MetaCyc Pathway: sorgoleone biosynthesis
Inferred from experiment

Pathway diagram: sorgoleone biosynthesis

If an enzyme name is shown in bold, there is experimental evidence for this enzymatic activity.

Superclasses: BiosynthesisSecondary Metabolites BiosynthesisPhenylpropanoid Derivatives BiosynthesisQuinone Secondary Metabolites Biosynthesis

Some taxa known to possess this pathway include : Sorghum bicolor

Expected Taxonomic Range: Sorghum

Allelochemicals are chemicals produced by one plant species that inhibit the growth of another. The allelopathy of Sorghum bicolor (sorghum) was first observed from reduced growth of other crop species when grown in rotation with sorghum. One of the allelochemicals synthesized by Sorghum bicolor is sorgoleone, which is produced by root hairs.

Labeling studies suggested the involvement of a polyketide synthase in forming the quinone head of sorgoleone and attaching the fatty acid tail [Dayan03]. The enzyme catalyzing this condensation reaction, 5-pentadecatrienylresorcinol synthase, has been characterized [Cook10]. The sorgoleone fatty acid tail has an unusual terminal double bond introduced by a dedicated desaturase [Pan07a]. The reduced form of sorgoleone, dihydrosogoleone, is rapidly oxidized to the highly phytotoxic sorgoleone upon exudation into the soil.

Citations: [Baerson08]

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


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

Pan07a: 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."

Lederer94: Lederer F (1994). "The cytochrome b5-fold: an adaptable module." Biochimie 76(7);674-92. PMID: 7893819

Napier03: Napier JA, Michaelson LV, Sayanova O (2003). "The role of cytochrome b5 fusion desaturases in the synthesis of polyunsaturated fatty acids." Prostaglandins Leukot Essent Fatty Acids 68(2);135-43. PMID: 12538077

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

Strittmatter74: Strittmatter P, Spatz L, Corcoran D, Rogers MJ, Setlow B, Redline R (1974). "Purification and properties of rat liver microsomal stearyl coenzyme A desaturase." Proc Natl Acad Sci U S A 71(11);4565-9. PMID: 4373719

Stukey89: Stukey JE, McDonough VM, Martin CE (1989). "Isolation and characterization of OLE1, a gene affecting fatty acid desaturation from Saccharomyces cerevisiae." J Biol Chem 264(28);16537-44. PMID: 2674136

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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
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