• Bulletin of the Korean Chemical Society
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• v.34 no.2
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• pp.558-564
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• 2013

A simple and effective method is introduced to synthesize a series of polystyrene-b-poly(oligo(ethylene oxide) monomethyl ether methacrylate)-b-polystyrene (PSt-b-POEOMA-b-PSt) triblock copolymers. The structures of PSt-b-POEOMA-b-PSt copolymers were characterized by Fourier-transform infrared spectroscopy (FTIR) and nuclear magnetic resonance ($^1H$ NMR) spectroscopy. The molecular weight and molecular weight distribution of the copolymer were measured by gel permeation chromatography (GPC). Furthermore, the self-assembling and drug-loaded behaviours of three different ratios of PSt-b-POEOMA-b-PSt were studied. These copolymers could readily self-assemble into micelles in aqueous solution. The vitamin E-loaded copolymer micelles were produced by the dialysis method. The micelle size and core-shell structure of the block copolymer micelles and the drug-loaded micelles were confirmed by dynamic light scattering (DLS) and transmission electron microscopy (TEM). The thermal properties of the copolymer micelles before and after drug-loaded were investigated by different scanning calorimetry (DSC). The results show that the micelle size is slightly increased with increasing the content of hydrophobic segments and the micelles are still core-shell spherical structures after drug-loaded. Moreover, the glass transition temperature (Tg) of polystyrene is reduced after the drug loaded. The drug loading content (DLC) of the copolymer micelles is 70%-80% by ultraviolet (UV) photolithography analysis. These properties indicate the micelles self-assembled from PSt-b-POEOMA-b-PSt copolymers would have potential as carriers for the encapsulation of hydrophobic drugs.

• Journal of the Korean Society of Food Science and Nutrition
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• v.31 no.3
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• pp.511-515
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• 2002

Paeoniae radix has been considered as one of the most important crude drugs used in traditional oriental medicine and has been employed as a circulatory tonic in care of weakness, night sweats, and lumbar pain, etc. Platelet activation plays an important role in thrombosis and haemostasis. Active compounds for the inhibition of platelet activation from Paeoniae radix were extracted and fractionated into five fractions. Its fraction two and three of ethyl acetate extract inhibited the aggregation of washed rabbit platelets induced by collagen. Two active compounds, bezoyloxypaeoniflorin and paeoniflorin, were isolated from fraction two and three by silica gel column and high performance liquid chromatography. The chemical structures were determined by comparison of their proton and carbon nuclear magnetic resonance spectra. Benzoyloxypaeoniflorin showed strong inhibition at the concentration of 100 ug/mL against collagen-induced washed rabbit platelets aggregation. It is suggested that Paeoniae radix has become food material to prevent a cardiovascular disease.

• Korean Journal of Pharmacognosy
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• v.36 no.3 s.142
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• pp.235-239
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• 2005

Changes in chemical composition of the ethanolic extract of roasted Asparagi Tuber were investigated by HPLC. One dramatically increased peak $(t_R\;14.85 min)$ was isolated by silica gel column chromatograph and identified as 5-hydroxymethyl furfural (HMF) by comparing its $1^H-NMR$ data with that of a commercial standard. HMF content reached its maximum level at $190^{\circ}C$ for 60 minutes. Under these conditions, HMF contents in the roasted Asparagi Tuber was increased about thirteen times (9.26mg/g) over the not-roasted control (0.71 mg/g). No significant differences were found in macrophage-activating, prolyl endopeptidase-inhibiting, antioxidative (DPPH), anti-coagulating (activated partial thromboplastin times), and ACE-inhibiting activities between roasted and not-roasted Asparagi Tuber.

• 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 $35^{\circ}C$.

• Journal of the Korean Society of Food Science and Nutrition
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• v.27 no.5
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• pp.813-820
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• 1998

This study was performed as a part of comparative biochemical studies of carotenoid pigment for the fresh water fish. Carotenoids in integument of Korean dark sleeper, Odontobutis platycephala, and dark sleeper, Odontobutis odontobutis interrupta, which are all the Korean native fresh water fish, were separated by thin layer chromatography, column chromatography and HPLC. The separated carotenoid were then reduced and isomerized by NaBH4 and I2 respectively to investigate UV-Vis spectrophotometeric patterns and chracterized by IR, 1H-NMR and Mass spectrum. The content of total carotenoids in the integument of Korean dark sleeper was 3.01mg% in April, but it was increased to 3.74mg% in September at the near of spawning period. The carotenoid isolated in April consisted of $\beta$-carotene(25.6%), lutein(18.5%) and zeaxanthin(12.0%) as major carotenoids and also contained isocryptoxanthin, diatoxanthin, tunaxanthin, cynthiaxanthin, canthaxanthin and $\alpha$-cryptoxanthin as minor carotenoids. Similarly, in September the carotenoid consisted of $\beta$-carotene(16.5%), zeaxanthin(13.7%) and cynthiaxanthin(13.6%) as major carotenoids and also contained lutein, isocryptoxanthin, tunaxanthin, $\alpha$-cryptoxanthin, diatoxanthin and canthaxanthin as minor carotenoids. At the near of spawning period, the content of cynthiaxanthin and $\alpha$-cryptoxanthin were increased. The content of total carotenoids in the integument of spawning period. T도 carotenoid isolated in April and September consisted of $\beta$-carotene(24.9%, 27.5%), zeaxanthin(14.4%, 20.9%) and lutein(12.6%, 11.4%) as major carotenoids and also contained cynthiaxanthin, tunaxanthin, diatoxanthin, isocryptoxanthin, $\alpha$-cryp-toxanthin and canthaxanthin as minor carotenoids. At the near of spawning period, the content of zeaxanthin was increased, indicating that the carotenoid composition were dependent upon their living conditions and their integument colors. Both Korean dark sleeper and dark sleeper contained high amount of cynthiaxanthin and diatoxanthin which are found as rare carotenoids in the other of fresh water fish. It is interes that they also contained tunaxanthin which is a specific carotenoid in marine fishes.

• Bulletin of the Korean Chemical Society
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• v.18 no.11
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• pp.1166-1172
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• 1997

[FeⅢ(BLPA)DBC]BPh4, a new functional model for the catechol dioxygenases, has been synthesized, where BLPA is bis((6-methyl-2-pyridyl)methyl)(2-pyridylmethyl)amine and DBC is 3,5-di-tert-butylcatecholate dianion. The BLPA complex has a structural feature that iron center has a six-coordinate geometry with N4O2 donor set. It exhibits EPR signals at g=5.5 and 8.0 which are typical values for the high-spin FeⅢ (S=5/2) complex with axial symmetry. The BLPA complex reacts with O2 within a few hours to afford intradiol cleavage (75%) and extradiol cleavage (15%) products which is very unique result of all [Fe(L)DBC] complexes studied. The iron-catecholate interaction of BLPA complex is significantly stronger, resulting in the enhanced covalency of the metal-catecholate bonds and low energy catecholate to FeⅢ charge transfer bands at 583 and 962 nm in CH3CN. The enhanced covalency is also reflected by the isotropic shifts exhibited by the DBC protons, which indicate increased semiquinone character. The greater semiquinone character in the BLPA complex correlates well with its high reactivity towards O2. Kinetic studies of the reaction of the BLPA complex with 1 atm O2 in CH3OH and CH2Cl2 under pseudo-first order conditions show that the BLPA complex reacts with O2 much slower than the TPA complex, where TPA is tris(2-pyridylmethyl)amine. It is presumably due to the steric effect of the methyl substituent on the pyridine ring. Nevertheless, both the high specificity and the fast kinetics can be rationalized on the basis of its low energy catecholate to FeⅢ charge transfer bands and large isotropic NMR shifts for the BLPA protons. These results provide insight into the nature of the oxygenation mechanism of the catechol dioxygenases.

• The Journal of Korean Medicine Ophthalmology and Otolaryngology and Dermatology
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• v.16 no.1
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• pp.94-99
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• 2003

Objectives : Gram-positive bacteria have became increasing resistant to antibacterial agents, and hence multi-drug-resistant bacterial pathogens are now a major problem in clinical medicine. There is, therefore, a need for new antibacterial agents. In the course of our screening program for potent antibacterial agent from medicinal plants, the extract of Salvia miltiorrhiza (S. miltiorrhiza) showed antibacterial activity against methcillin resistant Staphylococcus aureus (MRSA) and antibiotic-resistant S. aureus. Methods : S. miltiorrhiza was extracted with 80$\%$ EtOH. The extract was suspended in H2O and fractionated successively with hexane chloroform, ethyl acetate, and n-buthanol. The chloroform fraction, which showed the highest antibacterial activity(MICs, 78㎍/ml) against MRSA, was chromatographed on a silica gel column and recycling prep-LC to give the pure antibacterial component. Results and Conclusions : The second fraction among the chloroform soluble portion of an aqueous EtOH extract of S. miltiorrhiza root showed outstanding antibacterial activity against MRSA and antibiotic-resistant S. aureus compared to the other fraction. An active compound was isolated from the second fraction using silica gel column chromatoraphy and recycling prep-LC. Based on these data together with the IH-, 13C-NMR, mass and mp, the active compounds were identified tanshinone Ⅰ, dehydrotanshinone Ⅰ and cryptotanshinone. Among tanshinones, cryptotanshinone and dihydrotanshinone Ⅰ MICs against MRSA and antibiotics-resistant S. aureus were 12.5, 12.5 and 6.3㎍/ml, respectively.

• YAKHAK HOEJI
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• v.29 no.2
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• pp.62-69
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• 1985

The isomeric intermediates, $3{\alpha}$and $3{\beta}-amino-5{\alpha}-cholestane required for the synthesis of N-nitrosoureas, N-(2-chloroethyl)-N-nitrosocarbamoyl-$3{\alpha}-amino-5{\alpha}$-cholestane (9), N-methyl-N-nitrosocarbamoyl-3${\alpha}-amino-5{\alpha}-cholestane$ (10), N-(2-chloroethyl)-N-nitrosocarbamoyl-$3{\beta}-amino-5{\alpha}-cholestane$: (7), and N-methyl-N-nitrosocarbamoyl-$3{\beta}-amino-5{\alpha}-cholestane$ (8) were obtained through the $LiAlH_{4}$ reduction of $5{\alpha}$-cholestan-3-one oxime, followed by the chromatographic separation: the assignment of the stereochemistry of both isomers were based on the shape and chemical shift of $C_{3}$-proton resonances on their NMR spectra and on the elution mobility on the TLC. The urea intermediates, N-(2-chloroethyl) carbamoyl-3.alpha.-amino-5.alpha.-cholestane (13), N-methylcarbamoyl-$3{\alpha}-amino-5{\alpha}-cholestane$ (14), N-(2-chloroethyl) carbamoyl-$3{\beta}-amino-5{\alpha}-cholestane (11) and N-methyl-$3{\beta}-amino-5{\alpha}$-cholestane (12) were prepared by the treatment of each isomers ($3{\alpha}$-amino-and $3{\beta}-amino-5{\alpha}$-cholestane) with alkyl isocyanates in anhydrous $CHCl_{3}$, and the corresponding nitrosoureas, 7-10 were obtained by the nitrosation of the ureas, 11-14, with AcOH (or HCOOH)/$NaNO_{2}$ in ice-cold condition. The inhibitory activity of the nitrosoureas, 7-10, and their intermediates, 12-14 towards the growth of L1210 murine leukemia cells, were examined. Among them, the compounds 9 and 10 exhibited high activity having $ED_{50}$ to be 5.5g/ml and 6.1g/ml, respectively.

• Journal of Microbiology and Biotechnology
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• v.33 no.12
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• pp.1606-1614
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• 2023

Biochemical gut metabolism of dietary bioactive compounds is of great significance in elucidating health-related issues at the molecular level. In this study, a human gut bacterium cleaving C-C glycosidic bond was screened from puerarin conversion to daidzein, and a new, gram-positive C-glycoside-deglycosylating strain, Dorea sp. MRG-IFC3, was isolated from human fecal sample under anaerobic conditions. Though MRG-IFC3 biotransformed isoflavone C-glycoside, it could not metabolize other C-glycosides, such as vitexin, bergenin, and aloin. As evident from the production of the corresponding aglycons from various 7-O-glucosides, MRG-IFC3 strain also showed 7-O-glycoside cleavage activity; however, flavone 3-O-glucoside icariside II was not metabolized. In addition, for mechanism study, C-glycosyl bond cleavage of puerarin by MRG-IFC3 strain was performed in D₂O GAM medium. The complete deuterium enrichment on C-8 position of daidzein was confirmed by ¹H NMR spectroscopy, and the result clearly proved for the first time that daidzein is produced from puerarin. Two possible reaction intermediates, the quinoids and 8-dehydrodaidzein anion, were proposed for the production of daidzein-8d. These results will provide the basis for the mechanism study of stable C-glycosidic bond cleavage at the molecular level.

• Journal of the Korean Chemical Society
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• v.37 no.6
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• pp.612-617
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• 1993

Some vanadium(III) complexes have been prepared from the reaction of VC$l_3$ with N, P, O-donating ligands and characterized by elemental analysis, $^1$H-NMR infrared and UV-Visible spectroscopy. 3,5-Lutidine, 1,2-phenylenediamine, 8-hydroxyquinoline, 9,10-phenanthrenequinone, triphenylphosphine, 1,2-bis(diphenylphosphino)ethane, 1,3-bis(diphenylphosphino)propane and 1,1'-bis(diphenylphosphino)ferrocene were chosen as coordinating ligands. Stretching frequency ${\nu}g$(V-Cl) of complexes appears) at 298∼367 cm-1, which show octahedral geometries. Stretching frequency of ${\nu}g$(V-X) (X = N, P, O) indicates that ligands are coordinated to vanadium(III). Stretching frequency ${\nu}g(C{\equiv}N)$ of acetonitrile in these complexes are characteristically shifted to about 70 c$m^{-1}$ higher compared with that of a free ligand (2260 c$m^{-1}$). Bending frequency of $\delta(C{\equiv}N)$ is also shifted to about 60 c$m^{-1}$ higher compared with that of a free ligand (377 c$m^{-1}$). Finally each vanadium(III) complex showed the following formulation; [VC$l_3$(L)$_2$MeCN] or [VC$l_3$(L-L)MeCN].