• Title/Summary/Keyword: high-pressure NMR

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Complete 1H-NMR and 13C-NMR spectral assignment of five malonyl ginsenosides from the fresh flower buds of Panax ginseng

  • Wang, Yu-Shuai;Jin, Yin-Ping;Gao, Wei;Xiao, Sheng-Yuan;Zhang, Yu-Wei;Zheng, Pei-He;Wang, Jia;Liu, Jun-Xia;Sun, Cheng-He;Wang, Ying-Ping
    • Journal of Ginseng Research
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    • v.40 no.3
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    • pp.245-250
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    • 2016
  • Background: Ginsenosides are the major effective ingredients responsible for the pharmacological effects of ginseng. Malonyl ginsenosides are natural ginsenosides that contain a malonyl group attached to a glucose unit of the corresponding neutral ginsenosides. Methods: Medium-pressure liquid chromatography and semipreparative high-performance liquid chromatography were used to isolate purified compounds and their structures determined by extensive one-dimensional- and two-dimensional nuclear magnetic resonance (NMR) experiments. Results: A new saponin, namely malonyl-ginsenoside Re, was isolated from the fresh flower buds of Panax ginseng, along with malonyl-ginsenosides Rb1, Rb2, Rc, Rd. Some assignments for previously published $^1H$- and $^{13}C$-NMR spectra were found to be inaccurate. Conclusion: This study reports the complete NMR assignment of malonyl-ginsenoside Re, $Rb_1$, $Rb_2$, Rc, and Rd for the first time.

Phytochemical Identification from Boehmeria nivea Leaves and Analysis of (-)-Loliolide by HPLC

  • Cho, Sunghun;Lee, Dong Gu;Jung, Yong-Su;Kim, Ho Bang;Cho, Eun Ju;Lee, Sanghyun
    • Natural Product Sciences
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    • v.22 no.2
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    • pp.134-139
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    • 2016
  • Phytochemicals were isolated from leaves of the fiber crop, ramie (Boehmeria nivea, Bn), using open column chromatography and medium pressure liquid chromatography. Their structures were identified as ${\beta}$-sitosterol, (-)-loliolide, rutin, and pyrimidinedione by MS, $^1H$-, and $^{13}C$-NMR spectroscopic analysis. Among them, (-)-loliolide was isolated for the first time from B. nivea. A content analysis of (-)-loliolide in B. nivea collected from different regions and harvest times was conducted by HPLC. The highest content of (-)-loliolide was found in Bn-23 harvested in September. These results will be helpful to use the plant which harvest in September as a high content phytochemical additive in food, health supplements, and medicinal products.

New Polyacetylene Compounds from Panax Ginseng C. A. Meyer$^\dag$

  • Shim, Sang-Chul;Chang, Suk-Ku;Hur, Chan-Woo;Kim, Chang-Kew
    • Bulletin of the Korean Chemical Society
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    • v.8 no.4
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    • pp.272-275
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    • 1987
  • Two polyacetylene compounds having diyn-ene chromophore were isolated from fresh Korean ginseng roots through solvent fractionation, partition and silica gel column chromatography. The low pressure semi-preparative liquid chromatography and high performance preparative liquid chromatography were used for final separation of polyacetylenic fractions. The chemical structures of these polyacetylenes were determined to be heptadeca-1,8-dien-4,6-diyn-3,10-diol and heptadeca-1,4-dien-6,8-diyn-3,10-diol by UV, FT-IR, $^1H\;NMR,\;^{13}C\;NMR,$ mass spectra and elemental analysis.

Study of Xenon Adsorption on Alkaline-Earth Cation in Y Zeolite Based on Chemical Shift in $^{129}Xe$ NMR Spectrum (Y 제올라이트내에서 $^{129}Xe$ 핵자기 공명의 화학적 이동을 근거로 한 알칼리 토금속 양이온의 Xe 흡착 현상 연구)

  • Chanho Park;Ryong Ryoo
    • Journal of the Korean Chemical Society
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    • v.36 no.3
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    • pp.351-359
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    • 1992
  • Interaction of xenon with alkaline-earth cations in Y zeolite supercage was studied by xenon adsorption and $^{129}Xe$ NMR experiments. The CaY and the BaY samples were prepared by exchanging $Ca^{2+}$ and $Ba^{2+}$ into a high-purity NaY zeolite. Xenon adsorption isotherms of these samples were obtained by using a conventional volummetric gas adsorption apparatus in the range of 260 to 320 K and the chemical shift in the $^{129}Xe$ NMR spectrum of the adsorbed xenon was measured at 296 K. The chemical shift against pressure was quantitatively explained assuming that the xenon gas exchanged very rapidly between various adsorption sites consisting of zeolite-framework surface and alkaline-earth ion. From this analysis, it was found that the alkaline-earth ion adsorbed xenon more strongly than $Na^+$ ion and zeolite-framework surface. Baring on the difference of the adsorption strength, the number of the alkaline-earth cations present in the zeolite supercage could be estimated by analyzing the adsorption isotherm.

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The Study on the Synthesis of Propellant with High Nitrogen Content (고질소 추진물질 합성 연구)

  • Lee, Woonghee;Kim, Minjun;Park, Youngchul
    • Journal of the Korean Society of Propulsion Engineers
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    • v.19 no.3
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    • pp.96-102
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    • 2015
  • Traditional propellants emit toxic gases such as carbon dioxide and hydrogen chloride during combustion which are harmful to the environment. This study established a synthetic process of a high nitrogen containing derivative of tetrazine, 3,3-Azobis(6-Amino-1,2,4,5-Tetrazine) (DAAT), which can be applied as solid fuels for a solution to environmental concerns. Also, this paper described the detailed process and the analytic results of properties, which were not mentioned in previous reports. The compound was characterized by NMR, IR spectroscopy, and thermal, impact, and friction stability were measured. In addition, the heats of formation (${\Delta}H_f$) and detonation properties (pressure and velocity) of DAAT were calculated using Gaussian 09 and EXPLO5 programs.

Identifying antibacterial activity components of cosmos flower extracts (코스모스 추출물의 항균활성 성분 탐색)

  • Kim, Mijung;Ahn, Seunghyun;Park, Seyeon
    • Journal of Applied Biological Chemistry
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    • v.63 no.3
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    • pp.249-257
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    • 2020
  • This study investigated whether the extracts from cosmos flowers exhibit antibacterial activities and identified which components were ascribed to the antibacterial effects. The antibacterial effects of extracts from white, pink, and violet cosmos flowers were observed for 24 h after inoculation with four kinds of bacteria, including Staphylococcus aureus, Staphylococcus epidermidis, Pseudomonas aeruginosa, and Escherichia coli. Among the three fractions of cosmos flower extracts, the best antibacterial activity against the four bacteria was observed in the extracts isolated from the EtOAc layer. However, the extracts from the CHCl3 layer were also effective against S. aureus. Moreover, the first of white, second of pink, and first of violet silica gel fractions (Fr.) isolated from the EtOAc layer exhibited minimal inhibition at a concentration of 0.1 mg/mL. Comparison of NMR and High-Pressure Liquid Chromatography results between silica gel Fr. and apigenin suggested that the effective fractions can contain a component including apigenin moiety.

Consoramides A-C, New Zwitterionic Alkaloids from the Fungus Irpex consors

  • Kim, Ji-Yul;Ki, Dae-Won;Lee, Yoon-Ju;Ha, Lee Su;Woo, E-Eum;Lee, In-Kyoung;Yun, Bong-Sik
    • Mycobiology
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    • v.49 no.4
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    • pp.434-437
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    • 2021
  • In our ongoing search for new secondary metabolites from fungi, a basidiomycete fungus Irpex consors was selected for mycochemical investigation, and three new zwitterionic alkaloids (1-3) and five known compounds (4-8) were isolated from the culture broth (16 l) of I. consors. The culture filtrate was fractionated by a series of column chromatography including Diaion HP-20, silica gel, and Sephadex LH-20, Sep-Pak C18 cartridge, medium pressure liquid chromatography (MPLC), and high pressure liquid chromatography (HPLC) to yield eight compounds (1-8). The structures of the isolated compounds were elucidated by the interpretation of nuclear magnetic resonance (NMR) spectra and high-resolution mass spectrometry (HR-MS). Their antioxidant and antibacterial activities were examined. The zwitterionic structures of three new sesquiterpene alkaloids (1-3) were determined together with five known compounds identified as stereumamide E (4), stereumamide G (5), stereumamide H (6), stereumamide D (7), and sterostrein H (8). This is the first report of the zwitterionic alkaloids in the culture broth of I. consors. Three new zwitterionic alkaloids were named as consoramides A-C (1-3).

Studies on the Synthesis of N-alkyl-N-acyl glucamines (N-alkyl-N-acyl glucamines의 합성에 관한 연구)

  • Ahn, Ho-Jeong;Cho, Kyu-Suk
    • Applied Chemistry for Engineering
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    • v.7 no.1
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    • pp.171-176
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    • 1996
  • The easily biodegradable nonionic surfactant of glucamide(N-alkyl-N-acyl glucamine) was synthesized by the two-step reaction. The first step was the amination between alkylamine and glucose in methanol. Then, alkyl glucamines were obtained by reduction using Ni catalyst under the high pressure with 86~93% of reaction yield. The second step was the synthesis of glucamide from alkyl glucamine and fatty acid methyl ester in methanol under the alkali catalytic condition while refluxing the solvent. The reaction yield of this step was 84~95% except the benzyl glucamine, which the reaction yield was 50~70%. The molecular structure of four kinds of alkyl glucamine and 16 kinds of glucamide with different alkyl and acyl groups was studied by IR, MS and NMR.

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Anticoagulant Properties of the Active Compound Derived from Cinnamomum cassia Bark

  • Lee, Hoi-Seon
    • Food Science and Biotechnology
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    • v.16 no.2
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    • pp.218-222
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    • 2007
  • The anticoagulant properties of Cinnamomum cassia bark-derived materials were evaluated against platelet aggregation induced by arachidonic acid (AA), collagen, platelet activating factor (PAF), or thrombin, and these effects were then compared to those of three commercially available compounds (cinnamic acid, cinnamyl alcohol, and aspirin). The active constituent obtained from C. cassia barks was isolated by silica gel column chromatography and high pressure liquid chromatography (HPLC), and was characterized as trans-cinnamaldehyde by MS, $^1H-NMR$, $^{13}C-NMR$, and IR spectroscopy. With regard to 50% inhibitory concentration ($IC_{50}$) values, cinnamaldehyde was found to effectively inhibit platelet aggregation induced by AA ($IC_{50},\;43.2\;{\mu}M$) and collagen ($IC_{50},\;3.1\;{\mu}M$). By way of comparison, cinnamaldehyde proved to be a significantly more potent platelet inhibitor against platelet aggregation induced by collagen than aspirin. The effect exerted by cinnamaldehyde against platelet aggregation induced by AA was 1.2 times less than that of aspirin. These results indicate that cinnamaldehyde may prove useful as a lead compound for the inhibition of platelet aggregation induced by AA and collagen.

Equimolar Carbon Dioxide Absorption by Ether Functionalized Imidazolium Ionic Liquids

  • Sharma, Pankaj;Park, Sang-Do;Park, Ki-Tae;Jeong, Soon-Kwan;Nam, Sung-Chan;Baek, Il-Hyun
    • Bulletin of the Korean Chemical Society
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    • v.33 no.7
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    • pp.2325-2332
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    • 2012
  • A series $[C_3Omim]$[X] of imidazolium cation-based ILs, with ether functional group on the alkyl side-chain have been synthesized and structure of the materials were confirmed by various techniques like $^1H$, $^{13}C$ NMR spectroscopy, MS-ESI, FTIR spectroscopy and EA. More specifically, the influence of changing the anion with same cation is carried out. The absorption capacity of $CO_2$ for ILs were evaluated at 30 and $50^{\circ}C$ at ambient pressure (0-1.6 bar). Ether functionalized ILs shows significantly high absorption capacity for $CO_2$. In general, the $CO_2$ absorption capacity of ILs increased with a rise in pressure and decreased when temperature was raised. The obtained results showed that absorption capacity reached about 0.9 mol $CO_2$ per mol of IL at $30^{\circ}C$. The most probable mechanism of interaction of $CO_2$ with ILs were investigated using FTIR spectroscopy, $^{13}C$ NMR spectroscopy and result shows that the absorption of $CO_2$ in ether functionalized ILs is a chemical process. The $CO_2$ absorption results and detailed study indicates the predominance of 1:1 mechanism, where the $CO_2$ reacts with one IL to form a carbamic acid. The $CO_2$ absorption capacity of ILs for different anions follows the trend: $BF_4$ < DCA < $PF_6$ < TfO < $Tf_2N$. Moreover, the as-synthesized ILs is selective, thermally stable, long life operational and can be recycled at a temperature of $70^{\circ}C$ or under vacuum and can be used repeatedly.