• Title/Summary/Keyword: Nitro compounds

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Nitration of 3,7,9,11-Tetraoxo-2,4,6,8,10-pentaaza[3.3.3]propellane (3,7,9,11-테트라옥소-2,4,6,8,10-펜타아자[3.3.3]프로펠레인의 니트로화 반응)

  • Shin, Moonyong;Ha, Tae-Hwan;Chung, Kyoo-Hyun;Kim, Jin Seuk;Kim, Young Gyu
    • Applied Chemistry for Engineering
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    • v.25 no.2
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    • pp.188-192
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    • 2014
  • Until now, there has been much efforts for the development of polycyclic molecules as high energy materials because of their high density and potential energy. However, there were only a few reports on the development of highly N-substituted polycyclic compounds due to difficulties of the synthesis. We have designed pentaazapropellanes as new high energy materials and we have recently reported unsubstituted 3,7,9,11-tetraoxo-2,4,6,8,10-pentaaza[3.3.3]propellane (TOPAP) 2 as a new skeleton for high energy materials. Herein, the nitration of TOPAP 2 was reported for the first time. Thus, 2,6-dinitro-3,7,9,11-ttraoxo-2,4,6,8,10-pentaaza[3.3.3]propellane (2,6-DNTOPAP) 5C, which is a new nitro derivative of TOPAP 2, was obtained up to 82% yield by the reaction of $NO_2BF_4$ and anhydrous $HNO_3$. The structure of 5C was determined by spectroscopic analysis.

Inhibitory Effect of Methanol Extracts and Solvent Fractions from Doenjang on Mutagenicity Using in vitro SOS Chromotest and in vivo Drosophila Mutagenic System (된장 메탄올 추출물 및 분획물에 의한 in vitro SOS Chromotest 실험계와 in vivo 초파리 돌연변이 검출계에서의 항돌연변이 효과)

  • Lim, Sun-Young;Lee, Sook-Hee;Park, Keun-Young;Yun, Hee-Sun;Lee, Won-Ho
    • Journal of the Korean Society of Food Science and Nutrition
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    • v.33 no.9
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    • pp.1432-1438
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    • 2004
  • This study investigated the inhibitory effect of methanol extracts and several solvent fractions from doen-jang on mutagenicity using in vitro SOS chromotest and in vivo Drosophila mutagenic system. In order to determine an antimutagenic effect of doenjang methanol extracts, other soybean fermented foods and original materials were compared. The treatment of doenjang methanol extracts (100 ${\mu}$/assay) to SOS chromotest system inhibited N-methyl-N'-nitro-N-nitrosoguanidine (MNNG) induced mutagenicity by 87~97% and showed higher antimutagenic effect than other fermented foods. Among solvent fractions from doenjang methanol extracts, the ethylacetate and dichloromethane fractions showed the stronger antimutagenic effect (91% and 95%, respectively) in SOS chromotest. In Drosophila mutagenic system, the treatment of ethylacetate fraction (5%/bottle) significantly inhibited aflatoxin $B_1$ induced mutagenicity by 97%. These results demonstrated that doenjang had an inhibitory effect to mutagenic agents in both in vitro and in vivo mutagenic systems, suggesting that its antimutagenic effect may be due to active compounds in the ethylacetate fraction from doenjang methanol extracts.

Screening for Antimutagenic Effects of the Wild Mushrooms in Korea (한국산 야생버섯류중 항변이원성 효과의 검색)

  • Kim, Hyun-Jeong;Lee, Byeung-Hun;Kim, Ok-Mi;Lee, Kap-Duk;Lee, Kap-Rang
    • Korean Journal of Food Science and Technology
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    • v.30 no.3
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    • pp.688-692
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    • 1998
  • To detect naturally occuring antimutagenic substances from wild mushrooms in Korea, the screening for the antimutagenic compounds containing in ethanol and water extracts of 13 wild mushrooms toward benzo(a) pyrene (B(a)P) and $N-methyl-N'-nitro-N-nitrosoguanidine\;(MNNG)$ using the Ames assay system with Salmonella typhimurium TA98 and TA100 were studied. The ethanol extracts of Polyporus dispansus, Cantharellus infundibuliformis, Agaricus subrutilescens, Daedalea dickinsii, Panaeolus papilionaceus and Hydnum repandum showed significantly antimutagenic activity toward B(a)P. The water extracts of Hydnum repandum showed the strong antimutagenic activity toward B(a)P in S. typhimurium TA100, however the water extracts of the mushrooms did not show antimutagenic activity. Whereas 5 out of 13 samples exhibited antimutagenicity toward a direct mutagen of MNNG. The water extracts from mushrooms also not showed antimutagenic activity. The antimutagenic effect increased with increasing concentraion of the ethanol extracts from Polyporus dispansus.

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Bee Venom Enhanced Cytotoxic Effect of Natural Killer Cells on Human Lung Cancer Through Inducing Extrinsic Apoptosis

  • Kim, Jung Hyun;Song, Ho Sueb
    • Journal of Acupuncture Research
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    • v.31 no.1
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    • pp.111-119
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    • 2014
  • Objectives : I investigated whether Bee Venom can synergistically strengthen the cytotoxic effects of NK-92 cells, enhancing the inhibition of the growth of Lung Cancer Cells including A549 and NCI-H460 through induction of death receptor dependent extrinsic apoptosis and NO generation in the Nitro-oxide pathway. Methods : Bee Venom inhibited cell proliferation of A549 or NCI-H460 Human Lung Cancer Cells as well as NK-92 Cells. Moreover, when they were co-punctured with NK cells and concomitantly treated by 3 ${\mu}g/ml$ of Bee Venom, more influence was exerted on inhibition of proliferation of A549 or NCI-H460 Human Lung Cancer Cells than BV or NK cell co-culture alone. Results : The expression of Fas, TNFR2, DR3, DR6 in A549 Lung Cancer Cells was significantly increased by co-culture of NK-92 cells and treatment of 3 ${\mu}g/ml$ of Bee Venom, compared to co-culture of NK-92 cells alone, whereas the expression of Fas, TNFR2, DR6 in NCI-H460 Lung Cancer Cells was significantly increased by co-culture of NK-92 cells, representing no synergistic effects in the co-culture of NK-92 cell and concomitant treatment of 3 ${\mu}g/ml$ of Bee Venom. Coincidently, caspase-8, a expression of pro-apoptotic proteins in the extrinsic apoptosis pathway demonstrated same results as the above. Meanwhile, In NO generation, there is little change of NO generation in co-culture of NK-92 cells with A549 cells as well as the co-culture of NK-92 cell with them and concomitant treatment of 3 ${\mu}g/ml$ of Bee Venom, whereas increase of NO generation was shown in co-culture of NK-92 cells with NCI-H460 cells as well as the co-culture of NK-92 cell with them and concomitant treatment of 3 ${\mu}g/ml$ of Bee Venom, although synergistic effects by Bee Venom was not found. Conclusions : These present data provide that Bee Venom could be useful candidate compounds to enhance lung cancer growth inhibiting ability of NK-92 cells through DR expression and the related apoptosis.

Antimutagenicity and Anticancer Activity of Soybean Fractions Extracted by Solvents (대두 분획물의 항돌연변이 및 항암활성 효과)

  • Lim, Sun-Young
    • Journal of Life Science
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    • v.17 no.10
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    • pp.1368-1373
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    • 2007
  • Inhibitory effects of several solvent fractions from soybean on mutagenicity using Salmonella typhimurium TA 100 in Ames test and growth of human cancer cells (AGS gastric adenocarcinoma, Hep 3B hepatocellular cancinoma and HT-29 colon cancer cells) were studied. The treatment of dichloromethane and ethylacetate fractions (2.5 mg/assay) extracted from soybean to Ames test system inhibited aflatoxin $B_1\;(AFB_1)$ induced mutagenicity by 83%, respectively, and showed a higher antimutagenic effect than other solvent fractions. In case of N-methyl-N#-nitro-N-nitrosoguamidine (MNNG) induced mutagenicity, the ethylacetate fraction showed the highest inhibitory effect (by 67%) among solvent extracts, although the inhibitory effect was not stronger compared with $AFB_1$ induced mutagenicity. In sulforhodamine B (SRB) assay, the treatment of ethylacetate fraction (2 mg/assay) significantly inhibited the growth of AGS, Hep 3B and HT-29 cancer cells by 66%, 73% and 77%, respectively, followed with the intermediate and dichloromethane fractions. These results indicated that soybean fraction extracted with ethylacetate had higher inhibitory effects on $AFB_1$ and MNNG in Ames test and growth inhibition activity to human cancer cells was appeared, suggesting that soybean fraction extracted with ethylacetate may contain the biologically active compounds.

Thermotropic Liquid Crystalline Properties of α,ω-Bis(4-cyanoazobenzene-4'-oxy)alkanes (α,ω-비스(4-사이아노아조벤젠-4'-옥시)알케인들의 열방성 액정 특성)

  • Jeong, Seung Yong;Kim, Hyo Gap;Ma, Yung Dae
    • Applied Chemistry for Engineering
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    • v.22 no.4
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    • pp.358-366
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    • 2011
  • A homologous series of linear liquid crystal dimers, the ${\alpha},{\omega}$-bis(4-cyano-azobenzene-4'-oxy)alkanes (CATWETn, where n, the number of methylene units in the spacer, is 2~10) were synthesized, and their thermotropic liquid crystalline phase behavior were investigated. The CATWETn with n of 3 and 6 exhibited monotropic nematic phases, whereas other derivatives showed enantiotropic nematic phases. The nematic-isotropic transition temperatures of the dimers and their entropy variation at the phase transition showed a large odd-even effect as a function of n. This phase transition behavior was rationalized in terms of the change in the average shape of the spacer on varying the parity of the spacer. The thermal stability and degree of order in the nematic phase and the magnitude of the odd-even effect of CATWETn were similar to those for the methoxy-, nitro-, and pentyl-substituted dimers, while they were significantly different from those for the monomesogenic compounds, 1-{4-(4'-cyanophenylazo)phenoxy}alkylbromides and the side-chain liquid-crystalline polymers, the poly[1-{4-(4'-cyanophenylazo)phenoxyalkyloxy}ethylene]s. The results were discussed in terms of 'virtual trimer model' by Imrie.

Validation of a Rapid Quantitative Method for the Residues of Nitrofuran Metabolites in Loach by Accelerated Solvent Extraction and HPLC Triple Quadrupole Mass Spectrometry

  • Ryu, Eun Chae;Han, Yun-jeong;Park, Seong-soo;Lim, Chul-joo;Choi, Sunok;Park, Se Chang
    • Journal of Food Hygiene and Safety
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    • v.31 no.2
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    • pp.85-93
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    • 2016
  • A rapid method using HPLC-MS/MS has been developed for quantitative determination of the metabolites of nitrofurans, namely 3-amino-2-oxazolidone (AOZ), 5-morpholinomethyl-3-amino-2-oxazolidinone (AMOZ), 1-ammino-hydantoin (AHD) and semicarbazide (SEM) in loach. The extraction procedure was founded on simultaneous acidic hydrolysis and derivatization using 2-nitrobenzaldehyde (2-NBA) for 1 hour at $50^{\circ}C$, followed by purification with liquid-liquid extraction. Recovery was evaluated by spiking standards into blank samples at three levels (0.5, 1.0 and $2.0{\mu}g/kg$), and the mean recovery was 75.1-108.1%. Precision values expressed as the relative standard deviation (%RSD) were ${\leq}8.7%$ and ${\leq}8.5%$ for intra-day and inter-day precision, respectively. Linearity was studied in the range of $0.2-20{\mu}g/Kg$ for NBAOZ, $0.8-20{\mu}g/Kg$ for NBAMOZ, $0.2-20{\mu}g/Kg$ for NBAHD, and $0.1-20{\mu}g/Kg$ for NBSEM, and the obtained coefficient correlations (r) were ${\geq}0.99$ for all compounds. Limits of detection (LODs) for the derivatized nitrofuran metabolites were established at $0.06{\mu}g/Kg$ for NBAOZ, $0.24{\mu}g/Kg$ for NBAMOZ, $0.06{\mu}g/Kg$ for NBAHD, and $0.03{\mu}g/Kg$ for NBSEM. Limits of quantification (LOQs) were established at $0.2{\mu}g/Kg$ for NBAOZ, $0.8{\mu}g/Kg$ for NBAMOZ, $0.2{\mu}g/Kg$ for NBAHD, and $0.1{\mu}g/Kg$ for NBSEM. This simplified rapid method for reducing the derivatization and hydrolysis times can be applied to the determination of nitro-furan residues in loach.

Inhibitory Effect of Linum usitatissimum and Perilla frutescens as Sources of Omega-3 Fatty Acids on Mutagenicity and Growth of Human Cancer Cell Lines (식물성 오메가-3계 지방산 급원인 아마씨 및 들깨의 항돌연변이 및 암세포 증식 억제 효과)

  • Lim, Sun-Young
    • Journal of Life Science
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    • v.19 no.12
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    • pp.1737-1742
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    • 2009
  • It has been known that Linum usitatissimum and Perilla frutescens are dietary sources of possible chemopreventive compounds such as lignans and $\alpha$-linolenic acid. Here, we investigated and compared the inhibitory effects of methanol extracts from Linum usitatissimum and Perilla frutescens on mutagenicity using the Ames test, and growth of human cancer cells (AGS human gastric adenocarcinoma, HT-29 human colon cancer, Hep 3B hepatocellular carcinoma cells). In the Ames test system using Salmonella typhimurium TA100, aflatoxin $B_1$ ($AFB_1$)-induced mutagenicity was significantly inhibited by treatment with the methanol extract from either Linum usitatissimum or Perilla frutescens (p<0.05) in a dose dependent manner. As for N-methyl-N'-nitro-N-nitrosoguamidine (MNNG)-induced mutagenicity, the methanol extracts (5 mg/assay) from Linum usitatissimum and Perilla frutescens showed 63% and 78% inhibitory rates, respectively, indicating that Perilla frutescens possessed stronger antimutagenic activity than did Linum usitatissimum. Inhibitory effects of methanol extracts from Linum usitatissimum and Perilla frutescens on the growth of human cancer cells (AGS, HT-29 and Hep 3B) appeared to increase dose dependently, and the inhibition was more effective against AGS and HT-29 compared to Hep 3B cells. Our results suggested that the methanol extract from Perilla frutescens showed stronger antimutagenic activity than that from Linum usitatissimumas assayed by the Ames mutagenic test, whereas the methanol extract from Linum usitatissimum was more effective than its counterpart for growth inhibition of human cancer cells. It is concluded that intake of Linum usitatissimum and Perilla frutescens as sources of omega-3 fatty acids will be beneficial for preventing cancer.

Decomposition of a Substituted Diphenyl Ether Herbicide(MC-4379) by Some Environmental Factors (환경요인(環境要因)에 의(依)한 치환(置換) Diphenyl Ether계(系) 제초제(除草劑) MC-4379의 분해(分解)에 관(關)한 연구(硏究))

  • Lee, Jae-Koo;Kim, Hae-Yong
    • Applied Biological Chemistry
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    • v.18 no.1
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    • pp.30-41
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    • 1975
  • A substituted diphenyl ether herbicide(MC-4379) was studied on the decomposition by some environmental factors; sunlight, microorganisms, and the crude enzyme in rice plant extract. All the decomposition products were confirmed by means of TLC, GLC, and IR. The parent compound and the decomposition products were put to the test for the effect on the growth of some plants. The results obtained are summarized as follows: 1. Photolysis Amino-MC-4379, 2,4-dichloro-3'-carboxyl-4'-nitrodiphenyl ether, Nitrofen, 2,4-dichloro-3'-carboxyl-4'-amino-diphenyl ether, amino-Nitrofen, 3-carboxymethyl-4-nitrophenol, p-nitrophenol, p-aminophenol, etc. were confirmed as photoproducts, in addition to a relatively small amount of an unknown compound. It was confirmed that the solution-phase photolysis of MC-4379 was accelerated much more by the aid of a photosensitizer benzophenone. 2. Degradation by the crude extract of germinating rice seeds Nitrofen was confirmed as a major degradation product, in addition to a relatively small amount of and unknown compound. Most of the parent compound remained unchanged. 3. Degradation by microorganisms Nitrofen and amino-MC-4379 were confirmed as the major products. in addition to a small amount of an unknown compound. 4. The germinating rice seeds and soybean were grown in the 1,000 ppm emulsions of some chemicals, respectively. The effect on rice plant growth was in the inhibitory order of p-nitrophenol > C-6989> Nitrofen > amino-Nitrofen > MC-4379. The effect on soybean was in the order of Nitrofen > amino-Nitrofen > MC-4379. Two weeds, Amantus blitum and Setaria viridis were grown in the 500 ppm emulsions containing the compounds, respectively. After incubation for 3 days, it was observed that all the shoots had been dead.

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