• Journal of the Society of Cosmetic Scientists of Korea
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• v.43 no.4
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• pp.289-295
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• 2017

A. koreanum was investigated to identify the constituents possessing whitening effects. As anti-melanogenesis activities were screened for the ethanol extract and solvent fractions, n-hexane (Hex) and ethyl acetate (EtOAc) fractions showed the most potent activities. Three constituents were isolated from the n-Hex fraction of A. koreanum; kaurenoic acid (1), $16{\alpha}$-hydro-17-isovaleroyloxy-ent-kauran-19-oicacid (2), $16{\alpha}$-hydroxy-17-isovaleroyl-oxy-ent-kauran-19-oic acid (3). The chemical structures of the isolated compounds were elucidated based on the spectroscopic data including $^1H$ and $^{13}C$ NMR spectra, as well as comparison of the data to the literature values. Whitening effects were studied for the isolated compounds. Upon the anti-melanogenesis test using ${\alpha}-MSH$ stimulated B16F10 melanoma cells, the compounds 1, 2 and 3 inhibited the cellular melanogenesis and intracellular tyrosinase activities effectively. Based on these results, A. koreanum stems extract could be potentially applicable as whitening ingredients in cosmetic formulations.

• Journal of Microbiology and Biotechnology
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• v.22 no.12
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• pp.1665-1672
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• 2012

An 80% ethanol extract of Hizikia fusiforme was obtained and followed by successive fractionation using the organic solvents n-hexane, ethyl acetate, and n-butanol to identify the antioxidative substance. The aqueous part of the nbutanol fractionation step, showing high antioxidative activity, was subjected to reverse-phase liquid chromatography. As a result, a substance purified from a BB-2 fraction showed high antioxidative activity. The m/z 419 [M+H] molecular ion peak in the fraction was observed by the analysis of the ESI-LC/MS spectrum. By the analysis of 1H NMR (500 MHz, DMSO-$d_6$) and $^{13}C$ NMR (125 MHz, DMSO-$d_6$) spectra, a unique compound of the fraction was biochemically identified as a 5-hydroxy-3,6,7,8,3',4'-hexamethoxyflavone (5HHMF). We also investigated the effect of 5HHMF on human gastric AGS carcinoma cells. Western blot analysis suggested that the flavone substantially increased the levels of the death receptor-associated apoptosis mediators Fas, Fas L, FADD, TRADD, and DR4 in a concentration-dependent manner. The levels of Fas, Fas L, TRADD, and DR4 in the cells treated with 5HHMF ($5{\mu}g/ml$) were approximately 26.4-, 12.8-, 6.7-, and 9.8-times higher than those of non-treated cells, respectively. Of note, the level of FADD protein in the cells exposed to 5HHMF ($1{\mu}g/ml$) increased approximately 9.6-times. In addition, the cleavage of caspase-3, -8, and -9 in cultured AGS cells treated with 5HHMF was significantly confirmed. Therefore, our results suggest that 5HHMF from H. fusiforme is involved in the induction of death receptor-associated apoptosis mediators in human gastric AGS carcinoma cells.

• Journal of the Korean Chemical Society
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• v.36 no.2
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• pp.318-323
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• 1992

Following seven new nucleophilic adducts of sulfilimine compounds were prepared by the addition of 1-methyl-5-mercapto-1,2,3,4-tetrazole to vinylsulfilimine derivatives; S-Phenyl-S-2-(1-methyl-1,2,3,4-tetrazole-5-thio)-ethyl-N-p-tosylsulfilimine, S-p-tolyl-S-2-(1-methyl-1,2,3,4-tetrazole-5-thio)-ethyl-N-p-tosylsulfilimine, S-m-tolyl-S-2-(1-methyl-1,2,3,4-tetrazole-5-thio)-ethyl-N-p-tosylsulfilimine, S-p-chlorophenyl-S-2-(1-methyl-1,2,3,4-tetrazole-5-thio)-ethyl-N-p-tosylsulfilimine, S-p-bromophenyl-S-2-(1-methyl-1,2,3,4-tetrazole-5-thio)-ethyl-N-p-tosylsulfilimine, S-p-methoxyphenyl-S-2-(1-methyl-1,2,3,4-tetrazole-5-thio)-ethyl-N-p-tosylsulfilimine and S-p-nitrophenyl-S-2-(1-methyl-1,2,3,4-tetrazole-5-thio)-ethyl-N-p-tosylsulfilimine. The structures of these adducts were confirmed by elemental analyses, MP, UV, IR-and NMR-Spectra.

• Journal of the Korean Chemical Society
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• v.36 no.5
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• pp.661-668
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• 1992

The polymeric compound [{Mo(NO)_2Cl_2}n] was prepared by reductive nitrosylation of NaNO_2 and acidified FeSO_4 with MoCl_5. The reactions of [{Mo(NO)_2Cl_2}n] with unidentate and bidentate ligands afforded neutral monomeric $[Mo(NO)_2Cl_2L_2(or L-L)] in high yield (80∼90%). 3,5-Lutidine, {\gamma}-Cyanopyridine, 1,2-Phenylenediamine, 1,10-Phenanthroline, sym-Diphenylethylenediamine, 9,10-Phenanthrenequinone, 1,3-Bis(diphenylphosphino)propane and 8-Hydroxyquinoline were used as coordinating ligands. The preparation and characterization of these dinitrosylmolybdenum complexes by elemental analysis, 1H NMR, infrared, and UV-Visible spectroscopy are reported. The infrared spectra indicate that in all of the compounds prepared, the NO groups occupy cis-positions in the octahedral group of ligands.

• Journal of Life Science
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• v.14 no.1
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• pp.91-97
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• 2004

As a part of our study on the improvement of anticonvulsant, here we report the synthesis of N-acyl-$\alpha$-aminosuc-cinimides 1 and N-acyl-$\alpha$-aminoglutarimides 2. (R)-Benzoic acid 4-benzyloxycarbonylamino-2-oxo-pyrrolidin-1-ylester 6a, (R)-4-nifro-benzoic acid 4-benzyloxycarbonylamino-2- oxo-pyrrolidin-1-yl ester 6b, (R) -4-nitro-benzoic acid 4-benzyloxycarbonylamino-2-oxo-pyrrolidin-1-yl ester 6c, and (R)-propionic acid 4-benzyloxycarbonylamino-2-oxo-pyrrolidin-1-yl ester 6d were synthesized from (R)-2-benzyloxy carbonylamino-succinic acid 3 as a starting meterial. (R)-(3- Benzyloxycarbonylamino-2,6-dioxo-piperidin-1-yloxy)-acetic acid methyl ester 10a, (R)-(3-benzyloxycarbonylamino-2,6-dioxo-piperidin-1-yloxy)-acetic acid ethy1 ester 10b, an d (R)-2-(3-benzyloxycarbonylamino-2,6- diox o-piperidin-1-yl oxy)-propionic acid methyl ester l0c were synthesized from (R)- 3-carbobenzyloxy-amino-glutarmic acid 7 as a starting meterial. The yield, mp, IR, $^1H-NMR,\; and^{13}C$- NMR spectra of the products 6a, 6b, 6c, 6d, 10a, l0b, l0c are summarized in footnote. The biological studies of these compounds are in progress and will be reported in future.

• Journal of Microbiology and Biotechnology
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• v.10 no.1
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• pp.27-34
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• 2000

The chloroform and methanol (2;1, v/v) extract from an edible plant, Actinidia arguta Planchon, appeared to possess antitumor activity against human leukemias Jurkat T and U937 cells through inducing apoptosis. The substance in the solvent extract was purified by silica gel column chromatography, preparative TLC, and Sephadex LH-20 column chromatography. Characteristics of the substance analyzed by UV scanning analysis, $^1H$ and $^{13}C$ NMR spectra suggested that the substance belongs to the chlorophyll derivatives-like group. The $IC_{50}$ value of the chlorophyll derivative (Cp-D) determined by MTT assay was $15\mu\textrm{g}/ml$ for Jurkat, $10\mu\textrm{g}/ml$ for U937, and $11.4\mu\textrm{g}/ml$ for HL-60m and was more toxic to these leukemias than to solid tumors or normal fibroblast. In order to elucidate cellular mechanisms underlying the cytotoxicity, the effect of the Cp-D on Jurkat T cells was investigated. When cells were treated with the Cp-D at a concentration of $15\mu\textrm{g}/ml$, [3H]thymidine incorporation declined rapidly and wa undetectable in 1h. However, no significant changes were made in the cell cycle distribution of the cells by 24h. The sub-Gl peak representing apoptotic cells began to be detectable in 36h, at which time apoptotic DNA fragmentation was also detected on agarose gel electrophoresis, demonstrating that the cytotoxic effect of the Cp-D is attributable to the induced apoptosis. Under the same conditions, although the protein level of cyclin-dependent kinases such as cdc4, csk6, cdk2, and cdc2 was not significantly changed until 24h, the kinase activity of all c안 rapidly declined and reached a minimum level within 1-6h and then recovered to the initial level by 12h and sustained until 24h. These results suggest that inactivation of cdks at an inappropriate time during the cell cycle progression in jurkat T cells following a treatment with the Cp-D leads to induction of apoptotic cell death.

• Journal of the Society of Cosmetic Scientists of Korea
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• v.43 no.1
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• pp.53-60
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• 2017

In this study, we investigated whitening and anti-inflammatory constituents from a watermelon (Citrullus lanatus, C. lanatus) vines (leaves and stems). As anti-melanogenesis and anti-inflammatory activities were screened for the ethanol extract and solvent fractions, n-hexane (n-Hex) and ethyl acetate (EtOAc) fractions showed the most potent activities. Three constituents were isolated from the n-Hex and EtOAc fractions of C. lanatus; ${\alpha}-linolenic$ acid (1), sigmast-7-en-O-${\beta}$-D-glucopyranoside (2), 1-feruloyl-${\beta}$-D-glucopyrinoside (3). The chemical structures of the isolated compounds were elucidated based on the spectroscopic data including $^1H$ and $^{13}C$ NMR spectra, as well as comparison of the data to the literature values. Whitening and anti-inflammatory effects were studied for the isolated compounds. Upon the anti-melanogenesis tests using ${\alpha}-MSH$ stimulated B16F10 melanoma cells, the compounds 1 and 3 inhibited the cellular melanogenesis and intracellular tyrosinase activities effectively. For the anti-inflammation tests using lipopolysaccharide (LPS)-induced RAW 264.7 cells, the isolates 1 and 3 were determined to decrease the production of nitric oxide (NO) and pro-inflammatory cytokines ($TNF-{\alpha}$, IL-6). Based on these results, C. lanatus vines extract could be potentially applicable as whitening and anti-inflammatory ingredients in cosmetic formulations.

• Journal of the Korean Applied Science and Technology
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• v.37 no.5
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• pp.1356-1365
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• 2020

In this study, the extracts of Hydrangea macrophylla (H. macrophylla) flowers were investigated for the anti-oxidative and anti-inflammatory activities, and their active constituents were identified. The anti-oxidative effects were tested by DPPH and ABTS⁺ assays. To evaluate anti-inflammatory activities, LPS-induced RAW264.7 cells were examined. Among the extracts, the ethyl acetate fraction showed potent radical scavenging activities and inhibition of nitric oxide (NO) production. Chromatographic purification of the extract led to isolation of the compounds; hydrangenol (1), prunin (2) and astragalin (3). The chemical structures of the constituents were elucidated based on spectroscopic data including NMR spectra, as well as comparison of the data in the literature values. Quantitative analysis by high pressure liquid chromatography (HPLC) determined hydrangenol (1) as the major constituent. Isolated compounds 1-3 decreased the NO level without causing cell toxicities. Based on these results, it was suggested that the extract from H. macrophylla flowers could be potentially applicable as an anti-oxidative and/or anti-inflammatory ingredients.

• The Korean Journal of Pesticide Science
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• v.10 no.4
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• pp.249-261
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• 2006

Fifty compounds such as ester, sulfonyl ester, carbamate, ether and phosphoyl ester derivatives of 4-isopropyl-3-methylphenol(I) and 5-isopropyl-3-methylphenol(II) were synthesized. These derivatives were identified by IR, GC/MS and $^1H$-NMR spectra. Their in vitro antifungal activities were tested against 10 plant pathogenic fungi. Among them, several compounds showed potent in vitro antifungal activity. The selected compounds showing potent in vitro antifungal activity were tested for their in vivo antifungal activities against 5 plant diseases such as rice blast, rice sheath blast, cucumber anthracnose, cucumber gray mold and tomato late blight. As a result, 4-isopropyl-3-methylphenyl(2-amino-thiazole-4-yl)methoxyiminoacetate(I-7a) showed a potent in vivo antifungal activity against rice blast. Both methyl (4-isopropyl-3-methylphenoxy)acetate(I-4d) and methyl (5-isopropyl-3-methylphenoxy)acetate(II-4d) effectively inhibited the development of cucumber gray mold.

• Journal of Industrial and Engineering Chemistry
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• v.67
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• pp.148-155
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• 2018

To get a better understanding of the effect of physicochemical properties and microstructure on $SO_2$ absorption behavior of DESs with different molar ratios of EmimCl and EG (from 2:1 to 1:2), densities (${\rho}$), viscosities (${\eta}$), speeds of sound (u), refractive indices ($n_D$), and thermal decomposition temperatures ($T_d$) of EmimCl-EG DESs were measured and used to obtain the other derived properties, such as thermal expansion coefficient (${\alpha}_p$) and activation energy for viscous flow ($E_{\eta}$). Moreover, FT-IR spectra and in situ variable-temperature NMR spectroscopy were employed to study the microstructures of DESs. Based on physicochemical and spectroscopic properties, the influence of the concentrations of EmimCl on the interactions in DESs was explored to be associated with their $SO_2$ absorption behavior. The results show that the interactions between $Emim^+$ and $Cl^-$ of EmimCl is gradually weakening with increasing the concentration of EG in DESs by forming of hydrogen bond interaction of $O-H{\cdots}Cl^-$, resulting in a decrease of ${\rho}$, ${\eta}$, u, $n_D$, and $T_d$ of DESs, and hindering the charge-transfer interaction of $SO_2$ with $Cl^-$ and deceasing $SO_2$ capture capacity. Moreover, the $SO_2$ absorption capacity of DESs is proportional to their ${\rho}$ and $E_{\eta}$, respectively.