立本特異的 方法과 ₁₃C-NMR 技法에 의한 잣기름의 트리아실 글리세롤의 構成脂肪酸의 分布에 관한 硏究

우효경(Woo Hyo Kyeng)(禹孝京),김성진(Kim Seung Jin)(金成眞),조용계(Joh Yong Goe)(趙鏞桂) 한국유화학회 1998 한국응용과학기술학회지 Vol.15 No.4

All the triacylglycerols including the molecular species having △^5-unsaturated fatty acids from the seeds of Pinus Koraiensis, were split into a mixture of diacylglycerols by a Grignard reagent prepared with allyl bromide without arousing acyl chains of a glycerol moiety to migration, and were also easily partially hydrolyzed to diacylglycerols by pancreatic lipase. (S)-(+)-(1-naphthyl)ethyl urethane(NEU) derivatives of the diacylglycerol mixture derived from the triacylglycerols were fractionated into sn-1, 3-, sn-1, 2- and sn-2, 3-DG-NEU by silica-HPLC and the fatty acid composition of these fractions was analysed. C_18:1ω9 is distributed evenly in the three positions of TG with C_18:2ω6 mainly located in sn-2 position, while △^5-unsaturated fatty acids such as △^5.9-C_18:2, △^5.9.12-C^18:3 and △^5.11.14-C_20:3 are exclusively present in the sn-3 position. These results could be confirmed by ^13C-NMR sepctroscopy : the signals at δ173.231 ppm and δ172.811 ppm of the carbonyl carbon of acyl moieties indicate the presence of saturated acids and/or C_18:1ω9 (oleic acid) in the α(α`)-or β- positions, and C_18:2ω6 including C_18:1:ω9 in the β-position, respectively. In addition, the resonance at δ173.044 ppm suggested a location of △^5-unsaturated fatty acid moiety in the α(α )-position.

중수소화 , Pentafluorobenzyl 화와 GLC - Mass Spectrometry 에 의한 Conjugate Trienoic Acid 함유 Triacylglycerol 분자종의 입체특이적 분석

우효경(Hyo Kyeng Woo),김성진(Seong Jin Kim),조용계(Yong Goe Joh) 한국유화학회 2001 한국응용과학기술학회지 Vol.18 No.3

N/A 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_2C_18:0, 11.9 mole % (12.5 mole %, sum of C_18:1ω9 and C_18:1ω7), d_4-C_18:0, 39.3 mole % (38.9 mole %, sum of C_18:2ω6 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_20:1ω9). 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_18:1ω9), d_4-C_18:0, 11.0 mole % (10.6 mole %, sum of C_18:2ω6), 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:o ; 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_18:1ω9), d_4-C_18:0 ; 8.3 mole % (8.5 mole %, sum of C_18:2ω6), 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_18:2ω6 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_18:2ω6)(C_18:3 9c,11t,13c)_2 and (C_18:1ω9)(C_18:2ω6)(C_18:3 9c,11t,13c) were predominantly composed of the stereoisomer of sn-1-C_18:2ω6, sn-2-C_18:3 9c,11t,13c, sn-3-C_18:3 9c,11t,13c, and sn-1-C_18:1ω9, sn-2-C_18:2ω6, sn-3-C_18:3 9c,11t,13c, respectively, and the minor TG species of (C_18:2ω6)_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_18:2ω6, sn-2-C18:2ω6, sn-3-C18:3 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_18:2ω6 was concentrated at sn-1 and sn-2 compared to sn-3. Main TG species of (C_18:1ω9)(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-C18:1ω9, sn-2-C_18:3 9c,11t,13t, sn-3-C18:3 9c,11t,13t and sn-1-C_18:0, sn-2-C_18:3 9c,11t,13t,

입본특이적(立本特異的) 방법(方法)과 $^{13}C-NMR$ 수식 이미지 기법(技法)에 의한 잣기름의 트리아실 글리세롤의 구성지방산(構成脂肪酸)의 분포(分布)에 관한 연구(硏究)

우효경(Woo, Hyo-Kyeng),김성진(Kim, Seung-Jin),조용계(Joh, Yong-Goe) 한국유화학회 1998 한국응용과학기술학회지 Vol.15 No.4

All the triacylglycerols including the molecular species having ${\Delta}^5$ 수식 이미지-unsaturated fatty acids from the seeds of Pinus Koraiensis, were split into a mixture of diacylglycerols by a Grignard reagent prepared with allyl bromide without arousing acyl chains of a glycerol moiety to migration, and were also easily partially hydrolyzed to diacylglycerols by pancreatic lipase. (S)-(+)-(1-naphthyl)ethyl urethane(NEU) derivatives of the diacylglycerol mixture derived from the triacylglycerols were fractionated into sn-1, 3-, sn-1, 2- and sn-2, 3-DG-NEU by silica-HPLC and the fatty acid composition of these fractions was analysed. $C_{18:1{\omega}9}$ 수식 이미지 is distributed evenly in the three positions of TG with $C_{18:2{\omega}6}$ 수식 이미지 mainly located in sn-2 position, while ${\Delta}^5$ 수식 이미지-unsaturated fatty acids such as ${\Delta}^{5.9}-C_{18:2}$ 수식 이미지, ${\Delta}^{5.9.12}-C_{18:3}$ 수식 이미지 and ${\Delta}^{5.11.14}-C_{20:3}$ 수식 이미지 are exclusively present in the sn-3 position. These results could be confirmed by $^{13}C$ 수식 이미지-NMR spectroscopy : the signals at $^{\delta}$ 수식 이미지173.231 ppm and $^{\delta}$ 수식 이미지172.811 ppm of the carbonyl carbon of acyl moieties indicate the presence of saturated acids and/or $C_{18:1{\omega}9}$ 수식 이미지 (oleic acid) in the ${\alpha}({\alpha}- or ${\beta}$ 수식 이미지- positions, and $C_{18:2{\omega}6}$ 수식 이미지 including $C_{18:1{\omega}9}$ 수식 이미지 in the ${\beta}$ 수식 이미지-position, respectively. In addition, the resonance at $^{\delta}$ 수식 이미지173.044 ppm suggested a location of ${\Delta}^5$ 수식 이미지-unsaturated fatty acid moiety in the ${\alpha}({\alpha}-position.

대추의 과육지질에 존재하는 지방산의 동정과 숙성에 따른 그 조성의 변화

우효경(Hyo Kyeng Woo),김성진(Seong Jin Kim),박성혜(Sung Hea Park),조용계(Yong Goe Joh) 한국유화학회 2001 한국응용과학기술학회지 Vol.18 No.1

N/A In search for several fatty acid with unusual structure in vegetable oils, we have found that unknown peaks were shown on GLC in the analysis of fatty acids of the lipids from the pulp of ripened jujube (Zizypus jujuba var. inermis) fruits. These fatty acids were identified as a series of cis-monoenoic acids with ω-5 double bond system such as C_14:1ω5, C_16:1ω5 and C_18:1ω5, including ω-7 fatty acid as C_16:1ω7 and C_18:1ω7, by GLC, solid-phase extraction silver ion-column chromatographic, GLC-mass spectrometric and IR techniques. First of all, total fatty acid methyl esters were resolved into saturated and branched fatty acid, monoenoic acid, dienoic acid, and trienoic acid fraction, respectively, with 100% dichloromethane (DCM), DCM/acetone (9:1, v/v) 100% acetone, and acetone/ acetonitrile (97:3, v/v) solvent system. Unknown fatty acids were included in the monoenoic fraction and were confirmed to have cis-configuration by IR. Picolinyl esters of monoenoic fatty acids gave distinct molecular ion peak and dominant diagnostic peaks, for example, m/z 317, 220 and 260 fragment for cis-C_14:1ω5, m/z 345, m/z 248 and 288 fragment for cis-C_16:1ω5 and m/z 373, m/z 276 and 316 fragment for cis-C_18:1ω5. In this way the occurrence of cis-C_16:1ω7 and cis-C_18:1ω7 could be deduced from the appearance of prominent fragments as m/z 345, 220 and 260, and m/z 373, 248 and 280. Level of total ω-5 fatty acids amounted to about 30% in the fatty acid composition with the predominance of C_16:1ω5 (18.7~25.0%), in the semi-ripened and/or ripened samples collected in September 14 (C_16:1ω5 ; 18.7%, C_14:1ω5 ; 3.6% and C_18:1ω5 ; 3.0%), September 22 (C_16:1ω5 ; 25.0%, C_14:1ω5 ; 1.4% and C_18:1ω5 ; 2.6%), and October 7 (C_16:1ω5 ; 24.7%, C_14:1ω5 ; 7.7% and C_18:1ω5 ; 2.5%). However, the lipids extracted from unripened jujube in July and August contain these unusual fatty acids as low as negligible. It could be observed that the level of ω-5 fatty acids in the pulps increased sharply with an elapse of ripening time of jujube fruits. Other monoenoic fatty acids with ω-7 series, C_16:1ω7 (palmitoleic acid) and C_18:1ω7 (cis-vaccenic acid) could be detected. And in the lipids of the kernel and leaf of jujube, none of ω-5 fatty acids could be detected.

Near Infrared Treatment Effect on Young Barley Leaf Growth

Sang-Woo Kang,Jin-Seong Kim,Kyeng-Yeol Oh,Jin-Hyo Kim 한국농약과학회 2023 한국농약과학회 학술발표대회 논문집 Vol.2023 No.11

Quantitative Analysis of Trihalomethane as a Potential Methanogenesis Inhibitor in Green Algaes

Sang-Woo Kang,Jin-Seong Kim,Kyeng-Yeol Oh,Jin-Hyo Kim 한국농약과학회 2023 한국농약과학회 학술발표대회 논문집 Vol.2023 No.11

Analysis of Fatty Acids in Puffer Fish Liver Oils by Combined Chromatographic Procedures

Seong-Jin Kim,Hyo-Kyeng Woo,Min-Young Seo,Yong-Goe Joh 한국식품과학회 2003 Food Science and Biotechnology Vol.12 No.4

The Molecular Species of Triacylglycerols in the Seed Oils of Momordica charantia L.

Yong Goe Joh,Hyo Kyeng Woo,Sung Jin Kim 한국유화학회 1998 KOREAN JOURNAL OF OIL AND FAT CHEMISTRY Vol.1 No.1

Identification of Fatty Acids in the Oils of Pine Nuts by GC-MS of Their Picolinyl Esters and 4,4-dimethyloxazoline Derivatives in Combination with Silver-Ion Chromatography

Seong-Jin Kim,Hyo-Kyeng Woo,Min-Young Seo,Yong-Goe Joh 한국유화학회 2002 한국응용과학기술학회지 Vol.19 No.3

A mixture of methyl ester derivatives of fatty acids from the oils of pine nuts was well resolved to five fractions differing by degree of unsaturation by silver ion solid-phase extraction column chromatography (Ag+-SEC). Polyunsaturated fatty acid with non-methylene interrupted conjugated double bond (NMiDB) radical held more strongly to silver ions in the column than methylene interrupted conjugated double bond (MiDB) one when they had the same number of double bonds. Although both the picolinyl ester and DMOX derivative provided clear mass ion species powerful enough to elucidate the structure of the polyunsaturated fatty acid (PUFA) with NMiDB and/or methylene interrupted conjugated double bond (MiDB) radical in the oils, the picolinyl ester of PUFA with NMiDB radical did not provide a cluster of mass ions neighboring diagnostic mass ions induced by the double bond in the proximal to the carboxyl group. However, the DMOX derivative of PUFA with NMiDB group as well as MiDB showed abundant mass ion species differing by gaps of 12 amu, which made it possible with greater ease to locate the double bonds in the molecule. The oil contained C18:2Ω6 (46.2 %) and C18:1Ω9 (25.4 %) as main components, and considerable amounts of PUFAs with NMiDB radical such as δ5. 9. 12-C18:3 (16.0 %), δ5. 9-C18:2 (2.3 %) and δ5. 11. 14-C20:3 (0.8 %).

역상 (逆相) - HPLC 와 Ag+ - HPLC 에 의한 잣기름의 트리아실글리세롤 분자종의 상호분리

조용계,우효경,김성진 한국유화학회 1998 한국응용과학기술학회지 Vol.15 No.4

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 △^5-double bond systems such as △^5.9.12-C_18:3 (16.0 mol%), △^5.9-C_18:2 (2.3 mol%) and △^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 △^5-NMDB acyl chains eluted later than did those with △^9-MDB acyl radicals. Ag^+-HPLC separated the TG into 14 fractions more clearly than did those with △^9-MDB acyl radicals. Ag^+-HPLC separated the TG into 14 fractions more clearly than did reverse-phase HPLC, and the complexity of △^5.9.12-C_18:3 moiety with silver ion impregnated in the colum bed was in the level between △^9.12.15-C_18:3 moiety with silver ion impregnated in the column bed was in the level between △^9.12.15-C_18:3 (C_18:3ω3) and C_18:2ω6 (△^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_18:2ω6)_2/△^5.9.12-C_18:3 (14.8 mol%), C_18ω9/(C_18:2ω6)_2 (12.8 mol%) and C_18:1ω9/C_18:2ω6/△^5.9.12-C_18:3 (10.9 mol%).