Jasmonic acid methyl ester

Methyl jasmonate [1211-29-6], 3-oxo-2-(2-civ-pentenyl)cyclopentaneacetic acid methyl ester... 

The methyl ester of jasmonic acid (methyl 3-oxo-2-(2 -pentenyl)-cyclopentaneacetate) is also known as both an active plant hormone and an important fragrance and flavor component with sweet-floral and jasmine-like aroma notes (13). Methyl jasmonate induces plant systems to provide defense from microbial infection, and is a secondary synthesis product of plants. Methyl jasmonate was also isolated from the Oriental fruit moth, Grapholitha molesta as a part of the male sex hormone (7,75). The authors demonstrated that the volatile form of jasmonic acid, methyl jasmonate, is a major signal molecule for inter- and intra species communications. Methyl jasmonate is expected to have... 

Synonyms Cyclopentaneacetic acid, 3-oxo-2-(2-pentenyl)-, methyl ester Jasmoneige Methyl epi-jasmonate Methyl 2-pent-3-enyl-3-oxo-1-cyclopentyl acetate 3-Oxo-2-(2-pentenyl) cyclopentaneacetic acid, methyl ester 2-Pentenylcyclopentanone-3-acetic acid, methyl ester Empiricai C13H20O3... 

Oxo-2-(2-pentenyl) cyclopentaneacetic acid, methyl ester. See Methyl jasmonate... 

Thirty-six plant species tested in cell suspension culture could be elicited by exogenously supplied methyl jasmonate to accumulate secondary metabolites by a factor of 9 to 30 over the control values. Induction by MJ was not specific to any one type of secondary metabolite but rather general to a wide spectrum of low molecular weight substances ranging from flavonoids, guaianolides and anthraquinones to various classes of alkaloids [96]. Endogenous jasmonic acid and its methyl ester (MJ) accumulate rapidly and transiently after treatment of plant cell suspension cultures of Rauvolfia canescens and Eschscholtzia califor-nica with a yeast elicitor [97]. 

Small molecule carboxylates are an important class of compounds that plants produce to attract pollinators,44 defend against herbivory,45 7 regulate the cell cycle,48,49 and induce defense responses.50 5 Often these compounds are esterified and volatilized. Plants utilize the emission of volatile esters as chemoattractants and signaling molecules. Classes of volatile compounds include the salicylates and jasmonates, which are ubiquitously distributed in the plant kingdom. Jasmonic acid, salicylic acid, and their methyl ester derivatives, are intimately involved in cell regulation and help control such developmental processes as seed germination, flower development, fruit development, and senescence.14,17,53... 

Jasmonic acid (JA) (Fig. If) and its methyl ester, methyl jasmonate (MJa), occur in many plants [24], JA is formed from linoleic acid (18 3), the first step being catalyzed by... 

Jasmonic acid was first discovered as its methylester (2) an odoriferous compound from the essential oil of jasmine (Jasminum grandiflomm L.) [3], Early interest in this compound centered on its fragrant properties but recently, jasmonic acid and its methyl ester have fascinated plant physiologists and molecular biologists because they have been shown to possess hormonal activity [4], can act as a senescence-promoting substance [5], and can induce JIP (jasmonate induced proteins) [6] and soybean vegetative storage proteins [7],... 

In plants, responses to many biotic and abiotic stresses are, at least in part, mediated by the jasmonate family, including jasmonate (JA) and its methyl ester MeJA, which are synthesized via the octadecanoid pathway, beginning with phospholipase A to release linolenic acid from chloroplast membrane [27,28]. They play a central role in regulating the biosynthesis of many secondary metabolites, and induction of plant secondary metabolite accumulation by the JA family is not limited to certain types of metabolites in most plants [29], as shown in Table 17.1. 

Dosage/response experiments then showed that the biological activity resides mainly with the primary product, namely the (3H,7S)-jasmonic acid to a lesser extent with its methyl ester. Jasmonic acid does not bind as the free acid, but as a conjugate with isoleucine to the same receptor as coronatine, a phytotoxin produced by Pseudomonas syringae. In this conjugate, epimerisation at C-7, which is associated with a dramatic loss in activity, is used by the plants to regulate hormone activity. [82]... 

Jasmonic acid (JA) and its methyl ester (MJA) are important members of the family of natural jasmonates. Exogenously adding MJA was shown to increase the production of secondary metabolites in a variety of plant species. Some synthetic elicitors have also been proven to be too. We describe a series of synthetic cell culture elicitors in Chapter 4, including MJA derivatives and benzothiadiazole (BTH) derivatives. Some of them display more potent activity in Taxus chinensis cell culture and Panax notoginseng cell culture than MJA, which reflects the full application of chemical bioengineering in plant cell culture. 

Besides SA, jasmonic acid (JA) and its methyl ester are involved in ISR as signalling moleeules. JA and its methyl ester have been mainly considered as mediators of plant responses triggered by wounding and insect feeding, but their involvement in resistanee against pathogens has also been proven. For example, methyl jasmonate was used in parsley eell suspension cultures... 

Jasmonic acid (59) and its methyl ester are widespread among plants and have demonstrated growth-inhibit-... 

Crombie, L. and K. M. Mistry, Synthesis of 12-oxophytodienoic acid (12-oxoPDA) and the compounds of its enzymic degradation cascade in plants, OPC-8 0, -6 0, -4 0, and -2 0 epi-jasmonic acid), as their methyl esters, J. Chem. Soc. Perkin Trans. I, 1981-1991 (1991). 

The latter is the methyl ester of jasmonic acid, a plant hormone, and is a significant odor component of jasmine, as is jasmone (27), a product of degradation of jasmonic acid. 

Simko I, Omer EA, Ewing EE, McMurry S, Koch JL, Davies PJ (1996) Tuberonic (12-OH-jasmonic) acid glucoside and its methyl ester in potato. Phytochemistry 43 727-730 Singh AP, Singh AK, Begum AS, Sahai M (2003) Two acyl sucroses from Petunia nyctaginiflora. Phytochemistry 63 485-489... 

Formation of (+)-7-/60-jasmonic acid which is sequentially enzymatically converted to (-)-jasmonic acid JA and its methyl ester methyl jasmonate (MJ) [4], and also to other jasmonate compounds such as tuberonic acid, etc. 

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