFB ester). These derivatives showed a diagnostic carboxylate ion, $(M-1)^{-}$, as parent peak and a minor peak at m/z 196 $(PFB-CH_{3})^{-}$ on NICI mass spectra. In the mass spectra of the fatty acid-PFB esters of dTGs derived from the seed oils of T. kilirowii and M. charantia, peaks at m/z 285, 287, 289 and 317 were observed, which corresponded to $(M-1)^{-}$ of deuterized oleic acid ($d_{2}-C_{18:0}$), linoleic acid ($d_{4}-C_{18:0}$), punicic acid ($d_{6}-C_{18:0}$) and eicosamonoenoic acid ($d_{2}-C_{20:0}$), respectively. Fatty acid compositions of deuterized total TG of each oil measured by relative intensities of $(M-1)^-$ ion peaks were similar with those of intact TG of the oils by GLC. The composition of fatty acid-PFB esters of total dTG derived from the seed oils of T. kilirowii are as follows; $C_{16:0}$, 4.6 mole % (4.8 mole %, intact TG by GLC), $C_{18:0}$, 3.0 mole % (3.1 mole %), $d_{2}C_{18:0}$, 11.9 mole % (12.5 mole %, sum of $C_{18:1{\omega}9}$ and $C_{18:1{\omega}7}$), $d_{4}-C_{18:0}$, 39.3 mole % (38.9 mole %, sum of $C_{18:2{\omega}6}$ and its isomer), $d_{6}-C_{18:0}$, 41.1 mole % (40.5 mole %, sum of $C_{18:3\;9c,11t,13c}$, $C_{18:3\;9c,11t,13r}$ and $C_{18:3\;9t,11t,13c}$), $d_{2}-C_{20:0}$, 0.1 mole % (0.2 mole % of $C_{20:1{\omega}9}$). In total dTG derived from the seed oils of M. charantia, the fatty acid components are $C_{16:0}$, 1.5 mole % (1.8 mole %, intact TG by GLC), $C_{18:0}$, 12.0 mole % (12.3 mole %), $d_{2}-C_{18:0}$, 16.9 mole % (17.4 mole %, sum of $C_{18:1{\omega}9}$), $d_{4}-C_{18:0}$, 11.0 mole % (10.6 mole %, sum of $C_{18:2{\omega}6}$), $d_{6}-C_{18:0}$, 58.6 mole % (57.5 mole %, sum of $C_{18:3\;9c,11t,13t}$ and $C_{18:3\;9c,11t,13c}$). In the case of Aleurites fordii, $C_{16:0}$; 2.2 mole % (2.4 mole %, intact TG by GLC), $C_{18:0}$; 1.7 mole % (1.7 mole %), $d_{2}-C_{18:0}$; 5.5 mole % (5.4 mole %, sum of $C_{18:1{\omega}9}$), $d_{4}-C_{18:0}$ ; 8.3 mole % (8.5 mole %, sum of $C_{18:2{\omega}6}$), $d_{6}-C_{18:0}$; 82.0 mole % (81.2 mole %, sum of $C_{18:3\;9c,11t,13t}$ and $C_{18:3 9c,11t,13c})$. In the stereospecific analysis of fatty acid distribution in the TG species of the seed oils of T. kilirowii, $C_{18:3\;9c,11t,13r}$ and $C_{18:2{\omega}6}$ were mainly located at sn-2 and sn-3 position, while saturated acids were usually present at sn-1 position. And the major molecular species of $(C_{18:2{\omega}6})(C_{18:3\;9c,11t,13c})_{2}$ and $(C_{18:1{\omega}9})(C_{18:2{\omega}6})(C_{18:3\;9c,11t,13c})$ were predominantly composed of the stereoisomer of $sn-1-C_{18:2{\omega}6}$, $sn-2-C_{18:3\;9c,11t,13c}$, $sn-3-C_{18:3\;9c,11t,13c}$, and $sn-1-C_{18:1{\omega}9}$, $sn-2-C_{18:2{\omega}6}$, $sn-3-C_{18:3\;9c,11t,13c}$, respectively, and the minor TG species of $(C_{18:2{\omega}6})_{2}(C_{18:3\;9c,11t,13c})$ and $ (C_{16:0})(C_{18:3\;9c,11t,13c})_{2}$ mainly comprised the stereoisomer of $sn-1-C_{18:2{\omega}6}$, $sn-2-C_{18:2{\omega}6}$, $sn-3-C_{18:3\;9c,11t,13c}$ and $sn-1-C_{16:0}$, $sn-2-C_{18:3\;9c,11t,13c}$, $sn-3-C_{18:3\;9c,11t,13c}$. The TG of the seed oils of Momordica charantia showed that most of CTA, $C_{18:3\;9c,11t,13r}$, occurred at sn-3 position, and $C_{18:2{\omega}6}$ was concentrated at sn-1 and sn-2 compared to sn-3. Main TG species of $(C_{18:1{\omega}9})(C_{18:3\;9c,11t,13t})_{2}$ and $(C_{18:0})(C_{18:3\;9c,11t,13t})_{2}$ were consisted of the stereoisomer of $sn-1-C_{18:1{\omega}9}$, $sn-2-C_{18:3\;9c,11t,13t}$, $sn-3-C_{18:3\;9c,11t,13t}$ and $sn-1-C_{18:0}$, $sn-2-C_{18:3\;9c,11t,13t}$, $sn-3-C_{18:3\;9c,11t,13t}$, respectively, and minor TG species of $(C_{18:2{\omega}6})(C_{18:3\;9c,11t,13c})_{2}$ and $(C_{18:1{\omega}9})(C_{18:2{\omega}6})(C_{18:3\;9c,11t,13c})$ contained mostly $sn-1-C_{18:2{\omega6}$, $sn-2-C_{18:3\;9c,11t,13t}$, $sn-3-C_{18:3\;9c,11t,13t}$ and $sn-1-C_{18:1{\omega}9}$, $sn-2-C_{18:2{\omega}6}$, $sn-3-C_{18:3\;9c,11t,13t}$. The TG fraction of the seed oils of Aleurites fordii was mostly occupied with simple TG species of $(C_{18:3\;9c,11t,13t})_{3}$, along with minor species of $(C_{18:2{\omega}6})(C_{18:3\;9c,11t,13t})_{2}$, $(C_{18:1{\omega}9})(C_{18:3\;9c,11t,13t})_{2}$ and $(C_{16:0})(C_{18:3\;9c,11t,13t})$. The sterospecific species of $sn-1-C_{18:2{\omega}6}$, $sn-2-C_{18:3\;9c,11t,13t}$, sn-3-C_{18:3\;9c,11t,13t}$, $sn-1-C_{18:1{\omega}9}$, $sn-2-C_{18:3\;9c,11t,13t}$, $sn-3-C_{18:3\;9c,11t,13t}$ and $sn-1-C_{16;0}$, $sn-2-C_{18:3\;9c,11t,13t}$, $sn-3-C_{18:3\;9c,11t,13t}$ are the main stereoisomers for the species of $(C_{18:2{\omega}6})(C_{18:3\;9c,11t,13t})_2$, $(C_{18:1{\omega}9})(C_{18:3\;9c,11t,13t})_{2}$ and $(C_{16:0})(C_{18:3\;9c,11t,13t})$, respectively.