Methyl jasmonate

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Methyl jasmonate
Methyl jasmonate skeletal.svg
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 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 243-497-1
KEGG
PubChem CID
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 X mark.svgN
    Key: GEWDNTWNSAZUDX-WQMVXFAESA-N X mark.svgN
  • 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
C 13 H 20 O 3
Molar mass 224.3 g/mol
AppearanceColorless 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).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

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]

Contents

Description

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

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

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

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

Related Research Articles

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<span class="mw-page-title-main">Pinaceae</span> Family of conifers

The Pinaceae, or pine family, are conifer trees or shrubs, including many of the well-known conifers of commercial importance such as cedars, firs, hemlocks, piñons, larches, pines and spruces. The family is included in the order Pinales, formerly known as Coniferales. Pinaceae are supported as monophyletic by their protein-type sieve cell plastids, pattern of proembryogeny, and lack of bioflavonoids. They are the largest extant conifer family in species diversity, with between 220 and 250 species in 11 genera, and the second-largest in geographical range, found in most of the Northern Hemisphere, with the majority of the species in temperate climates, but ranging from subarctic to tropical. The family often forms the dominant component of boreal, coastal, and montane forests. One species, Pinus merkusii, grows just south of the equator in Southeast Asia. Major centres of diversity are found in the mountains of southwest China, Mexico, central Japan, and California.

<span class="mw-page-title-main">Jasmonate</span> Lipid-based plant hormones

Jasmonate (JA) and its derivatives are lipid-based plant hormones that regulate a wide range of processes in plants, ranging from growth and photosynthesis to reproductive development. In particular, JAs are critical for plant defense against herbivory and plant responses to poor environmental conditions and other kinds of abiotic and biotic challenges. Some JAs can also be released as volatile organic compounds (VOCs) to permit communication between plants in anticipation of mutual dangers.

<span class="mw-page-title-main">Phytoalexin</span> Class of chemical compounds

Phytoalexins are antimicrobial substances, some of which are antioxidative as well. They are defined, not by their having any particular chemical structure or character, but by the fact that they are defensively synthesized de novo by plants that produce the compounds rapidly at sites of pathogen infection. In general phytoalexins are broad spectrum inhibitors; they are chemically diverse, and different chemical classes of compounds are characteristic of particular plant taxa. Phytoalexins tend to fall into several chemical classes, including terpenoids, glycosteroids, and alkaloids; however the term applies to any phytochemicals that are induced by microbial infection.

<i>Phytoplasma</i> Genus of bacteria

Phytoplasmas are obligate intracellular parasites of plant phloem tissue and of the insect vectors that are involved in their plant-to-plant transmission. Phytoplasmas were discovered in 1967 by Japanese scientists who termed them mycoplasma-like organisms. Since their discovery, phytoplasmas have resisted all attempts at in vitro culture in any cell-free medium; routine cultivation in an artificial medium thus remains a major challenge. Phytoplasmas are characterized by the lack of a cell wall, a pleiomorphic or filamentous shape, a diameter normally less than 1 μm, and a very small genome.

<span class="mw-page-title-main">Jasmonic acid</span> Chemical compound

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.

<span class="mw-page-title-main">Plant defense against herbivory</span> Plants defenses against being eaten

Plant defense against herbivory or host-plant resistance (HPR) is a range of adaptations evolved by plants which improve their survival and reproduction by reducing the impact of herbivores. Plants can sense being touched, and they can use several strategies to defend against damage caused by herbivores. Many plants produce secondary metabolites, known as allelochemicals, that influence the behavior, growth, or survival of herbivores. These chemical defenses can act as repellents or toxins to herbivores or reduce plant digestibility. Another defensive strategy of plants is changing their attractiveness. To prevent overconsumption by large herbivores, plants alter their appearance by changing their size or quality, reducing the rate at which they are consumed.

<span class="mw-page-title-main">Systemin</span> Plant peptide hormone

Systemin is a plant peptide hormone involved in the wound response in the family Solanaceae. It was the first plant hormone that was proven to be a peptide having been isolated from tomato leaves in 1991 by a group led by Clarence A. Ryan. Since then, other peptides with similar functions have been identified in tomato and outside of the Solanaceae. Hydroxyproline-rich glycopeptides were found in tobacco in 2001 and AtPeps were found in Arabidopsis thaliana in 2006. Their precursors are found both in the cytoplasm and cell walls of plant cells, upon insect damage, the precursors are processed to produce one or more mature peptides. The receptor for systemin was first thought to be the same as the brassinolide receptor but this is now uncertain. The signal transduction processes that occur after the peptides bind are similar to the cytokine-mediated inflammatory immune response in animals. Early experiments showed that systemin travelled around the plant after insects had damaged the plant, activating systemic acquired resistance, now it is thought that it increases the production of jasmonic acid causing the same result. The main function of systemins is to coordinate defensive responses against insect herbivores but they also affect plant development. Systemin induces the production of protease inhibitors which protect against insect herbivores, other peptides activate defensins and modify root growth. They have also been shown to affect plants' responses to salt stress and UV radiation. AtPEPs have been shown to affect resistance against oomycetes and may allow A. thaliana to distinguish between different pathogens. In Nicotiana attenuata, some of the peptides have stopped being involved in defensive roles and instead affect flower morphology.

<span class="mw-page-title-main">Plant perception (physiology)</span> Plants interaction to environment

Plant perception is the ability of plants to sense and respond to the environment by adjusting their morphology and physiology. Botanical research has revealed that plants are capable of reacting to a broad range of stimuli, including chemicals, gravity, light, moisture, infections, temperature, oxygen and carbon dioxide concentrations, parasite infestation, disease, physical disruption, sound, and touch. The scientific study of plant perception is informed by numerous disciplines, such as plant physiology, ecology, and molecular biology.

<span class="mw-page-title-main">Myrosinase</span>

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<span class="mw-page-title-main">Leucyl aminopeptidase</span> Class of enzymes

Leucyl aminopeptidases are enzymes that preferentially catalyze the hydrolysis of leucine residues at the N-terminus of peptides and proteins. Other N-terminal residues can also be cleaved, however. LAPs have been found across superkingdoms. Identified LAPs include human LAP, bovine lens LAP, porcine LAP, Escherichia coli LAP, and the solanaceous-specific acidic LAP (LAP-A) in tomato.

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<span class="mw-page-title-main">Loline alkaloid</span> Class of chemical compounds

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Chemical defenses in <i>Cannabis</i>

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Calcium signaling in <i>Arabidopsis</i>

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References

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