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Methyl jasmonate

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]

Methyl jasmonate
Names
IUPAC name
Methyl (1R,2R)-3-Oxo-2-(2Z)-2-pentenyl-cyclopentaneacetate
Other names
Methyl jasmonate
Identifiers
  • 1211-29-6 Y
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:15929 N
ChemSpider
  • 4445210 N
ECHA InfoCard 100.013.562
EC Number
  • 243-497-1
KEGG
  • C11512 N
  • 5281929
UNII
  • 900N171A0F Y
  • DTXSID3036731
  • 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 YN ?)

Description edit

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 edit

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 edit

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 edit

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 edit

References edit

  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). . 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). . 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.

External links edit

  • General information about methyl jasmonate
  • US Patent Issued on October 22, 2002
  • Plant stress hormones suppress the proliferation and induce apoptosis in human cancer cells, Leukemia, Nature, April 2002, Volume 16, Number 4, Pages 608–616
  • Jasmonates induce nonapoptotic death in high-resistance mutant p53-expressing B-lymphoma cells, British Journal of Pharmacology (2005) 146, 800–808. doi:10.1038/sj.bjp.0706394; published online 19 September 2005

methyl, jasmonate, abbreviated, meja, volatile, organic, compound, used, plant, defense, many, diverse, developmental, pathways, such, seed, germination, root, growth, flowering, fruit, ripening, senescence, derived, from, jasmonic, acid, reaction, catalyzed, . 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 Methyl jasmonate Names IUPAC name Methyl 1R 2R 3 Oxo 2 2Z 2 wbr pentenyl cyclopentaneacetate Other names Methyl jasmonate Identifiers CAS Number 1211 29 6 Y 3D model JSmol Interactive image ChEBI CHEBI 15929 N ChemSpider 4445210 N ECHA InfoCard 100 013 562 EC Number 243 497 1 KEGG C11512 N PubChem CID 5281929 UNII 900N171A0F Y CompTox Dashboard EPA DTXSID3036731 InChI 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 NKey GEWDNTWNSAZUDX WQMVXFAESA N NInChI 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 s1Key GEWDNTWNSAZUDX WQMVXFAEBM SMILES O C1 C H C C C CC C H CC OC O CC1 Properties Chemical formula C13H20O3 Molar mass 224 3 g mol Appearance Colorless liquid Melting point lt 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 Y N Infobox references Contents 1 Description 2 Defense chemicals 3 Experiments 4 Cancer cells 5 See also 6 References 7 External linksDescription editPlants 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 editMeJA 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 editExternal 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 editMethyl 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 editJasmonate Methyl dihydrojasmonateReferences edit 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 Christie William W 22 May 2014 Plant oxylipins Chemistry and biology Archived from the original on 30 June 2015 Retrieved 11 July 2017 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 Stanley D February 1998 Keeping Freshness in Fresh Cut Produce Agricultural Research Magazine United States Department of Agriculture Retrieved 27 October 2010 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 Mageroy Melissa H Christiansen Erik Langstrom Bo Borg Karlson Anna Karin Solheim Halvor Bjorklund 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 amp Environment 43 2 420 430 doi 10 1111 pce 13661 hdl 21 11116 0000 0004 E7D0 C ISSN 0140 7791 PMID 31677172 S2CID 207834105 Martin Diane M Gershenzon Jonathan Bohlmann Jorg 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 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 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 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 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 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 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 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 External links editGeneral information about methyl jasmonate Jasmonate pharmaceutical composition for treatment of cancer US Patent Issued on October 22 2002 Plant stress hormones suppress the proliferation and induce apoptosis in human cancer cells Leukemia Nature April 2002 Volume 16 Number 4 Pages 608 616 Jasmonates induce nonapoptotic death in high resistance mutant p53 expressing B lymphoma cells British Journal of Pharmacology 2005 146 800 808 doi 10 1038 sj bjp 0706394 published online 19 September 2005 Retrieved from https en wikipedia org w index php title Methyl jasmonate amp oldid 1170208102, wikipedia, wiki, book, books, library,

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