• 한국응용과학기술학회지
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• 제22권4호
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• pp.339-348
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• 2005

On the analysis of triacylglycerol (TG) from the kernels of Acanthopanax sessiliflorus by reversed phase-HPLC, it was separated into three main fractions of PN 44, 46 and 48, according to partition number (PN). On the contrary, it could be clearly classified into seven fractions of SMM, MMM, SMD, MMD, SDD, MDD and MDT by silver ion-HPLC by the number of double bond in the acyl chains of TG species. But resolution of so-called critical pairs of TG molecular species such as molecular pairs of $P_eLL$ $[C_{18:1{\omega}12}/(C_{18:2{\omega}6)2}]$ and OLL $[C_{18:1{\omega}9}/(C_{18:2{\omega}6)2}]$ and OOL $[(C_{18:1{\omega}9)2}/C_{18:2{\omega}6]$, and $P_eP_eL$ $[(C_{18:2{\omega}12)2}/C_{18:1{\omega}6]$ was not achieved $(P_e;$ petroselinic acid, L; linoleic acid, O; oleic acid). On the other hand, TG extracted from Aralia continentalis kernels were also fractionated into seven groups of SSM, SMM, MMM, SMD, MMD, SDD and MDD (S; saturated acid, M; monoenoic acid, D; dienoic acid) by silver ion-HPLC, although it's were classified into three groups of PN 44, 46 and 48 by reversed phase-HPLC. The fractions of SMM, MMM, MMD and MDD were divided into two subfractions, respectively; the fractions of SMM, MMM, MMD and MDD were resolved into the subfraction of $PP_e/P_e$ and POO (critical pairs from each other), that of $P_e/P_e/P_e$ and OOO, that of $P_e/P_e/L$ and OOL, and that of $P_e/L/L$ and OLL.

• 한국응용과학기술학회지
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• 제10권1호
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• pp.1-8
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• 1993

The possibilities for HPLC analysis of lipids have been revolutionised by the availability of evaporative light-scattering detectors, with which the response is independent of the nature of the mobile phase and does not depend On the presence of specific chromophores in the lipids. It was thus possible to develop an HPLC procedure, involving ternary gradient elution, for separating all the lipid classes in animal tissues in a single step. Although reversed-phase HPLC has been widely used for the analysis of molecular species of lipids, sliver ion chromatography can be a valuable alternative. For example, a stable silver ion column for HPLC was developed which permitted resolution of molecular species of triacylglycerols, even from such complex samples as fish oils, again With light-scattering detection and gradient elution. The capacity for HPLC resolution of diastereomeric diacyl-sn-glycerol derivatives, prepared from triacylglycerols. has lead to a new simple method for stereospecific analysis of the latter.

• 한국응용과학기술학회지
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• 제14권1호
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• pp.61-76
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• 1997

Triacylglycerols of the seeds of Ginkgo biloba have been resolved by high-performace liquid chromatography(HPLC} in the silver-ion and reverse-phase modes. The fatty acids were identified by a combination of capillary gas chromatography and gas-chromatography /mass spectrometry as the methyl and /or picolinyl ester. The main components are $C_{18:2{\omega}6}$(39.0mol%), $C_{18:1{\omega}7}$(asclepic acid 21.5mol%), and $C_{18:1{\omega}9}$(oleic acid, 13.8mol%). Considerable amounts of unusual acid such as $C_{20:3{\Delta}^{5,11,14}$ (5.7mol%), $C_{18:2{\Delta}^{5,9}$(2.8mol%), and $C_{18:3}{\Delta}^{5,9,12}$(1.6mol%), were checked. In addition, an anteiso-branched fatty acid, 14-methylhexadecanoic acid, was also present as a minor component(0.9 mol%). The triacylglycerols were separated into 17 fractions by reverse-phase HPLC, and the fractionation was achieved according to the partition numnber(PN) in which a ${\Delta}^5$-non methylene interrupted double bond($^5$-NMDB) showed different behaviour from a methylene interrupted double bond in a molecule with a given cahinlength. Silver-ion HPLC exhibited excellent resolution in which fractions(23 fractions) were resolved on the basis of the number and configuration of double bonds. In this instance, the strength of interaction of a ${\Delta}^5$-NMDB system with silver ions seemed to be weaker than a methylene interrupted double bond system. The principal triacylglycerol species are as follows ; $(C_{18:2{\omega}6)2}/C_{18:1{\omega}7}$, $C_{18:1{\omega}9}/C_{18:1{\omega}7}/C_{18:2{\omega}6}$, $(C_{18:1{\omega}7)2}/C_{18:2{\omega}6}$, $C_{16:1{\omega}7}/C_{18:1{\omega}9}/C_{20:3}{\Delta}^{5,11,14}$, $C_{16:1{\omega}7}/C_{18:1{\omega}7}/C_{20:3}{\Delta}^{5,11,14}$, $C_{18:1{\omega}9}/C_{18:1{\omega}7}/C_{18:2{\omega}6}$, $C_{18:1{\omega}9}/C_{18:2}{\Delta}^{5,5}/C_{20:3}{\Delta}^{5,11,14}$, $(C_{18:1{\omega}7)2}/C_{18:2{\omega}6}$ and $(C_{18:1{\omega}9)2}/C_{18:2{\omega}6}$, while simple triacylglycerols without $C_{18:2{\omega}6})_3$ were not present. Stereospecific analysis showed that fatty acids with ${\Delta}^5$-NMDB system and saturated chains were predominantly located at the site of sn-3 carbon of glycerol backbones. It is evident that there is asymmetry in the distribution of fatty acids in the TG molecules of Ginkgo nut oils.

• 한국응용과학기술학회지
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• 제15권4호
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• pp.1-9
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• 1998

The lipids from the seeds of Pinus koraiensis mostly composed of triacylglycerols (TGs), in which linoleic acid (46.2 mol%) and oleic acid (25.6 mol%) are present as main components in the fatty acid composition. Surprisingly, they also have unusual fatty acids with ${\Delta}^5$-double bond systems such as ${\Delta}^{5.9.12}-C_{18:3}$ (16.0 mol%), ${\Delta}^{5.9}-C_{18:2}$ (2.3 mol%) and ${\Delta}^{5.11.14}-C_{20:3}$ (0.8 mol%). Saturated fatty acids of palmitic, stearic and arachidic acid were present in less than 8.0 mol%. TG was resolved into 17 fractions by reverse-phase HPLC according to so-called partition number (PN) suggested by Plattner, in which TG molecules with ${\Delta}^{5}$-NMDB acyl chains eluted later than did those with ${\Delta}^{9}$-MDB acyl radicals. $Ag^+$-HPLC separated the TG into 14 fractions more clearly than did those with ${\Delta}^{9}$-MDB acyl radicals. $Ag^+$-HPLC separated the TG into 14 fractions more clearly than did reverse-phase HPLC, and the complexity of ${\Delta}^{5.9.12}-C_{18:3}$ moiety with silver ion impregnated in the column bed was in the level between ${\Delta}^{9.12.15}-C_{18:3}$ ($C_{18:3{\omega}3}$) and $C_{18:2{\omega}6}$ (${\Delta}^{9.12}-C_{18:2}$). In the $Ag^+$-HPLC, it was found that the molecular species having a given-numbered double bonds widely spreaded in the acyl chains eluted earlier than those concentrated in one acyl chain. The main molecular species are $(C_{18:2{\omega}6})_2/{\Delta}^{5.9.12}-C_{18:3}$ (14.8 mol%), $C_{18:1{\omega}9}/C_{18:2{\omega}6})_2$ (12.8 mol%) and $C_{18:1{\omega}9}/C_{18:2{\omega}6}/{\Delta}^{5.9.12}-C_{18:3}$ (10.9 mol%).

• 한국응용과학기술학회지
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• 제10권1호
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• pp.57-65
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• 1993

The fatty acid, all $cis-{\Delta}^{5,11,14}-C_{20:3}$, in the Gingko nuts oils, was isolated and, purified by urea-adduct method, silver ion silica gel chromatography and HPLC equipped with reversed phase ${\mu}-Bondapak$ $C_{18}$ column. Its structural elucidation was conducted by IR and $^1H$-, $^{13}C$-NMR technique. The fatty acid composition of seed oils mainly consists of linoleic acid(37.73%), vaccenic acid(18.30%), oleic acid(15.18%), palmitic acid(3.37%), palmitoleic acid(3.37%) and ${\Delta}^5$ NMDB fatty acids(8.50%) in which all $cis-{\Delta}^{5,11,14}-C_{20:2}$ predominates.

• 한국응용과학기술학회지
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• 제18권3호
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• pp.197-213
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• 2001

Conjugate trienoic acids (CTA) occurred in triacylglycerols (TGs) of the seed oils of Trichosanthes kirilowii, Momordica charantia and Aleurites fordii, and they were easily converted to their methyl esters in a mixture of sodium methoxide-methanol without any structural destruction. The main fatty acids in triacylglycerol (TG) fraction of the seed oils of Trichosanthes kirilowii are $C_{18:2{\omega}6}$ (32.2 mol %), $C_{18:3{\;}9c.11t,13c}$ (38.0 mol %) and $C_{18:1{\omega}9}$ (11.8 mol %), followed with $C_{16:0}$ (4.8 mol %) and $C_{18:0}$ (3.1 mol %). The TG fraction was resolved into 20 TG molecular species according to the partition number (PN) by reversed-phase (RP)-HPLC. The main TG species were $DT_{c2}$, $MDT_{c}$ and $D_{2}T_{c}$, of which amounts reached 63 mol % of total TG molecular species. The TG sample was fractionated into 11 fractions according to the number of double bond in the molecule by $Ag^{+}-HPLC$ and the species of $DT_{c2}$, $MDT_{c}$ and $D_{2}T_{c}$ were also eluted as main components. The TG species containing CTA showed unusual behaviours in the order of elution by HPLC ; first, TG moleular species of $DT_{c2}$ (D; dienoic acid, $T_{c}$; punicic acid, $T_{ci}$; ${\alpha}-eleostearic$ acid, M ; monoenoic acid, $S_{t}$; stearic acid) was eluted earlier than $Mt_{c2}$, although they have the same PN number of 40, and, secondly, the species of $DT_{ci2}$ with eight double bonds was eluted earlier than that of $D_2T_{ci}$ with seven double bonds. Intact TG of the seed oils of Momordica charantia contained mainly fatty acids such as $C_{18:3{\omega}9c,11t,13t}$ (57.7 mol %), $C_{18:1{\omega}9}$ (17.4 mol %), $C_{18:0}$ (12.3 mol %) and $C_{18:2{\omega}6}$ (10.6 mol %), and was classified into 13 fractions by RP-HPLC. The main TG species were as follows ; $MT_{ci2}$ [$(C_{18:1{\omega}9})(C_{18:3\;9c,11t,13t})_{2}$, 39.1 mol %] and $S_{t}T_{ci2}$ [$(C_{18:0})(C_{18:3\;9c,11t,13t})_2$, 33.9 mol %] comprising about 73 mol % of total TG species, accompanied by $DT_{ci2}$ [$(C_{18:2{\omega}6})(C_{18:3\;9c,11t,13t})_{2}$, 7.3 mol %], $D_{2}T_{ci}$ [$ (C_{18:2{\omega}6})_{2}(C_{18:3\;9c,11t,13t})$, 3.6 mol %] and $MDT_{ci}$ [$(C_{18:1{\omega}9})(C_{18:2{\omega}6})(C_{18:3\;9c,11t,13t})$, 3.5 mol %]. Simple TG species of $T_{ci3}$ [$(C_{18:3\;9c,11t,13t})_3]$ was present in a small amount of 1.4 mol %, but other simple TG species were not detected. The TG was also resolved into 11 fractions according to the number of double bond by $Ag^{+}-HPLC$, and the species were mainly occupied by $MT_{ci2}$ [$(C_{18:1{\omega}9})(C_{18:3\;9c,11t,13t})_{2}$, 39.4 mol %] and $S_tT-{ci2}$ [$(C_{18:0})(C_{18:3\;9c,11t,13t})_{2}$, 35.4 mol %] $DT_{ci2}$ species with eight double bonds was also developed faster than $D_2T_{ci}$ one with seven double bonds as indicated in the analysis of TG of the seed oils of T. kirilowii, and $MT_{ci2}$ species with cis, trans, trans-configurated double bond was eluted earlier than $MT_{c2}$ species with cis, trans, cis-configurated double bond. The main components of fatty acid in total TG fraction isolated from the seed oils of of Aleurites fordii were in the following order ; $C_{18:3\;9c,11t,13t}$ (81.2 mol %)> $C_{18:2{\omega}6}$ (8.5 mol %)> $C_{18:1{\omega}9}$ (5.4 mol %)$. With resolution of the TG by RP-HPLC, eight fractions such as $T_{ci3}$, $Dt_{ci2}$, $D_{2}T_{ci}$, $MT_{ci2}$, $PT_{ci2}$ (P; palmitic acid), $PMT_{ci}$, $PDT_{ci}$ and $S_{t}T_{ci2}$ ($S_{t}$; stearic acid) were isolated, respectively. TG species of $T_{ci3}$ [$(C_{18:3\;9c,11t,13t})_{3}$, 54.2 mol %], $DT_{ci2}$ [$(C_{18:2{\omega}6})(C_{18:3\;9c,11t,13t})_{2}$, 15.0 mol %] and $MT_{ci2}$ [$(C_{18:1{\omega}9})(C_{18:3 9c,11t,13t})_{2}$, 14.8 mol %] were present as main species.

• 한국응용과학기술학회지
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• 제12권2호
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• pp.121-130
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• 1995

This project has been worked out for isolation of EPA-producing bacteria from marine source of sea water, sea sediment and intestinal contents eviscerated from some red-muscle fish such as mackerel, horse-mackerel and spike fish. The samples were precultured on the media of PPES-II glucose broth and then pure-cultured on Nutrient agar and P-Y-M glucose. Lipids extracted from those bacterial mass collected by centrifugation were analysed in terms of lipid class and fatty acid composition. The results are resumed as follows : 1. 112 strains from sea water and 76 strains from sea sediment were tested for their EPA producing capability, but both strains of (SA-67 and SA-91) from the former and four strains(SS-35, 37, 51 and 71) from the latter have been proved to produce EPA above the level of 2% of total fatty acids. The strains such as GS-11, 29, 31, HM-9, 29, B-18, 33, 107, YL-129, 156, 203, 77, 104 and 256 which were isolated from fish intestinal contents, have also produced EPA at higher level than 2% of total fatty acids. 2. Contents of total lipids extracted from the cultures of these strains grown at $25^{\circ}C$, range from 2.8% to 6.9% (on dry weight %), and they are mainly composed of polar lipids($40.9{\sim}52.9%$) such as phosphatidyl glycerol($^{+}cardiolipin$)(?) and phosphatidyl ethanolamine ($33.8{\sim}40.0%$), with smaller amount of free fatty acid ($11.2{\sim}20.2%$). 3. EPA was isolated from a mixture of fatty acid methyl esters obtained from the lipid of each strain by HPLC in silver-ion mode and was identified by GC-Mass spectrometry. 4. The strains of SW-91, GS-11, GS-29, HM-9, B-18 and YL-203 grown at $25^{\circ}C$ have a level of 5% EPA in their total fatty acids, and the GS-11 and HM-9 strains show a tendency of increase in the EPA level with an increase of growth temperature.

• 한국식품과학회지
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• 제43권6호
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• pp.689-695
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• 2011

모유대체지를 합성하기 위하여 palm stearin을 acetone fractionation으로 획득한 PPP rich fraction과 oleic ethyl ester를 기질로 사용하고, sn-1,3 위치 선택성을 가진 Lipozyme TLIM을 이용하여 에스테르 교환반응을 수행하였다. 반응 조건(반응 온도, 반응 시간, 기질의 비율)을 요인 변수로 하여 중심 합성 계획에 의한 반응표면분석을 이용하였고, 비 용매 계에서의 반응을 통해 sn-2 위치에 팔미트산의 함량이 높고, sn-1,3에 올레산의 함량이 높은 1,3-dioleoyl-2-palmitoyl glycerol(OPO) 합성 조건을 최적화 하였다. 모델에 의하여 구해진 최적화 조건은 반응온도=$55^{\circ}C$, 반응시간 =3시간, 기질비율=1:6이었고 이때 sn-2 위치의 팔미트산($Y_1$, %)의 함량은 70.70%이었고 sn-1,3 위치의 올레산($Y_2$, %) 함량은 69.58% 이었다. 최적조건에서 합성된 모유대체지를 silver ion HPLC분석 결과 SSS(5.22%), SSU(36.28%), SUU(12.94%), USU(31.24%), UUU(11.04%)로 나타났다. 한편, TAG(90.35 g/100 g), 1,3-DAG (5.66 g/100 g)와 1,2-DAG(4.00 g/100 g)로 구성되어 있었고, 1,3-DAG 가 1,2-DAG 보다 많이 생성되는 것으로 나타났다.

• 한국식품영양과학회지
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• 제40권9호
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• pp.1256-1264
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• 2011

시중에 유통되고 있는 조제분유의 지방산 및 TAG 조성을 알아보기 위하여 국내외 조제분유 총 11 품목을 선정하였고, Folch법을 이용하여 지방을 추출한 다음 총 지방산과 sn-2 위치의 지방산 및 silver ion HPLC를 이용한 단일불포화-포화-단일불포화 glycerol(MSM)의 조성을 분석하였다. 조제분유의 조지방의 함량은 17.21~23.51%이었고, 특히 K5의 조지방 함량이 23.51%로써 분석된 조제분유들 중에서 가장 높게 나왔으나, K1은 17.21%의 함량을 보이면서 가장 낮게 나타났다. 분석된 조제분유들의 주요 포화지방산은 lauric acid(C12:0), myristic acid(C14:0), palmitic acid(C16:0), stearic acid(C18:0)이었다. Lauric acid의 함량은 K5와 K6에서 19.49%와 23.34%로 분석되어 15%보다 높은 함량을 나타냈다. 한편, 분석된 조제분유의 palmitic acid의 함량은 7.59~21.65%의 범위로써 K2, K3, K6, F1에서 각각 14.64%, 8.29%, 13.47% 및 7.59%로써 낮은 함량을 나타냈다. 불포화 지방산들 중에서 단일불포화지방산(C14:1, myristoleic acid; C16:1, palmitoleic acid; C17:1, heptadecenoic acid; C18:1, oleic acid; C18:1t, elaidic acid)의 함량은 20.23~45.07%로 나타났고, 단일불포화지방산들 중에서 대부분을 구성하고 있는 지방산은 oleic acid(C18:1)이었다. 분석된 조제분유에서 oleic acid의 함량은 19.64~44.64%의 범위였고 총 다가불포화지방산은 19.08~29.67%의 범위였다. Omega-6 다가불포화지방산과 omega-3 다가불포화지방산의 주요한 지방산은 필수지방산인 linoleic acid(C18:2)와 linolenic acid(C18:3, n-3)로 분석된 조제분유의 비율은 10:1~13:1로, 조제분유의 지방산 조성에 대한 지표인 linoleic acid/linolenic acid의 비율인 5:1~15:1 범위 내였다. 분석한 조제분유들 중에서 sn-2 위치에서의 lauric acid 함량은 7.70~52.09%로 나타났고, myristic acid의 함량은 3.15~20.89%로써 분석된 조제분유들은 전반적으로 sn-2 위치에서의 lauric acid 함량이 20% 이상으로 높게 나타났다. 특히, 분석된 조제분유들의 sn-2 위치에 존재하는 palmitic acid의 함량은 1.84~38.74%의 범위로써 K8과 F3이 각각 38.55%와 38.90%의 높은 함량을 나타냈다. 따라서 대부분의 국내외 조제분유들을 구성하는 triacylglycerol(TAG)의 sn-2 위치에서의 palmitic acid 함량이 모유와 비교하였을 때 낮은 경향을 보임을 알 수 있었다. 이러한 조제분유보다 더 나아가 HPLC 분석을 통해서 모유의 주요 TAG 형태라고 할 수 있는 단일불포화-포화-단일불포화 glycerol(MSM)의 함량이 외국의 조제분유인 F3이 가장 높게 나타났다. 따라서 조제분유에 이러한 MSM 형태의 지방 함량을 높여야하며, MSM 형태의 모유대체지 연구를 산업화하려는 노력이 필요하다.