• Title/Summary/Keyword: H-H COSY

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The Solubilization Site of Some Phenyl Alkanols in Aqueous Sodium Dodecylsulfate Micelle (몇가지 페닐 알카놀의 Sodium Dodeylsulfate 수용액 미셀내에서의 가용화 위치)

  • Jeong, Jong Jae;Gang, Jeong Bu;Lee, Gyeong Hui
    • Journal of the Korean Chemical Society
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    • v.38 no.3
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    • pp.194-199
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    • 1994
  • The solubilization sites of some phenyl alkanols such as phenol, benzyl alcohol, phenethyl alcohol, 3-phenyl-1-propanol solubilized in 0.2 M aqueous sodium dodecylsulfate micelle solution was studied by two dimensional heteronuclear correlation spectroscopy (2D C-H COSY). The results show more quantitative and clear solubilization sites in the SDS micelle than previous results using $^1H$-NMR spectrum integration. We found that most of the phenyl alkanols penetrate into the core of SDS micelle, and the insertion depth was 6.5∼7.0 methylene units from ${\alpha}$-methylene.

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Constituents of the Herb of Isodon excisus var. coreanus

  • Kim, Ho-Kyoung;Whang, Wan-Kyunn;Kim, Il-Hyuk
    • Archives of Pharmacal Research
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    • v.20 no.3
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    • pp.291-296
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    • 1997
  • The studies were carried out to evaluate the constituents in the aerial part of Isodon excisus var. coreanus (Labiatae). From the aqueous fraction of methanol extract, compound I (${\alpha}$-[[3-(3, 4-dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-3,4-dihydroxy-benzenepropanoic acid), compound II (9-methyl-dihydroferulic acid-4-O-.betha.-D-glucopyranosyl $(1{\rightarrow}2)$-${\alpha}$-L- rhamnopyranosyl (1.rarw.4)-.betha.-D-glucopyranoside), compound III (ent-7.alpha., 11${\alpha}$,15.betha.-trihydroxy-kaur-16-en-1-O-.betha.-D-glucopyranoside) and compound IV ($2{\alpha}$,3${\beta}$,$7{\alpha}$,23-tetrahydroxy-olean-12 -en-28-oic acid 28-O-${\beta}$-D-glucopyranoside) were isolated and identified on the basis of their physicochemical and spectroscopic evidences[IR, FAB(-)MS,$^{1}H-NMR,$$^{13}C-NMR,$$ HMQC$$^{1}H-^{1}H $COSY and HMBC (Heteronuclear Multiple Bond Connectivity)]. Especially, New compounds II and III were named Isodonin A and Isodonin B respectively.

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[$^1H-NMR$ Assignment of HIV Protease Inhibitor, Procyanidin B3 isolated from Rosa rugosa

  • Park, Jong-Cheol;Ito, Hideyuki;Yoshida, Takashi
    • Natural Product Sciences
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    • v.9 no.2
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    • pp.49-51
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    • 2003
  • The underground part of Rosa rugosa Thunb. has been used in Korean folk medicine for treating diabetes. The $^{1}H-NMR$ signal of procyanidin B3 isolated from Rosa rugosa was fully assigned by utilizing $^{1}H-^{1}H$ COSY. Procyandin B3 showed a moderate inhibitory activity against HIV-1 protease.

Antagonism and Structural Identification of Antifungal Compound from Chaetomium cochliodes against Phytopathogenic Fungi

  • Kang, Jae Gon;Kim, Keun Ki;Kang, Kyu Young
    • Journal of Applied Biological Chemistry
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    • v.42 no.3
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    • pp.146-150
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    • 1999
  • As a part of the integrated disease system in greenhouse, an antifungal fungus(AF1) was isolated from greenhouse soil. It exhibited strong inhibitory activites against Pythium ultimum, Phytophtora capsici, Rhizoctonia solani, Botrytis cinerea, and Fusarium oxysporum based on dual culture on 1/5 strength of potato dextrose agar between antagonistic fungus and several plant pathogens. The antagonistic fungus was identified as Chaetomium cochliodes, based on morphological characteristics; the body of the perithecium bears straight or slightly wavy, unbranched hairs, whilst the apex bears a group of spirally coiled hairs. To investigate antagonistic principles, antifungal compound was extracted and fractionated by different solvent systems. An antifungal compound was isolated as pure crystal from is culture filtrate using organic solvent extraction and column chromatography, followed by preparative thin layer chromatography. The chemical structure of the purified antifungal compound was identified as chaetoglobosin A based on the data obtained form $^1H-NMR$, $^{13}C-NMR$, DEPT 90, 135, $^1H-^1H$ COSY, $^1H-^{13}C$ COSY and EI/MS. $ED_{50}$ values of the chaetoglobosin A against P. ultimum, P. capsici, R. solani, B. cinerea and F. oxysporum were 1.98, 4.01, 4.16, 2.67 and 35.14 ppm, respectively.

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Constituents of Sanguisorba hakusanensis Leaves (산오이풀 잎의 성분)

  • Kwon, Won-Jun;Whang, Wan-Kyunn;Kim, Il-Hyuk
    • YAKHAK HOEJI
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    • v.40 no.3
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    • pp.262-272
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    • 1996
  • The constituents of Sanguisorba hakusanensis leaves (Rosaceae), of which the roots have been used as an astringent, hemostatics and antiphlogistics, were studied phytoche mically. From water fraction of the MeOH extract, gallic acid 3-O-${\beta}$-D-(6'-O-galloyl)-glucopyranoside(I), quercetin-3-O-${\beta$-D-galactopyranoside(II), quercetin-3-O-${\alpha}$-L-arabinopyranoside(III) and $2{\alpha},\;3{\beta},\;19{\alpha}$, 23-tetrahydroxyurs-12-en-28-oic acid 28-O-${\beta}$-D-glucopyranoside(IV) were isolated by column chromatographic separation using Amberlite XAD-2, ODS-gel and Sephadex LH-20. The structure of these compounds were elucidated by spectroscopic parameters of $^1H$-NMR, $^{13}C$-NMR, $^1H-^1H$ COSY, $^{13}C-^1H$ COSY, EI-Mass, FAB-Mass, IR, UV and by comparison with authentic samples.

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Evaluations of Spectral Analysis of in vitro 2D-COSY and 2D-NOESY on Human Brain Metabolites (인체 뇌 대사물질에서의 In vitro 2D-COSY와 2D-NOESY 스펙트럼 분석 평가)

  • Choe, Bo-Young;Woo, Dong-Cheol;Kim, Sang-Young;Choi, Chi-Bong;Lee, Sung-Im;Kim, Eun-Hee;Hong, Kwan-Soo;Jeon, Young-Ho;Cheong, Chae-Joon;Kim, Sang-Soo;Lim, Hyang-Sook
    • Investigative Magnetic Resonance Imaging
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    • v.12 no.1
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    • pp.8-19
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    • 2008
  • Purpose : To investigate the 3-bond and spatial connectivity of human brain metabolites by scalar coupling and dipolar nuclear Overhauser effect/enhancement (NOE) interaction through 2D- correlation spectroscopy (COSY) and 2D- NOE spectroscopy (NOESY) techniques. Materials and Methods : All 2D experiments were performed on Bruker Avance 500 (11.8 T) with the zshield gradient triple resonance cryoprobe at 298 K. Human brain metabolites were prepared with 10% $D_2O$. Two-dimensional spectra with 2048 data points contains 320 free induction decay (FID) averaging. Repetition delay was 2 sec. The Top Spin 2.0 software was used for post-processing. Total 7 metabolites such as N-acetyl aspartate (NAA), creatine (Cr), choline (Cho), lutamine (Gln), glutamate (Glu), myo-inositol (Ins), and lactate (Lac) were included for major target metabolites. Results : Symmetrical 2D-COSY and 2D-NOESY pectra were successfully acquired: COSY cross peaks were observed in the only 1.0-4.5 ppm, however, NOESY cross peaks were observed in the 1.0-4.5 ppm and 7.9 ppm. From the result of the 2-D COSY data, cross peaks between the methyl protons ($CH_3$(3)) at 1.33 ppm and methine proton (CH(2)) at 4.11 ppm were observed in Lac. Cross peaks between the methylene protons (CH2(3,$H{\alpha}$)) at 2.50ppm and methylene protons ($CH_2$,(3,$H_B$)) at 2.70 ppm were observed in NAA. Cross peaks between the methine proton (CH(5)) at 3.27 ppm and the methine proton (CH(4,6)) at 3.59 ppm, between the methine proton (CH(1,3)) at 3.53 ppm and methine proton (CH(4,6)) at 3.59 ppm, and between the methine proton (CH(1,3)) at 3.53 ppm and methine proton (CH(2)) at 4.05 ppm were observed in Ins. From the result of 2-D NOESY data, cross peaks between the NH proton at 8.00 ppm and methyl protons ($CH_3$) were observed in NAA. Cross peaks between the methyl protons ($CH_3$(3)) at 1.33 ppm and methine proton (CH(2)) at 4.11 ppm were observed in Lac. Cross peaks between the methyl protons (CH3) at 3.03 ppm and methylene protons (CH2) at 3.93 ppm were observed in Cr. Cross peaks between the methylene protons ($CH_2$(3)) at 2.11 ppm and methylene protons ($CH_2$(4)) at 2.35 ppm, and between the methylene protons($CH_2$ (3)) at 2.11 ppm and methine proton (CH(2)) at 3.76 ppm were observed in Glu. Cross peaks between the methylene protons (CH2 (3)) at 2.14 ppm and methine proton (CH(2)) at 3.79 ppm were observed in Gln. Cross peaks between the methine proton (CH(5)) at 3.27 ppm and the methine proton (CH(4,6)) at 3.59 ppm, and between the methine proton (CH(1,3)) at 3.53 ppm and methine proton (CH(2)) at 4.05 ppm were observed in Ins. Conclusion : The present study demonstrated that in vitro 2D-COSY and NOESY represented the 3-bond and spatial connectivity of human brain metabolites by scalar coupling and dipolar NOE interaction. This study could aid in better understanding the interactions between human brain metabolites in vivo 2DCOSY study.

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The constituents of taraxacum hallaisanensis roots

  • Yang, Deuk-Suk;Whang, Wan-Kyunn;Kim, Il-Hyuk
    • Archives of Pharmacal Research
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    • v.19 no.6
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    • pp.507-513
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    • 1996
  • Three sesquiterpene lactone compounds, two novel(1.betha.,3.betha.-dihydroxy-6.betha.,11.betha.,4.alpha.,5.alpha.,7.alpha.H -eudesm-12, 6-olide-1-O-.betha.-D-glucopyranoside, 1.betha.,3.betha.-dihydroxy-6.betha.,11.betha.,4.alpha.,5.alpha.,7.alpha.H-eudes m-12,6-olide-1-O-.betha.-D-glucopyranoside) and 1.betha.,3.betha.-dihydroxy-6.betha.,11.betha.,4.alpha.,5.alpha., 7.alpha.H-eudesm-12,6-olide were isolated from the aqueous fraction of MeOH extract of the roots from Taraxacum hallaisanensis (Compositae) employing Amberlite XAD-2, ODS-gel, silica gel and Sephadex LH-20 column chromatographics. Another known compound, (-)-epicatechin, was isolated from the aqueous fraction of the MeOH extract. The total MeOH extract also contained phytosterol and a mixture of .betha.-amyrin acetate, .alpha.-amyrin acetate and lupeol acetate. Structures of isolated compounds were elucidated by spectroscopic parameters of IR, Mass, /sup 13/C-NMR, /sup 1/H-NMR, /sup 1/H-/sup 1/H COSY, /sup 13/C-/sup 1/H COSY and HMBC.

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Studies on Chemical Structure Determination of Polygonatum sibiricum Extracts(I) (황정(黃精) 추출물의 화학구조 결정에 관한 연구(I))

  • 신동수;윤중호;박주희;권기락;안철진;주우홍;강진호;문병호
    • Journal of Life Science
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    • v.9 no.2
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    • pp.207-211
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    • 1999
  • Biologically active compounds in Polygonatum sibiricum were extracted using organic solvents as hexane, CHCl$_3$, n-butanol corresponding each component. Compound I was purified from hexane layer and the chemical structure of compound I was characterized using 1H-NMR, 13C-NMR, DEPT135, COSY, HMQC, HMBC spectrum and MS-spectrum. Consequently, the chemical structure of compound I was determined as 9,12-(9E,l2E)-octade cadienoic acid.

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Lignans from Myristica fragrans (육두구의 리그난 성분)

  • 김갑준;한용남
    • YAKHAK HOEJI
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    • v.46 no.2
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    • pp.98-101
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    • 2002
  • The phytochemical study of nutmeg, the seeds of Myristica fragrans Houttuyn (Myristicaceae) led to the isolation of three lignans, safrole (I), macelignan (III), and a 3,4 : 3',4'-bis(methylenedioxy)lignan (II). The compound II was identified by a mixture (1:1) of (8S, 8'R)- and (8S, 8'S)-forms of bis(3, 4-methylenedioxy)-8, 8'-neolignan by $^1$H-, $^{13}$ C-NMR and $^1$H-$^1$H COSY spectral data. The compound II was isolated for the first time from Myristica fragrans.

Identification of Salidroside from Rhodiola sachalinensis A. Bor. and its Production through Cell Suspension Culture (참돌꽃에서 Salidroside의 동정 및 현탁세포배양을 통한 분리)

  • Kim, Soo-Jung;Kim, Kwang-Soo;Hwang, Sung-Jin;Chon, Sang-Uk;Kim, Young-Ho;Ahn, Jun-Cheul;Hwang, Baik
    • Korean Journal of Medicinal Crop Science
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    • v.12 no.3
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    • pp.203-208
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    • 2004
  • Salidroside was isolated and purified from R. sachalinensis A. Bor. roots. Purified salidroside was obtained from repeated silicagel column chromatography and preparative HPLC, and identified by $^1H-NMR,\;^{13}C-NMR\;and\;^1H-^1H$ COSY spectra analyzer. Callus induction and cell suspension from R. sachalinensis leaf segments were established on 1/2MS solid medium and in $2B_5$ liquid medium containing 0.5 mg/l NAA and 1 mg/l, BA in the dark condition, respectively. The contents of salidroside for suspension culture were ranging from 0.12% to 0.41% in comparison with 0.17% for natural roots.