• 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.

• Journal of Integrative Natural Science
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• v.3 no.2
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• pp.103-106
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• 2010

Pentiptycene and its derivatives having cavity, ${\pi}-{\pi}$ stacking prohibition, and AIEE functionalities were synthesized. 6,7-Dibromo-1,4-dihydropentiptycene-1,4-epoxide was obtained from the reaction of 6,7-dibromo-1,4-dihydronaphthalene-1,4-epoxide and anthracene. All the synthesized compounds were characterized by fourier transform infrared spectroscopy (FTIR), 1H-NMR, and 13C-NMR spectroscopy. Prepared pentiptycene derivatives could be useful precursor for organofluorene compounds which could be an excellent candidate for electronic devices such as organic light-emitting diodes (OLED's) and chemical sensor.

• Journal of Ginseng Research
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• v.13 no.1
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• pp.42-48
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• 1989

The binding of bay region diol-epoxides of polycyclic aromatic hydrocarbons (PAHs) to target tissue DNA is thought to be essential for the initiation of cancer by these compounds. In this study we investigated the effect of polyacetylenes such as panaxynol and panaxydol on the formation of benzo(a)pyreno (BP)-metabolite-DNA adduct in the liver of ICR mice. Treatment of mice by i.p. administration of polyacetylenes produced a marked reduction in BP metabolite binding to DNA in vitro. Following i.v. administration of (3H)BP(300, ${\mu}$Ci/21 nmoles/0.1 nt DMSO) to mice, radioactivity was detected in the DNA of the liver in vivo. The result of tentative identification of the 4 peaks between the two standard markers for high pressure liquid chromatography showed that the peaks. I, II, III, and IV were BP-phenol oxide-DNA adduct (or BP-diol-epoxide-dCyt. adduct), (-) BP$.$diolepoxide I:dGuO adduct, (+) BP-diol-epoxide I: dGuo adduct, and BP-diol-epoxide II:dGuO adduct, respectively. The minor adduct, (-) BP-diol epoxide I: dGuo was reduced to 6971 of the amount of the control, while the major adduct, (+) BP-diolepoxide I: dGuO(peak II) which was produced from (-) BP-7, 8-diol was reduced to 78% of that of the control. The amount of the minor adduct, BP-diol-epoxide II:dGuo adduct(peak IV) which formed from (+) BP-7, 8-diol was 58% of the control. These results show that the panaxydol is more related to inhibition of the formation of the minor ad- ducts than of the major adducts, which were generally produced from ($\pm$) BP-7, 8-dihydro-dials.

• Journal of Life Science
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• v.15 no.1 s.68
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• pp.136-140
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• 2005

Microbial cell-based UV spectrometric assay for the quantitative measurement of epoxide hydrolase activity was evaluated and optimized for the efficient screening of whole cell activity of novel epoxide hydrolase. Epoxide hydrolase activity was determined by measuring the increase of the oxidized product, benzaldehyde. The effects of the concentrations of phenyl-1,2-ethanediol, sodium metaperiodate and cells were optimized for epoxide hydrolase-catalyzed hydrolysis of styrene oxide. The relevant kinetic parameters of Km and $V_{max}$ for the hydrolysis of (R)-styrene oxide by Rhodotorula glutinis were determined from Lineweaver-Burk plot as 41.2 nmol/min$\cdot$mg dcw and 7.5 mM respectively, and coincided well with those from GC analysis.

• YAKHAK HOEJI
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• v.56 no.1
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• pp.42-47
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• 2012

Soluble epoxide hydrolase (sEH) is a metabolic regulator of epoxyeicosatrienoic acids (EETs). EETs have many beneficial effects, vasodilation, anti-diabetes, anti-inflammation, cardiovascular protection, renal protection. Therefore, selective sEH inhibitors have a potential for treating these diseases. In the present study, screening methods for sEH inhibitors using PHOME ((3-phenyl-oxiranyl)-acetic acid cyano-(6-methoxynaphthalen-2-yl)-methyl ester) and 14-15-EET as substrates were established. To determine selectivity, microsomal epoxide hydrolase (mEH) inhibition assay was also developed using styrene oxide as a substrate of microsomal epoxide hydrolase. Our results obtained from 12-[[(tricyclo[3.3.1.13,7]dec-1-ylamino)carbonyl]amino]-dodecanoic acid (AUDA) used as a positive sEH inhibitor and valpromide used as a positive mEH inhibitor showed that these methods are useful for discovery of drug candidates.

• Journal of Institute of Control, Robotics and Systems
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• v.11 no.10
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• pp.857-863
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• 2005

A yeast strain utilizing styrene epoxide as a sole carbon and energy source was isolated from soil samples for the production of enantiopure of styrene epoxide by kinetic resolution. The strain, identified as a Rhodosporidium toruloides SJ-4, expressed an epoxide hydrolase which preferentially converted (R)-styrene epoxide into the corresponding diol. A maximum activity of 135 U/L was observed when biomass (dry cell mass) reached 6.7 g/L at 21 h of batch culture. Under the partially optimized reaction conditions ($35^{\circ}C$ and pH 8.0), the optically pure (S)-styrene epoxide was obtained with the yield of 21% when the initial substrate concentration was 100 mM. The reaction was completed at 9 h.

• Korean Journal of Pharmacognosy
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• v.28 no.2
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• pp.88-92
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• 1997

The full NMR assignment of hispidulin 7-0-neohesperidoside (1) isolated from Cirsium japonicum var. ussuriense was made with the aid of 2D correlation NMR techniques such as HMQC and HMBC. To investigate detoxification of bromobenzene-induced hepatic lipid peroxidation by compound 1, hepatic lipid peroxide level and the activities of enzymes responsible for production and removal of epoxide were studied. The level of lipid peroxide elevated by bromobenzene was significantly reduced by compound 1. This compound administered daily over one week before intoxication with bromobenzene did not affect the activities of aminopyrine N-demethylase, aniline hydroxylase, glutathione S-transferase. Epoxide hydrolase activity was decreased significantly by bromobenzene, which was restored to the control level by pretreatment of persicarin. The results suggest that the bromobenzene-induced hepatic lipid peroxidation by compound 1 is reduced by enhancing the activity of epoxide hydrolase, an enzyme removing bromobenzene epoxide.

• KSBB Journal
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• v.19 no.1
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• pp.42-49
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• 2004

A gene coding for epoxide hydrolase (EH) of Aspergillus niger LK, a fungus possessing the enantioselective hydrolysis activity for racemic epoxides, was characterized by phylogenetic analysis. The deduced protein of A. niger LK epoxide hydrolase shares significant sequence similarity with several bacterial EHs and mammalian microsomal EHs (mEH) and belongs to the a/${\beta}$ hydrolase fold family. EH from A. niger LK had 90.6% identity with 3D crystal structure of lqo7 in Protein Data Bank. Sequence comparison with other source EHs suggested that Asp$\^$l92/, Asp$\^$374/ and His$\^$374/ constituted the catalytic triad. Based on the multiple sequence comparison of the functional and structural domain sequence, the phylogenetic tree between relevant epoxide hydrolases from various species were reconstructed by using Neighbor-Joining method. Genetic distances were so far as 1.841-2.682 but characteristic oxyanion hole and catalytic triad were highly conserved, which means they have diverged from a common ancestor.

• Journal of the Korean Chemical Society
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• v.32 no.6
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• pp.575-580
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• 1988

$({\pm})-{\gamma}$-Rhodomycinone(4) and 10-Deoxy-${\gamma}$-rhodomycinone(5), late-stage Precursors of the alglycone of antitumor antibiotic Rhodomycin(2) were prepared from the cleavage of epoxide ring of 9-ethyl-9,10-epoxy-4,6, 11-trihydroxy-7,8,9,10-tetrahydronaphthacene-5,12-dione(10). The epoxide 10 was furnished from 9-acetyl-4,5,6,11,12-pentamethoxy-7,8-dihydronaphthacene(6), which was assembled utilizing ring annelation methodology developed by Hauser-Rhee.

• Korean Journal of Food Science and Technology
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• v.30 no.6
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• pp.1312-1320
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• 1998

Some commercial beef loins 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 as the raw state. These samples were irradiated by electron beam (0, 1, 2 kGy), and then stored in refrigerator $(2{\sim}4^{\circ}C)$. Identity and quantity of cholesterol oxides were analysed at the 0, 7th, 14th day of storage. In the samples that were raw and packaged aerobically, $7{\alpha}-hydroxycholesterol,\;{\beta}-epoxide,\;7{\beta}-hydroxycholesterol$ and 7-ketocholesterol were detected over $0.5\;{\mu}g/g$. Cholestanetriol and${\alpha}-epoxide$ were detected at levels below $0.5\;{\mu}g/g$ during storage. In the samples that were raw and vacuum-packaged, $7{\alpha}-hydroxycholesterol$, 7-ketocholesterol and cholestanetriol were detected. In the samples that were cooked and packaged aerobically, cholestanetriol and ${\alpha}-epoxide$ were detected below $0.5\;{\mu}g/g$ during storage. $7{\alpha}-hydroxycholesterol,\;{\beta}-epoxide,\;7{\beta}-hydroxycholesterol$and 7-ketocholesterol were detected as $1.53{\sim}26.81,\;1.07{\sim}5.23,\;40.64{\sim}101.30\;and\;7.16{\sim}33.91\;{\mu}g/g$, respectively. In all results, total amounts of cholesterol oxide increased significantly as irradiation dose and storage time increased (P<0.05).