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Related Concept Videos

Peroxisomes01:24

Peroxisomes

Peroxisomes are specialized organelles present in fungi, plant, and animal cells. It can vary in number, size, morphology, and activity depending on the type of tissue and the nutritional state of the cell. For example, cells with active lipid metabolism, such as adipocytes, neurons, and hepatocytes, have more peroxisomes than other cells in the body. Besides their primary role in breaking down complex organic molecules, peroxisomes can also synthesize specific macromolecules and participate in...
Peroxisomes01:24

Peroxisomes

Peroxisomes are specialized organelles present in fungi, plant, and animal cells. It can vary in number, size, morphology, and activity depending on the type of tissue and the nutritional state of the cell. For example, cells with active lipid metabolism, such as adipocytes, neurons, and hepatocytes, have more peroxisomes than other cells in the body. Besides their primary role in breaking down complex organic molecules, peroxisomes can also synthesize specific macromolecules and participate in...
Acid-Catalyzed Ring-Opening of Epoxides02:24

Acid-Catalyzed Ring-Opening of Epoxides

Epoxides that are three-membered ring systems are more reactive than other cyclic and acyclic ethers. The high reactivity of epoxides originates from the strain present in the ring. This ring strain acts as a driving force for epoxides to undergo ring-opening reactions either with halogen acids or weak nucleophiles in the presence of mild acid. The acid catalyst converts the epoxide oxygen, a poor leaving group, into an oxonium ion, a better leaving group, making the reaction feasible. The...
Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids02:04

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Diols are compounds with two hydroxyl groups. In addition to syn dihydroxylation, diols can also be synthesized through the process of anti dihydroxylation. The process involves treating an alkene with a peroxycarboxylic acid to form an epoxide. Epoxides are highly strained three-membered rings with oxygen and two carbons occupying the corners of an equilateral triangle. This step is followed by ring-opening of the epoxide in the presence of an aqueous acid to give a trans diol.
Radical Autoxidation01:20

Radical Autoxidation

The oxidation of an organic compound in the presence of air or oxygen is called autoxidation. For example, cumene reacts with oxygen to form hydroperoxide. Autoxidation involves initiation, propagation, and termination steps. Many organic compounds are susceptible to autoxidation—especially ethers in the presence of oxygen, which form hydroperoxides. Even though this reaction is slow, old ether bottles contain small amounts of peroxide, which leads to laboratory explosions during ether...
Oxidation of Phenols to Quinones01:17

Oxidation of Phenols to Quinones

In the presence of oxidizing agents, phenols are oxidized to quinones. Quinones can be easily reduced back to phenols using mild reducing agents. The electron-donating hydroxyl group enhances the reactivity of the aromatic ring, enabling oxidation of the ring even in the absence of an α hydrogen.
o-hydroxy phenols are oxidized to o-quinones and p-hydroxy phenols to p-quinones. Such redox reactions involve the transfer of two electrons and two protons. The reversible redox property is crucial in...

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Reactive electrophilic oxylipins: pattern recognition and signalling.

Martin J Mueller1, Susanne Berger

  • 1Julius-von-Sachs-Institute for Biosciences, Pharm. Biology, Biocenter, University of Wuerzburg, Julius-von-Sachs-Platz 2, 97082 Wuerzburg, Germany. martin.mueller@biozentrum.uni-wuerzburg.de

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Reactive electrophilic oxylipins (RES) in plants, formed non-enzymatically, trigger defense and detoxification responses. These compounds, like reactive oxygen and nitrogen species (ROS/RNS), modify proteins, impacting plant signaling and gene expression.

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Area of Science:

  • Plant biochemistry
  • Molecular biology
  • Chemical ecology

Background:

  • Oxidized lipids, specifically reactive electrophilic oxylipins (RES), are present in plants.
  • These compounds can be formed through enzymatic and non-enzymatic pathways.
  • While toxic at high levels, RES exhibit biological activity at low concentrations.

Purpose of the Study:

  • To define reactive electrophilic oxylipins (RES) as a class of compounds.
  • To investigate the common biological activities and mechanisms of RES.
  • To compare the signaling roles of RES with reactive oxygen and nitrogen species (ROS/RNS).

Main Methods:

  • Meta-analysis of proteomic studies.
  • Transcriptome analysis.
  • Chemical property assessment (lipophilicity, thiol-reactivity).

Main Results:

  • RES, ROS, and RNS modify a similar set of redox-regulated proteins, often targets of thioredoxins.
  • Post-translational thiol-modification of these proteins alters their activity.
  • Transcriptome analysis shows overlapping but distinct gene induction patterns between RES and ROS.

Conclusions:

  • Thiol-reactivity is a key shared property enabling RES, ROS, and RNS to modulate protein function via thiol-modification.
  • RES play a significant role in plant signal transduction and gene regulation.
  • Structural properties beyond electrophilicity influence RES target selectivity and biological outcomes.