• Title/Summary/Keyword: carboxylic acids

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A Sphingolipid and Tyrosinase Inhibitors from the Fruiting Body of Phellinus linteus

  • Kang, Hye-Sook;Park, Jin-Ho;Cho, Won-Ki;Park, Jong-Cheal;Choi, Jae-Sue
    • Archives of Pharmacal Research
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    • v.27 no.7
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    • pp.742-750
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    • 2004
  • This paper for the first time reports the isolation of 5 compounds from Phellinus linteus. A sphingolipid (1) and two tyrosinase inhibitory compounds (2, 3) along with two carboxylic acids (4, 5), were isolated from the fruiting body of Phellinus linteus (Berk & Curt) Aoshima. The structure of compound 1 was identified as 1-O-$\beta$-D-glucopyranosyl-(2S, 3R, 4E, 8E)-2-[(2R)-2-hydroxyhexadecanoylamino]-9-methyl-4,8-octadecadiene-1,3-diol, known as cerebroside B, based on spectroscopic methods such as 1D and 2D NMR as well as by acid hydrolysis. Compounds 2-5 were identified as protocatechualdehyde (2), 5-hydroxymethyl-2-furaldehyde (HMF) (3), succinic acid (4), and fumaric acid (5) based on the spectroscopic evidence. Compounds 2 and 3 inhibited the oxidation of L-tyrosine catalyzed by mushroom tyrosinase with an $IC_{50}$ of 0.40 and 90.8 $\mu\textrm{g}$/mL, respectively. The inhibitory kinetics, which were analyzed by the Lineweaver-Burk plots, were found to be competitive and noncompetitive inhibitors with a $K_{j}$ of 1.1 $\mu\textrm{m}$ and 1.4 mM, respectively.

Synthesis and Biological Activity of 3 - (Substituted) Tetrazolylmethyl Cephalosporins (3- (치환) 테트라조일메칠세파로스포린의 합성과 생리활성)

  • Ko, Ok-Hyun;Kim, Young-Soo;Ko, Bong-Suk;Lee, Jae-Young;Ha, Jai-Chun;Bang, Hee-Jae;Yoo, Jin-Cheol;Kang, Hyung-Ryong
    • YAKHAK HOEJI
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    • v.42 no.1
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    • pp.12-24
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    • 1998
  • For the development of new cephalosporin antibiotics with aminothiazolcarboxymethylethoxyimino moiety on the C-7 position and tetrazolymethyl moiety on the C-3 position of cephe m ring, 7${\beta}$-[(Z)-2-(2-aminothiazol-4-yl)-2-(1-carboxy-1-methylethoxyimino)acetamido]-3-[5-(substituted)tetrazol-2-yl]methyl-3-cephem-4-carboxylic acids(28-35) were synthesized. These compounds were tested for antimicrobial activity in vitro against Gram(+) and Gram(-) bacteria. They showed remarkable antibacterial activity against Escherichia coli AB 1157, Escherichia coli AB 0111, Escherichia coli BE 1186, Micrococcus luteus ATCC 9341, Salmonella typhimurium TV 119, Salmonella typhimurium SL 1102, Staphylococcus aureus IFO 12732, Staphylococcus aureus R-209, but these compounds were not active against Pseudomonas aeruginosa N-10.

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Characteristics of Bacterial Communities in Biological Filters of Full-Scale Drinking Water Treatment Plants

  • Choi, Yonkyu;Cha, Yeongseop;Kim, Bogsoon
    • Journal of Microbiology and Biotechnology
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    • v.29 no.1
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    • pp.91-104
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    • 2019
  • The taxonomic and functional characteristics of bacterial communities in the pre-chlorinated rapid filters and ozonated biological activated carbon (BAC) filters were compared using Illumina MiSeq sequencing of the 16S rRNA gene and community-level physiological profiling (CLPP) based on sole-carbon-source utilization patterns. Both the rapid filters and BAC filters were dominated by Rhizobiales within ${\alpha}-proteobacteria$, but other abundant orders and genera were significantly different in both types of filter. Firmicutes were abundant only in the intermediate chlorinated rapid filter, while Acidobacteria were abundant only in the BAC filters. Bacterial communities in the rapid filter showed high utilization of carbohydrates, while those in the BAC filters showed high utilization of polymers and carboxylic acids. These different characteristics of the bacterial communities could be related to the different substrates in the influents, filling materials, and residual disinfectants. Chlorination and ozonation inactivated the existing bacteria in the influent and formed different bacterial communities, which could be resistant to the oxidants and effectively utilize different substrates produced by the oxidant, including Phreatobacter in the rapid filters and Hyphomicrobium in the BAC filters. Bradyrhizobium and Leptothrix, which could utilize compounds adsorbed on the GAC, were abundant in the BAC filters. Ozonation increased taxonomic diversity but decreased functional diversity of the bacterial communities in the BAC filters. This study provides some new insights into the effects of oxidation processes and filling materials on the bacterial community structure in the biological filters of drinking water treatment plants.

Induction of Growth Inhibition by BCH in KB Human Oral Epidermoid Carcinoma Cells (구강 편평세포암종 KB세포에서 아미노산 수송억제제 BCH에 의한 세포성장 억제)

  • Yoon, Jung-Hoon;Kim, Youn-Bae;Kim, Do-Kyung
    • Journal of the Korean Society of Food Science and Nutrition
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    • v.32 no.5
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    • pp.758-763
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    • 2003
  • Amino acid transporters play an important role in supplying nutrients to normal and cancer cells for cell proliferation. System L is a major transport system responsible for the N $a^{+}$-independent, large neutral amino acids including several essential amino acids. L-type amino acid transporter 1 (LAT1), an isoform of system L amino acid transporter, is highly expressed presumably to support their continuous growth and proliferation in malignant tumors. 2-Aminobicyclo- (2,2,1) -heptane-2-carboxylic acid (BCH) is a model compound for study of amino acid transporter as a system L selective inhibitor. In the present study, we examined whether BCH induced growth inhibition in KB human oral squamous carcinoma cell line or not. The uptake of L-[$^{14}$ C]leucine by KB cells is inhibited by BCH in a concentration dependent manner with a Ι $C_{50}$ value of 75.3$\pm$6.2 ${\mu}{\textrm}{m}$ and a $K_{i}$ value of 98.7$\pm$ 4.1 ${\mu}{\textrm}{m}$. The growth of KB cells is inhibited by BCH in time dependent manner and concentration dependent manner with a Ι $C_{50}$ value of 11.1 $\pm$0.8 mM. In the DNA of KB cells treated with the various concentrations and various periods of BCH, the characteristic ladders associated with DNA fragmentation were not observed. These results suggest that BCH inhibits the growth of KB oral epidermoid carcinoma cells through the inhibition of transport of neutral amino acids into cells without DNA break down. This phenomenon will be a new rationale for anti-cancer therapy.y.

Mechanism of Growth Inhibition by BCH in HEp2 Human Head and Neck Squamous Cell Carcinoma (사람 두경부 편평세포암종 HEp2 세포에서 BCH에 의한 세포성장 억제기전)

  • Choi, Bong-Kyu;Jung, Kyu-Yong;Cho, Seon-Ho;Kim, Chun-Sung;Kim, Do-Kyung
    • Journal of the Korean Society of Food Science and Nutrition
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    • v.37 no.5
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    • pp.555-560
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    • 2008
  • Amino acid transporters are essential for the growth and proliferation in all living cells. Among the amino acid transporters, the system L amino acid transporters are the major nutrient transport system responsible for the $Na^+$-independent transport of neutral amino acids including several essential amino acids. The L-type amino acid transporter 1 (LAT1), an isoform of system L amino acid transporter, is highly expressed in cancer cells to support their continuous growth and proliferation. 2-Aminobicyclo-(2,2,1)-heptane-2-carboxylic acid (BCH) is a model compound for the study of amino acid transporter as a system L selective inhibitor. We have examined the effect and mechanism of BCH on cell growth suppression in HEp2 human head and neck squamous cell carcinoma. The BCH inhibited the L-leucine transport in a concentration-dependent manner with a $IC_{50}$ value of $51.2{\pm}3.8{\mu}M$ in HEp2 cells. The growth of HEp2 cells was inhibited by BCH in the timeand concentration-dependent manners. The formation of DNA ladder was not observed with BCH treatment in the cells. Furthermore, the proteolytic processing of caspase-3 and caspase-7 in the cells were not detected by BCH treatment. These results suggest that the BCH inhibits the growth of HEp2 human head and neck squamous cell carcinoma through the intracellular depletion of neutral amino acids for cell growth without apoptotic processing.

General Characteristics of Taurine: A Review (타우린의 일반적 특성에 관한 선행연구 고찰)

  • Yoon, Jin A;Choi, Kyung-Soon;Shin, Kyung-Ok
    • The Korean Journal of Food And Nutrition
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    • v.28 no.3
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    • pp.404-414
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    • 2015
  • Taurine is one of the most abundant free ${\beta}$-amino acids in the human body that accounts for 0.1% of the human body weight. It has a sulfonic acid group in place of the more common carboxylic acid group. Mollusks and meat are the major dietary source of taurine, and mother's milks also include high levels of this amino acid. The leukocytes, heart, muscle, retina, kidney, bone, and brain contain more taurine than other organs. Furthermore, taurine can be synthesized in the brain and liver from cysteine. There are no side effects of excessive taurine intake in humans; however, in case of taurine deficiency, retinal abnormalities, reduced plasma taurine concentration, and other abnormalities may occur. Taurine enters the cell via a cell membrane receptor. It is excreted in the urine (approximately 95%) and feces (approximately 5%). Taurine has a number of features and functions, including conjugation with bile acid, reduction of blood cholesterol and triglyceride levels, promotion of neuron cell differentiation and growth, antioxidant effects, maintenance of cell membrane stability, retinal development, energy generation, depressant effects, regulation of calcium level, muscle contraction and relaxation, bone formation, anti-inflammatory effects, anti-cancer and anti-atherogenic effects, and osmotic pressure control. However, the properties, functions, and effects of taurine require further studies in future.

Synthesis of Coumarin Analogues and their Antitumor Activity (쿠마린 유도체의 합성과 그들의 항암효과)

  • Lee, Jee-Hyun;Lee, Jae-Ho;Kim, Hyun-Kwan;Kim, Eui-Geom;Shen, Gui-nan;Cho, Soo-Hyun;Myung, Chang-Seon;Kim, Dong-Hee;Yun, Mi-Young;Choi, Yong-Seok;Kim, Sung-Hoon;Song, Gyu-Yong
    • YAKHAK HOEJI
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    • v.50 no.5
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    • pp.338-344
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    • 2006
  • A novel series of 4-senecioyloxymethyl-6,7-dimethoxycoumarin, isolated from Crinum latifolium, was prepared by reacting 4-bromomethyl or 4-bromomethyl-6,7- dimethoxycoumarin with various carboxylic acids and examined for their anti-angiogenic activities in human umbilical vein endothelial cells (HUVECs). Among them, 4e, 4f, 4g and 4i with noncyclic moiety exhibited potent anti-angiogenic activity. However, compounds with cyclic moiety such as phenyl, pyridinyl, thiophenyl and furanyl group did not exhibit any anti-angiogenic activity. Also, compounds 4f and 4g which exhibited strong anti-angiogenic activity in a dose-dependent manner showed antitumor activity.

GENETIC AND BIOCHEMICAL ANALYSIS OF A THERMOSTABLE CHITOSANASE FROM Bacillus sp. CK4

  • Yoon, Ho-Geun;Cho, Hong-Yon
    • Proceedings of the Korean Society for Applied Microbiology Conference
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    • 2000.04a
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    • pp.157-167
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    • 2000
  • A thermostable chitosanase gene from the isolated strain, Bacillus sp. CK4, was cloned, and its complete DNA sequence was determined. The thermostable chitosanase gene was composed of an 822-bp open reading frame which encodes a protein of 242 amino acids and a signal peptide corresponding to a 30 kDa enzyme in size. The deduced amino acid sequence of the chitosanase from Bacillus sp. CK4 exhibits 76.6%, 15.3%, and 14.2% similarities to those from Bacillus subtilis, Bacillus ehemensis, and Bacillus circulans, respectively. C-terminal homology analysis shows that Bacillus sp. CK4 belongs to the Cluster III group with Bacillus subtilis. The size of the gene was similar to that of a mesophile, Bacillus subtilis showing a higher preference for codons ending in G or C. The functional importance of a conserved region in a novel chitosanase from Bacillus sp. CK4 was investigated. Each of the three carboxylic amino acid residues were changed to E50D/Q, E62D/Q, and D66N/E by site-directed mutagenesis. The D66N/E mutants enzymes had remarkably decreased kinetic parameters such as $V_{max}$ and k$\sub$cat/, indicating that the Asp-66 residue was essential for catalysis. The thermostable chitosanase contains three cysteine residues at position 49, 72, and 211. Titration of the Cys residues with DTNB showed that none of them were involved in disulfide bond. The C49S and C72S mutant enzymes were as stable to thermal inactivation and denaturating agents as the wild-type enzyme. However the half-life of the C211S mutant enzyme was less than 60 min at 80$^{\circ}C$, while that of the wild type enzyme was about 90 min. Moreover, the residual activity of C211S was substantially decreased by 8 M urea, and fully lost catalytic activity by 40% ethanol. These results show that the substitution of Cys with Ser at position 211 seems to affect the conformational stability of the chitosanase.

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Effects of Acid Modification on Pb(II) and Cu(II) Adsorption of Bamboo-based Activated Carbon (대나무 활성탄의 산 개질이 납과 구리 이온의 흡착에 미치는 영향)

  • Lee, Myoung-Eun;Chung, Jae-Woo
    • Journal of the Korea Organic Resources Recycling Association
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    • v.24 no.1
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    • pp.3-10
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    • 2016
  • Effects of acid ($HNO_3$ and HCl) modification on the adsorption properties of Pb(II) and Cu(II) onto bamboo-based activated carbon (BAC) were investigated through a series of batch experiments. The carbon content increased and oxygen content decreased with acid treatment. $HNO_3$ induced carboxylic acids and hydroxyl functional groups while HCl added no functional group onto BAC. The pseudo-second order model better described the kinetics of Pb(II) and Cu(II) adsorption onto experimented adsorbents, indicating that the rate-limiting step of the heavy metal sorption is chemical sorption involving valency forces through sharing or exchange of electrons between the adsorbate and the adsorbent. The equilibrium sorption data followed both Langmuir and Freundlich isotherm models. The adsorption capacities of BAC were affected by the surface functional groups added by acid modification. The adsorption capacities were enhanced up to 36.0% and 27.3% for Pb(II) and Cu(II), respectively by the $HNO_3$ modification, however, negligibly affected by HCl.

Chemical Structural Features of Humic-like Substances (HULIS) in Urban Atmospheric Aerosols Collected from Central Tokyo with Special Reference to Nuclear Magnetic Resonance Spectra

  • Katsumi, Naoya;Miyake, Shuhei;Okochi, Hiroshi
    • Asian Journal of Atmospheric Environment
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    • v.12 no.2
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    • pp.153-164
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    • 2018
  • We measured $^1H$ and $^{13}C$ nuclear magnetic resonance (NMR) spectra of Humic-like substances (HULIS) in urban atmospheric aerosols isolated by diethylaminoethyl (DEAE) and hydrophilic-lipophilic balance (HLB) resin to characterize their chemical structure. HULIS isolated by DEAE resin were characterized by relatively high contents of aromatic protons and relatively low contents of aliphatic protons in comparison with HULIS isolated by HLB resin, while the contents of protons bound to oxygenated aliphatic carbon atoms were similar. These results were consistent with the results of the $^{13}C$ NMR analysis and indicate that hydrophobic components were more selectively adsorbed onto HLB, while DEAE resins selectively retained aromatic carboxylic acids. Furthermore, we demonstrated that the chemical structural features of HULIS were significantly different between spring and summer samples and that these disparities were reflective of their different sources. The estimated concentrations of HULIS in spring were found to be regulated by vehicle emissions and pollen dispersion, while the behavior of HULIS in summer was similar to photochemical oxidant and nitrogen dioxide concentrations. The proportion of aliphatic protons for summer samples was higher than that for spring samples, while the proportion of aromatic protons for summer samples was lower than that for spring samples. These seasonal changes of the chemical structure may also involve in their functional expression in the atmosphere.