• Title/Summary/Keyword: ${\beta}$-ME

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Development of Biologically Active Compounds from Edible Plant Sources-X. -Isolation of Lipids from the Flower of Campsis grandiflora K. Schum. and their Inhibitory Effect on FPTase- (식용 식물자원으로부터 활성물질의 탐색-X. -능소화(Campsis grandiflora K. Schum.)로부터 지질화합물의 분리 및 FPTase 저해 효과 측정-)

  • Kim, Dong-Hyun;Song, Myoung-Chong;Han, Kyung-Min;Bang, Myun-Ho;Kwon, Byoung-Mog;Kim, Sung-Hoon;Kim, Dae-Keun;Chung, In-Sik;Park, Mi-Hyun;Baek, Nam-In
    • Applied Biological Chemistry
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    • v.47 no.3
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    • pp.357-360
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    • 2004
  • The flower of Campsis granudiflora K. Schum. was extracted with 80% aqueous MeOH, and the concentrated extract was partitioned with EtOAc, n-BuOH and $H_2O$. From the EtOAc fraction, four compounds were isolated through the repeated silica gel and ODS column chromatographies. From the result of physico-chemical data including NMR, MS and IR, the chemical structures of the compounds were determined as linolenic acid methyl ester, linoleic acid methyl ester, ${\beta}-sitosterol$ and daucosterol. Daucosterol inhibited FPTase activity with $IC_{50}$ values of $14{\pm}0.04\;{\mu}M$.

Development of Biologically Active Compounds from Edible Plant Sources-I. -Isolation of Major Components from the Tuber of Ipomoea batatas Lam.- (식용 식물자원으로부터 활성물질의 탐색-I. -고구마(Ipomoea batatas Lam.) 괴근 주요성분의 분리-)

  • Ahn, Eun-Mi;Bang, Myun-Ho;Kim, Hae-Yeong;Baek, Nam-In
    • Applied Biological Chemistry
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    • v.40 no.6
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    • pp.583-587
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    • 1997
  • The MeOH extracts obtained from the tuber of Ipomoea batatas Lam. were solvent-fractionated with EtOAc, n-BuOH, and $H_2O$, respectively. From EtOAc fraction four different compounds were isolated through the repeated silica gel column chromatographies. From not only the results of NMR and MS data but also the adaptation of hydrolysis, methylation, and acetylation, the chemical structures of compounds were elucidated as resin glycoside, simonin I, ${\beta}-sitosterol$, and two kinds of unsaturated fatty acids.

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Development of Biologically Active Compounds from Edible Plant Sources -XIII. Isolation of Triterpenoids from the Flower of Erigeron annuus L.- (식용 식물자원으로부터 활성물질의 탐색 -XIII. 개망초(Erigeron annuus L.) 꽃으로부터 triterpenoid의 분리-)

  • 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
    • Applied Biological Chemistry
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    • v.47 no.4
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    • pp.422-425
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    • 2004
  • 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.

Inhibitory Activity of Flavonoids from Prunus davidiana and Other Flavonoids on Total ROS and Hydroxyl Radical Generation

  • Jung, Hyun-Ah;Jung, Mee-Jung;Kim, Ji-Young;Chung, Hae-Young;Choi, Jae-Sue
    • Archives of Pharmacal Research
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    • v.26 no.10
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    • pp.809-815
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    • 2003
  • Since reactive oxygen species (ROS) and hydroxyl radicals ($^-OH$) play an important role in the pathogenesis of many human degenerative diseases, much attention has focused on the development of safe and effective antioxidants. Preliminary experiments have revealed that the methanol (MeOH) extract of the stem of Prunus davidiana exerts inhibitory/scavenging activities on 1, 1-diphenyl-2-picrylhydrazyl (DPPH) radicals, total ROS and peroxynitrites ($ONOO^-$). In the present study, the antioxidant activities of this MeOH extract and the organic solvent-soluble fractions, dichloromethane (CH$_2$Cl$_2$), ethyl acetate (EtOAc), and n-butanol (n-BuOH), and the water layer of P. davidiana stem were evaluated for the potential to inhibit $^-OH$ and total ROS generation in kidney homogenates using 2',7'-dichlorodihydrofluorescein diacetate (DCHF-DA), and for the potential to scavenge authentic $ONOO^-$. We also evaluated the inhibitory activity of seven flavonoids isolated from P. davidiana stem, kaempferol, kaempferol 7-Ο-$\beta$-D-glucoside, (+)-catechin, dihydrokaempferol, hesperetin 5-Ο-$\beta$-D-glucoside, naringenin and its 7-Ο-$\beta$-D-glucoside, on the total ROS, $^-OH$ and $ONOO^-$ systems. For the further elucidation of the structure-inhibitory activity relationship of flavonoids on total ROS and 'OH generation, we measured the antioxidant activity of sixteen flavonoids available, including three active flavonoids isolated from P. davidiana, on the total ROS and 'OH systems. We found that the inhibitory activity on total ROS generation increases in strength with more numerous hydroxyl groups on their structures. Also, the presence of an ortho-hydroxyl group, whether on the Aring or S-ring, and a 3-hydroxyl group on the C-ring increased the inhibitory activity on both total ROS and $^-OH$ generation.

Phenolic compounds from the leaves of eggplant (Solanum melongena L.) (가지(Solanum melongena L.) 잎으로부터 페놀 화합물의 분리 및 동정)

  • Baek, Dong-Ryeol;Lee, Min-Jee;Baek, Nam-In;Seo, Kyeong-Hwa;Lee, Youn-Hyung
    • Journal of Applied Biological Chemistry
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    • v.59 no.2
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    • pp.103-106
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    • 2016
  • The leaves of eggplant (Solanum melongena L.) were extracted with 80 % aqueous MeOH, and the concentrated extract was partitioned with n-hexane, EtOAc, n-BuOH, and water fractions. From the n-BuOH fraction, five compounds were isolated through the repeated silica gel, octadecyl silica gel, and Sephadex LH-20 column chromatographies. On the basis of physic-chemical and spectroscopic data including mass spectrometry, infrared spectroscopy, and nuclear magnetic resonance, they were identified to be caffeic acid (1), chlorogenic acid (2), cryptochlorogenic acid (3), panasenoside (4), and (6R,7E,9R)-4,7-megastigmadien-3-one-9-${\beta}$-${\small{D}}$-glucopyranoside (5). Compounds 3 and 4 were isolated for the first time from the leaves of S. melongena L. in this study.

Isolation of Lipids from the Aerial Parts of Spathiphyllum cannifolium (스파티필름(Spathiphyllum cannifolium) 지상부로부터 지질화합물의 분리)

  • Lee, Dae-Young;Park, Ji-Hae;Yoo, Jong-Su;Song, Myoung-Chong;Baek, Nam-In;Lee, Youn-Hyung
    • Applied Biological Chemistry
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    • v.51 no.1
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    • pp.60-64
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    • 2008
  • The aerial parts of Spathiphyllum cannifolium 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 compounds were isolated through the repeated silica gel, ODS, Sephadex LH-20 column chromatographies. From the results of physico-chemical data including NMR, MS and IR, the chemical structures of the compounds were determined as stigmasterol (1), $(2S)1-O-linolenoyl-2-0-myristoyl-3-0-{\beta}-D-galactopyranosyl-sn-glycerol$ (2) and stigmasterol glucoside (3). They were the first to be isolated from Spathiphyllum cannifolium.

Identification of Secondary Metabolites from the Stems of Viburnum erosum (덜꿩나무(Viburnum erosum)줄기로부터 이차대사산물의 분리 및 동정)

  • In, Seo-Ji;Seo, Kyeong-Hwa;Song, Na-Young;Song, Myoung-Chong;Baek, Nam-In
    • Journal of Applied Biological Chemistry
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    • v.57 no.2
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    • pp.165-170
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    • 2014
  • The stems of Viburnum erosum were extracted with 80% MeOH. The concentrated extract was partitioned with EtOAc, n-BuOH, and $H_2O$. From the EtOAc and n-BuOH fractions, four compounds were isolated through the repeated $SiO_2$, octadecyl silica gel, and Sephadex LH-20 column chromatographies. Based on NMR, MS, and IR spectroscopic data, the chemical structures were determined as betulinic aldehyde (1), koaburside (2), (6R,7E,9R)-9-hydroxymegastigma-4,7-dien-3-one-9-O-${\beta}$-D-glucopyranoside (3), and byzantionoside B (4). All the compounds were isolated for the first time from the stems of Viburnum erosum.

Kinetic Studies on the Nucleophilic Substitution Reaction of 4-X-Substituted-2,6-dinitrochlorobenzene with Pyridines in MeOH-MeCN Mixtures

  • Sung, Ryun-Youn;Choi, Ho-june;Lee, Jong-Pal;Park, Jong-Keun;Yang, Ki-Yull;Koo, In-Sun
    • Bulletin of the Korean Chemical Society
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    • v.30 no.7
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    • pp.1579-1582
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    • 2009
  • The reaction rates of 4-X-2,6-dinitrochlorobenzenes (X = $NO_2,\;CN,\;CF_3$) with Y-substituted pyridines (Y = 3-$OCH_3,\;H,\;3-CH_3,\;4-CH_3$) in methanol-acetonitrile mixtures were measured by conductometry at 25 ${^{\circ}C}$. It was observed that the rate constant increased in the order of X = 4-$NO_2\;>\;4-CN\;>\;4-CF_3$ and the rate constant also increased in the order of Y = 4-$CH_3\;>\;3-CH_3\;>\;H\;>\;3-OCH_3$. When the solvent composition was varied, the rate constant increased in order of MeCN > 50% MeOH > MeOH. The electrophilic catalysis by methanol may be ascribed to the formation of hydrogen bonds between alcoholic hydrogen and nitrogen of pyridines in ground state. Based on the transition parameters, ${\rho}_S,\;{\rho}_N,\;{\beta}_Y,\;{\rho}_{XY}$ and solvent effects, the reaction seems to proceed via $S_N$Ar-Ad.E mechanism. We also estimated the isokinetic solvent mixtures (${\rho}_{XY}$ = 0) based on cross-interaction constants, where the substituent effects of the substrate and nucleophile are compensated.

Ketene-Forming Elimination Reactions from Aryl Thienylacetates Promoted by R2NH in MeCN. Effects of Base-Solvent and β-Aryl Group

  • Pyun, Sang-Yong;Cho, Eun-Ju;Seok, Hyoun-Jung;Kim, Ju-Chang;Lee, Seok-Hee;Cho, Bong-Rae
    • Bulletin of the Korean Chemical Society
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    • v.28 no.6
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    • pp.917-920
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    • 2007
  • Ketene-forming eliminations from C4H3(S)CH2C(O)O-C6H3-2-X-4-NO2 (1) promoted by R2NH in MeCN have been studied kinetically. The reactions are second-order and exhibit Bronsted β =0.51-0.62 and |βlg|= 0.47-0.53. Hence, an E2 mechanism is evident. The Bronsted β increased from 0.33 to 0.53 and |βlg| remained nearly the same by the change of the base-solvent from Bz(i-Pr)NH/Bz(i-Pr)NH2+ in 70 mol% MeCN(aq) to Bz(i-Pr)NH-MeCN, indicating a change to a more symmetrical transition state with similar extents of Cβ -H and Cα -OAr bond cleavage. When the β-aryl group was changed from thienyl to phenyl in MeCN, the β value increased from 0.53 to 0.73 and |βlg| decreased from 0.53 to 0.43. This indicates that the transition state became skewed toward more Cβ -H bond breaking with less Cα-OAr bond cleavage. Noteworthy is the greater double bond stabilizing ability of the thienyl group in the ketene-forming transition state.

In Vitro Anti-bacterial and Anti-inflammatory Effects of Six Types of Herb Aqueous Extracts (일부 살충해독유(殺蟲解毒類) 한약의 Staphylococcus aureus에 대한 시험관 내 항균 및 항염 효과)

  • Jang, Se-Ran;Kim, Dong-Chul
    • The Journal of Korean Obstetrics and Gynecology
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    • v.27 no.1
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    • pp.81-100
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    • 2014
  • Objectives: The object of this study was to observe the in vitro anti-bacterial and anti-inflammatory effects of six single aqueous herbal extracts-Quisqualis Fructus (QuF), Meliae Cortex (MeC), Arecae Semen (ArS), Crassirhizomae Rhizoma (CrR), Ulmi Pasta Semen(UlS), Torreyae Semen(ToS)- against Staphylococcus aureus (S. aureus) and Lipopolysaccharide(LPS)-activated Raw 264.7 cells. Methods: Anti-bacterial activities against S. aureus of aqueous extracts of QuF, MeC, ArS, CrR, UlS and ToS were detected using standard agar microdilution methods. In addition, the effects on the cell viability, prostaglandin $E_2$ ($PGE_2$), nitric oxide (NO), tumor necrosis factor-${\alpha}$ (TNF-${\alpha}$), interleukin (IL)-$1{\beta}$ and IL-6 productions of LPS activated Raw 264.7 cells were detected. The anti-bacterial and anti-inflammatory effects were respectively compared with lincomycin and piroxicam. Results: Minimal Inhibition Concentration (MIC) of aqueous extracts of QuF, MeC, ArS, CrR, UlS and ToS against S. aureus was respectively detected $5.625{\pm}4.075$ (3.125~12.500), $0.332{\pm}0.273$ (0.098~0.782), $1.094{\pm}0.428$ (0.782~1.563), $2.969{\pm}2.096$ (0.782~6.250), $9.375{\pm}4.419$ (3.125~12.500)>25 mg/ml. MIC of lincomycin was detected as $0.469{\pm}0.297$ (0.195~0.782) ${\mu}g/ml$ at same conditions. In addition, $ED_{50}$ against LPS-induced cell viabilities and cytokine releases of QuF, MeC, ArS, CrR, UlS and ToS was as follows - Cell viability: 66.370, 2.908, 1.747, 259.553, 18.150 and 34.160 mg/ml; NO production: 389.486, 0.294, 0.138, 523.060, 45.363 and 49.327 mg/ml; $PGE_2$ production: 114.271, 0.223, 0.046, 243.078, 8.829 and 28.947 mg/ml; TNF-${\alpha}$ production: 406.288, 0.343, 0.123, 9404.227, 125.406 and 140.775 mg/ml; IL-$1{\beta}$ production: 117.178, 0.135, 0.019, 237.451, 7.923 and 19.418 mg/ml; IL-6 production: 31.261, 0.105, 0.055, 128.434, 2.290 and 3.745 mg/ml. ED50 of piroxicam against LPS-induced cell viabilities, NO, $PGE_2$, TNF-${\alpha}$, IL-$1{\beta}$ and IL-6 were detected as 35.179, 6.552, 1.162, 7.273, 7.101 and $5.044{\mu}g/ml$, respectively at same conditions. Conclusions: All six single aqueous herbal extracts showed anti-bacterial effects against S. aureus, in the order of MeC, ArS, CrR, QuF and UlS aqueous extracts except for ToS; they did not showed any anti-bacterial effects (MIC>25 mg/ml). They also showed anti-inflammatory effects against LPS-activated Raw 264.7 cells in the order of ArS, MeC, UlS, ToS, QuF and CrR aqueous extracts. It means that the ArS and MeC will be showed favorable potent anti-bacterial and related anti-inflammatory effects.