• Korean Journal of Medicinal Crop Science
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• v.24 no.6
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• pp.437-443
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• 2016

Background: Previous phytochemical studies of whole Vernonia cinerea L. plants have identified sesquiterpene lactones, sterols, and triterpenes, which possess anticancer, antifeedant, and antimalarial activities. However, there are no reports of other types of bioactive metabolites. Therefore, the present study aimed to identify phenolic compounds with anti-inflammatory activity in the aerial parts of the plant. Methods and Results: Compounds were isolated from the aerial parts of V. cinerea using a silica and C-18 gel columns and semi-preparative HPLC instrument, and the structures of the compounds were determined using one- and two- dimension nuclear magnetic resonance spectroscopy and mass spectroscopy. The chloroform soluble extracts and isolated compounds were evaluated for their anti-inflammatory potential based on their ability to inhibit nitric oxide production and $TNF-{\alpha}$ induced $NF-{\kappa}B$ activity. Conclusions: Phytochemical study of the aerial parts of V. cinerea led to the isolation of six phenolic compounds. Compound 1 was a major metabolite, and to the best of our knowledge, compounds 2 - 6 were isolated from V.cinerea for the first time. Among the isolates, compounds 1 and 3 exhibited $TNF-{\alpha}$-induced $NF-{\kappa}B$ activity with $IC_{50}$ values of 7.5 and 11.5 M, respectively, and the inhibitory activity of phenyl propanoid compound 3 on $TNF-{\alpha}$-induced $NF-{\kappa}B$ was evaluated for the first time.

• Journal of Radiopharmaceuticals and Molecular Probes
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• v.6 no.2
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• pp.75-91
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• 2020

[^99mTc]Tc-Hexamethylpropylene amine oxime (HMPAO) is currently used as a regional cerebral blood flow imaging agent for single photon emission computed tomography (SPECT). The HMPAO ligand exists in two isomeric forms: d,l and meso showing different properties in vivo. Later studies indicated that brain uptake patterns of ^99mTc-complexes formed from separated enantiomers differed. Separation of enantiomers is difficult by fractional crystallizations method. Usually, the substance is obtained in low chemical yield in a time-consuming procedure. Furthermore, the final product still contains some impurity. So we have developed new efficient route for synthesis of R,R- and S,S-HMPAO enantiomeric compounds in 6-steps. Nucleophilic substitution (S_N2) reactions of 2,2-dimethylpropane-1,3-diamine either with S- (1a) or R-methyl2-chloropropanoate (1b) were performed to produce compounds R,R- (2a) or S,S-isomer (2b) derivatives protected with benzylchloroformate (Cbz), respectively. And then Weinreb amide and methylation reaction using Grignard reagent, oxime formation with ketone group and deprotectiion of Cbz group by hydrogenolysis gave S,S- (7a) or R,R-HMPAO (7b), respectively. Entaniomeric compounds were synthesied with high yield and purity without any undesired product. The 7a or 7b kits containing 10 ㎍ SnCl₂-2H₂O were labeled with ^99mTc with high radiolabeling yield (90%).

• Applied Biological Chemistry
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• v.39 no.2
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• pp.153-158
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• 1996

During the screening of herbicidal substances from microbial secondary metabolites using photoautotrophic cells, a strain of ME-13 with strong herbicidal activity was isolated from soil. Based on the taxonomic studies, the strain was identified as Streptomyces. Two active compounds were purified from the culture broth through the column chromatographies using active charcoal, silica gel, MCI gel, and ODS HPLC. The compounds were identified as AB3217-A and B, respectively, related to anisomycin by spectroscopic methods. AB3217-A and B completely suppressed the germination of radish and barnyard grass at 25 ppm. In comparison to anisomycin, they showed the 6 times higher inhibitory activities against the growth of shoot and root of radish and barnyard grass with EC5O of around 6 ppm.

• Bulletin of the Korean Chemical Society
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• v.34 no.5
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• pp.1349-1354
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• 2013

Twenty two new 5-fluorouracil (5-FU) derivatives, 2-butoxy-4-substituted 5-fluoropyrimidines, were synthesized and characterized by IR, $^1H$ NMR, MS, HRMS. All compounds were preliminarily evaluated by MTT assay on human liver BEL-7402 cancer cell line in vitro. Ten compounds were selected to test their cytotoxic activity against A549, HL-60 and MCF-7 cancer cell lines in vitro. These compounds were more sensitive to BEL-7402 than other cell lines, particularly, cytotoxic activity of compounds 6b, 6d-f, 6p, 6s-u were in sub-micromolar scale. The highest cytotoxic potency against A549, HL-60 and MCF-7 was shown by 2-butoxy-4-chloro-5-fluoropyrimidine (5) with $IC_{50}$ values of 0.10, 1.66 and $0.59{\mu}M$, respectively. Compounds 6d and 6e were effective against MCF-7 with $IC_{50}$ $9.73{\mu}M$ and HL-60 with $IC_{50}$ $8.83{\mu}M$, respectively.

• Bulletin of the Korean Chemical Society
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• v.34 no.5
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• pp.1407-1413
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• 2013

A new compound, perforaphenonoside A (1), along with 11 known compounds (2-12) were isolated from a methanol extract of adventitious roots of Hypericum perforatum. Their chemical structures were elucidated using chemical and physical methods as well as comparison of NMR and mass spectral data with previously reported data. Their inhibition of NF-${\kappa}B$ and activation of PPAR was measured in HepG2 cells using a luciferase reporter system. Among the compounds 3, 6, 7 and 12 inhibited NF-${\kappa}B$ activation stimulated by TNF${\alpha}$ in a dose-dependent manner, with $IC_{50}$ values ranging from 0.85 to $8.10{\mu}M$. Moreover, compounds 1-3, 7, 11 and 12 activated the transcriptional activity of PPARs in a dose-dependent manner, with $EC_{50}$ values ranging from 7.3 to $58.7{\mu}M$. The transactivational effects of compounds 1-3, 7, 11 and 12 were evaluated on three individual PPAR subtypes. Among them, compound 2 activated $PPAR{\alpha}$ transcriptional activity, with 153.97% stimulation at $10{\mu}M$, while compounds 1, 2 and 11 exhibited transcriptional activity of $PPAR{\gamma}$, with stimulation from 124.76% to 126.91% at $10{\mu}M$.

• Bulletin of the Korean Chemical Society
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• v.23 no.9
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• pp.1213-1221
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• 2002

Friedel-Crafts alkylation reaction of an isomeric mixture of 1,2,3,4,5,6,7,8- (2) and 1,2,3,4,5,6,7,8-octahydrophenanthrene (2') with excess vinylchlorosilanes such as vinyl(methyl)dichlorosilane (1a) and vinyltrichlorosilane (1b) in the presence of aluminum chloride catalyst at 80 $^{\circ}C$ gives only one dialkylated products, 9,10-bis[2-(chlorosilyl)ethyl]-1,2,3,4,5,6,7,8-octahydroanthrenes [(Cl2XSiCH2CH2)2C14H16: X = Me (4a), Cl (4b)] in good yields, but 9,10-bis[2-(chlorosilyl)ethyl]-1,2,3,4,5,6,7,8-octahydrophenanthrenes are not obtained. However, monoalkylation of 2 with 1 affords a mixture of both isomeric compounds, 9-[2-(chlorosilyl)ethyl]-1,2,3,4,5,6,7,8-octahydroanthracenes 3 and -phenanthrenes 3'. The yield of product 3' is always higher than that of 3. When a mixture of 3 and 3' is alkylated again with 1, only product 4 without phenanthrene type compounds is obtained, indicating that the isomerizations between 2 and 2', or 3 and 3'occur under the alkylation condition. The alkylation with dimethylvinylchlorosilane or trimethylvinylsilane did not proceed. The structure of 4a is determined by X-ray single crystal diffraction analysis.

• Journal of the Korean Society of Industry Convergence
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• v.6 no.3
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• pp.165-169
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• 2003

To extract alkali metal ions and heavy metal ions, search for crown ether model compounds (4a-b, 5a-b, 6a-b) bearing side arm has led to achieve in 5~6 steps starting from 2,6-dimethylaniline. The determination of structure in their compound derivatives were on the basis of melting point and nuclear magnetic resonance spectroscopy. In the solvent extraction of metal ions from the synthesized derivatives, we observed that silver ion has only high selectivity for synergistic ligation of crown ether.

• Microbiology and Biotechnology Letters
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• v.40 no.1
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• pp.57-65
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• 2012

Antifungal compounds from Bacillus polyfermenticus CJ6 were purified using SPE, preparative HPLC, and reverse phase-HPLC. Antifungal compounds from B. polyfermenticus CJ6 were separated into three fractions (8, B, C) using preparative HPLC. LC/MS analysis of antifungal peaks suggested that B. polyfermenticus CJ6 produces lipopeptides; two kinds of iturin A ($C_{14}$, $C_{15}$), three kinds of surfactins ($C_{13}$, $C_{14}$, $C_{15}$), four kinds of fengycin A ($C_{14}$, $C_{15}$, $C_{16}$, $C_{17}$) and two kinds fengycin B ($C_{16}$, $C_{17}$). The antifungal activity of fraction 8, which was presumed as inturin A, was found to be stable after the pH, heat or proteolytic enzyme treatment, but it was unstable at 50-$70^{\circ}C$ for 24 hr. The antifungal activity of fraction B, which presumed as surfactins and fengycin A, was found to be stable after the heat treatment, but it was unstable in the pH 3.0 and after the protease (type I) or ${\alpha}$-chymotrypsin treatment. The antifungal activity of fraction C, which was presumed as fengycin A and B, was found to be stable in the pH 3.0-9.0 range and the heat treatment, but it was unstable with the treatment of protease (type I). The amino acid composition of the purified peaks 8-1 and 8-2 were Asx, Tyr, Gln, Pro, and Ser in a molar ratio of 3:1:1:1:1, which showed the same amino acid composition as iturin. From these results, we confirmed that antifungal compounds from B. polyfermenticus CJ6 most likely belonged to iturin A as well as surfactins and fengycins. As lipopeptides are known to act in a synergistic manner, the antifungal compounds from B. polyfermenticus CJ6 might have potential uses in biotechnology and biopharmaceutical applications.

• Korean Journal of Pharmacognosy
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• v.48 no.4
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• pp.320-328
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• 2017

Yongdamsagan-tang has been used to treat the urinary disorders, acute- and chronic-urethritis, and cystitis in Korea. In this study, an ultra-performance liquid chromatography-electrospray ionization-mass spectrometry (UPLC-ESI-MS/MS) method was established for simultaneous analysis of the 20 bioactive marker compounds, geniposidic acid, chlorogenic acid, geniposide, liquiritin apioside, acteoside, calceolarioside B, liquiritin, nodakenin, baicalin, liquiritigenin, wogonoside, baicalein, glycyrrhizin, wogonin, glycyrrhizin, wogonin, saikosaponin A, decursin, decursinol angelate, alisol B, alisol B acetate, and pachymic acid in traditional herbal formula, Yongdamsagan-tang. Chromatographic separations of all marker compounds were conducted using a Waters Acquity UPLC BEH $C_{18}$ analytical column ($2.1{\times}100mm$, $1.7{\mu}m$) at $45^{\circ}C$ using a mobile phase of 0.1% (v/v) formic acid in water and acetonitrile with gradient elution. The MS analysis was performed using a Waters ACQUITY TQD LC-MS/MS coupled with an electrospray ionization source in the positive and negative modes. The flow rate was 0.3 mL/min and injection volume was $2.0{\mu}L$. The correlation coefficient of 20 marker compounds in the test ranges was 0.9943-1.0000. The limits of detection and quantification values of the all marker components were 0.11-6.66 and 0.34-19.99 ng/mL, respectively. As a result of the analysis using the optimized LC-ESI-MS/MS method, three compounds, geniposidic acid (from Plantaginis Semen), alisol B (from Alismatis Rhizoma), and pachymic acid (from Poria Sclerotium), were not detected in this sample. While the amounts of the 17 compounds except for the geniposidic acid, alisol B, and pachymic acid were $0.04-548.13{\mu}g/g$ in Yongdamsagan-tang sample. Among these compounds, baicalin, bioactive marker compound of Scutellariae Radix, was detected at the highest amount as a $548.13{\mu}g/g$.

• Proceedings of the Korean Institute of Electrical and Electronic Material Engineers Conference
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• 2002.08a
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• pp.25-30
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• 2002

The ternary semiconducting compounds of the $A_{4}BX_{6}$(A=Cd, Zn, Hg; B=Si, Sn, Ge; X=S, Se, Te) type exhibit strong fluorescence and high photosensitivity in the visible and near infrared ranges, so these are supposed to be materials applicable to photoelectrical devices. These materials were synthesized and single crystals were first grown by Nitsche, who identified the crystal structure of the single crystals. In this paper. author describe the undoped and $Co^{2+}$-doped $Zn_{4}SnSe_{6}$ single crystals were grown by the chemical transport reaction(CTR) method using iodine of $6mg/cm^{3}$ as a transport agent. For the crystal. growth, the temperature gradient of the CTR furnace was kep at $700^{\circ}C$ for the source aone and at $820^{\circ}C$ for the growth zone for 7-days. It was found from the analysis of x-ray diffraction that undoped and $Co^{2+}$-doped $Zn_{4}SnSe_{6}$ compounds have a monoclinic structure. The optical absorption spectra obtained near the fundamental absorption edge showed that these compounds have a direct energy gaps. These temperature dependence of the optical energy gap were closely investigated over the temperature range 10[K]~300[K]