• Title/Summary/Keyword: 2-D NMR

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Hygrolansamycins A-D, O-Heterocyclic Macrolides from Streptomyces sp. KCB17JA11

  • Jang, Jun-Pil;Lee, Byeongsan;Heo, Kyung Taek;Oh, Tae Hoon;Lee, Hyeok-Won;Ko, Sung-Kyun;Hwang, Bang Yeon;Jang, Jae-Hyuk;Hong, Young-Soo
    • Journal of Microbiology and Biotechnology
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    • v.32 no.10
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    • pp.1299-1306
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    • 2022
  • Six ansamycin derivatives were isolated from the culture broth of Streptomyces sp. KCB17JA11, including four new hygrolansamycins A-D (1-4) and known congeners divergolide O (5) and hygrocin C (6). Compounds 1-5 featured an unusual six-membered O-heterocyclic moiety. The isolation workflow was guided by a Molecular Networking-based dereplication strategy. The structures of 1-4 were elucidated using NMR and HRESIMS experiments, and the absolute configuration was established by the Mosher's method. Compound 2 exhibited mild cytotoxicity against five cancer cell lines with IC50 values ranging from 24.60 ± 3.37 µM to 49.93 ± 4.52 µM.

The Chirality Conversion Reagent for Amino Acids Based on Salicyl Aldehyde

  • Yoon, Hoe-Jin;Jung, Hein;Ahn, Yun-Soo;Nandhakumar, Raju;Kim, Jun-Soo;Kim, Kwan-Mook
    • Bulletin of the Korean Chemical Society
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    • v.33 no.5
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    • pp.1715-1718
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    • 2012
  • 2-Hydroxy-6-(1-(3-phenylurylphenyl)ethoxy)-benzaldehyde ($\mathbf{2}$) has been synthesized in racemic form from 1,3-Dihydroxybenzene via formylation and reaction with 3-phenyluryl-methylbenzylbromide. The optically pure form of $\mathbf{2}$ was separated by normal silica column chromatography from the imine diastreomer which was obtained by the reaction of racemic mixture of $\mathbf{2}$ with optically pure leucinol. The absolute configuration of the separated enantiomer of $\mathbf{2}$ was decided from the energy calculation of the corresponding imine diastereomers. The activity of $\mathbf{2}$ as a chirality conversion reagent (CCR) for amino acids was determined by $^1H$ NMR analysis. The efficiency of $\mathbf{2}$ is not better than the previous CCRs based on binaththol. Compound $\mathbf{2}$, however, has lower molecular weight compared to other CCRs. This work demonstrates that asymmetric carbon can control the selectivity of amino acids.

Synthesis and Characterization of Polybenzimidazoles Containing Perfluorocyclobutane Groups for High-temperature Fuel Cell Applications

  • Chang, Bong-Jun;Kim, Dong-Jin;Kim, Jeong-Hoon;Lee, Soo-Bok;Joo, Hyeok-Jong
    • Korean Membrane Journal
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    • v.9 no.1
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    • pp.43-51
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    • 2007
  • This paper describes the preparation and characterization of two kinds of fluorinated polybenzimidazole (PBI)s which can be potentially used for phosphoric acid-doped, high-temperature polymer electrolyte membrane fuel cells. Two kinds of perfluorocyclobutane (PFCB)-containing monomers were prepared via following synthetic steps; after fluoroalkylation of methyl 3-(hydroxy) benzoate and methyl 4-(hydroxy) benzoate with 1,2-dibromotetrafluoroethane and subsequent Zn-mediated dehalogenation, these compounds were cyclodimerized at $200^{\circ}C$ affording the ester-terminated monomers containing PFCB ether groups. The synthesized intermediates and monomers were characterized using FT-IR, $^1H-NMR,\;^{19}F-NMR$, and mass spectroscopy. The fluorinated PBIs were then successfully prepared through the solution polycondensation of the monomers and 3,3'-diaminobenzidine in polyphosphoric acid. Compared with traditional PBI, the glass transition temperatures of the fluorinated PBIs were obtained at $262^{\circ}C\;and\;269^{\circ}C$ which are lower than that of PBI and their initial degradation temperatures were still high over $400^{\circ}C$ under nitrogen. The fluorinated PBIs showed higher d-spacing values and improved solubility in several organic solvents as well as phosphoric acid, which confirmed they could be good candidates for the high temperature fuel cell membranes.

Production of Sphingolipids by Submerged Culture of Ganoderma lucidum and Cutaneous Hydration Effect (Ganoderma lucidum 균사체의 액체배양의 의한 sphingolipids의 생산 및 피부 보습 효과)

  • Ryu, Il-Hwan;Kim, Jung-Enn;Lee, Kap-Sang
    • Korean Journal of Food Science and Technology
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    • v.36 no.4
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    • pp.655-661
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    • 2004
  • Sphingolipid production was investigated through Ganoderma lucidum-submerged cultivation. Crude sphingolipid obtained from G. lucidum was purified by methanol precipitation, Dowex AG DW-X8 (H+ form) cation exchange chromatography, and preparative thin layer chromatography, Structure and functionalities of purified sphingolipid were elucidated including cutaneous hydration effect. Possibility of use as cosmetics material and new biomaterial was explored. Production was 0.4 g/L at 1% yield. Purified sphingolipid was identified as D-ribo-1,3,4-trihydroxy-2-aminoocta decan through UV/VIS, FT-IR, and $^1H-NMR$. Sphingolipids increased skinmate value for cutaneous hydration effect by 20% at $500\;{\mu}g/mL$ and decreased skin roughness at $100\;{\mu}g/mL$. Results suggest shingolipids from G. lucidum are effective for cutaneous hydration and improvement of skin roughness.

The Preliminary Study on the Structure of Cop Protein by CD and NMR

  • Kim, Yun-Kyong;Park, Sang-Ho;Lee, Jee-Hyun;Kwak, Jin-Hwan;Lee, Bong-Jin
    • Journal of the Korean Magnetic Resonance Society
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    • v.3 no.2
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    • pp.100-108
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    • 1999
  • Cop protein is the transcription repressor protein in rolling circle replication plasmid. With antisense RNA, Cop protein controls the copy number of plasmid. Cop family proteins have been found in various plasmids. Among Cop family proteins, Cop studied in this paper consists of 55 amino acids (Mw. 6,400), and was known to have trimer structure. Since no structural facts are elucidated, we have carried out preliminary experiments aimed at the elucidation of its three dimensional structure. The secondary structure of Cop is studied by CD and NMR. To solve the aggregation of Cop at high concentration, we tested various detergents and salts. The addition of detergents and salts could not solve the aggregation problem. However, we found that concentration is important in solving the aggregation problem. We knew that 0.18mM in 50mM potassium phosphate without any other ingredients is maximum concentration not to aggregate. Wa also investigated the pH dependence of Cop protein, and knew that Cop protein is more stable in acid state. At various temperatures, 15N-1H HSQC spectra were measured in order to find the optimal experimental condition. To enhance the peak resolution, 3D NOESY-HSQC spectrum is acquired. Since there are NOE peaks in the NH-NH region, we knew that Cop protein has $\alpha$-helical content, which was also confirmed by CD.

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Phenazine-1-carboxamide, an Extrolite Produced by Pseudomonas aeruginosa Strain (CGK-KS-1) Isolated from Ladakh and India, and its Evaluation Against Various Xanthomonas spp.

  • Sirisha, K.;Kumar, C. Ganesh;Ramakrishna, Kallaganti Venkata Siva;Gunda, Shravan Kumar
    • Microbiology and Biotechnology Letters
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    • v.45 no.3
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    • pp.209-217
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    • 2017
  • In the enduring investigation of the bioactive microbes, Pseudomonas aeruginosa strain (referred to as CGK-KS-1 (ICTB-315)), isolated from Chumathang hot spring, Ladakh, and India, was identified to possess a major bioactive fraction with antimicrobial and anti-biofilm properties. This bioactive metabolite was purified through bioactivity-guided fractionation. The chemical structure of this major compound was elucidated as phenazine-1-carboxamide (PCN) based on $^1H$ and $^{13}C$ NMR, FT-IR, EI-HR-MS and 2D NMR spectroscopic techniques. In the current study, PCN exhibited antimicrobial activity with MIC values ranging between $1.9-3.9{\mu}g/ml$ against various test human pathogens and Xanthomonas spp. PCN showed the anti-biofilm property with the $IC_{50}$ values ranging from 17.04 to $60.7{\mu}M$ against different test pathogens. The in silico docking studies showed PCN strongly interacted with various proteins of different Xanthomonas spp. with high binding energies. We report herein for the first time the anti-biofilm property and the docking studies of PCN. The extrolite from P. aeruginosa strain CGK-KS-1 showed promising bioactivities and may be considered as a potential candidate for application in various biocontrol strategies.

Analysis of metabolites in wheat roots in response to salinity stress

  • Kim, Da-Eun;Roy, Swapan Kumar;Kim, Ki-Hyun;Cho, Seong-Woo;Park, Chul-Soo;Lee, Moon-Soon;Woo, Sun-Hee
    • Proceedings of the Korean Society of Crop Science Conference
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    • 2017.06a
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    • pp.200-200
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    • 2017
  • Salinity stress is one of the most important abiotic stresses and severely impairs plant growth and production. Root is the first site for nutrient accumulation like as $Na^+$ in the plant. To investigate the response of wheat root under salinity stress, we executed the characterization of morphology and analysis of metabolites. Wheat seeds cv. Keumgang (Korean cultivar) were grown on the moist filter paper in Petri dish. After 5 days, seedlings were transferred to hydroponic apparatus at 1500 LUX light intensity, at $20^{\circ}C$ with 70% relative humidity in a growth chamber. Seedlings (5-day-old) were exposed to 50mM, 75mM, 100mM NaCl for 5 days. Ten-day-old seedlings were used for morphological characterization and metabolite analysis. Root and leaf length became shorter in high NaCl concentration compared to following NaCl treatment. For confirmation of salt accumulation, wheat roots were stained with $CoroNa^+$ Green AM, and fluoresce, and the image was taken by confocal microscopy. $Na^+$ ion accumulation rate was higher at 100mM compared to the untreated sample. Furthermore, to analyze metabolites in the wheat root, samples were extracted by $D_2O$ solvent, and extracted sample was analyzed by 1H NMR spectroscopy. Fourteen metabolites were identified in wheat roots using NMR spectroscopy. Methanol and ethanol were up-regulated, whereas formate, aspartate, aminobutyrate, acetate and valine were down-regulated under salinity stress on roots of wheat. Fumarate had no change, while glucose, betaine, choline, glutamate and lactate were unevenly affected during salinity stress.

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Bio-assay Guided Isolation and Identification of α-Glucosidase Inhibitors from the Leaves of Diospyros lotus (고욤나무 잎으로부터 활성유도 분획법에 의한 α-Glucosidase 저해물질 분리 및 확인)

  • Kim, Sang Jun;Kim, Ji-Ae;Kim, Da Hye;Kwak, Seol Hwa;Yu, Kang-Yeol;Jang, Seon Il;Kim, Seon-Yeong;Jeong, Seung-Il
    • Korean Journal of Pharmacognosy
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    • v.46 no.2
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    • pp.105-108
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    • 2015
  • To establish the anti-diabetic(α-glucosidase inhibitory) activity of D. lotus leaf extract, isolate and identify the constituents responsible for the activity. The methanolic extract of leaves was partitioned between water, n-butanol and ethyl acetate. Bio-assay guided fractionation, based on inhibition of ;${\alpha}$-glucosidase, allowed isolation and identification of the active components. Liquid chromatography/mass spectrometry(LC/MS), 1 H-NMR and 13 C-NMR spectra analyses demonstrated that the active compound was myricetin-3-O-;${\alpha}$-L-rhamnoside(1). Compound 1 demonstrated a strong inhibition on the α-glucosidase, in vitro and ;${\alpha}$-glucosidase inhibitory value was calculated as 98.08%, when that of a reference drug, acarbose was estimated as 83.03%. The present study indicates compound 1 could be considered as an ;${\alpha}$-glucosidase inhibitor and developed as an important antidiabetes agent for type II diabetes therapy.

High-Resolution MRI Study on Mouse Brain Using Micro-Imaging (초고해상도 미세영상 기법을 이용한 Mouse 뇌의 자기공명영상 연구)

  • Han, Doug-Young;Yoon, Moon-Hyun;Choe, Bo-Young
    • Investigative Magnetic Resonance Imaging
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    • v.12 no.2
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    • pp.142-147
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    • 2008
  • Purpose : By using the micro-imaging unit modified from NMR spectrometer, the high resolution MRI protocols of finer than 100 micron in 5 minutes, is sought for mouse, which plays a central role in animal studies Materials and Methods : C57BL/6 mouse, lighter than 50 gram, is used for the experiments. The superconducting magnet is vertical type with 89 mm inner diameter at 4.9 Tesla. The diameter of rf-coil is 30 mm. Mostly used techniques are the fast spin echo and the gradient echo pulse sequence. Results : For 2D images, proton density and T2 weighted images are obtained and their optimum experimental variables were sought. Minute structure of mouse brain can be recognized and 3D brain image is also obtained additionally. 3D image will be useful particularly for the dynamic contrast study using various contrast agents. Conclusion : Like the case of human and other small animals, the high resolution of mouse brain is enough to recognize the minute structure of it. Recently, similar studies are reported domestically, but it seems only a beginning stage. Due to easiness of breeding/control, mouse MRI study will soon play a vital part in brain study.

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Isolation of Alkaloids with Immune Stimulating Activity from Oryza sativa cv. Heugnambyeo (흑남벼 함유 Alkaloid 분리 및 면역효능 연구)

  • Ryu, Min-Ju;Chung, Ha-Sook
    • Journal of the Korean Chemical Society
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    • v.54 no.1
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    • pp.65-70
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    • 2010
  • We describe the immune stimulatory effects of compounds determined by means of activity-monitored extraction and isolation techniques. As a result, 4-carboethoxy-6-methoxy-2-quinolone (1) and 4-carboethoxy-6-hydroxy-2-quinolone (2) were isolated from the ethyl acetate-soluble fraction of the Oryza sativa cv. Heugnambyeo bran, and were determined to exert significant inhibitory effects in macrophage cell line (murine RAW 264.7) and murine splenocytes. The structures were elucidated on the basis of spectroscopic evidence, particularly the results obtained via hetero nuclear multiple-bond connectivity and high-resolution MS spectroscopy. Up to date, compound (1) was isolated as natural sources for the first time.