• Title/Summary/Keyword: 1D and 2D NMR

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Analysis of Beauvericin and Unusual Enniatins Co-Produced by Fusarium oxysporum FB1501 (KFCC 11363P)

  • Song Hyuk-Hwan;Ahn Joong-Hoon;Lim Yoong-Ho;Lee Chan
    • Journal of Microbiology and Biotechnology
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    • v.16 no.7
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    • pp.1111-1119
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    • 2006
  • Beauvericins and enniatins are cyclohexadepsipeptides exhibiting various biological activities on animal systems, including humans. Fusarium oxysporum FB1501 (KFCC 11363P) that produces four different cyclohexadepsipeptides was isolated from soil in Korea and the structures of the four cyclohexadepsipeptides elucidated by HPLC, MS, IR, and NMR analyses. The molecular weights for compounds 1,2,3, and 4 were determined to be 654.5, 784.5, 668.6, and 682.5, respectively, on the basis of ESI-MS measurements. The IR spectra for all the compounds exhibited absorptions for ester $(1,733-1,743\;cm^{-1})$ and amide $(1,649-1,655\;cm^{-1})$ bonds that were very similar to those for beauvericin and enniatins with ester and amide absorptions. The results of the NMR analysis $(^{1}H,\;^{13}C,\;135-DEPT,\;COSY,\;HMQC,\;and\;HMBC;\;in\;COCl_{3})$ revealed that compounds 1,3, and 4 consisted of $_{L}-N-methyl\;valine$ (N-MeVal), $_{D}-{\alpha}-hydroxyisovaleic\;acid$ (Hiv), and 2-hydroxy-3-methylpentanoic acid (Hmp) residues (compound 1: three N-MeVal residues, two Hiv residues, and one Hmp residue; compound 3: three N-MeVal residues, one Hiv, and two Hmp residues; compound 4: three N-MeVal residues and three Hmp residues). Therefore, the compounds were identified as enniatin H (compound 1), enniatin I (compound 3), and enniatin MK1688 (compound 4). Compound 2 was analyzed as beauvericin according to 1D and 2D NMR analyses. This study is the first report related to the co-production of beauvericin with other unusual enniatins, such as enniatin H, enniatin I, and enniatin MK1688, by Fusarium oxysporum.

Studies on the Pharmaco-Constituents of Hydrocotyle japonica(II) (Hydrocotyle japonica의 약효성분에 관한 연구 (II))

  • 조의환;김일혁
    • YAKHAK HOEJI
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    • v.35 no.5
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    • pp.427-431
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    • 1991
  • A flavonoidal glycoside was isolated from the whole plant of Hydrocotyle japonica(Um belliferae) and identified as quercetin-3-O-$\beta$-D-galactoside quercetin-3-O-$\beta$-D-(hyperoside) (C$_{21}H_{20}O_{12}$.1/3 $H_2O$, yellow needle crystal, m.p. $249~250^{\circ}$, $[\alpha]^{28}_D^{\circ}$$-65.94^{\circ}$ in pyridine) by physicochemical properties and spectroscopic evidences(UV, IR, NMR and Mass etc., in comparison with authentic sample.

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A Solid-state 27Al MAS and 3QMAS NMR Study of Basaltic and Phonolitic Silicate Glasses (현무암과 포놀라이트 비정질 규산염의 원자구조 차이에 대한 고상핵자기 공명 분광분석 연구)

  • Park, Sun Young;Lee, Sung Keun
    • Journal of the Mineralogical Society of Korea
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    • v.28 no.1
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    • pp.61-69
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    • 2015
  • While the macroscopic properties and eruption style of basaltic and phonolitic melts are different, the microscopic origins including atomic structures are not well understood. Here we report the atomic structure differences of glass in diopside-anorthite eutectic composition (basaltic glass) and phonolitic glass using high-resolution 1D and 2D solid-state Nuclear Magnetic Resonance (NMR). The $^{27}Al$ MAS NMR spectra for basaltic glass and phonolitic glass show that the full width at half maximum (FWHM) of Al for basaltic glass is about twice than phonolitic glass, suggesting the topological disorder of basaltic magma is larger than that of phonolitic magma. The $^{27}Al$ 3QMAS NMR spectra for basaltic glass and phonolite glass show much improved resolution than the 1D MAS NMR, resolving Al and Al. Approximately 3.3% of Al is observed for basaltic glass, demonstrating the configurational disorder of basaltic magma is larger than phonolitic magma. This result confirms that the topological disorder of Al in basaltic glass is larger than that of phonolitic glass. The observed structural differences between basaltic glass and phonolitic glass can provide an atomistic origin for change of the macroscopic properties with composition including viscosity.

C-Flavonoidal Glycosides from Erythrina caffra Flowers

  • El-Masry, Sawsan;Hammoda, Hala M.;Radwan, Mohamed M.;Ross, Samir A.;Zaatout, Hala H.
    • Natural Product Sciences
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    • v.16 no.4
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    • pp.217-222
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    • 2010
  • A phytochemical investigation of the ethanolic extract of Erythrina caffra flowers from an Egyptian origin yielded three C-flavonoidal glycosides; 5,7,4'-trihydroxyflavone-8-C-$\beta$-D-glucopyranoside (vitexin) (1), 5,7,4'-trihydroxyflavone-6-C-$\beta$-D-glucopyranosyl-(1 $\rightarrow$ 2)-$\beta$-D-glucopyranoside (isovitexin-2"-$\beta$-D-glucopyranoside) (2), 5, 7, 4'-trihydroxyflavone-6, 8-di-C-$\beta$-D-glucopyranoside (vicenin-2) (3) and one O-flavonoidal glycoside; kaempferol-3-O-$\beta$-D.glucopyranosyl) (1 $\rightarrow$ 2)-$\beta$-D-glucopyranoside (4). The structures of the isolated compounds (1 - 4) were elucidated using different spectral techniques (UV, 1D and 2D NMR and HRESIMS). This is the first report for the isolation of flavonoidal glycosides from Erythrina caffra. The antibacterial, antifungal, antimalarial, and antileishmanial activities of the isolates were evaluated. In addition, the cytotoxic activity of the ethanolic extract and the main fractions were tested using brine shrimp bioassay.

Production of Inulin Fructotransferase (Depolymerizing) from Enterobacter sp. S45 (Enterobacter sp. S45에 의한 Inulin fructotransferase의 생산)

  • 강수일;김수일
    • Microbiology and Biotechnology Letters
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    • v.21 no.1
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    • pp.36-40
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    • 1993
  • A bacterial strain, producing extracellular inulin fructotransferase which converts inulin into di-D-fructofuranose dianhydride (DFA) was isolated from soil and presumed as Enterobacter sp. The DFA isolated on Bio-gel P2 column was identified as DFA III by high performance liquid chromatography and $^13C-nmr$ spectroscopy. The enzyme production was induced by inulin and markedly enhanced by the addition of corn steep liquor and $NH_4H_2P0_4$ for nitrogen source. Under optimum condition, the enzyme activity in the culture broth reached at maximum, 0.22 unit/ml after cultivation for 72 hour.

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Four New Furanosesquiterpenes Isolated from the Marine Sponge Dysidea species

  • Yeong Du Yoo;Jung-Rae Rho
    • Journal of the Korean Magnetic Resonance Society
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    • v.27 no.4
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    • pp.35-41
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    • 2023
  • From a marine sponge Dysidea species, four new furanosesquiterterpenoids were isolated and characterized. Their structural elucidation was achieved through an extensive analysis employing NMR, MS data, and DFT method. Notably, all compounds shared as identical molecular formula. Compound 2 was identified as a derivative of compound 1, while compounds 3 and 4 exhibited an identical planar structure. Determination of the configurations of chiral centers in compounds 1 and 2 involved a comparative analysis between measured and calculated ECD spectra, along with the application of DP4+ probability analysis. Distinctly, the configurations of isomers 3 and 4 were established by scrutinizing proton chemical shifts based on the NOE correlation.

Pyrophen Produced by Endophytic Fungi Aspergillus sp Isolated from Piper crocatum Ruiz & Pav Exhibits Cytotoxic Activity and Induces S Phase Arrest in T47D Breast Cancer Cells

  • Astuti, Puji;Erden, Willy;Wahyono, Wahyono;Wahyuono, Subagus;Hertiani, Triana
    • Asian Pacific Journal of Cancer Prevention
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    • v.17 no.2
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    • pp.615-618
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    • 2016
  • Ethyl acetate extracts obtained from culture of endophytic fungi Aspergillus sp isolated from Piper crocatum Ruiz & Pav, have been shown to possess cytotoxic activity against T47D breast cancer cells. Investigations were here conducted to determine bioactive compounds responsible for the activity. Bioassay guided fractionation was employed to obtain active compounds. Structure elucidation was performed based on analysis of LC-MS, $^1H$-NMR, $^{13}C$-NMR, COSY, DEPT, HMQC, HMBC data. Cytotoxity assays were conducted in 96 well plates against T47D and Vero cell lines. Bioassay guided isolation and chemical investigation led to the isolation of pyrophen, a 4-methoxy-6-(1'-acetamido-2'-phenylethyl)-2H-pyran-2-one. Further analysis of its activity against T47D and Vero cells showed an ability to inhibit the growth of T47D cells with IC50 values of $9.2{\mu}g/mL$ but less cytotoxicity to Vero cells with an $IC_{50}$ of $109{\mu}g/mL$. This compound at a concentration of 400 ng/mL induced S-phase arrest in T47D cells.

Salvatrione: A Diterpene-monoterpene Conjugate from Salvia bucharica

  • Ahmad, Viqar Uddin;Zahid, Muhammad;Ali, Muhammad Shaiq;Jassbi, Amir Reza;Ahmad, Shakeel;Ali, Zulfiqar;Iqbal, Muhammad Zafar
    • Natural Product Sciences
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    • v.6 no.2
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    • pp.66-69
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    • 2000
  • Salvia bucharica belonging to the family Lamiaceae (Labiatae), afforded a novel terpenoid (1) named as salvatrione. The structure of 1 was elucidated through extensive 2-D NMR experiments and the biogenetic pathway of 1 has also been proposed. On biogenetic grounds, 1 may be considered to be a pseudo-triterpenoid as it is derived from the coupling of mono/ diterpenic units and not from squalene.

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A new sesterterpenoid showing anti-inflammatory effect from the Marine Sponge Haliclona species

  • Lee, Kyung;Rho, Jung-Rae
    • Journal of the Korean Magnetic Resonance Society
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    • v.19 no.1
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    • pp.23-28
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    • 2015
  • Four spiroketal sestertepenoids (1 ~ 4) were isolated from the marine sponge Haliclona species. Their planar structures were completely determined from a combination of extensive 1D and 2D NMR experiments, and also the relative stereochemistry on the chiral centers were established by the ROESY experiment. Compounds 1 ~ 3 were determined as the same planar structures with different stereochemistry on the chiral centers C-11 and C-13. Of these, 1 was identified as a new stereoisomer. Four compounds showed the inhibition effect of nitric oxide (NO) production in LPS-stimulated RAW 264.7 cells (0.7~2.0 g/ml).

Gallotannins from Nut Shell Extractives of Camellia oleifera

  • HE, Yi-Chang;WU, Mei-Jie;LEI, Xiao-Lin;YANG, Jie-Fang;GAO, Wei;BAE, Young-Soo;KIM, Tae-Hee;CHOI, Sun-Eun;LI, Bao-Tong
    • Journal of the Korean Wood Science and Technology
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    • v.49 no.3
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    • pp.267-273
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    • 2021
  • Camellia nut shell was collected, dried at room temperature and ground to get fine powder. The powder was extracted three times with 95% EtOH, combined, evaporated, and then freeze dried. The crude powder was dissolved in H2O and then sequentially fractionated with n-hexane, CH2Cl2, EtOAc and n-BuOH. A part of EtOAc fraction was chromatographed on a silica gel and on a Sephadex LH-20 columns using MeOH, aqueous MeOH, EtOAc-n-hexane and EtOH-n-hexane to isolate gallotannins. Three gallotannins, 1,2-di-O-galloyl-β-D-glucopyranoside (2), 1,2,6-tri-O-galloyl-β-D-glucopyranoside (3) and 1,2,3,6-tetra-O-galloyl-β-D-glucopyranoside (4), including gallic acid (1), were isolated and elucidated by NMR and Mass spectroscopies. Although nothing new, these gallotannins were first reported from the nut shell extractives of camellia tree (Camellia oleifera C. Abel). This study was to investigate the chemical constituents, especially hydrolysable tannins, of nut shell extractives of Camellia oleifera and to provide basic information for the future chemical utilization of this species.