• Title/Summary/Keyword: diol

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Chemical Constituents of the Rhizomes of Sparganium stoloniferum (흑삼릉 근경의 성분)

  • 신수용;도상학;신국현
    • YAKHAK HOEJI
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    • v.44 no.4
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    • pp.334-339
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    • 2000
  • The present study was carried out to evaluate biologically active components of the rhizomes of Sparganium stoloniferum and to supply the preliminary data for the chemotaxonomy and the medicinal application. Extraction and systematic fractionation of the rhizomes by column chromatography led to the isolation of six compounds from ethylacetate and n-butanol soluble fractions. Elucidation of the chemical structures of these compounds by physicochemical and apectral analysis demonstrated that compound I,II ,III,IV,V and Ⅵ were $\beta$-sitosterol, $\beta$-sitosterol-3-$\beta$-D-glucuronopyranoside, 3- (4-hydroxyphenyl)-2-propenoic acid, sorbose, 1-O-$\beta$-D-glucopyranosyl-(2S, 3R, 4E, 8Z)-2-[(2(R)-hydroxyeicosanoyl)amido]-4,8-octadecadiene-1,3-diol, and $\beta$-sitosterol-3-O-$\beta$-D-glucopyranoside, respectively.

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The Effect of Diol Unit on the Thermal Properties of Copolyester (Diol Unit가 Copolyester의 열적 성질에 미치는 효과)

  • Lee, Sun-Hee;Shim, Mi-Ja;Kim, Sang-Wook
    • Applied Chemistry for Engineering
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    • v.3 no.3
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    • pp.464-470
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    • 1992
  • The copolyester was prepared by melt polycondensation varying the amount of ethylene glycol(EG) and pentanediol from terephthalic acid(TPA), EG and pentanediol isomers were. used as the third monomer. The chemical structure and the compositions of the copolyester were determined by nuclear magnetic resonance spectroscopy. Thermal properties were investigated with the aid of differential scanning calorimetry and thermogravimetric analyzer.

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Ruthenium Complex Catalyzed Syntehesis of Diamino Compounds from ${\alpha},{\omega}$-Diols and Secondary Amines

  • Keun-Tae Huh;Sang Chul Shim;Chll Hoon Doh
    • Bulletin of the Korean Chemical Society
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    • v.11 no.1
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    • pp.45-49
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    • 1990
  • ${\alpha},{\omega}$-Diols react with secondary amines in the presence of a catalytic amount of ruthenium catalyst at $180^{\circ}C$ to give diamino compounds in good to excellent yields. The yield of diamino compound was affected by the molar ratio of ${\alpha},{\omega}$-diol to secondary amine. The reaction is affected by the nature of the phosphorus ligands employed and the effectiveness of the added ligand is completely different depending on the chain length of the ${\alpha},{\omega}$-diol. The reaction between ethylene glycol and primary amine in the presence of a catalytic amount of ruthenium catalyst gave 1,4-disubstituted piperazine.

Biodegradation Mechanism of Shogaol by Aspergillus niger (Aspergillus niger에 의한 Shogaol의 생분해 메카니즘)

  • 고인경;이상섭
    • YAKHAK HOEJI
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    • v.27 no.1
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    • pp.29-36
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    • 1983
  • Shogaol, one of the main pungent principles of the rhizome of Zingiber officinale, Roscoe, was biodegraded by Aspergillus niger to produce two main metabolites. The crystalline metabolite obtained after silicic acid column chromatography was proved to be 1-(4-hydroxy-3- methoxyphenyl)decan-10-ol-3-one. The oily metabolite obtained after prolonged fermentation was 1-(4-hydroxy-3-methoxyphenyl)-decan-3, 10-diol. The results suggest that shogaol should be biodegraded to 1-(4-hydroxy-3-methoxyphenyl)-dec-4-en-10-ol-3-one or to 1-(4-hydroxy-3-methoxyphenyl)-decan-3-one, and to 1-(4-hydroxy-3-methoxyphenyl)-decan-10-ol-3-one then to 1-(4-hydroxy-3-methoxyphenyl)-decan-3, 10-diol and finally to carbon dioxide and water.

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Synthesis of (E,E)-2,4-Dienols from (E)-$\beta$-Chloro-$\gamma$-hydroxy-vinylmercurials and Olefins by Palladium(Ⅱ) Salt

  • Kim, Jin-Il;Lee, Jong-Tae;Choi, Cheol-Kyu
    • Bulletin of the Korean Chemical Society
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    • v.7 no.3
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    • pp.235-237
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    • 1986
  • Reaction of $(E)-{\beta}-chloro-{\gamma}$-hydroxyvinylmercurials, prepared by mercuration of propargyl alcohol and 2-methyl-3-butyne-2-ol, with olefins in the presence of a catalytic amount of $Li_2PdCl_4$ and 2 equiv of cupric chloride in methanol at $50^{\circ}C$ gave the corresponding (E,E)-2,4-dienols in moderate yields. However, addition of 1 equiv of inorganic bases such as magnesium oxide to the reaction mixture brings a rapid and clean vinylation and gave high yields of the dienols at room temperature. In the case of hindered (E)-2-chloro-3-chloromercuri-2-buten-1,4-diol prepared from 2-butyne-1,4-diol, reaction with olefins gave the dienols only in low yields even in the presence of 2 equiv of magnesium oxide.

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.

Convenient Synthesis of Difurylmethanes and Dithienylmethanes and Their Application to the Syntheses of Core-Modified Porphyrins

  • 조원섭;이창희
    • Bulletin of the Korean Chemical Society
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    • v.19 no.3
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    • pp.314-319
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    • 1998
  • One flask synthesis of dithienylmethane and difurylmethane is reported. The reaction of aldehydes with excess furan or thiophene affords the meso-phenyldithienylmethane (DTM) and meso-phenyldifurylmethane (DFM), respectively. The reaction is catalyzed with trifluoroacetic acid or with BF3·O(Et)2. An acyl group is selectively introduced in 1 and 9 position of difurylmethane and dithienylmethane by use of an acid chloride and tin (IV) chloride. The reduction of resulting 1,9-bisacyldifurylmethane or 1,9-bisacyldithienylmethane affords the corresponding 1,9-bis-diol. An acid catalyzed condensation of diol with meso-phenyldipyrromethane followed by oxidation with DDQ gives the porphyrins. The reaction resulted meso-5,10,15,20-tetraphenyl-21,22-dithiaporphyrin (SSNN) or 15-mesityl-5,10,20-triphenyl-21,22-dioxaporphyrin (OONN), respectively. The formation of small amount of meso-tetraphenylporphyrin (TPPH2) is also observed. The formation of TPP indicates that meso-phenyldipyrromethane is reversibly cleaved and form pyrrole and pyrrylbenzylcarbocation during the condensation. The proton nmr and electronic spectrum of the SSNN and OONN porphyrins are somewhat different from the previously synthesized meso-5,10,15,20-tetraphenyl-21,23-dithiaporphyrin (SNSN) or meso-5,10,15,20-tetraphenyl-21,23-dioxaporphyrin (ONON).

New Crown Compounds Derived from 1,2-Bis(2-hydroxybenzyl)benzene (II) : Bisaryl Crowns

  • Lee, Woo-Young;Jung, Jae-Do;Park, Chang-Hee;Sim, Won-Bo;Park, Oee-Sook
    • Bulletin of the Korean Chemical Society
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    • v.11 no.4
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    • pp.350-354
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    • 1990
  • New bisaryl corands (crown ethers) bearing 1,2-dibenzyl- and 1,2-dibenzoylbenzene subunits have been synthesized: The reaction of 1,2-bis(2-hydroxybenzyl)benzene in base with mono-tetrahydropyranyl oligoethylene glycol tosylate, deprotection of the bis-condensation product to give a corresponding diol, tosylation of the free hydroxyls of the diol, and condensation of the ditosylate in base with 1,2-bis(2-hydroxybenzyl)benzene afforded a new type of bisaryl corand(Ⅰ) of 1,2-dibenzyl-benazene system. Oxidation of the benzylic positions of the corands (Ⅰ) furnished novel aromatic corands(Ⅱ) containing partly carbonyl functions.

13(E)-Labd-13-ene-8$\alpha$, 15-diol isolated from Brachyglottis monroi Induces Apoptosis on Human Breast Cancer MDA-MB231 cell line

  • Lim, Jin-A;Lee, Jeong-Ho;Lee, In-A;Nigel, B;Baek, Seung-Hwa
    • Proceedings of the PSK Conference
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    • 2003.04a
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    • pp.141.1-141.1
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    • 2003
  • The inhibitory effect of 13(E)-Labd-13-ene-8$\alpha$ 15-diol(1), isolated from the ethanol extract of Brachyglottis monroi, on the proliferation of human breast cancer MDA-MB231 cells was examined. Compound (1) at concentration as high as 16$\mu$/$m\ell$ has inhibited the proliferation of MDA-MB231 and this cytotoxic effect was increased in a time and dose-dependent manners. (omitted)

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The Cytotoxic Activity of 13(E)-Labd-13-ene-8$\alpha$, 15-diol from Brachyglottis monroi

  • Lim, Jin-A;Kwag, Jung-Sook;Nigel, B.Perry;Baek, Seung-Hwa
    • Proceedings of the PSK Conference
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    • 2003.04a
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    • pp.179.2-179.2
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    • 2003
  • The cytotoxic activity of 13(E)-Labd-13-ene-8$\alpha$, 15-diol(1), isolated from the ethanol extract of Brachyglottis monroi was evaluated against tumor cell lines such as P388, SNU-C4 MDA-MB231, B 16 melanoma and A549 in vitro. By mean of spectral analysis particularly by the aid of various two dimensional NMR experiments, 1H-NMR and 13C-NMR signals of (1) was completely assigned, and thus the structure of (1) was established unambiguously. (omitted)

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