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중수소화(重水素化), Pentafluorobenzyl화(化)와 GLC-Mass Spectrometry에 의한 Conjugate Trienoic Acid함유(含有) Triacylglycerol 분자종(分子種)의 입체특이적 분석(分析)
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  • 중수소화(重水素化), Pentafluorobenzyl화(化)와 GLC-Mass Spectrometry에 의한 Conjugate Trienoic Acid함유(含有) Triacylglycerol 분자종(分子種)의 입체특이적 분석(分析)
  • Stereospecific Analysis of the Molecular Species of the Triacylglycerols Containing Conjugate Trienoic Acids by GLC-Mass Spectrometry in Combination with Deuteration and Pentafluorobenzyl Derivatization Techniques
저자명
우효경,김성진,조용계,Woo. Hyo-Kyeng,Kim. Seong-Jin,Joh. Yong-Goe
간행물명
한국유화학회지
권/호정보
2001년|18권 3호|pp.214-232 (19 pages)
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한국유화학회
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이 논문은 한국과학기술정보연구원과 논문 연계를 통해 무료로 제공되는 원문입니다.
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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 $sn-1-C_{18:2{omega}6}$, <..