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International Journal of Molecular... Nov 2022For immobile plants, the main means of protection against adverse environmental factors is the biosynthesis of various secondary (specialized) metabolites. The extreme... (Review)
Review
For immobile plants, the main means of protection against adverse environmental factors is the biosynthesis of various secondary (specialized) metabolites. The extreme diversity and high biological activity of these metabolites determine the researchers' interest in plants as a source of therapeutic agents. Oxylipins, oxygenated derivatives of fatty acids, are particularly promising in this regard. Plant oxylipins, which are characterized by a diversity of chemical structures, can exert protective and therapeutic properties in animal cells. While the therapeutic potential of some classes of plant oxylipins, such as jasmonates and acetylenic oxylipins, has been analyzed thoroughly, other oxylipins are barely studied in this regard. Here, we present a comprehensive overview of the therapeutic potential of all major classes of plant oxylipins, including derivatives of acetylenic fatty acids, jasmonates, six- and nine-carbon aldehydes, oxy-, epoxy-, and hydroxy-derivatives of fatty acids, as well as spontaneously formed phytoprostanes and phytofurans. The presented analysis will provide an impetus for further research investigating the beneficial properties of these secondary metabolites and bringing them closer to practical applications.
Topics: Animals; Oxylipins; Cyclopentanes; Plants
PubMed: 36498955
DOI: 10.3390/ijms232314627 -
Redox Biology Oct 2020Oxylipins (compounds derived from the oxidation of polyunsaturated fatty acids) are essential in retrograde signaling emanating from plastids to the nucleus during plant... (Review)
Review
Oxylipins (compounds derived from the oxidation of polyunsaturated fatty acids) are essential in retrograde signaling emanating from plastids to the nucleus during plant developmental and stress responses. In this graphical review, we provide an overview of the chemical structure, biosynthesis and role of oxylipins, as both redox and hormonal signals, in controlling plant development and stress responses. We also briefly summarize current gaps in the understanding of the involvement of oxylipins in plastidial retrograde signaling to highlight future avenues for research.
Topics: Fatty Acids, Unsaturated; Oxylipins; Plants; Plastids; Signal Transduction
PubMed: 32979794
DOI: 10.1016/j.redox.2020.101717 -
Chembiochem : a European Journal of... Sep 2020Oxylipins constitute a family of oxidized fatty acids, that are well known as tissue hormones in mammals. They contribute to inflammation and its resolution. The major... (Review)
Review
Oxylipins constitute a family of oxidized fatty acids, that are well known as tissue hormones in mammals. They contribute to inflammation and its resolution. The major classes of these lipid mediators are inflammatory prostaglandins (PGs) and leukotrienes (LTs) as well as pro-resolving resolvins (Rvs). Understanding their biosynthetic pathways and modes of action is important for anti-inflammatory interventions. Besides mammals, marine algae also biosynthesize mammalian-like oxylipins and thus offer new opportunities for oxylipin research. They provide prolific sources for these compounds and offer unique opportunities to study alternative biosynthetic pathways to the well-known lipid mediators. Herein, we discuss recent findings on the biosynthesis of oxylipins in mammals and algae including an alternative pathway to prostaglandin E , a novel pathway to a precursor of leukotriene B , and the production of resolvins in algae. We evaluate the pharmacological potential of the algal metabolites with implications in health and disease.
Topics: Animals; Anti-Inflammatory Agents, Non-Steroidal; Humans; Inflammation; Leukotrienes; Molecular Structure; Oxylipins; Phaeophyceae; Prostaglandins
PubMed: 32239741
DOI: 10.1002/cbic.202000178 -
Toxins Nov 2021Fungal contamination of food, especially by mycotoxigenic fungi, not only reduces the quality of the food, but can also cause serious diseases, thus posing a major food... (Review)
Review
Fungal contamination of food, especially by mycotoxigenic fungi, not only reduces the quality of the food, but can also cause serious diseases, thus posing a major food safety challenge to humans. Apart from sound food control systems, there is also a continual need to explore antifungal agents that can inhibit fungal growth and mycotoxin production in food. Many types of fatty acids (FAs) and their oxidized derivatives, oxylipins, have been found to exhibit such effects. In this review, we provide an update on the most recent literature on the occurrence and formation of FAs and oxylipins in food, their effects on fungal growth and mycotoxin synthesis, as well as the genetic and molecular mechanisms of actions. Research gaps in the field and needs for further studies in order to realizing the potential of FAs and oxylipins as natural antifungal preservatives in food are also discussed.
Topics: Fatty Acids; Food Contamination; Food Microbiology; Food Preservation; Fungi; Fungicides, Industrial; Mycotoxins; Oxylipins
PubMed: 34941690
DOI: 10.3390/toxins13120852 -
Biochimie May 2017Oxylipins are bioactive metabolites derived from the oxygenation of ω3 and ω6 polyunsaturated fatty acids, triggered essentially by cyclooxygenase and lipoxygenase... (Review)
Review
Oxylipins are bioactive metabolites derived from the oxygenation of ω3 and ω6 polyunsaturated fatty acids, triggered essentially by cyclooxygenase and lipoxygenase activities. Oxylipins are involved in the development and function of adipose tissue and their productions are strictly related to diet quality and quantity. Oxylipins signal via cell surface membrane (G Protein-coupled receptors) and nuclear receptors (peroxisome proliferator-activated receptors), two pathways playing a pivotal role in adipocyte biology. In this review, we made an attempt to cover the available knowledge about synthesis and molecular function of oxylipins known to modulate adipogenesis, adipocyte function and phenotype conversion, with a focus on their interaction with peroxisome proliferator-activated nuclear receptor family.
Topics: Adipogenesis; Animals; Humans; Oxylipins; Peroxisome Proliferator-Activated Receptors; Receptors, G-Protein-Coupled
PubMed: 28034718
DOI: 10.1016/j.biochi.2016.12.012 -
International Journal of Molecular... Mar 2023α-linolenic acid (ALA) is an essential C-18 n-3 polyunsaturated fatty acid (PUFA), which can be elongated to longer n-3 PUFAs, such as eicosapentaenoic acid (EPA).... (Review)
Review
α-linolenic acid (ALA) is an essential C-18 n-3 polyunsaturated fatty acid (PUFA), which can be elongated to longer n-3 PUFAs, such as eicosapentaenoic acid (EPA). These long-chain n-3 PUFAs have anti-inflammatory and pro-resolution effects either directly or through their oxylipin metabolites. However, there is evidence that the conversion of ALA to the long-chain PUFAs is limited. On the other hand, there is evidence in humans that supplementation of ALA in the diet is associated with an improved lipid profile, a reduction in the inflammatory biomarker C-reactive protein (CRP) and a reduction in cardiovascular diseases (CVDs) and all-cause mortality. Studies investigating the cellular mechanism for these beneficial effects showed that ALA is metabolized to oxylipins through the Lipoxygenase (LOX), the Cyclooxygenase (COX) and the Cytochrome P450 (CYP450) pathways, leading to hydroperoxy-, epoxy-, mono- and dihydroxylated oxylipins. In several mouse and cell models, it has been shown that ALA and some of its oxylipins, including 9- and 13-hydroxy-octadecatrienoic acids (9-HOTrE and 13-HOTrE), have immunomodulating effects. Taken together, the current literature suggests a beneficial role for diets rich in ALA in human CVDs, however, it is not always clear whether the described effects are attributable to ALA, its oxylipins or other substances present in the supplemented diets.
Topics: Humans; Mice; Animals; Oxylipins; alpha-Linolenic Acid; Cardiovascular Diseases; Eicosapentaenoic Acid; Diet; Fatty Acids, Omega-3
PubMed: 37047085
DOI: 10.3390/ijms24076110 -
The FEBS Journal Apr 2011In nearly every living organism, metabolites derived from lipid peroxidation, the so-called oxylipins, are involved in regulating developmental processes as well as... (Review)
Review
In nearly every living organism, metabolites derived from lipid peroxidation, the so-called oxylipins, are involved in regulating developmental processes as well as environmental responses. Among these bioactive lipids, the mammalian and plant oxylipins are the best characterized, and much information about their physiological role and biosynthetic pathways has accumulated during recent years. Although the occurrence of oxylipins and enzymes involved in their biosynthesis has been studied for nearly three decades, knowledge about fungal oxylipins is still scarce as compared with the situation in plants and mammals. However, the research performed so far has shown that the structural diversity of oxylipins produced by fungi is high and, furthermore, that the enzymes involved in oxylipin metabolism are diverse and often exhibit unusual catalytic activities. The aim of this review is to present a synopsis of the oxylipins identified so far in fungi and the enzymes involved in their biosynthesis.
Topics: Animals; Fungal Proteins; Fungi; Host-Pathogen Interactions; Lipid Peroxidation; Molecular Structure; Oxylipins; Plants
PubMed: 21281447
DOI: 10.1111/j.1742-4658.2011.08027.x -
Cellular Microbiology Jun 2019Oxylipins, or oxygenated lipids, are universal signalling molecules across all kingdoms of life. These molecules, either produced by microbial pathogens or their... (Review)
Review
Oxylipins, or oxygenated lipids, are universal signalling molecules across all kingdoms of life. These molecules, either produced by microbial pathogens or their mammalian host, regulate inflammation during microbial infection. In this review, we summarise current literature on the biosynthesis pathways of microbial oxylipins and their biological activity towards mammalian cells. Collectively, these studies have illustrated how microbial pathogens can modulate immune rsponse and disease outcome via oxylipin-mediated mechanisms.
Topics: Animals; Bacteria; Bacterial Infections; Eicosanoids; Epoxide Hydrolases; Fungi; Humans; Inflammation; Lipoxygenases; Mycoses; Oxylipins; Phospholipases; Prostaglandin-Endoperoxide Synthases; Protozoan Infections; Thromboxane-A Synthase; Trypanosomatina
PubMed: 30866138
DOI: 10.1111/cmi.13025 -
Advances in Nutrition (Bethesda, Md.) Sep 2016Alzheimer disease (AD) is becoming one of the most prevalent neurodegenerative conditions worldwide. Although the disease progression is becoming better understood,... (Review)
Review
Alzheimer disease (AD) is becoming one of the most prevalent neurodegenerative conditions worldwide. Although the disease progression is becoming better understood, current medical interventions can only ameliorate some of the symptoms but cannot slow disease progression. Neuroinflammation plays an important role in the advancement of this disorder, and n-3 (ω-3) polyunsaturated fatty acids (PUFAs) are involved in both the reduction in and resolution of inflammation. These effects may be mediated by the anti-inflammatory and proresolving effects of bioactive lipid mediators (oxylipins) derived from n-3 PUFAs [eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA)] in fish oil. Although interventions have generally used fish oil containing both EPA and DHA, several studies that used either EPA or DHA alone or specific oxylipins derived from these fatty acids indicate that they have distinct effects. Both DHA and EPA can reduce neuroinflammation and cognitive decline, but EPA positively influences mood disorders, whereas DHA maintains normal brain structure. Fewer studies with a plant-derived n-3 PUFA, α-linolenic acid, suggest that other n-3 PUFAs and their oxylipins also may positively affect AD. Further research identifying the unique anti-inflammatory and proresolving properties of oxylipins from individual n-3 PUFAs will enable the discovery of novel disease-management strategies in AD.
Topics: Alzheimer Disease; Anti-Inflammatory Agents; Brain; Cognition Disorders; Docosahexaenoic Acids; Eicosapentaenoic Acid; Humans; Inflammation; Mood Disorders; Oxylipins; alpha-Linolenic Acid
PubMed: 27633106
DOI: 10.3945/an.116.012187 -
Plant Signaling & Behavior 2014The production of free oxylipins in plants is exquisitely controlled by cellular mechanisms that respond to environmental factors such as mechanical damage, insect...
The production of free oxylipins in plants is exquisitely controlled by cellular mechanisms that respond to environmental factors such as mechanical damage, insect herbivory and pathogen infection. One of the main targets of these cellular mechanisms are glycerolipases class A (GLA); acyl-hydrolyzing enzymes that upon their biochemical activation release unsaturated fatty acids or acylated oxylipins from glycerolipids. Recent studies performed in the wild tobacco species Nicotiana attenuata have started to reveal the complexity and specificity of GLA-regulated free oxylipin production. I present a model in which individual GLA lipases associate with individual lipoxygenases (LOX) in chloroplast membranes and envelope to define the initial committed steps of distinct oxylipin biosynthesis pathways. The unravelling of the mechanisms that activate GLAs and LOXs at the biochemical level and that control the interaction between these enzymes and their association with membranes will prove to be fundamental to understand how plants control free oxylipin biogenesis.
Topics: Chloroplasts; Lipase; Lipid Metabolism; Lipoxygenases; Models, Biological; Oxylipins; Plants
PubMed: 24603593
DOI: 10.4161/psb.28429