• Title/Summary/Keyword: $^1H-NMR$

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Melanin Biosynthesis Inhibition Effects of Ginsenoside Rb2 Isolated from Panax ginseng Berry

  • Lee, Dae Young;Jeong, Yong Tae;Jeong, Sang Chul;Lee, Mi Kyoung;Min, Jin Woo;Lee, Jae Won;Kim, Geum Soog;Lee, Seung Eun;Ahn, Young Sup;Kang, Hee Cheol;Kim, Jin Hee
    • Journal of Microbiology and Biotechnology
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    • v.25 no.12
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    • pp.2011-2015
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    • 2015
  • Ginsenoside Rb2 (Gin-Rb2) was purified from the fruit extract of Panax ginseng. Its chemical structure was measured by spectroscopic analysis, including HR-FAB-MS, 1H-NMR, and IR spectroscopy. Gin-Rb2 decreased potent melanogenesis in melan-a cells, with 23.4% at 80 μM without cytotoxicity. Gin-Rb2 also decreased tyrosinase and MITF protein expression in melan-a cells. Furthermore, Gin-Rb2 presented inhibition of the body pigmentation in the zebrafish in vivo system and reduced melanin contents and tyrosinase activity. These results show that Gin-Rb2 isolated from P. ginseng may be an effective skin-whitening agent via the in vitro and in vivo systems.

Screening System for Chitin Synthase II Inhibitors from Natural Resources and its Inhibitor Prodigiosin

  • Hwang, Eui-Il;Kim, Young-Kook;Lee, Hyang-Bok;Kim, Hong-Gi;Kim, Sung-Uk
    • Journal of Microbiology and Biotechnology
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    • v.10 no.2
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    • pp.251-257
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    • 2000
  • Chitin synthases are identified as key enzymes of chitin biosynthesis in most of the fungi. Among them, chitin synthase II has been reported to be and essential enzyme in chitin biosynthesis, and exists as a membrane-bound form. To search and screen new antifungal agents from natural resources to inhibit chitin synthase II, the assay conditions were established using the enzyme isolated from Saccharomyces cerevisiae ECY38-38A(pAS6) that overproduces only chitin synthase II. This enzyme was activated only by partial proteolysis with trypsin. Its actibity reached the maximum at $80{\;}\mu\textrm{g}/ml$ of trypsin and was strongly stimulated by 2.0 mM $Co^{2+}$, 1.0 nM UDP-[$^{14}C$]-GicNAc, and 32 mM free-GlcNAc. Under these assay conditions, the highest chitin synthase II activity was observed by incubation at $30^{\circ}C$ for 90 min. However, and extremely narrow range of organic solvents up to as much as 25% of DMSO and 25% of MeOH was useful for determining optimal assay conditions. After a search or potent inhibitors of chitin synthase II from natural resources, prodigiosin was isolated from Serratia marcescens and purified by solvent extration and silica gel column chromatographies. The structure of prodigiosin was determined by UV, IR, Mass spectral, and NMR spectral analyses. Its molecular weight and formula were found to be 323 and $C_{20}H_{25}N_{3}O$, respectively. Prodigiosin ingibited chitin synthase II by 50% at the concentration of $115{\;}\mu\textrm{g}/ml$.

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Fabrication of Micro Patterned Fibronectin for Studying Adhesion and Alignment Behavior of Human Dermal Fibroblasts

  • Lee, Seung-Jae;Son, Young-Sook;Kim, Chun-Ho;Choi, Man-Soo
    • Macromolecular Research
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    • v.15 no.4
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    • pp.348-356
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    • 2007
  • The aim of this study was to fabricate a submicro-and micro-patterned fibronectin coated wafer for a cell culture, which allows the positions and dimensions of the attached cells to be controlled. A replica molding was made into silicon via a photomask in quartz, using E-beam lithography, and then fabricated a polydimethylsiloxane stamp using the designed silicon mold. Hexadecanethiol $[HS(CH_2){_{15}}CH_3]$, adsorbed on the raised plateau of the surface of polydimethylsiloxane stamp, was contact-printed to form self-assembled monolayers (SAMs) of hexadecanethiolate on the surface of an Au-coated glass wafer. In order to form another SAM for control of the surface wafer properties, a hydrophilic hexa (ethylene glycol) terminated alkanethiol $[HS(CH_2){_{11}}(OCH_2CH_2){_6}OH]$ was also synthesized. The structural changes were confirmed using UV and $^1H-NMR$ spectroscopies. A SAM terminated in the hexa(ethylene glycol) groups was subsequently formed on the bare gold remaining on the surface of the Aucoated glass wafer. In order to aid the attachment of cells, fibronectin was adsorbed onto the resulting wafer, with the pattern formed on the gold-coated wafer confirmed using immunofluorescence staining against fibronectin. Fibronectin was adsorbed only onto the SAMs terminated in the methyl groups of the substrate. The hexa (ethylene glycol)-terminated regions resisted the adsorption of protein. Human dermal fibroblasts (P=4), obtained from newborn foreskin, only attached to the fibronectin-coated, methyl-terminated hydrophobic regions of the patterned SAMs. N-HDFs were more actively adhered, and spread in a pattern spacing below $14{\mu}m$, rather than above $17{\mu}m$, could easily migrate on the substrate containing spacing of $10{\mu}m$ or less between the strip lines.

Synthesis and Characterization of Biodegradable Elastic Hydrogels Based on Poly(ethylene glycol) and Poly(${\varepsilon}-caprolactone$) Blocks

  • Im, Su-Jin;Choi, You-Mee;Subramanyam, Elango;Huh, Kang-Moo;Park, Ki-Nam
    • Macromolecular Research
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    • v.15 no.4
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    • pp.363-369
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    • 2007
  • Novel biodegradable elastic hydrogels, based on hydrophilic and hydrophobic polymer blocks, were synthesized via the radical crosslinking reaction of diacrylates of poly(ethylene glycol) (PEG) and poly(${\varepsilon}-caprolactone$) (PCL). PEG and PCL diols were diacrylated with acryloyl chloride in the presence of triethylamine, with the reaction confirmed by FT-IR and $^1H-NMR$ measurements. The diacrylate polymers were used as building-blocks for the syntheses of a series of hydro gels, with different block compositions, by simply varying the feed ratios and molecular weights of the block components. The swelling ratio of the hydrogels was controlled by the balance between the hydrophilic and hydrophobic polymer blocks. Usually, the swelling ratio increases with increasing PEG content and decreasing block length within the network structure. The hydrogels exhibited negative thermo-sensitive swelling behavior due to the coexistence of hydrophilic and hydrophobic polymer components in their network structure, and such thermo-responsive swelling/deswelling behavior could be repeated using a temperature cycle, without any significant change in the swelling ratio. In vitro degradation tests showed that degradation occurred over a 3 to 8 month period. Due to their biodegradability, biocompatibility, elasticity and functionality, these hydrogels could be utilized in various biomedical applications, such as tissue engineering and drug delivery systems.

An Efficient Method for Synthesis of PEO-Based Macromonomer and Macroinitiator

  • Kim, Jung-Ahn;Choi, Song-Yee;Kim, Kyung-Min;Go, Da-Hyeon;Jeon, Hee-Jeong;Lee, Jae-Yeol;Park, Hyeong-Soo;Lee, Cheol-Han;Park, Heung-Mok
    • Macromolecular Research
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    • v.15 no.4
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    • pp.337-342
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    • 2007
  • The n-butyllithium-initiated ring-opening polymerization of ethylene oxide, in a mixture of benzene and dimethylsulfoxide (DMSO), between $25-45^{\circ}C$, with potassium tert-butoxide, is a useful and powerful method to control the molecular weight as well as achieve a quantitative chain-end functionalization yield of the resulting polymeric alkoxide via a one pot synthesis. The molecular weight of the product could be controlled by adjusting the ratio of grams of monomer to moles of initiators, such as n-butyllithium ([n-BuLi]) and potassium t-butoxide ([t-BuOK]). The yields for the macromonomer and ${\omega}-brominated$ poly(ethylene oxide) (PEO) were quantitative in relation to the chain-end functionalizations of the polymeric alkoxide formed. The resulting products were characterized by a combination of $^1H-NMR$ spectroscopic and size exclusion chromatographic analyses.

Synthesis of Polystyrene-b-Poly(ethylene oxide)-b-Polylactide Copolymers via Sequential Anionic and Ring-Opening Polymerizations (순차적 음이온 및 개환중합반응을 통한 폴리스티렌-폴리에틸렌옥사이드-폴리락티드 블록공증합체의 합성)

  • Song, Jie;Cho, Byoung-Ki
    • Polymer(Korea)
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    • v.33 no.5
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    • pp.458-462
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    • 2009
  • We have synthesized ABC linear triblock copolymers, i.e., polystyrene-b-poly(ethylene oxide)-b-polylactide, via sequential anionic and ring-opening polymerizations. In the first anionic polymerization step, styrene was polymerized in cyclohexane using sec-butyllithium as the initiator. Poly (styryl) lithium was hydroxylated by the addition of ethylene oxide, and the subsequent protonation with methanolic HCl. In the second anionic polymerization step, potassium naphthalenide was used to deprotonate the hydroxyl group of the PS to generate the macroinitiator of PS-$O^-K^+$. Polymerization of ethylene oxide was performed in THF and terminated with methanolic HCl. In the ring-opening polymerization step, the PS-b-PEO-$AlEt_2$ macroinitiator was prepared from an $AlEt_3$/pyridine system in THF, and the polymerization of lactide was performed at $90^{\circ}C$. The resulting block copolymers showed well-defined molecular weights and narrow molecular weight distributions as revealed by $^1H$- NMR spectroscopy and gel permeation chromatography (GPC).

Preparation and Characterizations of Poly(ethylene glycol)-Poly(ε-caprolactone) Block Copolymer Nanoparticles

  • Choi, Chang-Yong;Chae, Su-Young;Kim, Tai-Hyoung;Jang, Mi-Kyeong;Cho, Chong-Su;Nah, Jae-Woon
    • Bulletin of the Korean Chemical Society
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    • v.26 no.4
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    • pp.523-528
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    • 2005
  • Diblock copolymers with different poly($\varepsilon$-caprolactone) (PCL) block lengths were synthesized by ringopening polymerization of $\varepsilon$-caprolactone in the presence of monomethoxy poly(ethylene glycol) (mPEG-OH, MW 2000) as initiator. The self-aggregation behaviors of the diblock copolymer nanoparticle, prepared by the diafiltration method, were investigated by using $^1H$ NMR, dynamic light scattering (DLS), and fluorescence spectroscopy. The PEG-PCL block copolymers formed the nano-sized self-aggregate in an aqueous environment by intrsa- and/or intermolecular association between hydrophobic PCL chains. The critical aggregation concentrations (cac) of the block copolymer self-aggregate became lower with increasing hydrophobic PCL block length. On the other hand, reverse trends of mean hydrodynamic diameters were measured by DLS owing to the increasing bulkiness of the hydrophobic chains and hydrophobic interaction between the PCL microdomains. The hydrodynamic diameters of the block copolymer nanoparticles, measured by DLS, were in the range of 65-270 nm. Furthermore, the size of the nanoparticles was scarcely affected by the concentration of the block copolymers in the range of 0.125-5 mg/mL owing to the negligible interparticular aggregation between the self-aggregated nanoparticles. Considered with the fairly low cac and nanoparticle stability, the PEG-PCL nanoparticles can be considered a potential candidate for biomedical applications such as drug carrier or imaging agent.

Evaluation of Cytotoxicity to Rat Platelets by Menadione-Glutathione Conjugate and its Stability in Biological Assay System (Menadione의 대사체인 Menadione-Glutathione Conjugate(MEN-SG)가 흰쥐 혈소판에 미치는 세포독성의 평가 및 MEN-SG의 안정성에 관한 연구)

  • Seo, Dong-Chul;Chung, Sun-Hwa;Lee, Joo-Young;Kim, Mee-Jeong;Chung, Jin-Ho
    • Toxicological Research
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    • v.11 no.2
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    • pp.295-302
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    • 1995
  • Menadione-ghitathione conjugate (MEN-SG), a metabolite of menadione, is known to be a redoxcycler in rat hepatocyte subcellular fraction. Therefore, it was assumed that MEN-SG could exert cytotoxlclty to ral platelets, another target tissue of menadione. We first synthesized MEN-SG, the identity of which was verified by mass, $^1{H}$-NMR and UV-visible spectra. In addition, the stability of MEN-SG was investigated in biological assay system. MEN-SG was degraded in a time-dependent manner in DMSO which had been used as a vehicle and thus, tris-HCl buffer was used as a vehicle of MEN-SG despite the low solubility in it. Perchloric acid as well as platelets itself did not affect the stability of MEN-SG. Our next attempt was the evaluation of cytotoxicity of MEN-SG in rat platelets. MEN-SG did not induce cytotoxicity to rat platelets measured by two different methods, LDH release and turbidity changes. The extents of oxygen consumption by MEN-SG in intact platelets were significantly lower than those by menadione, though it had been observed that oxygen consumptions by menadione and MENSG were similar in subcellular fractioas of platelets. These results suggest that MEN-SG is not toxic to rat platelets despite its redox cycling capacity and glutathione conjugation reaction of menadione could be regarded as a detoxification process.

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Effects of PEO Additions on the Mechanical and Thermal Proprieties of PLA/PBAT Blends (폴리에틸렌옥사이드가 PLA/PBAT 블렌드 물성에 미치는 영향)

  • Jang, Hyunho;Kwon, Sangwoo;Eom, Yoojun;Yoo, Seungwoo;Park, Su-il
    • KOREAN JOURNAL OF PACKAGING SCIENCE & TECHNOLOGY
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    • v.26 no.2
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    • pp.93-98
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    • 2020
  • The blends of Poly(lactic acid) (PLA) and Poly(butylene adipate-co-terephthalate) (PBAT) have been recognized as a replacement for commodity plastic films and bags in biodegradable packaging industries. The purpose of this study is to identify changes in the thermal and mechanical properties of PLA/PBAT blends with the addition of poly(ethylene oxide)(PEO). PLA (80%) and PBAT (20%) were melt mixed with 0 to 10 phr of PEO and processed using a hot press. The addition of PEO into PLA/PBAT increased the elongation at break and improved thermal stability. With PEO addition, two melting temperature (Tm) peaks of PLA/PBAT merged into one peak showing improved miscibility. The result of this study showed that the addition of PEO increased the ductility and thermal stability of PLA/PBAT blends.

Antifungal Activity Against Colletotrichum spp. of Curcuminoids Isolated from Curcuma longa L. Rhizomes

  • Cho Jun-Young;Choi Gyung-Ja;Lee Seon-Woo;Jang Kyoung-Soo;Lim He-Kyoung;Lim Chi-Hwan;Lee Sun-Og;Cho Kwang-Yun;Kim Jin-Cheol
    • Journal of Microbiology and Biotechnology
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    • v.16 no.2
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    • pp.280-285
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    • 2006
  • Methanol extract of the rhizomes of turmeric, Curcuma longa L., effectively controlled the development of red pepper anthracnose caused by Colletotrichum coccodes. In addition three antifungal substances were identified from the methanol extract of C. longa rhizomes as curcumin, demethoxycurcumin, and bisdemethoxycurcumin using mass and $^{1}H-NMR$ spectral analyses. The curcuminoids in a range $0.4-100\;{\mu}g/ml$ effectively inhibited the mycelial growth of three red pepper anthracnose pathogens, C. coccodes, C. gloeosporioides, and C. acutatum. The three curcuminoids inhibited mycelial growth of C. coccodes and C. gloeosporioides to an extent similar to the synthetic fungicide dithianon did, but the synthetic agent was a little more effective against C. acutatum. The curcuminoids also effectively inhibited spore germination of C. coccodes, and bisdemethoxycurcumin was the most active. Among the three curcuminoids, only demethoxycurcumin was effective in a greenhouse test in suppressing red pepper anthracnose caused by C. coccodes.