Docosanoid

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In biochemistry, docosanoids are

polyunsaturated fatty acid metabolites that possess potent anti-inflammation
, tissue healing, and other activities.

Prominent docosanoids

Specialized proresolving mediator docosanoids

Potently bioactive agents of the specialized proresolving mediator class include:

These DHA metabolites possess anti-

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

isomers 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-Fαneuroprostane 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

Cells metabolize DHA to 17S-hydroperoxy-4Z,7Z,10Z,13Z,15E,19Z-docosahexaenoic acid (17-HpDHA) and then rapidly reduce this hydroperoxide to 17S-hydroxy-4Z,7Z,10Z,13Z,15E,19Z-docosahexaenoic acid (17-HDHA) and similarly metabolize DHA to 13S-hydroperoxy-4Z,7Z,10Z,14Z,16Z,19Z-docosahexaenoic acid (13-HpDHA) and then to 13S-hydroxy-4Z,7Z,10Z,14Z,16Z,19Z-docosahexaenoic 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

Cells can metabolize DHA to products that possess an oxo (i.e.

Specialized proresolving mediators § Oxo-DHA and oxo-DPA metabolites).[10]

DTA-derived docosanoids

cytochrome P450 oxidase act upon docosatetraenoic acid to produce dihomoprostaglandins,[11] dihomo-epoxyeicosatrienoic acids,[12] and dihomo-EETs.[13]

References

  1. PMID 25149823
    .
  2. PMID 25359497
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  3. S2CID 45820130
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  4. PMID 26545300
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  5. PMID 17954232
    .
  6. S2CID 34479417
    .
  7. S2CID 18265905
    .
  8. PMID 23029040
    .
  9. PMID 25857211
    .
  10. PMID 26546723
    .
  11. PMID 3931686
    .
  12. PMID 20038752
    .
  13. S2CID 86090552
    .
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