Plumbagin

Plumbagin

Chembox new
Name = Plumbagin
ImageFile = Plumbagin.png IUPACName = 5-hydroxy-2-methyl-naphthalene-1,4-dione
OtherNames =
Section1 = Chembox Identifiers
CASNo = 481-42-5
SMILES = CC1=CC(=O)C2=C(C1=O)C=CC=C2O
Section2 = Chembox Properties
Formula = C11H8O3
MolarMass = 188.17942 g/mol
Density =
MeltingPt =
BoilingPt =
Solubility =

Plumbagin (5-Hydroxy-2-methyl-1,4-naphthoquinone) is a plant-derived naphthoquinone possessing a number of pharmacological activities. A yellow pigment. [http://www.drugs.com/npp/black-walnut.html] It has been shown to have antimicrobial activity. [Didry, N., L. Dubrevil & M. Pinkas 1994. Activity of anthraquinonic and naphthoquinonic compounds on oral bacteria. "Die Pharmazie" 49(9): 681–683.] [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.] |511 KiB "Mem Inst Oswaldo Cruz" 98(7): 959–961.] In animals, it has antimalarial, [Likhitwitayawuid, K., R. Kaewamatawong, N. Ruangrungsi & J. Krungkrai 1998. Antimalarial naphthoquinones from "Nepenthes thorelii". "Planta Medica" 64(3): 237–241.] anticarcinogenic, [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.] [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] cardiotonic, [Itoigawa, M., K. Takeya & H. Furukawa 1991. Cardiotonic action of plumbagin on guinea-pig papillary muscle. "Planta Medica" 57(4): 317–319.] antifertilityaction, [Bhargava, S.K. 1984. Effects of plumbagin on reproductive function of male dog. "Indian Journal of Experimental Biology" 22(3): 153–156.] and anti-atherosclerosis effects. [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.]

Plumbagin is named after the plant genus "Plumbago", from which it was originally isolated. [Van der Vijver, L.M. 1972. Distribution of plumbagin in the Plumbaginaceae. "Phytochemistry" 11: 3247–3248.]

Regarded as a toxin. [http://www.drugs.com/npp/black-walnut.html]

References


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