• Title/Summary/Keyword: 4-naphthoquinone

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Color Alteration and Acaricidal Activity of Juglone Isolated from Caesalpinia sappan Heartwoods Against Dermatophagoides spp.

  • Lee, Chi-Hoon;Lee, Hoi-Seon
    • Journal of Microbiology and Biotechnology
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    • v.16 no.10
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    • pp.1591-1596
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    • 2006
  • Acaricidal effects of materials derived from Caesalpinia sappan heartwoods against Dermatophagoides farinae and D. pteronyssinus were assessed and compared with those evidenced by commercial benzyl benzoate and DEET. The observed responses varied according to dosage and mite species. The $LD_{50}$ values of the methanol extracts derived from C. sappan heartwoods were 6.13 and $5.44{\mu}g/cm^3$ against D. farinae and D. pteronyssinus, respectively. Furthermore, the ethyl acetate fraction derived from the methanol extract was approximately 8.71 more toxic than DEET against D. farinae, and 4.73 times more toxic against D. pteronyssinus. The biologically active constituent from the ethyl acetate fraction of C. sappan heartwood extract was purified via silica gel chromatography and high-performance liquid chromatography. The structure of the acaricidal component was analyzed by $GC-MS,\;^1H-NMR,\;^{13}C-NMR,\;^1H-^{13}C\;COSY-NMR$, and DEPT-NMR spectroscopy, and identified as juglone (5-hydroxy-l,4-naphthoquinone). Based on the $LD_{50}$ values of juglone and its derivatives, the most toxic compound against D. farinae was juglone ($0.076{\mu}g/cm^3$), followed by benzyl benzoate ($9.143{\mu}g/cm^3$) and 2methyl-l,4-naphthoquinone ($40.0{\mu}g/cm^3$). These results indicate that the acaricidal activity of C. sappan heartwoods is likely to be the result of the effects of juglone. Additionally, juglone treatment was shown to effect a change in the color of the cuticles of house dust mites, from colorless-transparent to dark brownish-black. Accordingly, as a naturally occurring acaricidal agent, C. sappan heartwood-derived juglone should prove to be quite 'useful as a potential control agent, lead compound, and house dust mite indicator.

Synthesis of 3-Methyl-2,3-dihydrobenz(f)indole-2,4,9-trione Derivatives (3-메칠-2,3-디히드로 벤즈(f)인돌-2,4,9-트리온 유도체의 합성)

  • Suh, Myung-Eun;Jeoung, Hyun-Jung
    • YAKHAK HOEJI
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    • v.40 no.3
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    • pp.273-278
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    • 1996
  • The 2,3-dichloro-1,4-naphthoquinone was reacted with diethyl methylmalonate and sodium amide in the toluene to yield 3-chloro-2-(1-methyl-1-diethoxycarbonyl)-methyl-1,4-naphthoq uinone(I). When this compound I was reacted with some alkylamines (methylamine, ethylamine, ethanolamine, 2-bromoethylamine, propylamine, isopropylamine, cyclohexylamine, benzylamine, 4-piperidylmethylamine), 3-methyl-2,3-dihydrobenz(f)indole-2,4,9-trione derivatives(IIa-i) were obtained via intramolecular cyclization.

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Study on Constituents of Paulownia tomentosa Stem(II) -synthesis of new furanquinone compound- (참오동나무 줄기의 성분연구(II) -새로운 furanquinone계 화합물의 합성-)

  • Jang, Seong-Ki;Park, You-Mie;Kim, Yeon-Soo;Kang, Kyung-Hwan;Kim, Yang-Suk;Kim, Bak-Kwang
    • YAKHAK HOEJI
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    • v.35 no.6
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    • pp.483-485
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    • 1991
  • A furanquinone substance(methyl 5-hydroxy-dinaphtho [1,2-2',3'] furan-7,12-dione-6-carboxylate) which has been isolated from the methanol extract of Paulownia tomentosa stem was synthesized by condensing 2,3-dichloro-1,4-naphthoquinone with methyl 1,4-dihydroxy-naphthalene-2-carboxylate in pyridine and identified by NMR, MS, UV, IR etc.

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Synthesis and Evaluation of Antitumor Activity of 2- and 6-[(1,3- Benzothiazol-2-yl)aminomethyl]-5,8-dimethoxy-1,4-naphthoquinone Derivatives

  • Chung, Yong-Seog;Shin, Young-Kook;Zhan, Chang-Guo;Lee, Sung-Duck;Cho, Hoon
    • Archives of Pharmacal Research
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    • v.27 no.9
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    • pp.893-900
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    • 2004
  • 2- or 6-Substituted BZT-N derivatives were synthesized, and their cytotoxic activity against can-cer L1210 and SNU-1 cells was examined. The antitumor action was also assessed in mice bearing S-180 cells in peritoneal cavity. In a comparison, it was found that 6-substituted BZT-N derivatives exhibited higher potencies in both bioactivities than 2-substituted BZT-N derivatives against L1210 cells in in vitro and S-180 in vitro tests exception of compound 36. Interestingly, it was observed that 2-substituted compound 36, which has methyl group at RI position, exhib-ited a better antitumor activity than 6-substituted compounds against L1210 and SNU-1 in vitro. The EDso value of 2-substituted compound 36 against L1210 was found to be comparable to the EDso value of adriamycin and was even better against the solid cancer cell line SNU-1. It was also observed that 2-substituted compound 36 showed better antitumor activity in mice bearing S-180 cells in the peritoneal cavity. The T/C (%) value of 2-substituted compound 36 was simi-lar to that of adriamycin. Quantitative structure-activity relationship (QSAR) tests reveal that the experimental E $D_{50}$ values against SNU-1 closely correlate with both the calculated HOMO ener-gies ( $E_{HOMO}$) and the measured H-NMR chemical shift of 3-H ($\delta$$_{H}$). The results suggests that a compound having higher $E_{HOMO}$ and $\delta$$_{H}$ values usually should have a lower E $D_{50}$ (SNU-1) value.lue.lue.lue.

Anti-Helicobacter pylori Compounds from Polygonum cuspidatum

  • Khalil, Atif Ali Khan;Park, Woo Sung;Kim, Hye Jin;Akter, Kazi Marjahan;Ahn, Mi-Jeong
    • Natural Product Sciences
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    • v.22 no.3
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    • pp.220-224
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    • 2016
  • Anti-Helicobacter pylori activity guided fractionation led to the isolation of five anthraquinones, two stilbenes and one naphthoquinone from the EtOAc fraction of Polygonum cuspidatum, using silica gel column chromatography, Sephadex-LH20, MPLC and recrystallization. The chemical structures were identified to be physcion (1), emodin (2), anthraglycoside B (3), trans-resveratrol (4), anthraglycoside A (5), polydatin (6), 2-methoxy-6-acetyl-7-methyljuglone (7) and citreorosein (8) by UV, $^1H$-NMR, $^{13}C$-NMR and mass spectrometry. Anti-Helicobacter pylori activity including MIC values of each compound was evaluated. All of the isolates exhibited anti-H. pylori activity of which MIC values were lower than that of a positive control, quercetin. Compounds 2 and 7 showed potent growth inhibitory activity. Especially, a naphthoquinone, compound 7 displayed most potent antibacterial activity with $MIC_{50}$ value of $0.30{\mu}M$ and $MIC_{90}$ value of $0.39{\mu}M$. Although anti-H. pylori activity of this plant was previously reported, this is the first report on that of compounds isolated from this species. From these findings, P. cuspidatum roots or its isolates may be useful for H. pylori infection and further study is needed to elucidate mechanism of action.

Biochemical Properties of NAD(P)H-Quinone Oxidoreductase from Saccharomyces cerevisiae

  • Kim, Kyung-Soon;Suk, Hee-Won
    • BMB Reports
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    • v.32 no.2
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    • pp.127-132
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    • 1999
  • The NAD(P)H-quinone oxidoreductase (EC 1. 6. 99. 2) was purified from S. cerevisiae. The native molecular weight of the enzyme is approximately 111 kDa and is composed of five identical subunits with molecular weights of 22 kDa each. The optimum pH of the enzyme is pH 6.0 with 1,4-benzoquinone as a substrate. The apparent $k_m$ for 1,4-benzoquinone and 1,4- naphthoquinone are 1.3 mM and $14.3\;{\mu}M$, respectively. Its activity is greatly inhibited by $Cu^{2+}$ and $Hg^{2+}$ ions, nitrofurantoin, dicumarol, and Cibacron blue 3GA. The purified NAD(P)H-quinone oxidoreductase was found capable of reducing aromatic nitroso compounds as well as a variety of quinones, and can utilize either NADH or NADPH as a source of reducing equivalents. The nitroso reductase activity of the purified NAD(P)H-quinone oxidoreductase is strongly inhibited by dicumarol.

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Application of Single Cell Gel Electrophoresis for Detection of DNA Single Strand Breaks in DNA of Fish Blood Cell (어류혈구세포에 있어서 Single Cell Gel Electrophoresis를 응용한 DNA Single Strand Breack의 측정)

  • KIM Gi Beum;LEE Richard F.;MARUYA Keith A.
    • Korean Journal of Fisheries and Aquatic Sciences
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    • v.36 no.4
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    • pp.346-351
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    • 2003
  • Single-cell gel electrophoresis (comet assay) was used to detect DNA single strand break in blood cells from several marine fish species. Three fish species were collected from Georgia coastal area. Mummichog, Fundulus heteroclitus showed higher DNA damage than sea bass, Lateolabrax japonicus and trout, Oncorhynchus masou masou under the same experimental conditions. Mummichogs had more alkaline-labile sites on their DNA than other fish species. The comet assay with mummichog blood cells at pH 12.5 showed a dose-response curve with the increasing concentrations of hydrogen peroxide. While the isolated leucocytes showed no increase of DNA damage after in vitro exposure to 2-methyl-1,4-naphthoquinone (MNQ), erythrocytes showed dose-dependent DNA damage. These results indicate that the comet assay can be applied successfully as a bioassay using erythrocyte for environmental monitoring.

Antifungal activities of 2-arylthio-,2-arylthio-5-methoxy-,2,3-bisarylthio-juglones and 2,3-bisarylthio-5,8-dimethoxy-1 A-naphthoquinones

  • Shim, Ju-Yeon;You, Hea-Jung;Choi, Ko-Un;Choi, Ik-Hwa;Chae, Mi-Jin;Ryu, Chung-Kyu
    • Proceedings of the PSK Conference
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    • 2002.10a
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    • pp.350.3-351
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    • 2002
  • 2-Arylthio-, 2-arylthio-5-methoxy-, 2, 3-bisarylthio-juglones and 2, 3-bisarylthio-5, 8-dimethoxy-1, 4-naphthoquinones were newly systhesized for the evaluation of antifungal activities. These derivatives were prepared by methylation of juglone and 2, 3-dichloro-5, 8-dihydroxy-1, 4-naphthoquinone. and by resioselective nucleophilic subsitution with arylthiols. All compounds were tested in vitro for their growth inhibitory activities against pathogenic fungi by the standard method. The MIC values were determined by comparison to flucytosine as a fungicidal standard agent. In general. In general. most juglone derivatives shows in vitro antifungal activities. Among them. 2-arylthio-5-methoxy-juglones showed most potent antifungal activities against all pathogenic fungi.

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