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Lipoxin A. Stereochemistry and biosynthesis.

C N Serhan, K C Nicolaou, S E Webber

    The Journal of Biological Chemistry
    |December 15, 1986
    PubMed
    Summary
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    Activated leukocytes use 15-hydroxyeicosatetraenoic acid (15-HETE) to create lipoxins (LXA), which influence cellular responses. Biologically derived LXA and synthetic LXA showed similar bioactivity in lung strip assays.

    Area of Science:

    • Biochemistry
    • Immunology
    • Eicosanoid Metabolism

    Background:

    • Lipoxin A (LXA) is a biologically active eicosanoid involved in inflammatory processes.
    • The biosynthesis and precise structure of LXA and its isomers have been areas of active research.
    • Understanding LXA formation is crucial for comprehending its role in cellular signaling and immune responses.

    Purpose of the Study:

    • To elucidate the precise structure of biologically derived Lipoxin A (LXA).
    • To identify and characterize LXA isomers produced by human leukocytes.
    • To investigate the bioactivity of LXA and its isomers in a physiological model.

    Main Methods:

    • Incubation of human leukocytes with precursor fatty acids (15-HETE or 15-HPETE) and stimuli (A23187 or fMet-Leu-Phe).

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  • Isolation and structural determination of LXA and its isomers using advanced chromatographic techniques.
  • Bioassay on guinea pig lung strips to assess the contractile activity of synthesized and biologically derived lipoxins.

    • Main Results:

    • Biologically derived LXA was identified as (5S,6R,15S)-5,6,15-trihydroxy-7,9,13-trans-11-cis-eicosatetraenoic acid.
    • Three LXA isomers (6S-LXA, 11-trans-LXA, and 6S-11-trans-LXA) were identified and characterized.
    • 18O2-labeling studies suggested a 5,6-epoxy intermediate in LXA biosynthesis; LXA induced slow, long-lasting contractions in lung strips, with synthetic and biological LXA showing indistinguishable activity.

    Conclusions:

    • Activated human leukocytes can convert exogenous 15-HETE into lipoxins, including LXA and its isomers.
    • The primary biologically active form of LXA possesses a specific stereochemistry at C-5, C-6, and C-15.
    • Lipoxins generated by leukocytes modulate cellular responses, as evidenced by their effects on smooth muscle contraction.