• Title/Summary/Keyword: NMR spectral analysis

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Five New Stilbenes from the Stem Bark of Artocarpus communis

  • Chan, Susanna T.S.;Popplewell, Wendy L.;Bokesch, Heidi R.;McKee, Tawnya C.;Gustafson, Kirk R.
    • Natural Product Sciences
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    • v.24 no.4
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    • pp.266-271
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    • 2018
  • Five new prenylated stilbenes (1 - 5), along with the known compounds cudraflavone C, trans-4-isopentenyl-3,5,2',4'-terahydroxystilbene, trans-4-(3-methyl-E-but-1-enyl)-3,5,2',4'-tetrahydroxystilbene, pannokin G, cycloartobiloxanthone, artonin P, morusin, artocarpin, artonin E, kuwanon C, artobiloxanthone, and artoindonesianin C (6 - 17) were isolated from the stem bark of the tropical tree Artocarpus communis. The structures were established by NMR spectroscopic analysis, MS studies, and comparison with spectral data reported in the literature.

A Cipadesin Limonoid and a Tirucallane Triterpene from the Fruit of Sandoricum koetjape and their Inhibitory Properties against Receptor Tyrosine Kinases

  • Rachmadhaningtiyas, Dyah Ayu;Heliawati, Leny;Hermawati, Elvira;Syah, Yana Maolana
    • Natural Product Sciences
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    • v.27 no.2
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    • pp.134-139
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    • 2021
  • A new cipadesin limonoid, i.e. 3-epi-cipadonoid C (1), and a new tirucallane triterpene, i.e. hispidol B 3-palmitate (3), have been isolated from the seeds and fruit peels extract of Sandoricum koetjape, respectively. Along with these compounds the known limonoid, cipaferen G (2), and two pentacyclic triterpenes, bryonolic (4) and bryononic (5) acids, were also isolated. The strucrures of the new compounds were elucidated by the analysis of NMR and mass spectral data. Compounds 1 - 5 were evaluated as the inhibitor of receptor tyrosine kinases (EGFR, Epidermal Growth Factor Receptor; HER2, HER4, Human Epidermal growth factor Receptor 2, -4; IGFR, Insulin-like Growth Factor Receptor; InsR, Insulin Receptor; KDR, Kinase insert Domain Receptor; PDGFRα, and PDGFRβ, Platelet-Derived Growth Factor Receptor-α and -β). The results showed only 1 and 3 that have weak activity against InsR.

Synthesis and Characterization of UO2(VI), Th(IV), ZrO(IV) and VO(IV) Complexes with Schiff-Base Octaazamacrocyclic Ligands (Schiff-염기인 옥타아자-거대고리 리간드의 UO2(VI), Th(IV), ZrO(IV) 및 VO(IV) 착물 합성 및 특성)

  • Mohapatra, Ranjan Kumar;Dash, Dhruba Charan
    • Journal of the Korean Chemical Society
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    • v.54 no.4
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    • pp.395-401
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    • 2010
  • A series of macrocyclic complexes of the type [M(L/L')$(NO_3)_n$].$mH_2O$ and [VO(L/L')($SO_4$)].$2H_2O$, where L/L' is a Schiff base "3,4,10,11-tetraphenyl/tetramethyl-1,2,5,6,8,9,12,13-octaaza cyclotetradeca-2,4,9,11-tetraene-7,14-dithione" derived from thiocarbohydrazide (TCH), benzilmonohydrazone (BMH)/diacetylmonohydrazone (DMH) and carbon disulphide, M = $UO_2$ (VI), Th(IV) and ZrO(IV), n = 2, 4, m = 2, 3, have been synthesized via metal ion template methods. The complexes are characterized on the basis of elemental analysis, thermal analysis, molar conductivity, magnetic moment, electronic, infrared and $^1H$-NMR spectral studies. The ESR and cyclic voltammetry studies of the vanadyl complexes have been carried out. The results indicate that the VO(IV) ion is penta-coordinated yielding paramagnetic complexes; $UO_2$(VI) and ZrO(IV) ions are hexacoordinated where as Th(IV) ion is octa-coordinated yielding diamagnetic complexes of above composition.

Isolation and Purification of Berberine in Cortex Phellodendri by Centrifugal Partition Chromatography (Centrifugal Partition Chromatography에 의한 황백으로부터 Berberine의 분리 및 정제)

  • Kim, Jung-Bae;Bang, Byung-Ho
    • The Korean Journal of Food And Nutrition
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    • v.27 no.3
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    • pp.532-537
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    • 2014
  • Cortex Phellodendri (CP) is derived from the dried bark of Phellodendron amurense. It has been widely used as a drug in traditional Korea medicine for treating diarrhea, jaundice, swelling pains in the knees and feet, urinary tract infections, and infections of the body surface. Many analytical methods have been used to study oriental herbal medicines, such as thin-layer chromatography, column liquid chromatography, and high performance liquid chromatography (HPLC). In this study, preparative centrifugal partition chromatography (CPC) was successfully carried out in order to separate pure compounds from a CP methanol extract. The optimum two-phase CPC solvent system was composed of n-butanol: acetic acid: water (4:1:5 v/v/v). The flow rate of the mobile phase was 3 mL/min in ascending mode with rotation at 1,000 rpm. The CPC-separated fraction and purification procedures were carried out by preparatory HPLC. The $^1H$ NMR spectrum revealed that the resonances at ${\delta}$ 4.10 and 4.20 ppm corresponded to three protons ($-OCH_3$), whereas those at ${\delta}$ 6.10 ppm corresponded to two protons ($-OCH_2O-$). Further, two aromatic protons (H-11 and H-12) conveys a doublet-doublet pattern. The H-11 doublet and H-12 doublet appear at ${\delta}$ 7.98 and 8.11, respectively. The $^{13}C$ NMR. spectrum showed a tetrasubstituted with a methylenedioxy group at C2 and C3, and two methoxy groups at C9 and C10. The chemical structure of the berberine was identified by $^1H$, $^{13}C$-nuclear magnetic resonance and electrospray ionization-mass spectroscopy spectral data analysis.

Isolation and Characterization of Humic Acids Present in the Soils at the Vicinity of Domestic Atomic Power Plants(NPPs) (국내 원자력 발전소 주변 토양 휴믹산의 추출 및 특성 규명)

  • Lee, Chang-Hoon;Shin, Hyun-Sang;Chung, Kun-Ho;Cho, Young-Hyun;Lee, Chang-Woo
    • Journal of Radiation Protection and Research
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    • v.28 no.3
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    • pp.165-172
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    • 2003
  • Humic acids present in the soils at the vicinity of domestic atomic power plants(NPPs), located in Yeongkwang(YK), Uljin(UJ), Kori(KR), Koseong(KS), Wolseong(WS) area were isolated, and characterized using elemental analysis and UV/Vis, IR, CPMAS $^{13}C$ NMR spectroscopic methods. The characteristics were compared with one another and with commercial humic acid (Aldrich Co.). Molecular size distributions of the humic acids were determined using a stirred cell ultrafiltration technique. The results of elemental analysis showed that soil humic acid from UJ contains higher oxygen content than humic acids from KR and KS (O/C ratios: 0.51 (UJHA) us. 0.45(KRHA), 0.43(KSHA)). The molecular size distribution revealed that the soil humic acids of UJ and YK contained a higher percentage of larger molecules of > 30,000 daltons, compared to those of KR and KS. The spectral features obtained from UV/vis., IR and CPMAS $^{13}C$ NMR showed that the aromatic character and oxygen containing functional groups in the humic acids from UJ and YK were relatively higher than those of KR and KS. These results indicate that the soil humic acids from UJ and YK were in a higher degree of humification, which may suggest higher affinity of the humic acids with radionuclides released in the soil environments.

Isolation and Quantitative Analysis of Tricin from Ears of Phragmites communis (갈대이삭으로부터 Tricin의 분리 및 함량 분석)

  • Woo, Hyun Sim;Lee, Seung-Young;Hwang, Buyng Su;Jeong, Sang-Chul;Kim, Dae Wook
    • Korean Journal of Pharmacognosy
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    • v.48 no.1
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    • pp.77-81
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    • 2017
  • The aim of this study was to investigate a validation method for determination of tricin in Phragmites communis ears. Tricin was isolated with chromatographic methods and used as the standard substances for quantitative analysis. The structural determination was characterized by comparing their NMR spectral data with values reported in the literature. For validation, the specificity, linearity, precision, accuracy, detection limits, and quantification limits of tricin was measured by HPLC. The results show that the specificity was satisfied with retention time and diode array detector (DAD) spectrum by analysis of tricin using HPLC. The limits of detection (LOD) for tricin was 0.84 mg/ml. Recovery of tricin was 98.80~108.22% with R.S.D values less than 2%. Intra-day and inter-day precisions of tricin in P. communis ears were 99.96~100.96% and 99.01~100.40%, respectively. Therefore, application of tricin was validated by an analytical method as major compound in P. communis ears.

NMR Spectroscopy and Mass Spectrometry of Phenylethanol Galactoside synthesized using Escherichia coli 𝛽-Galactosidase (대장균 베타-갈락토시데이즈를 이용하여 합성된 Phenylethanol Galactoside의 NMR Spectroscopy 및 Mass spectrometry)

  • Lee, Hyang-Yeol;Jung, Kyung-Hwan
    • Journal of the Korean Applied Science and Technology
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    • v.37 no.5
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    • pp.1323-1329
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    • 2020
  • To characterize the molecular structure of PhE-gal synthesized using Escherichia coli 𝛽-gal, NMR (1H- and 13C-) spectroscopy and mass spectrometry of PhE-gal were conducted. 1H NMR spectrum of PhE-gal showed multiple peaks corresponding to the galactosyl group, which is an evidence of galactosylation on 2-phenylethanol (PhE). Downfield proton peaks at 𝛿H 7.30~7.21 ppm showed the presence of aromatic protons of PhE as well as benzyl CH2 protons at 𝛿H 2.88 ppm. Up field proton peaks at 𝛿H 4.31 ppm, 4.07 ppm and multiple peaks from 𝛿H 3.86~3.38 ppm are indicative of galactocylation on PhE. 13C NMR spectrum revealed the presence of 12 carbons suggestive of PhE-gal. Among 12 carbon peaks from PhE-gal, the four peaks at 138.7, 129.0, 128.6 and 126.5 were assigned aromatic carbons in the phenyl ring. Three peaks at 129.0, 128.6 and 126.5 showed high intensities, indicating CH aromatic carbons. 13C NMR data of PhE-gal showed 6 monosaccharide peaks from galactose and 2 peaks from aliphatic chain of PhE, indicating that PhE-gal was galactosyl PhE. The mass value (sodium adduct ion of PhE-gal, m/z = 307.1181) from mass spectrometry analysis of PhE-gal, and 1H and 13C NMR spectral data were in good agreement with the expecting structure of PhE-gal. We are expecting that through future study it will eventually be able to develop a new additive with low cytotoxicity.

Synthesis, Potentiometric, Spectral Characterization and Microbial Studies of Transition Metal Complexes with Tridentate Ligand (세자리 리간드의 전이금속 착물에 대한 합성과 전위차 및 분광학적 확인 그리고 미생물학적 연구)

  • Jadhav, S.M.;Munde, A.S.;Shankarwar, S.G.;Patharkar, V.R.;Shelke, V.A.;Chondhekar, T.K.
    • Journal of the Korean Chemical Society
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    • v.54 no.5
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    • pp.515-522
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    • 2010
  • A relation between antimicrobial activities and the formation constants of solid complexes of Cu(II), Ni(II), Co(II), Mn(II) and Fe(III) with tridentate Schiff base ligand, 4-hydroxy-3(1-{2-(benzylideneamino)-phenylimino}-ethyl)-6-methyl-2Hpyran-2-one (HL) derived from o-phenylene diamines, dehydroacetic acid (DHA) and p-chloro benzaldehyde have been studied. The ligand and metal complexes were characterized by elemental analysis, conductivity, magnetic susceptibility, thermal analysis, X-ray diffraction, IR, $^1H$-NMR, UV-vis and mass spectra. From the analytical data, the stiochiometry of the complexes was found to be 1:2 (metal:ligand) with octahedral geometry. The molar conductance values suggest the nonelectrolytic nature of metal complexes. The X-ray diffraction data suggests monoclinic crystal system for Ni(II) and orthorhombic crystal system for Cu(II) and Co(II) complexes. The IR spectral data suggest that the ligand behaves as tridentate ligand with ONN donor atoms sequence towards central metal ion. Thermal behavior (TG/DTA) and kinetic parameters calculated by Coats-Redfern method suggests more ordered activated state in complex formation. The protonation constants of the complexes were determined potentiometrically in THF:water (60:40) medium at $25^{\circ}C$ and ionic strength ${\mu}=0.1\;M$ ($NaClO_4$). Antibacterial activities in vitro were performed against Staphylococcus aureu and Escherichia coli. Antifungal activities were studied against Aspergillus Niger and Trichoderma. The effect of the metal ions and stabilities of complexes on antimicrobial activities are discussed.

Inhibition of the expression on MMP-2, 9 and morphological changes via human fibrosarcoma cell line by 6,6'-bieckol from marine alga Ecklonia cava

  • Zhang, Chen;Li, Yong;Shi, Xiujuan;Kim, Se-Kwon
    • BMB Reports
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    • v.43 no.1
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    • pp.62-68
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    • 2010
  • Matrix Metalloproteinases (MMPs) are a family of zinc-endopeptidases which can degrade extracellular matrix (ECM) components and play important roles in a variety of biological and pathological processes. 6,6'-bieckol isolated and characterized from an edible marine brown alga Ecklonia cava (EC), according to the comprehensive spectral analysis of MS and NMR data. Here the influence of 6,6'-bieckol on expressions of MMPs was examined by zymography and western blot analysis via human fibrosarcoma cell line (HT1080). It is shown that 6,6'-bieckol significantly down regulated the expressions of MMP-2 and -9 in dose-dependent manner. The influence of 6,6'-bieckol on the cell viability and cell behavior of HT1080 cells were also investigated, our dates shown that it suppressed the migration and 3D culture in HT1080 cells. Meanwhile, we explored several signal pathways which may contribute to this process, and found the suppressing of MMPs expressions in HT1080 cells might be due to the suppression of NF-${\kappa}B$ signal pathway.

The proton nuclear magnetic resonance spectral analysis of human blood plasma lipoprotein (혈장지 단백질에 대한 핵자기 공명 분광 분석)

  • Song, In-Chan;Kang, Sa-Ouk;Kim, Noe-Kyeong;Im, Jung-Gi;Min, Byoung-Goo
    • Proceedings of the KOSOMBE Conference
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    • v.1989 no.05
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    • pp.29-34
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    • 1989
  • 300 MHz proton NMR spectra of human blood plasma were analyzed by deconvolution of spectrum, and we compared its results with Fossel's test in normal (15 cases), liver cancer (14 cases) , and other cancer (14 cases) groups. This analysis had enabled us to obtain dynamic characteristics of each individual lipoprotein. As a result of deconvolution method, the VLDL and chylomicron intensity level were found to be elevated in the patients with liver cancer. Moment ratio values of $CH_2$ resonance in the raw spectrum were found to be higher than the normal group for patients with, malignant tumors other than liver cancer. These differences between the three groups could not be found in the conventional Fossel's test. We could simulate plasma spectra by addition of spectra of individual lipoproteins through deconvolution method. Further clinical trials in larger populations and additional biochemical method may shed new light on many of clinical and biochemical interests for knowing characteristics about lipoprotein not separated from blood and the background of Fossel test.

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