{{for|the mineral known as plombagine|Plumbago (mineral)}} {{Chembox | Verifiedfields = changed | verifiedrevid = 461751697 | Name = Plumbagin | ImageFile = Plumbagin.PNG | ImageClass = skin-invert-image | 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 | OtherNames = | SystematicName = | 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|correct|CAS}} | CASNo = 481-42-5 | UNII_Ref = {{fdacite|correct|FDA}} | UNII = YAS4TBQ4OQ | ChEBI_Ref = {{ebicite|correct|EBI}} | ChEBI = 8273 | SMILES = Oc1c2C(=O)cc(C)C(=O)c2ccc1 }} | Section2 = {{Chembox Properties | Formula = C<sub>11</sub>H<sub>8</sub>O<sub>3</sub> | MolarMass = 188.17942 g/mol | Density = | MeltingPt = | BoilingPt = | 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 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 | bibcode = 2009ToxVi..23..266D }}</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 yellow dye,<ref name=walnut>[https://www.drugs.com/npp/black-walnut.html Black Walnut]. Drugs.com.</ref> formally derived from naphthoquinone.
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 |bibcode=1972PChem..11.3247V }}</ref> 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 |doi=10.55360/cpn393.ww544 |url=https://www.biodiversitylibrary.org/part/265979 }}</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 |bibcode=2002PChem..59..603R }}</ref> It is also a component of the black walnut drupe.
Plumbagin inhibits CYP2J2.<ref>{{cite journal |title=Exploring CYP2J2: lipid mediators, inhibitors and therapeutic implications |journal=Drug Discovery Today |date=September 2020 |volume=25 |issue=9 |pages=1744-1753 |doi=10.1016/j.drudis.2020.07.002 |pmc=|pmid=32652311|author=Marco Sisignano, Dieter Steinhilber, Michael J Parnham, Gerd Geisslinger}}</ref>
== See also == * Juglone
== References == {{reflist}}
Category:1,4-Naphthoquinones Category:Hydroxynaphthoquinones Category:Plant toxins Category:CYP2J2 inhibitors