• Title/Summary/Keyword: 3-OH-Phenanthrene

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Molecular Characteristics of Pseudomonas rhodesiae Strain KK1 in Response to Phenanthrene

  • Kahng, Hyung-Yeel;Nam, Kyoung-Phile
    • Journal of Microbiology and Biotechnology
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    • v.12 no.5
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    • pp.729-734
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    • 2002
  • Radiorespirometric analysis revealed that Pseudomonas sp. strain KKI isolated from a soil contaminated with petroleum hydrocarbons was able to catabolize polycyclic aromatic hydrocarbons such as phenanthrene and naphthalene. The rate and extent of phenanthrene mineralization was markedly enhanced when the cells were pregrown on either naphthalene or phenanthrene, compared to the cells grown on universal carbon sources (i.e., TSA medium). Deduced amino acid sequence of the Rieske-type iron-sulfur center of a putative phenanthrene dioxygenase (PhnAl) obtained from the strain KKI shared significant homology with DxnAl (dioxin dioxygenase) from Spingomonas sp. RW1, BphA1b (biphenyl dioxygenase) from Spingomonas aromaticivorans F199, and PhnAc (phenanthrene diokygenase) from Burkholderia sp. RP007 or Alcaligenes faecalis AFK2. Northern hybridization using the dioxygenase gene fragment cloned from KKI showed that the expression of the putative phn dioxygenase gene reached the highest level in cells grown in the minimal medium containing phenanthrene and $KNO_3$, and the expression of the phn gene was repressed in cells grown with glucose. In addition to the metabolic change, phospholipid ester-linked fatty acids (PLFA) analysis revealed that the total cellular fatty acid composition of KKI was significantly changed in response to phenanthrene. Fatty acids such as 14:0, 16:0 3OH, 17:0 cyclo, 18:1$\omega$7c, 19:0 cyclo increased in phenanthrene-exposed cells, while fatty acids such as 10:0 3OH, 12:0, 12:0 2OH, 12:0 3OH, 16:1$\omega$7c, 15:0 iso 2OH, 16:0, 18:1$\omega$6c, 18:0 decreased.

A DFT Study for the Reaction Pathway(s) of Polycyclic Aromatic Hydrocarbons I: Phenanthrene Degradation with two OH Radicals (다고리 방향족 탄화수소의 반응 경로에 대한 DFT 연구 I: 2개의 OH 라디칼에 의한 페난트렌의 분해 반응)

  • Lee, Min-Joo;Lee, Byung-Dae
    • Journal of the Korean Chemical Society
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    • v.65 no.1
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    • pp.9-14
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    • 2021
  • In this study, the DFT calculation was performed using the B3LYP/6-31G(d,p) basis sets for the reaction process in which phenanthrene decomposes due to the chain reaction of two OH radicals on phenanthrene in the gaseous state of 298 K at 1 atm. As a result of the calculation, even when two OH radicals act on phenanthrene in a chain, the reaction for producing phenanthren-9-ol is predicted to be more advantageous than the reaction for producing phenanthren-1-ol. On the other hand, it was predicted that the OH addition process at room temperature would be advantageous for the priority of the OH addition and H abstraction process.

EFFECTS OF SURFACTANTS ON THE FENTON DEGRADATION OF PHENANTHRENE IN CONTAMINATED SEDIMENTS

  • Jee, Sang-Hyun;Ko, Seok-Oh;Jang, Hae-Nam
    • Environmental Engineering Research
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    • v.10 no.3
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    • pp.138-143
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    • 2005
  • Laboratory batch experiments were conducted to evaluate the Fenton degradation rates of phenanthrene. Fenton reactions for the degradation of phenanthrene were carried out with aqueous and slurry phase, to investigate the effects of sorption of phenanthrene onto solid phase. Various types of surfactants and electrolyte solutions were used to evaluate the effects on the phenanthrene degradation rates by Fenton's reaction. A maximum 90% removal of phenanthrene was achieved in aqueous phase with 0.9% of $H_2O_2$ and 300 mg/L of $Fe^{2+}$ at pH 3. In aqueous phase reaction, inhibitory effects of synthetic surfactants on the removal of phenanthrene were observed, implying that surfactant molecules acted as strong scavenger of hydroxyl radicals. However, use of $carboxymethyl-{\beta}-cyclodextrin$ (CMCD), natural surfactant, showed a slight enhancement in the degradation of phenanthrene. It was considered that reactive radicals formed at ternary complex were located in close proximity to phenanthrene partitioned into CMCD cavities. It was also show that Fenton degradation of phenanthrene were greatly enhanced by addition of NaCl, indicating that potent radical ion ($OCI^-$) played an important role in the phenanthrene degradation, although chloride ion might be acted as scavenger of radicals at low concentrations. Phenanthrene in slurry phase was resistant to Fenton degradation. It might be due to the fact that free radicals were mostly reacting with dissolved species rather than with sorbed phenanthrene. Even though synthetic surfactants were added to increase the phenanthrene concentration in dissolved phase, low degradation efficiency was obtained because of the scavenging of radicals by surfactants molecules. However, use of CMCD in slurry phase, showed a slight enhancement in the phenanthrene degradation. As an alternative, use of Fenton reaction with CMCD could be considered to increase the degradation rates of phenanthrene desorbed from solid phase.

Biodegradation of Phenanthrene by Sphingomonsa sp. Strain KH3-2

  • Shin, Su-Kyuong;Oh, Young-Sook;Kim, Sang-Jin
    • Journal of Microbiology
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    • v.37 no.4
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    • pp.185-192
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    • 1999
  • A phenanthrene-degrading bacterium was isolated from an oil-spilled intertidal sediment sample and identified as Sphingomonas sp. KH3-2. The strain degraded polycyclic aromatic compounds such naphthalene, fluorene, biphenyl, and dibenzothiophene. When strain KH3-2 was cultured for 28 days at 25C, a total of 500 ppm of phenanthrene was degrated with a concomitant production of biomass and Folin-Ciocalteau reactive aromatic intermediates. Analysis of intermediates during phenanthrene degradation using high-performance liquid chromatography and gas chromatography/mass spectrometry indicated that Sphingomonas sp. KH3-2 primarily degrades phenanthrene to 1-hydroxy-2-naphthoic acid (1H2NA) and further metabolizes 1H2NA through the degradation pathway of naphthalene.

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1-OH-Pyrene and 3-OH-Phenanthrene in Urine Show Good Relationship with their Parent Polycyclic Aromatic Hydrocarbons in Muscle in Dairy Cattle

  • Kang, Hwan-Goo;Jeong, Sang-Hee
    • Toxicological Research
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    • v.27 no.1
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    • pp.15-18
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    • 2011
  • The toxicities of phenanthrene (PH) and pyrene (PY) are less than benzo(a)pyrene (BaP), but both compounds are found in higher concentrations in the air, feed, and food. Most PAHs are metabolized to hydroxylated compounds by the hepatic cytochrome P450 monooxigenases system. Metabolites are excreted into urine and feces. We determined concentrations of PH, PY and BaP in muscle and hydroxylated metabolites, 3-OH-PH, 1-OH-PY, and 3-OH-BaP, respectively, in urine from dairy cattle (n = 24). We also evaluated the relationship between parent compounds in muscle and their metabolites in urine. Concentrations of PH and PY in muscle ranged from 0.7~4.8 ng/g ($1.8{\pm}1.7$) and 0.4~4.1 ng/g ($1.2{\pm}1.2$), respectively. Concentrations of 3-OH-PH and 1-OH-PY in urine ranged from 0.1~5.9 ng/ml ($2.9{\pm}3.7$) and 0.5~3.6 ng/ml ($1.9{\pm}2.3$), respectively. Correlation coefficient for PY concentration in muscle versus 1-OH-PY in urine was 0.657 and for PH concentration in muscle versus 3-OH-PH in urine was 0.579. Coefficient determination for PY and PH concentrations in muscle was 0.886 and for 1-OH-PY and 3-OH-PH in urine was 0.834. This study suggests that 1-OH-PY and 3-OH-PH could be used as biomarkers for PAHs exposure in dairy cattle.

Ozone Oxidation of PAHs in the Presence of Soil (I): Ozonation of Soil Slurry Phase (Ozone에 의한 PAHs 오염토양 복원 연구(I): 토양슬러리상 오존 산화)

  • Lim, Hyung-Nam;Kim, Ji-Yeon;Choi, Heechul
    • Journal of Korean Society of Environmental Engineers
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    • v.22 no.5
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    • pp.869-877
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    • 2000
  • A mechanism of ozonation of simulated soil slurry contaminated by phenanthrene and benzo[a]pyrene has been studied under various conditions. The effects of soil media(BS, S, GB), radical scavenger, ozone input ratio(0.17~0.73mg/min), bicarbonate ion, and humic acid were investigated, BS showed the highest removal efficiency in media tested. The generation of OH-radical via the catalytic decomposition of ozone on active sites of the natural sand was confirmed by OH-radical scavenger experiments. The enhanced removal efficiency by OH-radical was indirectly quantified to be about 22%. As initial concentration of humic acid(as sodium salt) was increased, pseudo first-order rate constant ($k_o$) of phenanthrene was decreased from $1.37{\times}10^{-2}s^{-1}$ to $0.53{\times}10^{-2}s^{-1}$. The amount of ozone required to oxidize 80% of the initial mass of phenanthrene(10mg/kg) and benzo[a]pyrene(10mg/kg) was 67.2mg/kg-soil and 48.0mg/kg-soil, respectively.

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Identification of a Radical Decomposition Pathway(s) of Polycyclic Aromatic Hydrocarbon by the Vibrational Frequency Calculations with DFT Method (DFT법에 의한 진동 운동 진동수 계산을 통한 다고리 방향족 탄화수소의 라디칼 분해 경로 동정)

  • Lee, Byung-Dae;Ha, Kwanga;Lee, Min-Joo
    • Journal of the Korean Chemical Society
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    • v.62 no.5
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    • pp.344-351
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    • 2018
  • The IR spectra of gaseous phenanthrene, phenathrenols, phenanthrenyl radicals, and hydroxylphenanthrene radicals have been obtained using the BLYP/6-311++G(d,p) method. A comparison of these spectra shows that the measurements of IR spectra can be valuable to identify the reaction pathway(s) of the phenanthrene decomposition reaction by ${\cdot}OH$. We have found that the H atom abstraction reaction process can be easily identifiable from the $650-850cm^{-1}$ (CH out-of-plane bending) region and the ${\cdot}OH$ addition reaction process from the CH stretching and bending modes region of IR spectra. In addition, the calculated IR spectra of all five phenanthren-n-ols (n = 1, 2, 3, 4, 9) have also given in this work.

Effects of pH Control Methods on Removal Efficiency in Electrokinetic Bioremediation of Phenanthrene-contaminated Soil (Phenanthrene-오염토양의 동전기 생물학적 복원에서 pH 조절방법이 제거효율에 미치는 영향)

  • Kim, Sang-Joon;Park, Ji-Yeon;Lee, You-Jin;Yang, Ji-Won
    • KSBB Journal
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    • v.21 no.3
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    • pp.181-187
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    • 2006
  • In this study, problems related with pH control in electrokinetic(EK) bioremediation of phenanthrene contaminated soil were observed, and the effects of pH control methods on the removal efficiency were investigated to search a further application strategy. In a preliminary experiment, it was found out by flask cultivation that a certain sulfate concentration was needed to degrade phenanthrene well using Sphingomonas sp. 3Y. However, when $MgSO_4$ was used as sulfate source in EK bioremediation, the bacterial activity reduced seriously due to the abrupt decrease of pHs in soil and bioreactor by the combination of magnesium and hydroxyl ions. When another strong buffering compound was used to control the pH problem, the good maintenance of the bacterial activity and pHs could be observed, but the removal efficiency decreased largely. When a low concentration of $MgSO_4$ was added, the removal efficiency decreased somewhat in spite of the good maintenance of neutral pHs. With the addition of NaOH as a neutralizing agent, the removal efficiency also decreased because of the increase of soil pH. Consequently the selection of electrolyte composition was a very important factor in EK bioremediation and some sulfate sources suitable for both bacterial activity and contaminant degradation should be investigated.

Removal of Semi-volatile Soil Organic Contaminants with Microwave and Additives (극초단파(마이크로파)와 첨가제를 이용한 오염토양 내 준휘발성 유기오염물질 제거)

  • Jeong, Sangjo;Choi, Hyungjin
    • Journal of Soil and Groundwater Environment
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    • v.18 no.1
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    • pp.67-77
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    • 2013
  • To improve the energy efficiency of conventional thermal treatment, soil remediation with microwave has been studied. In this study, the remediation efficiency of contaminated soil with semi-volatile organic contaminants were evaluated with microwave oven and several additives such as water, formic acid, iron powder, sodium hydroxide (NaOH) solution, and activated carbon. For the experiment, loamy sand and sandy loam collected from Imjin river flood plain were intentionally contaminated with hexachlorobenzene and phenanthrene, respectively. The contaminated soils were treated with microwave facility and the mass removals of organic contaminants from soils were evaluated. Among additives that were added to increase the remediation efficiency, activated carbon and NaOH solution were more effective than water, iron powder, and formic acid. When 10 g of hexachlorobenzene (142.4 mg/kg-soil) or phenanthrene (2,138.8 mg/kg-soil) contaminated soil that mixed with 0.5 g iron powder, 0.5 g activated carbon and 1 ml 6.25 M NaOH solution were treated with microwave for 3 minutes, more than 95% of contaminants were removed. The degradation of hexachlorobenzene during microwave treatments with additives was confirmed by the detection of pentachlorobenzene and tetrachlorobenzene. Naphthalene and phenol were also detected as degradation products of phenanthrene during microwave treatment with additives. The results showed that adding a suitable amount of additives for microwave treatments fairly increased the efficiency of removing semi-volatile soil organic contaminants.

Studies on the Cytotoxic Constituent of Saururus chinensis$(L_{OUR.})\;B_{AILL.}$ (삼백초의 세포독성 성분연구)

  • Park, Si-Kyung;Oh, Gab-Jin;Bae, Choon-Il;Kim, Hyun-Jong;Han, Wan-Sik;Chung, Sun-Gan;Cho, Eui-Whan
    • YAKHAK HOEJI
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    • v.41 no.6
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    • pp.704-708
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    • 1997
  • In our search for bioactive natural products with antitumor activity, we have valuated various extracts of Saururi Herba (Saururaceae), which has been used in traditional medici ne for edema, beriberi, jaundice, turbid urine, carbuncle and furuncle. The hexane extract of the aerial part of this plant was found to show a potent cytotoxicity against several kinds of cultured human solid tumor cell lines (AGS, A549, HCT15, SKOV3, HEP-3B) in vitro. Using cytotoxicity-guided chromatographic separation of the hexane extract, cytotoxic constituent: 10-aminomethyl-3-hydroxy-4-methoxyphenanthrene-carboxylic acid lactam, was isolated and structurally identified by physico-chemical properties and spectroscopic evidences.

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