• Title/Summary/Keyword: $^{1}H$ NMR

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Antitumor Activity and Nephrotoxicity of the Novel Platinum(II) Coordination Complex (새로운 Platinum (II) Complex [Pt (II)(trans-d-dach)(DPPE)] $(NO_3)_2$의 항암효과 및 신독성에 관한 연구)

  • Jung Jee-Chang;Lee Moon-Ho;Chang Sung-Goo;Rho Young-Soo
    • The Korean Journal of Pharmacology
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    • v.31 no.1 s.57
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    • pp.103-114
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    • 1995
  • Platinum coordination complexes are currently one of the most compounds used in the treatment of solid tumors. However, its use is limited by severe side effects such as renal toxicity. Our platinum-based drug discovery program is aimed at developing drugs capable of diminishing toxicity and improving antitumor activity. We synthesized new Pt (Ⅱ) complex analogue containing 1,2-diaminocyclohexane (dach) as carrier ligand and 1,2-bis(diphenylphosphino) ethane (DPPE) as a leaving group. Furthermore, nitrate was added to improve the solubility. A new series of [Pt(trans-ddach)(DPPE).$2NO_3(PC)$ was synthesized and characterized by their elemental analysis and by various spectroscopic techniques [infrared (IR), $^{13}carbon$ nuclear magnetic resonance (NMR)]. PC demonstrated acceptable antitumor activity aganist P388, L-1210 lymphocytic leukemia cells and SK=OV3 human ovarian adenocarcinoma cells, and significant. activity as compared with that. cisplatin. The toxicity of PC was found quite less than thar of cisplatin using MTT, $[^3H]$ thymidine uptake and glucose consumption tests in rabbit proximal tubule cells, human kidney cortical cells and human renal cortical tissues. Based on these results, this novel platinum compound represent a valuable lead in the development of a new anticancer chemotherapeutic agent capable of improving antitumor activity and low toxicity.

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Development of Biologically Active Compounds from Edible Plant Sources-XIX. Isolation of Inhibitory Compound on LDL-Oxidation from the Aerial Parts of Sajabalssuk (Artemisia princeps PAMPANINI, Sajabalssuk) (식용식물자원으로부터 활성물질의 탐색-XIX. 사자발쑥(Artemisia princeps PAMPANINI, Sajabalssuk)의 전초로부터 저밀도 지질 단백질(LDL) 산화 억제물질의 분리)

  • Bang, Myun-Ho;Song, Myoung-Chong;Han, Min-Woo;Lee, Dae-Young;Jo, Jin-Kyung;Chung, Hae-Gon;Jeong, Tae-Sook;Lee, Kyung-Tae;Choi, Myung-Sook;Baek, Nam-In
    • Applied Biological Chemistry
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    • v.50 no.3
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    • pp.224-227
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    • 2007
  • Sajabalssuk (Artemisia princeps PAMPANINI) was extracted with 80% aqueous MeOH, and the concentrated extract was partitioned with EtOAc, n-BuOH and $H_{2}O$, successively. From the EtOAc fraction, two phenylpropanoids were isolated through the repeated silica gel and ODS column chromatographies. From the results of physico-chemical data including NMR, MS and IR, the chemical structures of the phenylpropanoids were determined as eugenol (1) and (-)-sesamin (2). They were the first to be isolated from Sajabalssuk (Artemisia princeps PAMPANINI, Sajabalssuk). Also, eugenol inhibited LDL-oxidation with the inhibitory activity of 87.8 ${\pm}$ 1.0% at a concentration of 40 ${\mu}g/ml$.

An Antifungal Subatance, 2,4-Diacetylphloroglucinol Produced from Antagonistic Bacterium Pseudo-monas fluorescens 2112 Against Phytophthora capsici (Phytophthora capsici를 길항하는 Pseudononas fluorescens 2112가 생산하는 항진균 항생물질 2,4-diacetylphloroglucinol)

  • 이은탁;김상달
    • Microbiology and Biotechnology Letters
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    • v.29 no.1
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    • pp.37-42
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    • 2001
  • An antifungal substance was purified from culture broth of Pseudomonas flulorescens 2112 that showed a broad-spectrum antagonistic activity against various phytopathogenic fungi including capsici. The substance was identified as 2,4-diacetylphloro-glucinol basd on NMR analysis. The 2,4-diacetylphloroglcinol showed antibiotic activity in broad acidic range from pH 1.0 to pH 9.0. About 83% of initial activity was remained after incubation for 30min ar $60^{\circ}C$, however, the activity was dropped up to 50% after 30 min incubation in $80^{\circ}C$. When the nucleotides of P. capsici treated with 2,4-diacetylphloroglucinol were labeled with[$^{3}$ H]-Adenin, the newly synthesized and radioactive-labeled RNA was significantly reduced than those of untreated P. capsici. indicating that the 2,4-diacetylphloroglucinol inhibits RNA synthesis.

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Phase Behavior and Structural Analyses of the THF + H2 Binary Clathrate Hydrate (THF + H2 이성분계 크러스레이트 하이드레이트의 상거동 및 구조 분석)

  • Cha, Jong-Ho;Park, Youngjune;Cha, Min-Jun;Yeon, Sun-Hwa;Lee, Huen
    • Korean Chemical Engineering Research
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    • v.46 no.6
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    • pp.1095-1099
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    • 2008
  • In this study, we investigated that hydrate formation and phase behavior of the $THF+H_2$ binary clathrate hydrates. In order to confirm the binary clathrate hydrate formation we employed the Raman and NMR spectroscopies that are known to be quite powerful tools, particularly for examining the cage occupancy pattern of guest molecules. In addition, we traced the P-T profiles from clathrate hydrate formation and dissociation process, which made it possible for the resulting phase equilibrium boundary to be clearly established. In the binary clathrate hydrate matrix we further identified that the relatively large THF molecules can only occupy the large $5^{12}6^4$ cavities, while the small $H_2$ molecules are entrapped in the empty $5^{12}$ cavities in structure-II, making the hydrate to be stable above 273 K even at relatively low pressure condition. Considering that pure $H_2$ hydrate can be produced at the extreme pressures higher that 1,000 bar, we can conclude that the water-soluble second guest inclusion induces $H_2$ storage and transportation to be readily achievable under much milder conditions.

Formation of New Thorium (IV) Complexes with Crown Ethers (새로운 Thorium (IV)-Crown Ether 착물형성)

  • Jung, Hak-Jin;Jung, Oh-Jin;Suh, Hyouck-Choon
    • Journal of the Korean Chemical Society
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    • v.31 no.3
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    • pp.258-270
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    • 1987
  • A series of new thorium nitrate complexes with crown ethers have been synthesized from the reaction of the hydrated thorium nitrate, with the appropriate crown ethers of different cavity sizes in various solvents such as methanol, ethanol, butanol, methylacetate, acetone, tetrahydrofuran and acetylacetone. CHN elemental analysis, ICPAS, thermal analysis and Karl-Fischer method have been used to characterize their compositions, and the spectroscopic methods of IR, UV, $^1H-NMR$, and X-ray diffraction have been employed to determine the structures and solvolysis phenomena of these complexes. and the electrical conductances were measured in DMSO, and water solvent. The solvolysis have been observed only in the complexes synthesized in acetylacetone solvent. In the solvated complexes of 15-crown-5 and 18-crown-6, the mole ratio of $Th^{4+}$: ligand : acetylacetone is found to be 1:1:1, but in the non-solvated complexes of 12-crown-4 and 15-crown-5, the mole ratios of Th:L are 1:2 and 2:3, respectively, and that in the complexes of both 18-crown-6 and dicyclohexano-18-crown-6 is 1:1. All complexes which were not solvated have shown $n{\to}{\sigma}^{\ast}$ electronic transitions of crown ether whereas complexes solvated have exhibited both $n{\to}{\sigma}^{\ast}$ of crown ether and $n{\to}{\pi}^{\ast}$ transitions of acac. The dissociation mole ratio of $Th^{4+}$ and nitrate ion is found to be 1:1 in aprotic solvent, and 1:4 in protic solvent like water.

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Isolation and Evaluation of Anti-oxidative Constituents from the Extracts of Ficus erecta var. sieboldii King Leaves (좁은잎천선과 잎 추출물 유래 항산화 활성 성분의 동정 및 효능 확인)

  • Park, Sung Hwan;Kim, Jung Eun;Yeum, Hyun Sook;Lee, Nam Ho
    • Journal of the Society of Cosmetic Scientists of Korea
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    • v.42 no.4
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    • pp.321-328
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    • 2016
  • In this study, we investigated identification of anti-oxidative constituents from Ficus erecta var. sieboldii King (F. erecta) leaves. DPPH and $ABTS^+$ radical scavenging activities were screened for the ethanol extract and solvent fractions, and ethyl acetate fraction showed the most potent scavenging activities. Five constituents were isolated from the ethyl acetate fraction of F. erecta leaves; monoolein (1), oleic acid (2), lutein (3), afzelechin (4), catechin (5). The chemical structures of the isolated compounds were elucidated based on the spectroscopic data including NMR spectra, as well as comparison of the data to the literature values. As far as we know, all of the compounds 1 ~ 5 were isolated for the first time from this plant. Studies on DPPH and $ABTS^+$ radical scavenging activities were conducted for the isolated compounds. Among them, afzelechin (4) and catechin (5) showed strong DPPH and $ABTS^+$ radical scavenging activities, whose activities were comparable to a positive control vitamin C. Also, the content of catechin isolated from this plant was determined by HPLC and it was about 3.8 mg/g for the 70% ethanol extract and 20.8 mg/g for the ethyl acetate fraction. From these results, F. erecta leaves extract could be potentially applicable as anti-oxidant ingredients in cosmetic industries.

Complex Formation of Transition and Post-Transition Metal Ions with 1,15-Diaza-3,4 : 12,13-dibenzo-5,8,11-trioxacyclooctadecane (전이 및 중금속이온과 1,15-diaza-3,4 : 12,13-dibenzo-5,8,11-trioxa-cyclooctadecane과의 착물형성)

  • Kim, Si-Joong;Lee, Myung-Jae;Koo, Chang-Hyung;Woo, Kyoun-Ja
    • Journal of the Korean Chemical Society
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    • v.35 no.6
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    • pp.645-652
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    • 1991
  • The stability constants$(K_f)$ of the complexes of some transition and post-transition metal ions (Co(Ⅱ), Ni(Ⅱ), Cu(Ⅱ), Zn(Ⅱ), Cd(Ⅱ), Pb(Ⅱ), Hg(Ⅱ)) with $N_2O_3$-donor macrocyclic ligand, 1,15-diaza-3,4 : 12,13-dibenzo-5,8,11-trioxacyclooctadecane ($NtnOdienH_4$), have been determined by potentiometry in aqueous solution at $25^{\circ}C$. Log $K_f$ values of the complexes were : Co(Ⅱ): 3.83, Ni(Ⅱ) : 4.56, Cu(Ⅱ) : 7.74, Zn(Ⅱ) : 4.98, Cd(Ⅱ) : 3.91, Pb(Ⅱ) : 6.65, and Hg(Ⅱ) : 14.87. The order of stabilities of transition metal complexes was the same as the natural order of stability proposed by Williams-Irving. In post-transition metal complexes, the order of stabilities was Cd(Ⅱ) < Pb(Ⅱ) < Hg(Ⅱ), and the covalent character in metal ion-donor atoms bonds appeared a dominant factor in the stability. In methanol solution, each metal ion forms 1 : 1 complex, while Ni(Ⅱ) ion forms both 1 : 1 and 1 : 2 complexes. It was confirmed by $^1H-$ and $^{13}C-$NMR spectral study that the nitrogen atoms in the ligand were major contributors for the complexation of post-transition metal ions with the ligand. It was shown, by elementry analysis, electrical conductivity and magnetic susceptibility measurements, and spectral analysis, that solid Cu(Ⅱ)-and Zn(Ⅱ)-complexes have a distorted octahedral and a tetrahedral structure, respectively.

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Stability Constants for Transition Metal ions of Hexadentate $N_6$ Ligands Containing Two Pyridyl Groups (피리딘을 포함하는 여섯자리 $N_6$ 리간드와 전이금속 이온 착물의 안정도상수)

  • Kim, Sun-Deuk;Kim, Jun-Kwang;Park, Yoon-Yul
    • Analytical Science and Technology
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    • v.12 no.5
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    • pp.397-402
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    • 1999
  • The open-chain hexadentate $N_6$, ligand containing two pyridyl groups, 1,15-bis(2-pyridyl)-2,6,10,14-tetraazapentadecane (bpyped) has been synthesized as its tetrahydroehloride salt and characterized by EA, IR, NMR, and Mass. Its proton dissociation constants($logK{^n}_H$) and stability constants ($log\;K_{ML}$) for Co(II), Ni(II), Cu(II) and Zn(II) ions were determined at $25^{\circ}C$ and ionic strength 0.10 M($KNO_3$) in aqueous solution by potentiometry and compared with those or analogous $N_6$ ligands contain one or two propylenic spacers, which make six-membered chelate rings, between the aliphatic nitrogen atoms.

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Analysis of Dyeing Components from Neolitsea sericea Koidz Bark (참식나무(Neolitsea sericea Koidz) 수피의 염착물질 분석)

  • Lee, Sang-Kueg;Jo, Hyun-Jin;Kim, Yun-Geun;Lee, Hak-Ju;Kang, Ha-Young
    • Journal of the Korean Wood Science and Technology
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    • v.34 no.3
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    • pp.64-72
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    • 2006
  • Two compounds were isolated from the diethylether and ethyl acetate fraction of hot water extracts by TLC and column chromatography as dyeing components. The isolated compounds were characterized as H-dibenzoquinoline-2,10-diol,5,6,6a,7-tetrahydro-1,9-dimethoxy-6-methyl (compoundI) and lyoniresinol (compoundII) by NMR and Mass spectrophotometry. To investigate if the isolated compounds are involved in the dyeing process, HPLC analysis was used. The retention time of the components from dye used in the study and the dye decolorized from the dyed substrate, silk by ethyl acetate were compared to conform the identity of those compounds. The retention time of the components from the dye and decolorized solution were identical. As a results, those two compounds were considered as dye bound to the silk.

Production of Oleamide, a Functional Lipid, by Streptomyces sp. KK90378

  • Kwon, Jeong-Ho;Hwang, Sung-Eun;Han, Jae-Taek;Kim, Chang-Jin;Rho, Jung-Rae;Shin, Jong-Eon
    • Journal of Microbiology and Biotechnology
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    • v.11 no.6
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    • pp.1018-1023
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    • 2001
  • Oleamide (cis-9-octadecenamide) is endogenous primary amide of fatty acid that is produced in small amounts in animal brains. It is known to induce sleep and to lower temperature by destroying the lipid plasma membrane structure of cells, thereby disclosing gap junction channels. To develop a new biological production method for oleamide, a screening program was conducted to isolate a microorganism producing oleamide. Among 1,500 soil microorganisms tested, KK90378 exhibited a potent positive reaction with Dragendoff`s reagent, used to detect the primary amide of oleamide. KK90378 was identified as a Streptomyces species based on cultural and morpohological characteristics, the presence of diaminopimelic acid in the cell wall, and the sugar patterns for the whole-cell extrat. Streptomyces sp. KK90378 produced oleamide 3 days after culture at $28^{\circ}C$, pH 7.2 A series of purification steps, including hexane extraction, silica gel column, and preparative thin layer chromatographies, were performed for the purification of oleamide. A spectrophotometric analysis using $^1H$, $^13C$-NMR, and GC-MS confirmed that the chemical structure of the purified oleamide was identical to that of authentic oleamide.

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