• Title/Summary/Keyword: NMR study

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The Cytotoxic Limonoid From the Fruits of Melia Toosendan (천련자로부터 분리한 Limonoid 성분의 세포독성)

  • Km, Young-Ho;Hwang, Bang-Yeon;Kim, Se-Eun;Kim, Hwan-Mook;Oh, Goo-Taeg;Ro, Jai-Seup;Lee, Kyong-Soon;Lee, Jung-Joon
    • YAKHAK HOEJI
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    • v.38 no.1
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    • pp.6-11
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    • 1994
  • The MeOH extract of the fruits of Melia toosendan was selected for futher study by its cytotoxicity and effect on the human breast cancer cell line, MCF-7. The active principle obtained by activity guided fractionation followed by purification gave rise to a needle crystal. The structure was deduced by employing NMR and was determined to be identical with 28-deacetyl sendanin by comparison with published data. This compound induced morphological change of MCF-7 to be rounded with tubule at concentrations between $50\;{\mu}g/ml$ and $0.025\;{\mu}g/ml$. This compound, however, showed strong cytotoxic effect on Hepalclc7 and HepG2, and their $GI_{50}$ on the hepatoma cell lines were $0.238\;{\mu}g/ml$ and $0.805\;{\mu}g/ml$, respectively. Its effect on lymphocyte of mouse was stronger than hepatoma cell lines, and their $ED_{50}$ of polyclonal antibody response was $0.011\;{\mu}g/ml$, and $ED_{50}$ of cell viability was $0.039\;{\mu}g/ml$.

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Inhibition of Matrix Metalloproteinase-2 Activity of Flavonol Glycosides from Cedreia sinensis (참죽나무에서 분리한 flavonol glycoside의 금속단백분해효소-2 억제 활성)

  • Hwang Seon-Woo;Ha Tae-Joung;Kho Yung-Hee;Chun Hyo-Kon;Lee Jun;Kwon Hyun-Sook;Park Ki-Hun;Yang Min-Suk
    • Journal of Life Science
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    • v.16 no.3 s.76
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    • pp.442-446
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    • 2006
  • Cedrela sinensis is a broadleaf tree that is widely cultivated in Korea and China. It was used for treating enteritis, dysentery, and skin itch in oriental medicine. In this study, three major flavonoids, kaempferol-3-O-rhamnoside (1), quercetin-3-O-rhamnoside (2), and quercetin-3-O-glucoside (3), were isolated from the leaf of Cedrela sinensis. The biological activities of these compounds were tested by inhibitory activity of matrix metalloproteinases-2 (Type IV collagenase) method together with a cytotoxicity and a apoptosis test against human cancer cell lines.

Microwave Assisted Extraction of Physiologically Active Materials from Agaricus blazei Fruiting Bodies (Agaricus blazei 자실체로부터 마이크로웨이브를 이용한 생리활성물질 추출공정)

  • 최정우;류동열;홍억기;권명상;한진수;이원홍
    • KSBB Journal
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    • v.15 no.3
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    • pp.307-312
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    • 2000
  • Physiologically active material ${\beta}$-glucan extracted from mushroom has an antitumor effect. Agaricus blazei murill(A blazel) fruiting bodies were reported to contain large amounts of ${\beta}$-glucan. The purpose of this study was to maximize ${\beta}$-glucn extraction from A. blazei by microwave assisted extraction method. Optimal extraction conditions were obtained under various extraction time and applied power which was examined as 200, 500 and 650 watt. The structure and concentrations of the raffinates were analyzed by nuclear magnetic resonance spectroscopy(NMR) and infrared spectroscopy(IR) It was proved that the extraction yield of microwave assisted extraction method was higher than that of conventional solvent extraction method. It was also observed that microwave assisted extraction method requires less amounts of solvents and extraction time compared to the conventional solvent extraction method.

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Ligand Binding Properties of the N-Terminal Domain of Riboflavin Synthase from Escherichia coli

  • Lee, Chan-Yong;Illarionov, Boris;Woo, Young-Eun;Kemter, Kristina;Kim, Ryu-Ryun;Eberhardt, Sabine;Cushman, Mark;Eisenreich, Wolfgang;Fischer, Markus;Bacher, Adelbert
    • BMB Reports
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    • v.40 no.2
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    • pp.239-246
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    • 2007
  • Riboflavin synthase from Escherichia coli is a homotrimer of 23.4 kDa subunits and catalyzes the formation of one molecule each of riboflavin and 5-amino-6-ribitylamino- 2,4(1H,3H)-pyrimidinedione by the transfer of a 4-carbon moiety between two molecules of the substrate, 6,7- dimethyl-8-ribityllumazine. Each subunit comprises two closely similar folding domains. Recombinant expression of the N-terminal domain is known to provide a $C_2$-symmetric homodimer. In this study, the binding properties of wild type as well as two mutated proteins of N-terminal domain of riboflavin synthase with various ligands were tested. The replacement of the amino acid residue A43, located in the second shell of riboflavin synthase active center, in the recombinant N-terminal domain dimer reduces the affinity for 6,7-dimethyl-8-ribityllumazine. The mutation of the amino acid residue C48 forming part of activity cavity of the enzyme causes significant $^{19}F$ NMR chemical shift modulation of trifluoromethyl derivatives of 6,7-dimethyl-8-ribityllumazine in complex with the protein, while substitution of A43 results in smaller chemical shift changes.

Structure Determination of Macrolactin Compounds with Antibacterial Activities Isolated from Bacillus polyfermenticus KJS-2 (Bacillus polyfermenticus KJS-2에서 분리된 항생물질 마크로락틴류의 구조결정)

  • Kim, Dong-Hee;Kang, Kyung-Ran;Kim, Hyun-Woo;Yoon, Si-Yeol;Kim, Chun-Gyu;Yamaguchi, Tokutaro;Sohng, Jae-Kyung;Kang, Jae-Seon
    • Journal of Life Science
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    • v.20 no.12
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    • pp.1792-1800
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    • 2010
  • In this study, we isolated five macrolactin compounds from a fermentation broth of Bacillus polyfermenticus KJS-2. The macrolactin compounds were structurally identified as macrolactin A (MA), 7-O-malonyl macrolactin A (MMA), 7-O-succinyl macrolactin A (SMA), macrolactin E (ME) and macrolactin F (MF) via a variety of NMR techniques, COZY, DEPT, HMQC and HMBC, and mass and specific rotation assays. The three macrolactin compounds, MA, MMA and SMA, profoundly inhibited the growth of both vancomycin-resistant Enterococci (VREs) and methicillin-resistant Staphylococcus aureus (MRSA), the inhibition of which were estimated via a disc agar diffusion bioassay. MA, MMA, and SMA exhibited antibacterial activities superior to those of vancomycin and teicoplanin.

Analysis of Dyeing Components from Neolitsea sericea Koidz Bark (참식나무(Neolitsea sericea Koidz) 수피의 염착물질 분석)

  • Lee, Sang-Kueg;Jo, Hyun-Jin;Kim, Yun-Geun;Lee, Hak-Ju;Kang, Ha-Young
    • Journal of the Korean Wood Science and Technology
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    • v.34 no.3
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    • pp.64-72
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    • 2006
  • Two compounds were isolated from the diethylether and ethyl acetate fraction of hot water extracts by TLC and column chromatography as dyeing components. The isolated compounds were characterized as H-dibenzoquinoline-2,10-diol,5,6,6a,7-tetrahydro-1,9-dimethoxy-6-methyl (compoundI) and lyoniresinol (compoundII) by NMR and Mass spectrophotometry. To investigate if the isolated compounds are involved in the dyeing process, HPLC analysis was used. The retention time of the components from dye used in the study and the dye decolorized from the dyed substrate, silk by ethyl acetate were compared to conform the identity of those compounds. The retention time of the components from the dye and decolorized solution were identical. As a results, those two compounds were considered as dye bound to the silk.

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.

Bioconversion Constituents of Galgeun-tang Fermented by Lactobacillus plantarum (Lactobacillus plantarum 발효에 의한 갈근탕의 생물 전환 성분 연구)

  • Yang, Min-Cheol;Kim, Dong-Seon;Jeong, Sang-Won;Ma, Jin-Yeul
    • Korean Journal of Medicinal Crop Science
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    • v.19 no.6
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    • pp.446-455
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    • 2011
  • Galgeun-tang (GGT) is a traditional medicinal formula that is widely prescribed to treat cold, asthma, and hives in Korea. Fermented herbal medicines can be made more effective than normal herbal medicines by increasing the absorption and bioavailability of the active compounds. In this study, we fermented Galgeun-tang to produce bioconversion constituents using Lactobacillus plantarum (GGT144), and found that four peaks were decreased, three peaks were increased and two new peaks appeared in the HPLC-DAD chromatogram. After HPLC-DAD-guided fractionation of the newly-appearing compounds (1 and 5) and the increased (6, 7, and 9) compounds, the structure of the compounds was determined using NMR and MS. Using this approach the compounds were identified to be pyrogallol (1), daidzein (5), liquiritigenin (6), cinnamyl alcohol (7), and formononetin (9), respectively. In addition, the decreased compounds were identified to be daidzin (2), liquiritin (3), ononin (4), and cinnam aldehyde (8) using HPLC-DAD analysis with standard compounds. The high performance liquid chromatography method was used to quantify the nine constituents in GGT and GGT144. All calibration curves of the standard compounds displayed excellent linearity with a $R^2$ > 0.9968.

Synthesis of Modified Polyester Containing Phosphorus and Chlorine for Flame-Retardant Coatings (난연도료용 인과 염소 함유 변성폴리에스테르의 합성)

  • Park, Hong-Soo;Shim, Il-Woo;Jo, Hye-Jin;You, Hyuk-Jae;Kim, Yeoung-Chan
    • Journal of the Korean Applied Science and Technology
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    • v.22 no.3
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    • pp.257-269
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    • 2005
  • This study was focused on the maximization of flame-retardancy of polyesters by a synergism of simultaneously introduced chlorine and phosphorus into polymer chains of modified polyesters. To prepare modified polyesters, reaction intermediates, TD-adduct (prepared from trimethylolpropane /2,4-dichlorobenzoic acid (2,4-DCBA)) and TMBO (prepared from tetramethlene bis (orthophosphate)), were prepared first, then condensation polymerization of the prepared intermediates, adipic acid, and 1,4-butanediol were carried out. In the condensation polymerization, the content of phosphorus was fixed to be 2wt%, and the content of 2,4-DCBA that provides chlorine component was varied to be 10, 20, and 30wt%, and we designated the prepared modified polyesters containing chlorine and phosphorus as ABTTs. The prepared intermediates and modified polyesters were characterized with FT-IR, NMR, GPC, and TGA analysis. Average molecular weight and polydipersity index of the preparation of ABTTs were decreased with increasing 2,4-DCBA content because of the incease in hydroxyl group that retards reaction. We found that the thermal stability of the prepared ABTTs increased with chlorine content at high temperatures.

Evaluation of Hydration Effect on Human Skin by $^1H$ MRS at 14.1T

  • Choi Chi-Bong;Hong Sung-Tak;Choe Bo-Young;Woo Dong-Chul;Yoon Seong-Ik;Cho Ji-Hyun;Lee Chul-Hyun;Cheong Chae-Joon;Park Sang-Yong;Oh Chil-Hwan
    • Journal of the Korean Magnetic Resonance Society
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    • v.10 no.1
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    • pp.105-114
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    • 2006
  • Purpose: We achieved high resolution MR imaging and spectra of human skin in vitro with using a 14.1 T MRI/MRS system, and evaluated the hydration effect of various cosmetic products by measuring the skin's. moisture concentration. Materials and Methods: We used the Bruker 14.1 T MRI/MRS system with a vertical standard bore that was equipped with a DMX spectrometer gradient system (200 G/cm at a maximum 40 A), RF resonators (2, 5 and 10 mm) and Para Vision software. Spin echo and fast spin echo pulse sequences were employed for obtaining the high resolution MR images. The 3D-localized point resolved spectroscopy (PRESS) method was used to acquire the MR spectra. Results: The high resolution MR images and spectra of human skin in vitro were successfully obtained on a 14.1 T system. The water concentration of human skin after applying a moisturizer was higher than that before applying a moisturizer. Conclusions: The present study demonstrated that the high-resolution MR images and spectra of human skin from a high field NMR instrument could be applicable to evaluating the hydration state of the stratum corneum.

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