Methyl Jasmonate

C13H20O3

Methyl Jasmonate (MeJA) is a substance used in plant defense.

 

Plants produce jasmonic acid and Methyl Jasmonate in response to many biotic and abiotic stresses (particularly herbivory and wounding), which build up in the damaged parts of the plant.

 

Jasmonates act as signalling compounds for the production of phytoalexins. 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.

 

Phytoalexins, once ingested by the attacker (e.g., insect), can be toxic or interfere with its digestion and may deter the attacker from further feeding. The jasmonate signal often spreads systemically throughout the plant and is a major component of systemic acquired resistance.

MeJA is also a plant hormone involved in tendril (root) coiling and seed maturation.

 

Where is Methyl Jasmonate found?

Methyl Jasmonate occurs widely in plants. Its biosynthesis starts with linolenic acid and proceeds through a number of stages involving lipoxidation, cyclisation and b-oxidation.1

 

What is the purpose of Methyl Jasmonate?

Plants that come under attack by insects or damaged mechanically produce higher levels of jasmonic acid and Methyl Jasmonate, which build up in the damaged parts of the plant. A model has been proposed in which wounding and systemin activate a lipase enzyme in receptor cell membranes resulting in the release of linolenic acid (the precursor of jasmonic acid) and activation of proteinase inhibitor genes. If ingested by the insect, the proteinase inhibitors can interfere with its digestive system and deter the insect from feeding. An 18-amino acid peptide called systemin (Ala-Val-Gln-Ser-Lys-Pro-Pro-Ser-Lys-Arg-Asp-Pro-Pro-Lys-Met-Gln-Thr-Asp) is the polypeptide wound signalling molecule.2

 

Jasmine

Methyl Jasmonate is one of the main odour components of jasmine (right), along with a related molecule called Jasmone. Methyl Jasmonate (MeJA) makes up some 2-3% of jasmine oil. 10,000 blossoms are needed to give 1 gram of the oil (10-4 g per blossom). Methyl Jasmonate is also a flavour ingredient of semi-black (oolong) and black tea. It is an expensive odour; commercial applications in detergents containing oxidising bleaches use the less reactive reduced dihydro- compounds. But there's much more to Methyl Jasmonate than a pretty smell.3

 

Jasminum auriculatum at Talakona forest, in Chittoor District of Andhra Pradesh, India

Jasmine or Jessamine (Jasminum) (from Arabic and Persian Yasmine, i.e. "gift from God", via Arabic) is a genus of shrubs and vines in the olive family (Oleaceae), with about 200 species, native to tropical and warm temperate regions of the Old World. The majority of species grow as climbers on other plants or on structures such as chicken wire, gates or fences. The leaves can be either evergreen (green all year round) or deciduous (falling leaves in autumn).

 

Jasminum auriculatum at Talakona forest, in Chittoor District of Andhra Pradesh, India

Cultivation of Jasmine

Jasmine is widely cultivated for its flowers, enjoyed in the garden, as house plants, and as cut flowers. The flowers are worn by women in their hair in southern and southeast Asia. Many species also yield an absolute, which is used in the production of perfumes and incense.

 

Consumption of Jasmine in China

Jasmine tisane is consumed in China, where it is called Jasmine flower tea (茉莉花茶; pinyin: m l huā ch). At Perumalpattu, Tiruvallur (TamilNadu).This large variety has a drawback that the plant produces less flowers all year round. The flower is pretty large, but commercially not viable since less flowers are produced.Jasminum sambac flowers are also used to make tea, which often has a base of green tea, but sometimes an Oolong base is used. The delicate Jasmine flower opens only at night during the full moon and is plucked in the morning when the tiny petals are tightly closed. They are then stored in a cool place until night. Between six and eight in the evening, as the temperature cools, the petals begin to open. Flowers and tea are "mated" in machines that control temperature and humidity. It takes four hours or so for the tea to absorb the fragrance and flavour of the Jasminum sambac flowers harvested for Malligai - Raama BaanamJasmine blossoms, and for the highest grades, this process may be repeated as many as seven times. Because the tea has absorbed moisture from the flowers, it must be refired to prevent spoilage. The spent flowers may or may not be removed from the final product, as the flowers are completely dry and contain no aroma. Giant fans are used to blow away and remove the petals from the denser tea leaves. If present, they simply add visual appeal and are no indication of the quality of the tea.

 

Jasmonates

 

The Jasmonates (JAs) are a group of plant hormones which help regulate plant growth and development. Jasmonates include jasmonic acid and its esters, such as methyl jasmonate (Methyl Jasmonate). Like the related prostaglandin hormones found in mammals, the Jasmonates are cyclopentanone derivatives which are derived biosynthetically from fatty acids. They are biosynthesized from linolenic acid by the octadecanoid pathway.

The level of Jasmonate in plants varies as a function of tissue and cell type, developmental stage, and in response to several different environmental stimuli. High levels of Jasmonate are also found in flowers and pericarp tissues of developing reproductive structures and in the chloroplasts of illuminated plants; Jasmonate levels also increase rapidly in response to mechanical perturbations such as tendril coiling and when plants suffer wounding.

Demonstrated roles of Jasmonate in planta include:

  • Jasmonate and Methyl Jasmonate inhibit the germination of nondormant seeds and stimulate the germination of dormant seeds

  • High levels of Jasmonate encourage the accumulation of storage proteins; genes encoding vegetative storage proteins are Jasmonate responsive and tuberonic acid (a Jasmonate derivative) has been proposed to play a role in the formation of tubers

  • Jasmonate application can induce chlorosis and inhibition of genes encoding proteins involved in photosynthesis, although the purpose of this response is unknown it is proposed that this response to Jasmonate could help reduce the plant's capacity for carbon assimilation under conditions of excess light or carbon

  • The role of Jasmonate accumulation in flowers and fruit is unknown; however, it may be related to fruit ripening (via ethylene), fruit carotenoid composition, and expression of genes encoding seed and vegetative storage proteins

  • Jasmonate plays a role in insect and disease resistance. Many genes during plant defense are induced by Jasmonate; Jasmonate and ethylene may act together in defense response

The perception of jasmonate is via the ubiquitin system, like auxins. After the conjugation of jasmonate and an amino acid isoleucine, it led to the SCFCOI1 complex degrade the ubiquitin markerd JAZ protein, and then releasing the transcription of other transcription factors.

Methyl Jasmonate

Methyl Jasmonate Molecule Animation

IUPAC name

Methyl (1R,2R)-3-Oxo-2-(2Z)-2-
pentenyl-cyclopentaneacetate

Other names

Methyl Jasmonate

Identifiers

CAS number

39924-52-2

SMILES

O=C1[C@H](C/C=C\CC) [C@@H](CC(OC)=O)CC1

Properties

Molecular formula

C13H20O3

Molar mass

224.3 g/mol

Appearance

Colorless liquid

Melting point

<25 C

Boiling point

88-90 C at 0.1 mmHg

Except where noted otherwise, data are given for materials in their standard state
(at 25 C, 100 kPa)

 

Jasmine

Jasminum sambac

Scientific classification

Kingdom:

Plantae

(unranked):

Angiosperms

(unranked):

Eudicots

(unranked):

Asterids

Order:

Lamiales

Family:

Oleaceae

Tribe:

Jasmineae

Genus:

Jasminum
L. (1753)

Type species

Jasminum officinale L.
 

Species

More than 200 species


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