Jasmonic acid

Jasmonic acid
Ball-and-stick model of jasmonic acid
Names
IUPAC name
(1R,2R)-3-Oxo-2-(2Z)-2-pentenyl-cyclopentaneacetic acid
Other names
Jasmonic acid
(−)-Jasmonic acid
JA
Identifiers
6894-38-8 Yes
ChEBI CHEBI:18292 
ChemSpider 4444606 
Jmol-3D images Image
PubChem 5281166
Properties
C12H18O3
Molar mass 210.27 g/mol
Density ? g/cm3
Boiling point 160 °C (320 °F; 433 K) at 0.7 mmHg
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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Infobox references

Jasmonic acid (JA) is derived from the fatty acid linolenic acid. It is a member of the jasmonate class of plant hormones. It is biosynthesized from linolenic acid by the octadecanoid pathway.

The major function of JA and its various metabolites is regulating plant responses to abiotic and biotic stresses as well as plant growth and development.[1] Regulated plant growth and development processes include growth inhibition, senescence, tendril coiling, flower development and leaf abscission. JA is also responsible for tuber formation in potatoes and yams. It has an important role in response to wounding of plants and systemic acquired resistance. The Dgl gene is responsible for maintaining levels of JA during usual conditions in Zea mays as well as the preliminary release of jasmonic acid shortly after being fed upon.[2] When plants are attacked by insects, they respond by releasing JA, which activates the expression of protease inhibitors, among many other anti-herbivore defense compounds. These protease inhibitors prevent proteolytic activity of the insects' digestive proteases or "salivary proteins",[3] thereby stopping them from acquiring the needed nitrogen in the protein for their own growth.[4]

Jasmonic acid is also converted to a variety of derivatives including esters such as methyl jasmonate; it may also be conjugated to amino acids.

This chemical may have a role in pest control, according to an October 2008 BBC News report.[5] Researchers at the UK's Lancaster University have signed a licensing deal with an American company to market jasmonic acid as a seed treatment. JA seed treatment stimulates the natural anti-pest defenses of the plants that germinate from the treated seeds, without harming plant growth as happens when jasmonates are sprayed onto plants that have already started growing.[6] However, due to its antagonistic relationship with salicylic acid (an important chemical signal in pathogen defense) in some plant species, it may result in an increased susceptibility to viral agents and other pathogens.[7] In Zea mays, salicylic acid and JA are mediated by NPR1 (nonexpressor of pathogenesis-related genes1), which is essential in preventing herbivores from exploiting this antagonistic system.[8] An Armyworm like the Spodoptera spp., through unknown mechanisms, are able to increase the activity of the salicylic acid pathway in maize, resulting in the depression of JA synthesis, but thanks to NPR1 mediation, JA levels aren't decreased by a significant amount.[9]

References

  1. ↑ Delker, C.; Stenzel, I.; Hause, B.; Miersch, O.; Feussner, I.; Wasternack, C. (2006). "Jasmonate Biosynthesis in Arabidopsis thaliana - Enzymes, Products, Regulation". Plant Biology 8 (3): 297–306. doi:10.1055/s-2006-923935. PMID 16807821.
  2. ↑ Gális, I.; Gaquerel, E.; Pandey, S. P.; Baldwin, I. N. T. (2009). "Molecular mechanisms underlying plant memory in JA-mediated defence responses". Plant, Cell & Environment 32 (6): 617. doi:10.1111/j.1365-3040.2008.01862.x.
  3. ↑ Lutz, Diana (2012). Key part of plants' rapid response system revealed. Washington University in St. Louis. http://news.wustl.edu/news/Pages/23979.aspx
  4. ↑ Zavala, J. A.; Patankar, A. G.; Gase, K.; Hui, D.; Baldwin, I. T. (2004). "Manipulation of Endogenous Trypsin Proteinase Inhibitor Production in Nicotiana attenuata Demonstrates Their Function as Antiherbivore Defenses". Plant Physiology 134 (3): 1181–1190. doi:10.1104/pp.103.035634. PMC 389942. PMID 14976235.
  5. ↑ "Success for plants' pest control". BBC News. 2008-10-07. Retrieved 2010-05-05.
  6. ↑ Worrall, D.; Holroyd, G. H.; Moore, J. P.; Glowacz, M.; Croft, P.; Taylor, J. E.; Paul, N. D.; Roberts, M. R. (2012). "Treating seeds with activators of plant defence generates long-lasting priming of resistance to pests and pathogens.". New Phytologist 193 (3): 770–778. doi:10.1111/j.1469-8137.2011.03987.x. PMID 22142268.
  7. ↑ Lyons, R.; Manners, J. M.; Kazan, K. (2013). "Jasmonate biosynthesis and signaling in monocots: A comparative overview". Plant Cell Reports 32 (6): 815. doi:10.1007/s00299-013-1400-y.
  8. ↑ Ballaré, Carlos L. (2011). "Jasmonate-induced defenses: A tale of intelligence, collaborators and rascals". Trends in Plant Science 16 (5): 249–57. doi:10.1016/j.tplants.2010.12.001. PMID 21216178.
  9. ↑ Ballaré, Carlos L. (2011). "Jasmonate-induced defenses: A tale of intelligence, collaborators and rascals". Trends in Plant Science 16 (5): 249–57. doi:10.1016/j.tplants.2010.12.001. PMID 21216178.