• Title/Summary/Keyword: oxidative cleavage

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1-Methylimidazolium Chlorochromate. A New Efficient Oxidizing Agent for Oxidation of Alcohols and Oxidative Cleavage of Oximes

  • Kim, Sung-Gak;Chang, Heung
    • Bulletin of the Korean Chemical Society
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    • v.8 no.3
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    • pp.183-185
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    • 1987
  • 1-Methylimidazolium chlorochromate was prepared by the addition of 1-methylimidazole into a solution of chromic trioxide in 6M hydrochloric acid and obtained in high yield as bright yellow crystalline solids. The reagent was found to be very effective for the oxidation of alcohols and the oxidative cleavage of oximes to the corresponding carbonyl compounds.

Formation of Oxidative Cleavage from Phytofluene by Autoxidation (자동산화에 의한 Phytofluene으로부터 산화개열산물의 생성)

  • 김선재
    • Journal of the Korean Society of Food Science and Nutrition
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    • v.29 no.4
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    • pp.568-574
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    • 2000
  • Phytofluene was subjected to ozonolysis in ice-cold dichloromethane. The ozonolysis products were fractionated with a silica column and the carbonyl fraction was analyzed by ODS-HPLC with a photodiode array detector. Phytofluene was solubilized in 5% tween 40, and then oxidized by incubating under dim yellow light at 37$^{\circ}C$, 24 hr with continuous shaking. Carbonyl compound and acidic compound were produced. In comparison with autoxidation and ozonolysis, each compound showed the same retention time and UV-vis spectra were identical to the reference cleavage products prepared by ozeonolysis of phytofluene. Absorption spectrum of acidic compound was similar to that of standard 4,5-didehydrogeranyl geranyl acid which is known to possess biological activity. Thus, eccentric cleavage of phytofluene was confirmed to occur in vitro under oxidation condition.

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Formation of Oxidative Cleavage Products from Lycopene (Lycopene으로부터 산화개열산물의 생성)

  • Kim, Seon-Jae
    • Korean Journal of Food Science and Technology
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    • v.32 no.6
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    • pp.1227-1233
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    • 2000
  • Lycopene was subjected to ozonolysis in ice-cold dichloromethane. The ozonolysis products were fractionated with a silica column and the carbonyl fraction was analyzed by ODS-HPLC with a photodiode array detector and by LC-MS. UV-vis spectra and $[M+H]^+$ of the carbonyl compound peaks showed clearly that acycloretinal, apo-14'-lycopenal, apo-12'-lycopenal, apo-10'-lycopenal, apo-8'-lycopenal and apo-6'-lycopenal were formed by ozonolysis of lycopene. Lycopene was solubilized in toluene and aqueous Tween 40, and then oxidized by incubating at $37^{\circ}C$ under atmospheric oxygen. Carbonyl compounds were produced. In comparison with autoxidation and ozonolysis, each compound showed the same retention time and UV-vis spectra are identical to the reference cleavage products prepared by ozonolysis of lycopene. Thus, eccentric cleavage of lycopene was confirmed to occur in vitro under oxidation condition.

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Oxidative Cleavage Products Derived from Phytofluene by Pig Liver Homogenate

  • Kim, Seon-Jae;Kim, Hag-Lyeol;Jang, Hong-Gi
    • Food Science and Biotechnology
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    • v.14 no.3
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    • pp.424-427
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    • 2005
  • The cleavage products formed by the autoxidation of phytofluene were evaluated in order to elucidate possible oxidation products of phytofluene in the oxidative condition. Among a number of oxidation products formed, the following five in the carbonyl compound fraction were identified: 6, 10, 14-trimethylpentadeca-3,5,9,13-tetraen-2-one, phytapentaenal, 5,9,13,17-tetramethyloctadeca-2,4,6,8,12,16-hexaenal, 5,9,13,17-tetramethyloctadeca-2,4,8,12, 16-pentaenal, 2,7,11,15,19-pentamethylicosa-2,4,6,10,14,18-hexaenal and 4,9,13,17,21-pentamethyldocosa-2,4,6,8,12,16,20-heptaenal. In addition, 4,5-didehydrogeranyl geranoic acid was formed by the autoxidation of phytofluene in liposomal suspension. The pig liver homogenate was able to convert phytapentaenal to 4,5-didehydrogeranyl geranoic acid, in a manner comparable to the conversion of all-trans-retinal to all-trans-retinoic acid. These results suggest firstly that phytofluene is cleaved into a series of long-chain and short-chain carbonyl compounds under the oxidative condition in vitro and secondly that phytapentaenal is further enzymatically converted to 4,5-didehydrogeranyl geranoic acid.

Antioxidant Activities and Inhibitory Effect on Oxidative DNA Damage of extracts from Abeliophylli distichi Folium (미선나무 잎 추출물의 항산화 및 산화적 DNA 손상억제 활성)

  • Park, Jae-Ho
    • The Korea Journal of Herbology
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    • v.26 no.4
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    • pp.95-99
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    • 2011
  • Objective : In this study, we demonstrate the protective effect on oxidative DNA damage of leaf extracts from Abeliophylli distichi Folium via its antioxidant activity for the establishment of new value for the herbal medicine. Methods : Abeliophylli distichi Folium leaves were extracted with hot-water and ethylacetate (EtOAC). The 1,1-diphenyl-2- picrylhydrazyl (DPPH) radical and hydroxyl scavenging assay and $Fe^{2+}$ chelating assay were performed for antioxidative effect and ${\varphi}$X-174 RF I DNA cleavage assay and intracellular DNA damage assay were used for inhibitory effect of intracellular DNA damage. Results : In DPPH, Hydroxyl radical scavenging activity and $Fe^{2+}$ chelating activity of EtOAC extracts were 94.72%, 62.88%, 41.13%, and hot-water extracts were 88.86%, 56.7%, 37.4% at 200 ${\mu}g/m{\ell}$, respectively. Also, those extracts showed protective effect of DNA damage against the oxidative stress. Conclusion : These results indicated that the leaf extracts of Abeliophylli distichi Folium can be used as a natural antioxidants, which effectively inhibits the oxidative DNA damage.

DNA Cleavage Induced by the Reaction of Salsolinol with Cu,Zn-Superoxide Dismutase

  • Kang, Jung-Hoon
    • Bulletin of the Korean Chemical Society
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    • v.28 no.12
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    • pp.2329-2332
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    • 2007
  • Salsolinol, endogenous neurotoxin, is known to be involved in the pathogenesis of Parkinson's disease (PD). In the present study, we have investigated the oxidative damage of DNA induced by the reaction of salsolinol with Cu,Zn-SOD. When plasmid DNA incubated with salsolinol and Cu,Zn-SOD, DNA cleavage was proportional to the concentrations of salsolinol and Cu,Zn-SOD. The salsolinol/Cu,Zn-SOD system-mediated DNA cleavage was significantly inhibited by radical scavengers such as mannitol, ethanol and thiourea. These results indicated that free radicals might participate in DNA cleavage by the salsolinol/Cu,Zn-SOD system. Spectrophotometric study using a thiobarbituric acid showed that hydroxyl radical formation was proportional to the concentration of salsolinol and was inhibited by radical scavengers. These results indicated that hydroxyl radical generated in the reaction of salsolinol with Cu,Zn-SOD was implicated in the DNA cleavage. Catalase and copper chelators inhibited DNA cleavage and the production of hydroxyl radicals. These results suggest that DNA cleavage is mediated in the reaction of salsolinol with Cu,Zn-SOD via the generation of hydroxyl radical by a combination of the oxidation reaction of salsolinol and Fenton-like reaction of free copper ions released from oxidatively damaged SOD.

Antioxidant Activities and Inhibitory Effect on Oxidative DNA Damage of Nelumbinis Semen Extracts (연자육 추출물의 항산화 및 산화적 DNA 손상억제 활성)

  • Park, Jae-Ho;Lee, Byung-Gu;Byun, Gwang-In;Kim, Do-Wan
    • The Korea Journal of Herbology
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    • v.25 no.4
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    • pp.55-59
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    • 2010
  • Objective : This study was conducted to investigate the antioxidant activity and inhibitory effect on oxidative DNA damage of Nelumbinis Semen Extracts Methods : Nelumbins semen were extracted with hot-water and ethylacetate (EtOAC). The 1,1-diphenyl-2-picrylhydrazyl (DPPH) and hydroxyl radical scavenging assay and $Fe^{2+}$ chelating assay were performed for antioxidative effect and ${\phi}X$-174 RF I DNA cleavage assay and intracellular DNA damage assay were used for inhibitory effect on intracellular DNA damage. Results : In DPPH, Hydroxyl radical scavenging activity and $Fe^{2+}$ chelating activity of EtOAC extracts were 96.22%, 53.53%, 64.72%, while those of hot-water extracts were 20.86%, 10.72%, 29.74% at $200{\mu}g/m{\ell}$, respectively. In ${\phi}X$-174 RF I plasmid DNA cleavage assay, the protective effects of EtOAC and hot-water extracts against oxidative DNA damage were 76% and 6% at $200{\mu}g/m{\ell}$, respectively. Conclusion : These results indicated that the seed extracts of Nelumbo nucifera can be used as a natural antioxidants, which effectively inhibits the oxidative DNA damage.