• Title/Summary/Keyword: $^{1}H$ NMR

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Studies on Biological Activity of Wood Extractives (XVII) - Components and Antioxidant activity of Alnus firma -

  • Choi, In-Ho;Choi, Tae-Ho;Park, Youngki;Lee, Oh-Kyu;Kwon, Yeong-Han;Kang, Ha-Young;Park, Il-Kwon;Choi, Don-Ha;Shin, Sang-Chul;Lee, Hak-Ju
    • Journal of the Korean Wood Science and Technology
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    • v.34 no.2
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    • pp.95-100
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    • 2006
  • This study is to isolate bio-active compounds from Alnus firma and evaluate their antioxidant activity. Dried wood powder of A. firma was extracted by organic solvents and fractionated in the sequential extraction steps. The isolated compounds were characterized by EI-MS, $^{13}C-$ and $^1H-NMR$ including COSY, DEFT, HMQC, and HMBC. Antioxidant activities of the isolated compounds were evaluated by DPPH (1,1-diphenyl-2-picrylhydrazyl) free radical scavenging effect. From the wood of A. firma, three kinds of diarylheptanoids, alnusodiol (1), alnusonol (2) and alnusone (3), and gallic acid (4) were isolated. Among these four compounds, compound 1, 2, and 3 are isolated from A. firma for the first time. The antioxidant activity of gallic acid was 93.5% at the concentration of 100 ppm. This compound showed stronger antioxidant activity than those of other isolated compounds and the reference BHT (butylated hydroxytoluene).

Synthesis, Characterization, and Thermal Degradation of Oligo-2-[(pyridin-4-yl-)methyleneamino]pyridine-3-ol and Oligomer-Metal Complexes (올리고피리디닐메틸렌아미노피리딘올과 금속 착화물의 합성, 분석 및 열분해 특성 연구)

  • Kaya, Ismet;Gul, Murat
    • Polymer(Korea)
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    • v.32 no.4
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    • pp.295-304
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    • 2008
  • This study examined the oxidative polycondensation reaction of 2-[(pyridin-4-yl-) methyleneamino] pyridine-3-ol (2-PMAP) using air $O_2$ and NaOCl oxidants at various temperatures and times in aqueous alkaline and acidic media. Under these reactions, the optimum reaction conditions using air $O_2$ and NaOCl oxidants were determined for 2-PMAP. The number-average molecular weight ($M_n$), weight average molecular weight ($M_w$), and polydispersity index (PDI) values of O-2-PMAP synthesized in aqueous alkaline media were found to be 960, 1230, and $1.281\;g\;mol^{-1}$ using NaOCl, and 1030, 1520, and $1.476\;g\;mol^{-1}$ using air $O_2$, respectively. At the optimum reaction conditions, the yield of O-2-PMAP in aqueous alkaline media was 92.50% and 85.70% for air $O_2$ and NaOCl oxidants, respectively. The yield of O-2-PMAP in aqueous acidic media was 88.5% and 88.0% for NaOCl and air $O_2$ oxidants, respectively. O-2-PMAP was characterized by $^1H-$, $^{13}C$-NMR, FT-IR, UV-vis, SEC, and elemental analysis. TGA-DTA analysis revealed O-2-PMAP and its oligomer metal complex compounds, such as $Co^{+2}$, $Ni^{+2}$, and $Cu^{+2}$, to be stable against thermal decomposition and their weight losses at $1000^{\circ}C$ were found to be 73.0, 58.0, 53.5%, and 50.0%, respectively. In addition, the antimicrobial activities of the monomer and oligomer were tested against E. Coli (ATCC 25922), E. Faecelis (ATCC 29212), P. Auroginasa (ATCC 27853), and S. Aureus (ATCC 25923).

Synthesis and Functionalized Conditions of Quaternized Poly(vinylimidazole-co-trifluoroethylmethacrylate-co-divinylbenzene) Anion Exchange Membrane (질산성 질소 제거용 Quaternized Poly(vinylimidazole-co-trifluoroethylmethacrylate-co-divinylbenzene) 음이온교환막 제조와 관능화 조건)

  • Oh, Chang Min;Hwang, Taek Sung
    • Polymer(Korea)
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    • v.39 no.1
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    • pp.157-164
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    • 2015
  • In this study, we synthesized poly(vinylimidazole-co-trifluoroethylmethacrylate-co-divinylbenzene) (PVTD) copolymer and introduced functional group through quaternization reaction for removing nitrate from drinking water. Also, optimizing conditions (reaction time, reaction temperature and functionalized agents concentration) for introducing the functional group were confirmed. The basic properties such as water uptake, swelling ratio, electrical resistance, ion exchange capacity and anion permselectivity for removing nitrate from drinking water were measured. The optimal values of water uptake, electrical resistance and ion exchange capacity of synthesized anion exchange membrane were 51.2%, $5.4{\Omega}{\cdot}cm^2$, and 1.04 meq/g, respectively.

Isolation and Quantitative Analysis of Cinnamtannin B-1 from Osmunda japonica Thunb (고비로부터 Cinnamtannin B-1의 분리 및 함량 분석)

  • Kim, Min Suk;Woo, Kyeong Wan;Lee, Ki Ho;Lee, Hyun Joo;Lee, Seon Yu;Kang, Byoung Man;Jeon, Byung Hun;Cho, Jung Hee;Cho, Hyun Woo
    • Korean Journal of Pharmacognosy
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    • v.47 no.3
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    • pp.232-236
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    • 2016
  • In traditional Korean medicine, Osmunda japonica Thunb has been used as hemostasis and antipyretic treatment. The main compound "cinnamtannin B-1" was obtained by column chromatographic separation, and its structure was determined by spectroscopic methods, including $^1H$, $^{13}C$ NMR, and IT-TOF-ESI MS. Ash, moisture and extract content and acidinsoluble ash were monitored as identification test to establish the analytical methods. The optimum reflux extraction condition was 100% methanol extracted 30 min for 2 times. A quantitative analysis using HPLC method exhibited that the main compound at 24.7 min and its content was 0.96% in methanol extraction.

All-trans Retinoic Acid-Associated Low Molecular Weight Water-Soluble Chitosan N anoparticles Based on Ion Complex

  • Kim Dong-Gon;Choi Changyong;Jeong Young-Il;Jang Mi-Kyeong;Nah Jae-Woon;Kang Seong-Koo;Bang Moon-Soo
    • Macromolecular Research
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    • v.14 no.1
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    • pp.66-72
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    • 2006
  • The purpose of this study is to develop novel nanoparticles based on polyion complex formation between low molecular weight water-soluble chitosan (LMWSC) and all-trans retinoic acid (atRA). LMWSC nanoparticles encapsulating atRA based on polyion complex were prepared by mixing of atRA into LMWSC aqueous solution using ultrasonication. In FTIR spectra, the carbonyl group of atRA at 1690 $cm^{-1}$ disappeared or decreased when ion complexes were formed between LMWSC and atRA. In ${1}^H$ NMR spectra, specific peaks of atRA disappeared when atRA-encapsulated LMWSC (RAC) nanoparticles were reconstituted into $D_{2}O$ while specific peaks both of atRA and LMWSC appeared in $D_{2}O$/DMSO (1/3, v/v) mixture. XRD patterns also showed that the crystal peaks of atRA were disappeared by encapsulation into LMWSC nanoparticles. LMWSC nanoparticles encapsulating atRA have spherical shapes with particle size below 200 nm. The mechanism of encapsulation of atRA into LMWSC nanoparticles was thought to be an ion complex formation between LMWSC and atRA. LMWSC nanoparticles showed high atRA loading efficiency over 90$\%$ (w/w). AtRA was continuously released from nanoparticles over 10 days. In in vitro cell cytotoxicity test, free atRA showed higher cytotoxic effect against CT 26 colon carcinoma cell line on 1 day. However, RAC nanoparticles showed similar cytotoxicity against CT 26 cells on 2 day. These results suggest the potential for the introduction of LMWSC nanoparticles into various biomedical fields such as drug delivery.

Two New Diphenylethylenes from Arundina graminifolia and Their Cytotoxicity

  • Li, Yin-Ke;Zhou, Bin;Ye, Yan-Qing;Du, Gang;Niu, De-Yun;Meng, Chun-Yang;Gao, Xue-Mei;Hu, Qiu-Fen
    • Bulletin of the Korean Chemical Society
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    • v.34 no.11
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    • pp.3257-3260
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    • 2013
  • Two new diphenylethylenes, gramniphenols H and I (1 and 2), together with six known diphenylethylenes (3-8), were isolated from Arundina graminifolia. The structures of 1-8 were elucidated by spectroscopic methods including extensive 1D- and 2D-NMR techniques. Compounds 1 and 2 were evaluated for their cytotoxicity against five human tumor cell lines. Compound 1 showed cytotoxicity against PC3 cells with $IC_{50}$ value of 3.5 ${\mu}M$. Compound 2 showed cytotoxicity against NB4 and PC3 cells with $IC_{50}$ values of 3.6 and 3.8 ${\mu}M$, respectively.

New Polytriazoleimides with High Thermal and Chemical Stabilities

  • E, Yanpeng;Wan, Liqiang;Li, Yujing;Huang, Farong;Du, Lei
    • Bulletin of the Korean Chemical Society
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    • v.33 no.7
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    • pp.2193-2199
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    • 2012
  • A series of novel polytriazoleimides were prepared from various aromatic dianhydrides and a new kind of 1,2,3-triazole-containing aromatic diamine synthesized by the Cu (I)-catalyzed 1,3-dipolar cycloaddition reaction in DMAc, and characterized by FT-IR, $^1H$-NMR, XRD, DSC and TGA techniques. The results show the polytriazoleimides are soluble in most of strong polar solvents and have inherent viscosity values of 0.51-0.62 dL/g(DMAc). The polytriazoleimide films exhibit a tensile strength of 62.3-104.5 MPa and an elongation at breakage of 4.0-8.1%, a glass transition temperature ($T_g$) of $257-275^{\circ}C$, a decomposition temperature (at 5% weight loss) of $350-401^{\circ}C$ in $N_2$ atmosphere, and a dielectric constant of 2.47-3.01 at 10 MHz, which depend on the structure of the polymers. The polytriazoleimides perform good resistance to acid and alkali solution.

Synthesis and characterization of thiolated hexanoyl glycol chitosan as a mucoadhesive thermogelling polymer

  • Cho, Ik Sung;Oh, Hye Min;Cho, Myeong Ok;Jang, Bo Seul;Cho, Jung-Kyo;Park, Kyoung Hwan;Kang, Sun-Woong;Huh, Kang Moo
    • Biomaterials Research
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    • v.22 no.4
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    • pp.249-258
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    • 2018
  • Background: Mucoadhesive polymers, which may increase the contact time between the polymer and the tissue, have been widely investigated for pharmaceutical formulations. In this study, we developed a new polysaccharide-based mucoadhesive polymer with thermogelling properties. Methods: Hexanoyl glycol chitosan (HGC), a new thermogelling polymer, was synthesized by the chemical modification of glycol chitosan using hexanoic anhydride. The HGC was further modified to include thiol groups to improve the mucoadhesive property of thermogelling HGC. The degree of thiolation of the thiolated HGCs (SH-HGCs) was controlled in the range of 5-10% by adjusting the feed molar ratio. The structure of the chemically modified polymers was characterized by $^1H$ NMR and ATR-FTIR. The sol-gel transition, mucoadhesiveness, and biocompatibility of the polymers were determined by a tube inverting method, rheological measurements, and in vitro cytotoxicity tests, respectively. Results: The aqueous solution (4 wt%) of HGC with approximately 33% substitution showed a sol-gel transition temperature of approximately $41^{\circ}C$. SH-HGCs demonstrated lower sol-gel transition temperatures ($34{\pm}1$ and $31{\pm}1^{\circ}C$) compared to that of HGC due to the introduction of thiol groups. Rheological studies of aqueous mixture solutions of SH-HGCs and mucin showed that SH-HGCs had stronger mucoadhesiveness than HGC due to the interaction between the thiol groups of SH-HGCs and mucin. Additionally, we confirmed that the thermogelling properties might improve the mucoadhesive force of polymers. Several in vitro cytotoxicity tests showed that SH-HGCs showed little toxicity at concentrations of 0.1-1.0 wt%, indicating good biocompatibility of the polymers. Conclusions: The resultant thiolated hexanoyl glycol chitosans may play a crucial role in mucoadhesive applications in biomedical areas.

Nematicidal Activity of Kojic Acid Produced by Aspergillus oryzae against Meloidogyne incognita

  • Kim, Tae Yoon;Jang, Ja Yeong;Jeon, Sun Jeong;Lee, Hye Won;Bae, Chang-Hwan;Yeo, Joo Hong;Lee, Hyang Burm;Kim, In Seon;Park, Hae Woong;Kim, Jin-Cheol
    • Journal of Microbiology and Biotechnology
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    • v.26 no.8
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    • pp.1383-1391
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    • 2016
  • The fungal strain EML-DML3PNa1 isolated from leaf of white dogwood (Cornus alba L.) showed strong nematicidal activity with juvenile mortality of 87.6% at a concentration of 20% fermentation broth filtrate at 3 days after treatment. The active fungal strain was identified as Aspergillus oryzae, which belongs to section Flavi, based on the morphological characteristics and sequence analysis of the ITS rDNA, calmodulin (CaM), and β-tubulin (BenA) genes. The strain reduced the pH value to 5.62 after 7 days of incubation. Organic acid analysis revealed the presence of citric acid (515.0 mg/kg), malic acid (506.6 mg/kg), and fumaric acid (21.7 mg/kg). The three organic acids showed moderate nematicidal activities, but the mixture of citric acid, malic acid, and fumaric acid did not exhibit the full nematicidal activity of the culture filtrate of EML- DML3PNa1. Bioassay-guided fractionation coupled with 1H- and 13C-NMR and EI-MS analyses led to identification of kojic acid as the major nematicidal metabolite. Kojic acid exhibited dose-dependent mortality and inhibited the hatchability of M. incognita, showing EC50 values of 195.2 μg/ml and 238.3 μg/ml, respectively, at 72 h post-exposure. These results suggest that A. oryzae EML-DML3PNa1 and kojic acid have potential as a biological control agent against M. incognita.

Synthesis, Characterization and Biological Activities of 4-(p-Chlorophenyl)-1-(pyridin-2-yl)thiosemicarbazide and Its Metal Complexes

  • Hassanien, Mohammad M.;Mortada, Wael I.;Hassan, Ali M.;El-Asmy, Ahmed A.
    • Journal of the Korean Chemical Society
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    • v.56 no.6
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    • pp.679-691
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    • 2012
  • New series of metal complexes of Co(II), Ni(II), Cu(II), Zn(II), Pd(II) and Pt(II) with 4-(p-chlorophenyl)-1-(pyridin-2-yl)thiosemicarbazide (HCPTS) have been synthesized and characterized by elemental analyses, magnetic moment, spectra (IR, UV-Vis, $^1H$ NMR, mass and ESR) and thermal studies. The IR data suggest different coordination modes for HCPTS which behaves as a monobasic bidentate with all metal ions except Cu(II) and Zn(II) which acts as a monobasic tridentate. Based on the electronic and magnetic studies, Co(II), Cu(II), Pd(II) and Pt(II) complexes have square - planner, Ni(II) has mixed stereochemistry (tetrahedral + square planar), while Zn(II) is tetrahedral. Molar conductance in DMF solution indicates the non-ionic nature of the complexes. The ESR spectra of solid copper(II) complex show $g_{\parallel}$ (2.2221) > $g_{\perp}$ (2.0899) > 2.0023 indicating square-planar structure and the presence of the unpaired electron in the $d_x2_{-y}2$ orbital with significant covalent bond character. The thermal stability and degradation kinetics of the ligand and its metal complexes were studied by TGA and DTA and the kinetic parameters were calculated using Coats-Redfern and Horowitz-Metzger methods. The complexes have more antibacterial activity against some bacteria than the free ligand. However, the ligand has high anticancer activities against HCT116 (human colon carcinoma cell line) and HEPG2 (human liver hepatocellular carcinoma cell line) compared with its complexes.