• Korean Journal of Food Science and Technology
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• 제22권5호
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• pp.549-554
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• 1990

Glycosidically bound fraction was separated from apricot by Amberlite XAD-2 adsorption and eluted with methanol. Aglycones were liberated from the bound fraction by enzymatic hydrolysis, acid hydrolysis or by means of simultaneous distillation-extraction at pH 3.0. A total of 40 components were identified in three bound volatile fractions. Besides linalool oxide, linalool. ${\alpha}-terpineol$, nerol, geraniol, benzyl alcohol and 2-phenylethyl alcohol, previously reported as glycosidically bound volatiles, the following components were identified for the first time as glycosidically bound volatiles in apricot: 2,6-dimethyl-3,7-octadiene-2,6-diol , 3.7-dimethyl-1,5-octadiene-3,7-diol, (E)- and (Z)-2.6-dimethyl-2,7-octadiene-1,6-diol, $3,4-didehydro-{\beta}-ionol,\;3-oxo-{\alpha}-ionol$, $3-hydroxy-7,8-dihydro-{\beta}-ionol,\;3-oxo-7,8-dihydro-{\alpha}-ionol ,\;3-hydroxy-{\beta}-ionone$, eugenol, 4-hydroxyethylphenyl acetate and 2,3-dihydrobenzofuran.

• Archives of Pharmacal Research
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• 제29권10호
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• pp.840-844
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• 2006

For the exploration of pharmacophoric moiety of malloapelta B (1) possessing the inhibitory activity of $NF-{\kappa}B$ activation, structural variation of ${\alpha},{\beta}-unsaturated$ carbonyl motif was attempted. 1 was reduced by catalytic hydrogenation, sodium borohydride, and lithium aluminumhydride. Catalytic hydrogenation with 30 psi or 15 psi of $H_2$ gas of 1 generated 8-butyl-5,7-dimethoxy-2,2-dimethylchroman (2) and 1-(5,7-dimethoxy-2,2-dimethylchroman-8-yl)butan-1-one (3), respectively. Reduction with sodium borohydride occurred at the double bond of ${\alpha},{\beta}-unsaturated$ ketone of 1 to give 1-(5,7-dimethoxy-2,2-dimethyl-2H-chromen-8-yl)butan-1-one (4). Reduction of 1 with lithium aluminumhydride and then quenched with methanol and water produced unexpected products, 1-(5,7-dimethoxy-2,2-dimethyl-2H-chromen-8-yl)-3-methoxy-1-butene (5) and 1-(5,7-dimethoxy-2,2-dimethyl-2H-chromen-8-yl)-3-hydroxy-1-butene (6). These are formed from the isomerization of initial product 9 through the continuous conjugate carbocation intermediate 11. Addition of ethylmagnesium bromide and dimethyl malonate anion to 1 gave the conjugate adducts 7 and 8. Ethylmagesium bromide and sodium borohydride reduction unusually gave the conjugate addition due to steric congestion around carbonyl group of 1. Compound 2 exhibits the reduced inhibitory activity against $NF-{\kappa}B$ activation and the others do not show the activity. Therefore ${\alpha},{\beta}-unsaturated$ carbonyl group of 1 should be important for its inhibitory activity.

• Archives of Pharmacal Research
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• 제15권1호
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• pp.87-90
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• 1992

The syntheses of novel heterocyclic base modified pyrimidine nucleosides are described. 5, 6-dimethyl-4-hydroxy-3-methoxy-1-$(\beta$-D-ribofuranosyl)2(1H)-pyridinone 7 was synthesized by condensation of silylated 5, 6-dimethyl4-hydroxy-3-methoxy-2(1H)-pyridione 7 was synthesized by condensation of silylated 5, 6-dimethyl-4-hydroxy-3-methoxy-2(1H)-pyridinone with $\beta$-D-ribofuranose-1-acetate-2, 3, 5-tribenzoate in dichloroethane in the presence of Lewis acid followed by debenzoylation. The 2, 2'-anhydro-5, 6-dimethyl-2-hydroxy-3-methoxy-1-$\beta$-D-arabinofuranosyl-4-pyridinone 8 was obtained from the reaction of the free ribonucleoside 7 and diphenyl carbonate in DMF. None of these compounds showed any significant antiviral ad antitumor activities in vitro tests.

• Natural Product Sciences
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• 제18권2호
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• pp.97-101
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• 2012

Six lignan compounds, 1-(17,21-dihydroxyphenyl)-9-(12,13-dihydroxyphenyl)-1-nonanone (malabaricone C) (1), 7'-(3',4'-methylenedioxyphenyl)-8,8'-dimethyl-7-(3,4-dihydroxyphenyl)-butane (2), 7'-(3',4'-dimethoxyphenyl)-8,8'-dimethyl-7-(3-methoxy-4-hydroxyphenyl)-butane (3), 7-(4-hydroxy-3-methoxyphenyl)-7'-(3',4'-methylenedioxyphenyl)-8,8'-lignan-7-methyl ether (4), (+)-erythro-(7S,8R)-${\Delta}^{8^'}$-7-hydroxy-3,4,3',5'-tetramethoxy-8-O-4'-neolignan (5), and (+)-erythro-(7S,8R)-${\Delta}^{8^'}$-7-acetoxy-3,4,3',5'-tetramethoxy-8-O-4'-neolignan (6), were isolated from the seeds of Myristica fragrans. The chemical structures of these compounds were determined on the basis of spectroscopic analyses including 2D NMR. Compounds 1 - 6 were evaluated for their cytotoxic activity against the HL-60, MCF-7, and A549 cancer cell lines in in vitro.

• Bulletin of the Korean Chemical Society
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• 제21권8호
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• pp.797-800
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• 2000

The reaction of o-acylthiophenacyl chloride 5a with onc equivalent ofsodium azide in aqueous acetone at-10~ $-5^{\circ}C$ gave 2,9-dimethyl-6H,I3H-dibenzo[d,i][1,6]dithiecin-7,14-dione 7(10%),acyclic dimer 8(64%),and tri-mer 9 (8%). Dimer 8 and trimer 9 we re converted readily to 7 under the similar conditions at room temperature in yields of 72% and 53%,respectivel. Also, one pot synthesis of 7 (64%, 45%) from the reaction of 5a or 5b with two equivalents of sodium azide at room temperature was very successful.

• Archives of Pharmacal Research
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• 제22권5호
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• pp.502-506
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• 1999

Different 2-(8,12 dimethyl-5-oxa-7(E), 11-tridecadienyl)-alkyl phenyl ethers, their mono oxirane and thirane derivatives were synthesized and tested on Culex pipiens quinquefasciatus Say for their juvenile hormone activity.

• Korean Journal of Pharmacognosy
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• 제39권2호
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• pp.86-90
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• 2008

Two decursin derivatives were synthesized from decursinol. Compounds 1 and 2 were determined as 7-{3-[4-(2-Methoxy-phenyl)-piperazin-1-yl]-propoxy}-8,8-dimethyl-7,8-dihydro-6H-pyranochromen-2-one (1) and decursinol 3'-O-E-pmethoxycinnamic acid ester (2), respectively and newly reported. Compounds 1 and 2 significantly inhibited AChE activity and ameliorated memory impairment induced in mice by scopolamine (1.0 mg/kg body weight s.c.) as measured in passive avoidance test. We suggest, therefore, that compounds 1 and 2 has both anti-AChE and anti-amnesic activities that may ultimately hold significant therapeutic value in alleviating certain memory impairment observed in Alzheimer's disease.

• Archives of Pharmacal Research
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• 제13권3호
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• pp.257-260
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• 1990

Hantzch's type reaction of methyl acetopyruvate (2a), methyl 3-aminocrotonate (3) and 3-nitrobenzaldehyde (4) led to dimethyl 3-acetyl-6-methyl-4-(3'-nitrophenyl)-2, 5-dicarboxylate (5a) and methyl 2, 6-dimethyl-5-(1', 2'-dioxo-2'-methoxyethyl)-4-(3' nitrophenyl)- 2, 5-dicarboxylate (5a) and methyl 2, 6-dimethyl-5-(1', 2'-dioxo-2'methoxyethyl_4-(3' nitrophenyl)1, 4-dihydropyridine-3-carboxylate (6a) in 26.7 and 9.2% yield, respectively. On the other hand, methyl 2, 60dimethyl-4-(3'-nitrophenyl)-1, 4-dihydropyridine 3-carboxylate (9) was acylated by ethyl oxaly chloride to give methyl 2, 6-dimethyl-5-(1', 2'-dioxo-2'-ethoxyethyl)-4-(3'-nitrophenyl)-a, 4-dihydropyridine-3-carboxylate (6b) in 76.8% yield.

• Korean Journal of Food Science and Technology
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• 제20권4호
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• pp.606-612
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• 1988

The volatile flavor compounds of fresh and dried shiitake mushrooms(Lentinus edodes) were extracted by simultaneous steam distillation-extraction apparatus, and analyzed by combined GC and GC-MS, and effects of pH on the formation of volatile compounds in fresh shiitake mushroom were investigated. Of the 29 compounds identified from fresh shiitake mushroom, the main volatile compound was 1-octen-3-ol comprising about 74.7% of the total volatiles and that in dried shiitake mushroom was 1, 2, 4-trithiolane comprising about 66.3%. With the exception of above two compounds, 3-octanone, 1-octen-3-one, 3-octanol, cis-2-octenal, n-octanol and cis-2-octenol as $C_8$ compounds were identified. Carbon disulfide, dimethyl disulfide, dimethyl trisulfide, 1-(methyl thio)-dimethyl disulfide, 1, 2, 4, 5-tetrathiane as sulfurous compounds were also identified. The formation of $C_8$ compounds in fresh shiitake mushroom during immersion was dominant in the range of pH 6.0 to 7.0, while the formation of sulfurous compounds in the range of pH 8.0 to 9.0.

• Korean Chemical Engineering Research
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• 제54권4호
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• pp.555-559
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• 2016

In this study, new platinum complexes were synthesized utilizing the ligand of a 2,2'-bispyrimidine (bpim), 2,2'-bipyridine (bpy), 5,5'-dimethyl-2,2'-bipyridine (5,5-mebpy), 5'-bromo-2,2'-bipyridine (5-brbpy), 5,5'-dibromo-2,2'-bipyridine (5,5-brbpy), 4,4'-dimethyl-2,2'-bipyridine (4,4-mebpy), 4,4'-dihexyl-2,2'-Bipyridine (4,4-hebpy), 1,10'-Phenanthroline (phen), 3,4,7,8'-tetramethyl-1,10'-Phenanthroline (3,4,7,8-phen). In order to determine chemical structure of Synthesized platinum complexes, $^1H(^{13}C)$-NMR, UV-vis and FT-IR were used and optical physics and chemical properties were measured PL. In the case of platinum complexes, wavelength has been identified 356~421 nm. Quantum efficiency in DMSO solution was appeared 0.05~0.46.