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

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Chemical Composition of Clausena lansium (Lour.) Skeels Leaves and Antifungal Activity

  • Vu, Duc Nam;Teruhisa, Fujimatsu;Hirofumi, Takigawa;Hiroshi, Kusuoku;Nguyen, Minh Khoi;Le, Viet Dung;Do, Thi Ha;Hiroshi, Hashimoto
    • Natural Product Sciences
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    • v.22 no.1
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    • pp.35-40
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    • 2016
  • The first study on chemical constituents and biological activities of Clausena lansium (Lour.) Skeels (Rutaceae) growing in Vietnam has been done. Phytochemical investigation of n-hexane extract led to the isolation of five compounds: dihydroindicolactone (1), 8-geranyloxy psoralen (2), imperatorin (3), heraclenol (4) and indicolactone (5), in which this is the first report on the presence of dihydroindicolactone (1). Their structures were elucidated based on LC/MS/NMR hyphenated techniques as well as comparison with those of literature data. The n-hexane extract and its subfractions, ethanol 95% extract and several isolated compounds were evaluated for antifungal activity.

Nitrite Scavenging Ability and SOD-like Activity of a Sterol Glucoside form Chrysanthemum coronarium L. var. spatiosum (쑥갓 스테롤배당체의 아질산염소거작용 및 SOD 유사활성)

  • Cho, Min-Jung;Park, Mi-Jung;Lee, Heum-Sook
    • Korean Journal of Food Science and Technology
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    • v.39 no.1
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    • pp.77-82
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    • 2007
  • From the total methanolic extract of Chrysanthemum coronarium L. var. spatiosum (Compositae), nitrite scavenging ability and superoxide dismutase (SOD)-like activity were analyzed as antioxidative characteristics. After successive partitioning with chloroform, n-butanol, and water, the chloroform fraction showed the most significant nitrite scavenging ability with an $IC_{50}$ value of 39 ppm compared with the values of vitamin C and chlorogenic acid, 15 ppm and 36 ppm, respectively. The active fraction was subjected to silica gel and Sephadex LH-20 column chromatography, and the compound was isolated and identified as ${\beta}-sitosterol-O-{\beta}-D-glucoside$ using $^{1}H-NMR$ and $^{13}C-NMR$ spectral data. The glucoside was further hydrolyzed and confirmed as a glycosylated ${\beta}-sitosterol$. The compound and its aglycone, ${\beta}-sitosterol$, showed different nitrite scavenging and SOD-like activity. The $IC_{50}$ value of nitrite scavenging ability of the compound was 335 ppm at pH 1.5, while that of its aglycone was 41 ppm. As for the SOD-like activity, the $EC_{50}$ values of the sterol and the glucoside were 1,291 ppm and >2,000 ppm, respectively, compared with those of vitamin C and chlorogenic acid, 38 ppm and 449 ppm, respectively.

Cytotoxic Sesquiterpenoid from the Seeds of Amomum xanthioides

  • Kim, Ki-Hyun;Choi, Jung-Wook;Choi, Sang-Un;Lee, Kang-Ro
    • Natural Product Sciences
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    • v.17 no.1
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    • pp.10-13
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    • 2011
  • As parts of our continuing search for biologically active compounds from medicinal plants, we investigated the constituents of the seeds of Amomum xanthioides and isolated a sesquiterpenoid, a nerolidol derivative from its MeOH extract. The chemical structure was determined by spectroscopic methods, including 1D and 2D NMR to be ($2S^*$,$2'R^*$,$5'S^*$)-2-(5'-ethenyltetrahydro-5'-methylfuran-2'-yl)-6-methylhept-5en-2-ol (1). Compound 1 was isolated for the first time from nature source. Compound 1 exhibited a good cytotoxicity against SK-OV-3 and SK-MEL-2 cells ($IC_{50}$: 16.7 and $8.6\;{\mu}M$, respectively) using a SRB bioassay. In this study, we also determined the absolute configuration of 2 reported in previous paper.

Isolation and Identification of Antioxidants from Methanol Extract of Sword Bean (Canavalia gladiata) (작두콩의 메탄올 추출물로부터 항산화 활성 화합물의 분리 및 동정)

  • Kim, Jong-Pil;Lee, Hyang-Hee;Moon, Jae-Hak;Ha, Dong-Ryong;Kim, Eun-Sun;Kim, Jin-Hwan;Seo, Kye-Won
    • Korean Journal of Food Science and Technology
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    • v.45 no.6
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    • pp.777-784
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    • 2013
  • The ethyl acetate (EtOAc) layer of Canavalia gladiata (sword bean) methanol extracts showed higher 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical-scavenging activity than other layers. Four phenolic compounds were isolated from the EtOAc layer by silica gel column chromatography and prep-HPLC using a guided DPPH radical-scavenging assay. The isolated compounds were identified as methyl gallate (1), gallic acid (2), 1,6-di-O-galloyl ${\beta}$-$\small{D}$-glucopyranoside (3), and 1,4,6-tri-O-galloyl ${\beta}$-$\small{D}$-glucopyranoside (4) based on MS and NMR analyses. Among the four compounds, no. 4 was isolated from this plant for the first time. Their DPPH radical-scavenging activities based on $SC_{50}$ decreased in the following order: 4 (6.9 ${\mu}M$)>3 (8.3 ${\mu}M$)>2 (10.0 ${\mu}M$)>1 (10.3 ${\mu}M$).

Synthesis and Characterization of 1-DABTR as Insensitive Energetic Plasticizer (둔감 에너지 가소제 1-DABTR의 합성 및 특성 평가)

  • Lee, Woonghee;Kim, Minjun;Park, Youngchul;Lee, Bumjae
    • Journal of the Korean Society of Propulsion Engineers
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    • v.21 no.6
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    • pp.32-38
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    • 2017
  • Plasticizers play roles in increasing plasticity or fluidity during mixing. Representative plasticizers are DOS, DOA, IDP and BTTN. In particular, BTTN is an energy plasticizer that helps propellant performance and is widely used. However these compounds are sensitive relatively. So, in order to develop insensitive energetic plasticizer, synthesis of one of the derivatives of triazole, 4,5-bis (azido methyl)-(1-butyl)-1,2,3-triazole (1-DABTR), was studied. Also, the compound was characterized by NMR, IR spectroscopy, and physicochemical properties such as glass transition temperature, melting point, decomposition temperature, density, viscosity and impact sensitivity were measured. In addition, the heats of formation (${\Delta}H_f$) of 1-DABTR was also calculated using Gaussian 09.

Monoamine Oxidase Inhibitory Flavonoids from the Root Bark of Cudrania tricuspidata

  • Han, Xiang-Hua;Hwang, Ji-Hye;Hong, Seong-Su;Choe, Sang-Gil;Lee, Chul;Lee, Moon-Soon;Lee, Dong-Ho;Lee, Myung-Koo;Lee, Mi-Kyeong;Hwang, Bang-Yeon
    • Natural Product Sciences
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    • v.16 no.2
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    • pp.75-79
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    • 2010
  • Two new benzylated flavonoids, 5,7,4'-trihydroxy-6-p-hydroxybenzylflavanone (1) and 5,7,4'-trihydroxy-6,8-di-p-hydroxybenzylflavanone (2) together with six known flavonoids, kaempferol (3), artocarpesin (4), cycloartocarpesin (5), cudraflavone D (6), gericudranin E (7), and leachianone G (8) have been isolated from the root bark of Cudrania tricuspidata. The structures of 1 and 2 were characterized based on spectroscopic data including 1D- and 2D-NMR. All the isolates were evaluated for their inhibitory effects of monoamine oxidase (MAO). Among them, kaempferol (3), artocarpesin (4), and cudraflavone D (6) showed moderate inhibitory effects with $IC_{50}$ values of 82.3, 30.8, and $71.8\;{\mu}M$, respectively.

Isolation and Identification of Anthocyanins from Purple Sweet Potatoes

  • Lee, Lan-Sook;Chang, Eun-Ju;Rhim, Jong-Whan;Ko, Byoung-Seob;Park, Sang-Won
    • Preventive Nutrition and Food Science
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    • v.2 no.2
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    • pp.83-88
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    • 1997
  • Anthocyanin pigments of purple sweet potato roots (Ipomoea batatas L.) were extracted with 0.5% TFA (Trifluoroacetic acid) in 95% EtOh, and further isolated an purified by Amberlite XAD-7 and ODS column chromatography, and final preparative HPLC. Among nine anthocyanins isolated, the structure of three major anthocyanins were identified as 3-O-(6-O-trans-caffeyl)-2-O-(6-O-trans-caffeylglucopyranosyl)-$\beta$-D-glucopyranosyl-5-O-($\beta$-D-glucopyranosyl)-peonidin, 3-O-(6-O-trans-caffeyl)-2-O-(6-O-trans-feruloyl-glucopyranosyl)-$\beta$-D-glucopyranosyl-5-O-($\beta$-D-glucopyranosyl)-peonidin, and 3-O-(6-O-trans-caffeyl)-2-O-(6-O-p-hydroxylbenzoylglucopyranosyl)-$\beta$-D-glucopyranosyl)-peonidin, by using UV-visible absorption spectra, $^1$H-NMR and FAB-MS analysis.

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Acid-Catalyzed Benzidine Rearrangement of Unsymmetrical Hydrazoaromatics

  • 박군하;박문규;조윤환
    • Bulletin of the Korean Chemical Society
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    • v.19 no.10
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    • pp.1090-1094
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    • 1998
  • Acid-catalyzed benzidine rearrangements of new unsymmetrical diazanes 1-3, prepared from the reduction of corresponding diazenes 4-6, were carried out in ethanolic solutions. The results are as follows; rearrangement of (3-carbomethoxyphenyl)(3-methoxyphenyl)diazane 1 gave 4,4'-diamino-2-carbomethoxy-2'-methoxybiphenyl 12 (p-benzidine type) in 71% and 10-amino-3-methoxyphenanthridin-6(5H)-one 13, 8-amino-3-methoxyphenanthridin-6(5H)-one 14 in 7.1% and 3.4%, respectively. Product 13 and 14 were formed by the condensation reaction of primarily formed o-benzidine and diphenyline type product, respectively. (5-Carbomethoxy-2-chlorophenyl)(4-methoxyphenyl)diazane 2 and (5-carbomethoxy-2-methylphenyl)(4-methoxyphenyl)diazane 3 underwent mainly disproportionations to give fission amines and corresponding diazenes in about 53% and 40% yields, respectively. The results obtained from the rearrangements of diazanes 1-3 indirectly indicated the importance of disproportionations to understand the benzidine rearrangements. The structures of benzidine rearrangement products were determined by usual NMR techniques such as DEPT, 2D H-H COSY, H-C COSY, 2D NOESY, and Gaussian function multiplication.

Antioxidative Activity of Prunus sargentii Outer Bark Extractives

  • Park, Se-Yeong;Bae, Young-Soo
    • Journal of the Korean Wood Science and Technology
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    • v.40 no.2
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    • pp.141-146
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    • 2012
  • The outer bark of Prunus sargentii was collected, air-dried and extracted with 70% aqueous acetone. Then it was successively partitioned with n-hexane, dichloromethane ($CH_2Cl_2$), ethyl acetate (EtOAc) and $H_2O$. From the EtOAc soluble fraction, four compounds were isolated by the repeated Sephadex LH-20 column chromatography. The isolated compounds were determined as (+)-catechin (1), (-)-epicatechin (2), taxifolin (3), and neosakuranin (4) by the spectroscopic analysis including $^1H$, $^{13}C$-NMR, and 2D-NMR spectrometers. The antioxidative activities on the isolated compounds and the separated fractions were evaluated by DPPH radical scavenging assay. The crude, EtOAc, and $H_2O$ soluble fractions indicated good antioxidative potential compared to the $CH_2Cl_2$ and n-hexane soluble fractions.

d10 Metal Complexes of a Tripodal Amine Ligand

  • Choi, Kyu-Seong;Kang, Dong-hyun;Lee, Ji-Eun;Seo, Joo-beom;Lee, Shim-Sung
    • Bulletin of the Korean Chemical Society
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    • v.27 no.5
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    • pp.747-750
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    • 2006
  • Research on tripodal complexes has grown in recent decades and has been subject of numerous reports.1-11 The reasons for this interest include their relevance to model functions of metalloenzymes1-3 and their potential applications in catalysis.13-17 The ligand system used most in this category has been tren, the tripodal tetraamine N(CH2CH2NH2)3, and its derivatives.4 The bz3tren is a versatile tetradentate ligand, known to form stable complexes not only with transition metals5-11 including Cu2+, Zn2+ and Co2+ but also anion species.12 However, only few results on the d10 metal complexes with bz3tren have been reported by us10 and others.6,7 As a part of on going efforts, we therefore focus our attention to extend other d10 system that includes heavy metal ions.