• Journal of Ginseng Research
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• v.20 no.1
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• pp.30-35
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• 1996

Some polyacetylenes were Isolated from the rhizome of Korean red ginseng through re - pealed column chromatogrphy, and identified as 3-hydroxy-1, 9-heptadecadiene-4, 6-diyne (panaxynol), 9, 10-epoxy-3-hydroxy-1-heptadecene-4, 6-diane(panaxydol), 3, 9, 10-trihydroxy-1-heptadecene-4, 6-diyne(panaxytriol), 9, 10-epoxy-3-hydroxy-1, 16-heptadecadiene-4, 6-diyne(ginsenoyne A) and 10-ch1oro-3, 9-dihydroxy-1-heptadecene-4, 6-diane(panaxydol chlorohydrine) by several spectral and chemical methods.

• Bulletin of the Korean Chemical Society
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• v.20 no.6
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• pp.677-682
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• 1999

Conjugated polycarbosilanes with diacetylene and aromatic groups of thiophene or phenylene simultaneously present in the polymer backbone such as poly[[1,4-bis(thiophenyl)buta-1,3-diyne]-alt-(dimethylsilane)], poly[[1,4-bis(thiophenyl)buta-1,3-diyne]-alt-(diphenylsilane)], poly[[1,4-bis(phenyl)buta-1,3-diyne]-alt-(dimethylsilane)],and poly[[1,4-bis(phenyl)buta-1,3-diyne]-alt-(diphenylsilane)] have been prepared. The characteristic C=C stretching frequencies appear at 2177-2179㎝-1 in the IR spectra of the polymers. The molecular weights of these polymers were detemined by GPC. All of these materials are soluble in organic solvents such as THF and chloroform, and thermally stable up to 200℃ in general without any weight loss under nitrogen. The prepared materials in THF solvent show a maximum absorption peak in the range of 334-356 nm with a molar absorptivity of 10³∼10ⁿ(n=5)L/(cm·mol) in the UV-visible absorption spectra. A maximum emission peak in the range of 403-550 nm is also observed in the fluorescence emission spectra. Both absorption and emission spectra strongly indicate that the obtained polycarbosilanes contain the new conjugated systems along the polymer main chain.

• Archives of Pharmacal Research
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• v.12 no.1
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• pp.48-51
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• 1989

A new polyacetylene compound with cytotoxic activity against L1210 cells having diyne-ene and epoxy moiety, named panaxyne epoxide, was isolated from Panax ginseng C.A. Meyer. The chemical structure of the polyacetylene was determined to be tetradeca-13-ene-1,3-diyne-6,7-epoxide by UV, IR, $^1H-NMR,\;^{l3}$C-NMR and mass spectra.

• Natural Product Sciences
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• v.14 no.3
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• pp.177-181
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• 2008

Five polyacetylenes, ginsenoyne K (1), (Z)-1-methoxyheptadeca-9-en-4,6-diyne-3-one (2), panaxydol (3), panaxydiol (4), and (E)-heptadeca-8-en-4,6-diyne-3,10-diol (5) were isolated from the adventitious roots of Panax ginseng and their chemical structurFive polyacetylenes, ginsenoyne K (1), (Z)-1-methoxyheptadeca-9-en-4,6-diyne-3-one (2), panaxydol (3), panaxydiol (4), and (E)-heptadeca-8-en-4,6-diyne-3,10-diol (5) were isolated from the adventitious roots of Panax ginseng and their chemical structures were elucidated by interpretation of spectroscopic data. Among the isolated compounds, compounds 2 and 5 were reported for the first time as a natural product. Ginsenoyne K (1) showed dose-dependent inhibitory effect on dopa oxidase activity of tyrosinase.es were elucidated by interpretation of spectroscopic data. Among the isolated compounds, compounds 2 and 5 were reported for the first time as a natural product. Ginsenoyne K (1) showed dose-dependent inhibitory effect on dopa oxidase activity of tyrosinase.

• Korean Journal of Pharmacognosy
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• v.20 no.2
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• pp.71-75
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• 1989

A new polyyne, panaxyne, was isolated from the Korean red ginseng. The structure was determined as tetradeca-13-ene-1, 3-diyne-6, 7-diol by comparison of spectral data. The $ED_{50}\;value$ of panaxyne as cytotoxicity against L1210 cell was $11.0\;{\mu}g/ml$. The lower cytotoxic activity of the substance relative to other ginseng polyynes is presumably due to lack of the essential structural part of hept-1-en-4, 6-diyne-3-ol.

• Journal of Photoscience
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• v.1 no.2
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• pp.119-122
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• 1994

$PdCI_2(PPh_3)_2$-catalyzed photolysis of 1-phenyl-4-(pentamethyldisilanyl)buta-1,3-diyne (1) in dry benzene gives 1,4-disilacyclohexa-2,5-diene type dimerization products(3-6) via silacyclopropene. The silacyclopropene is formed from the singlet excited state of 1 and this silacyclopropene reacts with $(PPh_3)_2Pd^0$to form palladasilacyclobutene. In this reaction, the silylene-palladium complex is generated and reacts with 1 to give another silacyclopropene. $PdCI_2(PPh_3)_2$catalyzed photolysis of 1 with other alkynes supports the involvement of this silylene complex.

• Bulletin of the Korean Chemical Society
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• v.7 no.3
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• pp.179-182
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• 1986

A major polyacetylene compound from Panax ginseng roots, heptadeca-1-en-4,6-diyn-3,9,10-triol, was irradiated with 300 nm UV light to obtain a photooxidized acetylenic compound having the conjugated en-on-diyne chromophore, heptadeca-1-en-4,6-diyn-9,10-diol-3-one. The same oxidation product was obtained exclusively by 4-(dimethylamino) pyridinium chlorochromate at room temperature.

• Korean Journal of Plant Resources
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• v.27 no.3
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• pp.215-222
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• 2014

This study was conducted to isolate a compound with anticancer properties from the roots of Peucedanum japonicum Thunb. (Umbelliferae), and to evaluate the efficacy of that compound's anticancer activity. The $CHCl_3$ layer was purified via repeated column chromatography and recrystallization. The two compounds isolated from $CHCl_3$ layer were identified via NMR spectroscopic analysis as (10E) 1,10-heptadecadiene-4,6-diyne-3,8,9-triol (Comp. I) and anomalin (Comp. II). (10E) 1,10-heptadecadiene-4,6-diyne-3,8,9-triol was the first report from the roots of P. japonicum. MTT assays were conducted to evaluate the in vitro cytotoxic activities of Compounds I and II against the following human cancer cell lines: HeLa, HepG2, SNU-16, and AGS. Comp. I evidenced the most profound cytotoxic activity against HepG2 cells ($IC_{50}=6.04{\mu}g/mL$), and Comp. II exhibited the most profound cytotoxic activity against SNU-16 cells ($IC_{50}=18.24{\mu}g/mL$) among the human cancer cell lines tested in this study. However, no significant cell death was observed in the CCD-25Lu human normal lung fibroblast cells. Quantitative analysis using UPLC (Ultra Performance Liquid Chromatography) showed that the roots of P. japonicum contained 0.015 (Comp. I) and 1.69 mg/g (Comp. II) of these compounds.

• Korean Journal of Crystallography
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• v.6 no.1
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• pp.36-42
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• 1995

Two types of single crystals of the title compound [6-(2-pyridyl)-3, 5-hexadiyn-ol, PyHxD] were obtained by solution of n-hexane/CH2C12 and n-hexane/Et2O, and their molecular conformations are proved identical in spite of different of space groups; C22H18N2O2 (I), Mr=343.70, Monoclinic, Pa, a=14.595(2), b=5.413(2), c=12.218(2)Å, β=96.86(1)°, V=958.3Å3, Z=2, Dx=1.19 Mgm-3, λ(MoKα)=0.71069Å, μ=0.072mm-1, F(000)=360.0, T=292K, R=0.104 for 756 unique observed reflections. An asymmetric unit contains a dimer connected by two N-H…O intermolecular hydrogen bonds. C11H9NO (II), Mr=171.85, Monoclinic, P21/a, a=14.611(2), b=5.423(6), c=12.191(2)Å, β=96.89(1)°, V=959.0Å3, Z=4, Dx=1.19 Mgm-3, λ(MoKα)=0.71069Å, μ=0.072mm-1, F(000)=360.0, T=293K, R=0.066 for 824 unique observed reflection. The structural asymmetric unit contains a molecule, but two N-H…O hydrogen bonds related by controsymmetry make the molecules form a dimer. In both structure, the dihedral angle between the planar pyridyl ring and the plane defined by C(10)-C(11)-O connected by linear diyne chain is approximately normal, and the molecules are stacked along b-axis with the unit repeat of b-axis.

• Bulletin of the Korean Chemical Society
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• v.4 no.4
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• pp.183-188
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• 1983

Two major and two minor polyacetylenes were isolated from fresh white Korean ginseng roots. The petroleum ether-ethyl ether fractions containing the polyacetylene compounds were collected through solvent fractionation, partition and silica gel column chromatography. Further separation of polyacetylenic fractions was proceeded by bonded normal phase HPLC utilizing a moderately nonpolar microparticulate column. The low pressure liquid chromatography was used for the semi-preparative separation. The chemical structures of the two major polyacetylenes separated were determined by UV, IR, $^1H$ NMR, $^{13}C$ NMR, mass spectra and elemental analysis. One of them is identified to be heptadeca-1-en-4, 6-diyne-3, 9, 10-triol, a new structure, and the other is heptadeca-1, 9-dien-4, 6-diyn-3-ol, known as panaxynol.