• Proceedings of the Korean Society of Applied Pharmacology
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• 1993.04a
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• pp.118-118
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• 1993

퀴놀론 모핵의 합성은 기존에 알려진 합성 방법인 Could-Jacobs방법과 Bayer방법에 의해서 Intermediate로 사용된 7-chloro-1-ethyl-6-fluoro-1, 4-dihydro-4-oxoquinoline-3-carboxylic acid와 1-cyclopropyl-7-chloro-6-Fluoro-1,4-dihydro-4-oxoquinolne-3-carboxylic acid를 합성하였다. Heteroaromatic tin compound는 furan, thiophene, 3-bromopyridine, 2-fluoropyridine에 n-BuLi을 사용하여 metallation 한후 electrophile로 tributyltin chloride를 사용하여 2-tributylstannofuran, 2-tributylst-annothiophene, 3-tributylstannopyridine, 2- fluoro-2-tributylstannop-yridine을 합성할 수 있었다. 이상의 Intermediate와 tin compounds를 p-alladium 촉매하에서 반응시켜 1-ethyl-7-(2-furanyl)-6-fluoro-1,4-dihy-dro-4-oxo-3-quinoline-carboxylic acid (compound 3), 1-ethyl-7-(2-th-iophenyl)-6-fluoro-1,4-dihydro-4-oxo-3-quinol in carboxylic acid(compound 5), 1-ethyl-7-(3-pyridinyl)-6-fluoro-1,4-dihydro-4-oxo-3-quinoline carboxylic acid (compound 7), 1-ethyl-7-(2-fluoro-3-pyrid-nyl)-6-fluoro-1,4-dihydro-4-oxo-3-quinoline carboxylic acid (compound 9), 1-cyclopropyl-7-(2-furanyl) -6-fluoro-1,4-dihydro-4-oxo-3-quinoline carboxylic acid (compound 4), 1-cyclopropyl-7-(2-thiophenyl)-6-fluoro-1,4-dihydro-4-oxo-3-quinoline carboxylic acid (compound 6) ,1-cyclopropyl-7-(3-pyridinyl)-6-fluoro-1,4-dihydro-4-oxo-3-quinoline carboxylic acid (compound 8), 1-cyclopropyl-7-(2-fluoro-3-pyridinyl)-6-fluoro-1,4-dihydro-4-oxo-3-quinoline carboxylic acid (compound 10)를 합성하였다.

• YAKHAK HOEJI
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• v.35 no.6
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• pp.483-485
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• 1991

A furanquinone substance(methyl 5-hydroxy-dinaphtho [1,2-2',3'] furan-7,12-dione-6-carboxylate) which has been isolated from the methanol extract of Paulownia tomentosa stem was synthesized by condensing 2,3-dichloro-1,4-naphthoquinone with methyl 1,4-dihydroxy-naphthalene-2-carboxylate in pyridine and identified by NMR, MS, UV, IR etc.

• Journal of Convergence for Information Technology
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• v.10 no.11
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• pp.177-184
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• 2020

The objective of this study was to investigate the effect of cold-pressed flaxseed oil through the roasting temperature (unroasted and roasted at 150℃ and 200℃) and time (10 and 20 min) on the chemical changes. Cold-pressed flaxseed oil extraction yield was calculated with respect to the roasted process and total phenolic content, fatty acid composition, and volatile compound were analyzed. The extraction yield was increased in the roasted oil compared to the unroasted oil. Total phenolic content was significantly higher in oil from the roasted at 150℃ for 20 min compared to other roasting condition. Fatty acid composition was not affected by the extraction process. The content of aldehyde, ketone, furan, and pyrazine was higher than in the roasted at 200℃ compared to the unroasted and roasted at 150℃. These findings suggest that cold-pressed flaxseed oil extracted from the roasted at 150℃ for 20 min may be considered acceptable for safe extraction process.

• Journal of the Korean Society of Safety
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• v.11 no.4
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• pp.84-89
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• 1996

The Oxidation of aflatoxin $G_1$ ($AFG_1$) with ozone in chloroform solvent gave the stable ozonide into ozonization of the double bond in the terminal furan ring, and this reaction have been carried out for 3hr at -78. 5$^{\circ}C$. The chloroform solvent was removed in a stream of nitrogen and the residue was separated by elution chromatography(EC). The structure of this compound have been identified by using MS, $^1H-NMR$, $^l3C-NMR$ and I. R spectroscopy, respectively. This compound was formed the normal stable AFG$_1$-ozonide into spontaneous rearrangement after unstable ozonide according to sigmatropic rearrange ment dependent upon cyclo addition by ozone.

• Archives of Pharmacal Research
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• v.15 no.1
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• pp.52-57
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• 1992

The molecular structure of a natural compound was determined by single crystal X-ray diffraction analysis. The compound was isolated by methanol extraction and repeated chromatography from the stem of Paulownia tomentosa. Yellow prismatic crystals of the compound, which were recrystallized from tetrahydrofuran, are triclinic, with a = 7.310 (6), b = 10.753(6), c = 11.586(5) ${\AA}.\;\alpha= 93.30(6),\;\beta=105.62(10),\;\gamma=109.49(7)^\circ,\;D_x=1.514,\;D_m=1.51 g/cm^3$, space group P1 and Z = 2. The structure was solved by direct method, and refined by least-squares procedure to the final R-value of 0.032 for 1271 independent reflections $(F\le3\sigma{(F))}$. The compound is one of new furanquinone analogue. The molecule has a nearly planar conformation with an intramolecular hydrogen bond. In the crystal, the planar molecules are arranged as a prallel sheet-like pattern, and these stackings are stabilized by the O-H...O type intermolecular hydrogen bonds. The other intermolecular contacts appear to be the normal van der Waals interactions.

• Natural Product Sciences
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• v.10 no.6
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• pp.315-320
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• 2004

Alpha-viniferin was previously isolated as a cyclooxygenase (COX)-2 inhibitor from Carex humilis (Cyperaceae) and is an oligomeric stilbene compound with benzofuran (BF) moieties in its chemical structure. In the present study, a chemically synthetic BF compound, named as 3,3-dimethyl-2,3,4,6,7,8,9,10,11,12,13,14,15,16,17,18-hexadecahydro-1H-benzo[b] cyclopentadeca[d]furan-1-one, was discovered to inhibit bacterial lipo polysaccharide (LPS)-induced prostaglandin $E_2$ $(PGE_2)$ production in macrophages RAW 264.7. The BF compound exhibited a selectively preferred inhibitory effect on COX-2 activity over COX-1 activity. Furthermore, BF compound inhibited LPS-induced COX-2 expression at transcription level. As a down-regulatory mechanism of COX-2 expression shown by BF compound, suppression of nuclear factor $(NF)-{\kappa}B$ activation has been demonstrated. BF compound inhibited LPS-induced $NF-{\kappa}B$ transcriptional activity and nuclear translocation of $NF-{\kappa}B$ p65, in parallel, but did not affect LPS-induced degradation of inhibitory ${\kappa}B{\alpha}$ protein $(I{\kappa}B{\alpha})$. Taken together, anti-inflammatory effect of BF compound on $PGE_2$ production was ascribed by its down-regulatory action on LPS-induced COX-2 synthesis in addition to inhibitory action on enzyme activity of COX-2.

• Food Science and Preservation
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• v.10 no.1
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• pp.70-74
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• 2003

The distribution of mesophilic and thermophilic bacteria in milled rice was not different according to growing land and variety of rice. However, The number of these bacteria were abundant in milled rice of lower milling degree or longer storage period. The growth of thermophilic bacteria in cooked rice of electric rice cooker was rapidly increased during storage of lower temperature below 75 $^{\circ}C$. Thermophilic bacteria were not appeared just after cooking. After cooked rice was stored far 18∼24 hon thermophilic bacterial growth was rapidly increased by changing spore to vegetative cell. The positive relation between cell number of thermophilic bacteria and occurrence of off-odor was slightly observed. The number of thermophilic bacteria in upper cooked rice of oven and was higher than those in inner and lower cooked rice. Major volatile compound of milled rice cooked and stored in electric rice cooker was hexanal oriented from rice. After long storage, it was confirmed that furan was major volatile compound as off-odor.

• Food Science and Biotechnology
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• v.18 no.2
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• pp.463-470
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• 2009

Sixteen antioxidative active compounds isolated from the EtOAc layer of MeOH extracts of kochujang, Korean fermented red pepper paste, were structurally elucidated as fumaric acid, methyl succinate, succinic acid furan-2-yl ester methyl ester (gochujangate, a novel compound), 2-hydroxy-3-phenylpropanoic acid, 3,4-dihydroxybenzoic acid, 2,3-dihydroxybenzoic acid, 2,4-dihydroxybenzoic acid, 6,7-dihydroxy-2H-chromen-2-one (esculetin), caffeic acid, cis-p-coumaric acid, trans-p-coumaric acid, daidzin, genistin, apigenin 7-O-$\beta$-D-apiofuranosyl($1{\rightarrow}2$)-$\beta$-D-glucopyranoside, apigenin 7-O-$\beta$-Dglucopyranoside, and quercetin 3-O-$\alpha$-L-rhamnopyranoside by mass spectrometry (MS) and nuclear magnetic resonance (NMR) experiments. These compounds were analyzed for the first time as antioxidants from kochujang.

• Proceedings of the PSK Conference
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• 2003.10b
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• pp.156.2-157
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• 2003

Lipopolysaccharide (LPS)-stimulated macrophages produced a large amounts of nitric oxide (NO) by inducible nitric oxide synthase (iNOS). This is an important mechanism in macrophages-induced septic shock and inflammation. In the present study, we tested a synthetic propenone compound, l-furan-2-yl-3-pyridin-2-yl-propenone (FPP-3) for its ability to inhibit the production of tumor necrosis factor-a (TNF-$\alpha$) and an inducible enzyme, iNOS, in the LPS-stimulated murine macrophage-like cell line, Raw264.7. FPP-3 consistently inhibited nitric oxide (NO) and TNF-$\alpha$ production in a dose dependent manner, with $IC_50$> values of 10.0 and 13.1 $\mu$M, respectively. (omitted)

• Journal of the Korean Society of Food Science and Nutrition
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• v.33 no.10
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• pp.1689-1697
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• 2004

Aroma compounds in 6 different Byeolmijang were extracted by SDE (simultaneous steam distillation extraction) and analyzed with GC (gas chromatography) and GC/MS (mass-spectrometry). The major aroma compounds in the 6 different Byeolmijang during aging were 1-octene-3-ol, hexanal, benzeneacetaldehyde, benzaldehyde, furfural, pyrazine compounds, benzyl-alcohol, furan compounds and phenol type compounds. Generally, benzeneacetaldehyde, benzaldehyde, furfural, pyrazine compounds and phenol type compounds were increased during aging. On the other hand, 1-octene-3-ol, hexanal, benzyl-alcohol and furan compounds were decreased during aging. 2-Heptenal and 2,4-decadienal in Daemaekjang, pyrazine and phenol type compounds in Sanghwangjang and phenol type compounds including phenol, 4-methoxy-phenol and 4-ethyl-phenol in Mujang were identified as major aroma compounds, respectively. The major aroma compound in Bizijang was 2,4-decadienal and in Sodujang, the major aroma compounds were 2,3-dihydro-benzofuran and 2-methoxy-4-vinylphenol. Linaool, geraniol, 6-elemene, 6-lonone and ledene were detected in Jigeumjang possibly due to the addition of powdered red pepper.