• Title/Summary/Keyword: 31P NMR

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Melanogenesis Inhibitory Activity of Epicatechin-3-O-Gallate Isolated from Polygonum amphibium L.

  • Lee, Young Kyung;Hwang, Buyng Su;Hwang, Yong;Lee, Seung Young;Oh, Young Taek;Kim, Chul Hwan;Nam, Hyeon Ju;Jeong, Yong Tae
    • Microbiology and Biotechnology Letters
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    • v.49 no.1
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    • pp.24-31
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    • 2021
  • This study aimed to investigate the melanogenesis inhibitory activity of epicatechin-3-O-gallate (ECG) isolated from Polygonum amphibium L. ECG was isolated from the ethanol extract of P. amphibium L, and its chemical structure was determined using spectroscopic methods such as LC-ESI-MS, 1D-NMR, and UV spectroscopy. ECG inhibited the melanogenesis of B16F10 cells in a dose-dependent manner. Particularly, it decreased the melanin content by 27.4% at 200 µM concentration, compared with the control, in B16F10 cells, without causing cytotoxicity. It is noteworthy that the expression of three key proteins, including tyrosinase, tyrosinase-related protein-1 (TRP-1), TRP-2, and microphthalmia-associated transcription factor (MITF), involved in melanogenesis, is significantly inhibited by ECG. The ECG isolated in this study caused the inhibition of body pigmentation and tyrosinase activity in vivo in the zebrafish model. These results suggest that the ECG isolated from P. amphibium L. is an effective anti-melanogenesis agent.

Development and Evaluation of Non-Hydrous Skin Analogue Liquid Crystal using Thermo-Sensitivity Smart Sensor

  • Yoo, Kwang-Ho;Hong, Jae-Hwa;Eun, So-Hee;Jeong, Tae-Hwa;Jeong, Kwan-Young
    • Journal of the Korean Applied Science and Technology
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    • v.31 no.3
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    • pp.367-374
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    • 2014
  • In this study, skin permeation enhancement was confirmed by designing it to have a structure and composition similarity to the intercellular lipids that improve miscibility with skin by cross-linked lipids poloxamer. The cross-linked lipids poloxamer was synthesized and analyzed by 1H NMR that structure dose had conjugated pluronic with ceramide3. Active component is released by modification of liquid crystal structure because PPO part, large-scale molecule block of pluronic, has hydrophobic nature at skin temperature of $35^{\circ}C$. Conjugated pluronic with ceramide3 was synthesized using Pluronic F127 and p-NPC (4-nitrophenyl chloroformate) at room temperature yielded 89%. Pluronic(Ceramide 3-conjugated Pluronic) was synthesized by reaction of p-NP-Pluronic with Ceramide3 and DMAP. The yield was 51%. This cross-linked lipids poloxamer was blended and dissolved at isotropic state with skin surface lipids, phospholipid, ceramide, cholesterol and anhydrous additive solvent. Next step was preceded by ${\alpha}$-Transition at low temperature for making the structure of Meso-Phase Lamella, and non-hydrous skin analogue liquid crystal using thermo-sensitivity smart sensor, lamellar liquid crystal structure through aging time. For confirmation of conjugation thermo-sensitivity smart sensor and non-hydrous skin analogue liquid crystal, structural observation and stability test were performed using XRD(Xray Diffraction), DSC(Differential Scanning Calorimetry), PM (Polarized Microscope) And C-SEM (Cryo-Scanning Electron Microscope). Thermo-sensitivity observation by Franz cell revealed that synthesized smart sensor shown skin permeation effect over 75% than normal liquid crystal. Furthermore, normal non-hydrous skin analogue liquid crystal that not applied smart sensor shown similar results below $35^{\circ}C$ of skin temperature, but its effects has increased more than 30% above $35^{\circ}C$.

Amine and Olefin Complexes of Pt(II) Having a PCP-Pincer Ligand

  • Park, Soon-Heum
    • Bulletin of the Korean Chemical Society
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    • v.23 no.1
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    • pp.132-136
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    • 2002
  • $Pt(2,6-(Cy_2PCH_2)_2C_6H_3)(OTf)\;(OTf=CF_3SO_3^-)$ readily reacts with various amines to afford cationic amine complexes $[Pt(2,6-(Cy_2PCH_2)_2C_6H_3)(amine)](OTf)\;(amine=NH_3,\;NHMe_2,\;NHC_4H_8,\;NH_2Ph,\;NH_2(Tol-p))$ in high yields. These complexes have been fully characterized by IR, $^1H-,\;^{19}F{^1H}-,\;and\;^{31}P{^1H}-NMR$ spectroscopy, and elemental analyses. Reaction of $Pt(2,6-(Cy_2PCH_2)_2C_6H_3)(OTf)$ with acrylonitrile quantitatively produced the ${\pi}$-olefinic complex $Pt(2,6-(Cy_2PCH_2)_2C_6H_3)(CH_2=CHCN)](OTf)$ which is only stable in solution in the presence of acrylonitrile. Attempt at isolating this complex in the pure solid state was failed due to partial decomposition into $Pt(2,6-(Cy_2PCH_2)_2C_6H_3)(OTf)$ The equilibrium constants $(K_{eq}=[Pt(PCP)-(NH_2R)^+][CH_2=CHCN]/[Pt(PCP)(CH_2=CHCN)^+][NH_2R]:\;[Pt(2,6-(Cy_2PCH_2)_2C_6H_3)(CH_2=CHCN)]^++NH_2R{\rightleftarrows}[Pt(2,6-(Cy_2PCH_2)_2C_6H_3)(NH_2R)]^++CH_2=CHCN=Ph,\;p-tolyl)$ were calculated to be 0.28 (for R = Ph) and 3.1 (R = p-tolyl) at $21^{\circ}C$. The relative stability of the ${\sigma}$-donor amine versus the ${\pi}$-olefinic acrylonitrile complex has been found largely dependent upon the amine-basicity $(pK_b)$, implicating that acrylonitrile practically competes with amine in the platinum coordination sphere. On the contrary to the formation of the acrylonitrile complex, no reaction of $Pt(2,6-(Cy_2PCH_2)_2C_6H_3)(OTf)$ with other olefins such as ethylene, styrene and methyl acrylate was observed.

Kinetics of Malonyl-CoA Synthetase from Rhizobium trifolii and Evidences for Malonyl-AMP Formation as a Reaction Intermediate

  • Kang, Sang-Won;Hong, Sung-Yu;Ryoo, Hyung-Don;Rhyu, Gyung-Ihm;Kim Yu-Sam
    • Bulletin of the Korean Chemical Society
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    • v.15 no.5
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    • pp.394-399
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    • 1994
  • The catalytic mechanism of malonyl-CoA synthetase from Rhizobium trifolii was investigated by the steady state kinetics and intermediate identification. Initial velocity studies and the product inhibition studies with AMP and PPi strongly suggested ordered Bi Uni Uni Bi Ping-Pong Ter Ter system as the most probable steady state kinetic mechanism of malonyl-CoA synthetase. Michaelis constants were $0.17{\pm}0.04 {\mu}M,\;0.24{\pm}0.18 {\mu}M\;and\;0.045{\pm}0.26 {\mu}$M for ATP, malonate and CoA, respectively. The TLC analysis of the $^{32}P-labelled$ products in reaction mixture containing $[{\gamma}-^{32}P]$ ATP in the absence of CoA showed that PPi was produced after the sequential addition of ATP and malonate. Formation of malonyl-AMP, suggested as an intermediate in the kinetically deduced mechanism, was confirmed by the analysis of $^{31}P-NMR$ spectra of AMP product isolated from the $^{18}O$ transfer experiment using $[^{18}O]$malonate. Two resonances were observed, corresponding to AMP labelled with zero and one atom of $^{18}O$, indicating that one atom of $^{18}O$ transferred from $[^{18}O]$malonate to AMP through the formation of malonyl-AMP. Formation of malonyl-AMP was also confirmed through the TLC analysis of reaction mixture containing $[{\alpha}-^{32}P]$ATP. These results strongly support the ordered Bi Uni Uni Bi Ping-Pong Ter Ter mechanism deduced from the initial velocity and product inhibition studies.

Etherification of n-Butanol to Di-n-Butyl Ether over H3+xPW12-xNbxO40 (x=0, 1, 2, 3) Keggin and H6+xP2W18-xNbxO62 (x=0, 1, 2, 3) Wells-Dawson Heteropolyacid Catalysts (Keggin형 H3+xPW12-xNbxO40 (x=0, 1, 2, 3) 및 Wells-Dawson형 H6+xP2W18-xNbxO62 (x=0, 1, 2, 3) 헤테로폴리산 촉매를 이용한 n-Butanol로부터 Di-n-Butyl Ether의 제조)

  • Kim, Jeong Kwon;Choi, Jung Ho;Yi, Jongheop;Song, In Kyu
    • Korean Chemical Engineering Research
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    • v.50 no.2
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    • pp.251-256
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    • 2012
  • Etherification of n-butanol to di-n-Butyl Ether was carried out over Keggin $H_{3+x}PW_{12-x}Nb_xO_{40}$ (x=0, 1, 2, 3) and $H_{6+x}P_2W_{18-x}Nb_xO_{62}$ (x=0, 1, 2, 3) Wells-Dawson heteropolyacid catalysts. Niobium-substituted Keggin and Wells-Dawson heteropolyacid catalysts with different niobium content were prepared. Successful preparation of the catalysts was confirmed by FT-IR, ICP-AES, and $^{31}P$ NMR analyses. Their acid properties were determined by $NH_3$-TPD (Temperature-Programmed Desorption) measurements. Heteropolyacid catalysts showed different acid properties depending on niobium content in both series. The correlation between acid properties of heteropolyacid catalysts and catalytic activity was then established. Acidity of Keggin and Wells-Dawson heteropolyacid catalysts decreased with increasing niobium content, and conversion of n-butanol and yield for di-n-butyl ether increased with increasing acidity of the catalysts, regardless of the identity of heteropolyacid catalysts (without heteropolyacid structural sensitivity). Thus, acidity of heteropolyacid catalysts served as an important factor determining the catalytic performance in the etherification of n-butanol to di-n-Butyl Ether.

Lipoxygenase Inhibition and Antioxidative Activity of Flavonoids from Paeonia moutan Seeds

  • Kim, Hyo-Jin;Chung, Shin-Kyo;Park, Sang-won
    • Preventive Nutrition and Food Science
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    • v.3 no.4
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    • pp.315-319
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    • 1998
  • Previously, the methanolic extract of Paeonia moutan seeds was found to potently inhibit soybean lipoxy-genase (SLO). Hence to isolate SLO inhibitor, the defattd methaniolic extract of the seeds was consecutively partitioned wiht ether, ethyl acetate,n-butanol ,adn water. The ether souble fraction showing strong inhibitory activity against SLO was further fractionated into a strongly acidic, a weakly acidic, and a neutral fractions. The strongly acidic components of the ether extract were successively subjected to chromatography on a silica gel, Sephadex LH-20, and preparative HPLC. Four phenolic compounds were isolated , and twio of them showing a strong SLO inhibition activity were identified as luteolin (IC50=2.32$\mu\textrm{g}$/ml) and 5,6,4'-trihydroxy-7,3'- dimethoxylflavone (IC50=0.31$\mu\textrm{g}$/ml) by UV, IR, 1H-& 13C-NMR, and MS spectroscopy. In addition, two flavonoids showed significantly antioxidative activity as strong as that of of $\alpha$-tocopherol (p<0.05) in the autoxidation system of linoleic acid. These results suggest that luteolin and 5,6,4'-trihydroxy-7,3'-dimethoxy-flavone may be used as a potential source of anti-inflammatory agents with antioxidative activity.

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The transformation of ginsenosides by acid catalysis in gastric pH

  • Han, Byung-Hoon;Park, Myung-Hwan;Han, Yong-Nam;Woo, Lin-Keun;Ushio-Sankawa;Shoji-Yahara;Osamu-Tanaka
    • Archives of Pharmacal Research
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    • v.4 no.1
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    • pp.25-31
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    • 1981
  • The ginsenosides of Korean ginseng decomposed profoundly to produce artifact products of prosapogenin $A_{1}$, $A_{2}$ and $A_{3}$ from ginsenoside Rg$_{1}$, prosapogenin $C_{1}$, $C_{2}$ and $C_{3}$ from ginsenoside Re, and prosapogenin E$_{1}$, E$_{2}$ and E$_{3}$ from ginsenoside Rb$_{1}$ by the acid treatment under physiological condition such as 37.deg.C incubation in 0.1 N HCI. 2. The chemical structures of the artifact substances were determined by the analysis CMR and mass spectra of TMS derivatives as following; table omitted.

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A Study on the Preparation of Ion-Exchange Membranes with Polyphosphazenes (포스파젠 고분자를 이용한 이온교환 분리막 제조에 관한 연구)

  • Kwon, Suk-Ky;Lee, Byung-Chul
    • Applied Chemistry for Engineering
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    • v.9 no.3
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    • pp.435-439
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    • 1998
  • A new series of ion separation membrane materials based on pheonoxy and trifluoroethoxy co-substituted polyphosphazene has been designed and synthesized. The polymers were characterized by $^{31}P$ NMR, FT-IR spectroscopy, elemental analysis, and get permeation chromatography. The basic phosphazene membranes were sulfonated to obtain better hydrophilicity and ion-selectivity. The membrane from $[NP(OC_6H_4SO_3H)_{1.58}(OCH_2CF_3)_{0.42}]_n$ gave excellent values of ion transport number, area resistivity, and also ion exchange capacity, compared with the commercial membranes.

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Electrochemical Properties of Diiron Complexes wish Conjugated Chains (공액 사슬을 갖는 철 화합물의 전기화학적 특성)

  • ;Micheal b. Sponsler
    • Journal of the Korean Institute of Electrical and Electronic Material Engineers
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    • v.15 no.6
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    • pp.511-517
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    • 2002
  • The complex 1 $([Cp*Fe(CO)_2]_2-(\mu-CH=CH-CH=CH))$ which have butadiene as a bridge were synthesized from $Cp*(CO)_2FeK$ and cis-3,4-dichlorocyclobutene. The derivatives of complex 1 where one or two carbonyl groups are replaced by phosphine ligands have been prepared by photochemical substitution. The new derivatives $([Cp*Fe(L)_2]_2-(\mu-CH=CH-CH=CH))$ where L = $(Ph_2PCH_2CH_2PPh_2)$ and $([Cp*Fe(CO)(L)]_2-(\mu-CH=CH-CH=CH))$ where L : $PPh_3$ have been characterized from $^^1H-$, $^^13C-$,$^^31P-NMR$ and elemental analysis. Obtained complexes have been studied in electrochemical experiment and UV/VIS-near-IR. The mixed-valence radical cation forms of complex 2, 3 species were found to be delocalized as the Class III. Based on the separation of the waves ($\triangle E$ : 0.470 ~ 0.605 V), the efficiency of electronic communication between two metal centers of cation species leading to stabilization relative to neutral species. The phosphine-substitute complexes (2, 3) displays two reversible oxidation waves and oxidation state of metal centers-dependent color change, electrochromism, was observed from yellow to orange and deep blue in methylene chloride.

Polycyclotriphosphazene Derivative Grafted and NanometerY2O3 Doped SPEEK Composite Membrane for DMFC

  • Li, Xia;Guo, Qiang;Zhang, Tianjiao;Qian, Junzhi;Tan, Xiaolin
    • Journal of the Korean Chemical Society
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    • v.57 no.5
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    • pp.625-633
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    • 2013
  • A type of polycyclotriphosphazene derivative (PCTPD), hexasulfanilic acid polycyclotriphosphazene (HSACP) and HSACP grafting SPEEK, sulfonated poly[2-(petachloropolycyclotriphosphazene-oxy)] etheretherketone (SPPSACPEEK) were synthesized, which were characterized by FTIR and $^{31}P$ NMR. Then three types of composite membranes such as HSACP grafting SPEEK, HSACP blending SPEEK, and nano $Y_2O_3$ doping and HSACP grafting SPEEK, respectively, were continuously prepared by solution-casting method. Comparing to SPEEK membranes with different amount of HSACP grafted or blended, grafting 15 wt% HSACP and doping 10 wt% nano $Y_2O_3$ SPEEK membrane conducted outstanding overall behavior of proton conductivity reaching $3.18 {\times}10^{-2}$ S/cm at $90^{\circ}C$ which was merely junior to SPEEK with 15 wt% HSACP grafted, methanol permeability coefficient getting $9.46{\times}10^{-8}cm^2{\cdot}s^{-1}$, swelling degree of 20.9% and solid residue of 98.98% which was superior to all specimen.