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Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
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MetaCyc Pathway: sorgoleone 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: Biosynthesis Secondary Metabolites Biosynthesis Phenylpropanoid Derivatives Biosynthesis Quinone Secondary Metabolites Biosynthesis

Some taxa known to possess this pathway include ? : Sorghum bicolor

Expected Taxonomic Range: Sorghum

Summary:
Sorgoleone is an allelochemical compound synthesized by sorghum root hairs. Allelochemicals produced by one plant species inhibit the growth of another. The allelopathy of sorghum was first observed from reduced growth of other crop species when grown in rotation with sorghum.

Labeling studies suggested the involvement of a polyketide pathway, by a polyketide synthase, in forming the quinone head of sorgoleone and attaching the fatty acid tail [Dayan03]. The enzyme catalyzing this condensation reaction, alkylresorcinol synthase, has been recently characterized [Cook10]. The sorgoleone fatty acid tail has an unusual terminal double bond introduced by a novel desaturase [Pan07]. The reduced form of sorgoleone, dihydrosogoleone, is rapidly oxidized to the highly phytotoxic sorgoleone upon exudation into the soil.

Citations: [Baerson08]

Credits:
Created 30-Jul-2008 by Zhang P , TAIR
Revised 12-Apr-2010 by Zhang P , TAIR


References

Baerson08: Baerson SR, Dayan FE, Rimando AM, Nanayakkara NP, Liu CJ, Schroder J, Fishbein M, Pan Z, Kagan IA, Pratt LH, Cordonnier-Pratt MM, Duke SO (2008). "A functional genomics investigation of allelochemical biosynthesis in Sorghum bicolor root hairs." J Biol Chem 283(6);3231-47. PMID: 17998204

Cook10: Cook D, Rimando AM, Clemente TE, Schroder J, Dayan FE, Nanayakkara NP, Pan Z, Noonan BP, Fishbein M, Abe I, Duke SO, Baerson SR (2010). "Alkylresorcinol Synthases Expressed in Sorghum bicolor Root Hairs Play an Essential Role in the Biosynthesis of the Allelopathic Benzoquinone Sorgoleone." Plant Cell. PMID: 20348430

Dayan03: Dayan FE, Kagan IA, Rimando AM (2003). "Elucidation of the biosynthetic pathway of the allelochemical sorgoleone using retrobiosynthetic NMR analysis." J Biol Chem 278(31);28607-11. PMID: 12771136

Pan07: Pan Z, Rimando AM, Baerson SR, Fishbein M, Duke SO (2007). "Functional characterization of desaturases involved in the formation of the terminal double bond of an unusual 16:3Delta(9,12,150) fatty acid isolated from Sorghum bicolor root hairs." J Biol Chem 282(7);4326-35. PMID: 17178719

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."

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 SRI International Pathway Tools version 18.5 on Mon Nov 24, 2014, biocyc14.