Plumbagin

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Plumbagin
IUPAC name

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

Identifiers
CAS number 481-42-5 N
PubChem 10205
ChemSpider 9790 YesY
KEGG C10387 YesY
ChEBI CHEBI:8273 YesY
ChEMBL CHEMBL295316 YesY
Jmol-3D images Image 1
Properties
Molecular formula C11H8O3
Molar mass 188.17942 g/mol
 N (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Plumbagin or 5-hydroxy-2-methyl-1,4-naphthoquinone is an organic compound with the chemical formula C
11H
8O
3. It is regarded as a toxin[1] and it is genotoxic[2] and mutagenic.[3]

Plumbagin is a yellow dye,[1] formally derived from naphthoquinone.

It is named after the plant genus Plumbago, from which it was originally isolated.[4] It is also commonly found in the carnivorous plant genera Drosera and Nepenthes.[5][6] It is also a component of the black walnut drupe (Juglans nigra).

Pharmacologic properties

The following properties were described in various cellular and animal models:

  • antimicrobial,[7][8]
  • antimalarial,[9]
  • anti-inflammatory,[10]
  • anticarcinogenic,[11][12][13]
  • cardiotonic,[14]
  • immunosuppressive,[15]
  • antifertility action,[16]
  • neuroprotective,[17]
  • anti-atherosclerosis effects.[18]
  • Plumbagin has been shown to induce cell cycle arrest and apoptosis in numerous cancer cell lines including melanoma, lung, breast and others.[citation needed] It triggers autophagy via inhibition of the Akt/mTOR pathway and induces G2/M cell cycle arrest and apoptosis in A549 cells through JNK-dependent p53 Ser15 phosphorylation. Promotes autophagic cell death in MDA-MB-231 and MCF-7 cells and inhibits Akt/mTOR signaling. Induces intracellular ROS generation in a PI 5-kinase-dependent manner.
  • Plumbagin shows antimicrobial activity[19]
  • Positive inotropic activity[20]
  • Enzymatic spectrum of herbal plants Plumbago Linn.[21]
  • Bioactive spectra of plumbagin.[22]
  • Effect on root- knot nematode Meloidogyne spp.[23]

References

  1. ↑ 1.0 1.1 Black Walnut. Drugs.com.
  2. ↑ "Genotoxicity of plumbagin and its effects on catechol and NQNO-induced DNA damage in mouse lymphoma cells". Jemal Demma, Karl Hallberg, Björn Hellman 23 (2): 266–271. 2009. doi:10.1016/j.tiv.2008.12.007. 
  3. ↑ S B Farr, D O Natvig, and T Kogoma (1985). "Toxicity and mutagenicity of plumbagin and the induction of a possible new DNA repair pathway in Escherichia coli". J Bacteriol 164 (3): 1309–1316. PMC 219331. 
  4. ↑ van der Vijver, L. M. (1972). "Distribution of Plumbagin in the Plumbaginaceae". Phytochemistry 11 (11): 3247–3248. doi:10.1016/S0031-9422(00)86380-3. 
  5. ↑ Wang, W.; Luo, X.; Li, H. (2010). "Terahertz and Infrared Spectra of Plumbagin, Juglone, and Menadione". Carnivorous Plant Newsletter 39 (3): 82–88. 
  6. ↑ Rischer, H.; Hamm, A.; Bringmann, G. (2002). "Nepenthes insignis Uses a C2-Portion of the Carbon Skeleton of L-Alanine Acquired via its Carnivorous Organs, to Build up the Allelochemical Plumbagin". Phytochemistry 59 (6): 603–609. doi:10.1016/S0031-9422(02)00003-1. 
  7. ↑ Didry, N.; Dubrevil, L.; Pinkas, M. (1994). "Activity of anthraquinonic and naphthoquinonic compounds on oral bacteria". Die Pharmazie 49 (9): 681–683. PMID 7972313. 
  8. ↑ de Paiva, S. R.; Figueiredo, M. R.; Aragão, T. V.; Kaplan, M. A. C. (2003). "Antimicrobial Activity in Vitro of Plumbagin Isolated from Plumbago Species" (pdf). Memórios do Instituto Oswaldo Cruz 98 (7): 959–961. doi:10.1590/S0074-02762003000700017. PMID 14762525. 
  9. ↑ Likhitwitayawuid, K.; Kaewamatawong, R.; Ruangrungsi, N.; Krungkrai, J. (1998). "Antimalarial Naphthoquinones from Nepenthes thorelii". Planta Medica 64 (3): 237–241. doi:10.1055/s-2006-957417. PMID 9581522. 
  10. ↑ Checker R.; Sharma D.; Sandur, S. K.; Subrahmanyam, G.; Krishnan, S.; Poduval, T. B.; Sainis, K. B. (2010). "Plumbagin inhibits proliferative and inflammatory responses of T cells independent of ROS generation but by modulating intracellular thiols" (pdf). Journal of Cellular Biochemistry 110 (5): 1082–1093. doi:10.1002/jcb.22620. PMC 3065107. PMID 20564204. 
  11. ↑ Parimala, R.; Sachdanandam, P. (1993). "Effect of plumbagin on some glucose metabolizing enzymes studied in rats in experimental hepatoma". Molecular and Cellular Biochemistry 125 (1): 59–63. doi:10.1007/BF00926835. PMID 8264573. 
  12. ↑ Hsu, Y.-L.; Cho,, C.-Y.; Kuo, P.-L.; Huang, Y.-T.; Lin, C.-C. (2006). "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" (pdf). Journal of Pharmacology and Experimental Therapeutics 318 (2): 484–494. doi:10.1124/jpet.105.098863. PMID 16632641. 
  13. ↑ Subramaniya, B. R.; Srinivasan, G.; Sadullah, S. S.; Davis, N.; Subhadara, L. B.; Halagowder, D.; Sivasitambaram, N. D. (2011). "Apoptosis Inducing Effect of Plumbagin on Colonic Cancer Cells Depends on Expression of COX-2". In Navarro, Alfons. PLoS ONE 6 (4): e18695. doi:10.1371/journal.pone.0018695. PMC 3084694. PMID 21559086. 
  14. ↑ Itoigawa, M.; Takeya, K.; Furukawa, H. (1991). "Cardiotonic action of plumbagin on guinea-pig papillary muscle". Planta Medica 57 (4): 317–319. doi:10.1055/s-2006-960106. PMID 1775570. 
  15. ↑ McKallip, R. J.; Lombard, C.; Sun, J.; Ramakrishnan, R. (2010). "Plumbagin-induced apoptosis in lymphocytes is mediated through increased reactive oxygen species production, upregulation of Fas, and activation of the caspase cascade". Toxicology and Applied Pharmacology 247 (1): 41–52. doi:10.1016/j.taap.2010.05.013. PMID 20576514. 
  16. ↑ Bhargava, S. K. (1984). "Effects of plumbagin on reproductive function of male dog". Indian Journal of Experimental Biology 22 (3): 153–156. PMID 6083981. 
  17. ↑ Son, T. G.; Camandola, S.; Arumugam, T. V.; Cutler, R. G.; Telljohann, R. S.; Mughal, M. R.; Moore, T. A.; Luo, W.; Yu, Q. S.; Johnson, D. A.; Johnson, J. A.; Greig, N. H.; Mattson, M. P. (2010). "Plumbagin, a novel Nrf2/ARE Activator, Protects against Cerebral Ischemia" (pdf). Journal of Neurochemistry 112 (5): 1316–1326. doi:10.1111/j.1471-4159.2009.06552.x. PMC 2819586. PMID 20028456. 
  18. ↑ Ding, Y.; Chen, Z.-J.; Liu, S.; Che, D.; Vetter, M.; Chang, C.-H. (2005). "Inhibition of Nox-4 activity by plumbagin, a plant-derived bioactive naphthoquinone". Journal of Pharmacy and Pharmacology 57 (1): 111–116. doi:10.1211/0022357055119. PMID 15638999. 
  19. ↑ Dama L.B., Poul B.N.and Jadhav B.V. (1998). Antimicrobial activity of Napthoquinonic compounds. J. Ecotoxicol. Environ. Monit. 8:213-215
  20. ↑ Poul B.N, Dama L.B.,and Jadhav B.V. (1999). Positive inotropic activity of Plumbagin. D. E. I. J. Sci. Engineering Res. 11: 26-29
  21. ↑ Poul B. N., Dama L.B. and Jadhav B. V. (1999). Enzymatic spectrum of herbal Plants Plumbago Linn. Asian J. Chem. 11(1):273-275
  22. ↑ Poul B. N., DamaL.B. and Jadhav B. V. (1999).Bioactive spectra of Plumbagin. Asian J. Chem. 11 (1):144-148
  23. ↑ Dama L.B. (2002).  Effect of naturally occurring napthoquinones on root- knot nematode Meloidogyne spp. Indian Phytopathology. 55 (1): 67-69
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