• 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.

• Journal of the Korean Chemical Society
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• v.40 no.4
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• pp.219-228
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• 1996

An ab initio molecular orbital method has been applied to investigation of molecular properties and equilibrium geometries for hexahydroxybenzene triscarbonate (C9O9) and its analogous cyclic compounds (C9S9, C9O6S3, C9O3S6). In these works, the optimized geometry of each compound has been obtained at HF and MP2 levels. These results have shown that the optimized geometries of these compounds prefer D3h planar structure to C3v bowl structure. Calculations of harmonic vibrational frequencies have been also carried out at HF/3-21G* level to analyze normal modes of these compounds. Bonding characters of these compounds are studied by Mulliken and natural populations obtained at HF/6-31G* level. We have also studied the structures and the populations of C6O6 and C6S6 at HF and MP2 levels which are obtained by pyrolyses of C9O9 and analogous compounds. In addition, the single point calculations have been performed to predict the approximate energy barrier for pyrolysis of each compound.

• Bulletin of the Korean Chemical Society
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• v.34 no.5
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• pp.1414-1420
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• 2013

Five novel spiro[benzo[c]fluorene-7,9'-fluorene] based dyes, including 5-[spiro[benzo[c]fluorene-7,9'-fluoren]-5-yl] spiro[benzo[c]fluorene-7,9'-fluorene] (7), 5-[spiro[benzo[c]fluorene-7,9'-fluoren]-9-yl] spiro[benzo[c]fluorene-7,9'-fluorene] (8), 5-[spiro[benzo[c]fluorene-7,9'-fluoren]-2'-yl] spiro[benzo[c]fluorene-7,9'-fluorene] (9), 9-[spiro[benzo[c]fluorene-7,9'-fluoren]-9-yl] spiro[benzo[c]fluorene-7,9'-fluorene] (10), and 2'-[spiro[benzo[c]-fluorene-7,9'-fluoren]-2'-yl] spiro[benzo[c]fluorene-7,9'-fluorene] (11) were successfully prepared from the corresponding halogen and boronic acid derivatives through the Suzuki coupling reaction, respectively. Chemical structures were confirmed by $^1H$ nuclear magnetic resonance (NMR), $^{13}C$ NMR, Fourier transforminfrared spectrscopy, mass spectroscopy, and elemental analysis. The thermal properties were determined by differential scanning calorimetry and thermal gravimetric analysis. The relationships between the optical and electrochemical properties and the combined positions between these dimers were systematically investigated using UV-vis, photoluminescence (PL), and photoelectron spectroscopy. These five dimers exhibited high fluorescent quantum yields and good morphological stability with high glass transition states > $174^{\circ}C$. Dimer 7 showed a UV absorbance peak at 353 nm, emission PL peak at 424 nm, and quantum efficiency of 0.62 in a cyclohexane solution.

• Analytical Science and Technology
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• v.21 no.3
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• pp.212-221
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• 2008

In order to investigate the information for effective detection and developing of latent fingerprints, we identified fatty acids composition of latent fingerprints on non-porous evidence surface and the chemical changes of latent fingerprint residue after print deposition during 7 months. Fingerprints from eight Korean male donors (aged 29-50 years) and one female donor (aged 36 years) were collected. All fingerprints were found to contain lauric acid (C12:0), myristic acid (C14:0), palmitic acid (C16:0), stearic acid (C18:0), elaidic acid (C18:1n9t), oleic acid (C18:1n9c), linoleic acid (C18:2n6c), arachidic acid (C20:0), linolenic acid (C18:3n3), erucic acid (C22:1n9) and docosadienoic acid (C22:2) and primarily palmitic acid (35.45-48.37%), oleic acid (14.84-28.49%), stearic acid (9.71-24.96%) and linoleic acid (7.68-18.8%) occupied 75% of total fatty acids. When the fingerprints were deposited at dark room for 7 months, total fatty acids components decreased about 12-25%. It can be explained that significant degradation of long-chain fatty acids such as elaidic acid (C18:1n9t), arachidic acid (C20:0), linolenic acid (C18:3n3), erucic acid (C22:1n9), and docosadienoic acid (C22:2) resulted in the generation of myristic acid (C14:0), myristoleic acid (C14:1) and pentadecanoic acid (C15:0).

• Korean Chemical Engineering Research
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• v.44 no.4
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• pp.363-368
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• 2006

This study selected the optimal catalyst for the process of producing $C_9$-alcohol by hydrogenating $C_9$-aldehyde, and carried out an experiment in order to establish the operating condition for maximizing the yield of $C_9$-alcohol. The BET surface area and the specific area of copper were most excellent in $CuO/ZnO/Al_2O_3$ (60:30:10 wt％) catalyst produced using acetate as a precursor of copper and $Na_2CO_3$ as a precipitant, and the catalyst also showed the highest performance in $C_9$-aldehyde hydrogenation. Using a trickle bed reactor loaded with optimized catalyst, we attained 94.1 wt％ yield of $C_9$-alcohol under the condition of $175^{\circ}C$, 800 psi and $WHSV=3hr^{-1}$. According to the result of comparing with other catalysts used in the hydrogenation of aldehyde, the catalyst showed similar performance to that of Ni/kieselghur and higher than that of $Cu-Ni-Cr-Na/Al_2O_3$ and $Ni-Mo/Al_2O_3$. According to the result of examining the stability of the catalyst through a long-term catalysis test, the yield of $C_9$-alcohol decreased slowly after around 72 hours due to the increasing production of high boiling-point byproducts.

• Biomedical Science Letters
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• v.2 no.2
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• pp.231-240
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• 1996

Human blood clotting (coagulation) factor 9 cDNA which codes for 461 amino acid has been cloned by screening human fetal liver cDNA library using PCR. This 1.4 kb cDNA spanning from the ATG initiation codon to the TAA termination codon was cloned into bacterial .expression vector pGEX-2T, generating pGEX-F9 plasmid. The plasmid pGEX-F9 expresses about 73 kDa GST (Glutathione S-transferase)-Factor 9 fusion protein when introduced into E. coli. Western blot analysis using polyclonal antibody raised against human factor 9 confirmed this fusion protein contains factor 9 protein. The level of GST-factor 9 expression was about 20% of total protein and the purification of fusion protein was efficiently achieved by using GST agarose bead based on one step purification protocol.

• Journal of the Korean Applied Science and Technology
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• v.9 no.2
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• pp.149-156
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• 1992

Levels of total lipids in the seeds of three species of the Pinaceae family were determined and their fatty acid compositions were also analyzed by a gas-chromatograph equipped with a capillary column coated with Carbowax 20M. The results are summarized as follows: Lipid contents of the seeds amounted to 56.9% in P. koraiensis, 29.9% in P. thunbergii, and 21.2% in P. rigida. In all lipids 19${\sim}$20 fatty acid were detected and, surprisingly, fatty acids having ${\Delta}^5$-non-methylene interrupted conjugate double bond such as ${\Delta}^{5, 9}-C_{18:2},{\Delta}^{5, 9, 12}-C_{18:3}\;and\;{\Delta}^{5, 11, 14}-C_{20:3}$ occurred in appreciable amounts. In the lipids of P. koraiensis, the main component was $C_{18:2}{\omega}_6(45.0%)$, followed by $C_18:1{\omega} _9(26.9%)$ and ${\Delta}^{5, 9, 12}-C_{18:3}(14.6%)$, and then ${\Delta}^{5, 9}-C_{18:2}(2.2%)$ and ${\Delta}^{5, 11, 14}-C_{20:3}$ were also present. Levels of saturated fatty acid such as $C_{16:0}\;and\;C_{18:0}$ were as low as 7.5%. The seed oil of P. thunbergii predominantly comprised $C_{18:2}{\omega}_6(45.2%)$, and was then occupied by equal amounts ${\Delta}^{5, 9, 12}-C_{18:3}(18.1%)$ and $C_{18:1}{\omega}_9(18.1%)$. Its ${\Delta}^5, 11, 14}-C_{20:3}(5.8%)$ level was the highest in the samples tested. ${\Delta}^{5, 9}-C_{18:2}(2.8%)$ was also detected with other minor components. In the oils from the seeds of P. rigida, $C_{18:2}{\omega}_6$ was present as a main component, accompanied by $C_{18:1}{\omega}_9(21.6%)$ and ${\Delta}^{5, 9, 12}-C_{18:3}(20.3%)$. The latter showed higher level than in any other samples. A minor component corresponding to ${\Delta}^{5, 9, 12, 15}-C_{18:4}$(not confirmed by GC-Mass) occurred in P. thunbergii and P. rigida.

• Journal of Veterinary Clinics
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• v.21 no.4
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• pp.336-342
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• 2004

The immunoenhancing effect of CLA isomers (CLA mixture, 10t-12c CLA, 9c-11c CLA, 9c-11c CLA, and 9t-11t CLA) on phagocytic activity of porcine peripheral blood leukocytes was examined. The phagocytic activities of peripheral blood mononuclear cells (PBMC) and polymorphonuclear cells (PMN) were analyzed by a flow cytometry system. The direct treatments of CLA isomers have no effect on phagocytosis of PMN as well as PBMC composed of approximately 10% monocytes and 90% lymphocytes. However, the phagocytic activities of PMN and monocyterich fraction from PBMC were remarkably enhanced by culture supernatant from PBMC treated with CLA mixture, 10t-12c CLA and 9c-11t CLA but not 9c-11c CLA and 9t-11t CLA. The phagocytic activity of PBMC was not enhanced by culture supernatant from PBMC treated with all CLA isomers. These results indicated that CLA isomers such as CLA mixture, l0t -12c CLA and 9c-11t CLA have an enhancing effect on phagocytosis of PMN and monocytes, which may be mediated through active humoral substances produced by CLA-stimulated PBMC. This study suggested that CLA stimulates PBMC to elaborate soluble factor(s), which may be an important mechanism for the enhancement of phagocytosis in non-specific immunity.

• Journal of the Korean Applied Science and Technology
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• v.18 no.3
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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.

• Archives of Pharmacal Research
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• v.26 no.11
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• pp.967-973
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• 2003

Cytochrome P4502C9(CYP2C9) is largely responsible for terminating anticoagulant effect by hydroxylation of S-warfarin to inactive metabolites. Mutations in the CYP2C9 gene result in the expression of allelic variants, CYP2C9*2 and CYP2C9*3 with reduced enzyme activity compared to wild type CYP2C9 *1. The aim of this study was to assess relationship between requirement of warfarin dose and polymorphism in CYP2C9 in Korean population. Patients on warfarin therapy for longer than 1 year were included from July 1999 to December 2000 and categorized as one of four groups; regular dose non-bleeding, regular dose bleeding, low dose non-bleeding and low dose bleeding. Low dose was defined as less than 10 mg/week for 3 consecutive monthly follow-ups. Bleeding complications included minor and major bleedings. Blood samples were processed for DNA extraction, genotyping and sequencing to detect polymorphism in CYP2C9. Demographic data, warfarin dose per week, prothrombin time (INR), indications and co-morbid diseases were assessed for each group. Total 90 patients on warfarin were evaluated; The low dose group has taken warfarin 7.6$\pm$1.7 mg/week, which was significantly lower than 31.4$\pm$0.9 mg/week in the regular dose group (p<0.0001). The measured INR in the low dose group was similar to that of the regular dose group (2.3$\pm$0.7 vs. 2.3$\pm$0.6, p=0.9). Even though there was a higher possibility of CYP2C9 variation in the low dose group, no polymorphism in CYP2C9 was detected. All patients were homozygous C416 in exon 3 for CYP2C9*2 and A1061 in exon 7 for CYP2C9*3. The DNA sequencing data confirmed the homozygous C416 and A 1061 alleles. In conclusion, polymorphism in CYP2C9 is not a critical factor for assessing warfarin dose requirement and risk of bleeding complications in a Korean population.