염기 처리된 montmorillonite를 이용한 다이머산 메틸에스테르의 합성

육정숙(Jeong Suk Yuk),신지훈(Jihoon Shin),김영운(Young-Wun Kim) 한국트라이볼로지학회 2019 한국윤활학회지(윤활학회지) Vol.35 No.2

In this study, we demonstrate the effects of the acidic properties of montmorillonite (MMT), which is commonly used as a catalyst, on the conversion and selectivity of the dimer acid methyl ester (DAME) synthesis. We synthesize DAME by the dimerization of conjugated linoleic acid methyl ester (CLAME) and oleic acid methyl ester using MMT KSF. Incidentally, trimer acid methyl ester was formed as a by-product during the DAME synthesis. There is a necessity to adequately adjust the strength and quantity of the acid site to control the selectivity of DAME. Therefore, we vary the pH of the MMT acid by using various metal hydroxides. The purpose of this study is to increase the yield of monocyclic dimer acid methyl ester, which is a substance with adequate physical properties for industrial applications (e.g., lubricant and adhesive, etc.), using a heterogeneous catalyst. We report the dimerization of fatty acid methyl ester by using base treated-KSF, and apply it to conjugated soybean oil methyl ester. Then, we transmute the acid site properties of KSF, such as pH of 5 wt.% slurry KSF and various alkali metals (Li, Na, K, Ca). Characterization of base treated-KSF using a pH meter, x-ray diffraction, inductively coupled plasma-atomic emission spectrometer, Brunauer–Emmett–Teller surface analysis, and temperature-programmed desorption. We conduct an analysis of CLAME and DAME using nuclear magnetic resonance spectroscopy, gas chromatography, and gel permeation chromatography. Through these experiments, we demonstrate the effects of the acidic properties of KSF on the conversion and selectivity of the DAME synthesis, and evaluate its industrial potential by application to waste vegetable oil.

항진균성 지의류 내생 곰팡이 및 항진균성 물질의 탐색

천다미,장다솜,김혜영,최갑성,최상기,Cheon, Da-Mi,Jang, Da Som,Kim, Hye Young,Choi, Kap Seong,Choi, Sang Ki 한국미생물학회 2013 미생물학회지 Vol.49 No.2

순천대학교 지의류 은행(Lichen Bioresources Center)에서 571종의 지의류 내생 곰팡이를 분양받아 Candida albicans에 대한 항진균 활성을 조사하여 4종을 선정하였다. 선정된 4종의 지의류 내생 곰팡이의 배양액 내에 존재하는 항진균 활성을 알아보기 위해 disc diffusion method 방법을 이용한 결과 Stereocaulon sp. (1429,1430)가 C. albicans에 대한 항진균 활성이 가장 좋았으며, 다음으로는 Graphis sp. (1245), Cryptosporiopsis diversispora (0156) 순으로 활성이 좋게 나타났으며, 이들 지의류 내생곰팡이가 고체배지와 액체배지에서도 항진균 활성 물질을 생성하였다. 고체배지에서와 액체배지에서 공통적으로 활성이 있는 지의류 내생 곰팡이 배양액의 chloroform, ethyl acetate 용매 추출물의 C. albicans의 항진균 활성도를 측정한 결과 4종 모두 chloroform 추출물에서 높은 활성도를 나타냈다. Candida albicans, Candida glabrata, Candida tropicalis, Candida lusitaniae에 대한 항진균 활성은 Stereocaulon sp. (1429, 1430)의 chloroform 추출물에서 모두 98% 이상의 높은 저해율을 보였고 Stereocaulon sp. (1429) 배양액의 chloroform 추출액과 ethyl acetate 추출액을 GC/MS를 이용해 성분을 분석한 결과 hexadecanonic acid-methyl ester, 14-octadecenoic acid-methyl ester, octadecenoic acid-methyl ester가 새로운 항진균 물질일 가능성을 보여주었다. To isolate a novel antifungal compound, we obtained 571 kinds of endolichenic fungi from Lichen Bioresources Center and examined their antifungal abilities. Four fungi Stereocaulon sp. (1429), Stereocaulon sp. (1430), Cryptosporiopsis sp. (0156), and Graphis sp. (1245) showed high antifungal activity against Candida albicans when they grew in both liquid and solid media. We extracted the culture supernatants of these fungi with chloroform and then ethyl acetate. The chloroform fraction exhibited the highest anti-fungal activities when those fractions were examined for the growth inhibition of Candida albicans with disc diffusion method. To see information for the inhibitor present in chloroform fraction we employed GC-MS for the fractions of Stereocaulon sp. (1429). We found that hexamethylcyclotrisiloxane, decanoic acid, hexadecanonic acid-methyl ester, 14-octadecenoic acid-methyl ester, and octadecenoic acid-methyl ester were present more in chloroform fraction than in ethylacetate fraction. This indicates that those compounds could be possible antifungal candidates since antifungal activity of chloroform extract was two times higher than that of ethyl acetate extract.

청겨자채 추출물의 뇌조직 내 Oxidative Stree 억제활성물질의 동정

이근종,김미리,심재석,황재관 한국식품영양과학회 2001 한국식품영양과학회지 Vol.30 No.5

마우스 뇌조직에서 지질과산화를 막아주는 것으로 알려진 청겨자채에 대해서 50%MeOH 추출물(2mg/mL)을 사용하여 소 뇌조직의 산화적스트레스를 유발한 ascorbate/Fe$^{3+}$ system에서 항산화 활성을 조사하였다. 청겨자채 추출물의 용매순차추출 후 TBARS 활성을 각각 용매 분획(100)$\mu\textrm{g}$/mL)별로 확인한 결과 각각의 용매 분획 중 n-BiOH 분획 (49%)이 가장 높았고, EtOAc(40%), H$_{2}$O(9%) 및 n-hexane (0%) 순이었다. n-BuOH 분획을 silica gel column chroma-tography를 반복하였으며, CE, TLC를 통해서 sinapic acid와 ferulic acid를 확인하였다. CE를 통하여 그 함량을 정량한 결과, 건조중량(g)당 sinapic acid는 24.3 ppm 이었고 ferulic acid는 42.8 ppm으로 나타났다. 최종 정제활성물질을 $^{1}$J-NMR(CDCL$_{3}$)와 $^{13}$C-NMR(CDCL$_{3}$)로 확인하였으며 sinapic acid methyl ester, ferulic acid acid와 ferulic acid와 RF치가 일치하는지 여부를 TLC상에서 비교하였다. 동일한 50$\mu\textrm{g}$/mL 농도에서 sinapic acid methyl ester는 40%, ferulic acid methyl ester 는 35%의 항산화 활성을 나타내었으며 이것은 시판되는 표준물질은 sinapic acid(22%)와 ferulic acid (18%)에 비해 약간 높게 나타났다. 이것은이 화합물에 라디칼을 소거하는 작용기와 관계가 있는 것으로 여겨진다. 청겨자채 추출물 중에도 항산화 활성이 비교적 널리 분포된 것으로 보아 이 성분들은 체내에서 단독으로 또는 상호작용으로 항산화 작용을 나타낼 것으로 예상된다. Green mustard leves were found to effectively prevent lipid peroxidation of bovine-brain tissue by ascor-bate/Fe system, The 50% methanol extracts mustard leaves were separated into four solvent faction using n-hexane,. EtOAc, n-BiOH and water. Then n-BiOH fraction exclusively exhibited the antioxidative activities at concentration above 100 $\mu\textrm{g}$/mL/ The n-BuOH fraction was further isolated to a single compound using TLC analysis and silica gel chromatography. The active antiodidative compounds were identified as sinapic acid methyl ester and ferulic acid methyl ester by $^{1}$H-NMR and $^{13}$ C-NMR, The sinapic acid methyl ester and ferulic acid methyl ester were prepared by methylating of sinapic acid and ferulic acid with diazomethane. The results strongly suggested that sinapic acid and ferulic acid could be emplyed as a potential antioxiative agents for preventing the bovine brain lipid peroxidation. lipid peroxidation.

1,4-Dihydropyridine의 Dialkylaminomethyl화 유도체의 합성

서정진(Jung Jin Suh),홍유화(You Hwa Hong) 대한약학회 1989 약학회지 Vol.33 No.5

When 2,6-Dimethyl-4-(3''-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid 3-mono methyl ester(3) was reacted with dimethyl methylene ammonium chloride (5a) and K2CO3 in DMF, 2,6-dimethyl-4-(3''-nitrophenyl)-5-(N,N-dimethylamino)methyl-1,4-dihydropyridine-3-carboxylic acid methyl ester (6a) was obtained in 41% yield. As the same procedure with compound (3) and the other dialkylaminomethylating reagents (5b, c, d, e), 2,6-dimethyl-4-(3''-nitrophenyl)-5-(N,N-diethylamino)methyl-1,4-dihydropyridine-3-carboxylic acid methylester(6b), 2,6-dimethyl-4-(3''-nitrophenyl)-5-(1''-pyrrolidinyl)methyl-1,4-dihydropyridine-3-carboxylic acid methyl ester (6c), 2,6-dimethyl-4-(3''-nitrophenyl)-5-(1''-piperidinyl)methyl-1,4-dihydropyridine-3-carboxylic acid methyl ester (6d) and 2,6-dimethyl-4-(3''-nitrophenyl)-5-(1''-morpholinyl)methyl-1,4-dihydropyridine-3-carboxylic acid methyl ester (6e) were obtained in 28%, 49%, 48% and 18% yield respectively.

Production of 12-hydroxy dodecanoic acid methyl ester using a signal peptide sequence-optimized transporter AlkL and a novel monooxygenase

Yoo, Hee-Wang,Kim, Joonwon,Patil, Mahesh D.,Park, Beom Gi,Joo, Sung-yeon,Yun, Hyungdon,Kim, Byung-Gee Elsevier 2019 Bioresource technology Vol.291 No.-

<P><B>Abstract</B></P> <P>In this study, a signal peptide of AlkL was replaced with other signal peptides to improve the soluble expression and thereby facilitate the transport of dodecanoic acid methyl ester (DAME) substrate into the <I>E. coli</I>. Consequently, AlkL with signal peptide FadL (AlkL<SUB>f</SUB>) showed higher transport activity toward DAME. Furthermore, the promoter optimization for the efficient heterologous expression of the transporter AlkL<SUB>f</SUB> and alkane monooxygenase (AlkBGT) system was conducted and resulted in increased ω-oxygenation activity of AlkBGT system. Moreover, bioinformatic studies led to the identification of novel monooxygenase from <I>Pseudomonas pelagia</I> (Pel), which exhibited 20% higher activity towards DAME as substrate compared to AlkB. Finally, the construction of a chimeric transporter and the expression of newly identified monooxygenase enabled the production of 44.8 ± 7.5 mM of 12-hydroxy dodecanoic acid methyl ester (HADME) and 31.8 ± 1.7 mM of dodecanedioic acid monomethyl ester (DDAME) in a two-phase reaction system.</P> <P><B>Highlights</B></P> <P> <UL> <LI> Bioconversion ofdodecanoic acid methyl esterintovalue-addedchemicals. </LI> <LI> Introduce host-based signal peptide to enhance expression level of transporter. </LI> <LI> Maximize product production by controlling the expression level of multi enzymes. </LI> <LI> Found novel enzymes with good activity to dodecanoic acid methyl ester. </LI> </UL> </P> <P><B>Graphical abstract</B></P> <P>[DISPLAY OMISSION]</P>

Effects of Enzyme Type and Molar Ratio on Enzymatic Synthesis of Hydroxybutyrate Methyl Ester

Jemin SON,Kyeonga KIM,Seungmee LEE,Hah Young YOO,Chulhwan PARK 한국생물공학회 2021 한국생물공학회 학술대회 Vol.2021 No.10

Ketone bodies are energy supplements produced from fatty acids by the liver under energy restriction conditions. In recent studies, several clinical effects, such as the increase of cardiac energetics and potential uses as a treatment for cancer and cardiovascular disease, are observed when the ketone body concentration in the blood is maintained over 0.5 mM. Appropriate ingestion ways of ketone bodies are investigated, and ketone esters were recognized as the most effective ingestion way. Hydroxybutyrate methyl ester, one of ketone esters, can effectively increase ketone body concentration in the blood with fewer doses than other options and are shown several clinical effects as ketone bodies and also as itself. Through ingestion of hydroxybutyrate methyl ester, the learning and memory was improved and further, the possibility for the treatment of Alzheimer’s disease was also observed. But still, only few studies are investigated the production of hydroxybutyrate methyl ester. Therefore, the conditions for the production of hydroxybutyrate methyl ester based on enzymes were designed under the consideration of productivity.

Response of Soil Microbial Communities to Different Cultivation Systems in Controlled Horticultural Land

이유석,강정화,최경주,이성태,김은석,송원두,이영한 한국토양비료학회 2011 한국토양비료학회지 Vol.44 No.1

Ester-linked fatty acid methyl ester (EL-FAME) profiles were used to describe differences in soil microbial communities influenced by conventional farming system (CFS), and organic farming system (OFS) in controlled horticultural land. Soil physicochemical properties and soil microbial communities were determined in the experimental fields. Higher organic matter content in OFS reduced soil bulk density which in turn increased the soil porosity. Generally, soil chemical properties in OFS were higher than those of CFS, but EC value in OFS was significantly lower than that of CFS. With the exception of Fe content, other macronutrient contents and pH in both farming system decreased with the soil depth. Soil microbial biomass of OFS was approximately 1.3 times in topsoil and 1.8 times in subsoil higher than those of CFS. Lower ratios of cy17:0to 16:1ω7c and cy19:0 to 18:1ω7c were found in the CFS soils than the OFS soils, indicating that microbial stress decreased. The ratio of MUFA to SFA was higher in OFS due to organic input to the soil. In principal components analysis (PCA), the first variable accounted for 54.3%, while the second for 27.3%, respectively. The PC1 of the PCA separated the samples from CFS and OFS, while the PC2 of the PCA separated the samples from topsoil and subsoil. EL-FAMEs with the positive eigenvector coefficients for PC1 were cy17:0 to 16:1ω7c ratio, cy19:0 to 18:1ω7c ratio, soil pH, soil organic matter, and soil NO_3-N content. Our findings suggest that the shifting cy19:0 to 18:1ω7c ratio should be considered as potential factors responsible for the clear microbial community differentiation observed between different cultivation systems and soil depth in controlled horticultural land.

Response of Soil Microbial Communities to Different Cultivation Systems in Controlled Horticultural Land

You-Seok Lee,Jeong-Hwa Kang,Kyeong-Ju Choi,Seong Tae Lee,Eun-Seok Kim,Eun-Seok Kim,Young Han Lee 한국토양비료학회 2011 한국토양비료학회지 Vol.44 No.1

Ester-linked fatty acid methyl ester (EL-FAME) profiles were used to describe differences in soil microbial communities influenced by conventional farming system (CFS), and organic farming system (OFS) in controlled horticultural land. Soil physicochemical properties and soil microbial communities were determined in the experimental fields. Higher organic matter content in OFS reduced soil bulk density which in turn increased the soil porosity. Generally, soil chemical properties in OFS were higher than those of CFS, but EC value in OFS was significantly lower than that of CFS. With the exception of Fe content, other macronutrient contents and pH in both farming system decreased with the soil depth. Soil microbial biomass of OFS was approximately 1.3 times in topsoil and 1.8 times in subsoil higher than those of CFS. Lower ratios of cy17:0 to 16:1ω7c and cy19:0 to 18:1ω7c were found in the CFS soils than the OFS soils, indicating that microbial stress decreased. The ratio of MUFA to SFA was higher in OFS due to organic input to the soil. In principal components analysis (PCA), the first variable accounted for 54.3%, while the second for 27.3%, respectively. The PC1 of the PCA separated the samples from CFS and OFS, while the PC2 of the PCA separated the samples from topsoil and subsoil. EL-FAMEs with the positive eigenvector coefficients for PC1 were cy17: 0 to 16:1ω7c ratio, cy19:0 to 18:1ω7c ratio, soil pH, soil organic matter, and soil NO3-N content. Our findings suggest that the shifting cy19:0 to 18:1ω7c ratio should be considered as potential factors responsible for the clear microbial community differentiation observed between different cultivation systems and soil depth in controlled horticultural land.

Response of Soil Microbial Communities to Different Cultivation Systems in Controlled Horticultural Land

Lee, You-Seok,Kang, Jeong-Hwa,Choi, Kyeong-Ju,Lee, Seong-Tae,Kim, Eun-Seok,Song, Won-Doo,Lee, Young-Han Korean Society of Soil Science and Fertilizer 2011 한국토양비료학회지 Vol.44 No.1

Ester-linked fatty acid methyl ester (EL-FAME) profiles were used to describe differences in soil microbial communities influenced by conventional farming system (CFS), and organic farming system (OFS) in controlled horticultural land. Soil physicochemical properties and soil microbial communities were determined in the experimental fields. Higher organic matter content in OFS reduced soil bulk density which in turn increased the soil porosity. Generally, soil chemical properties in OFS were higher than those of CFS, but EC value in OFS was significantly lower than that of CFS. With the exception of Fe content, other macronutrient contents and pH in both farming system decreased with the soil depth. Soil microbial biomass of OFS was approximately 1.3 times in topsoil and 1.8 times in subsoil higher than those of CFS. Lower ratios of cy17:0 to $16:1{\omega}7c$ and cy19:0 to $18:1{\omega}7c$ were found in the CFS soils than the OFS soils, indicating that microbial stress decreased. The ratio of MUFA to SFA was higher in OFS due to organic input to the soil. In principal components analysis (PCA), the first variable accounted for 54.3%, while the second for 27.3%, respectively. The PC1 of the PCA separated the samples from CFS and OFS, while the PC2 of the PCA separated the samples from topsoil and subsoil. EL-FAMEs with the positive eigenvector coefficients for PC1 were cy17: 0 to $16:1{\omega}7c$ ratio, cy19:0 to $18:1{\omega}7c$ ratio, soil pH, soil organic matter, and soil $NO_3$-N content. Our findings suggest that the shifting cy19:0 to $18:1{\omega}7c$ ratio should be considered as potential factors responsible for the clear microbial community differentiation observed between different cultivation systems and soil depth in controlled horticultural land.

Pheophorbide A-methyl Ester, Acyl-CoA: Cholesterol Acyltransferase Inhibitor from Diospyros kaki

Rho, Mun-Chual,Chung, Mi-Yeon,Song, Hye-Young,Kwon, Oh-Eok,Lee, Seung-Woong,Baek, Jin-Ah,Jeune, Kyung-Hee,Kim, Koan-Hoi,Lee, Hyun-Sun,Kim, Young-Kook The Pharmaceutical Society of Korea 2003 Archives of Pharmacal Research Vol.26 No.9

In the course of our search for Acyl-CoA: cholesterol acyltransferase (ACAT) inhibitors from natural sources, a new type of ACAT inhibitor was isolated from a methanol extract of Diospyros kaki. On the basis of spectral and structural evidence, the compound was identified as pheophorbide A-methyl ester. Pheophorbide A-methyl ester inhibited ACAT activity in a dose dependent manner with an $IC_{50}$ value of 1.85 $\mu$ g/mL.