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MetaCyc Pathway: 9-lipoxygenase and 9-allene oxide synthase pathway
Inferred from experiment

Enzyme View:

Pathway diagram: 9-lipoxygenase and 9-allene oxide synthase pathway

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.

Synonyms: 9-LOX and 9-AOS pathway

Superclasses: BiosynthesisSecondary Metabolites BiosynthesisFatty Acid Derivatives Biosynthesis

Some taxa known to possess this pathway include : Hordeum vulgare, Solanum lycopersicum, Solanum tuberosum

Expected Taxonomic Range: Viridiplantae

Lipoxygenases (LOX) are ubiquitous enzymes in eukaryotes. Depending on the positional specificities, they are further classified as 9-LOX and 13-LOX, converting poly unsaturated fatty acids to 9-hydroperoxides and 13-hydroperoxides, respectively. In plants, most reported LOXs are 13-LOXs, which are important in the biosynthesis of plant hormone jasmonic acid.

Interestingly, potato has strong 9-lipoxygenase (9-LOX) activity. The preferred substrates for these enzymes are linoleate and α-linolenate, and the resulting products are the hydroperoxides (9S)-HPODE and 9(S)-HPOTE, respectively.

The major metabolic products from these hydroperoxides are divinyl ethers and epoxy alcohols, obtained via the activities of divinyl ether biosynthesis I (DES) and epoxy alcohol synthase (EAS), respectively. Divinyl ethers and epoxy alcohols are potato defense compounds (see divinyl ether biosynthesis I).

In addition to DES and EAS, a 9-allene oxide synthase (9-AOS) activity has been reported. To date, 9-AOS has only been detected in a few plants including tomato, barley and potato. The limited tissue distribution of 9-AOS suggested a specialized function in plant development control, rather than ubiquitous defensive roles as DES and EAS. It was shown that the (12Z)-9-hydroxy-10-oxo-octadec-12-enoate produced from (9S)-HPODE in Lemna paucicostata and Ipomoea nil functions as a component of a flower-inducing factor.

Citations: [Feussner02, Stumpe01, Gobel01, Kongrit06]

Superpathways: superpathway of lipoxygenase

Created 28-Nov-2006 by Zhang P, TAIR


Feussner02: Feussner I, Wasternack C (2002). "The lipoxygenase pathway." Annu Rev Plant Biol 2002;53;275-97. PMID: 12221977

Fonseca09: Fonseca S, Chini A, Hamberg M, Adie B, Porzel A, Kramell R, Miersch O, Wasternack C, Solano R (2009). "(+)-7-iso-Jasmonoyl-L-isoleucine is the endogenous bioactive jasmonate." Nat Chem Biol 5(5);344-50. PMID: 19349968

Gobel01: Gobel C, Feussner I, Schmidt A, Scheel D, Sanchez-Serrano J, Hamberg M, Rosahl S (2001). "Oxylipin profiling reveals the preferential stimulation of the 9-lipoxygenase pathway in elicitor-treated potato cells." J Biol Chem 276(9);6267-73. PMID: 11085991

Guranowski07: Guranowski A, Miersch O, Staswick PE, Suza W, Wasternack C (2007). "Substrate specificity and products of side-reactions catalyzed by jasmonate:amino acid synthetase (JAR1)." FEBS Lett 581(5);815-20. PMID: 17291501

Kongrit06: Kongrit D, Jisaka M, Kobayasi K, Nishigaichi Y, Nishimura K, Nagaya T, Yokota K (2006). "Molecular cloning, functional expression, and tissue distribution of a potato sprout allene oxide synthase involved in a 9-lipoxygenase pathway." Biosci Biotechnol Biochem 70(9);2160-8. PMID: 16960383

Mueller94a: Mueller MJ, Brodschelm W (1994). "Quantification of jasmonic acid by capillary gas chromatography-negative chemical ionization-mass spectrometry." Anal Biochem 218(2);425-35. PMID: 8074303

Stumpe01: Stumpe M, Kandzia R, Gobel C, Rosahl S, Feussner I (2001). "A pathogen-inducible divinyl ether synthase (CYP74D) from elicitor-treated potato suspension cells." FEBS Lett 507(3);371-6. PMID: 11696374

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

Bachmann02: Bachmann A, Hause B, Maucher H, Garbe E, Voros K, Weichert H, Wasternack C, Feussner I (2002). "Jasmonate-induced lipid peroxidation in barley leaves initiated by distinct 13-LOX forms of chloroplasts." Biol Chem 383(10);1645-57. PMID: 12452441

Bedord78: Bedord CJ, McMahon V, Adams B (1978). "alpha-linolenic acid biosynthesis in Cyanidium caldarium." Arch Biochem Biophys 185(1);15-20. PMID: 414660

Boeglin08: Boeglin WE, Itoh A, Zheng Y, Coffa G, Howe GA, Brash AR (2008). "Investigation of substrate binding and product stereochemistry issues in two linoleate 9-lipoxygenases." Lipids 43(11);979-87. PMID: 18795358

Brash99: Brash AR (1999). "Lipoxygenases: occurrence, functions, catalysis, and acquisition of substrate." J Biol Chem 274(34);23679-82. PMID: 10446122

Hughes01: Hughes RK, West SI, Hornostaj AR, Lawson DM, Fairhurst SA, Sanchez RO, Hough P, Robinson BH, Casey R (2001). "Probing a novel potato lipoxygenase with dual positional specificity reveals primary determinants of substrate binding and requirements for a surface hydrophobic loop and has implications for the role of lipoxygenases in tubers." Biochem J 353(Pt 2);345-55. PMID: 11139400

Kenyon72: Kenyon CN (1972). "Fatty acid composition of unicellular strains of blue-green algae." J Bacteriol 109(2);827-34. PMID: 4621688

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

Meesapyodsuk11: Meesapyodsuk D, Qiu X (2011). "A peroxygenase pathway involved in the biosynthesis of epoxy Fatty acids in oat." Plant Physiol 157(1);454-63. PMID: 21784965

Mizuno03: Mizuno K, Iida T, Takano A, Yokoyama M, Fujimura T (2003). "A new 9-lipoxygenase cDNA from developing rice seeds." Plant Cell Physiol 44(11);1168-75. PMID: 14634153

Royo96: Royo J, Vancanneyt G, Perez AG, Sanz C, Stormann K, Rosahl S, Sanchez-Serrano JJ (1996). "Characterization of three potato lipoxygenases with distinct enzymatic activities and different organ-specific and wound-regulated expression patterns." J Biol Chem 271(35);21012-9. PMID: 8702864

Vellosillo07: Vellosillo T, Martinez M, Lopez MA, Vicente J, Cascon T, Dolan L, Hamberg M, Castresana C (2007). "Oxylipins produced by the 9-lipoxygenase pathway in Arabidopsis regulate lateral root development and defense responses through a specific signaling cascade." Plant Cell 19(3);831-46. PMID: 17369372

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
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