Oxylipins constitute a family of oxygenated natural products which are formed from fatty acids by pathways involving at least one step of dioxygen-dependent oxidation.[1] These small polar lipid compounds are metabolites of polyunsaturated fatty acids (PUFAs) including omega-3 fatty acids and omega-6 fatty acids. [2][3] Oxylipins are formed by enyzmatic or non-enzymatic oxidation of PUFAs. [2]
In animal species, four main pathways of oxylipin production prevail: lipoxygenases (LOXs) pathway, cyklooxygenases (COXs) route, cytochrome P450 (CYPs) pathway, and reactive oxygen species (ROS) route. [4] These pathways result in formation of many different oxylipin molecules which are important for number of processes in living organisms. The processes include inflamation, blood flow, energy metabolism, cellular life, cell signaling, or muscle contractions. [2][3][4] Oxylipins have both pro- and anti-inflamatory roles. [5]
Oxylipins are widespread in aerobic organisms including plants, animals and fungi. Many of oxylipins have physiological significance.[6][7] Typically, oxylipins are not stored in tissues but are formed on demand by liberation of precursor fatty acids from esterified forms.
^Wasternack C (October 2007). "Jasmonates: an update on biosynthesis, signal transduction and action in plant stress response, growth and development". Annals of Botany. 100 (4): 681–697. doi:10.1093/aob/mcm079. PMC 2749622. PMID 17513307.
^ abcCamunas-Alberca SM, Moran-Garrido M, Sáiz J, Villaseñor A, Taha AY, Barbas C (July 2023). "The role of oxylipins and their validation as biomarkers in the clinical context". TrAC Trends in Analytical Chemistry. 164: 117065. doi:10.1016/j.trac.2023.117065.
^ abWatrous JD, Niiranen TJ, Lagerborg KA, Henglin M, Xu YJ, Rong J, et al. (March 2019). "Directed Non-targeted Mass Spectrometry and Chemical Networking for Discovery of Eicosanoids and Related Oxylipins". Cell Chemical Biology. 26 (3): 433–442.e4. doi:10.1016/j.chembiol.2018.11.015. PMC 6636917. PMID 30661990.
^ abLiang N, Harsch BA, Zhou S, Borkowska A, Shearer GC, Kaddurah-Daouk R, et al. (January 2024). "Oxylipin transport by lipoprotein particles and its functional implications for cardiometabolic and neurological disorders". Progress in Lipid Research. 93: 101265. doi:10.1016/j.plipres.2023.101265. PMID 37979798.
^Wolfer AM, Gaudin M, Taylor-Robinson SD, Holmes E, Nicholson JK (December 2015). "Development and Validation of a High-Throughput Ultrahigh-Performance Liquid Chromatography-Mass Spectrometry Approach for Screening of Oxylipins and Their Precursors". Analytical Chemistry. 87 (23): 11721–11731. doi:10.1021/acs.analchem.5b02794. PMID 26501362.
^Zhao J, Davis LC, Verpoorte R (June 2005). "Elicitor signal transduction leading to production of plant secondary metabolites". Biotechnology Advances. 23 (4): 283–333. doi:10.1016/j.biotechadv.2005.01.003. PMID 15848039.
^Bolwell GP, Bindschedler LV, Blee KA, Butt VS, Davies DR, Gardner SL, et al. (May 2002). "The apoplastic oxidative burst in response to biotic stress in plants: a three-component system". Journal of Experimental Botany. 53 (372): 1367–1376. doi:10.1093/jexbot/53.372.1367. PMID 11997382.
Oxylipins constitute a family of oxygenated natural products which are formed from fatty acids by pathways involving at least one step of dioxygen-dependent...
Li SS, Liu QB, Zhang YY, Shi SC, Guo R, Yao GD, et al. (June 2020). "Oxylipin vanillyl acetals from Solanum lyratum". Fitoterapia. 143 (1): 104559. doi:10...
compounds. One such class is the oxidized fatty acid derivatives called oxylipins. Members of this family have been found to have anti-cancer, anti-bacterial...
For example, in chronic inflammatory cicatrizing conjunctivitis, active oxylipins, lysophospholipids, fatty acids, and endocannabinoids alterations, from...
out in series of mechanisms; oxidative burst, systematic resistance, the oxylipin pathway, and accumulation of sesquiterpenoid (Martinez et al., 2000). The...
a sub-category of oxylipins, i.e. oxidized fatty acids of diverse carbon units in length, and are distinguished from other oxylipins by their overwhelming...
formed through synthesis and oxygenation of enzymes. Active lipids in the oxylipin family derive from the synthesis of Cyclooxygenase or Prostaglandins. The...
Jane; Mikami, Yuzuru; Kobayashi, Jun'Ichi (2003). "Plakevulin A, a new oxylipin inhibiting DNA polymerases α and γ from sponge Plakortis species". Tetrahedron...
Gouveia-Figueira S, Domellöf M, Zivkovic AM, Nording ML (January 2016). "Oxylipins, endocannabinoids, and related compounds in human milk: Levels and effects...
675–685. doi:10.1002/hlca.19620450233. Browse J (2005). "Jasmonate: an oxylipin signal with many roles in plants". Plant Hormones. Vitamins & Hormones...
secondary metabolites that are synthesized by algae such as terpenoids, oxylipins, phlorotannins, volatile hydrocarbons, and products of mixed biogenetic...
Gouveia-Figueira S, Domellöf M, Zivkovic AM, Nording ML (January 2016). "Oxylipins, endocannabinoids, and related compounds in human milk: Levels and effects...
Monirujjaman M, Aukema HM (2015). "Advances in Our Understanding of Oxylipins Derived from Dietary PUFAs". Advances in Nutrition. 6 (5): 513–40. doi:10...
Luo X, Li F, Hong J, Lee CO, Sim CJ, Im KS, et al. (2006). "Cytotoxic oxylipins from a marine sponge Topsentia sp". J Nat Prod. 69 (4): 567–71. doi:10...
Wasternack and Hause 2013, and Wasternack and Song 2017. Jasmonates (JA) are oxylipins, i.e. derivatives of oxygenated fatty acid. They are biosynthesized from...
1016/S0168-9525(03)00138-0. PMID 12850447. Christie, William W. (22 May 2014). "Plant oxylipins: Chemistry and biology". Archived from the original on 30 June 2015. Retrieved...
octadienal, octatrienal, and decatrienal. Polyunsaturated aldehydes are oxylipins that are formed from lipids (specifically the fatty acid portion of lipids)...
(18 September 2008). "Structural insights into the evolutionary paths of oxylipin biosynthetic enzymes". Nature. 455 (7211): 363–8. Bibcode:2008Natur.455...
felt it had a strong sour taste. The fruit body of T. floccosus produces oxylipin (lipids generated by oxygenation of fatty acids) that are active against...
tuberosum L.) induce differential changes in volatile compound release and oxylipin synthesis. J. Exp. Bot. 60, 1231–1240 (2009). Wenke, K., Kai, M. & Piechulla...
"Catalysis-Based and Protecting-Group-Free Total Syntheses of the Marine Oxylipins Hybridalactone and the Ecklonialactones A, B, and C". J. Am. Chem. Soc...
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