Jasmonic acid
{{chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 420895015
| Name = Jasmonic acid
| ImageFile = Jasmonicacid.svg
| ImageName = Jasmonic acid
| ImageFile1 = Jasmonic acid molecule ball.png
| ImageSize1 = 200
| ImageAlt1 = Ball-and-stick model of jasmonic acid
| PIN = {(1R,2R)-3-Oxo-2-[(2Z)-pent-2-en-1-yl]cyclopentyl}acetic acid
| OtherNames = Jasmonic acid
(−)-Jasmonic acid
JA
(1R,2R)-3-Oxo-2-(2Z)-2-pentenylcyclopentylethanoic acid
{(1R,2R)-3-Oxo-2-[(2Z)-2-penten-1-yl]cyclopentyl}acetic acid
|Section1={{Chembox Identifiers
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 6894-38-8
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 6RI5N05OWW
| PubChem = 5281166
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = 4444606
| ChEBI_Ref = {{ebicite|changed|EBI}}
| ChEBI = 18292
| SMILES = CC/C=C\C[C@@H]1[C@H](CCC1=O)CC(=O)O
| InChI = 1/C12H18O3/c1-2-3-4-5-10-9(8-12(14)15)6-7-11(10)13/h3-4,9-10H,2,5-8H2,1H3,(H,14,15)/b4-3-/t9-,10-/m1/s1
| InChIKey = ZNJFBWYDHIGLCU-HWKXXFMVBZ
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| StdInChI = 1S/C12H18O3/c1-2-3-4-5-10-9(8-12(14)15)6-7-11(10)13/h3-4,9-10H,2,5-8H2,1H3,(H,14,15)/b4-3-/t9-,10-/m1/s1
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
| StdInChIKey = ZNJFBWYDHIGLCU-HWKXXFMVSA-N
}}
|Section2={{Chembox Properties
| Formula = C12H18O3
| MolarMass = 210.27 g/mol
| Density = 1.1 g/cm3
| MeltingPt =
| BoilingPtC = 160
| BoilingPt_notes = at 0.7 mmHg
}}
}}
Jasmonic acid (JA) is an organic compound found in several plants including jasmine. The molecule is a member of the jasmonate class of plant hormones. It is biosynthesized from linolenic acid by the octadecanoid pathway. It was first isolated in 1957 as the methyl ester of jasmonic acid by the Swiss chemist Édouard Demole and his colleagues.{{cite journal |last1=Demole |first1=E. |last2=Lederer |first2=E. |last3=Mercier |first3=D. |title=Isolement et determination de la structure du jasmonate de methyle, constituent odorant characteristique de l'essence de jasmin |journal=Helvetica Chimica Acta |date=1962 |volume=45 |issue=2 |pages=675–685 |doi=10.1002/hlca.19620450233 |trans-title=Isolation and determination of the structure of methyl jasmonate, the aromatic constituent characteristic of jasmine essential oil |language=fr}}
- {{cite journal |last1=Chapuis |first1=Christian |title=The chemistry and creative legacy of methyl jasmonate and hedione |journal=Perfumer & Flavorist |date=December 2011 |volume=36 |pages=36–48 |url=https://perfumerflavorist.texterity.com/perfumerflavorist/201112?pg=40#pg40}}
Biosynthesis
Its biosynthesis starts from the fatty acid linolenic acid, which is oxygenated by lipoxygenase (13-LOX), forming a hydroperoxide. This peroxide then cyclizes in the presence of allene oxide synthase to form an allene oxide. The rearrangement of allene oxide to form 12-oxophytodienoic acid is catalyzed by the enzyme allene oxide cyclase. A series of β-oxidations results in 7-isojasmonic acid. In the absence of enzyme, this isojasmonic acid isomerizes to jasmonic acid.{{Cite book|title=Medicinal Natural Products: A Biosynthetic Approach|url=https://archive.org/details/medicinalnatural00dewi_880|url-access=limited|last=Dewick|first=Paul|publisher=John Wiley & Sons|year=2009|isbn=978-0-470-74168-9|location=United Kingdom|pages=[https://archive.org/details/medicinalnatural00dewi_880/page/n49 42]–53}}
File:JasmonicAcidBiosyn.png core that is the site of the reactions.]]
Function
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.{{cite journal |last1=Delker |first1=C. |last2=Stenzel |first2=I. |last3=Hause |first3=B. |last4=Miersch |first4=O. |last5=Feussner |first5=I. |last6=Wasternack |first6=C. |doi=10.1055/s-2006-923935 |title=Jasmonate Biosynthesis in Arabidopsis thaliana – Enzymes, Products, Regulation |journal=Plant Biology |volume=8 |issue=3 |pages=297–306 |year=2006 |pmid=16807821 |bibcode=2006PlBio...8..297D }} 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.{{cite journal |doi=10.1111/j.1365-3040.2008.01862.x |pmid=18657055 |title=Molecular mechanisms underlying plant memory in JA-mediated defence responses |journal=Plant, Cell & Environment |volume=32 |issue=6 |pages=617–627 |year=2009 |last1=Gális |first1=I. |last2=Gaquerel |first2=E. |last3=Pandey |first3=S. P. |last4=Baldwin |first4=I. N. T.|doi-access=free |bibcode=2009PCEnv..32..617G }} 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",{{cite web |last=Lutz |first=Diana |date=2012 |title=Key part of plants' rapid response system revealed |publisher=Washington University in St. Louis |url=http://news.wustl.edu/news/Pages/23979.aspx |access-date=2012-07-24 |archive-date=2016-01-09 |archive-url=https://web.archive.org/web/20160109025253/https://news.wustl.edu/news/Pages/23979.aspx |url-status=dead }} thereby stopping them from acquiring the needed nitrogen in the protein for their own growth.{{cite journal |last1=Zavala |first1=J. A. |last2=Patankar |first2=A. G. |last3=Gase |first3=K. |last4=Hui |first4=D. |last5=Baldwin |first5=I. T. |title=Manipulation of Endogenous Trypsin Proteinase Inhibitor Production in Nicotiana attenuata Demonstrates Their Function as Antiherbivore Defenses |journal=Plant Physiology |volume=134 |issue=3 |pages=1181–1190 |date=2004 |doi=10.1104/pp.103.035634 |pmc=389942 |pmid=14976235}} JA also activates the expression of Polyphenol oxidase which promotes the production of quinolines. These can interfere with the insect's enzyme production and decrease the nutrition content of the ingested plant.{{Cite book|url=https://books.google.com/books?id=OlVknQAACAAJ|title=The Effects of Bacterial and Jasmonic Acid Treatments on Insects of Canola|date=2008|language=en}}
JA may have a role in pest control.{{cite news |url=http://news.bbc.co.uk/1/hi/sci/tech/7656078.stm |work=BBC News |title=Success for plants' pest control |date=2008-10-07 |access-date=2010-05-05}} Indeed, JA has been considered as a seed treatment in order to stimulate the natural anti-pest defenses of the plants that germinate from the treated seeds. In this application jasmonates are sprayed onto plants that have already started growing.{{cite journal |last1=Worrall |first1=D. |last2=Holroyd |first2=G. H. |last3=Moore |first3=J. P. |last4=Glowacz |first4=M. |last5=Croft |first5=P. |last6=Taylor |first6=J. E. |last7=Paul |first7=N. D. |last8=Roberts |first8=M. R. |date=2012 |title=Treating seeds with activators of plant defence generates long-lasting priming of resistance to pests and pathogens |journal=New Phytologist |volume=193 |issue=3 |pages=770–778 |doi=10.1111/j.1469-8137.2011.03987.x|pmid=22142268|url=https://eprints.lancs.ac.uk/id/eprint/50780/1/Worrall_NewPhytol_Pre_review.pdf |doi-access=free |bibcode=2012NewPh.193..770W }} These applications stimulate the production of protease inhibitor in the plant.{{Cite journal|last1=Farmer|first1=E. E.|last2=Johnson|first2=R. R.|last3=Ryan|first3=C. A.|date=March 1992|title=Regulation of expression of proteinase inhibitor genes by methyl jasmonate and jasmonic Acid|journal=Plant Physiology|volume=98|issue=3|pages=995–1002|issn=0032-0889|pmc=1080300|pmid=16668777|doi=10.1104/pp.98.3.995}} This production of protease inhibitor can protect the plant from insects, decreasing infestation rates and physical damage sustained due to herbivores.{{Cite journal|last1=Fouad|first1=Hany Ahmed|last2=El-Gepaly|first2=Hosam Mohamed Khalil Hammam|last3=Fouad|first3=Osama Ahmed|date=2016-08-26|title=Nanosilica and jasmonic acid as alternative methods for control Tuta absoluta (Meyrick) in tomato crop under field conditions|journal=Archives of Phytopathology and Plant Protection|volume=49|issue=13–14|pages=362–370|doi=10.1080/03235408.2016.1219446|bibcode=2016ArPPP..49..362F |s2cid=89119004|issn=0323-5408}} However, due to its antagonistic relationship with salicylic acid (an important signal in pathogen defense) in some plant species, it may result in an increased susceptibility to viral agents and other pathogens.{{cite journal |last1=Lyons |first1=R. |last2=Manners |first2=J. M. |last3=Kazan |first3=K. |date=2013 |title=Jasmonate biosynthesis and signaling in monocots: A comparative overview |journal=Plant Cell Reports |volume=32 |issue=6 |pages=815–27 |doi=10.1007/s00299-013-1400-y|pmid=23455708 |s2cid=10778582 }} 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.{{cite journal |last1=Ballaré |first1=Carlos L. |date=2011 |title=Jasmonate-induced defenses: A tale of intelligence, collaborators and rascals |journal=Trends in Plant Science |volume=16 |issue=5 |pages=249–57 |doi=10.1016/j.tplants.2010.12.001 |pmid=21216178|doi-access=free |bibcode=2011TPS....16..249B |hdl=11336/97245 |hdl-access=free }} Armyworms (Spodoptera caterpillars), 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.
Derivatives
{{Main|Jasmonate}}
Jasmonic acid is also converted to a variety of derivatives including the ester methyl jasmonate. This conversion is catalyzed by the jasmonic acid carboxyl methyltransferase enzyme.{{Cite journal|last1=Seo|first1=H.-S.|last2=Song|first2=J.-T.|last3=Cheong|first3=J.-J.|last4=Lee|first4=Y.-H.|last5=Lee|first5=Y.-W.|last6=Hwang|first6=I.|last7=Lee|first7=J.-S.|last8=Choi|first8=Y.-D.|date=2001-04-10|title=Jasmonic acid carboxyl methyltransferase: a key enzyme for jasmonate-regulated plant responses|journal=Proceedings of the National Academy of Sciences|volume=98|issue=8|pages=4788–4793|doi=10.1073/pnas.081557298|issn=0027-8424|pmid=11287667|pmc=31912|bibcode=2001PNAS...98.4788S|doi-access=free}} It can also be conjugated to amino acids in some biological contexts. Decarboxylation affords the related fragrance jasmone.
References
- {{cite book |editor1-first= Ushio|editor1-last= Sankawa|editor2-first= Derek H. R.|editor2-last= Barton|editor3-first= Koji|editor3-last= Nakanishi|editor4-first= Otto|editor4-last= Meth-Cohn|title= Comprehensive Natural Products Chemistry: Polyketides and Other Secondary Metabolites Including Fatty Acids and Their Derivatives|year= 1999|publisher= Pergamon Press|isbn= 978-0-08-043153-6}}
{{Plant_hormones}}
{{DEFAULTSORT:Jasmonic Acid}}