MetaCyc Pathway: jasmonic acid biosynthesis
Inferred from experiment

Enzyme View:

Pathway diagram: jasmonic acid 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.

Synonyms: jasmonate biosynthesis

Superclasses: BiosynthesisHormones BiosynthesisPlant Hormones BiosynthesisJasmonates Biosynthesis
BiosynthesisSecondary Metabolites BiosynthesisFatty Acid Derivatives Biosynthesis

Some taxa known to possess this pathway include : Arabidopsis thaliana col, Solanum lycopersicum

Expected Taxonomic Range: Viridiplantae

Jasmonic acid (JA), its cyclic precursors and derivatives are collectively referred to as jasmonates (JAs). Jasmonates are important intracellular regulators mediating diverse developmental processes, such as seed germination, flower and fruit development, leaf abscission, and senescence [Creelman95]. In addition, jasmonates induce plant defense responses against a group of pathogens [Reymond98] and mechanical or herbivorous insect-driven wounding [Creelman92].

JA biosynthesis starts with the conversion of linolenate to 12-oxo-phytodienoate (OPDA) in the chloroplast, by sequential actions of lipoxygenase (LOX), allene oxide synthase (AOS) and allene oxide cyclase (AOC). OPDA once formed in the chloroplast needs to be transported into the peroxisome where it is reduced by OPDA reductase to give rise to 3-oxo-2(cis-2'-pentenyl)-cyclopentane-1-octanoate (OPC8). OPC8, in its CoA form, is converted to JA by shortening six carbons from the octanoate side chain via three cycles of beta oxidation. The final steps of JA synthesis is catalyzed by three core enzymes of the beta-oxidation cycle, acyl-CoA oxidase (ACX), multifunctional protein containing 2-trans-enoyl-CoA hydratase and 3-hydroxyacyl-CoA dehydrogenase activities, and 3-ketoacyl-CoA thiolase (KAT).

JA biosynthesis is regulated at the transcriptional level. Strong correlation of gene expression of the Arabidopsis OPR3 (At2g06050) with 13-LOX (At1g72520, At1g17420), AOC (At3g25780), AOS (At5g42650) and OPCL1 (At1g20510) was reported in [Koo06].

Citations: [Seo01, Farmer90, Hofmann06, Wasternack07]

Superpathways: superpathway of lipoxygenase

Variants: hydroxyjasmonate sulfate biosynthesis, jasmonoyl-amino acid conjugates biosynthesis I, jasmonoyl-amino acid conjugates biosynthesis II, tuberonate glucoside biosynthesis

Unification Links: AraCyc:PWY-735

Revised 19-Dec-2006 by Zhang P, TAIR


Creelman92: Creelman RA, Tierney ML, Mullet JE (1992). "Jasmonic acid/methyl jasmonate accumulate in wounded soybean hypocotyls and modulate wound gene expression." Proc Natl Acad Sci U S A 1992;89(11);4938-41. PMID: 1594598

Creelman95: Creelman RA, Mullet JE (1995). "Jasmonic acid distribution and action in plants: regulation during development and response to biotic and abiotic stress." Proc Natl Acad Sci U S A 1995;92(10);4114-9. PMID: 11607536

Farmer90: Farmer EE, Ryan CA (1990). "Interplant communication: airborne methyl jasmonate induces synthesis of proteinase inhibitors in plant leaves." Proc Natl Acad Sci U S A 1990;87(19);7713-6. PMID: 11607107

Hofmann06: Hofmann E, Zerbe P, Schaller F (2006). "The Crystal Structure of Arabidopsis thaliana Allene Oxide Cyclase: Insights into the Oxylipin Cyclization Reaction." Plant Cell 18(11);3201-17. PMID: 17085685

Koo06: Koo AJ, Chung HS, Kobayashi Y, Howe GA (2006). "Identification of a peroxisomal acyl-activating enzyme involved in the biosynthesis of jasmonic acid in Arabidopsis." J Biol Chem 281(44);33511-20. PMID: 16963437

Reymond98: Reymond P, Farmer EE (1998). "Jasmonate and salicylate as global signals for defense gene expression." Curr Opin Plant Biol 1998;1(5);404-11. PMID: 10066616

Seo01: Seo HS, Song JT, Cheong JJ, Lee YH, Lee YW, Hwang I, Lee JS, Choi YD (2001). "Jasmonic acid carboxyl methyltransferase: a key enzyme for jasmonate-regulated plant responses." Proc Natl Acad Sci U S A 2001;98(8);4788-93. PMID: 11287667

Wasternack07: Wasternack C (2007). "Jasmonates: an update on biosynthesis, signal transduction and action in plant stress response, growth and development." Ann Bot (Lond) 100(4);681-97. PMID: 17513307

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

Bell95: Bell E, Creelman RA, Mullet JE (1995). "A chloroplast lipoxygenase is required for wound-induced jasmonic acid accumulation in Arabidopsis." Proc Natl Acad Sci U S A 1995;92(19);8675-9. PMID: 7567995

Costa00: Costa CL, Arruda P, Benedetti CE (2000). "An Arabidopsis gene induced by wounding functionally homologous to flavoprotein oxidoreductases." Plant Mol Biol 44(1);61-71. PMID: 11094980

Cruz04: Cruz Castillo M, Martinez C, Buchala A, Metraux JP, Leon J (2004). "Gene-specific involvement of beta-oxidation in wound-activated responses in Arabidopsis." Plant Physiol 135(1);85-94. PMID: 15141068

Delker07: Delker C, Zolman BK, Miersch O, Wasternack C (2007). "Jasmonate biosynthesis in Arabidopsis thaliana requires peroxisomal beta-oxidation enzymes--additional proof by properties of pex6 and aim1." Phytochemistry 68(12);1642-50. PMID: 17544464

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

Hooks99: Hooks MA, Kellas F, Graham IA (1999). "Long-chain acyl-CoA oxidases of Arabidopsis." Plant J 20(1);1-13. PMID: 10571860

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."

Laudert96: Laudert D, Pfannschmidt U, Lottspeich F, Hollander-Czytko H, Weiler EW (1996). "Cloning, molecular and functional characterization of Arabidopsis thaliana allene oxide synthase (CYP 74), the first enzyme of the octadecanoid pathway to jasmonates." Plant Mol Biol 1996;31(2);323-35. PMID: 8756596

Li05a: Li C, Schilmiller AL, Liu G, Lee GI, Jayanty S, Sageman C, Vrebalov J, Giovannoni JJ, Yagi K, Kobayashi Y, Howe GA (2005). "Role of beta-oxidation in jasmonate biosynthesis and systemic wound signaling in tomato." Plant Cell 17(3);971-86. PMID: 15722469

Melan94: Melan MA, Enriquez A, Peterman TK (1994). "The LOX1 Gene of Arabidopsis Is Temporally and Spatially Regulated in Germinating Seedlings." Plant Physiol 105(1);385-393. PMID: 12232208

Mueller94: 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

Peng94: Peng YL, Shirano Y, Ohta H, Hibino T, Tanaka K, Shibata D (1994). "A novel lipoxygenase from rice. Primary structure and specific expression upon incompatible infection with rice blast fungus." J Biol Chem 269(5);3755-61. PMID: 7508918

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

Rylott06: Rylott EL, Eastmond PJ, Gilday AD, Slocombe SP, Larson TR, Baker A, Graham IA (2006). "The Arabidopsis thaliana multifunctional protein gene (MFP2) of peroxisomal beta-oxidation is essential for seedling establishment." Plant J 45(6);930-41. PMID: 16507084

Sanders00: Sanders PM, Lee PY, Biesgen C, Boone JD, Beals TP, Weiler EW, Goldberg RB (2000). "The arabidopsis DELAYED DEHISCENCE1 gene encodes an enzyme in the jasmonic acid synthesis pathway." Plant Cell 12(7);1041-61. PMID: 10899973

Schaller00: Schaller F, Biesgen C, Mussig C, Altmann T, Weiler EW (2000). "12-Oxophytodienoate reductase 3 (OPR3) is the isoenzyme involved in jasmonate biosynthesis." Planta 210(6);979-84. PMID: 10872231

Showing only 20 references. To show more, press the button "Show all references".

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 Wed May 4, 2016, biocyc13.