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MetaCyc Pathway: jasmonoyl-amino acid conjugates biosynthesis II

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-amino acid conjugates biosynthesis, JA-amino acid conjugates biosynthesis, jasmonic acid-amino acid conjugates biosynthesis, jasmonoyl-amino acid biosynthesis, jasmonyl-amino acid conjugates biosynthesis

Superclasses: Biosynthesis Hormones Biosynthesis Plant Hormones Biosynthesis Jasmonates Biosynthesis

Some taxa known to possess this pathway include ? : Nicotiana attenuata

Expected Taxonomic Range: Viridiplantae

Summary:
Jasmonates an important class of compounds related to jasmonic acid, are found throughout the plant kingdom as well as in fungi [Wasternack07]. These compounds may participate in a number of biological processes including resistance to herbivores and some pathogens, protection against ozone, senescence, and reproductive development (reviewed in [Browse08, Wasternack07]).

Many different jasmonate precursors and jasmonate derivatives have biological activity, including jasmonyl (JA)-amino acid conjugates. Different species may have a different array of JA-amino acid conjugates, and the biological activity of each compound may differ between species. For example, jasmonyl-isoleucine (JA-Ile) has been shown to have biological activity in a number of different plants, including Arabidopsis thaliana [Staswick04, Suza08], Nicotiana attenuata[Wang07b, Kang06], Achyranthes bidentata [Tamogami08], barley [Kramell97], tomato [Katsir08], rice [Tamogami97] and others. In Arabidopsis thaliana, JA-Ile promotes the interaction between COI1 (an F-box) protein and the JAZ1 repressor protein. In this manner, JA-Ile is believed to help destabilize the JAZ1 repressor and thereby promote JA-responsive transcription [Thines07]. COI1 and JAZ homologs have been found in other plants, such as tomato, where they also bind in a JA-Ile-dependent manner, [Katsir08], indicating that JA-Ile might have a similar function in other plant species. Additional studies in Arabidopsis thaliana suggest that the specific isomeric forms of the same jasmonate can have very different biological effects [Fonseca09].

Interestingly, in Polygonum longisetum, a weed commonly found in Japan, a treatment of 100 uM JA-Ile fails to stimulate the normal JA-responsive emissions of volatile sesquiterpenes [Tamogami07] indicating that even JA-Ile may not be similarly effective in all plants. Other differences in biological activity have been observed across species for many other conjugates including JA-ACC, JA-leucine, and JA-valine.

In N.attenuata, jasmonate signaling is an important part of the response to herbivory [Wasternack07]. The level of JA as well as JA-Ile, JA-Leu, JA-Val, and JA-Gln all rise in response to wounding and treatment with oral secretions from the herbivorous tobacco hornworm Manduca sexta. On the other hand, JA-Trp, JA-Met, and JA-ACC have not been detected in this species [Wasternack07]. JA-Ile is involved in herbivore resistance [Kang06], but JA-Val and JA-Leu do not appear to stimulate herbivore defense responses [Wang08a]. It is unclear whether these are storage forms of JA or catabolic intermediates. Another important phytohormone, indole-3-acetic acid (IAA), can be conjugated with several amino acids, as shown in the indole-3-acetyl-amide conjugate biosynthesis pathway for Arabidopsis thaliana. Some of these compounds, such as IAA-aspartate are targeted for further breakdown ([Ostin98], (see indole-3-acetate degradation IV), while others, such as, IAA-alanine may serve as storage forms. A family of amido hydrolases can release free, active IAA from some of these "storage" IAA conjugates [Sotelo95, Davies99]. But, to date, no JA-amido hydrolases (that can release free JA from the amino acid conjugates) have been identified in plants. However, this enzymatic activity has been detected in the fungus, Botryodiplodia theobromae [Hertel97]. Further work will be required to determine the metabolic and functional fate of the "inactive" JA-amino acid conjugates identified in N. attenuata.

Reduced levels of JAR4 and JAR6 transcripts lead to lower levels of JA-Ile, JA-Leu, and JA-Val, suggesting that the in vivo synthesis of these compounds requires these enzymes. JA-Gln levels are not affected in these mutants, indicating that at least one other enzyme capable of generating jasmonyl-amino acid conjugates exists in this species [Wang07b, Kang06].

Superpathways: superpathway of jasmonoyl-amino acid conjugates biosynthesis

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

Unification Links: PlantCyc:PWY-6233

Credits:
Created 24-Apr-2009 by Dreher KA , TAIR


References

Browse08: Browse J (2008). "Jasmonate Passes Muster: A Receptor and Targets for the Defense Hormone." Annu Rev Plant Biol. PMID: 19025383

Davies99: Davies RT, Goetz DH, Lasswell J, Anderson MN, Bartel B (1999). "IAR3 encodes an auxin conjugate hydrolase from Arabidopsis." Plant Cell 11(3);365-76. PMID: 10072397

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

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

Hertel97: Hertel SC, Knofel HD, Kramell R, Miersch O (1997). "Partial purification and characterization of a jasmonic acid conjugate cleaving amidohydrolase from the fungus Botryodiplodia theobromae." FEBS Lett 407(1);105-10. PMID: 9141491

Kang06: Kang JH, Wang L, Giri A, Baldwin IT (2006). "Silencing threonine deaminase and JAR4 in Nicotiana attenuata impairs jasmonic acid-isoleucine-mediated defenses against Manduca sexta." Plant Cell 18(11);3303-20. PMID: 17085687

Katsir08: Katsir L, Schilmiller AL, Staswick PE, He SY, Howe GA (2008). "COI1 is a critical component of a receptor for jasmonate and the bacterial virulence factor coronatine." Proc Natl Acad Sci U S A 105(19);7100-5. PMID: 18458331

Kramell97: Kramell R, Miersch O, Hause B, Ortel B, Parthier B, Wasternack C (1997). "Amino acid conjugates of jasmonic acid induce jasmonate-responsive gene expression in barley (Hordeum vulgare L.) leaves." FEBS Lett 414(2);197-202. PMID: 9315685

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

Ostin98: Ostin A, Kowalyczk M, Bhalerao RP, Sandberg G (1998). "Metabolism of indole-3-acetic acid in Arabidopsis." Plant Physiol 118(1);285-96. PMID: 9733548

Sotelo95: Sotelo A, Contreras E, Flores S (1995). "Nutritional value and content of antinutritional compounds and toxics in ten wild legumes of Yucatan Peninsula." Plant Foods Hum Nutr 47(2);115-23. PMID: 7792259

Staswick04: Staswick PE, Tiryaki I (2004). "The oxylipin signal jasmonic acid is activated by an enzyme that conjugates it to isoleucine in Arabidopsis." Plant Cell 16(8);2117-27. PMID: 15258265

Suza08: Suza WP, Staswick PE (2008). "The role of JAR1 in Jasmonoyl-L: -isoleucine production during Arabidopsis wound response." Planta 227(6);1221-32. PMID: 18247047

Tamogami07: Tamogami, S., Narita, Y., Suzuki, S., Nishizawa, T., Hanai, H., Noma, M. (2007). "Volatile sesquiterpenes emitted from leaves of Polygonum longisetum treated with jasmonic acid and its amide conjugates." Journal of Pesticide Science. 32 (3): 264269.

Tamogami08: Tamogami S, Rakwal R, Agrawal GK (2008). "Interplant communication: airborne methyl jasmonate is essentially converted into JA and JA-Ile activating jasmonate signaling pathway and VOCs emission." Biochem Biophys Res Commun 376(4);723-7. PMID: 18812165

Tamogami97: Tamogami S, Rakwal R, Kodama O (1997). "Phytoalexin production by amino acid conjugates of jasmonic acid through induction of naringenin-7-O-methyltransferase, a key enzyme on phytoalexin biosynthesis in rice (Oryza sativa L.)." FEBS Lett 401(2-3);239-42. PMID: 9013895

Thines07: Thines B, Katsir L, Melotto M, Niu Y, Mandaokar A, Liu G, Nomura K, He SY, Howe GA, Browse J (2007). "JAZ repressor proteins are targets of the SCF(COI1) complex during jasmonate signalling." Nature 448(7154);661-5. PMID: 17637677

Wang07b: Wang L, Halitschke R, Kang JH, Berg A, Harnisch F, Baldwin IT (2007). "Independently silencing two JAR family members impairs levels of trypsin proteinase inhibitors but not nicotine." Planta 226(1);159-67. PMID: 17273867

Wang08a: Wang L, Allmann S, Wu J, Baldwin IT (2008). "Comparisons of LIPOXYGENASE3- and JASMONATE-RESISTANT4/6-silenced plants reveal that jasmonic acid and jasmonic acid-amino acid conjugates play different roles in herbivore resistance of Nicotiana attenuata." Plant Physiol 146(3);904-15. PMID: 18065562

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

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

Sembdner93: Sembdner, G., Parthier, B. (1993). "The Biochemistry and the Physiological and Molecular Actions of Jasmonates." Annual Review of Plant Physiology and Plant Molecular Biology. 44: 569-589.


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 Sat Nov 22, 2014, BIOCYC13A.