Traumatic acid

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Traumatic acid [1]
Traumatic acid structure.png
Names
Preferred IUPAC name
(2E)-Dodec-2-enedioic acid
Other names
(E)-Dodec-2-enedioic acid
Dodec-2-enedioic acid
trans-Traumatic acid
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.026.382 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • InChI=1S/C12H20O4/c13-11(14)9-7-5-3-1-2-4-6-8-10-12(15)16/h7,9H,1-6,8,10H2,(H,13,14)(H,15,16)/b9-7+ X mark.svgN
    Key: MAZWDMBCPDUFDJ-VQHVLOKHSA-N X mark.svgN
  • O=C(O)/C=C/CCCCCCCCC(O)=O
Properties
C12H20O4
Molar mass 228.28
Melting point 166 to 167 °C (331 to 333 °F; 439 to 440 K)
Boiling point 150 to 160 °C (302 to 320 °F; 423 to 433 K)at 0.001 mmHg
Sparingly soluble
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Traumatic acid is a monounsaturated dicarboxylic acid that occurs naturally in plants. The compound was first isolated from wounded bean plants by American chemists James English Jr. and James Frederick Bonner and Dutch scientist Arie Jan Haagen-Smit in 1939. [2] Traumatic acid is a potent wound healing agent in plants ("wound hormone") that stimulates cell division near a trauma site to form a protective callus and to heal the damaged tissue. It may also act as a growth hormone, especially in inferior plants (e.g. algae). Traumatic acid is biosynthesized in plants by non-enzymatic oxidation of traumatin (12-oxo-trans-10-dodecenoic acid), another wound hormone.

At normal conditions, traumatic acid is a solid, crystalline, water-insoluble substance. The salts and esters of traumatic acid are called traumatates.

Traumatic acid is used as an intermediate in prostaglandin synthesis. It is also a constituent of some pharmaceutical products, such as the odontostomatologic gel Restomyl, due to its mucosal re-epithelialization activity.

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Salicylic acid Chemical compound

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Arginine Amino acid

Arginine, also known as l-arginine (symbol Arg or R), is an α-amino acid that is used in the biosynthesis of proteins. It contains an α-amino group, an α-carboxylic acid group, and a side chain consisting of a 3-carbon aliphatic straight chain ending in a guanidino group. At physiological pH, the carboxylic acid is deprotonated (−COO), the amino group is protonated (−NH3+), and the guanidino group is also protonated to give the guanidinium form (-C-(NH2)2+), making arginine a charged, aliphatic amino acid. It is the precursor for the biosynthesis of nitric oxide. It is encoded by the codons CGU, CGC, CGA, CGG, AGA, and AGG.

Steroid Any organic compound having sterane as a core structure

A steroid is a biologically active organic compound with four rings arranged in a specific molecular configuration. Steroids have two principal biological functions: as important components of cell membranes which alter membrane fluidity; and as signaling molecules. Hundreds of steroids are found in plants, animals and fungi. All steroids are manufactured in cells from the sterols lanosterol (opisthokonts) or cycloartenol (plants). Lanosterol and cycloartenol are derived from the cyclization of the triterpene squalene.

Acetyl-CoA Chemical compound

| C23H38N7O17P3S |- | Molar mass | 809.57 g·mol−1 |- | UV-vis (λmax) | 260 nm; 232 nm |- | Absorbance | ε260 = 16.4 mM−1 cm−1 (adenine)
ε232 = 8.7 mM−1 cm−1 (thioester)
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Methyl jasmonate Chemical compound

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Systemin

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.

Equilenin

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Traumatin is a plant hormone produced in response to wound. Traumatin is a precursor to the related hormone traumatic acid.

Octadecanoid pathway

The octadecanoid pathway is a biosynthetic pathway for the production of the phytohormone jasmonic acid (JA), an important hormone for induction of defense genes. JA is synthesized from alpha-linolenic acid, which can be released from the plasma membrane by certain lipase enzymes. For example, in the wound defense response, phospholipase C will cause the release of alpha-linolenic acid for JA synthesis.

Arie Jan Haagen-Smit was a Dutch chemist. He is best known for linking the smog in Southern California to automobiles and is therefore known by many as the "father" of air pollution control. After serving as an original board member of the Motor Vehicle Pollution Control Board, formed in 1960 to combat the smog, Dr. Haagen-Smit became the California Air Resources Board's first chairman in 1968. Shortly before his death, of lung cancer, the Air Resources Board's El Monte Laboratory was named after him.

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Plants have developed numerous methods to respond to, and to heal, wounds and injuries. Lacking the mobility and circulatory systems of animals, they face unique challenges in dealing with wounds; however, they also have the benefits of increased cell potency, and plastic growth, wherein they have no set form unlike animals. Wound response includes healing of wounds by creating callus and depositing molecules such as suberin, as well as activating predator and disease resistance.

References

  1. Merck Index, 11th Edition, 9493
  2. English J Jr., Bonner J, Haagen-Smit AJ: Structure and synthesis of a plant wound hormone. Science 90:329. (1939)