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MetaCyc Pathway: diphyllin biosynthesis
Inferred from experiment

Enzyme View:

Pathway diagram: diphyllin 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 BiosynthesisPhenylpropanoid Derivatives BiosynthesisLignans Biosynthesis

Some taxa known to possess this pathway include : Linum, Linum perenne

Expected Taxonomic Range: Viridiplantae

The structural biopolymers lignins and lignans accomplish different tasks in plants, lignins are involved in structural support and lignans have been attributed to protection and defense as their primary physiological functions. Taken together lignins and lignans count for about 30% of carbon in vascular plants [Lewis99].

Cell suspension cultures of Linum perenne accumulate the arylnaphthalene lignan diphyllin which is a glycoside of justicidin B, [Vasilev06]. There is growing interest in lignans like justicidin B and diphyllin and their synthetic derivatives due to their application in cancer chemotherapy and other pharmacological effects [Mohagheghzadeh02]. diphyllin and its derivatives are putative remedies for topical chronic inflammatory disorders such as dermatitis and psoriasis. An acetylapioside derivative of diphyllin is a 5-lipoxygenase inhibitor [Prieto02].

The dihydroarylnaphthalenes are mostly concentrated in the aerial part of Linum plant. The enzyme justicidin B 7-hydroxylase was isolated and characterized. This enzyme catalyzes the last step in the biosynthesis of diphyllin by introducing a hydroxyl group in position 7 of justicidin B [Hemmati].

Created 14-Jun-2011 by Pujar A, Boyce Thompson Institute


Hemmati: Hemmati S, Schneider B, Schmidt TJ, Federolf K, Alfermann AW, Fuss E "Justicidin B 7-hydroxylase, a cytochrome P450 monooxygenase from cell cultures of Linum perenne Himmelszelt involved in the biosynthesis of diphyllin." Phytochemistry 68(22-24);2736-43. PMID: 17997463

Lewis99: Lewis NG, Davin LB, Sarkanen S (1999). "The nature and function of lignins." In: Comprehensive natural products chemistry Vol. 3: Barton Sir DHR, Nakanishi K. (eds.-in-chief), Carbohydrates and their derivatives including tannins, cellulose and related lignins. Amsterdam, New York: Elsevier 1999, 617-745.

Mohagheghzadeh02: Mohagheghzadeh A, Schmidt TJ, Alfermann AW (2002). "Arylnaphthalene lignans from in vitro cultures of Linum austriacum." J Nat Prod 65(1);69-71. PMID: 11809070

Prieto02: Prieto JM, Giner RM, Recio Mf MC, Schinella G, Manez S, Rios JL (2002). "Diphyllin acetylapioside, a 5-lipoxygenase inhibitor from Haplophyllum hispanicum." Planta Med 68(4);359-60. PMID: 11988863

Vasilev06: Vasilev N, Elfahmi , Bos R, Kayser O, Momekov G, Konstantinov S, Ionkova I (2006). "Production of justicidin B, a cytotoxic arylnaphthalene lignan from genetically transformed root cultures of Linum leonii." J Nat Prod 69(7);1014-7. PMID: 16872135

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

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

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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 Sun May 1, 2016, biocyc14.