• Title/Summary/Keyword: $^{13}C$-NMR

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($n^5$-Indenyl)trichlorotitanium-catalyzed Copolymerization of Styrene and Styrenic Macromonomer Carrying a Functional Group

  • Kim, Jungahn;Kim, Keon-Hyeong;Jin, Yong-Hyeon;Hyensoo Ryu;Soonjong Kwak;Kim, Kwang-Ung;Hwang, Sung-Sang;Jo, Won-Ho;Jho, Jae-Young
    • Macromolecular Research
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    • v.8 no.1
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    • pp.44-52
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    • 2000
  • Styrenic macromonomers with/without a silyloxy-functional group were synthesizedvia chain-end functionalization using 4-vinylbenzyl chloride as a terminating agent insec-butyllithium-initiated polymerization of styrene. The yields were 92 mol% for the silyloxy group and 88 mol% for the styrenic unit. Crystalline polystyrene-g-amorphous polystyrenes were synthesized by (η$^{5}$ -indenyl)-trichlorotitanium ((Ind)TiCl$_3$)-catalyzed copolymerizations of the macromonomers with styrene in the presence of methyl-aluminoxane (MAO) in toluene at 4$0^{\circ}C$. The macromonomer having $\alpha$, $\alpha$'-bis (4-[tert-butyldimethylsilyl-oxy]phenyl) group was also utilized for the preparation of a precursor of hydroxyl-functionalized syndio-tactic polystyrene. The obtained polymers were characterized by a combination of$^1$H, $^{13}$ C NMR spectroscopic, size exclusion chromatographic, and differential scanning calorimetric analysis. The (Ind)TiCl$_3$-catalyzed copolymerization of styrene with the macromonomer carrying the silyloxy functional group was found to be an efficient method to modify syndiotactic polystyrene without a great loss of physica] property by controlling the feud ratio of the macromonomer.

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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).

Integracide K: A New Tetracyclic Triterpenoid from Desmodium uncinatum (Jacq.) DC. (Fabaceae)

  • Tsafack, Borice Tapondjou;Ponou, Beaudelaire Kemvoufo;Teponno, Remy Bertrand;Nono, Raymond Ngansop;Jenett-Siems, Kristina;Melzig, Matthias F.;Park, Hee Juhn;Tapondjou, Leon Azefack
    • Natural Product Sciences
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    • v.23 no.2
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    • pp.113-118
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    • 2017
  • A new tetracyclic triterpenoid [4,4,24-trimethylcholesta-${\Delta}^{8,9;14,5;24,28}$-trien-$3{\beta},11{\beta},12{\alpha}$-triol-12-acetate, 3-sulfate] sodium salt (1), together with eight known compounds including ergosterol $5{\alpha},8{\alpha}$-endoperoxide (2), 1,9-dihydroxy-3-methoxy-2-methylpterocarpan (3), 3-O-${\beta}$-D-2-acetyl-amino-2-deoxyglucopyranoxyloleanoic acid (4), hydnocarpin (5), derrone (6), isovitexin (7), erythrinin C (8), and 5,4'-dihydroxy-2"-hydroxyisopropyldihydrofurano [4,5:7,8]-isoflavone (9), were isolated from the EtOAc soluble fraction of the methanol extract of aerial part of Desmodium uncinatum collected in the western highland of Cameroon. The structures of these compounds were established by comprehensive interpretation of their spectral data mainly including 1D- ($^1H$ and $^{13}C$), 2D-NMR($^1H$-$^1H$ COSY, HMQC, HMBC) spectroscopic and ESI-TOF-MS mass spectrometric analysis. The isolation of an integracide-like compound from plant origin is a very unusual finding.

Antioxidant Constituents from the Leaves of Cedrela sinensis A. Juss

  • Lee, Ik-Soo;Wei, Chun-Hua;Thoung, Phuong Thien;Song, Kyung-Sik;Seong, Yeon-Hee;Bae, Ki-Hwan
    • Korean Journal of Medicinal Crop Science
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    • v.14 no.5
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    • pp.267-272
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    • 2006
  • Phytochemical study on the EtOAc fraction from the MeOH extract of the leaves of Cedrela sinensis led to the isolation of five known phenolic compounds (1-5), whose structures were identified as (+)-catechin (1), $kaempferol-3-0-{\alpha}- L-rhamnopyranoside$ (2), quercetin (3), $quercetin-3-O-{\alpha}-L-rhamnopyranoside$ (4), and $quercetin-3-O-{\beta}-D-glucopyranoside$ (5), respectively, by comparing their spectral $(uv,\;JR,\;IH\;and\;^{13}C-NMR,\;and\;ESI-MS)$ and physicochemical data with those reported in the literature. Among the isolated compounds (1-5), compounds 1 and 3-5 exhibited significant DPPH radical scavenging effects with $IC{_50}$ values ranging from $21.3{\pm}1.4\;to\;38.1{\pm}3.2 {\mu}M$ as well as superoxide anion radical scavenging effects with $IC{_50}$ values ranging from $9.4{\pm}0.7\;to\;21.2{\pm}3.6 {\mu}M$. Furthermore, compounds 1 and 3-5 also exhibited considerable inhibitory effects on LDL peroxidation induced by either $CU^{2+}$ or AAPH with $IC{_50}$ values ranging from $1.4{\pm}0.4\;to\;11.9{\pm}1.4\;{\mu}M$. These results indicated that flavonoids are the major constituents of C. sinensis and considered to be antioxidant principles of this plant.

Production of Oleamide, a Functional Lipid, by Streptomyces sp. KK90378

  • Kwon, Jeong-Ho;Hwang, Sung-Eun;Han, Jae-Taek;Kim, Chang-Jin;Rho, Jung-Rae;Shin, Jong-Eon
    • Journal of Microbiology and Biotechnology
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    • v.11 no.6
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    • pp.1018-1023
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    • 2001
  • Oleamide (cis-9-octadecenamide) is endogenous primary amide of fatty acid that is produced in small amounts in animal brains. It is known to induce sleep and to lower temperature by destroying the lipid plasma membrane structure of cells, thereby disclosing gap junction channels. To develop a new biological production method for oleamide, a screening program was conducted to isolate a microorganism producing oleamide. Among 1,500 soil microorganisms tested, KK90378 exhibited a potent positive reaction with Dragendoff`s reagent, used to detect the primary amide of oleamide. KK90378 was identified as a Streptomyces species based on cultural and morpohological characteristics, the presence of diaminopimelic acid in the cell wall, and the sugar patterns for the whole-cell extrat. Streptomyces sp. KK90378 produced oleamide 3 days after culture at $28^{\circ}C$, pH 7.2 A series of purification steps, including hexane extraction, silica gel column, and preparative thin layer chromatographies, were performed for the purification of oleamide. A spectrophotometric analysis using $^1H$, $^13C$-NMR, and GC-MS confirmed that the chemical structure of the purified oleamide was identical to that of authentic oleamide.

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Synthesis of Biosurfactant-Based Silver Nanoparticles with Purified Rhamnolipids Isolated from Pseudomonas aeruginosa BS-161R

  • Kumar, C. Ganesh;Mamidyala, Suman Kumar;Das, Biswanath;Sridhar, B.;Devi, G. Sarala;Karuna, Mallampalli SriLakshmi
    • Journal of Microbiology and Biotechnology
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    • v.20 no.7
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    • pp.1061-1068
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    • 2010
  • The biological synthesis of nanoparticles has gained considerable attention in view of their excellent biocompatibility and low toxicity. We isolated and purified rhamnolipids from Pseudomonas aeruginosa strain BS-161R, and these purified rhamnolipids were used to synthesize silver nanoparticles. The purified rhamnolipids were further characterized and the structure was elucidated based on one- and two-dimensional $^1H$ and $^{13}C$ NMR, FT-IR, and HR-MS spectral data. Purified rhamnolipids in a pseudoternary system of n-heptane and water system along with n-butanol as a cosurfactant were added to the aqueous solutions of silver nitrate and sodium borohydride to form reverse micelles. When these micelles were mixed, they resulted in the rapid formation of silver nanoparticles. The synthesized nanoparticles were characterized by UV-Visible spectroscopy, transmission electron microscopy, and energy dispersive X-ray spectroscopy (EDS). The nanoparticles formed had a sharp adsorption peak at 410 nm, which is characteristic of surface plasmon resonance of the silver nanoparticles. The nanoparticles were monodispersed, with an average particle size of 15.1 nm (${\sigma}={\pm}5.82$ nm), and spherical in shape. The EDS analysis revealed the presence of elemental silver signal in the synthesized nanoparticles. The formed silver nanoparticles exhibited good antibiotic activity against both Grampositive and Gram-negative pathogens and Candida albicans, suggesting their broad-spectrum antimicrobial activity.

Isolation and Identification of Inhibitory Compounds on Helicobacter pylori from Rosa multiflora Thunberg Fruit Extracts (Rosa multiflora Thunberg fruit 추출물로부터 Helicobacter pylori 억제물질의 분리 및 동정)

  • Park, Ki-Tae;Kim, Jin-Sung;Jo, Bun-Sung;An, Bong-Jeun;Chun, Sung-Sook;Kim, Jeung-Hoan;Cho, Young-Je
    • Journal of Life Science
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    • v.20 no.10
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    • pp.1511-1518
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    • 2010
  • The antimicrobial activity of 70% ethanol extracts from Rosa multiflora Thunberg fruit against Helicobacter pylori was examined. The inhibitory activity of Rosa multiflora Thunberg fruit extracts against H. pylori was determined to clear a zone of 14 mm with 70% ethanol extracts. Purification of inhibitory compounds was carried on Sephadex LH-20 and $C_{18}$ cartridge column chromatography using a gradient procedure, with increasing ethanol ($0{\rightarrow}100%$) in $H_2O$. The chemical structure of the purified inhibitory compounds on H. pylori was identified to be protocatechuic acid, chlorogenic acid and quercetin by FAB-MS, NMR and IR spectrum.

[${\gamma}-Mangostin$ and Rubraxanthone, Two Potential Lead Compounds for Anti-cancer Activity against CEM-SS Cell Line

  • Ee, G.C.L.;Izzaddin, S.A.;Rahmani, M.;Sukari, M.A.;Lee, H.L.
    • Natural Product Sciences
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    • v.12 no.3
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    • pp.138-143
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    • 2006
  • Our continuing interest on Garcinia and Mesua species has led us to carry out a detail study on the chemistry of the root bark of Garcinia mangostana (Guttiferae) since this part of the plant has not been investigated before, and the strm bark of Mesua corneri (Guttiferae) an uninvestigated species. This study has yielded six xanthones, ${\alpha}-mangostin$ (1), ${\beta}-mangostin$ (2), ${\gamma}-mangostin$ (3), garcinone-D (4), mangostanol (5) and gartanin (6) from Garcinia mangostana and two xanthones rubraxanthone (7) and inophyllin B (8) from Mesua corneri. Structural elucidations were achieved using $^1H,\;^{13}C$ NMR and MS data. The crude hexane and chloroform extracts of the root bark of Garcinia mangostana and the hexane extract of the stem bark of Mesua corneri were found to be active against CEM-SS cell lines with $IC_{50}$ values less than $30\;{mu}g/ml$. Moreover, ${\gamma}-mangostin$ gave a very low $LC_{50}$ value of $4.7\;{mu}g/ml$ while rubraxanthone gave an $LC_{50}$ value of $5.0\;{mu}g/ml$ indicating these two compounds to be potential lead compounds for anti-cancer activity against the CEM-SS cell line. This paper reports the isolation and identification of these compounds as well as bioassay data for the crude extracts, ${\gamma}-mangostin$ and rubraxanthone.

Adenosine derived from Staphylococcus aureus-engulfed macrophages functions as a potent stimulant for the induction of inflammatory cytokines in mast cells

  • Ma, Ying Jie;Kim, Chan-Hee;Ryu, Kyoung-Hwa;Kim, Min-Su;So, Young-In;Lee, Kong-Joo;Garred, Peter;Lee, Bok-Luel
    • BMB Reports
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    • v.44 no.5
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    • pp.335-340
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    • 2011
  • In this study, we attempted to isolate novel mast cell-stimulating molecules from Staphylococcus aureus. Water-soluble extract of S. aureus cell lysate strongly induced human interleukin-8 in human mast cell line-1 and mouse interleukin-6 in mouse bone marrow-derived mast cells. The active molecule was purified to homogeneity through a $C_{18}$ reverse phase HPLC column. By determination of its structure by MALDITOF and $^1H$- and $^{13}C$-NMR, adenosine was revealed to be responsible for the observed cytokine induction activities. Further studies using 8-sulfophenyl theophylline, a selective adenosine receptor blocker, verified that purified adenosine can induce interleukin-8 production via adenosine receptors on mast cells. Moreover, adenosine was purified from S. aureus-engulfed RAW264.7 cells, a murine macrophage cell line, used to induce phagocytosis of S. aureus. These results show a novel view of the source of exogenous adenosine in vivo and provide a mechanistic link between inflammatory disease and bacterial infection.

The Changes of Capsaicin Contents in Fresh and Processed Red Peppers (생고추와 고추 가공시의 Capsaicin 함량 변화)

  • Chung, Byung-Sun;Kang, Kun-Og
    • Journal of the Korean Society of Food Science and Nutrition
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    • v.14 no.4
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    • pp.409-418
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    • 1985
  • The contents of capicin according to the growth of fresh red peppers (Capsicum annum) and to-brewing of 'kochujang' (fermented hot peper-soybean paste) and 'kimchi' (a group of Korean seasoned pickles) were quantified by High Pressure Liquid Chromatography. Colors of the peppers were evaluated by Hunter Value and quantity of capsanthin. The content and chemical structure of capsaicin after heat treatment were traced by HPLC, GCMS, UV and NMR. It was found that the capsaicin content of red peper was highest 6 to 7 weeks after flowering and that peppers with high Hunter Value contained higher level of capsanthin. The content of capsaicin of kochujang and kimchi declined by 20% and 17% respectively, as they are brewed. Capsaicin content was decreased by heating. However, change in its chemical strtcure was not occurred.

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