Plumbagin: Difference between revisions

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{{for|the mineral known as plombagine|Plumbago (mineral)}}
{{Chembox new
{{Chembox
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| Name = Plumbagin
| Verifiedfields = changed
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| ImageFile =
| verifiedrevid = 461751697
| IUPACName = 5-hydroxy-2-methyl-naphthalene-1,4-dione
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| Name = Plumbagin
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| OtherNames =
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| ImageFile = Plumbagin.PNG
| ImageSize = 180
| ImageName = Skeletal formula of plumbagin
| ImageFile1 = Plumbagin-3D-balls.png
| ImageSize1 = 190
| ImageName1 = Ball-and-stick model of plumbagin
| PIN = 5-Hydroxy-2-methylnaphthalene-1,4-dione
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| OtherNames =
| SystematicName =
| Section1 = {{Chembox Identifiers
| Section1 = {{Chembox Identifiers
| IUPHAR_ligand = 7003
⚫
| CASNo = 481-42-5
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
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| SMILES = CC1=CC(=O)C2=C(C1=O)C=CC=C2O
| ChemSpiderID = 9790
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}}
| 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|correct|CAS}}
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| CASNo = 481-42-5
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = YAS4TBQ4OQ
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 8273
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| SMILES = Oc1c2C(=O)cc(C)C(=O)c2ccc1
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}}
| Section2 = {{Chembox Properties
| Section2 = {{Chembox Properties
| Formula = C<sub>11</sub>H<sub>8</sub>O<sub>3</sub>
| Formula = C<sub>11</sub>H<sub>8</sub>O<sub>3</sub>
| MolarMass = 188.17942 g/mol
| MolarMass = 188.17942 g/mol
| Density =
| Density =
| MeltingPt =
| MeltingPt =
| BoilingPt =
| BoilingPt =
| Solubility =
| Solubility =
}}
}}
| Section3 =
| Section4 =
| Section5 =
| Section6 =
}}
}}


'''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]]<ref name=walnut /> and it is [[Genotoxicity|genotoxic]]<ref>{{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| pmid = 19124069 }}</ref> and [[mutagenic]].<ref>{{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 | doi = 10.1128/JB.164.3.1309-1316.1985 |name-list-style=amp | pmid=2933393}}</ref>
'''Plumbagin''' is a [[plant]]-derived [[naphthoquinone]] possessing a number of pharmacological activities. It has been shown to have [[microorganism|antimicrobial]] activity.<ref>Didry, N., L. Dubrevil & M. Pinkas 1994. Activity of anthraquinonic and naphthoquinonic compounds on oral bacteria. ''Die Pharmazie'' '''49'''(9): 681–683.</ref><ref>Paiva, S.R.d., M.R. Figueiredo, T. V. Aragão, M.A.C. Kaplan 2003. {{PDFlink|[http://www.scielo.br/pdf/mioc/v98n7/v98n7a17.pdf Antimicrobial Activity in Vitro of Plumbagin Isolated from ''Plumbago'' Species.]}} ''Mem Inst Oswaldo Cruz'' '''98'''(7): 959–961.</ref> In animals, it has [[malaria|antimalarial]],<ref>Likhitwitayawuid, K., R. Kaewamatawong, N. Ruangrungsi & J. Krungkrai 1998. Antimalarial naphthoquinones from ''Nepenthes thorelii''. ''Planta Medica'' '''64'''(3): 237–241.</ref> [[carcinogen|anticarcinogenic]],<ref>Parimala, R. & P. Sachdanandam 1993. Effect of plumbagin on some glucose metabolizing enzymes studied in rats in experimental hepatoma. ''Molecular and Cellular Biochemistry'' '''12'''(1): 59–63.</ref><ref>Hsu, Y.-L., C.-Y. Cho, P.-L. Kuo, Y.-T. Huang & C.-C. Lin 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. ''Journal of Pharmacology and Experimental Therapeutics'' '''318'''(2): 484–494. {{DOI|10.1124/jpet.105.098863}}</ref> [[heart|cardiotonic]],<ref>Itoigawa, M., K. Takeya & H. Furukawa 1991. Cardiotonic action of plumbagin on guinea-pig papillary muscle. ''Planta Medica'' '''57'''(4): 317–319.</ref> [[fertility|antifertilityaction]],<ref>Bhargava, S.K. 1984. Effects of plumbagin on reproductive function of male dog. ''Indian Journal of Experimental Biology'' '''22'''(3): 153–156.</ref> and [[atherosclerosis|anti-atherosclerosis]] effects.<ref>Ding, Y., Z.-J. Chen, S. Liu, D. Che, M. Vetter, C.-H. Chang 2005. Inhibition of Nox-4 activity by plumbagin, a plant-derived bioactive naphthoquinone. ''Journal of Pharmacy and Pharmacology'' '''57'''(1): 111.</ref>


Plumbagin is a yellow [[dye]],<ref name=walnut>[https://www.drugs.com/npp/black-walnut.html Black Walnut]. Drugs.com.</ref> formally derived from [[naphthoquinone]].
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Plumbagin is named after the plant genus ''[[Plumbago]]'', from which it was originally isolated.<ref>Van der Vijver, L.M. 1972. Distribution of plumbagin in the Plumbaginaceae. ''Phytochemistry'' '''11''': 3247–3248.</ref>


⚫
It is named after the plant genus ''[[Plumbago]]'', from which it was originally isolated.<ref>{{ 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 }}</ref>
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==References==
It is also commonly found in the [[carnivorous plant]] genera ''[[Drosera]]'' and ''[[Nepenthes]]''.<ref>{{ 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 }}</ref><ref name=Rischer>{{ cite journal |author1=Rischer, H. |author2=Hamm, A. |author3=Bringmann, G. | title = ''Nepenthes insignis'' Uses a C<sub>2</sub>-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 |pmid=11867092 }}</ref> It is also a component of the [[Juglans nigra|black walnut]] drupe.
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{{reflist}}


== See also ==
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[[Category:Aromatic compounds]]
* [[Juglone]]
[[Category:Ketones]]

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== References ==
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{{reflist}}


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[[Category:1,4-Naphthoquinones]]
{{aromatic-stub}}
[[Category:Hydroxynaphthoquinones]]

Latest revision as of 00:55, 1 July 2022

For the mineral known as plombagine, see Plumbago (mineral).
Plumbagin
Skeletal formula of plumbagin
Ball-and-stick model of plumbagin
Names
Preferred IUPAC name
5-Hydroxy-2-methylnaphthalene-1,4-dione
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.006.882 Edit this at Wikidata
KEGG
UNII
  • InChI=1S/C11H8O3/c1-6-5-9(13)10-7(11(6)14)3-2-4-8(10)12/h2-5,12H,1H3 checkY
    Key: VCMMXZQDRFWYSE-UHFFFAOYSA-N checkY
  • InChI=1/C11H8O3/c1-6-5-9(13)10-7(11(6)14)3-2-4-8(10)12/h2-5,12H,1H3
    Key: VCMMXZQDRFWYSE-UHFFFAOYAB
  • Oc1c2C(=O)cc(C)C(=O)c2ccc1
Properties
C11H8O3
Molar mass 188.17942 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

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.

See also[edit]

References[edit]

  1. ^ a b Black Walnut. Drugs.com.
  2. ^ Jemal Demma; Karl Hallberg; Björn Hellman (2009). "Genotoxicity of plumbagin and its effects on catechol and NQNO-induced DNA damage in mouse lymphoma cells". Toxicology in Vitro. 23 (2): 266–271. doi:10.1016/j.tiv.2008.12.007. PMID 19124069.
  3. ^ S B Farr; D O Natvig & 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. doi:10.1128/JB.164.3.1309-1316.1985. PMC 219331. PMID 2933393.
  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. PMID 11867092.
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