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	{{chembox		{{chembox
			| Verifiedfields = changed
⚫	| verifiedrevid = 441731382
			| Watchedfields = changed
⚫	| Name = Methyl jasmonate
		⚫	| verifiedrevid = 455007441
	| ImageFile = methyl jasmonate skeletal.svg
		⚫	| Name = Methyl jasmonate
⚫	| ImageSize = 150px
	| ImageName = Methyl jasmonate		| ImageFile = methyl jasmonate skeletal.svg
		⚫	| ImageSize = 150px
⚫	| IUPACName = Methyl (1R,2R)-3-Oxo-2-(2Z)-2-<br />pentenyl-cyclopentaneacetate
	| OtherNames = Methyl jasmonate		| ImageName = Methyl jasmonate
		⚫	| IUPACName = Methyl (1''R'',2''R'')-3-Oxo-2-(2''Z'')-2-<wbr />pentenyl-cyclopentaneacetate
⚫	| Section1 = {{Chembox Identifiers
			| OtherNames = Methyl jasmonate
⚫	| CASNo = 39924-52-2
		⚫	|Section1={{Chembox Identifiers
⚫	| SMILES = O=C1(C/C=C\CC) (CC(OC)=O)CC1
			| CASNo_Ref = {{cascite|correct|??}}
		⚫	| CASNo = 1211-29-6
			| UNII_Ref = {{fdacite|correct|FDA}}
			| UNII = 900N171A0F
			| ChEBI_Ref = {{ebicite|changed|EBI}}
			| ChEBI = 15929
		⚫	| SMILES = O=C1(C/C=C\CC)(CC(OC)=O)CC1
			| EINECS = 243-497-1
			| PubChem = 5281929
			| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
			| ChemSpiderID = 4445210
			| 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
			| InChIKey = GEWDNTWNSAZUDX-WQMVXFAEBM
			| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
			| StdInChI = 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
			| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
			| StdInChIKey = GEWDNTWNSAZUDX-WQMVXFAESA-N
			| RTECS =
			| MeSHName =
			| KEGG_Ref = {{keggcite|changed|kegg}}
			| KEGG = C11512
	}}		}}
	| Section2 = {{Chembox Properties		|Section2={{Chembox Properties
	| Formula = ]<sub>13</sub>]<sub>20</sub>]<sub>3</sub>		| Formula = ]<sub>13</sub>]<sub>20</sub>]<sub>3</sub>
	| MolarMass = 224.3 g/mol		| MolarMass = 224.3 g/mol
	| Appearance = Colorless liquid		| Appearance = Colorless liquid
	| Density =		| Density =
	| MeltingPt =<25 °C		| MeltingPt=<
			| MeltingPtC = 25
	| BoilingPt = 88-90 °C at 0.1 mmHg
			| BoilingPtC = 88 to 90
			| BoilingPt_notes = at 0.1 mmHg
	}}		}}
	}}		}}
	'''Methyl jasmonate''' (MeJA) is a ] used in plant defense and many diverse developmental pathways such as seed germination, root growth, flowering, fruit ripening, and senescense.<ref>Cheong, Jong Joo and Yang Do Choi. ]'', 2003. Retrieved on 2010-10-27.</ref> Methyl jasmonate is derived from jasmonic acid and the reaction is catalyzed by S-adenosyl-L-methionine:jasmonic acid carboxyl methyltransferase.<ref></ref>		'''Methyl jasmonate''' (abbreviated '''MeJA''') is a ] used in plant defense and many diverse developmental pathways such as ], ], ], ], and ].<ref>{{cite journal|last1=Cheong|first1=Jong-Joo|last2=Choi|first2=Yang Do|title=Methyl jasmonate as a vital substance in plants|journal=Trends in Genetics|date=July 2003|volume=19|issue=7|pages=409–413|doi=10.1016/S0168-9525(03)00138-0|pmid=12850447}}</ref> Methyl jasmonate is derived from ] and the reaction is catalyzed by ''S''-adenosyl-{{sc|L}}-methionine:jasmonic acid carboxyl methyltransferase.<ref>{{cite web|last=Christie |first=William W. |archive-url=https://web.archive.org/web/20150630035136/http://lipidlibrary.aocs.org/Lipids/eicplant/index.htm |url=http://lipidlibrary.aocs.org/Lipids/eicplant/index.htm |title=Plant oxylipins: Chemistry and biology |date=22 May 2014 |archive-date=30 June 2015 |access-date=11 July 2017}}</ref>
⚫	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.<ref>Tao Xu et al. , 2003. Retrieved on 2010-10-27.</ref>
			==Description==
	MeJA can induce the plant to produce multiple different types of defense chemicals such as photoalexins (antimicrobial),<ref>]'', 1993. Retrieved on 2010-10-27.</ref> nicotine or proteinase inhibitors.<ref>Tao Xu et al. , 2003. Retrieved on 2010-10-27.</ref> MeJA activates the proteinase inhibitor genes (a defensive reaction within plants) through a receptor-mediated signal transduction pathway.<ref>Farmer, E. and C. Ryan , 1990. Retrieved on 2010-10-27.</ref> The proteinase inhibitors interfere with the insect digestive process and discourage the insect from eating the plant again.<ref>Tao Xu et al. </ref>
		⚫	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 ]. An herbivorous attack on a plant causes it to produce MeJA both for internal defense and for a signaling compound to other plants.<ref name="scichina">{{cite journal|last1=Farmer|first1=E. E.|last2=Ryan|first2=C. A.|title=Interplant communication: airborne methyl jasmonate induces synthesis of proteinase inhibitors in plant leaves.|journal=Proceedings of the National Academy of Sciences|date=1 October 1990|volume=87|issue=19|pages=7713–7716|doi=10.1073/pnas.87.19.7713|pmid=11607107|pmc=54818|bibcode=1990PNAS...87.7713F|doi-access=free}}</ref>
			==Defense chemicals==
	MeJA has been used to stimulate traumatic resin duct production in lodgepole pine trees. This can be used as a defense against many insect attackers as a type of vaccine.
			MeJA can induce the plant to produce multiple different types of defense chemicals such as ]s (antimicrobial),<ref>{{cite journal|last=Stanley |first=D. |url=http://www.ars.usda.gov/is/ar/archive/feb98/fres0298.htm |title=Keeping Freshness in Fresh-Cut Produce |journal=Agricultural Research Magazine |publisher=] |date=February 1998 |access-date=27 October 2010}}</ref> ] or ].<ref name="scichina" /> 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 ] production in ] trees.<ref>{{cite journal|last1=Martin |first1=D. M. |last2=Gershenzon |first2=J. |last3=Bohlmann |first3=J. |url=http://www.plantphysiol.org/content/132/3/1586.abstract?ijkey=b7eb803e056bd98617b4eea8cd4153f679c6ced0&keytype2=tf_ipsecsha |title=Induction of Volatile Terpene Biosynthesis and Diurnal Emission by Methyl Jasmonate in Foliage of Norway Spruce |journal=] |date=2003 |volume=132 |issue=3 |pages=1586–1599 |doi=10.1104/pp.103.021196 |pmid=12857838 |pmc=167096 |s2cid=23062454 |access-date=1 September 2016}}</ref> This can be used as a defense against many insect attackers as a type of vaccine.<ref>{{Cite journal |last1=Mageroy |first1=Melissa H. |last2=Christiansen |first2=Erik |last3=Långström |first3=Bo |last4=Borg‐Karlson |first4=Anna‐Karin |last5=Solheim |first5=Halvor |last6=Björklund |first6=Niklas |last7=Zhao |first7=Tao |last8=Schmidt |first8=Axel |last9=Fossdal |first9=Carl Gunnar |last10=Krokene |first10=Paal |date=February 2020 |title=Priming of inducible defenses protects Norway spruce against tree‐killing bark beetles |url=https://onlinelibrary.wiley.com/doi/10.1111/pce.13661 |journal=Plant, Cell & Environment |language=en |volume=43 |issue=2 |pages=420–430 |doi=10.1111/pce.13661 |pmid=31677172 |s2cid=207834105 |issn=0140-7791|hdl=21.11116/0000-0004-E7D0-C |hdl-access=free }}</ref>
⚫	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.<ref>Radhika, V., J. Cost, W. Boland, and M. Heil. The role of jasmonates in floral nectar secretion. 2010. Retrieved on 2010-10-27.</ref> MeJA induces ethylene-forming enzyme activity, which increases the amount of ethylene to the amount necessary for fruit maturation.<ref>Berger, S., E. Bell, and J. Mullet. </ref>
			==Experiments==
⚫	Increased amounts of methyl jasmonate in plant roots have shown to inhibit their growth.<ref>Wasternack, C. </ref> It is predicted that the higher amounts of MeJa activate previously unexpressed genes within the roots to cause the growth inhibition.<ref>Berger, S., E. Bell, and J. Mullet. </ref>
			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'' (]), the accumulation of ] and ] compounds doubled in the spruce needle tissues, a response that normally is only triggered when the tissue is damaged.<ref>{{Cite journal |last1=Martin |first1=Diane M. |last2=Gershenzon |first2=Jonathan |last3=Bohlmann |first3=Jörg |date=July 2003 |title=Induction of Volatile Terpene Biosynthesis and Diurnal Emission by Methyl Jasmonate in Foliage of Norway Spruce |url=http://dx.doi.org/10.1104/pp.103.021196 |journal=Plant Physiology |volume=132 |issue=3 |pages=1586–1599 |doi=10.1104/pp.103.021196 |pmid=12857838 |pmc=167096 |issn=1532-2548}}</ref>
			In an experiment testing the effect of methyl jasmonate treatments on drought tolerance, ] 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.<ref>{{Cite journal |last=Wang |first=S. Y. |date=November 1999 |title=Methyl Jasmonate Reduces Water Stress in Strawberry |url=http://dx.doi.org/10.1007/pl00007060 |journal=Journal of Plant Growth Regulation |volume=18 |issue=3 |pages=127–134 |doi=10.1007/pl00007060 |pmid=10594248 |s2cid=1019939 |issn=0721-7595}}</ref>
⚫	Methyl jasmonate induces cytochrome c release in the mitochondria of cancer cells, leading to cell death, but does not harm normal cells. To be specific, it can cause cell death in chronic lymphocytic leukemia (CLL) 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 <ref>Rotem, R., A. Heyfets, O. Fingrut, D. Blickstein, M. Shaklai, and E. Flesher </ref>
			External application of methyl jasmonate has also shown a propensity for inducing an increased resistance to insect herbivory in some agricultural crops, such as ]s and ]. 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.<ref>{{Cite journal |last1=Avdiushko |first1=S. A. |last2=Brown |first2=G. C. |last3=Dahlman |first3=D. L. |last4=Hildebrand |first4=D. F. |date=1997-06-01 |title=Methyl Jasmonate Exposure Induces Insect Resistance in Cabbage and Tobacco |url=http://dx.doi.org/10.1093/ee/26.3.642 |journal=Environmental Entomology |volume=26 |issue=3 |pages=642–654 |doi=10.1093/ee/26.3.642 |issn=1938-2936}}</ref>
			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 ] effect is thought to be because of methyl jasmonate inducing resistance.<ref>{{cite journal|last1=Luzzatto |first1=T. |last2=Yishay |first2=M. |last3=Lipsky |first3=A. |last4=Ion |first4=A. |last5=Belausov |first5=E. |last6=Yedidia |first6=I. |title=Efficient, long-lasting resistance against the soft rot bacterium ''Pectobacterium carotovorum'' in calla lily provided by the plant activator methyl jasmonate |journal=] |volume=56 |issue=4 |pages=692–701 |date=August 2007 |doi=10.1111/j.1365-3059.2007.01622.x}}</ref>
		⚫	MeJA is also a plant hormone involved in ] (root) coiling, flowering, seed and fruit maturation. An increase of the hormone affects flowering time, flower morphology and the number of open flowers.<ref>{{cite journal|last1=Radhika |first1=V. |first2=J. |last2=Cost |first3=W. |last3=Boland |first4=M. |last4=Heil |title=The role of jasmonates in floral nectar secretion |journal=] |date=2010 |volume=5 |issue=2 |pages=e9265 |doi=10.1371/journal.pone.0009265 |pmid=20174464 |pmc=2824824 |doi-access=free }}</ref> MeJA induces ethylene-forming enzyme activity, which increases the amount of ethylene to the amount necessary for fruit maturation.<ref name="ncbi">{{cite journal|last1=Berger|first1=S.|last2=Bell|first2=E.|last3=Mullet|first3=J. E.|title=Two Methyl Jasmonate-Insensitive Mutants Show Altered Expression of AtVsp in Response to Methyl Jasmonate and Wounding|journal=Plant Physiology|date=June 1996|volume=111|issue=2|pages=525–531|doi=10.1104/pp.111.2.525|pmid=12226307|pmc=157863}}</ref>
		⚫	Increased amounts of methyl jasmonate in plant roots have shown to inhibit their growth.<ref>{{cite journal|last=Wasternack |first=C. |archive-url=https://web.archive.org/web/20120625031415/http://aob.oxfordjournals.org/content/100/4/681.full#T1 |url=http://aob.oxfordjournals.org/content/100/4/681.full#T1 |title=Jasmonates: An Update on Biosynthesis, Signal Transduction and Action in Plant Stress Response, Growth and Development |journal=] |date=2007 |volume=100 |issue=4 |pages=681–697 |doi=10.1093/aob/mcm079 |pmid=17513307 |pmc=2749622 |archive-date=25 June 2012 |access-date=27 October 2010}}</ref> It is predicted that the higher amounts of MeJA activate previously unexpressed genes within the roots to cause the growth inhibition.<ref name="ncbi" />
			==Cancer cells==
		⚫	Methyl jasmonate induces ] release in the ] of cancer cells, leading to ], but does not harm normal cells. Specifically, it can cause cell death in ] 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.<ref>{{cite journal|last1=Rotem |first1=R. |first2=A. |last2=Heyfets |first3=O. |last3=Fingrut |first4=D. |last4=Blickstein |first5=M. |last5=Shaklai |first6=E. |last6=Flesher |date=2005 |url=http://cancerres.aacrjournals.org/content/65/5/1984.full |title=Jasmonates: novel anticancer agents acting directly and selectively on human cancer cell mitochondria |journal=] |volume=65 |issue=5 |pages=1984–1993 |doi=10.1158/0008-5472.CAN-04-3091 |pmid=15753398 |s2cid=2151552 |access-date=27 October 2010}}</ref>
	==See also==		==See also==
	* ]		* ]
			* ]
	==References==		==References==
			{{Reflist|30em}}
	<references/>
	==External links==		==External links==
	*		*
		⚫	* US Patent Issued on October 22, 2002
	*
			* , Leukemia, Nature, April 2002, Volume 16, Number 4, Pages 608–616
⚫	* US Patent Issued on October 22, 2002
	* , Leukemia, Nature, April 2002, Volume 16, Number 4, Pages 608-616		* , British Journal of Pharmacology (2005) 146, 800–808. {{doi|10.1038/sj.bjp.0706394}}; published online 19 September 2005
	* , British Journal of Pharmacology (2005) 146, 800–808. doi:10.1038/sj.bjp.0706394; published online 19 September 2005
	{{Plant_hormones}}		{{Plant_hormones}}
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