• Title/Summary/Keyword: H-H COSY

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The flavone glycosides of Sasa borealis (조릿대잎의 flavone 배당체 성분)

  • Yoon, Ki-Dong;Kim, Chul-Young;Huh, Hoon
    • Korean Journal of Pharmacognosy
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    • v.31 no.2
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    • pp.224-227
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    • 2000
  • As part of study of the constituents of bamboo grasses, the leaves of Sasa borealis (Hackel) Makino (Gramineae) were examined. Friedelin, glutinol, isoorientin and isovitexin have been reported as constituents of bamboo grasses. In this study, tricin and two flavone glycosides, tricin $7-O-{\beta}-D-glucopyranoside$ and luteolin $6-C-{\alpha}-L-arabinopyranoside$ have been isolated from EtOAc extract of S. borealis, by consecutive silica gel, Sephadex LH-20 column chromatography and a repetitive HPLC. The structures of these compounds were determined by IR, $^1H-NMR,\;^{13}C-NMR,\;^{13}C-^1H\;COSY,\;^1H-^1H\;COSY,\;HMBC$ and Mass spectral data.

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Isolation of Isoamberboin and Isolipidiol from Whole Plants of Youngia japonica (L.) DC. (뽀리뱅이 전초로부터 Isoamberboin과 Isolipidiol의 분리)

  • Jang, Dae-Sik;Ha, Tae-Joung;Choi, Sang-Uk;Nam, Sang-Hae;Park, Ki-Hun;Yang, Min-Suk
    • Korean Journal of Pharmacognosy
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    • v.31 no.3
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    • pp.306-309
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    • 2000
  • Two sesquiterpene lactones were isolated from methanol extracts of the whole plants of Youngia japonica (L.) DC. by the silica gel column chromatography and recrystallization. On the basis of spectrometric studies including $^1H-NMR,\;^{13}C-NMR,\;DEPT,\;^1H-^1H\;COSY,\;^{13}C-^1H\;COSY$, IR and MS, compounds 1 and 2 were identified as derivatives of 10(14)-guaien-12, 6-olide, isoamberboin and isolipidiol, respectively. This is the first report on the isolation of isoamberboin and isolipidiol from Youngia japonica (L.) DC.

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Germacranolides from Flowers of Chrysanthemum boreale Makino (산국 꽃의 Germacranolides)

  • Jang, Dae-Sik;Park, Ki-Hun;Yang, Min-Suk
    • Korean Journal of Pharmacognosy
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    • v.29 no.2
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    • pp.67-70
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    • 1998
  • Two sesquiterpene lactones were isolated from the flowers of Chrysanthemum boreale Makino by the silica gel column chromatography and recrystallization. On the basis of spectrometric studies including $^1H-NMR,\;^{13}C-NMR,\;DEPT,\;^1H-^1H\;COSY,\;{13}C-^1H\;COSY$, IR and Mass, compounds 1 and 2 were identified as germacranolide, tulipinolide and costunolide, respectively. And they showed antibacterial activity against Vibrio parahaemolyticus, Bacillus subtilis, Bacillus cereus and Staphylococcus aureus. This is the first report that Chrysanthemum boreale contained tulipinolide and costunolide.

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Antibacterial Substances of the Flower of Chrysanthemum zawadskii Herbich var. latilobum Kitamura (구절초 꽃의 항균성 물질)

  • Jang, Dae-Sik;Park, Ki-Hun;Choi, Sang-Uk;Nam, Sang-Hae;Yang, Min-Suk
    • Applied Biological Chemistry
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    • v.40 no.1
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    • pp.85-88
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    • 1997
  • In orther to isolate antibacterial substances from the flower of Chrysanthemum zawadskii Herbich var. latilobum Kitam., the chloroform fraction was fractionated according to the activity against B. subtilis, S. aureus and V. parahaemolyticus. Two antibacterial substances were isolated and purified by preparative TLC and recrystallization. Compound I showed activity against all the tested bacteria and compound II exhibited the activity against B. subtilis and v. parahaemolyticus except S. aureus. Compared to benzoic acid and sorbic acid which are being used as food preservatives, compounds I and II showed about five-fold stronger antibacterial activity against B. subtilis and V. parahaemolyticus. On the basis of spectrometric studies including $^1H-NMR,\;^{13}C-NMR,\;DEPT,\;^1H-^1H\;COSY,\;^{13}C-^1H\;COSY$ and Mass, compounds I and II were identified as angeloylcumambrin B and cumambrin A, respectively. This is the first report of the isolation of angeloylcumambrin B and cumambrin A from this plant.

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Purification and characterization of antifungal compounds produced by Bacillus subtilis KS1 (Bacillus subtilis KS1이 생산하는 항진균물질의 정제 및 특성)

  • Ryoo, Sung-Woo;Maeng, Hack-Young;Maeng, Pil-Jae
    • The Korean Journal of Mycology
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    • v.24 no.4 s.79
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    • pp.293-304
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    • 1996
  • A bacterial strain, KSl, possessing strong antifungal activity was isolated from soil samples of ginseng fields and identified as Bacillus subtilis. In greenhouse test, the culture filtrate of B. subtilis KS1 showed strong protective effect against several fungal diseases of agricultural plants such as cucumber gray mold and wheat leaf rust. In addition, the crude butanol fraction of the culture filtrate exhibited antagonistic effect against several fungi including plant or human pathogens, such as Botrytis maydis, Chytridium lagenarium and Candida albicans. The antifungal compound, SW1, produced by B. subtilis KS1 was purified through consecutive chromatographic separations on a pep-RPC column and a ${\mu}$ Bondapak $C_{18}$ reverse phase column. Temperature and pH showed little effect on the stability of the compound in the ranges $-20-121^{\circ}C$ and pH 4.0-10.0, respectively. The composition and structural characteristics of SW1 were analysed by HPLC and by $^1H-,\;^1H-^1H-COSY$, NOESY, COSY-NOESY and HOHAHA NMR spectroscopy, respectively, which revealed that the compound belongs to iturin A, a typical cyclic antifungal compound produced by B. subtilis. In contrast to the previously reported iturin A compounds which have one or no $-CH_3$ side chain in the hydrophobic hydrocarbon chain of ${\beta}-amino$ acids, SW1 was shown to have a ${\beta}-amino$ acid containing 12-carbon skeleton with two $-CH_3$ side chains.

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Structural Analysis of Major Antimicrobial Substance Obtained from Leaf Mustard(Brassica juncea) (갓(Brassica juncea)의 주 항균물질의 구조 분석)

  • 강성구
    • Journal of the Korean Society of Food Science and Nutrition
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    • v.24 no.5
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    • pp.702-706
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    • 1995
  • A major component(compound A) in the ethylacetate fraction exhibited a strong antimicrobial activity was identified by UV, IR, FABMS and NMR. The compound A showed strong absorbance at 209, 259 and 359nm, indicating a flavonoid ring structure. IR spectrum possessed absorbance of OH at 3400∼3300cm-1, ketone at around 1650cm-1, and aromatic C=C at around 1660cm-1. Molecular weight of the compound A calculated as 478 from the information of m/z 479(M+H)+ and m/z 477(M-H)+ in the FABMS spectrum. Molecular formula of this compound was found to be C22H22O12 from m/z 479.1220(+3.1mmu for C22H23O12) of HRFABMS spectrum and from 13C-NMR spectrum. 1H-NMR and 13C-NMR spectra of the compound A revealed aromatic proton and benzene rings. Distortionless enhancement by polarization transfer(DEPT) exhibited that the compound A possessed 10 quaternary carbons and 3 substituted benzene rings including a methoxy group substitution. The compound A was identified as isorhamnetin 3-O-β-glucopyranoside by spectrophotometric methods in conjunction with 1H-1H COSY, 1H-13C COSY and HMBC, which revealed a flavone with OH group at 3, 5, 7, and 4' and methoxy group at 3' positions esterified to glucose.

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Isolation and Structure Determination of Two Furanosesquiterpenes from the Soft Coral Sinularia lochmodes (산호로부터 2개의 푸란노세스키테르펜의 분리와 구조 결정)

  • Park, Seon Gu;Paul J. Scheuer
    • Journal of the Korean Chemical Society
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    • v.38 no.10
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    • pp.749-752
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    • 1994
  • Two furanosesquiterpenes, (5'E)-5-(2',6'-dimethylocta-5',7'-dienyl) furan-3-carboxylic acid (1) and (1'E,5'E)-5-(2',6'-dimethylocta-l',5',7'-trienyl) furan-3-carboxylic acid (2), were isolated from soft coral Sinularia lochmodes collected from Palikir pass at Pohnpei Micronesia, June, 1990 in Hawaii. Their structures were elucidated by $^1H$, $^{13}C$ NMR, Homo-COSY, $^1H$-$^{13}C$ (1 bond) Heteronuclear Multiple Quantum Coherence Spectroscopy (HMQC), $^1H$-$^{13}C$ (2 and 3 bond) Heteronuclear Multiple Bond Coherence Spectroscopy (HMBC), Electron Impact Mass Spectroscopy (EI-ms), and Infrared Spectroscopy (IR).

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Isolation of Dineolignans, Saucernetin-7 and -8, with Nitric Oxide Inhibitory Activity and NMR assignment from Saururus chinensis

  • Lee, Kyung-Tae;Jung, Hyun-Ju;Park, Hee-Juhn
    • Korean Journal of Plant Resources
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    • v.19 no.6
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    • pp.655-659
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    • 2006
  • Two dineolignans (1,2) with nitric oxide inhibitory activities were isolated from Saururus chinensis (Saururaceae) using silica gel column chromatography. Although the structures, saucernetin-7 (1) and -8 (2), have been already reported, NMR assignment of the two compounds was completed aided by 2D-NMR spectroscopy including $^1H-^1H$ COSY, $^1H-^{13}C$ COSY, HMBC and NOESY NMR spectra. Compounds 1 and 2 exhibited significant nitride oxide inhibitory activity in LPS-induced RAW 264.7 cells with $IC_{50}$ values of $11.3{\mu}M\;and\;7.1{\mu}M$, respectively.

Structural Analogues of Cumambrin B from the Flower of Chrysanthemum boreale

  • Jang, Dae-Sik;Yang, Min-Suk;Ha, Tae-Jung;Park, Ki-Hun
    • Archives of Pharmacal Research
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    • v.21 no.5
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    • pp.591-594
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    • 1998
  • The structural analogues of cumambrin B(1, 2, 3, 4) were isolated from the flower of Chrysnathemum boreale Makino. The structures of compounds were determined by two-dimensional $^{1}H-^{1}H$ COSY and $^{13}C-^{1}H$ COSY spectra with the aid of homonuclear and heteronuclear double resonance experiment. The stereochemistry of compounds has been verified from single crystal X-ray diffraction of cumambrin A(2). the antimicrobial activities of these guaianolides have been studied.

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Intramolecualr cyclization of a dipyrromethane by an electrophilic aromatic substitution reaction producing a new chiral compound

  • Kim, Seung Hyun;Kim, Sung Kuk
    • Journal of the Korean Magnetic Resonance Society
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    • v.22 no.4
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    • pp.115-118
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    • 2018
  • Dipyrromethane 2 functionalized with 3-chloropropyl group on the meso carbon undergoes an unusual intramolecular electrophilic aromatic substitution reaction in the presence of $NaN_3$ instead of a simple nucleophilic substitution reaction. As a result, a new chiral dipyrromethane 1 was synthesized. In this reaction, the ${\beta}$-carbon of the pyrrole ring functions as a nucleophile while the carbon next to the chlorine atom acts as an electrophile. Interestingly, this reaction progresses even in the absence of an acid catalyst. Compound 1 was fully characterized by $^1H-^1H$ and $^1H-^{13}C$ COSY NMR spectroscopic analyses and the high resolution EI mass spectrometry.