• Journal of the Korean Chemical Society
• /
• v.48 no.4
• /
• pp.436-438
• /
• 2004

• Bulletin of the Korean Chemical Society
• /
• v.30 no.10
• /
• pp.2381-2386
• /
• 2009

The tetrakis(thio)-substituted-1,4-benzoquinone products 4a-e, 6, 7, and the mono(alkoxy)-tris(thio)-substituted-1,4- benzoquinone products 5a-e and 8a-e were synthesized from the reactions of p-chloranil with some thiols and mixture of two different thiol compounds in alcohol in the presence of $Na_2CO_3$ at room temperature. The structures of the novel S,S,S,S- and S,S,S,O- substituted products, which were obtained by the reactions of p-chloranil as a starting compound with n-propanethiol, n-pentanethiol, n-decanethiol, n-dodecanethiol, 2-methyl-2-propanethiol, and mixture of n-decanethiol and n-cyclohexanethiol as S-nucleophiles, were characterized by spectroscopic methods.

• Archives of Pharmacal Research
• /
• v.28 no.4
• /
• pp.391-394
• /
• 2005

The allylthio group of allicin and other organosulfur compounds, isolated from garlic, is considered a pharmacophore, and a key structure component of the molecule, which affords biological activities. In the foregoing studies, various 3-alkoxy-6-allylthiopyridazine derivatives (K­compounds) were synthesized, and their biological activities tested in animals. As expected, the various derivatives showed good hepatoprotective activities on carbon tetrachloride-treated mice and aflatoxin B1-treated rats, and chemopreventive activities on hepatocarcinoma cells in rats. Other new pyridazine derivatives, with the oxygen atom at the 3-position of the 3-alkoxy­6-allylthiopyridazine displaced by sulfur (S), were synthesized, and their activities tested in vitro. Thio-K6, one of the sulfur-substituted compounds, showed better chemopreventive activity toward hepatocarcinoma cells.

• Korean Journal of Fisheries and Aquatic Sciences
• /
• v.41 no.6
• /
• pp.414-418
• /
• 2008

Volatile compounds in Omangdungi (Styela plicata)-Doenjang (soybean paste) stew were analyzed using solvent-assisted flavor evaporation/gas chromatography/mass-selective detection/olfactometry (SAFE/GC/MSD/O) and aroma extract dilution analysis (AEDA). The GC/O analysis detected 37 volatile compounds, of which 32 were positively identified, and included 9 aldehydes, 5 alcohols, 4 aromatic hydrocarbons, 4 ketones, 3 esters, 3 N-containing compounds, 2 acids, 1 S-containing compound, and 1 furan. Nine aroma-active odorants ($\log_3FD{\geq}3.0$) in the sample included six compounds derived from Doenjang (3-methyl(thio)propanal, tetramethylpyrazine, 4-vinyl-2-methoxyphenol, 2-acetylpyrrole, butyric acid, and 2-methoxyphenol) and three compounds from Omangdungi (2-acetyl-2-thiazoline, 9-decanol, and 6-decenol). Three compounds derived from Omangdungi (9-decanol, 6-decenol, and 6-nonenol) were thought to enhance the seafood-like flavor of Omangdungi-Doenjang stew.

• Natural Product Sciences
• /
• v.24 no.2
• /
• pp.132-138
• /
• 2018

Phytochemical investigation of 80% MeOH extract of the aerial parts of Capsella bursa-pastoris yielded fourteen compounds (1 - 14). The structures of the compounds were elucidated by spectroscopic methods to be methyl-1-thio-${\beta}$-D-glucopyranosyl disulfide (1), 10-methylsulphinyl-decanenitrile (2), 11-methyl-sulphinyl-undecanenitrile (3), 1-O-(lauroyl)glycerol (4), phytene-1, 2-diol (5), (3S,5R,6S,7E)-5,6-epoxy-3-hydroxy-7-megastigmen-9-one (6), loliolide (7), ${\beta}$-sitosterol (8), 3-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-1-propanone (9), 1-feruloyl-${\beta}$-D-glucopyranoside (10), pinoresinol-4'-O-${\beta}$-D-glucopyranoside (11), luteolin (12), quercetin-3-O-${\beta}$-D-glucopyranoside (13), and luteolin 6-C-${\beta}$-glucopyranoside (14). Although compound 1 was reported as synthetic compound, 1 was first isolated from natural source. NMR spectral data assignments of 1, 2 and 3 were reported for the first time, and compounds 1 - 14 were for the first time reported from this plant source. The anti-inflammatory effects of 1 - 14 were evaluated in lipopolysaccharide (LPS)-stimulated murine microglia BV-2 cells. Compounds 12 exhibited strong inhibitory effects on nitric oxide production in LPS-activated BV-2 cells with $IC_{50}$ values of $9.70{\mu}M$.

• Journal of Microbiology and Biotechnology
• /
• v.18 no.11
• /
• pp.1768-1772
• /
• 2008

CW-270031 is a novel synthesized carbapenem antibiotic with a broad antimicrobial activity. Carbapenem antibiotics are well known for their nephrotoxicity. In this study, we evaluated the nephrotoxicity potential of this compound in rabbits, which are known for being more sensitive than other animals to renal insult. CW-270031 was administered to NZW male rabbits via an ear vein (200 mg/kg, single injection). Blood samples were collected on 2, 3, and 4 days after treatment. Urea nitrogen and creatinine in plasma were quantified. Four days after the treatment, all animals were autopsied and histopathological examinations were performed on their kidneys, revealing that cephaloridine and imipenem were highly nephrotoxic, and cefazolin had mild renal toxicity, whereas CW-270031 as well as meropenem and tienam had no toxicity to the kidney. The present findings suggest that CW-270031 is a potential carbapenem antibiotic with no nephrotoxicity.

• Korean Journal of Food Science and Technology
• /
• v.20 no.4
• /
• pp.606-612
• /
• 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.

• Bulletin of the Korean Chemical Society
• /
• v.28 no.9
• /
• pp.1510-1514
• /
• 2007

Recently, it has been reported that the inhibition of the strand transfer function of HIV-1 integrase is necessary to obtain significant antiviral activity. Accordingly, several compounds typified by aryl 1,3-diketo acids that can inhibit strand transfer reaction of HIV-1 IN have been identified. In this work, we synthesized new 4- hydroxy-5-azacoumarin-3-carbox(thio)amides (1a-h) and evaluated for the inhibition of HIV-1 IN strand transfer reaction with a brief SAR. Among synthesized, compound 1e was the most potent HIV-1 IN inhibitor with equipotent activity to that of L-708,906. Therefore, the 4-hydroxy-5-azacoumarin ring can be considered as a new scaffold in designing more potent of HIV-1 IN inhibitors for treatment of AIDS.

• Natural Product Sciences
• /
• v.26 no.3
• /
• pp.214-220
• /
• 2020

Brassica oleracea var. gongylodes (red kohlrabi) is a biennial herbaceous vegetable whose edible bulbotuber-like stem and leaves are consumed globally. Sliced red kohlrabi tubers were extracted using methanol and the concentrated extract was partitioned successively with dichloromethane (CH₂Cl₂), ethyl acetate (EtOAc), n-butanol (n-BuOH) and water (H₂O). Repeated column chromatography of EtOAc fraction through silica, sephadex LH-20 and RP-18 gel led to isolation of eleven compounds of which compound 1 was a new glycosylated indole alkaloid derivative, 1-methoxyindole 3-carboxylic acid 6-O-β-D-glucopyranoside. Others were known compounds namely, β-sitosterol glucoside (4), 5-hydroxymethyl-2-furaldehyde (5), methyl-1-thio-β-D-glucopyranosyl disulfide (6), 5-hydroxy-2-pyridinemethanol (7), (3S,4R)-2-deoxyribonolactone (8), n-butyl-β-D-fructopyranoside (9), uridine (10) and three fructose derivatives, D-tagatose (11), β-D-fructofuranose (12) and β-D-fructopyranose (13). Similarly, isolation from CH₂Cl₂ fraction gave two known indole alkaloids, indole 3-acetonitrile (2) and N-methoxyindole 3-acetonitrile (3). The structure elucidation and identification of these compounds were conducted with the help of ¹³C and ¹H NMR, HMBC, HMQC, EIMS, HR-ESIMS and IR spectroscopic data, and TLC plate spots visualization. Compounds 2, 3, 4, 5, 6, 7, 8 and 9 are noted to occur in kohlrabi for the first time. Different bioactivities of these isolated compounds have been reported in literature.

• Korean Journal of Microbiology
• /
• v.40 no.2
• /
• pp.127-132
• /
• 2004

We isolated 50 strains from sludge of wastewater treatment aeration tank using selective medium for Thio-bacillus sp. by membrane filtration method. They were identified as Thiobacillus neapolitanus (7), T. tepidarius (4), T. dientrificans (5), T. versutus (23), T. intermedius (2) and T. perometabolis (9). We selected Thiobacillus versutus strain KT51, which had the highest removal efficiency (100％) of hydrogen sulfide and the highest removal efficiency (85％) of dimethyl sulfide for 30 min in screen test. Also Thiobacillus versutus strain KT81 had the highest removal efficiency (26％) of dimethyl disulfide for 30 min in screen test. In applification of lab-scale reactor (closed-biological treatment) using Thiobacillus versutus strain KT51, results were 99.8％ (＜0.02 ppm) removal efficiency of hydrogen sulfide for 15 min.