Dokosanoidit ja niiden yleiskartta

Wikipediasta löydän tosiaan paljon dokosanoideista. Ensimmäisen kerran luin sellaisestakin rasvahappojohdannaisesta kuin resolviinit ja maresiinit suomalaisesta lähteestä Tohtori Tolonen ja  pidin aluksi  vähän epätodellisena, mutta aloin penkoa näitä karttoja esiin varmuuden vuoksi ja tulee molekyyliä kuin turkin hihasta ja kokonainen dokosanoidien uusi kartta vähitellen esiin. Nimittäin niiden  maineella jo  myydään valmisteita ja  kehutaan vaikutuksia.  Täytyy katsoa, voisivatko  ne  olla olemassa.  Sen lisäksi, että kaikista voi piirtää  oletettuja  kaavoja, pitää löytää myös artikkeleita joissa niitä tieteellisesti osoitetaan ja niiden oma vaikutus jollain tavalla voidaan erottaa muun  rasvakimpun vaikutuksista.  Siis nyt vain koetan hahmottaa karttaa.  Suomennan myös  tekstiä samalla ( välillä  vain omaan vihkooni)

Wikipediasta:
 Biokemiassa dokosanoidit ovat signaloinneissa vaikuttavia molekyylejä ja rakenteeltaan ne ovat 22 hiiltä sisältäviä rasvahappoja. Docosa tarkoittaa 22.  Ne ovat ensin tunnettu essentielleihin  rasvahappohin (EFA)  kuuluvasta  pitkästä omega3- rasvahaposta DHA, dokosahexaeenihappo.  Nimessä on hexa- sen takia että niissä  on 6 kaksoissidosta (hexa= 6).  Kaksoissidoksen paikat voidaan merkata Z kirjaimella  Esim. 4Z, 7Z, 10Z, 13Z, 16Z,19Z-dokosahexaeenihappo.  Z ei määritä  onko kyseessä R vai S isomeria.  Tästä  DHA-haposta voi tulla erilaisia dokosanoideja entsyymeillä (lipoxygenaasilla  LOX, syklo-oxygenaasilla  COX ja  sytokromi P450- entsyymeillä)

13. From Wikipedia, the free encyclopedia
    In biochemistry, docosanoids are signaling molecules made by the metabolism of twenty-two-carbon fatty acids (EFAs), especially the omega-3 fatty acid, Docosahexaenoic acid (DHA) (i.e. 4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoic acid) by lipoxygenase, cyclooxygenase, and cytochrome P450 enzymes.
    
    Muista dokosanoideista  ( 22 hiilen PUFA- rasvahapoista):
     Omega 6 -sarjassa on pidentynyt (elongoitunut)  AA: Sen nimeksi voi asettaa
    DTA, dokosatetraeenihappo  ( 4 kaksoissidosta,7Z,10Z,13Z,16Z-dokosatetraeenihappo , adreenihappo)
    Jos  DTA lisäksi desaturoituu, tulee myös omega6- sarjasta DHA, dokosahexaeenihappolaji.
    
    Omega-3 sarjassa on   pidentynyt EPA ja sen nnimeksi voi laittaa   DPA  dokosapentaeenihappo ( viisi kaksoissidosta) (i.e. 7Z,10Z,13Z,16Z,19Z-dokosapentaeenihappo. Tämän pidentymä (+2C) tekee  tunnetun DHA hapon  omega3 sarjassa. 
    
     Sekä omega3 että omega 6-linjojen  dokosahexaeenihapoista  tulee vaikuttavia  välittäjäaineita , proresolviinien  luokka,   "proresolvin mediator class of  PUFA metabolites", sanotaan Wikipediassa) Tästä on lähdeartikkelia  linkissä ( specialized proresolving mediators).
    

     Tämä Wikipedia-artikkeli sisältää  huomattavista dokosanoideista tekstiä.  Asetan sen tällaisenaan  sitaatiksi nyt aluksi suomentamatta ja tarkistamatta vielä.  Se on netistä suoraan.
    
    Contents
    • 1 Prominent docosanoids
      • 1.1 Specialized proresolving mediator docosanoids
      • 1.2 Neurofuran docosanoids
      • 1.3 Hydroxy-docosanoids
      • 1.4 Oxo-docosanoids
      • 1.5 DTA-derived docosanoids
    • 2 References

    Prominent docosanoids

    Specialized proresolving mediator docosanoids

    Potently bioactive agents of the specialized proresolving mediator class include:
    
    • DHA-derived Resolvins (Rv's) of the D series: RvD1, RvD2, RvD3, RvD4, RvD5, RvD6, AT-RvD1, AT-RvD2, AT-RvD3, AT-RvD4, AT-RvD5, and AT-RvD6 (see specialized proresolving mediators#DHA-derived Resolvins).
    • n-3 DPA-derived Rvs of the D series (RvD1_n-3, RvD2_n-3, and RvDD1_n-3) and the T series (RvT1, TvT2, RvT3, and RvT4) (see specialized proresolving mediators#n-3 DPA-derived resolvins).
    • DHA-derived Neuroprotectins, also termed protectins: PD1, PDX, 17-epi PD1, and 10-epi-DHA1 (see specialized proresolving mediators#DHA-derived protectins/neuroprotectins).
    • n-3 DPA derived protectins: RD1_n-3 and RvD1_n-3 (see specialized proresolving mediators#n-3 DPA-derived resolvins)(see DPA-derived protectins/neuroprotectins.
    • DHA derived Maresins: MaR1, MaR2, 7-epi-Mar1, Mar-L1, and Mar-L2 (see specialized proresolving mediators#DHA-derived Maresins).
    • n-3 DPA-derived maresins: Mar1_n-3, Mar2_n-3, and Mar3_n-3 (see specialized proresolving mediators#n-3 DPA-derived maresins).
    These DHA metabolites possess anti-inflammation and tissue-protection activities in animal models of inflammatory diseases; they are proposed to inhibit innate immune responses and thereby to protect from and to resolve a wide range of inflammatory responses in animals and humans. These metabolites are also proposed to contribute to the anti-inflammatory and other beneficial effects of dietary omega-3 fatty acids by being metabolized to them.^[1][2][3][4]
    

    Neurofuran docosanoids

    DHA can be converted non-enzymatically by free radical-mediated peroxidation to 8 different neurofuran regioisomers termed neuroprostanes and neurofuranes including 4-, 7-, 10-, 11-, 13-, 14-, 17-, and 20-series neurofurans/neuroporstanes for a total of 128 different racemic compounds. The most studied DHA-derived of these products are members of the 4-series, neurofuran 4-F_αneuroprostane and 4(RS)-ST-Δ6-8-neurofurane. These metabolites have been used mainly as biomarkers of oxidative stress that are formed in nerve tissues of the central nervous system.^[5][6]
    

    Hydroxy-docosanoids (HpDHAs, HDHAs )

    Cells metabolize DHA to 17S-hydroperoxy-4Z,7Z,10Z,13Z,15E,19Z-docahexaenoicacid acid (17-HpDHA) and then rapidly reduce this hydroperoxide to 17S-hydroxy-4Z,7Z,10Z,13Z,15E,19Z-docahexaenoicacid acid (17-HDHA) and similarly metabolize DHA to 13S-hydroperoxy-4Z,7Z,10Z,14Z,16Z,19Z-docahexaenoic acid (13-HpDHA) and then to 13S-hydroxy-4Z,7Z,10Z,14Z,16Z,19Z-docahexaenoicacid acid (13-HDHA). 17-HDHA exhibits potent in vitro as well as in vivo (animal model) anti-inflammatory activity while 17-HpDHA and to a lesser extent 17-HDHA inhibit the growth of cultured human breast cancer cells.^[7][8] Other SPM docosanoids, e.g. RvD1 and RvD2, have anti-growth effects against cancer cells in animal models.^[9]
    

    Oxo-docosanoids  (EFOXD6s)

    Cells can metabolize DHA to products that possess an oxo (i.e. ketone) residue. These products include 13-oxo-DHA (termed EFOXD6) and 17-oxo-DHA (termed 18-EFOXD6). Both oxo metabolites possess anti-inflammatory activity as assesses in in vitro systems (see Specialized proresolving mediators#Oxo-DHA and oxo-DPA metabolites).^[10]
    

    DTA-derived docosanoids (DH-EETs)

    Cyclooxygenase and Cytochrome P450 oxidase act upon Docosatetraenoic acid to produce dihomoprostaglandins^[11] and dihomo-epoxyeicosatrienoic acids^[12] and dihomo-EETs.^[13]
    

    References

    Oily fish are a rich source of the DHA from which Docosanoids derive
14. Calder PC (2015). "Marine omega-3 fatty acids and inflammatory processes: Effects, mechanisms and clinical relevance". Biochimica et Biophysica Acta. 1851 (4): 469–84. doi:10.1016/j.bbalip.2014.08.010. PMID 25149823.
15. Serhan CN, Chiang N, Dalli J, Levy BD (2015). "Lipid mediators in the resolution of inflammation". Cold Spring Harbor Perspectives in Biology. 7 (2): a016311. doi:10.1101/cshperspect.a016311. PMID 25359497.
16. Barden AE, Mas E, Mori TA (2016). "n-3 Fatty acid supplementation and proresolving mediators of inflammation". Current Opinion in Lipidology. 27 (1): 26–32. doi:10.1097/MOL.0000000000000262. PMID 26655290.
17. Balas L, Durand T (2016). "Dihydroxylated E,E,Z-docosatrienes. An overview of their synthesis and biological significance". Progress in Lipid Research. 61: 1–18. doi:10.1016/j.plipres.2015.10.002. PMID 26545300.
18. Arneson KO, Roberts LJ (2007). "Measurement of products of docosahexaenoic acid peroxidation, neuroprostanes, and neurofurans". Methods in Enzymology. 433: 127–43. doi:10.1016/S0076-6879(07)33007-3. PMID 17954232.
19. Leung KS, Galano JM, Durand T, Lee JC (2015). "Current development in non-enzymatic lipid peroxidation products, isoprostanoids and isofuranoids, in novel biological samples". Free Radical Research. 49 (7): 816–26. doi:10.3109/10715762.2014.960867. PMID 25184341.
20. Chiu CY, Gomolka B, Dierkes C, Huang NR, Schroeder M, Purschke M, Manstein D, Dangi B, Weylandt KH (2012). "Omega-6 docosapentaenoic acid-derived resolvins and 17-hydroxydocosahexaenoic acid modulate macrophage function and alleviate experimental colitis". Inflammation Research. 61 (9): 967–76. doi:10.1007/s00011-012-0489-8. PMID 22618200.
21. O'Flaherty JT, Hu Y, Wooten RE, Horita DA, Samuel MP, Thomas MJ, Sun H, Edwards IJ (2012). "15-lipoxygenase metabolites of docosahexaenoic acid inhibit prostate cancer cell proliferation and survival". PLOS ONE. 7 (9): e45480. doi:10.1371/journal.pone.0045480. PMC 3447860 . PMID 23029040.
22. Serhan CN, Chiang N, Dalli J (2015). "The resolution code of acute inflammation: Novel pro-resolving lipid mediators in resolution". Seminars in Immunology. 27 (3): 200–15. doi:10.1016/j.smim.2015.03.004. PMC 4515371 . PMID 25857211.
23. Weylandt KH (2015). "Docosapentaenoic acid derived metabolites and mediators - The new world of lipid mediator medicine in a nutshell". European Journal of Pharmacology. doi:10.1016/j.ejphar.2015.11.002. PMID 2654672
24. Campbell WB, Falck JR, Okita JR, Johnson AR, Callahan KS (1985). "Synthesis of dihomoprostaglandins from adrenic acid (7,10,13,16-docosatetraenoic acid) by human endothelial cells". Biochim. Biophys. Acta. 837 (1): 67–76. doi:10.1016/0005-2760(85)90086-4. PMID 3931686.
25. Kopf PG, Zhang DX, Gauthier KM, Nithipatikom K, Yi XY, Falck JR, Campbell WB (2010). "Adrenic acid metabolites as endogenous endothelium-derived and zona glomerulosa-derived hyperpolarizing factors". Hypertension. 55 (2): 547–54. doi:10.1161/HYPERTENSIONAHA.109.144147. PMC 2819927 . PMID 20038752.
Yi XY, Gauthier KM, Cui L, Nithipatikom K, Falck JR, Campbell WB (May 2007). "Metabolism of adrenic acid to vasodilatory 1alpha,1beta-dihomo-epoxyeicosatrienoic acids by bovine coronary arteries". Am J Physiol Heart Circ Physiol. 292 (5): H2265–74. doi:10.1152/ajpheart.00947.2006. PMID 17209008