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Selective Incorporation of Hetes into Epidermal Phospholipids

  • Craig C. Miller
  • Wilson Tang
  • Yunhi Cho
  • Vincent A. Ziboh
Part of the GWUMC Department of Biochemistry Annual Spring Symposia book series (GWUN)

Abstract

The skin has an active lipid metabolism and is capable of producing a variety of eicosanoids (Ruzicka and Printz, 1984). Recently, there has been particular attention directed toward the existence of epidermal lipoxygenase products and their possible role in cutaneous inflammation (Voorhees, 1983; Camp and Cunningham, 1988). This interest began with the discovery that the lesions of certain chronic inflammatory skin disorders (e.g. psoriasis and atopic dermatitis) are associated with an imbalance of lipoxygenase products, specifically elevated levels of pro-inflammatory leukotriene B4 (LTB4), a 5-lipoxygenase product of leukocytes (Grabbe et al., 1984; Brain et al., 1984; Ruzicka et al., 1986). Interestingly, the major lipoxygenase product of keratinocytes (the predominant epidermal cell-type) is the 15-lipoxygenase product 15-hydroxyeicosatetraenoic acid (15-HETE) (Burrall et al., 1985; Nugteren and Kivits, 1987), an inhibitor of 5--lipoxygenase activity in vitro (Vanderhoek et al., 1982). The potential of epidermally-derived 15-HETE to attenuate 5-lipoxygenase activity has led to speculation that there may be a local deficit of 15-HETE in lesional tissues which may in turn result in a decreased ability to limit the generation of 5-lipoxygenase products by infiltrating leukocytes. In support of this hypothesis, intralesional injections of 15-HETE have been used to clear psoriatic lesions (Fogh et al., 1988). Furthermore, certain dietary oils that result in elevated in vivo levels of epidermal 15-lipoxygenasejproducts (Miller et al., 1990; Miller et al., 1991) have been shown to be clinically effective in the treatment of psoriasis and other chronic inflammatory skin disorders (Ziboh et al., 1986; Maurice et al., 1987; Wright and Burton, 1982).

Keywords

Hydroxy Fatty Acid Phospholipid Class Intralesional Injection Lipoxygenase Product Inositol Phospholipid 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

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References

  1. Brain S., Camp R., Dowd P., Kobza Black A., and Greaves M., 1984, The release of leukotriene B4-like material in biologically active amounts from the lesional skin of patients with psoriasis, J. Invest. Dermatol. 83: 70–73.PubMedCrossRefGoogle Scholar
  2. Brezinski M.E. and Serhan C.N., 1990, Selective incorporation of (15S)hydroxyeicosatetraenoic acid in phosphatidylinositol of human neutrophils: Agonist-induced deacylation and transformation of stored hydroxyeicosanoids, Proc. Natl. Acad. Sci. 87: 6248–6252.PubMedCrossRefGoogle Scholar
  3. Burrall B.A., Wintroub B.U., and Goetzl E.J., 1985, Selective expression of 15-lipoxygenase activity by cultured human keratinocytes, Biochem. Biophys. Res. Commun. 133: 208–213.PubMedCrossRefGoogle Scholar
  4. Burrall B.A., Cheung M., Chill A., and Goetzl E.J., 1988, Enzymatic properties of the 15-lipoxygenase of human cultured keratinocytes, J. Invest. Dermatol. 91: 294–297.PubMedCrossRefGoogle Scholar
  5. Camp R.D.R. and Cunningham F.M., 1988, The role of eicosanoids in inflammatory disorders of the skin, in Eicosanoids in Inflammatory Conditions of the Lung, Skin, and Joints, Church M. and Robinson C., eds., MTP Press Ltd., Boston, pp 112–128.Google Scholar
  6. Croset M. and Lagarde M., 1983, Stereospecific inhibition of PGH2- induced platelet aggregation by lipoxygenase products of icosanoic acids, Biochem. Biophys. Res. Commun. 112: 878–883.PubMedCrossRefGoogle Scholar
  7. Fogh K., Sogaard H., Herlin T., and Kragballe K., 1988, Improvement of psoriasis vulgaris after intralesional injections of 15-hydroxyeicosatetraenoic acid (15-HETE), J. Am. Acad. Dermatol. 18: 279–285.PubMedCrossRefGoogle Scholar
  8. Grabbe J., Czarnetzki B.M., Rosenbach T., and Mardin M., 1984, Identification of chemotactic lipoxygenase products of arachidonate metabolism in psoriatic skin, J. Invest. Dermatol. 82: 477–479.PubMedCrossRefGoogle Scholar
  9. Green F.A., 1989, Generation and metabolism of lipoxygenase products in normal and membrane-damaged cultured human keratinocytes, J. Invest. Dermatol. 93: 486–491.PubMedCrossRefGoogle Scholar
  10. Holub B.J. and Skeaff C.M., 1987, Nutritional regulation of cellular phosphatidylinositol, Methods Enzymol. 141: 234–244.PubMedCrossRefGoogle Scholar
  11. Legrand A.B., Lawson J.A., Meyrick B.O., Blair I.A., and Oates J.A., 1991, Substitution of 15-hydroxyeicosatetraenoic acid in the phosphoinositide signaling pathway, J. Biol. Chem. 266: 7570–7577.PubMedGoogle Scholar
  12. Maurice P.D.L., Allen B.R., Barkley A.S.J., Cockbill S.R., Stammers J., and Bather P.C., 1987, The effects of dietary supplementation with fish oil in patients with psoriasis, Br. J. Dermatol. 117: 599–606.PubMedCrossRefGoogle Scholar
  13. Miller C.C., Ziboh V.A., Wong T., and Fletcher M.P., 1990, Dietary supplementation with oils rich in n-3 and n-6 fatty acids influences in vivo levels of epidermal lipoxygenase products in guinea pigs, J. Nutr. 120: 36–44.PubMedGoogle Scholar
  14. Miller C.C., Tang W., Ziboh V.A., and Fletcher M.P., 1991, Dietary supplementation with ethyl ester concentrates of fish oil (n-3) and borage oil (n-6) polyunsaturated fatty acids induces epidermal generation of local putative antiinflammatory metabolites, J. Invest. Dermatol. 96: 98–103.PubMedCrossRefGoogle Scholar
  15. Nugteren D.H. and Kivits G.A.A., 1987, Conversion of linoleic acid and arachidonic acid by skin epidermal lipoxygenases, Biochim. Biophys. Acta. 921: 135–141.PubMedCrossRefGoogle Scholar
  16. Ruzicka T.P. and Printz M.P., 1984, Arachidonic acid metabolism in skin: a review, Rev. Physiol. Biochem. Pharmacol. 100: 121–160.PubMedGoogle Scholar
  17. Ruzicka T., Sirmet T., Peskar B.A., and Ring J., 1986, Skin levels of arachidonic acid-derived inflammatory mediators and histamine in atopic dermatitis and psoriasis, J. Invest. Dermatol. 86: 105–108.PubMedCrossRefGoogle Scholar
  18. Spector A.A., Gordon J.A., and Moore S.A., 1988, Hydroxyeicosatetraenoic acids (HETEs), Prog. Lipid. Res. 27: 271–323.PubMedCrossRefGoogle Scholar
  19. Vanderhoek J.Y., Bryant R.W., and Bailey, J.M., 1982, Regulation of leukocyte and plateletGoogle Scholar
  20. lipoxygenases by hydroxy-eicosanoids, Biochem. Pharmacol. 31:3463–3467. Voorhees J.J., 1983, Leukotrienes and other lipoxygenase products in the pathogenesis and therapy of psoriasis and other dermatoses, Arch. Dermatol. 119:541–547.Google Scholar
  21. Wright S. and Burton J.L., 1982, Oral evening-primrose-seed oil improves atopic eczema, Lancet II,1120–1122.CrossRefGoogle Scholar
  22. Ziboh V.A., Cohen K.A., Ellis C.N., Miller C., Hamilton T.A., Kragballe K., Hydrick C.R., and Voorhees J.J., 1986, Effects of dietary supplementation of fish oil on neutrophil and epidermal fatty acids. Modulation of clinical course of psoriatic subjects, Arch. Dermatol. 122: 1277–1282.PubMedCrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media New York 1991

Authors and Affiliations

  • Craig C. Miller
    • 1
  • Wilson Tang
    • 1
  • Yunhi Cho
    • 1
  • Vincent A. Ziboh
    • 1
  1. 1.Department of Dermatology, School of MedicineUniversity of CaliforniaDavisUSA

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