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Chemical Compound Review

Plumbaein     5-hydroxy-2-methyl- naphthalene-1,4-dione

Synonyms: Plumbagin, Plumbagine, Plumbagone, SureCN34186, CHEMBL295316, ...
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Disease relevance of Plumbagin

  • Mu dX phage was used to isolate three gene fusions to the lacZ gene (soi::lacZ; soi for superoxide radical inducible) that were induced by treatment with superoxide radical anion generators such as paraquat and plumbagin [1].
  • Increasing the intracellular flux of O-2 by incubating aerobic Escherichia coli with paraquat or plumbagin markedly lowered the alpha, beta-dihydroxyisovalerate dehydratase activity detectable in extracts from these cells [2].
  • Plumbagin increased oxygen consumption by S. sanguis and imposed an oxygen-dependent toxicity [3].
  • When Mycobacterium smegmatis carrying the M. bovis katG gene was treated with nontoxic levels of plumbagin, a generator of superoxide, the bacteriostatic activity of INH increased unless a plasmid-borne superoxide dismutase gene was also present [4].
  • Cells pretreated with plumbagin could partially reactivate lambda phage damaged by exposure to riboflavin plus light, a treatment that produces active oxygen species [5].

High impact information on Plumbagin


Chemical compound and disease context of Plumbagin


Biological context of Plumbagin


Anatomical context of Plumbagin

  • In the present investigation, we treated isogenic mouse embryonic fibroblast (MEF) cell lines containing wild-type (MEF-polbeta) or DNA polymerase beta (polbeta) gene-knockout (MEFpolbetaKO) with oxidative DNA-damaging agent, plumbagin, and examined its effect on p21 levels and BER activity [7].
  • Of the enzymes and transport systems involved in the control of the cardiac contractility, the sarcoplasmic reticulum Ca2+ pump seemed to be a specific target for plumbagin [13].
  • Cytotoxic action of juglone and plumbagin: a mechanistic study using HaCaT keratinocytes [14].
  • Plumbagin decreased the binding between thrombin-stimulated platelets and neutrophils with an IC 50 of 62.9 microM [15].
  • Plumbagin was also seen to exert a similar response on oxygen radical release by macrophages in vivo showing a clear correlation between oxygen radical release and the bactericidal activity [16].

Associations of Plumbagin with other chemical compounds

  • Plumbagin also suppressed the direct binding of nuclear p65 and recombinant p65 to the DNA, and this binding was reversed by dithiothreitol both in vitro and in vivo [6].
  • Similarly, plasmid DNA, within the endonuclease-deficient cells, exhibited more strand scissions and endonuclease III-sensitive sites upon aerobic exposure to plumbagin than did endonuclease-sufficient cells, and a low molecular weight scavenger of O2- was protective [17].
  • The role of SOD for coping with the damaging effects of superoxide became evident after the increase in intracellular O2-. flux by growing cells under hyperoxygenation, but particularly by using redox cycling compounds such as plumbagin, paraquat and menadione [18].
  • However, apoptosis induction was greater in BRCA1-blocked cells, the efficacy being in the order of plumbagin > tamoxifen > emodin [19].
  • However, plumbagin stoichiometrically converted GSH to GSSG, indicating that redox cycling is its main metabolic pathway [14].

Gene context of Plumbagin

  • Taken together, these results suggest a critical role for JNK and p53 in plumbagin-induced G2/M arrest and apoptosis of human nonsmall cell lung cancer cells [11].
  • This throws light on the fact that plumbagin may have chemotherapeutic potential as an anticancer agent in BRCA1-mutated ovarian cancer patients [19].
  • Furthermore, suppression of AKT by plumbagin enhanced the activation of Chk2, resulting in increased inactive phosphorylation of Cdc25C and Cdc2 [20].
  • This hypersensitive phenotype was specific to the lactoperoxidase system, since neither the sensitivity to hydrogen peroxide nor to the superoxide generator plumbagin was affected in the corA mutant [21].
  • Cells pretreated with nonlethal doses of plumbagin showed enhanced survival upon exposure to high concentrations of plumbagin, but were unchanged in their susceptibility to far-UV irradiation. polA and recA mutants were not significantly more sensitive than wild type to killing by plumbagin [5].

Analytical, diagnostic and therapeutic context of Plumbagin


  1. Isolation of gene fusions (soi::lacZ) inducible by oxidative stress in Escherichia coli. Kogoma, T., Farr, S.B., Joyce, K.M., Natvig, D.O. Proc. Natl. Acad. Sci. U.S.A. (1988) [Pubmed]
  2. alpha, beta-Dihydroxyisovalerate dehydratase. A superoxide-sensitive enzyme. Kuo, C.F., Mashino, T., Fridovich, I. J. Biol. Chem. (1987) [Pubmed]
  3. Oxygen toxicity in Streptococcus sanguis. The relative importance of superoxide and hydroxyl radicals. DiGuiseppi, J., Fridovich, I. J. Biol. Chem. (1982) [Pubmed]
  4. Role of superoxide in catalase-peroxidase-mediated isoniazid action against mycobacteria. Wang, J.Y., Burger, R.M., Drlica, K. Antimicrob. Agents Chemother. (1998) [Pubmed]
  5. Toxicity and mutagenicity of plumbagin and the induction of a possible new DNA repair pathway in Escherichia coli. Farr, S.B., Natvig, D.O., Kogoma, T. J. Bacteriol. (1985) [Pubmed]
  6. Plumbagin (5-hydroxy-2-methyl-1,4-naphthoquinone) suppresses NF-kappaB activation and NF-kappaB-regulated gene products through modulation of p65 and IkappaBalpha kinase activation, leading to potentiation of apoptosis induced by cytokine and chemotherapeutic agents. Sandur, S.K., Ichikawa, H., Sethi, G., Ahn, K.S., Aggarwal, B.B. J. Biol. Chem. (2006) [Pubmed]
  7. Long-patch base excision repair of apurinic/apyrimidinic site DNA is decreased in mouse embryonic fibroblast cell lines treated with plumbagin: involvement of cyclin-dependent kinase inhibitor p21Waf-1/Cip-1. Jaiswal, A.S., Bloom, L.B., Narayan, S. Oncogene (2002) [Pubmed]
  8. Induction of oxidative stress by high hydrostatic pressure in Escherichia coli. Aertsen, A., De Spiegeleer, P., Vanoirbeek, K., Lavilla, M., Michiels, C.W. Appl. Environ. Microbiol. (2005) [Pubmed]
  9. The whcE gene of Corynebacterium glutamicum is important for survival following heat and oxidative stress. Kim, T.H., Park, J.S., Kim, H.J., Kim, Y., Kim, P., Lee, H.S. Biochem. Biophys. Res. Commun. (2005) [Pubmed]
  10. Chemical modification of the lactose carrier of Escherichia coli by plumbagin, phenylarsinoxide or diethylpyrocarbonate affects the binding of galactoside. Neuhaus, J.M., Wright, J.K. Eur. J. Biochem. (1983) [Pubmed]
  11. Plumbagin (5-hydroxy-2-methyl-1,4-naphthoquinone) induces apoptosis and cell cycle arrest in A549 cells through p53 accumulation via c-Jun NH2-terminal kinase-mediated phosphorylation at serine 15 in vitro and in vivo. Hsu, Y.L., Cho, C.Y., Kuo, P.L., Huang, Y.T., Lin, C.C. J. Pharmacol. Exp. Ther. (2006) [Pubmed]
  12. Plumbagin induces reactive oxygen species, which mediate apoptosis in human cervical cancer cells. Srinivas, P., Gopinath, G., Banerji, A., Dinakar, A., Srinivas, G. Mol. Carcinog. (2004) [Pubmed]
  13. Mechanisms of plumbagin action on guinea pig isolated atria. Floreani, M., Forlin, A., Pandolfo, L., Petrone, M., Bellin, S. J. Pharmacol. Exp. Ther. (1996) [Pubmed]
  14. Cytotoxic action of juglone and plumbagin: a mechanistic study using HaCaT keratinocytes. Inbaraj, J.J., Chignell, C.F. Chem. Res. Toxicol. (2004) [Pubmed]
  15. Effects of plumbagin on platelet aggregation and platelet-neutrophil interactions. Shen, Z., Dong, Z., Cheng, P., Li, L., Chen, Z., Liu, J. Planta Med. (2003) [Pubmed]
  16. Modulatory effect of plumbagin (5-hydroxy-2-methyl-1,4-naphthoquinone) on macrophage functions in BALB/c mice. I. Potentiation of macrophage bactericidal activity. Abdul, K.M., Ramchender, R.P. Immunopharmacology (1995) [Pubmed]
  17. Formation of endonuclease III-sensitive sites as a consequence of oxygen radical attack on DNA. Denq, R.Y., Fridovich, I. Free Radic. Biol. Med. (1989) [Pubmed]
  18. Mutagenesis in Escherichia coli K-12 mutants defective in superoxide dismutase or catalase. Prieto-Alamo, M.J., Abril, N., Pueyo, C. Carcinogenesis (1993) [Pubmed]
  19. Antisense blocking of BRCA1 enhances sensitivity to plumbagin but not tamoxifen in BG-1 ovarian cancer cells. Srinivas, G., Annab, L.A., Gopinath, G., Banerji, A., Srinivas, P. Mol. Carcinog. (2004) [Pubmed]
  20. Plumbagin induces G2-M arrest and autophagy by inhibiting the AKT/mammalian target of rapamycin pathway in breast cancer cells. Kuo, P.L., Hsu, Y.L., Cho, C.Y. Mol. Cancer Ther. (2006) [Pubmed]
  21. CorA affects tolerance of Escherichia coli and Salmonella enterica serovar Typhimurium to the lactoperoxidase enzyme system but not to other forms of oxidative stress. Sermon, J., Wevers, E.M., Jansen, L., De Spiegeleer, P., Vanoirbeek, K., Aertsen, A., Michiels, C.W. Appl. Environ. Microbiol. (2005) [Pubmed]
  22. Determination and identification of plumbagin from the roots of Plumbago zeylanica L. by liquid chromatography with tandem mass spectrometry. Hsieh, Y.J., Lin, L.C., Tsai, T.H. Journal of chromatography. A. (2005) [Pubmed]
  23. High-performance liquid chromatography for quantification of plumbagin, an anti-Helicobacter pylori compound of Plumbago zeylanica L. Wang, Y.C., Huang, T.L. Journal of chromatography. A. (2005) [Pubmed]
  24. Enhanced production of plumbagin in immobilized cells of Plumbago rosea by elicitation and in situ adsorption. Komaraiah, P., Ramakrishna, S.V., Reddanna, P., Kavi Kishor, P.B. J. Biotechnol. (2003) [Pubmed]
  25. Antioxidant properties of Plumbago zeylanica, an Indian medicinal plant and its active ingredient, plumbagin. Tilak, J.C., Adhikari, S., Devasagayam, T.P. Redox Rep. (2004) [Pubmed]
  26. UV/Vis spectra and solubility of some naphthoquinones, and the extraction behavior of plumbagin from Plumbago scandens roots in supercritical CO2. Rodrigues, S.V., Viana, L.M., Baumann, W. Analytical and bioanalytical chemistry. (2006) [Pubmed]
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