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Methyl jasmonate

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(Redirected from C13H20O3)
Methyl jasmonate
Methyl jasmonate
Names
IUPAC name
Methyl (1R,2R)-3-Oxo-2-(2Z)-2-pentenyl-cyclopentaneacetate
Other names
Methyl jasmonate
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.013.562 Edit this at Wikidata
EC Number
  • 243-497-1
KEGG
UNII
  • InChI=1S/C13H20O3/c1-3-4-5-6-11-10(7-8-12(11)14)9-13(15)16-2/h4-5,10-11H,3,6-9H2,1-2H3/b5-4-/t10-,11-/m1/s1 ☒N
    Key: GEWDNTWNSAZUDX-WQMVXFAESA-N ☒N
  • InChI=1/C13H20O3/c1-3-4-5-6-11-10(7-8-12(11)14)9-13(15)16-2/h4-5,10-11H,3,6-9H2,1-2H3/b5-4-/t10-,11-/m1/s1
    Key: GEWDNTWNSAZUDX-WQMVXFAEBM
  • O=C1[C@H](C/C=C\CC)[C@@H](CC(OC)=O)CC1
Properties
C13H20O3
Molar mass 224.3 g/mol
Appearance Colorless liquid
Melting point < 25 °C (77 °F; 298 K)
Boiling point 88 to 90 °C (190 to 194 °F; 361 to 363 K) at 0.1 mmHg
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

Methyl jasmonate (abbreviated MeJA) is a volatile organic compound used in plant defense and many diverse developmental pathways such as seed germination, root growth, flowering, fruit ripening, and senescence.[1] Methyl jasmonate is derived from jasmonic acid and the reaction is catalyzed by S-adenosyl-L-methionine:jasmonic acid carboxyl methyltransferase.[2]

Description

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Plants produce jasmonic acid and methyl jasmonate in response to many biotic and abiotic stresses (in particular, herbivory and wounding), which build up in the damaged parts of the plant. The methyl jasmonate can be used to signal the original plant's defense systems or it can be spread by physical contact or through the air to produce a defensive reaction in unharmed plants. The unharmed plants absorb the airborne MeJA through either the stomata or diffusion through the leaf cell cytoplasm. An herbivorous attack on a plant causes it to produce MeJA both for internal defense and for a signaling compound to other plants.[3]

Defense chemicals

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MeJA can induce the plant to produce multiple different types of defense chemicals such as phytoalexins (antimicrobial),[4] nicotine or protease inhibitors.[3] The protease inhibitors interfere with the insect digestive process and discourage the insect from eating the plant again.

MeJA has been used to stimulate traumatic resin duct production in Norway spruce trees.[5] This can be used as a defense against many insect attackers as a type of vaccine.[6]

Experiments

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External application of methyl jasmonate has been shown to induce plant defensive responses against both biotic and abiotic stressors. When treatments of methyl jasmonate were applied to Picea abies (Norway spruce), the accumulation of monoterpene and sesquiterpene compounds doubled in the spruce needle tissues, a response that normally is only triggered when the tissue is damaged.[7]

In an experiment testing the effect of methyl jasmonate treatments on drought tolerance, strawberry plants were shown to alter their metabolism and were better able to withstand water stress and drought conditions by lowering the amount of transpiration, and membrane-lipid peroxidation.[8]

External application of methyl jasmonate has also shown a propensity for inducing an increased resistance to insect herbivory in some agricultural crops, such as brassicas and tobacco. Plants treated with methyl jasmonate and exposed to insect herbivores had significantly lower levels of herbivory, and the insect herbivores had slower development, when compared to untreated plants.[9]

In recent experiments, methyl jasmonate has been shown to be effective at preventing bacterial growth in plants when applied in a spray to the leaves. The antibacterial effect is thought to be because of methyl jasmonate inducing resistance.[10]

MeJA is also a plant hormone involved in tendril (root) coiling, flowering, seed and fruit maturation. An increase of the hormone affects flowering time, flower morphology and the number of open flowers.[11] MeJA induces ethylene-forming enzyme activity, which increases the amount of ethylene to the amount necessary for fruit maturation.[12]

Increased amounts of methyl jasmonate in plant roots have shown to inhibit their growth.[13] It is predicted that the higher amounts of MeJA activate previously unexpressed genes within the roots to cause the growth inhibition.[12]

Cancer cells

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Methyl jasmonate induces cytochrome C release in the mitochondria of cancer cells, leading to cell death, but does not harm normal cells. Specifically, it can cause cell death in B-cell chronic lymphocytic leukemia cells taken from human patients with this disease and then treated in tissue culture with methyl jasmonate. Treatment of isolated normal human blood lymphocytes did not result in cell death.[14]

See also

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References

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  1. ^ Cheong, Jong-Joo; Choi, Yang Do (July 2003). "Methyl jasmonate as a vital substance in plants". Trends in Genetics. 19 (7): 409–413. doi:10.1016/S0168-9525(03)00138-0. PMID 12850447.
  2. ^ Christie, William W. (22 May 2014). "Plant oxylipins: Chemistry and biology". Archived from the original on 30 June 2015. Retrieved 11 July 2017.
  3. ^ a b Farmer, E. E.; Ryan, C. A. (1 October 1990). "Interplant communication: airborne methyl jasmonate induces synthesis of proteinase inhibitors in plant leaves". Proceedings of the National Academy of Sciences. 87 (19): 7713–7716. Bibcode:1990PNAS...87.7713F. doi:10.1073/pnas.87.19.7713. PMC 54818. PMID 11607107.
  4. ^ Stanley, D. (February 1998). "Keeping Freshness in Fresh-Cut Produce". Agricultural Research Magazine. United States Department of Agriculture. Retrieved 27 October 2010.
  5. ^ Martin, D. M.; Gershenzon, J.; Bohlmann, J. (2003). "Induction of Volatile Terpene Biosynthesis and Diurnal Emission by Methyl Jasmonate in Foliage of Norway Spruce". Plant Physiology. 132 (3): 1586–1599. doi:10.1104/pp.103.021196. PMC 167096. PMID 12857838. S2CID 23062454. Retrieved 1 September 2016.
  6. ^ Mageroy, Melissa H.; Christiansen, Erik; Långström, Bo; Borg‐Karlson, Anna‐Karin; Solheim, Halvor; Björklund, Niklas; Zhao, Tao; Schmidt, Axel; Fossdal, Carl Gunnar; Krokene, Paal (February 2020). "Priming of inducible defenses protects Norway spruce against tree‐killing bark beetles". Plant, Cell & Environment. 43 (2): 420–430. doi:10.1111/pce.13661. hdl:21.11116/0000-0004-E7D0-C. ISSN 0140-7791. PMID 31677172. S2CID 207834105.
  7. ^ Martin, Diane M.; Gershenzon, Jonathan; Bohlmann, Jörg (July 2003). "Induction of Volatile Terpene Biosynthesis and Diurnal Emission by Methyl Jasmonate in Foliage of Norway Spruce". Plant Physiology. 132 (3): 1586–1599. doi:10.1104/pp.103.021196. ISSN 1532-2548. PMC 167096. PMID 12857838.
  8. ^ Wang, S. Y. (November 1999). "Methyl Jasmonate Reduces Water Stress in Strawberry". Journal of Plant Growth Regulation. 18 (3): 127–134. doi:10.1007/pl00007060. ISSN 0721-7595. PMID 10594248. S2CID 1019939.
  9. ^ Avdiushko, S. A.; Brown, G. C.; Dahlman, D. L.; Hildebrand, D. F. (1997-06-01). "Methyl Jasmonate Exposure Induces Insect Resistance in Cabbage and Tobacco". Environmental Entomology. 26 (3): 642–654. doi:10.1093/ee/26.3.642. ISSN 1938-2936.
  10. ^ Luzzatto, T.; Yishay, M.; Lipsky, A.; Ion, A.; Belausov, E.; Yedidia, I. (August 2007). "Efficient, long-lasting resistance against the soft rot bacterium Pectobacterium carotovorum in calla lily provided by the plant activator methyl jasmonate". Plant Pathology. 56 (4): 692–701. doi:10.1111/j.1365-3059.2007.01622.x.
  11. ^ Radhika, V.; Cost, J.; Boland, W.; Heil, M. (2010). "The role of jasmonates in floral nectar secretion". PLOS ONE. 5 (2): e9265. doi:10.1371/journal.pone.0009265. PMC 2824824. PMID 20174464.
  12. ^ a b Berger, S.; Bell, E.; Mullet, J. E. (June 1996). "Two Methyl Jasmonate-Insensitive Mutants Show Altered Expression of AtVsp in Response to Methyl Jasmonate and Wounding". Plant Physiology. 111 (2): 525–531. doi:10.1104/pp.111.2.525. PMC 157863. PMID 12226307.
  13. ^ Wasternack, C. (2007). "Jasmonates: An Update on Biosynthesis, Signal Transduction and Action in Plant Stress Response, Growth and Development". Annals of Botany. 100 (4): 681–697. doi:10.1093/aob/mcm079. PMC 2749622. PMID 17513307. Archived from the original on 25 June 2012. Retrieved 27 October 2010.
  14. ^ Rotem, R.; Heyfets, A.; Fingrut, O.; Blickstein, D.; Shaklai, M.; Flesher, E. (2005). "Jasmonates: novel anticancer agents acting directly and selectively on human cancer cell mitochondria". Cancer Research. 65 (5): 1984–1993. doi:10.1158/0008-5472.CAN-04-3091. PMID 15753398. S2CID 2151552. Retrieved 27 October 2010.
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