• Journal of Microbiology
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• v.45 no.4
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• pp.333-338
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• 2007

Intracellular NADH:quinone reductase involved in degradation of aromatic compounds including lignin was purified and characterized from white rot fungus Trametes versicolor. The activity of quinone reductase was maximal after 3 days of incubation in fungal culture, and the enzyme was purified to homogeneity using ion-exchange, hydrophobic interaction, and gel filtration chromatographies. The purified enzyme has a molecular mass of 41kDa as determined by SDS-PAGE, and exhibits a broad temperature optimum between $20-40^{\circ}C$, with a pH optimum of 6.0. The enzyme preferred FAD as a cofactor and NADH rather than NADPH as an electron donor. Among quinone compounds tested as substrate, menadione showed the highest enzyme activity followed by 1,4-benzoquinone. The enzyme activity was inhibited by $CuSO_4,\;HgCl_2,\;MgSO_4,\;MnSO_4,\;AgNO_3$, dicumarol, KCN, $NaN_3$, and EDTA. Its $K_m\;and\;V_{max}$ with NADH as an electron donor were $23{\mu}M\;and\;101mM/mg$ per min, respectively, and showed a high substrate affinity. Purified quinone reductase could reduce 1,4-benzoquinone to hydroquinone, and induction of this enzyme was higher by 1,4-benzoquinone than those of other quinone compounds.

• Journal of Microbiology and Biotechnology
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• v.30 no.9
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• pp.1436-1442
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• 2020

Amylosucrase (ASase, E.C. 2.4.1.4) is capable of efficient glucose transfer from sucrose, acting as the sole donor molecule, to various functional acceptor compounds, such as polyphenols and flavonoids. An ASase variant from Deinococcus geothermalis, in which the 226^th alanine is replaced with asparagine (DgAS-A226N), shows increased polymerization activity due to changes in the flexibility of the loop near the active site. In this study, we further investigated how the mutation modulates the enzymatic activity of DgAS using molecular dynamics and docking simulations to evaluate interactions between the enzyme and phenolic compounds. The computational analysis revealed that the A226N mutation could induce and stabilize structural changes near the substrate-binding site to increase glucose transfer efficiency to phenolic compounds. Kinetic parameters of DgAS-A226N and WT DgAS were determined with sucrose and 4-methylumbelliferone (MU) as donor and acceptor molecules, respectively. The k_cat/K_m value of DgAS-A226N with MU (6.352 mM^-1min^-1) was significantly higher than that of DgAS (5.296 mM^-1min^-1). The enzymatic activity was tested with a small phenolic compound, hydroquinone, and there was a 1.4-fold increase in α-arbutin production. From the results of the study, it was concluded that DgAS-A226N has improved acceptor specificity toward small phenolic compounds by way of stabilizing the active conformation of these compounds.

• Journal of the Korean Society of Tobacco Science
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• v.29 no.1
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• pp.30-40
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• 2007

The objective of this study was to investigate the contribution of various smoke constituents to the toxicological activity of total particulate matter(TPM) or the gas/vapor phase(GVP). These components included phenol compounds, aromatic amines, polycyclic aromatic hydrocarbons, heterocyclic amines, and carbonyl compounds. The mutagenic and cytotoxic potencies were assessed using the Salmonella mutagenicity assay with S. typimurium TA98 strain and the neutral red uptake cytotoxicity assay(NRU) with BALB/c 3T3 fibroblast cells, respectively. The Salmonella mutagenicity test showed that heterocyclic amines exhibited significantly higher levels of toxicity compared to other smoke constituents. Among them, 2-amino-3,4-dimethylimidazo[4,5-f]quinoline(MeIQ) was shown the most mutagenic compound with a specific mutagenicity of $7.9{\times}10^5\;revertants/{\mu}g$. An analysis of the possible contribution revealed that MeIQ account for only 0.85% of the 2R4F-TPM mutagenicity in TA98. NRU data demonstrated that high cytotoxic activity was obtained for hydroquinone, formaldehyde, and acrolein. Based on the results of the present study, the contribution of acrolein to the cytotoxicity of the GVP fraction was calculated as 61%. Thus, a large proportion of the cytotoxic activity of this complex mixture, cigarette smoke gas phase, can be attributed to the acrolein.

• Applied Chemistry for Engineering
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• v.25 no.1
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• pp.47-52
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• 2014

A series of liquid crystalline polyesters containing X-shaped mesogenic groups in main chain were synthesized through the solution polymerization of 2,5-di(4-substituted benzoate)hydroquinones and 4,4'-dicarboxy-1,8-diphenoxyoctane. The structures and properties of synthesized polymers were investigated by $^1H$-NMR, FT-IR, differential scanning calorimetry (DSC), thermogravimetry analysis (TGA), polarized optical microscopy (POM) and wide angel X-ray diffraction (WXRD). Inherent viscosities (${\eta}_{inh}$) of polymers were measured between 0.35 and 0.66 dL/g in 1,1,2,2-tetrachloroethane, and they were easily soluble in most of organic solvents used for this experiment. All polymers revealed relatively low melting transition temperature ($T_m$) and crystallinity, and also showed thermotropic nematic liquid crystallinity when they were heated to their melting temperatures. These properties of polymers were presumably due to the presence of the bulky substituting groups on the hydroquinone unit in mesogenic group.

• Preventive Nutrition and Food Science
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• v.2 no.3
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• pp.232-235
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• 1997

This study was investigated to determine antimutagenic effects of enzymatic browning reaction products (PEBRPs) obtained by reaction of polyphenol compouns with oxidase extracted from potato. Catechol (Ca) PEBRPs showed the strongeest inhibitor effects with 90% inhibition on benzo-($\alpha$)-pyrene(B($\alpha$)P) induced mutagenesis in Salmonella typhimurium TA98, but he least with40% inhibition on the 2-aminofluorene (2-AF) induced mutagenesis in TA98. The strong antimutagenic activities with 80% inhibition were observed in the presence of 100$\mu\textrm{g}$/plate of hydroquinone(HQ)-PEBRP on the B($\alpha$)P or 3-amino-1,4-dimethyl-5H-pyrido[4,3-b]indole(Trp-P-1) induced mutagenesis in TA98, whereas HQ-PEBRP showed the least antimutagenic effect on 2-AF-induced mutagenesis. The addition of 100$\mu\textrm{g}$ hydroxyhydroquinone(HHQ)-PEBRP to the plate led to approximately 82% inhibitory effects on 2-AF or Trp-P-1 induced mutagenesis in TA98, whereas the least antimutagenicity was obsrved in the4-nitroquinoline-1-oxide(4-NQO) induced mutagenesis in the presence of 100$\mu\textrm{g}$/plate of HHQ-PEBRP. More than 80% inhibiton were observed in the presence of 200$\mu\textrm{g}$/plate of Pyrogalol(Py)-PEBRP on the B($\alpha$)P or Trp-P-1 induced mutagenesis in TA98, but the least with 38% inhibition on 4-NQO induced mutagenesis in TA98. The results indicate that enzymatic browing reaction products of potato have a strong modulatory effect on mutagen induced mutagenesis in TA98.

• Bulletin of the Korean Chemical Society
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• v.13 no.2
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• pp.199-207
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• 1992

The approximate rates and stoichiometry of the reaction of excess sodium diethyldihydroaluminate (SDDA) with 68 selected organic compounds containing representative functional groups were examined under standard conditions (THF-toluene, $0^{\circ}C$ in order to compare its reducing characteristics with lithium aluminum hydride (LAH), aluminum hydride, and diisobutylaluminum hydride (DIBAH) previously examined, and enlarge the scope of its applicability as a reducing agent. Alcohols, phenol, thiols and amines evolve hydrogen rapidly and quantitatively. Aldehydes and ketones of diverse structure are reduced rapidly to the corresponding alcohols. Reduction of norcamphor gives 11% exo-and 89% endo-norborneol. Conjugated aldehydes such as cinnamaldehyde are rapidly and cleanly reduced to the corresponding allylic alcohols. p-Benzoquinone is mainly reduced to hydroquinone. Hexanoic acid and benzoic acid liberate hydrogen rapidly and quantitatively, however reduction proceeds very slowly. Acid chlorides and esters tested are all reduced rapidly to the corresponding alcohols. However cyclic acid anhydrides such as succinic anhydride are reduced to the lactone stage rapidly, but very slowly thereafter. Although alkyl chlorides are reduced very slowly alkyl bromides, alkyl iodides and epoxides are reduced rapidly with an uptake of 1 equiv of hydride. Styrene oxide is reduced to give 1-phenylethanol quantitatively. Primary amides are reduced very slowly; however, tertiary amides take up 1 equiv of hydride rapidly. Tertiary amides could be reduced to the corresponding aldehydes in very good yield ( > 90%) by reacting with equimolar SDDA at room temperature. Hexanenitrile is reduced moderately accompanying 0.6 equiv of hydrogen evolution, however the reduction of benzonitrile proceeds rapidly to the imine stage and very slowly thereafter. Benzonitrile was reduced to give 90% yield of benzaldehyde by reaction with 1.1 equiv of hydride. Nitro compounds, azobenzene and azoxybenzene are reduced moderately at $0^{\circ}C$, but nitrobenzene is rapidly reduced to hydrazobenzene stage at room temperature. Cyclohexanone oxime is reduced to the hydroxylamine stage in 12 h and no further reaction is apparent. Pyridine is reduced sluggishly at $0^{\circ}C$, but moderately at room temperature to 1,2-dihydropyridine stage in 6 h; however further reaction is very slow. Disulfides and sulfoxides are reduced rapidly, whereas sulfide, sulfone, sulfonic acid and sulfonate are inert under these reaction conditions.

• Journal of radiological science and technology
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• v.36 no.2
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• pp.165-173
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• 2013

This study was the estimation of the dose distribution for proton, prompt gamma rays and proton induced neutron particles, in case of exposing the proton beam to polymer gel dosimeter and water phantom. The polymer gel dosimeter was compositeness material of Gelatin, Methacrylic acid, Hydroquinone, Tetrakis and Distilled water. The density of gel dosimeter was $1.04g/cm^3$ which was similar to water. The 72, 116 and 140 MeV proton beams were used in the simulation. Proton beam interacted with the nuclei of the phantom and the nuclei in excited states emitted prompt gamma rays and proton induced neutron particles during the process of de-excitation. The proton particles, prompt gamma rays, proton induced neutron particles were detected by polymer gel dosimeter and water phantom, respectively. The gap of the axis for gel was 2 mm. The Bragg-peak for proton particles in gel dosimeter was similar to water phantom. The dose distribution for proton and prompt gamma rays in gel dosimeter and water phantom was approximately identical in case of 72, 116 and 140 MeV for proton beam. However, in case of proton induced neutron particles for 72, 116 and 140 MeV proton beam, particles were not detected in gel dosimeter, while the Water phantom absorbed neutron particles. Considering the resulting data, gel dosimeter which was developed in the normoxic state attentively detected the dose distribution for proton beam exposure except proton induced neutron particles.

• Applied Biological Chemistry
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• v.17 no.3
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• pp.149-176
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• 1974

Eight substituted diphenyl ether herbicides and some of their photoproducts were studied in terms of solution phase photolysis under simulated environmental conditions by using a Rayonet photochemical reactor. The test compounds absorbed sufficient light energy at the wavelength of 300 nm to undergo various photoreactions. All the photoproducts were confirmed by means of tlc, glc, ir, ms, and/or nmr spectrometry. The results obtained are summarized as follows: Solution phase photolysis of C-6989: An exceedingly large amount of p-nitrophenol formed strongly indicates the readiness of the ether linkage cleavage of this compound as the main reaction in all solvents used. Photoreduction of nitro to amino group(s) and photooxidation of trifluoromethyl to carboxyl group were recognized as minor reactions. Aqueous photolysis of p-nitrophenol: Quinone(0.28%), hydroquinone (0.66%), and p-aminophenol (0.42%) were confirmed as photoproducts, in addition to a relatively small amount of an unknown compound. The mechanisms of formation of these products were proposed to be the nitro-nitrite rearrangement via $n{\rightarrow}{\pi}^*$ excitation and the photoreduction through hydrogen abstractions by radicals, respectively. Solution phase photolysis of Nitrofen: Photochemical reduction leading to the p-amino derivative was the main reaction in n-hexane. In aqueous solution, the photoreduction of nitro to amino group and hydroxylation predominated over the ether linkage cleavage. Nucleophilic displacement of the nitro group by hydroxide ion and replacement of chlorine substituents by hydroxyl group or, to a lesser extent, hydrogen were also observed as minor reactoins. Solution phase photolysis of MO-338: Photoreduction of the nitro to amino group was marked in the n-hexane solution photolysis. In the aqueous solution, photoreduction of the nitro substituent and hydroxylation were the main reactions with replacement of chlorine substituents by the hydroxyl group and hydrogen, and cleavage of the ether linkage as minor reactions. Photolyses of MC-4379, MC-3761, MC-5127, MC-6063, and MC-7181 in n-hexane and cyclohexane: Photoreduction of the nitro group leading to the corresponding amino derivative and replacement of one of the halogen substituents by hydrogen from the solvent used were the key reactions in each compound. Aqueous photolysis of MC-4379: Cleavage of the ether linkage, replacement of the carboxymethyl by hydroxyl group, hydroxylation, and replacement of the nitro by hydroxy group were prominent with photoreduction and dechlorination as minor reactions. Aqueous photolysis of MC-3761: Cleavage of the ether linkage, replacement of the carboxymethyl by hydroxyl group, and photoreduction followed by hydroxylation were the main reactions. Aqueous photolysis of MC-5127: Replacement of carboxyethyl by hydrogen was predominant with ether linkage cleavage, photoreduction, and dechlorination as minor reactions. It was obvious that the decarboxyethylation proceeded more readily than decarboxymethylation occurring in the other compounds. Aqueous photolysis of MC-6063: Cleavage of the ether linkage and photodechlorination were the main reactions. Aqueous photolysis of MC-7181: Replacement of the carboxymethyl group by hydrogen and monodechlorination were the remarkable reactions. Cleavage of the ether linkage and hydroxylation were thought to be the minor reactions. Aqueous photolysis of 3-carboxymethyl-4-nitrophenol: The photo-induced Fries rearrangement common to aromatic esters did not appear to occur in the carboxymethyl group of this type of compound. Conversion of nitro to nitroso group was the main reaction.

• Journal of Haehwa Medicine
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• v.21 no.1
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• pp.125-133
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• 2012

본 논문은 피부미백에 관한 실험적 연구로서, 봉선화(Impatiens balsamina Linne)의 성분 중에서 하이드록시-나프타-퀴논(hydroxynaphthoquinone)이 멜라닌 생성억제 효능, 색소침착 저해 효과 등의 미백 활성이 있는 것으로 밝혀졌다. 피부흑화(melanogenesis)는 멜라닌 색소생성세포(melanocyte)에서 자외선 등의 자극에 대한 방어기작으로 멜라닌 생성 활동이 증가되고 이로 말미암아 만들어진 다량의 멜라닌이 각질형성세포(keratinocyte)로 전이되어 피부 표피층에 축척된 결과이다. 비록 멜라닌이 피부에 보호작용을 하나 피부의 과색소 침착은 기미, 주근깨, 피부염증 후의 피부흑화, 노인성 색소반점 등을 일으키며 이로 인해 피부미용 상의 불편뿐만 아니라 정신적으로 부정적인 영향을 미쳐 사회활동에 불편을 초래하기도 한다. 멜라닌 생성 과정은 아미노산의 일종인 티로신(tyrosine)에 티로시나제(tyrosinase)라는 효소가 작용하여 도파(DOPA), 도파퀴논(dopaquinone)으로 바뀐 후 비효소적인 산화 반응을 거쳐 만들어 지며, 이것이 피부 내에 이상 침착하여 기미, 검버섯 등이 생기는 것이라고 알려져 있다. 이와 같은 색소침착, 기미, 반점 등의 완화, 예방 및 치료에는 멜라닌 생성을 억제하는 물질, 예를 들면 하이드로퀴논(hydroquinone), 알부틴, 비타민 C 및 그 유도체 등이 개발되어 사용되고 있으나 이 중, 하이드로퀴논은 일단 효과가 인정되고 있지만 감작성이 있기 때문에 일반적으로 사용이 제한되고 있다. 아스콜빈산은 쉽게 산화되어, 이를 배합한 제품에는 변색, 변취가 되는 문제를 야기하고, 식물추출물 유래의 물질들은 식물의 산지에 따라 효능의 차이가 심하여 제품의 균질성이 유지되기 어렵다. 이러한 이유로 많은 멜라닌 생성을 억제하는 물질을 개발하기 위한 연구들이 계속 진행하고 있다. 2-히드록시-[1,4]나프토퀴논 유도체는 다음과 같은 구조를 나타낸다. 상기 구조에서 R은 포화 혹은 불포화된 직쇄 또는 분지쇄의 알킬로서, 바람직하게는 C1 내지 C10의 포화 혹은 불포화된 직쇄 또는 분지쇄의 알킬이고, 보다 바람직하게는 C1 내지 C5의 포화 혹은 불포화된 직쇄 또는 분지쇄의 알킬이다. 실험에 활용된 화합물은 다음과 같은 반응식으로 얻어졌다. 2-히드록시-[1,4]나프토퀴논과 포타슘카보네이트(K2CO3)를 아세토니트릴에 용해한 후, 저온수조로 냉각하고 알킬할라이드를 적당한 당량비로 천천히 적하하여 히드록시기와 에테르(ether) 반응을 통하여 얻어질 수 있다. 상기 반응식에서 R은 C1~10의 포화 또는 불포화된 알킬기로서 직쇄형 또는 분지쇄형 모두 가능하다. 상기 화합물인 2-히드록시-[1,4]나프토퀴논(2-hydroxynaphthoquinone)은 배양된 쥐의 멜라노마 세포에 대하여 하이드로퀴논과 대등한 멜라닌 생성 억제효과를 보였다. 하이드로퀴논은 저농도에서 강력한 멜라닌 생성 억제효과를 보이지만 상기 화합물들은 보다 낮은 농도에서도 세포독성을 나타내지 않으며 하이드로퀴논보다 높은 멜라닌 생성 억제 효과를 보였다.

• Journal of environmental and Sanitary engineering
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• v.14 no.3
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• pp.54-62
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• 1999

2,4-Dichlorophenol was known pollutants caused by the endocrine disruptor into the refractory substances of environment and this is difficult to be degradable by conventional methods. Therefore, a considerable interest has been devoted to developing new process where 2,4-Dichlorophenol can easily decomposed. In this study, the series of ultrasonic irradiation for removal of 2,4-Dichlorophenol has been selected as a model reaction in the batch reactor system in order to obtain the basic data investigate the influence of various experimental parameters such as concentration, pH, reaction temperature, acoustic intensity. The products obtained form the ultrasonic irradiation were analysed by GC/MS and HPLC. The formation of $H_2O_2$, a well-known the strong oxidant was found proportionally to increase with irradiation time. The intermediates of ultrasonic irradiation of 2,4-Dichlorophenol were identified as HCl, catechol, hydroquinone, o,p-benzoquinone, muconic acid, and maleic acid. The final products of this was $CO_2$ and $H_2O$. As the decomposition of 2,4-Dichlorophenol proceeds by the ultrasonic irradiation, the pH of 2,4-Dichlorophenol containing aqueous solution increases slowly, The decomposition of 2,4-Dichlorophenol was found to be occured fast in the basic medium. In general, the rate of reaction is proportional to the reaction temperature obeying the Arrhenius' law. However, in the ultrasonic irradiation, this suggests as the reaction temperature increase the decomposition rate of the reactant decreases. This result meant that the increase of reaction temperature due to the increase of vapor pressure of water accelerated the decrease of acoustic intensity which was can be proportional to the decomposition rae of these compounds. It was found that more than 80% of phenol solution was removed within hours in all reaction conditions. The reaction order in the degradation of the 2,4-Dichlorophenol compounds was verified as the Pseude-first order. From the fore-mentioned results, it can be concluded that the refractory organic compounds caused by endocrine disruptor as 2,4-dichlorophenol could be removed by the ultrasonic irradiation with radicals, such as $H{\;}{\cdot}{\;}and{\;}OH{\;}{\cdot}$ radical causing the high increase of pressure and temperature. Finally, it apeared that the technology using ultrasonic irradiation can be applied to the treatment of refractory substances caused by endocrine disruptor which are difficult to be decomposed by the conventional methods.