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Chemical Compound Review

Regianin     5-hydroxynaphthalene-1,4-dione

Synonyms: Juglane, Jugnlon, juglone, Akhnot, Iuglon, ...
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Disease relevance of juglone


High impact information on juglone


Chemical compound and disease context of juglone


Biological context of juglone


Anatomical context of juglone

  • As a control, keratinocytes loaded with DCFH were incubated in the dark with either exogenously added H(2)O(2) or 5-hydroxy-1,4-naphthoquinone (juglone), which redox cycles to generate superoxide (and H(2)O(2)) [15].
  • An antenna-based origin for the quenching was verified experimentally by the observation that addition of the antenna quencher 5-hydroxy-1,4-naphthoquinone to thylakoids under Fm conditions resulted in decay kinetics and modeled kinetic parameters very similar to those observed under Fsat conditions in the absence of added quinone [16].
  • Furthermore, juglone inhibits mRNA synthesis in human fibroblasts in a dose-dependent manner [13].
  • Blocking of n-type K+ channels by juglone is in concert with its depolarizing effect on human lymphocytes [12].
  • The two zinc porphyrins were capable of mediating CT degradation at rates comparable to those observed with the M. thermophila exudates; however, juglone was only capable of very slow CT transformation [17].

Associations of juglone with other chemical compounds


Gene context of juglone


Analytical, diagnostic and therapeutic context of juglone


  1. Effect of hydroxy substituent position on 1,4-naphthoquinone toxicity to rat hepatocytes. Ollinger, K., Brunmark, A. J. Biol. Chem. (1991) [Pubmed]
  2. Selective inactivation of parvulin-like peptidyl-prolyl cis/trans isomerases by juglone. Hennig, L., Christner, C., Kipping, M., Schelbert, B., Rücknagel, K.P., Grabley, S., Küllertz, G., Fischer, G. Biochemistry (1998) [Pubmed]
  3. Epidermal ornithine decarboxylase induction and mouse skin tumor promotion by quinones. Monks, T.J., Walker, S.E., Flynn, L.M., Conti, C.J., DiGiovanni, J. Carcinogenesis (1990) [Pubmed]
  4. Idebenone acts against growth of Helicobacter pylori by inhibiting its respiration. Inatsu, S., Ohsaki, A., Nagata, K. Antimicrob. Agents Chemother. (2006) [Pubmed]
  5. Peroxiredoxin-linked detoxification of hydroperoxides in Toxoplasma gondii. Akerman, S.E., Müller, S. J. Biol. Chem. (2005) [Pubmed]
  6. Functional replacement of the essential ESS1 in yeast by the plant parvulin DlPar13. Metzner, M., Stoller, G., Rücknagel, K.P., Lu, K.P., Fischer, G., Luckner, M., Küllertz, G. J. Biol. Chem. (2001) [Pubmed]
  7. Functional conservation of phosphorylation-specific prolyl isomerases in plants. Yao, J.L., Kops, O., Lu, P.J., Lu, K.P. J. Biol. Chem. (2001) [Pubmed]
  8. Regulation of Arabidopsis SHY2/IAA3 protein turnover. Tian, Q., Nagpal, P., Reed, J.W. Plant J. (2003) [Pubmed]
  9. Functional analysis of the glutathione S-transferase 3 from Onchocerca volvulus (Ov-GST-3): a parasite GST confers increased resistance to oxidative stress in Caenorhabditis elegans. Kampkötter, A., Volkmann, T.E., de Castro, S.H., Leiers, B., Klotz, L.O., Johnson, T.E., Link, C.D., Henkle-Dührsen, K. J. Mol. Biol. (2003) [Pubmed]
  10. Mechanisms of toxicity of 2- and 5-hydroxy-1,4-naphthoquinone; absence of a role for redox cycling in the toxicity of 2-hydroxy-1,4-naphthoquinone to isolated hepatocytes. d'Arcy Doherty, M., Rodgers, A., Cohen, G.M. Journal of applied toxicology : JAT. (1987) [Pubmed]
  11. Interaction of benzoquinones with mitochondria interferes with oxidative phosphorylation characteristics. Makawiti, D.W., Konji, V.N., Olowookere, J.O. FEBS Lett. (1990) [Pubmed]
  12. The effect of juglone on the membrane potential and whole-cell K+ currents of human lymphocytes. Varga, Z., Bene, L., Pieri, C., Damjanovich, S., Gáspár, R. Biochem. Biophys. Res. Commun. (1996) [Pubmed]
  13. The natural toxin juglone causes degradation of p53 and induces rapid H2AX phosphorylation and cell death in human fibroblasts. Paulsen, M.T., Ljungman, M. Toxicol. Appl. Pharmacol. (2005) [Pubmed]
  14. Juglone disrupts root plasma membrane H+-ATPase activity and impairs water uptake, root respiration, and growth in soybean (Glycine max) and corn (Zea mays). Hejl, A.M., Koster, K.L. J. Chem. Ecol. (2004) [Pubmed]
  15. A photochemical study of cells loaded with 2',7'-dichlorofluorescin: implications for the detection of reactive oxygen species generated during UVA irradiation. Chignell, C.F., Sik, R.H. Free Radic. Biol. Med. (2003) [Pubmed]
  16. Nonphotochemical quenching of excitation energy in photosystem II. A picosecond time-resolved study of the low yield of chlorophyll a fluorescence induced by single-turnover flash in isolated spinach thylakoids. Vasil'ev, S., Bruce, D. Biochemistry (1998) [Pubmed]
  17. Effects of various environmental conditions on the transformation of chlorinated solvents by Methanosarcina thermophila cell exudates. Baeseman, J.L., Novak, P.J. Biotechnol. Bioeng. (2001) [Pubmed]
  18. 2- and 3-substituted 1,4-naphthoquinone derivatives as subversive substrates of trypanothione reductase and lipoamide dehydrogenase from Trypanosoma cruzi: synthesis and correlation between redox cycling activities and in vitro cytotoxicity. Salmon-Chemin, L., Buisine, E., Yardley, V., Kohler, S., Debreu, M.A., Landry, V., Sergheraert, C., Croft, S.L., Krauth-Siegel, R.L., Davioud-Charvet, E. J. Med. Chem. (2001) [Pubmed]
  19. Cytotoxic action of juglone and plumbagin: a mechanistic study using HaCaT keratinocytes. Inbaraj, J.J., Chignell, C.F. Chem. Res. Toxicol. (2004) [Pubmed]
  20. Effects of nitroxide stable radicals on juglone cytotoxicity. Zhang, R., Hirsch, O., Mohsen, M., Samuni, A. Arch. Biochem. Biophys. (1994) [Pubmed]
  21. Novel quinone antiproliferative inhibitors of phosphatidylinositol-3-kinase. Frew, T., Powis, G., Berggren, M., Gallegos, A., Abraham, R.T., Ashendel, C.L., Zalkow, L.H., Hudson, C., Gruszecka-Kowalik, E., Burgess, E.M. Anticancer Drug Des. (1995) [Pubmed]
  22. Degradation of juglone by Pleurotus sajor-caju. Curreli, N., Rescigno, A., Rinaldi, A., Pisu, B., Sollai, F., Sanjust, E. Mycol. Res. (2004) [Pubmed]
  23. Walnut extract inhibits the fibrillization of amyloid beta-protein, and also defibrillizes its preformed fibrils. Chauhan, N., Wang, K.C., Wegiel, J., Malik, M.N. Current Alzheimer research. (2004) [Pubmed]
  24. Interaction of camel lens zeta-crystallin with quinones: portrait of a substrate by fluorescence spectroscopy. Bazzi, M.D. Arch. Biochem. Biophys. (2001) [Pubmed]
  25. Induction of quinone reductase and glutathione transferase in rat tissues by juglone and plumbagin. Munday, R., Munday, C.M. Planta Med. (2000) [Pubmed]
  26. Ascorbate-independent electron transfer between cytochrome b561 and a 27 kDa ascorbate peroxidase of bean hypocotyls. Preger, V., Pesaresi, A., Pupillo, P., Trost, P. Protoplasma (2001) [Pubmed]
  27. Induced juglone toxicosis in ponies and horses. True, R.G., Lowe, J.E. Am. J. Vet. Res. (1980) [Pubmed]
  28. Metabolism and disposition of juglone in male F344 rats. Chen, L.J., Lebetkin, E.H., Burka, L.T. Xenobiotica (2005) [Pubmed]
  29. The induction of equine laminitis with an aqueous extract of the heartwood of black walnut (Juglans nigra). Minnick, P.D., Brown, C.M., Braselton, W.E., Meerdink, G.L., Slanker, M.R. Veterinary and human toxicology. (1987) [Pubmed]
  30. Using of liquid chromatography coupled with diode array detector for determination of naphthoquinones in plants and for investigation of influence of pH of cultivation medium on content of plumbagin in Dionaea muscipula. Babula, P., Mikelova, R., Adam, V., Kizek, R., Havel, L., Sladky, Z. J. Chromatogr. B Analyt. Technol. Biomed. Life Sci. (2006) [Pubmed]
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