Methyl Jasmonate
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Methyl jasmonate (abbreviated MeJA) is a
volatile organic compound Volatile organic compounds (VOCs) are organic compounds that have a high vapor pressure at room temperature. They are common and exist in a variety of settings and products, not limited to Indoor mold, house mold, Upholstery, upholstered furnitur ...
used in plant defense and many diverse developmental pathways such as
seed germination Germination is the process by which an organism grows from a seed or spore. The term is applied to the sprouting of a seedling from a seed of an angiosperm or gymnosperm, the growth of a sporeling from a spore, such as the spores of fungi, ...
, root growth,
flowering Flowers, also known as blooms and blossoms, are the reproductive structures of flowering plants ( angiosperms). Typically, they are structured in four circular levels, called whorls, around the end of a stalk. These whorls include: calyx, m ...
,
fruit ripening Ripening is a process in fruits that causes them to become more palatable. In general, fruit becomes Sweetness, sweeter, less green, and softer as it ripens. Even though the acidity of fruit increases as it ripens, the higher acidity level does no ...
, and
senescence Senescence () or biological aging is the gradual deterioration of Function (biology), functional characteristics in living organisms. Whole organism senescence involves an increase in mortality rate, death rates or a decrease in fecundity with ...
. Methyl jasmonate is derived from
jasmonic acid 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 ...
and the reaction is catalyzed by ''S''-adenosyl--methionine:jasmonic acid carboxyl methyltransferase.


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 The cytoplasm describes all the material within a eukaryotic or prokaryotic cell, enclosed by the cell membrane, including the organelles and excluding the nucleus in eukaryotic cells. The material inside the nucleus of a eukaryotic cell a ...
. An herbivorous attack on a plant causes it to produce MeJA both for internal defense and for a signaling compound to other plants.


Defense chemicals

MeJA can induce the plant to produce multiple different types of defense chemicals such as
phytoalexin 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 ...
s (antimicrobial),
nicotine Nicotine is a natural product, naturally produced alkaloid in the nightshade family of plants (most predominantly in tobacco and ''Duboisia hopwoodii'') and is widely used recreational drug use, recreationally as a stimulant and anxiolytic. As ...
or
protease inhibitors Protease inhibitors (PIs) are medications that act by interfering with protease, enzymes that cleave proteins. Some of the most well known are antiviral drugs widely used to treat HIV/AIDS, hepatitis C and COVID-19. These protease inhibitors pre ...
. 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 Resin canals or resin ducts are elongated, tube-shaped intercellular spaces surrounded by epithelial cells which secrete resin into the canal. These canals are orientated longitudinally and radially in between fusiform rays. They are usually fou ...
production in
Norway spruce ''Picea abies'', the Norway spruce or European spruce, is a species of spruce native to Northern, Central and Eastern Europe. It has branchlets that typically hang downwards, and the largest cones of any spruce, 9–17 cm long. It is very clo ...
trees. This can be used as a defense against many insect attackers as a type of vaccine.


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 ''Picea abies'', the Norway spruce or European spruce, is a species of spruce native to Northern, Central and Eastern Europe. It has branchlets that typically hang downwards, and the largest cones of any spruce, 9–17 cm long. It is very clo ...
), the accumulation of
monoterpene Monoterpenes are a class of terpenes that consist of two isoprene units and have the molecular formula C10H16. Monoterpenes may be linear (acyclic) or contain rings (monocyclic and bicyclic). Modified terpenes, such as those containing oxygen func ...
and
sesquiterpene Sesquiterpenes are a class of terpenes that consist of three isoprene units and often have the molecular formula C15H24. Like monoterpenes, sesquiterpenes may be cyclic or contain rings, including many combinations. Biochemical modifications s ...
compounds doubled in the spruce needle tissues, a response that normally is only triggered when the tissue is damaged. In an experiment testing the effect of methyl jasmonate treatments on drought tolerance,
strawberry The garden strawberry (or simply strawberry; ''Fragaria × ananassa'') is a widely grown Hybrid (biology), hybrid plant cultivated worldwide for its fruit. The genus ''Fragaria'', the strawberries, is in the rose family, Rosaceae. The fruit ...
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. External application of methyl jasmonate has also shown a propensity for inducing an increased resistance to insect herbivory in some agricultural crops, such as
brassica ''Brassica'' () is a genus of plants in the cabbage and mustard family (Brassicaceae). The members of the genus are informally known as cruciferous vegetables, cabbages, mustard plants, or simply brassicas. Crops from this genus are sometim ...
s and
tobacco Tobacco is the common name of several plants in the genus '' Nicotiana'' of the family Solanaceae, and the general term for any product prepared from the cured leaves of these plants. More than 70 species of tobacco are known, but the ...
. 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. 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 An antibiotic is a type of antimicrobial substance active against bacteria. It is the most important type of antibacterial agent for fighting bacterial infections, and antibiotic medications are widely used in the treatment and prevention ...
effect is thought to be because of methyl jasmonate inducing resistance. MeJA is also a plant hormone involved in
tendril In botany, a tendril is a specialized Plant stem, stem, leaf or Petiole (botany), petiole with a thread-like shape used by climbing plants for support and attachment, as well as cellular invasion by parasitic plants such as ''Cuscuta''. There ar ...
(root) coiling, flowering, seed and fruit maturation. An increase of the hormone affects flowering time, flower morphology and the number of open flowers. MeJA induces ethylene-forming enzyme activity, which increases the amount of ethylene to the amount necessary for fruit maturation. Increased amounts of methyl jasmonate in plant roots have shown to inhibit their growth. It is predicted that the higher amounts of MeJA activate previously unexpressed genes within the roots to cause the growth inhibition.


Cancer cells

Methyl jasmonate induces cytochrome C release in the
mitochondria A mitochondrion () is an organelle found in the cells of most eukaryotes, such as animals, plants and fungi. Mitochondria have a double membrane structure and use aerobic respiration to generate adenosine triphosphate (ATP), which is us ...
of cancer cells, leading to
cell death Cell death is the event of a biological cell ceasing to carry out its functions. This may be the result of the natural process of old cells dying and being replaced by new ones, as in programmed cell death, or may result from factors such as di ...
, 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.


See also

*
Jasmonate 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 herb ...
* Methyl dihydrojasmonate


References


External links


General information about methyl jasmonate


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. ; published online 19 September 2005 {{DEFAULTSORT:Methyl Jasmonate Acetate esters Plant hormones Ketones Alkene derivatives Methyl esters