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Neuroprotective Compounds Isolated from Lysimachia christinae

  • Gahee Ryu;Choong Je Ma
    • Natural Product Sciences
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    • v.29 no.1
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    • pp.10-16
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    • 2023
  • We previously reported that dried Lysimachia christinae whole plant extract exerted significant neuroprotective activity. In this study, we tried to isolate neuroprotective compounds of L. christinae. We evaluated the neuroprotective activity of the four fractions (hexane, chloroform, ethyl acetate, and n-butanol fractions) of methanol extract. Among them, ethyl acetate and n-butanol fractions showed most potent neuroprotective activity against glutamate excitotoxicity. Nine compounds were isolated from ethyl acetate and n-butanol fractions of L. christinae extract and identified as cynaroside (1), (3,4,5,6-tetrahydroxytetrahydro-2H-pyran-2-yl)methyl-3-hydroxy-2-octyldopentaconta-23,33-dienoate (2), androst-16-ene-3,6-diol (3), 2-hydroxy-24-propoxytetracos-4-enoic acid (4), 2-hydroxy-24-methoxytetracos-4-enoic acid (5), 12-(stearoyloxy)octadec-9-enoic acid (6), β-sitosterol (7), (E)-4-(3,4-dimethoxyphenyl)but-3-en-1-yl palmitate (8) and (1S,2S,3R,4R)-4-(((2S,3R,4R,5R,6S)-2-(((2R,3R,4S,5R,6R)-2-(3,4-dimethoxyphenethoxy)-3,5-dihydroxy-6-(hydroxymethyl) tetrahydro-2H-pyran-4-yl)oxy)-4,5-dihydroxy-6-methyltetrahydro-2H-pyran-3-yl)oxy)cyclohexane-1,2,3-triol (9) by spectroscopic data such as UV, IR, NMR, Mass spectroscopy. Their neuroprotective activity was evaluated by MTT assay. Cynaroside (1) and androst-16-ene-3,6-diol (3) had significant neuroprotective activity against glutamate-injured HT22 cells. The neuroprotective efficacy of cynaroside (1) and androst-16-ene-3,6-diol (3) was related to their anti-oxidative activity.

R3V6 Amphiphilic Peptide with High Mobility Group Box 1A Domain as an Efficient Carrier for Gene Delivery

  • Ryu, Jaehwan;Jeon, Pureum;Lee, Minhyung
    • Bulletin of the Korean Chemical Society
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    • v.34 no.12
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    • pp.3665-3670
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    • 2013
  • The R3V6 peptide includes a hydrophilic arginine stretch and a hydrophobic valine stretch. In previous studies, the R3V6 peptide was evaluated as a gene carrier and was found to have low cytotoxicity. However, the transfection efficiency of R3V6 was lower than that of poly-L-lysine (PLL) in N2A neuroblastoma cells. In this study, the transfection efficiency of R3V6 was improved in combination with high mobility group box 1A domain (HMGA). HMGA is originated from the nuclear protein and has many positively-charged amino acids. Therefore, HMGA binds to DNA via charge interaction. In addition, HMGA has a nuclear localization signal peptide and may increase the delivery efficiency of DNA into the nucleus. The ternary complex with HMGA, R3V6, and DNA was prepared and evaluated as a gene carrier. First, the HMGA/DNA complex was prepared with a negative surface charge. Then, R3V6 was added to the complex to coat the negative charges of the HMGA/DNA complex, forming the ternary complex of HMGA, R3V6, and DNA. A physical characterization study showed that the ternary complex was more stable than the PLL/DNA complex. The HMGA/R3V6/DNA complex had a higher transfection efficiency than the PLL/DNA, HMGA/DNA, or R3V6/DNA complexes in N2A cells. Furthermore, the HMGA/R3V6/DNA complex was not toxic to cells. Therefore, the HMGA/R3V6/DNA complex may be a useful gene delivery carrier.

MicroRNA-22 negatively regulates LPS-induced inflammatory responses by targeting HDAC6 in macrophages

  • Youn, Gi Soo;Park, Jong Kook;Lee, Chae Yeon;Jang, Jae Hee;Yun, Sang Ho;Kwon, Hyeok Yil;Choi, Soo Young;Park, Jinseu
    • BMB Reports
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    • v.53 no.4
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    • pp.223-228
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    • 2020
  • Dysregulation of histone deacetylase 6 (HDAC6) can lead to the pathologic states and result in the development of various diseases including cancers and inflammatory diseases. The objective of this study was to elucidate the regulatory role of microRNA-22 (miR-22) in HDAC6-mediated expression of pro-inflammatory cytokines in lipopolysaccharide (LPS)-stimulated macrophages. LPS stimulation induced HDAC6 expression, but suppressed miR-22 expression in macrophages, suggesting possible correlation between HDAC6 and miR-22. Luciferase reporter assays revealed that 3'UTR of HDAC6 was a bona fide target site of miR-22. Transfection of miR-22 mimic significantly inhibited LPS-induced HDAC6 expression, while miR-22 inhibitor further increased LPS-induced HDAC6 expression. LPS-induced activation of NF-κB and AP-1 was inhibited by miR-22 mimic, but further increased by miR-22 inhibitor. LPS-induced expression of pro-inflammatory cytokines such as TNF-α, IL-1β, and IL-6 was inhibited by miR-22 mimic, but further increased by miR-22 inhibitor. Taken together, these data provide evidence that miR-22 can downregulate LPS-induced expression of pro-inflammatory cytokines via suppression of NF-κB and AP-1 axis by targeting HDAC6 in macrophages.

2D-QSAR Analyses on The Tyrosinase Inhibitory Activity of 2-[(2,6-Dioxocyclohexyl)methyl]-cyclohexane-1,3-dione Analogues (2-[(2,6-Dioxocyclohexyl)methyl]cyclohexane-1,3-dione 유도체의 Tyrosinase 저해활성에 관한 2D-QSAR 분석)

  • Kim, Sang-Jin;Sung, Nack-Do
    • Journal of the Society of Cosmetic Scientists of Korea
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    • v.40 no.4
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    • pp.383-390
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    • 2014
  • The following conclusion was made from the 2D-QSAR model for the tyrosinase inhibitory activity according to the variation of the substituents R1 and R2 in analogues of compound 2-[(2,6-dioxocyclohexyl)methyl]cyclohexane- 1,3-dione (1-23). The best optimized 2D-QSAR model was $Obs.pI_{50}=-0.295({\pm}0.031)TDM$ $-0.120({\pm}0.014)DMZ+0.135({\pm}0.050)DMX.R_2+6.382({\pm}0.17)$, and the correlation $r^2=0.905$) of which was greater than its predictability ($q^2=0.843$). The magnitude of the effect of tyrosinase inhibitory activities was in order of TDM > $DMX.R_2{\geq}DMZ$, and it tended to increase as the hydrophobicity of substrate molecule (ClogP > 0) as well as the steric favor of substituent $R_1$ increased. The analysis of the model implies that inhibitory activity of substrate molecule will increase as $DMX.R_2$ (Dipole moment X component of $R_2$-substituent) increases, while TDM (Total Dipole Moment) and DMZ(Dipole Moment of Z-Component) decrease. As such, it is deemed feasible to conclude, that in order to increase the inhibitory effect, it would be rather desirable to replace the polar groups within the molecules with non-polar functional groups.

Formation of Mo(NAr)(PMe₃)₂Cl₃and Mo₂(PMe₃)₄Cl₄from Reduction of Mo(NAr)₂Cl₂(DME) with Mg in the Presence of PMe₃[Ar=2,6-diisopropylphenyl]

  • 정건수;박병규;Lee, Soon W.
    • Bulletin of the Korean Chemical Society
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    • v.18 no.2
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    • pp.213-217
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    • 1997
  • Magnesium reduction of Mo(N-C6H3-2,6-i-Pr2)2Cl2(DME) in the presence of trimethylphosphine led to a mixture of Mo(N-C6H3-2,6-i-Pr2)(PMe3)2Cl3, 1, and Mo2(PMe3)4Cl4, 2. In solution 1 is slowly air-oxidized to Mo(N-2,6-i-Pr2-C6H3)(OPMe3)(PMe3)Cl3, 3. 1 is chemically inert to carbon nucleophiles (ZnMe2, ZnEt2, AlMe3, AlEt3, LiCp, NaCp, TlCp, NaCp*, MeMgBr, EtMgBr), oxygen nucleophiles (LiOEt, LiO-i-Pr, LiOPh, LiOSPh), and hydrides (LiBEt3H, LiBEt3D). Crystal data for 1: orthorhombic space group P212121, a=11.312(3) Å, b=11.908(3) Å, c=19.381(6) Å, Z=4, R(wR2)=0.0463 (0.1067). Crystal data for 2: monoclinic space group Cc, a=18.384(3) Å, b=9.181(2) Å, c=19.118(3) Å, b=124.98(1)°, Z=4, R(wR2)=0.0228 (0.0568). Crystal data for 3: orthorhombic space group P212121, a=11.464(1) Å, b=14.081(2) Å, c=16.614(3) Å, Z=4, R(wR2)=0.0394 (0.0923).

Reactivity of the Biheterocyclic Betaine with the para-Substituted Phenacyl Bromides for the Ring Transformation Reaction

  • Yoo, Kyung-Ho;Kim, Dong-Jin;Kim, You-Seung;Park, Sang-Woo
    • Bulletin of the Korean Chemical Society
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    • v.9 no.3
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    • pp.164-166
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    • 1988
  • 7-Dithiocarboxy-3-phenyl-5,6-dihydro imidazo[2,1-b]thiazolium-betaine (2) was prepared by treatment of 3-phenyl-5,6-dihydro imidazo[2,1-b]thiazole (1) with carbon disulfide in acetone at room temperature. On the reaction of 2 with para-substituted phenacyl bromides (4) having the electron withdrawing property by virtue of (+) resonance (R) < (-) inductive (I) or (-) resonance (R), (-) inductive (I) effect, ring transformation product p-substituted-2-[2-[7-(p-substituted benzoyl)-5-thioxo-2,3-dihydro-1H-imidazo[1,2-c] thiazol-1-yl]-2-phenylvinylthio] acetophenone (6) was obtained; however, when R is electron donating grops with (+) resonance (R) > (-) inductive (I) effect the quarternary ammonium salt 7-(p-substituted phenyl) carbonyl methyl-3-phenyl-5,6-dihydro imidazo [2,1-b] thiazolium bromide (8) is formed. The reaction of 2 with unsubstituted-phenacyl bromide (R = H), on the other hand, gives 6a and 8a to the similar ratio, respectively.

A Study on the Prediction and Evaluation of Road Traffic Noise at the Apartment Housing Complex depending on the Types of Adjacent Roads (인접도로의 유형에 따른 공동주택 주거단지의 도로교통소음 전달영향 및 평가)

  • Baek, Geon-Jong;Jang, Gil-Soo;Baek, Eun-Sun
    • KIEAE Journal
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    • v.9 no.1
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    • pp.61-68
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    • 2009
  • In this study, computer simulation program was using to identify the effects of road traffic noise propagation depending on the road types which are very variable in dense city. To achieve this goal, the roads should adjacent to housing complex were categorized into 7 types and propagation noise level should predicted then after simulation of noise exposure population calculation are carried out. Followings the results. First, the road types producing the higher noise level are R1, R2, R3 and R7. The lowest one is R6. And R4, R5 showed that some amount of noise level reduction. Second. the R6 road type which is tunnel shaped showed the highest noise level reduction in vertical distance gap. Last, the order of noise exposure population ratio is R1>R2>R7 and R6 showed the lowest.

Evaluation to Purification Capacity of Pollutants by Column Test with the tidal flat sediment (통수실험에 의한 갯벌의 오염물질 정화능력 평가)

  • Kim, Jong-Gu;You, Sun-Jae
    • Journal of Environmental Science International
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    • v.9 no.3
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    • pp.223-228
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    • 2000
  • The purpose of this study is to evaluate the purification capacity of pollutants by column test with the tidal flat sediment. Sediment materials were taken from Chunjangdae tidal flat which located in Chungnam Seochungun. The column tests were conducted on four conditions(R1 : raw sewage filtered by G2 filter, R2 : sterilized sewage after filtered by GF/C filter, R3 : R2 /filtered(membrane) seawater (1:1), R4 : R2 /filtered(membrane) seawater(1:2)). The results of this study may be summarized as followed ; The removed COD by column tests were increased according to increasing the quantity of sewage. During the column tests of 580min, the total removed ammonia nitrogen were 90.1mg for R1, 81.0mg for R2, 27.6mg for R3 and 4.1mg for R4. The result was similar to COD experiment. During the 580min, the total removed total-phosphates were 3.4mg for R1, 4.2mg for R2, 5.6mg for R3 and 2.0mg for R4. The removal efficiency of Pb and Cd for R3 and R4 reactor were higher than R1 and R2 reactor. The remove of heavy metal by the column test was high in sample with seawater. But in the initial 20min, the adsorbed Pb and Cd showed about 3% of the total adsorbed Pb and Cd during 580min.

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Decay Rate and Nutrients Dynamics during Decomposition of Oak Roots (상수리나무 뿌리 분해 및 분해과정에 따른 영양염류 변화)

  • 문형태
    • The Korean Journal of Ecology
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    • v.27 no.3
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    • pp.165-171
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    • 2004
  • Weight loss and nutrients dynamics during decomposition of oak roots (diameter classes: R₁〈0.2㎝, 0.5㎝〈R₂〈1㎝, 1㎝〈R₃〈2㎝, 2㎝.〈R₄〈4㎝) (Quercus acutissima) were studied for 33-months in Kongiu, Korea. After 33-months, decomposition rate of R₁, R₂, R₃ and R₄ was 49.6%, 47.5%, 66.4% and 66.1%, respectively. The decomposition constant(k) for R₁, R₂, R₃, and R₄ was 0.249/yr, 0.234/yr, 0.397/yr and 0.393/yr, respectively. Larger diameter class of the root lost more weight than smaller diameter class. N concentration in decomposing oak roots increased in all diameter classes. After 33-months, remaining N in R₁, R₂, R₃ and R₄ was 66.5%, 80.7%, 84.4% and 44.4%, respectively. K concentration in decomposing oak roots decreased in early part of decomposition and then increased in later stage of decomposition. After 33-months, remaining P in R₁, R₂, R₃ and R₄ was 64.7%, 62.4%, 93.1% and 30.7%, respectively. K concentration in decomposing oak roots decreased rapidly in early stage of decomposition. Remaining K in R₁, R₂, R₃ and R₄ was 11.6%, 10.6%, 5.9% and 7.7%, respectively. Ca concentration in decomposing oak roots showed different among diameter classes. After 33-months, remaining Ca in R₁, R₂, R₃ and R₄ was 66.2%, 51.0%, 39.1% and 48.3%, respectively. Initial concentration of Mg in oak root was higher in smaller diameter class. After 33-months, remaining Mg in R₁, R₂, R₃ and R₄ was 15.3%, 29.9%, 24.5% and 69.4%, respectively.