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MetaCyc Compound Class: a jasmonoyl-isoleucine

Synonyms: a JA-Ile, a jasmonate-isoleucine, a jasmonic acid-isoleucine, a jasmonic acid-isoleucine conjugate, a jasmonyl isoleucine

Superclasses: a hormone a plant hormone a jasmonate

Summary:
Jasmonoyl-isoleucine (JA-Ile) has been detected in Arabidopsis thaliana [Staswick04] and a number of other plant species [Tamogami08, Sembdner93, Wang07b]. There are two different naturally occurring stereoisomers of this compound, (-)-jasmonoyl-L-isoleucine and (+)-7-iso-jasmonoyl-L-isoleucine, that can spontaneously interconvert through epimerization [Fonseca09].

In Arabidopsis thaliana, JA-Ile promotes binding between the COI1 F-box protein and the JAZ1 repressor involved in jasmonic acid-mediated signaling [Thines07]. Therefore, JA-Ile promotes the degradation of JAZ1. Initial studies suggested that (-)-JA-Ile was a biologically active phytohormone [Sembdner93, Guranowski07]. However, later work shows that (+)-7-iso-jasmonoyl-L-isoleucine is the biologically active form of the compound [Fonseca09]. This compound exists at low levels in most commercial preparations of (-)-jasmonoyl-L-isoleucine and may explain the observed biological activity originally associated with (-)-JA-Ile. A pure preparation of that stereoisomer does not promote JAZ/COI1 binding in vitro [Fonseca09].

JA-Ile has also been detected in Nicotiana attenuata and plays a role in defense responses [Kang06] but it is unclear which form of JA-Ile is active in this process.

Chemical Formula: C18H29NO4

Instances:
(+)-7-iso-jasmonoyl-L-isoleucine ,
(-)-jasmonoyl-L-isoleucine ,
(3R, 7S)-12-hydroxy-jasmonoyl-L-isoleucine

Monoisotopic Molecular Weight: 323.2096584245 Daltons

SMILES: CCC=CCC1(C(CCC1=O)CC(NC(C(O)=O)C(C)CC)=O)

Standard Gibbs Free Energy of Change Formation (ΔfG in kcal/mol): 207.59248 Inferred by computational analysis [Latendresse13]

Reactions known to produce the compound:

jasmonoyl-amino acid conjugates biosynthesis I , jasmonoyl-amino acid conjugates biosynthesis II :
a jasmonic acid + L-isoleucine + ATP → a jasmonoyl-isoleucine + AMP + diphosphate

Not in pathways:
a prohormone + H2O → a hormone


References

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

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

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.

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

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

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


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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
Page generated by SRI International Pathway Tools version 18.5 on Wed Nov 26, 2014, biocyc11.