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词条 Plumbagin
释义

  1. Pharmacologic properties

  2. See also

  3. References

{{Chembox
| Verifiedfields = changed
| verifiedrevid = 461751697
| Name = Plumbagin
| ImageFile = Plumbagin.PNG
| ImageSize = 180
| ImageName = Skeletal formula of plumbagin
| ImageFile1 = Plumbagin-3D-balls.png
| ImageSize1 = 190
| ImageName1 = Ball-and-stick model of plumbagin
| IUPACName = 5-hydroxy-2-methyl-naphthalene-1,4-dione
| OtherNames =
|Section1={{Chembox Identifiers
| IUPHAR_ligand = 7003
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 9790
| PubChem = 10205
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = C10387
| InChI = 1/C11H8O3/c1-6-5-9(13)10-7(11(6)14)3-2-4-8(10)12/h2-5,12H,1H3
| InChIKey = VCMMXZQDRFWYSE-UHFFFAOYAB
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 295316
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C11H8O3/c1-6-5-9(13)10-7(11(6)14)3-2-4-8(10)12/h2-5,12H,1H3
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = VCMMXZQDRFWYSE-UHFFFAOYSA-N
| CASNo_Ref = {{cascite|changed|??}}
| CASNo = 481-42-5
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 8273
| SMILES = O=C\\2c1c(O)cccc1C(=O)/C(=C/2)C
|Section2={{Chembox Properties
| Formula = C11H8O3
| MolarMass = 188.17942 g/mol
| Density =
| MeltingPt =
| BoilingPt =
| Solubility =
}}Plumbagin or 5-hydroxy-2-methyl-1,4-naphthoquinone is an organic compound with the chemical formula {{chem|C|11|H|8|O|3}}. It is regarded as a toxin[1] and it is genotoxic[1] and mutagenic.[2]

Plumbagin is a yellow dye,[3] 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.

Pharmacologic properties

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

  • antimicrobial,[7][8][9]
  • antimalarial,[10]
  • anti-inflammatory,[11]
  • anticarcinogenic,[12][13][14]
  • cardiotonic,[15]
  • immunosuppressive,[16]
  • antifertility action,[17]
  • neuroprotective,[18]
  • anti-atherosclerosis effects.[19]
  • Plumbagin has been shown to induce cell cycle arrest and apoptosis in numerous cancer cell lines including melanoma, lung, breast and others.{{citation needed|date=May 2013}} 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.
  • 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]

See also

  • Juglone

References

1. ^{{Cite journal | journal = Toxicology in Vitro | volume = 23 | issue = 2 | year = 2009 | pages = 266–271 | title = Genotoxicity of plumbagin and its effects on catechol and NQNO-induced DNA damage in mouse lymphoma cells |author1=Jemal Demma |author2=Karl Hallberg |author3=Björn Hellman | doi = 10.1016/j.tiv.2008.12.007}}
2. ^{{Cite journal | journal = J Bacteriol | year = 1985 | volume = 164 | issue = 3 | pages = 1309–1316 | pmc = 219331 | title = Toxicity and mutagenicity of plumbagin and the induction of a possible new DNA repair pathway in Escherichia coli |author1=S B Farr |author2=D O Natvig |author3=T Kogoma |last-author-amp=yes | pmid=2933393}}
3. ^1 [https://www.drugs.com/npp/black-walnut.html Black Walnut]. Drugs.com.
4. ^{{ cite journal |author1=van der Vijver |author2=L. M. | title = Distribution of Plumbagin in the Plumbaginaceae | journal = Phytochemistry | year = 1972 | volume = 11 | issue = 11 | pages = 3247–3248 | doi = 10.1016/S0031-9422(00)86380-3 }}
5. ^{{ cite journal |author1=Wang, W. |author2=Luo, X. |author3=Li, H. | title = Terahertz and Infrared Spectra of Plumbagin, Juglone, and Menadione | journal = Carnivorous Plant Newsletter | year = 2010 | volume = 39 | issue = 3 | pages = 82–88 }}
6. ^{{ cite journal |author1=Rischer, H. |author2=Hamm, A. |author3=Bringmann, G. | title = Nepenthes insignis Uses a C2-Portion of the Carbon Skeleton of L-Alanine Acquired via its Carnivorous Organs, to Build up the Allelochemical Plumbagin | journal = Phytochemistry | year = 2002 | volume = 59 | issue = 6 | pages = 603–609 | doi = 10.1016/S0031-9422(02)00003-1 }}
7. ^{{ cite journal |author1=Didry, N. |author2=Dubrevil, L. |author3=Pinkas, M. | title = Activity of anthraquinonic and naphthoquinonic compounds on oral bacteria | journal = Die Pharmazie | year = 1994 | volume = 49 | issue = 9 | pages = 681–683 | pmid = 7972313 }}
8. ^{{ cite journal |author1=de Paiva, S. R. |author2=Figueiredo, M. R. |author3=Aragão, T. V. |author4=Kaplan, M. A. C. | title = Antimicrobial Activity in Vitro of Plumbagin Isolated from Plumbago Species | journal = Memórias do Instituto Oswaldo Cruz | year = 2003 | volume = 98 | issue = 7 | pages = 959–961 | pmid = 14762525 | doi = 10.1590/S0074-02762003000700017 | url = http://www.scielo.br/pdf/mioc/v98n7/v98n7a17.pdf | format = pdf }}
9. ^Dama L.B., Poul B.N.and Jadhav B.V. (1998). Antimicrobial activity of Napthoquinonic compounds. J. Ecotoxicol. Environ. Monit. 8:213-215
10. ^{{ cite journal |author1=Likhitwitayawuid, K. |author2=Kaewamatawong, R. |author3=Ruangrungsi, N. |author4=Krungkrai, J. | title = Antimalarial Naphthoquinones from Nepenthes thorelii | journal = Planta Medica | year = 1998 | volume = 64 | issue = 3 | pages = 237–241 | pmid = 9581522 | doi=10.1055/s-2006-957417}}
11. ^{{ cite journal |author1=Checker R. |author2=Sharma D. |author3=Sandur, S. K. |author4=Subrahmanyam, G. |author5=Krishnan, S. |author6=Poduval, T. B. |author7=Sainis, K. B. | title = Plumbagin inhibits proliferative and inflammatory responses of T cells independent of ROS generation but by modulating intracellular thiols | journal = Journal of Cellular Biochemistry | year = 2010 | volume = 110 | issue = 5 | pages = 1082–1093 | pmid = 20564204 | pmc = 3065107 | url = https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3065107/pdf/nihms279632.pdf | format = pdf | doi=10.1002/jcb.22620}}
12. ^{{ cite journal |author1=Parimala, R. |author2=Sachdanandam, P. | title = Effect of plumbagin on some glucose metabolizing enzymes studied in rats in experimental hepatoma | journal = Molecular and Cellular Biochemistry | year = 1993 | volume = 125 | issue = 1 | pages = 59–63 | pmid = 8264573 | doi = 10.1007/BF00926835 }}
13. ^{{ cite journal |author1=Hsu, Y.-L. |author2=Cho,, C.-Y. |author3=Kuo, P.-L. |author4=Huang, Y.-T. |author5=Lin, C.-C. | title = 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 | journal = Journal of Pharmacology and Experimental Therapeutics | year = 2006 | volume = 318 | issue = 2 | pages = 484–494 | doi = 10.1124/jpet.105.098863 | pmid = 16632641 | url = http://jpet.aspetjournals.org/content/318/2/484.full.pdf | format = pdf }}
14. ^{{Cite journal | last1 = Subramaniya | first1 = B. R. | last2 = Srinivasan | first2 = G. | last3 = Sadullah | first3 = S. S. | last4 = Davis | first4 = N. | last5 = Subhadara | first5 = L. B. | last6 = Halagowder | first6 = D. | last7 = Sivasitambaram | first7 = N. D. | editor1-last = Navarro | editor1-first = Alfons | title = Apoptosis Inducing Effect of Plumbagin on Colonic Cancer Cells Depends on Expression of COX-2 | doi = 10.1371/journal.pone.0018695 | journal = PLoS ONE | volume = 6 | issue = 4 | pages = e18695 | year = 2011 | pmid = 21559086| pmc = 3084694 }}
15. ^{{ cite journal |author1=Itoigawa, M. |author2=Takeya, K. |author3=Furukawa, H. | title = Cardiotonic action of plumbagin on guinea-pig papillary muscle | journal = Planta Medica | year = 1991 | volume = 57 | issue = 4 | pages = 317–319 | pmid = 1775570 | doi = 10.1055/s-2006-960106 }}
16. ^{{ cite journal |author1=McKallip, R. J. |author2=Lombard, C. |author3=Sun, J. |author4=Ramakrishnan, R. | title = Plumbagin-induced apoptosis in lymphocytes is mediated through increased reactive oxygen species production, upregulation of Fas, and activation of the caspase cascade | journal = Toxicology and Applied Pharmacology | year = 2010 | volume = 247 | issue = 1 | pages = 41–52 | pmid = 20576514 | doi = 10.1016/j.taap.2010.05.013 }}
17. ^{{ cite journal | author = Bhargava, S. K. | title = Effects of plumbagin on reproductive function of male dog | journal = Indian Journal of Experimental Biology | year = 1984 | volume = 22 | issue = 3 | pages = 153–156 | pmid = 6083981 }}
18. ^{{ cite journal |author1=Son, T. G. |author2=Camandola, S. |author3=Arumugam, T. V. |author4=Cutler, R. G. |author5=Telljohann, R. S. |author6=Mughal, M. R. |author7=Moore, T. A. |author8=Luo, W. |author9=Yu, Q. S. |author10=Johnson, D. A. |author11=Johnson, J. A. |author12=Greig, N. H. |author13=Mattson, M. P. | title = Plumbagin, a novel Nrf2/ARE Activator, Protects against Cerebral Ischemia | journal = Journal of Neurochemistry | year = 2010 | volume = 112 | issue = 5 | pages = 1316–1326 | pmid = 20028456 | pmc = 2819586 | url = https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2819586/pdf/nihms166741.pdf | format = pdf | doi=10.1111/j.1471-4159.2009.06552.x}}
19. ^{{ cite journal |author1=Ding, Y. |author2=Chen, Z.-J. |author3=Liu, S. |author4=Che, D. |author5=Vetter, M. |author6=Chang, C.-H. | title = Inhibition of Nox-4 activity by plumbagin, a plant-derived bioactive naphthoquinone | journal = Journal of Pharmacy and Pharmacology | year = 2005 | volume = 57 | issue = 1 | pages = 111–116 | pmid = 15638999 | doi = 10.1211/0022357055119 }}
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

3 : 1,4-Naphthoquinones|1-Naphthols|Hydroxynaphthoquinones
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