• Journal of the Korean Applied Science and Technology
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• v.18 no.1
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• pp.67-77
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• 2001

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 ${\omega}-5$ double bond system such as $C_{14:1{\omega}5}$, $C_{16:1{\omega}5}$ and $C_{18:1{\omega}5}$, including ${\omega}-7$ fatty acid as $C_{16:1{\omega}7}$ and $C_{18:1{\omega}7}$, 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 $cis-C_{14:1{\omega}5}$, m/z 345, m/z 248 and 288 fragment for $cis-C_{16:1{\omega}5}$ and m/z 373, m/z 276 and 316 fragment for $cis-C_{18:1{\omega}5}$. In this way the occurrence of $cis-C_{16:1{\omega}7}$ and $cis-C_{18:1{\omega}7}$ 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 ${\omega}-5$ fatty acids amounted to about 30% in the fatty acid composition with the predominance of $C_{16:1{\omega}5}$ $ (18.7{\sim}25.0%)$, in the semi-ripened and/or ripened samples collected in September 14 ($C_{16:1{\omega}5}$ ; 18.7%, $C_{14:1{\omega}5}$ ; 3.6% and $C_{18:1{\omega}5}$ ; 3.0%), September 22 ($C_{16:1{\omega}5}$ ; 25.0%, $C_{14:1{\omega}5}$ ; 1.4% and $C_{18:1{\omega}5}$ ; 2.6%), and October $7 (C_{16:1{\omega}5}$ ; 24.7%, $C_{14:1{\omega}5}$ ; 7.7% and $C_{18:1{\omega}5}$ ; 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 ${\omega}-5$ fatty acids in the pulps increased sharply with an elapse of ripening time of jujube fruits. Other monoenoic fatty acids with ${\omega}-7$ series, $C_{16:1{\omega}7}$ (palmitoleic acid) and $C_{18:1{\omega}7}$ (cis-vaccenic acid) could be detected. And in the lipids of the kernel and leaf of jujube, none of ${\omega}-5$ fatty acids could be detected.

• 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.

• Journal of Microbiology and Biotechnology
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• v.10 no.5
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• pp.643-650
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• 2000

A new aniline-utilizing microorganism, strain HY1 obtained from an orchard soil, was characterized by using the BIOLOG system, an analysis of the total cellular fatty acids, and a 16S rDNA sequence. Strain HY1 was identified as a Burkholderia species, and was designated Burkholderia sp. HY1. GC and HPLC analyses revealed that Burkholderia sp. HY1 was able to degrade aniline to produce catechol, which was subsequently converted to cis,cis-muconic acid through an ortho-ring fission pathway under aerobic conditions. Strain HY1 exhibited a drastic reduction in the rate of aniline degradation when glucose was added to the aniline media. However, the addition of peptone or nitrate to the aniline media dramatically accelerated the rate of aniline degradation. A fatty acid analysis showed that strain HY1 was able to produce lipids 16:0 2OH, and 11 methyl 18:1 ${\omega}7c$ approximately 3.7-, 2.2-, and 6-fold more, respectively, when grown on aniline media than when grown on TSA. An analysison the alignment of a 1,435 bp fragment. A phylogenetic analysis of the 16S rDNA sequence based on a 1,420 bp multi-alignment sowed of the 16s rDNA sequence revealed that strain HY1 was very closely related to Burkholderia graminis with 95% similarity based that strain HY1 was placed among three major clonal types of $\beta$-Proteobacteria, including Burkholderia graminis, Burkholderia phenazinium, and Burkholderia glathei. The sequence GAT(C or G)${\b{G}}$, which is highly conserved in several locations in the 16S rDNA gene among the major clonal type strains of $\beta$-Proteobacteria, was frequently replaced with GAT(C or G)${\b{A}}$ in the 16S rDNA sequence from strain HY1.