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천연자원으로부터 아실코에이: 콜레스테롤아실 전달효소 저해제의 탐색
김미경,권병목,배기환,최돈하,이학주,김홍은,김영국,Kim, Mi-Kyung,Kwon, Byoung-Mog,Bae, Ki-Hwan,Choi, Don-Ha,Lee, Hak-Ju,Kim, Hong-Eun,Kim, Young-Kook 한국생약학회 1999 생약학회지 Vol.30 No.4
Acyl-CoA: Cholesterol Acyltransferase (ACAT) is a key enzyme responsible for cholesteryl ester formation in atherogenesis and in cholesterol absorption from the intestines. In addition under pathological conditions, formation and accumulation of cholesteryl ester as lipid droplets by ACAT within macrophages constitute a characteristic feature of early lesions of atherosclerotic plaques. ACAT inhibitors are expected to be effective for treatment of atherosclerosis and hypercholesterolemia. ACAT inhibitors of natural origin have been rarely reported. In our screening program for ACAT inhibitors, 303 plants were extracted with methanol or ethanol, and screened for the inhibitory activity against ACAT from the rat liver microsome. Extracts of 13 plants including Quercus aliena, Diospyros kaki, Platycarya strobilacea and Hibiscus syriacus inhibited more than 90% of ACAT activity and 43 samples in alcohol extracts such as Magnolia obovata and Panax ginseng also inhibited more than 70% of ACAT activity at a concentration of $100\;{\mu}g/ml$.
수종의 국화과 식물에서 분리한 Sesquiterpene Lactone들의 생리활성(제3보) -Nitric oxide 방출 및 ACAT 저해활성-
장대식,박기훈,고학룡,이현선,권병목,양민석,Jang, Dae-Sik,Park, Ki-Hun,Ko, Hack-Lyong,Lee, Hyun-Sun,Kwon, Byoung-Mog,Yang, Min-Suk 한국생약학회 1999 생약학회지 Vol.30 No.1
Nine sesquiterpene lactones, which were isolated from Hemisteptia lyrata Bunge, Chrysanthemum zawadskii Herbich var. latilobum Kitamura and Chrysanthemum boreale Makino were evaluated for the inhibition upon the nitric oxide release from the Raw cell and for the ACAT (acyl Co A: cholesterol acyltransferase) inhibitory assay. In the nitric oxide release inhibitory experiment, hemistepsin B $(IC_{50}\;=\;0.05\;{\mu}g/ml,\;0.15\;{\mu}M),$ cumambrin B, tulipinolide and costunolide exhibited strong inhibition with $IC_{50}$ values $0.05\;{\mu}g/ml\;(0.15\;{\mu}M),\;0.1\;{\mu}g/ml\;(0.38\;{\mu}M),\;0.2\;{\mu}g/ml\;(0.69\;{\mu}M)$ and $0.2\;{\mu}g/ml(0.86\;{\mu}M),$ respectively. In the ACAT inhibitory assay, angeloylcumambrin B, tigloylcumambrin B, tulipinolide and costunolide exhibited strong inhibition with $IC_{50}$ values $33\;{\mu}g/ml\;(95.4\;{\mu}M),\;22\;{\mu}g/ml\;(63.6\;{\mu}M),\;38\;{\mu}g/ml\;(151\;{\mu}M)$ and $17\;{\mu}g/ml(73.3\;{\mu}M),$ respectively, whereas other compounds did not exhibit significant activity against ACAT above $100\; {\mu}g/ml.$.
방면호,장태오,송명종,김동현,권병목,김영국,이현선,정인식,김대근,김성훈,박미현,백남인,Bang, Myun-Ho,Jang, Tae-O,Song, Myoung-Chong,Kim, Dong-Hyun,Kwon, Byoung-Mog,Kim, Young-Kuk,Lee, Hyun-Sun,Chung, In-Sik,Kim, Dae-Keun,Kim, Sung-Hoon,Par 한국응용생명화학회 2004 Applied Biological Chemistry (Appl Biol Chem) Vol.47 No.2
식용식물자원으로부터 활성소재를 찾기 위하여 흰씀바귀 뿌리를 80% MeOH로 추출하고, 얻어진 추출물을 EtOAc, n-BuOH및 $H_2O$로 용매 분획하였다. EtOAc와 n-BuOH 분획에 대하여 column chromatography를 반복하여 4종의 화합물을 분리하였다. 각각에 대하여 2D-NMR을 포함한 스펙트럼 데이터의 해석과 문헌 자료를 조사하여 zaluzanin C (1), $9{\alpha}-hydroxyguaian-4(l5),10(14),11(13)-triene-6,12-olide$ (2), $3{\beta}-O-{\beta}-D-glucopyranosyl-8{\beta}-hydroxyguaian-4(15),\;10(14 )-diene-6,12-olide$ (3), $3-O-{\beta}- D-glucopyranosyl-8{\beta}hydroxyguaian-10(14)-ene-6,12-olide$ (4)로 구조를 결정하였다. 이들 화합물에 대하여 ACAT(Acyl-CoA: cholesterol acyltransferase), DGAT (diacylglycerol acyltransferase) 및 FPTase(farnesyl-protein transferase)의 활성에 미치는 억제효과를 측정하였다. Compound 1과 Compound 2는 DGAT에 대한 활성억제효과에 있어서 $IC_{50}$ 값이 각각 0.13 mM, 0.10 mM로 나타났고, FPTase에 대하여는 각각 0.15 mM, 0.18 mM로 나타났으며, ACAT에 대하여는 약한 억제 활성을 나타냈다. 따라서 흰씀바귀는 항암 및 항고혈압의 소재 개발에 있어서 유용한 자원으로 활용될 수 있을 것이다. The root of lxeris dentata forma albiflora was extracted with 80% aqueous MeOH and solvent fractionated with EtOAc, n-BuOH and water, successively. From the EtOAc and n-BuOH fractions, four sesquiterpene compounds were isolated through the repeated silica gel and ODS column chromatographies. The chemical structures were determined as zaluzanin C (1), $9{\alpha}-hydroxyguaian-4(l5),10(14),11(13)-triene-6,12-olide$ (2), $3{\beta}-O-{\beta}-D-glucopyranosyl-8{\alpha}-hydroxyguaian-4(15),10(14 )-diene-6,12-olide$ (3), and $3{\beta}-O-{\beta}- D-glucopyranosyl-8{\beta}hydroxyguaian-10(14)-ene-6,12-olide$ (4) through the interpretation of several spectral data including 2D-NMR. Some showed the inhibitory effects on DGAT (Diacylglycerol acyltransferase), ($IC_{50}$ values of 1, 2: 0.13, 0.10 mM), the catalyzing enzymes of the intracellular esterification of diacylglycerol and FPTase (Famesyl-protein transferase), ($IC_{50}$ values of 1, 2: 0.15, 0.18 mM), the farnesylation enzyme for Ras protein charge of cancer promotion.
두충(Eucommia ulmoides O.)잎으로부터 Grb2-Shc 결합저해 활성물질의 분리
한재택,안은미,방면호,남지연,권병목,백남인,Hahn, Jae-Taek,Ahn, Eun-Mi,Bang, Myun-Ho,Nam, Ji-Youn,Kwon, Byoung-Mog,Baek, Nam-In 한국생약학회 1999 생약학회지 Vol.30 No.2
The MeOH extracts obtained from the leaves of Eucommia ulmoides were solvent-fractionated with EtOAc, n-BuOH, and $H_20$, successively. From the EtOAc extract showing Grab2-Shc inhibitory activity, a flavonol and a lignan compounds were isolated through repeated silica gel column chromatographies. By interpretation of several spectral data and adaptation of acetylation method, the chemical structures of the compounds were determined as 5,7,3',4'-tetrahydroxy-flavonol (quercetin), and 4,4',8',9-tetrahydroxy-3,3'-dimethoxy-7,9'-cyclolignan {(-)-olivil)}, respectively. The compounds exhibited $IC_{50}$ values in Grb2-Shc inhibitory activity to be 93 and $210\;{\mu}mole/l$, respectively.
식용식물자원으로부터 활성물질의 탐색-XVII. 산딸나무(Cornus kousa Burg.)의 열매로부터 sterol 화합물의 분리
이대영,송명종,유종수,김성훈,정인식,김대근,박미현,권병목,김세영,백남인,Lee, Dae-Young,Song, Myoung-Chong,Yoo, Jong-Su,Kim, Sung-Hoon,Chung, In-Sik,Kim, Dae-Keun,Park, Mi-Hyun,Kwon, Byoung-Mog,Kim, Se-Young,Baek, Nam-In 한국응용생명화학회 2006 Applied Biological Chemistry (Appl Biol Chem) Vol.49 No.1
산딸나무 열매를 100% MeOH로 추출하고, 얻어진 추출물을 EtOAc, n-BuOH 및 물로 용매 분획 하였다. 이 중 EtOAc 분획으로부터 silica gel과 octadecyl silica gel(ODS) column chromatography를 반복하여 3종의sterol 화합물을 분리, 정제하였다. 각 화합물의 화학구조는 NMR, MS 및 IR 등의 스펙트럼 데이터를 해석하여, ${\beta}-sitosterol$(1), $stigmast-4-en-6{\beta}-ol-3-one$(2), daucosterol(3)으로 동정하였다. 이 화합물들은 산딸나무에서 처음 분리되었다. The fruits of Cornus kousa Burg. were extracted with 80% aqueous MeOH, and the concentrated extract was partitioned with EtOAc, n-BuOH and $H_2O$, successively. From the EtOAc fraction, three sterols were isolated through the repeated silica gel and ODS column chromatographies. According to the results of physico-chemical data including NMR, MS and IR, the chemical structures of the compounds were determined as ${\beta}-sitosterol$ (1), $stigmast-4-en-6{\beta}-ol-3-one$ (2) and daucosterol (3). They were the first to be isolated from Cornus kousa Burg.
식용식물자원으로부터 활성물질의 탐색-XII. - 꽃마리(Trigonotis peduncularis Benth.)로부터 Flavonol 배당체의 분리 및 hACAT1 저해활성 -
양혜정,송명종,방면호,이진희,정인식,이윤형,정태숙,권병목,김성훈,김대근,박미현,백남인,Yang, Hye-Joung,Song, Myoung-Chong,Bang, Myun-Ho,Lee, Jin-Hee,Chung, In-Sik,Lee, Youn-Hyung,Jeong, Tae-Sook,Kwon, Byoung-Mog,Kim, Sung-Hoon,Kim, Dae-Keu 한국응용생명화학회 2005 Applied Biological Chemistry (Appl Biol Chem) Vol.48 No.1
꽃마리를 80% MeOH로 추출하고, 얻어진 추출물을 EtOAc, n-BuOH 및 $H_2O$로 용매 분획하였다. EtOAc와 n-BuOH 분획에 대하여 column chromatography를 반복하여 4종의 flavonol 배당체를 분리하였다. 각각에 대하여 2D-NMR을 포함한 스펙트럼 데이터의 해석과 문헌 자료를 조사하여 $kaempferol-3-O-{\beta}-{D}-glucopyranoside(astragalin),\;kaempferol-3-O-{\alpha}-{L}-rhamnopyranosyl(1{\rightarrow}6)-{\beta}-{D}-glucopyranoside(nicotiflorin),\;quercetin-3-O-{\alpha}-{L}-rhamnopyranosyl(1{\rightarrow}6)-{\beta}-{D}-glucopyranoside(rutin),\;quercetin-3-O-{\beta}-{D}-glucopyranoside(isoquercitrin)$로 구조를 결정하였다. 이 화합물들은 꽃마리에서는 이번에 처음 분리, 보고되었다. 또한 $nicotiflorin(100\;{\mu}g/ml)$은 hACAT1에 대하여 $68.3{\pm}1.2%$ 저해활성을 나타내었다. The MeOH extracts obtained from whole plant of Trigonotis peduncularis Benth. were solvent fractionated using EtOAc, n-BuOH and water, successively. The EtOAc and n-BuOH fractions gave four flavonol glycosides through application of silica gel and octadecyl silica gel (ODS) column chromatographies. The chemical structures of the flavonol glycosides were determined by the interpretation of several spectral data including 2D-NMR as $kaempferol-3-O-{\beta}-{D}-glucopyranoside\;(astragalin,\;1),\;kaempferol-3-O-{\alpha}-{L}-rhamnopyranosyl\;(1{\rightarrow}6)-{\beta}-{D}-glucopyranoside\;(nicotiflorin,\;2),\;quercetin-3-O-{\alpha}-{L}-rhamnopyranosyl(1{\rightarrow}6)-{\beta}-{D}-glucopyranoside\;(rutin,\;3),\;quercetin-3-O-{\beta}-{D}-glucopyranoside\;(isoquercitrin,\;4)$. The flavonoids have been first isolated from this plant. Nicotiflorin $(100\;{\mu}g/ml)$ showed $68.3{\pm}1.2%$ of the inhibitory effect on hACAT1(human Acyl CoA: cholesterol transferase 1) activity.
식용 식물자원으로부터 활성물질의 탐색 -XIII. 개망초(Erigeron annuus L.) 꽃으로부터 triterpenoid의 분리-
김동현,정성제,방명호,정인식,김성훈,권병목,김대근,박미현,백남인,Kim, Dong-Hyun,Jung, Sung-Je,Bang, Myun-Ho,Chung, In-Sik,Kim, Sung-Hoon,Kwon, Byoung-Mog,Kim, Dae-Keun,Park, Mi-Hyun,Baek, Nam-In 한국응용생명화학회 2004 Applied Biological Chemistry (Appl Biol Chem) Vol.47 No.4
개망초의 꽃을 80% MeOH 용액으로 추출하고, 추출물을 EtOAc, n-BuOH 및 물로 분배, 추출하였다. 이 중 EtOAc 분획을 silica gel, octadecylsilica gel(ODS) column chromatography 및 high performance liquid chromatography(HPLC)로 정제하여 3종의 화합물을 분리하였다. 각 화합물의 화학구조는 NMR, MS 및 IR 등의 스펙트럼 데이터를 해석하여, ${\alpha}-amyrenone(1),\;{\alpha}-amyrin(2)$ 및 ${\beta}-amyrin(3)$으로 동정하였다. 이들 3종의 triterpenoid는 개망초에서는 처음 분리되었다. The flower of Erigeron annuus L. was extracted with 80% aqueous MeOH, and the concentrated extract was partitioned with EtOAc, n-BuOH and $H_2O$, successively. From the EtOAc fraction, three compounds were isolated through the repeated silica gel, ODS column and high performance liquid chromatographies. From the result of physico-chemical data including NMR, MS and IR, the chemical structures of the compounds were determined as ${\alpha}-amyrenone,\;{\alpha}-amyrin\;and\;{\beta}-amyrin$. These three compounds were isolated for the first time from the flower of Erigeron annuus L.
오미자에서 분리한 새로운 Chitin Synthase Ⅱ 저해제인 Gomisin N 과 Wuweizisu C
황의일(Eui Il Hwang),김미경(Mi Kyung Kim),이향복(Hyang Bok Lee),김영국(Young Kook Kim),권병목(Byoung Mog Kwon),배기환(Ki Hwan Bae),김성욱(Sung Uk Kim) 대한약학회 1999 약학회지 Vol.43 No.4
To search for new chitin biosynthesis inhibitors from natural sources, several higher plants were examined the inhibitory activity against chitin synthase Ⅱ by enzymatic assay. Among them, the extract of Schizandra chinensis strongly showed the inhibitory activity against chitin synthase Ⅱ. Gomisin N and wuweizisu C were isolated from Schizandra chinensis and showed IC50 value of 62.4mcg/ml and 19.2mcg/ml, respectively. Activities of these compounds were more stronger than that of polyoxin D. However, gomisin N and wuweizisu C showed weakly antifungal activities against various human pathogens.