• Journal of Microbiology and Biotechnology
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• 제20권5호
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• pp.875-880
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• 2010

Bacterial enoyl-ACP reductase (FabI) has been demonstrated to be a novel antibacterial target. In the course of our screening for FabI inhibitors, we isolated two methyl-branched fatty acids from Streptomyces sp. A251. They were identified as 14-methyl-9(Z)-pentadecenoic acid and 15-methyl-9(Z)-hexadecenoic acid by MS and NMR spectral data. These compounds inhibited Staphylococcus aureus FabI with $IC_{50}$ values of 16.0 and $16.3\;{\mu}M$, respectively, but did not affect FabK, an enoyl-ACP reductase of Streptococcus pneumonia, at $100\;{\mu}M$. Consistent with their selective inhibition for FabI, they blocked intracellular fatty acid synthesis as well as the growth of S. aureus, but did not inhibit the growth of S. pneumonia. Additionally, these compounds showed reduced antibacterial activity against fabI-overexpressing S. aureus, compared with the wild-type strain. These results demonstrate that the methylbranched fatty acids show antibacterial activity by inhibiting FabI in vivo.

• 한국식품영양과학회지
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• 제22권3호
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• pp.300-306
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• 1993

2-Methylbutanoic, 3-methylbutanoic, 4-methylpentanoic, 2-ethylhexanoic, 4-methylhexanoic, 4-methyloctanoic, 6-methyloctanoic, 4-ethylhexanoic. 4-methylhexanoic 및 2-ethylhexanoic acids를 포함하는 다수의 volatile branched-chain fatty acids(VBCFAs)가 쇠고기, 돼지고기, 염소고기(미국산 흰염소고기, 한국산 흑염소고기), 양고기로부터 분리, 동정되었다. 쇠고기 향은 amino acid, carbohydrate, 그리고 lipid의 반응에 의해 생성된 향기성분에 의해 이루어지는 기본 meaty flavor로 결정되어 지는 반면, 염소고기가 양고기의 경우는 쇠고기의 기본향에 4-ethyloctanoic acid와 4-methyloctanoic acid의 독특한 노린내가 더해지므로 염소고기나 양고기 특유의 향을 내었다. 돼지고기는 3-methylbutanoic acid 함량이 다른 세종류에 비해 높고 3-methylbutanoic acid 특유의 꼬린냄새는 돼지고기의 기름층으로부터 나는 unclean flavor 에 중요한 영향을 미치는 것으로 생각된다. 염소고기는 C5-C7 chain length의 volatile branched 및 n-chain fatty acids를 적게 함유하고 있는 반면 4-ethyloctanoc acid는 염소고기의 노린내를 내는 결정적인 화합물이었다. 4-Methyloctanoic acid는 양고기의 sweaty-muttony flavor를 내는 중요한 화합물이었으며 염소고기와는 달리 C5, C6, 그리고 C7 branched-chain fatty acids 도 상당량 함유되어 있었다. 한국산 흑염소고기와 미국산 흰염소고기 중에 들어있는 VBCFAs의 종류는 같으나, 한국산 흑염소고기가 미국산 흰염소고기 보다 노린내가 강하며 4-ethyloctanoic 의 함량도 높았다.

• 한국약용작물학회지
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• 제2권2호
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• pp.162-167
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• 1994

국내에서 자생하고 있는 광릉쥐오줌풀 및 넓은잎 쥐오줌풀의 지하부에서 지방산, 무기성분 및 휘발성 유기산의 조성을 분석한 결과는 다음과 같다. 1. 광릉 및 넓은잎 쥐오줌플의 조지방질 함량은 $3.7{\sim}4.5%$ 범위 이었고 지방산은 총11종이 동정되었는데 그중 특히 양적으로 많이 함유되어있는 linoleic acid, linolenic acid 및 palmitic acid 등은 산지에 따라 함량차이가 큰 경향을 보였다. 2. 희분함량은 $4.3{\sim}6.3%$ 이었고 무기성분중 많이 검출된 성분으로는 조규소$(SiO_2)$를 위시하여 K, Na, Ca, Mg, Al, Fe, Mn, Zn등 이었으며, Na, Fe, Zn 및 Cu 는 산지에 따라 함량차이가 큰 경향을 보였다. 3. 광릉 쥐오줌풀로 부터 분리한 산성분획으로 부터 40종의 성분을 확인하였으며 그중 dimethoxy-2-propenoic acid, 3, 4-dimethoxy benzoic acid, 4-methoxy phenyl-2-propenoic acid 이외에도 3-methyl butanoic acid(isovaleric acid), 3-methyl pentanoic acid, 2-methyl butanoic acid 등 branched-chain fatty acid 류가 양적으로 많이 검출되었다.

• 분석과학
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• 제35권6호
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• pp.229-236
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• 2022

모유의 지질대사체에 대한 연구는 축산유래 유제품의 경우와 비교하여 매우 제한적으로 이루어져 있다. 본 연구는 지용성 대사체 연구의 선행연구로서, 모유중 극성 및 비극성 지질 중의 주요 지방산 조성에 대한 세부적 정량법 및 구조동정을 목적으로 수행되었다. 인지질을 포함한 극성 지질과 비극성 지질의 분리를 위하여 silica gel을 활용한 정제법을 개발하였으며, 효과적인 methyl ester 및 pyridylcarbinol ester 유도체화 방법을 적용하여 개별 분획의 세부적 지방산조성을 분석한 결과, 16 종의 필수지방산을 확인하였으며, 이와 함께 29 종의 미량 지방산이 확인되어, 구조 분석을 실시하였다. 측쇄 지방산의 경우, 15-18 개의 탄소를 보유한 iso 및 anteiso 지방산이 주요한 것으로 확인되었다.

• 대한방사성의약품학회지
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• 제4권2호
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• pp.57-64
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• 2018

${\omega}-[^{18}F]$-Fluorohexadecanoic acid (FHA) has been used for imaging of fatty acid metabolism of myocardium. To increase retention of radiolabeled fatty acid by blocking ${\beta}$-oxidation, methyl branched analogues have been used. In this experiment, we tried to synthesize 18F-labeled ${\alpha}-$, ${\beta}-$ and ${\omega}-FHA$ for imaging of the myocardial fatty acid metabolism. We synthesized ${\alpha}-$, ${\beta}-$ and ${\omega}$-mesylated methyl hexadecanoates and labeled with $^{18}F$ by reacting with $[^{18}F]$TBAF in acetonitrile at $80^{\circ}C$ for 10 min. Methyl ester group was removed by 1 M NaOH at $80^{\circ}C$ for 5 min. The yields of ${\alpha}-[^{18}F]$ and ${\omega}-[^{18}F]FHA$ were 25.5 and 45.5%, respectively [EOS]. However, ${\beta}-[^{18}F]FHA$ was not labeled at all due to a fast elimination reaction. The biodistribution study in ICR-mice showed that ${\omega}-[^{18}F]FHA$ has higher myocardial uptake and lower liver uptake than ${\alpha}-[^{18}F]FHA$. The electron-withdrawing effect of fluorine at ${\alpha}-$ position is believed to be the major factor affecting the biodistribution.

• 대한화학회지
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• 제35권1호
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• pp.85-89
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• 1991

한국 남해안 소흑산도에서 채집한 해면 V.japonica H.로부터 통상적인tetradecanoic 및 hexadecanoic methyl ester 이외에 탄소가 홀수인 pentadecanoic, heptadecanoic methyl ester와 가지달린 12-methyltetradecanoic, 14-methylpentadecanoic, 15-methylhexadecanoic 및 14-methylhexadecanoic methyl ester가 발견되었으며, 주 sterol 성분으로는 cholesterol과 소량의 ergost-25-ene-3,5,6-triol이 검출되었다. 한편, 여수 돌산도에서 채집한 해면 H.sinapium의 주 sterol성분은 5${\alpha}$-cholestan-3${\beta}$-ol이었고 cholesterol은 소량으로 얻어졌다. 지방산으로는 팔미틴산, 팔미토레인산, 올레인산, 스테아린산 및 리놀레인산 에틸에스터 이외에 상당량의 arachidonic산 에틸에스터가 함유되어 있었다. 상기 지역에서 채집한 또 다른 해면에서는 상당량의 tetradecanoic tetradecyl 및 hexadecyl ester와 sterol 성분으로 cholesteryl acetic 및 fatty acid ester가 함유되어 있었다.

• 한국식품영양과학회지
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• 제31권2호
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• pp.177-183
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• 2002

대두 및 대두발효식품인 청국장과 된장의 cerebroside 구성성분인 지방산, 당 및 장쇄 sphingoid base들을 GC-MS로 분석하였다. Cerebroside 산-가수분해물의 지방산들을 O-TMS methylester 유도체로 만들어 분석하였으며 대두 및 청국장의 경우 2-hydroxyhexadecanoic acid(16 : 0h)가 각각 52.2% 및 62.0%로 가장 많았고 2-hydroxydocosanoic acid(22 : 0h) 및 2-hydroxytetracosanoic acid(24 : 0h)도 15.0~17.6%이었다. 그러나 된장의 경우 16 : 0h는 10.2%로 많은 감소를 보인 반면 24 : 0h는 40.9%, 22 : 0h는 23.4% 었으며 23 : 0h, 25 : 0h 및 26 : 0h도 대두 및 청국장에 비하여 많았다. Cerebroside 산-가수분해물의 장쇄 sphingoid base들은 N-acetyl-O-TMS 유도체로 분석하였으며 대두 및 청국장에서 4- trans, 8-trans-sphingadienine (d18 : 2 $\Delta$$^{4trans, 8trans}$) 는 59.9% 및 44.5%이었으며 4-hydroxy-8-trans, cis-sphingening (t18 : 1$\Delta$$^{8trans or cis}$)는 20.9% 및 35.9% 이었고 된장 cerebroside 역시 dl8 : 2$\Delta$$^{4trans, 8trans}$가 가장 많았다. 그러나 phytosphingosine(t18 : 0) 및 sphingosine 이 성질체(d18 : 1)들은 거의 보이지 않았다. 또한 된장의 경우 오랜 기간 미생물들에 의하여 발효되었지만 Aspergillus 속들의 cerebroside가 가지는 것으로 알려진 2-hydroxyoxtadec-3-enoic acid(18 : 1h) 및 9-methyl-4,8-sphingadienine 등은 발견되지 않았다. 대두, 청국장 및 된장 cerebroside의 당유도체 mass spectrum 분석 결과 99%이상이 glucose 1번 탄소가 ceramide backbone에 결합된 monoglucocerebroside 인 것으로 나타났다.

• 대한미생물학회지
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• 제35권1호
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• pp.31-40
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• 2000

Bacillus anthracis, the etiological agent of anthrax has been classified into the Bacillus subgroup I with B. cereus, B. mycoides and B. thuringiensis based on morphological and DNA similarity. DNA studies have further indicated that these species have very AT-rich genomes and high homology, indeed it has been proposed that these four sub-species be recognized as members of the one species. Several methods have been developed to obtain good differentiation between these species. However, none of these methods provides the means for an absolutely correct differntiation. The analysis of fatty acid methyl esters (FAMEs) was employed as a quick, simple and reliable method for the identification of 21 B. anthracis strains and closley related strains. The most significant differences were found between B. anthracis and B. anthracis closely related strains in FAMEs profiles. All tested strains of B. anthracis had a branched fatty acid C17:1 Anteiso A, whereas the fraction of unsaturated fatty acid Iso C17:1 w10c was found in B. anthracis closely related strains. By UPGMA clustering analysis of FAMEs profiles, all of the tested strains were classified into two clusters defined at Euclidian distance value of 24.5. The tested strains of B. anthracis were clustered together including Bacillus sp. Kyungjoo 3. However, the isolates of B. anthracis closely related spp. Rho, S10A, 11R1, CAU9910, CAU9911, CAU9912 and CAU9913 were clustered with the other group. On the basis of these results, isolates of B. anthracis Bongchon, Kyungjoo 1, 2 and Bacillus sp. Kyungjoo 3 were reclassified as a B. anthracis. It is concluded that FAMEs analysis provides a sensitive and reliable method for the identification of B. anthracis from closely related taxa.

• 한국응용과학기술학회지
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• 제18권1호
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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.

• 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.