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MetaCyc Pathway: plumbagin biosynthesis
Inferred from experiment

Enzyme View:

Pathway diagram: plumbagin biosynthesis

This view shows enzymes only for those organisms listed below, in the list of taxa known to possess the pathway. If an enzyme name is shown in bold, there is experimental evidence for this enzymatic activity.

Superclasses: BiosynthesisSecondary Metabolites BiosynthesisPolyketides Biosynthesis

Some taxa known to possess this pathway include : Plumbago europaea, Plumbago indica

Expected Taxonomic Range: cellular organisms

plumbagine is the napthoquinone, 5-Hydroxy-2-methyl-1,4-naphthoquinone. It was isolated from Plumbago indica and subsequently identified in a number of microbes and other plants. This secondary metabolite has several pharmacological uses such as antimicrobial, antimalarial and anticancer agents. Its action on non-small lung cells has been demonstrated [Gomathinayagam]. Plumbagin's role as an antiproliferative agent shows that it disrupts the microtubule network by tubulin binding [Gomathinayagam]. It is a promising chemotherapeutic candidate for breast cancer [Thasni08]. It is a yellow colored pigment. plumbagine accumulates in the roots of Plumbago indica. plumbagine is made of 6 acetate units as seen in Drosophyllum lusitanicum and Plumbago europaea [Springob07]. The basic skeleton of the napthpthaquinone plumbagine is produced by a polyketide synthase.

Created 10-Aug-2009 by Pujar A, Boyce Thompson Institute


Gomathinayagam: Gomathinayagam R, Sowmyalakshmi S, Mardhatillah F, Kumar R, Akbarsha MA, Damodaran C "Anticancer mechanism of plumbagin, a natural compound, on non-small cell lung cancer cells." Anticancer Res 28(2A);785-92. PMID: 18507021

Springob07: Springob K, Samappito S, Jindaprasert A, Schmidt J, Page JE, De-Eknamkul W, Kutchan TM (2007). "A polyketide synthase of Plumbago indica that catalyzes the formation of hexaketide pyrones." FEBS J 274(2);406-17. PMID: 17229146

Thasni08: Thasni KA, Rakesh S, Rojini G, Ratheeshkumar T, Srinivas G, Priya S (2008). "Estrogen-dependent cell signaling and apoptosis in BRCA1-blocked BG1 ovarian cancer cells in response to plumbagin and other chemotherapeutic agents." Ann Oncol 19(4);696-705. PMID: 18187487

Other References Related to Enzymes, Genes, Subpathways, and Substrates of this Pathway

Bringmann98: Bringmann, G, Wohgarth, M, Rischer, H, Rlickert, M, Schlauer, J (1998). "The Polyketide Folding Mode in the Biogenesis of Isoshinanolone and Plumnbagin from Ancistrocladus heyneanus (Ancistrodadaceae).." Tetrahedron Letters, 39, 8445-8448.

Latendresse13: Latendresse M. (2013). "Computing Gibbs Free Energy of Compounds and Reactions in MetaCyc."

Mizuuchi09: Mizuuchi Y, Shi SP, Wanibuchi K, Kojima A, Morita H, Noguchi H, Abe I (2009). "Novel type III polyketide synthases from Aloe arborescens." FEBS J 276(8);2391-401. PMID: 19348024

Rubio06: Rubio S, Larson TR, Gonzalez-Guzman M, Alejandro S, Graham IA, Serrano R, Rodriguez PL (2006). "An Arabidopsis mutant impaired in coenzyme A biosynthesis is sugar dependent for seedling establishment." Plant Physiol 140(3);830-43. PMID: 16415216

Report Errors or Provide Feedback
Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
Page generated by Pathway Tools version 19.5 (software by SRI International) on Sat Apr 30, 2016, biocyc13.