• Archives of Pharmacal Research
• /
• v.22 no.2
• /
• pp.99-107
• /
• 1999

A series of organosulfur compounds were synthesized with the aim of developing chemopreventive compounds active against hepatotoxicity and chemical carcinogesis. 2-(Allylthio) prazine (2-AP) was effective in inhibiting cytochrome P450 2E1-mediated catalytic activities and protein expression, and in inducing microsomal epoxide hydrolase and major glutathione S-transferases. 2-AP reduced the hepatotoxicity caused by toxicant sand elevated cellular GSH content. Development of skin tumors, pulmonary adenoma and aberrant crypt foci in colon by various chemical carcinogens was inhibited by 2-AP pretreatment. Anticarcinogenic effects of 2-AP at the stage of initiation of tumors were also observed in the aflatoxin B1 ($AFB_1$)-induced three-step medium-term hepatocarcinogenesis model. Reduction of $AFB_1$-DNA adduct by 2-AP appeared to result from the decreased formation of $AFB_1$-8,9-epoxide via suppression of cytochrome P450, while induction of GST 2-AP increases the excretion of glutathione-conjugated $AFB_1$ . 2-AP was a radioprotective agent effective against the lethal dose of total body irradiation and reduced radiation-induced injury in association with the elevation of detoxifying gene expression. 2-AP produces reactive oxygen species in vivo, which is not mediated with the thiol-dependent production of oxidants and that NF-KB activation is not involved in the induction of the detoxifying enzymes. the mechanism of chemoprotection by 2-AP may involve inhibition of the P450-mediated metabolic activation of chemical carcinogens and enhancement of electrophilic detoxification through induction of phase II detoxification enzymes which would facilitate the clearance of activated metabolites through conjugation reaction.

• Clean Technology
• /
• v.16 no.4
• /
• pp.239-244
• /
• 2010

The carboxylation of the fluorenyl epoxide with a spiro framework, 9,9'-Bis(4-oxiranylmethoxyphenyl) fluorine (2) was catalyzed by some onium salts such as quaternary ammonium and phosphonium salts to produce the corresponding five-membered cyclic carbonate (3) in an efficient and environmentally benign fashion. The coupling reactions depend greatly on the kind of the halide anions and alkyl chain length of the onium salts. While the reaction was sensitive to the reaction temperature, the reaction trends suggest that the catalytic efficiency of the quaternary ammonium halides may correlate strongly with the melting points of the halides. The reactions using a catalytic amount (2 mol %) of quaternary ammonium bromide with an n-butyl chain at 75.9 bar of $CO_2$ and 393 K give the highest yield of the cyclic carbonate (92%).

• Food Science of Animal Resources
• /
• v.22 no.2
• /
• pp.137-144
• /
• 2002

Pork loins that retailed in market were used as experimental samples. Some pork samples in raw state were packaged with PVDC in either aerobic or vacuum condition. The other pork samples were cooked until core temperature reached at 70$\^{C}$ and then packaged immediately in the same way with the raw samples. After these samples were irradiated by electron beam 6 kGy, the samples were stored in a refrigerator (2∼4$\^{C}$). Identification and quantification of cholesterol oxides were performed at 0 and 7 days. The results were following. During the early stage of storage, cholesterol oxides were not produced from the raw meat samples, but with the passage of storage time,7 $\alpha$-hydroxycholesterol, 7$\beta$-hydroxycholesterol, 7-ketocholesterol, 20 $\alpha$-hydroxycholesterol, $\beta$-epoxide and $\alpha$-epoxide, which were not produced during the early stage of storage, were produced. The production of cholesterol and lipid oxidation products were significantly higher (P<0.05) in the meats with aerobic packaging than those with vacuum packaging, Cooked meat after irradiation showed 7 $\alpha$-hydroxycholesterol, 7 $\beta$-hydroxycholesterol, $\alpha$-epoxide and cholestanetriol on the 7th day of storage, although those chemicals were not produced during the early stage of storage. Production of cholesterol oxides was significantly increased (P<0.05) with the passage of storage time for all treatments, and showed significantly lower value (P<0.05) with the vacuum packaging than these for aerobic packaging. Species of cholesterol oxides from irradiated meat after cooking were similar to those from cooked meat after irradiation. Collectively, it was found that the production of cholesterol oxides was more easily affected by packaging condition than irradiation.

• Journal of Animal Science and Technology
• /
• v.44 no.1
• /
• pp.113-122
• /
• 2002

Beef loins that retailed in market were used as experimental samples. Some beef samples in raw state were packaged with PVDC as aerobic and vacuum condition. The other beef samples were cooked until core temperature arrived at 70$^{\circ}C$ and then packaged immediately in the same way of raw samples. After these samples were irradiated by electron beam 6kGy, irradiated samples were stored in refrigerator(2～4$^{\circ}C$). Identify and quantity of cholesterol oxides were analysed stored at 0 and 7 days, respectively. During the early stage of storage, 7$\beta$-hydroxycholesterol and 7-ketocholesterol were respectively produced from the raw meat samples, and the production of these chemicals were significantly higher (P$<$0.05) from the meats with aerobic packaging than those with vacuum packaging. With the passage of storage time, 7$\alpha$-hydroxycholesterol, 20$\alpha$-hydroxycholesterol, $\beta$-epoxide, $\beta$-epoxide and some other chemicals, which were not produced during the early stage of storage, were produced, Also, the production of these chemicals were significantly increased (P$<$0.05) with the passage of storage time. Cooked meat after irradiation and irradiated meat after cooking produced cholesterol on the 7th day of storage, although this chemical was not produced during the early stage of storage. Production of cholesterol oxides was significantly increased (P$<$0.05) with the passage of storage time for all treatments, and showed significantly lower value (P$<$0.05) with the vacuum packaging than aerobic packaging. Summarizing the aforementioned results, it was found that the production of cholesterol oxides was more easily affected by packaging condition than irradiation.

• Microbiology and Biotechnology Letters
• /
• v.35 no.4
• /
• pp.285-291
• /
• 2007

Enantioconvergent hydrolysis process for the preparation of chiral diol from racemic epoxides by using the recombinant Caulobacter crescentus epoxide hydrolase (CcEH) in Escherichia coli BL21 (DE3) was optimized. For the optimization, the effects of detergent, temperature and product inhibition on the enantiopurity and the yield of diol were investigated. (R)-phenyl-1,2-ethanediol with 92% enantiomeric excess and 56% yield from 20 mM racemic styrene oxide was obtained by using the recombinant CcEH at the optimal condition of $10^{\circ}C$ and the addition of 2% (w/v) Tween 80. At 50 mM racemic styrene oxide was used as a substrate, (R)-phenyl-1,2-ethanediol was obtained with 87% enantiomeric excess and 77% yield. Racemic phenyl-1,2-ethanediol, (R)-phenyl-1,2-ethanediol and (S)-phenyl-1,2-ethanediol dramatically inhibited the hydrolytic activity of the recombinant CcEH. These results suggested that another EH with the regioselectivity on ${\beta}$-position of (R)-enantiomer and without feedback inhibition by products would be needed as the partner EH of C. crescentus EH.

• Journal of Life Science
• /
• v.18 no.1
• /
• pp.136-142
• /
• 2008

A recombinant Pichia pastoris carrying double expression cassette of Rhodotorula glutinis epoxide hydrolase(RgEH) gene was developed and used for preparing enantiopure (S)-styrene oxide from racemic mixture of styrene oxide. BglII restriction site of original RgEH gene (pPICZ B/RgEH #2) of previous report was mutated using PCR technique for the construction of double expression cassette containing promoter ($P_{AOX1}$), EH gene and transcription terminator ($TT_{AOX1}$) in pPICZ C vector. Double expression cassette with RgEH was inserted into the chromosomal DNA of P. pastoris. $V_{max}$ ($2.2{\mu}mol\;min^{-1}mg\;dcw^{-1}$) on (R)-styrene oxide of P. pastoris with double expression cassette was about 6-fold higher than that ($0.4{\mu}mol\;min^{-1}mg\;dcw^{-1}$) of P. pastoris with single expression cassette. For the determination of the optimal condition, the effects of detergent and temperature on the enantioselective hydrolytic activity and yield of the enantiomer were investigated. When the reaction was performed at $10^{\circ}C$ for 10 min in the presence of 0.5% Tween 20, enantiopure (S)-styrene oxide with 99.9% ee was obtained as the yield 43.4 % from 20 mM racemic sustrate.

• Bulletin of the Korean Chemical Society
• /
• v.26 no.5
• /
• pp.826-828
• /
• 2005

• Proceedings of the Korean Environmental Sciences Society Conference
• /
• 2004.05a
• /
• pp.101-102
• /
• 2004

유기염소계 농약류 14종을 분석한 결과 황소개구리의 경우 모든 시료에서 검출되지 않았다. 붕어의 경우 11종의 분석대상물질이 검출되지 않았고, heptachlor epoxide B, trans-nonachlor, p,p´-DDE가 각각 3개 지점, 7개 지점, 5개 지점에서 검출되었다.

• Proceedings of the Korean Society of Life Science Conference
• /
• 2005.09a
• /
• pp.88-88
• /
• 2005

• Proceedings of the Korean Society of Life Science Conference
• /
• 2005.09a
• /
• pp.89-89
• /
• 2005