Jasmonic Acid Synthesis

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Jasmonic Acid

      Jasmonic acid (JA), is a growth inhibitor, senescence-promoting substance. Jasmonates, such as jasmonic acid, are cyclopentanone derivatives synthesized from linolenic acid via the octadecanoic pathway.  JAs is structurally related to prostaglandins, which are autacoidal hormones found in mammals. JA is synthesized from alpha-linolenic acid, which is a C18 poly-unsaturated fatty acid.  It is synthesized from plant membranes by enzymes similar to lipase.  Key JA biosynthetic enzymes have chloroplast transit peptides that directing their import into the chloroplast.  Key enzymes include lipoxygenase, allene oxide synthase, and allene oxide cyclase.

      JA can be conjugated to amino acids, ie. leucine, valine, isoleucine and the sugar, B-glucoside using UDP-glucose.  (-)-JA and (-)-methyl jasmonate are major JAs in plants.  JA induces vegetative storage proteins, osmotin, thionin (antifungal) and defensin. It induces the phytoalexin-related enzymes chalcone synthase, PAL, and hydroxymethylglutaryl-COA reductase. Induces protease inhibitors to control insects.  JA and ethylene induce PR-3, PR-4, PDF1.2, chitinases (CHI-B), and hevein-like protein.

 12-oxo-phytodienoic acid is also a physiological signal for defense.

Jasmonic Acid biosynthetic pathway  

octadecanoid pathway (end product is JA)

     

 

 

 

 

 

 

     

   

   Phospholipase                       Literature summary       cDNAs for A2, C, D
    Lipoxygenase (adds an oxygen)   Literature summary        cDNAs for 2,3,4,5,7,C
   Allene oxide synthase 1, 2, 3
    Allene oxide cyclase  (Chloroplast)  Literature summary  cDNAs for

     12-oxo-phytodienoic acid reductase – Three isoforms in A. thal.  Only one makes    physiologically active JA.  What do the other two do, because they cannot substitute for the correct isoform encoded by OPR3. OPDA also can serve as a signal for defense (Howe, Stintzi)

 JA     (family includes cyclopentenones (eg. OPDA) and cyclopentanones of related structure                 and biosynthetic origin)   Literature summary

Refs:

Howe, G.A. 2001. PNAS 98:12315-19

Klessig, D.F, J. Durner, J. Shah, Y. Yang. 1998. Phytochemical Signals and Plant Microbe Interactions, ed. Romeo et al. Ch. 7. Plenum Press, NY. pp.119-137

Stintzi  et al. 2001.PNAS 98:12837-42