• Title/Summary/Keyword: $^1H$ and $^{13}C$ NMR

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Biocompatibility of oxidized alginate/gelatin/BCP -based hydrogel composites

  • Phuong, Nguyen Thi;Min, Young-Ki;Yang, Hun-Mo;Song, Ho-Yeon;Lee, Byong-Teak
    • Proceedings of the Materials Research Society of Korea Conference
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    • 2010.05a
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    • pp.40.2-40.2
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    • 2010
  • In this study, oxidized alginate/gelatin/biphase calcium phosphate (BCP)- based hydrogel composites were fabricated. Alginate sodium was oxidized by periodate. The oxidized product was confirmed by using $^1H$ and $^{13}C$ NMR spectra. The number average molecular weight ($M_n$), the average molecular weight ($M_w$) of the oxidized alginate were determined by Gel Permeation Chromatography (GPC). The hydrogel was formed from the oxidized alginate and gelatin solution via Schift-base reaction. The hydrogel showed a highly porosity by a Scanning Electron Microscope (SEM) and Mercury Intrusion Porosimetry (MIP). Crosslinked density of the gel matrix were assessd by trinitrobenzene sulfonic acid (TNBS) assay that shows a high effect on swelling ratio. Increment of the crosslinked desity resulted in enhancing compressive strength of the hydrogel composite. The cytotoxity of hydrogel was assessed with osteoblast MG-63. The hydrogel composites show a high compatibility. The obtained results showed a potential application for bone regeneration in future.

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A Study of matrix metalloproteinase-9 inhibitor in root bark of ulmus davidiana planchon (유근피내의 Matrix Metalloproteinase-9 활성 억제제에 관한 연구)

  • Kong, Kwang-Hoon;Han, Kee-Jung;Lee, Kwang-Soo;Cho, Sung-Hye
    • Analytical Science and Technology
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    • v.18 no.2
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    • pp.104-111
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    • 2005
  • Several solvents were used to fractionate an extract obtained from the chapped root bark of Ulmus davidiana Planchon. The each fractionary part was condensed under reduced pressure and then examined to investigate the inhibitory effect on MMPs by modified gelatin zymography, where EA fraction showed the inhibition effect on the activity of MMPs. A compound showing inhibition effect on the MMPs was isolated and purified from EA fraction. Under IR, $^1H$- and $^{13}C$- NMR analyses it is very close to a catethin. This substance showed 48% inhibition effect on measurement of MMP-9 activity at 5 mM and 43% at 10 mM. To verify the effect of this substance on cells, human hepatoma, SK-Hep-1 cells as a cancer model, and Chang liver cells as a normal model were selected. MTT assay was performed to examine the cell viability by treatment of $1{\mu}L/mL$ of the purified substance on cells. The purified substance showed negligible toxicity on human liver cell line.

Trapping of Methylglyoxal by Sieboldin from Malus baccata L. and Identification of Sieboldin-Methylglyoxal Adducts Forms

  • Kim, Ji Hoon;Zhang, Kaixuan;Lee, Juhee;Gao, En Mei;Lee, Yun Jung;Son, Rak Ho;Syed, Ahmed Shah;Kim, Chul Young
    • Natural Product Sciences
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    • v.27 no.4
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    • pp.245-250
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    • 2021
  • The methylglyoxal (MGO) trapping constituents from Malus baccata L. were investigated using incubation of MGO and crude extract under physiological conditions followed by HPLC analysis. The peak areas of MGO trapping compounds decreased, and their chemical structures were identified by HPLC-ESI/MS. Sieboldin was identified as a major active molecule representing MGO-trapping activity of the crude extract. After reaction of sieboldin and MGO, remaining MGO was calculated by microplate assay method using imine (Schiff base) formation of 2,4-dinitrophenylhydrazine (DNPH) and aldehyde group. After 4 h incubation, sieboldin trapped over 43.8% MGO at a concentration of 0.33 mM and showed MGO scavenging activity with an RC50 value of 0.88 mM for the incubation of 30 min under physiological conditions. It was also confirmed that sieboldin inhibited the production of advanced glycation end products (AGE) produced by bovine serum albumins (BSA)/MGO. Additionally, MGO trapping mechanism of sieboldin was more specifically identified by 1H-, 13C-, 2D NMR and, confirm to be attached to the position of C-3' (or 5').

Identification of Phytotoxins Produced by Drechslera portulacae, a Pathogen of Purslane(Portulaca oleracea) - II. Isolation of Zeaenol and Its Herbicidal Activity (쇠비름(Porturaca oleracea)의 병원균, Drechslera portulacae가 생산하는 식물독소의 구조 동정 - 제 2 보. Zeaenol의 단리 및 제초활성)

  • Kim, K.W.
    • Korean Journal of Weed Science
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    • v.14 no.3
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    • pp.192-198
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    • 1994
  • Zeaenol isolated from the culture filtrate of a fungal weed pathogen Drechslera portulacae, which causes necrosis on the leaves and stem of purslane (Portulaca oleracea). Its structure was determined by single-crystal x-ray diffraction method together with assignments of $^1H$ and $^{13}C$-NMR experiments. Zeaenol inhibited root length of Echinochloa crus-galli and Abutilon avicennae by 22.8% and 54.8% at $3{\times}10^{-6}M$, respectively.

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Inclusion Complex of Analgesic and antiinflammatory Agents with Cyclodextrins (II) : Effect of $2-Hydroxypropyl-{\beta}-cyclodextrin$ on the Release of Ibuprofen Suppository (시클로덱스트린과 소염진통제간의 포접복합체에 관한 연구 (II) : 2-히드록시프로필-${\beta}$-시클로덱스트린이 이부프로펜 좌제의 방출에 미치는 영향)

  • Oh, In-Joon;Lee, Mi-Young;Lee, Yong-Bok;Shin, Sang-Chul
    • Journal of Pharmaceutical Investigation
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    • v.27 no.3
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    • pp.165-171
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    • 1997
  • Ibuprofen, a nonsteroidal antiinflammatory, analgesic and antipyretic drug, has several limitations in clinical application because of low solubility in water and gastrointestinal irritation. Effect of ibuprofen/$2-Hydroxypropyl-{\beta}-cyclodextrin\;(HP{\beta}CD)$ inclusion compound on release of suppository was investigated. Complex formation was confirmed by $^{1}H-\;and\;^{13}C-NMR$ spectroscopy. The release of ibuprofen from suppository base in vitro was significantly increased by the complexation with $HP{\beta}CD$. The release of ibuprofen from hydrophilic base was faster than that from hydrophobic base. In vivo studies, the release rate of ibuprofen from suppository was accelerated after rectal administration in complex form. This results suggested that ibuprofen/$HP{\beta}CD$ complex can be practically used for suppository to have faster effect of ibuprofen with reduced side effect.

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Sonochemical Synthesis of Closed [5,6]-bridged Aziridino[70]fullerene Derivative and Self-assembled Multilayer Films

  • Yoon, Shin-Sook;Hwang, Sung-Ho;Hong, Sung-Kyu;Lee, Jeong-Ho;Ko, Weon-Bae
    • Carbon letters
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    • v.10 no.4
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    • pp.325-328
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    • 2009
  • This cycloaddition of [70]fullerene with methyl azidoacetate in benzene under ultrasonic irradiated condition afforded the closed [5,6]-bridged aziridino[70]fullerene derivative, which was unusual product of cycloaddition to the 5,6-junction of fullerene. Its structure was determined by FAB-MS, UV-vis, $^1H-$ and $^{13}C$-NMR spectral data. The closed [5,6]-bridged aziridino[70]fullerene-functionalized gold nanoparticle films were self-assembled using the layer-by-layer method on the reactive of glass slides functionalized with 3-mercaptopropyl trimethoxysilane. The functionalized glass slides were alternately soaked in the solution containing closed the [5,6]-bridged aziridino[70]fullerene and 4-aminothiophenoxide/hexanethiolate-protected gold nanoparticles. The closed [5,6]-bridged aziridino[70]fullerene-functionalized gold nanoparticle films have grown up to 5 layers depending on the immersion time. The self-assembled nanoparticle multilayer films were characterized using UV-vis spectroscopy showed that the surface plasmon band of gold at 527 nm gradually became more evident as successive layers were added to the films.

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).

Quantitative Analysis of Luteolin 5-glucoside in Ajuga spectabilis and Their Neuroprotective Effects (자란초에서 분리된 Luteolin 5-glucoside의 함량분석과 신경세포 보호 활성)

  • Woo, Kyeong Wan;Sim, Mi Ok;Kim, A Hyun;Kang, Byoung Man;Jung, Ho Kyung;An, Byeongkwan;Cho, Jung Hee;Cho, Hyun Woo
    • Korean Journal of Pharmacognosy
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    • v.47 no.3
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    • pp.211-216
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    • 2016
  • In the course of our continuing search for biologically active components from Korean medicinal plants, we isolated the main compound, luteolin 5-glucoside from aqueous fraction of Ajuga spectabilis. The structure was elucidated by the basis of $^1H$ and $^{13}C$ NMR and TOF ESI-MS data. Quantitative analysis of luteolin 5-glucoside was carried out on a XBridge C18 column ($S-5{\mu}m$, $4.6{\times}250mm$) with gradient elution composed of acetonitrile:water. The results exhibit that the average content of main compound in A. spectabilis were 0.048%. Oxidative stress plays a major role Alzheimer's disease (AD) and other neurodogenerative disease. AD is major health problem and there is currently no clinically accepted treatment to cure or stop its progression. Pretreatment with luteolin 5-glucoside markedly attenuated $H_2O_2$-induced cell viability loss in a dose-dependent manner. Luteolin 5-glucoside also inhibited the formation of intracellular reactive oxygen species in SH-SY5Y. The results suggest that luteolin 5-glucoside from A. spectabilis has protective effects against oxidative stress-induced cytotoxicity, which might be a potential therapeutic compound for treating and/or preventing neurodegenerative disease implicated with oxidative stress.

Effect of Lignans from Schisandra chinensis Baillon on Seed Germination in Pepper (오미자 (Schisandra chinensis Baillon)로 부터 추출한 리그난이 고추종자의 발아에 미치는 영향)

  • Shin, Woo-Jung;Lee, You-Jin;Son, Beung-Gu;Kang, Jum-Soon;Lee, Yong-Jae;Park, Young-Hoon;Lee, Young-Geun;Kim, Yong-Cheol;Choi, In-Soo;Kim, Sun-Tae;Choi, Young-Whan
    • Journal of Life Science
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    • v.20 no.3
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    • pp.430-436
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    • 2010
  • In this study, the effects of dibenzocyclooctadiene on seed germination were investigated in pepper. Four $C_{18}$ dibenzocyclooctadiene lignans - schisandrin (1143.7 mg), schisandrin C (317.3 mg), gomisin A (261.4 mg) and gomisin N (213.4 mg) - were isolated from hexane extracts of the fruits of Schisandra chinensis. The molecular structures of the four lignans were elucidated based on spectroscopic analyses including 1D NMR experiments, and bi comparing their spectroscopic data with those of previous literatures. Seeds were immersed in $10^{-5}\;M$ schisandrin, $10^{-6}\;M$ schisandrin C and $10^{-7}\;M$ gomisin A and gomisin N for 1 hr and incubated at $25^{\circ}C$ in the dark for germination. Compared to untreated control, treatment with schisandrin C and gomisin A suppressed seed germination at 48 hrs after incubation, whereas treatment with gomisin N increased germination rate at 48 hrs after incubation. The results of the germination activity of the lignans from S. chinensis confirm their potential plant growth role, and the relative natural abundances of these metabolites suggest their potential use as natural plant growth regulators.

Phytochemical Analysis and Anti-cancer Investigation of Boswellia Serrata Bioactive Constituents In Vitro

  • Ahmed, Hanaa H;Abd-Rabou, Ahmed A;Hassan, Amal Z;Kotob, Soheir E
    • Asian Pacific Journal of Cancer Prevention
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    • v.16 no.16
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    • pp.7179-7188
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    • 2015
  • Cancer is a major health obstacle around the world, with hepatocellular carcinoma (HCC) and colorectal cancer (CRC) as major causes of morbidity and mortality. Nowadays, there isgrowing interest in the therapeutic use of natural products for HCC and CRC, owing to the anticancer activity of their bioactive constituents. Boswellia serrata oleo gum resin has long been used in Ayurvedic and traditional Chinese medicine to alleviate a variety of health problems such as inflammatory and arthritic diseases. The current study aimed to identify and explore the in vitro anticancer effect of B. Serrata bioactive constituents on HepG2 and HCT 116 cell lines. Phytochemical analysis of volatile oils of B. Serrata oleo gum resin was carried out using gas chromatography-mass spectrometry (GC/MS). Oleo-gum-resin of B. Serrata was then successively extracted with petroleum ether (extract 1) and methanol (extract 2). Gas-liquid chromatography (GLC) analysis of the lipoidal matter was also performed. In addition, a methanol extract of B. Serrata oleo gum resin was phytochemically studied using column chromatography (CC) and thin layer chromatography (TLC) to obtain four fractions (I, II, III and IV). Sephadex columns were used to isolate ${\beta}$-boswellic acid and identification of the pure compound was done using UV, mass spectra, $^1H$ NMR and $^{13}C$ NMR analysis. Total extracts, fractions and volatile oils of B. Serrata oleo-gum resin were subsequently applied to HCC cells (HepG2 cell line) and CRC cells (HCT 116 cell line) to assess their cytotoxic effects. GLC analysis of the lipoidal matter resulted in identification of tricosane (75.32%) as a major compound with the presence of cholesterol, stigmasterol and ${\beta}$-sitosterol. Twenty two fatty acids were identified of which saturated fatty acids represented 25.6% and unsaturated fatty acids 74.4% of the total saponifiable fraction. GC/MS analysis of three chromatographic fractions (I,II and III) of B. Serrata oleo gum resin revealed the presence of pent-2-ene-1,4-dione, 2-methyl- levulinic acid methyl ester, 3,5- dimethyl- 1-hexane, methyl-1-methylpentadecanoate, 1,1- dimethoxy cyclohexane, 1-methoxy-4-(1-propenyl)benzene and 17a-hydroxy-17a-cyano, preg-4-en-3-one. GC/MS analysis of volatile oils of B. Serrata oleo gum resin revealed the presence of sabinene (19.11%), terpinen-4-ol (14.64%) and terpinyl acetate (13.01%) as major constituents. The anti-cancer effect of two extracts (1 and 2) and four fractions (I, II, III and IV) as well as volatile oils of B. Serrata oleo gum resin on HepG2 and HCT 116 cell lines was investigated using SRB assay. Regarding HepG2 cell line, extracts 1 and 2 elicited the most pronounced cytotoxic activity with $IC_{50}$ values equal 1.58 and $5.82{\mu}g/mL$ at 48 h, respectively which were comparable to doxorubicin with an $IC_{50}$ equal $4.68{\mu}g/mL$ at 48 h. With respect to HCT 116 cells, extracts 1 and 2 exhibited the most obvious cytotoxic effect; with $IC_{50}$ values equal 0.12 and $6.59{\mu}g/mL$ at 48 h, respectively which were comparable to 5-fluorouracil with an $IC_{50}$ equal $3.43{\mu}g/mL$ at 48 h. In conclusion, total extracts, fractions and volatile oils of B. Serrata oleo gum resin proved their usefulness as cytotoxic mediators against HepG2 and HCT 116 cell lines with different potentiality (extracts > fractions > volatile oil). In the two studied cell lines the cytotoxic acivity of each of extract 1 and 2 was comparable to doxorubicin and 5-fluorouracil, respectively. Extensive in vivo research is warranted to explore the precise molecular mechanisms of these bioactive natural products in cytotoxicity against HCC and CRC cells.