• Title/Summary/Keyword: Methyl benzoate

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Functionalized Raspberry-Like Microparticles obtained by Assembly of Nanoparticles during Electrospraying

  • Cho, Eun Chul;Hwang, Yoon Kyun;Jeong, Unyong
    • Bulletin of the Korean Chemical Society
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    • v.35 no.6
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    • pp.1784-1788
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    • 2014
  • The present study suggests a novel method to produce raspberry-like microparticles containing diverse functional materials inside. The raspberry-like microparticles were produced from a random assembly of uniformly-sized poly(methyl methacrylate) (PMMA) nanoparticles via electrospraying. The solution containing the PMMA nanoparticles were supplied through the inner nozzle and compressed air was emitted through the outer nozzle. The air supply helped fast evaporation of acetone, so it enabled copious amount of microparticles as dry powder. The microparticles were highly porous both on the surface and interiors, hence various materials with a function of UV-blocking ($TiO_2$ nanoparticles and methoxyphenyl triazine) or anti-aging (ethyl(4-(2,3-dihydro-1H-indene-5-carboxyamido) benzoate)) were loaded in large amount (17 wt % versus PMMA). The surface and interior structures of the microparticles were dependent on the characteristics of functional materials. The results clearly suggest that the process to prepare the raspberry-like microparticles can be an excellent approach to generate functional microstructures.

Cytotoxic and Antimicrobial Activities of Bioactive Monoterpenophenols

  • Oh In Kio;Lee Hyun Ok;Ahn Jong Woong;Kim Hyung Min;Shin Ji Hee;Lim Jin A;Chun Hyun Ja;Baek Seung Hwa
    • Journal of Physiology & Pathology in Korean Medicine
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    • v.16 no.6
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    • pp.1270-1276
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    • 2002
  • Compounds 1 - 12 were tested for their growth inhibitory effects against tumor cell lines using two different 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl-2H-tetrazolium bromide (MTT) and sulforhodamine B protein (SRB) assays and antimicrobial activity. The cytotoxic activity of methyl-4-[{(2E)-3,7-dimethyl-2,6-octadienyl}oxy]-3-methoxy benzoate (1) exhibit more active than that of 5-fluorouracil (11) on human oral epithelioid carcinoma (KB, ATCC No. OCL 17) cell lines. But this compound (1) on human skin melanoma (SK-MEL-3, HBT 69) cell lines shows less active than that of adriamycin (12). However, compound 9 showed the antimicrobial activity against S. epidermidis (MIC, 15.625 ㎍/㎖), S. aureus, C. albicans (MIC, 31.25 ㎍/㎖), S. mutans, S. typhimurium, P. putida (MIC. 125 ㎍/㎖) and P. aeruginosa (MIC, 500 ㎍/㎖).

Purification and Characterization of Phenoxazinone Synthase from Streptomyces sp. V-8 Mutant Producing Adenoside Deaminase Inhibitor (아데노신 탈아미노화 효소 억제제를 생산하는 Streptomyces sp. V-8의 변이종으로부터 페녹사지논 합성효소의 분리 및 특성)

  • 김경자;조성진
    • YAKHAK HOEJI
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    • v.43 no.1
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    • pp.68-76
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    • 1999
  • Phenoxazinone synthase catalyzes the oxidative condensation of two molecules of substituted o-aminophenol to the phenoxazinone chromophore of actinomycin. Mutant strain, Streptomyces sp. V-8-M-1 producing higher phenoxazinone synthase, was obtained from Streptomyces sp. V-8 by treatment of N-methyl-N'-nitro-N-nitrosoguanidine. The phenoxazinone synthase was purified from extract of mutant strain of Streptomyces sp. V-8-M-l by successive steps of streptomycin sulfate, ammonium sulfate precipitation. DEAE-cellulose and Sephadex G-200 column chromatography. Molecular weight of the enzyme was 360,000 daltons. The enzyme was composed of octamer of a single subunit of 45,000 daltons. The Km value and Vmax value for 3-HAA were $14.9{\;}{\mu}M$ and 9.5 mg/U, respectively. The optimal pH and temperature for the enzyme activity were 9.0 and $25~30^{\circ}C$, respectively. Treatment of the enzyme with group specific reagents, phenylglyoxal, p-hydroxymercury-benzoate, Nbromosuccinimide, 5.5'-dithiobis-nitrobenzoic acid and ethylmaleimide resulted in loss of enzyme activity, which shows arginine and cysteine residues are at or near the active site.

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Characterization of Mitochondrial NADH Dehydrogenase in Lentinus edodes (표고버섯의 미토콘드리아성 NADH 탈수소효소의 특성)

  • Kim, Eun-Mi;Min, Ji-Young;Min, Tae-Jin
    • The Korean Journal of Mycology
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    • v.26 no.1 s.84
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    • pp.119-126
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    • 1998
  • Mitochondria were isolated from Lentinus edodes and properties of the mitochondrial NADH dehydrogenase were studied. Optimal pH, temperature, and thermal stability of the enzyme were estimated to be 7.6, $33^{\circ}C$, and stable for one hour at $50^{\circ}C$. The apparent $K_m$ for the NADH was 0.33 mM. This enzyme catalyzed to transfer electrons from NADH to ferricyanide, decylubiquinone, and 2,6-dichloro-phenol-indophenol. 0.5 mM antimycin A and 0.01 mM dibromothymoquinone strongly inhibited 87.8% and 76.5% of the enzyme activities. 0.01 mM oligomycin known as an inhibitor of ATPase also strongly inhibited 79.2% of activities. 0.5 mM 5,5'-dithiobis-(2-nitrobenzoic acid) and 1.0 mM N-ethylmaleimide known as a modifier of SH group inhibited 50.4% and 36.7% of activities. 1 mM ethyl 2,4-dihydroxy-6-methyl benzoate and 10 mM orcinol, which had been known as an antibiotics isolated from Umbilicaria vellea according to our previous work, stimulated 68.4% and 48.1% of the enzyme activities.

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Structures of OH Emulsion Prepared with Saccharide Surfactants (당류계 계면활성제로 제조된 O/W 에멀젼의 구조)

  • 홍세흠;한창규;조춘구
    • Journal of the Society of Cosmetic Scientists of Korea
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    • v.26 no.1
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    • pp.261-274
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    • 2000
  • The o/w emulsions were prepared with saccharide surfactants which were sucrose monostearate(S160), sucrose distearate(S110), and POE(20) methyl glucose stearate(SSE20). And for emulsion the oils used were n-hydocarbon, squalane(SQ), liquid paraffin(LP), octylpalmitate(OP), octylstearate(OS), alkyl benzoate(AB), isostearyl benzoate(ISB). The structures of o/w emulsion droplet were investigated by laser light scattering and the fractal dimensions were calculated from light intensity curves. Increasing of concentration, chain length, and nonpolarity of oils, fractal dimensions of emulsion droplets were found greater. In general fiactal dimensions were varied from 1.7 to 2.8 and its structures were fractal But the fractal dimensions of octadecane( $C_{18}$), 50, and LP emulsified with S110 and S160 were varied from 3.0 to 3.2 and its structures were more dense. The overall fractal dimensions of S110 and S160 were varied from 2.1 to 2.6, that of SSE20 were varied from 1.5 to 2.1. So it was found that the structures of SSE20 system were less compact than that of S110 and S 160 system, because the hindrance effect of polyoxyehtylene group of SSE20 was stronger than that of sucrose of S160. The strucures of emulsion droplets changed according to the nature of emulsifiers and to compositions of oil substances which they contained, and the structures were found similar when the hydophilic moiety of emulsifiers was same.

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Synthesis and Characterization of Photosensitive Polyimides Containing Alicyclic Structure (지방족고리 구조를 함유하는 감광성 폴리이미드 수지의 합성 및 특성 평가)

  • 심종천;최성묵;심현보;권수한;이미혜
    • Polymer(Korea)
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    • v.28 no.6
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    • pp.494-501
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    • 2004
  • A new alkali developable photosensitive poly(amic acid) (PAA-0) with transmittance at 400 nm was synthesized from cyclobutane-1,2,3,4-tetracarboxylic dianhydride, 2-(methacryloyloxy)ethyl-3,5-diamino-benzoate and 1,3-bis(3-aminopropyl)-1,1,3,3-tetramethyl disiloxane in N-methyl-2-pyrrolidinone. Photosensitivity of the PAA-0 was investigated at 365-400 nm in the presence of a photoinitiator using a high pressure mercury lamp. The photo-cured poly(amic acid) was insoluble toward aqueous 2.38 wt% tetramethylammonium hydroxide solution. Negative pattern of the PAA-0 with 25 ${\mu}{\textrm}{m}$ resolution was obtained by developing with 2.38 wt% tetramethylammonium hydroxide solution after exposure of 600 mJ/$\textrm{cm}^2$ in the presence of 2,2-dimethoxy-2-phenyl-acetophenone as a photoinitiator. The patterned poly(amic acid) was converted to polyimide by thermal curing at 25$0^{\circ}C$ for 50 min, which showed chemical resistance against photoresist stripper as well as good transmittance at 400 nm.

Antiferroelectric Liquid Crystal from Bent-Core Molecule with Vinyl End Group

  • Lee, Chong-Kwang;Kwon, Soon-Sik;Kim, Tae-Sung;Shin, Sung-Tae;Choi, Hong;Choi, E. Joon;Kim, Sea-Yun;Zin, Wang-Choel;Kim, Dae-Choel;Chien, Liang-Chy
    • Bulletin of the Korean Chemical Society
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    • v.25 no.8
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    • pp.1171-1176
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    • 2004
  • Three banana-shaped achiral compounds, 4-chloro-1,3-phenylene bis [4-{4-(undecenyloxy)phenyl imino-methyl} benzoate] derivatives, were synthesized with variation of a substituent (x=H, F, Cl); their antiferro-electric properties are described. The smectic mesophases, including a switchable chiral smectic C(Sm $C^{\ast}$) phase, were characterized by differential scanning calorimetry, polarizing optical microscopy, triangular wave method, and X-ray diffractometry. The presence of vinyl groups at the terminals of linear side wings in the banana-shaped achiral molecules induced a decrease in melting temperature and formation of the switchable Sm $C^{\ast}$ phase in the melt. The smectic phase having a lateral fluorine-substituent at 3-position of the Schiff's base moiety showed antiferroelctric switching, and the value of spontaneous polarization on reversal of an applied electric field was 250 nC/$cm^2$ .

Assessment of ALS-Inhibiting Herbicides Tolerance in Pepper Cultivars (ALS 저해형 제초제 내성 고추품종 검정)

  • Pornprom, Tosapon;Pyon, Jong-Yeong
    • Korean Journal of Weed Science
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    • v.17 no.3
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    • pp.325-333
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    • 1997
  • Selection of pepper (Capsicum sp.) cultivars tolerant to acetolactate synthase (ALS)-inhibiting herbicides {imazethapyr, 2-[4,5-dihydro-4-methyl-4-(1-methylethyl)-5-oxo-1H-imidazol-2-yl]-5-ethyl-3=pyridine-carboxylic acid, and primisulfuron methyl 2-[[[[[4,6-bis(difluoromethoxy)-2-pyrimidinyl]amino] carbonyl]amino]sulfonyl]benzoate} was investigated. Pepper cultivars such as Red Top, Happy Dry, Golden Tower, and Hagyeorae showed relatively tolerant response to imazethapyr, while cultivars; Korea, Cheongyang, Oriental Glory, and Hanam were susceptible. Red Horn, Jopoong, Kwangbok, and Wangcho cultivars were tolerant to primisulfuron whereas Korea, Dahhong, Chamjoah, and Poongchon cultivars were susceptible. Determination of growth inhibition by ALS-inhibiting herbicides showed that the $I_{50}$ estimates of growth from the susceptible- and tolerant-cultivars were 0.075 and 0.20kg ai/ha for imazethapyr; 0.06 and 0.16kg ai/ha for primisulfuron, respectively. Furthermore, the $GR_{50}$ estimates of growth from the susceptible and tolerant cultivars were 0.05 and 0.20kg ai/ha for imazethapyr; 0.07 and 0.16kg ai/ha for primisulfuron, respectively. This result, based on the $GR_{50}$ and $I_{50}$ values, indicates that responses of pepper to ALS-inhibiting herbicides between tolerant- and susceptible-cultivars were different about 3- to 4-fold to imazethapyr, and 2- to 3-fold to primisulfuron.

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Phytotoxicity Response of Herbicide in Infant Seeding Machine Transplanting of Rice(Oryza sativa L.) - I. Difference of seedling age (벼 어린모 기계이앙시(機械移秧時) 제초제(除草劑)의 약해반응(藥害反應) 연구(硏究) - I. 육묘기간(育苗期間)의 차이(差異)에 따른 제초제(除草劑)의 약해(藥害))

  • Im, I.B.;Baek, N.H.;Shim, I.S.;Lee, S.Y.
    • Korean Journal of Weed Science
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    • v.15 no.2
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    • pp.115-120
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    • 1995
  • This experiment was conducted in the paddy field to investigate the influence of bensulfuron (methyl-2-[[[[[(4,6-dimethoxypyrimidin-2-yl)amino]carbonyl]amino]sulfonil]methyl]benzoate)+butachlor (N-(butoxymethyl)-2-chloro-2',6'-diethyl acetanilide) and bensulfuron+mefenacet(2-(1,3-benzothiazol-2-yloxy)-N-methylacetanilide) for seedling age of rice with Dongjinbyeo of medium-late-maturing variety, Hwaseongbyeo of medium-maturing variety and Namwonbyeo of early-maturing variety. Two herbicide applications interfered with the early growth of all rice varieties, the root was especially damaged more than the shoot. The phytotoxicity of bensulfuron+butachlor and bensulfuron+mefenacet was not significant statistically and the phytotoxicity of these herbicides for seedling age was apt to be similar, also. Twenty and 35days seedlings of Dongjinbyeo and Hawseongbyeo had more growth amount than 8days seedlings, but Namwonbyeo had opposite trend. The number of maximum tillers in the plots applied herbicides were fewer than untreated control but, the percentage of productive tillers was higher than those. Heading date for Namwonbyeo was delayed 2, 1-2 and 2-3days on 35, 20 and 8days seedlings by herbicide application, respectively.

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Sesquiterpenoids Bioconversion Analysis by Wood Rot Fungi

  • Lee, Su-Yeon;Ryu, Sun-Hwa;Choi, In-Gyu;Kim, Myungkil
    • 한국균학회소식:학술대회논문집
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    • 2016.05a
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    • pp.19-20
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    • 2016
  • Sesquiterpenoids are defined as $C_{15}$ compounds derived from farnesyl pyrophosphate (FPP), and their complex structures are found in the tissue of many diverse plants (Degenhardt et al. 2009). FPP's long chain length and additional double bond enables its conversion to a huge range of mono-, di-, and tri-cyclic structures. A number of cyclic sesquiterpenes with alcohol, aldehyde, and ketone derivatives have key biological and medicinal properties (Fraga 1999). Fungi, such as the wood-rotting Polyporus brumalis, are excellent sources of pharmaceutically interesting natural products such as sesquiterpenoids. In this study, we investigated the biosynthesis of P. brumalis sesquiterpenoids on modified medium. Fungal suspensions of 11 white rot species were inoculated in modified medium containing $C_6H_{12}O_6$, $C_4H_{12}N_2O_6$, $KH_2PO_4$, $MgSO_4$, and $CaCl_2$ for 20 days. Cultivation was stopped by solvent extraction via separation of the mycelium. The metabolites were identified as follows: propionic acid (1), mevalonic acid lactone (2), ${\beta}$-eudesmane (3), and ${\beta}$-eudesmol (4), respectively (Figure 1). The main peaks of ${\beta}$-eudesmane and ${\beta}$-eudesmol, which were indicative of sesquiterpene structures, were consistently detected for 5, 7, 12, and 15 days These results demonstrated the existence of terpene metabolism in the mycelium of P. brumalis. Polyporus spp. are known to generate flavor components such as methyl 2,4-dihydroxy-3,6-dimethyl benzoate; 2-hydroxy-4-methoxy-6-methyl benzoic acid; 3-hydroxy-5-methyl phenol; and 3-methoxy-2,5-dimethyl phenol in submerged cultures (Hoffmann and Esser 1978). Drimanes of sesquiterpenes were reported as metabolites from P. arcularius and shown to exhibit antimicrobial activity against Gram-positive bacteria such as Staphylococcus aureus (Fleck et al. 1996). The main metabolites of P. brumalis, ${\beta}$-Eudesmol and ${\beta}$-eudesmane, were categorized as eudesmane-type sesquiterpene structures. The eudesmane skeleton could be biosynthesized from FPP-derived IPP, and approximately 1,000 structures have been identified in plants as essential oils. The biosynthesis of eudesmol from P. brumalis may thus be an important tool for the production of useful natural compounds as presumed from its identified potent bioactivity in plants. Essential oils comprising eudesmane-type sesquiterpenoids have been previously and extensively researched (Wu et al. 2006). ${\beta}$-Eudesmol is a well-known and important eudesmane alcohol with an anticholinergic effect in the vascular endothelium (Tsuneki et al. 2005). Additionally, recent studies demonstrated that ${\beta}$-eudesmol acts as a channel blocker for nicotinic acetylcholine receptors at the neuromuscular junction, and it can inhibit angiogenesis in vitro and in vivo by blocking the mitogen-activated protein kinase (MAPK) signaling pathway (Seo et al. 2011). Variation of nutrients was conducted to determine an optimum condition for the biosynthesis of sesquiterpenes by P. brumalis. Genes encoding terpene synthases, which are crucial to the terpene synthesis pathway, generally respond to environmental factors such as pH, temperature, and available nutrients (Hoffmeister and Keller 2007, Yu and Keller 2005). Calvo et al. described the effect of major nutrients, carbon and nitrogen, on the synthesis of secondary metabolites (Calvo et al. 2002). P. brumalis did not prefer to synthesize sesquiterpenes under all growth conditions. Results of differences in metabolites observed in P. brumalis grown in PDB and modified medium highlighted the potential effect inorganic sources such as $C_4H_{12}N_2O_6$, $KH_2PO_4$, $MgSO_4$, and $CaCl_2$ on sesquiterpene synthesis. ${\beta}$-eudesmol was apparent during cultivation except for when P. brumalis was grown on $MgSO_4$-free medium. These results demonstrated that $MgSO_4$ can specifically control the biosynthesis of ${\beta}$-eudesmol. Magnesium has been reported as a cofactor that binds to sesquiterpene synthase (Agger et al. 2008). Specifically, the $Mg^{2+}$ ions bind to two conserved metal-binding motifs. These metal ions complex to the substrate pyrophosphate, thereby promoting the ionization of the leaving groups of FPP and resulting in the generation of a highly reactive allylic cation. Effect of magnesium source on the sesquiterpene biosynthesis was also identified via analysis of the concentration of total carbohydrates. Our current study offered further insight that fungal sesquiterpene biosynthesis can be controlled by nutrients. To profile the metabolites of P. brumalis, the cultures were extracted based on the growth curve. Despite metabolites produced during mycelia growth, there was difficulty in detecting significant changes in metabolite production, especially those at low concentrations. These compounds may be of interest in understanding their synthetic mechanisms in P. brumalis. The synthesis of terpene compounds began during the growth phase at day 9. Sesquiterpene synthesis occurred after growth was complete. At day 9, drimenol, farnesol, and mevalonic lactone (or mevalonic acid lactone) were identified. Mevalonic acid lactone is the precursor of the mevalonic pathway, and particularly, it is a precursor for a number of biologically important lipids, including cholesterol hormones (Buckley et al. 2002). Farnesol is the precursor of sesquiterpenoids. Drimenol compounds, bi-cyclic-sesquiterpene alcohols, can be synthesized from trans-trans farnesol via cyclization and rearrangement (Polovinka et al. 1994). They have also been identified in the basidiomycota Lentinus lepideus as secondary metabolites. After 12 days in the growth phase, ${\beta}$-elemene caryophyllene, ${\delta}$-cadiene, and eudesmane were detected with ${\beta}$-eudesmol. The data showed the synthesis of sesquiterpene hydrocarbons with bi-cyclic structures. These compounds can be synthesized from FPP by cyclization. Cyclic terpenoids are synthesized through the formation of a carbon skeleton from linear precursors by terpene cyclase, which is followed by chemical modification by oxidation, reduction, methylation, etc. Sesquiterpene cyclase is a key branch-point enzyme that catalyzes the complex intermolecular cyclization of the linear prenyl diphosphate into cyclic hydrocarbons (Toyomasu et al. 2007). After 20 days in stationary phase, the oxygenated structures eudesmol, elemol, and caryophyllene oxide were detected. Thus, after growth, sesquiterpenes were identified. Per these results, we showed that terpene metabolism in wood-rotting fungi occurs in the stationary phase. We also showed that such metabolism can be controlled by magnesium supplementation in the growth medium. In conclusion, we identified P. brumalis as a wood-rotting fungus that can produce sesquiterpenes. To mechanistically understand eudesmane-type sesquiterpene biosynthesis in P. brumalis, further research into the genes regulating the dynamics of such biosynthesis is warranted.

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