Bioactive lipid mediators in skin inflammation and immunity

Progress in Lipid Research

Volumn 52, Issue 1, 2013, Pages 141-164

  Kendall, Alexandra C ^a   Nicolaou, Anna ^a  

^a UNIVERSITY OF BRADFORD   (United Kingdom)

Author keywords

Eicosanoids; Endocannabinoids; Immunity; Inflammation; Skin; Sphingolipids

Indexed keywords

ENDOCANNABINOID; ICOSANOID; LIPOXYGENASE; SPHINGOLIPID;

ACNE VULGARIS; ADAPTIVE IMMUNITY; ATOPIC DERMATITIS; CONTACT DERMATITIS; DERMATITIS; FUNCTIONAL ANATOMY; HUMAN; IMMUNE SYSTEM; INNATE IMMUNITY; LIPID COMPOSITION; LIPID METABOLISM; MOLECULAR INTERACTION; MOLECULAR PATHOLOGY; NONHUMAN; PRIORITY JOURNAL; PSORIASIS; REVIEW; SIGNAL TRANSDUCTION; ULTRAVIOLET RADIATION; WOUND HEALING;

ACNE VULGARIS; DERMATITIS; EICOSANOIDS; ENDOCANNABINOIDS; HUMANS; LIPID METABOLISM; LIPIDS; PSORIASIS; SKIN; SPHINGOLIPIDS; WOUND HEALING;

EID: 84870223620     PISSN: 01637827     EISSN: 18732194     Source Type: Journal    
DOI: 10.1016/j.plipres.2012.10.003     Document Type: Review

References (345)

1. C. Bangert, P.M. Brunner, and G. Stingl Immune functions of the skin Clin Dermatol 29 2011 360 376
2. F.O. Nestle, P. Di Meglio, J.-Z. Qin, and B.J. Nickoloff Skin immune sentinels in health and disease Nat Rev Immunol 9 2009 679 691
3. V. Kotnik Complement in skin diseases Acta Dermatovenerol Alp Panonica Adriat 20 2011 3 11
4. C. Albanesi, and S. Pastore Pathobiology of chronic inflammatory skin diseases: interplay between keratinocytes and immune cells as a target for anti-inflammatory drugs Curr Drug Metab 11 2010 210 227
5. G.O. Burr, and M.M. Burr A new deficiency disease produced by the rigid exclusion of fat from the diet J Biol Chem 82 1929 345 367
6. P.C. Calder Polyunsaturated fatty acids and inflammation Prostaglandins Leukot Essent Fatty Acids 75 2006 197 202
7. L.A. Afman, and M. Müller Human nutrigenomics of gene regulation by dietary fatty acids Prog Lipid Res 51 2012 63 70
8. Y. Uchida, and W.M. Holleran Omega-O-acylceramide, a lipid essential for mammalian survival J Dermatol Sci 51 2008 77 87
9. S.M. Pilkington, R.E. Watson, A. Nicolaou, and L.E. Rhodes Omega-3 polyunsaturated fatty acids: photoprotective macronutrients Exp Dermatol 20 2011 537 543
10. D.R. Drake, K.A. Brogden, D.V. Dawson, and P.W. Wertz Thematic review series: skin lipids. Antimicrobial lipids at the skin surface J Lipid Res 49 2008 4 11
11. Nicolaou A. Eicosanoids in skin inflammation. Prostaglandins Leukot Essent Fatty Acids; 2012. http://dx.doi.org/10.1016/j.plefa.2012.03.009.
12. P. Kupczyk, A. Reich, and J.C. Szepietowski Cannabinoid system in the skin-a possible target for future therapies in dermatology Exp Dermatol 18 2009 669 679
13. K. Thomas A view on sphingolipids and disease Chem Phys Lipids 164 2011 590 606
14. G.M. Balbas, M.S. Regana, and P.U. Millet Study on the use of omega-3 fatty acids as a therapeutic supplement in treatment of psoriasis Clin Cosmetic Invest Dermatol 4 2011 73 77
15. M.H. Zulfakar, M. Edwards, and C.M. Heard Is there a role for topically delivered eicosapentaenoic acid in the treatment of psoriasis? Eur J Dermatol 17 2007 284 291
16. D. Khnykin, J.H. Miner, and F. Jahnsen Role of fatty acid transporters in epidermis: implications for health and disease Dermatoendocrinol 3 2011 53 61
17. P.W. Wertz Epidermal lipids Semin Dermatol 11 1992 106 113
18. E.W.M. Verhoeven, F.W. Kraaimaat, C. van Weel, P.C.M. van de Kerkhof, P. Duller, and P.G.M. van der Valk Skin diseases in family medicine: prevalence and health care use Ann Fam Med 6 2008 349 354
19. J.M. Jungersted, L.I. Hellgren, G.B.E. Jemec, and T. Agner Lipids and skin barrier function-a clinical perspective Contact Dermatitis 58 2008 255 262
20. H.S. Hansen, and B. Jensen Essential function of linoleic acid esterified in acylglucosylceramide and acylceramide in maintaining the epidermal water permeability barrier. Evidence from feeding studies with oleate, linoleate, arachidonate, columbinate and alpha-linolenate Biochim Biophys Acta 834 1985 357 363
21. E. Proksch, J.M. Brandner, and J.-M. Jensen The skin: an indispensable barrier Exp Dermatol 17 2008 1063 1072
22. F. Berthaud, and M. Boncheva Correlation between the properties of the lipid matrix and the degrees of integrity and cohesion in healthy human Stratum corneum Exp Dermatol 20 2011 255 262
23. C. Hwa, E.A. Bauer, and D.E. Cohen Skin biology Dermatol Therapy 24 2011 464 470
24. B.E. Clausen, and J.M. Kel Langerhans cells: critical regulators of skin immunity? Immunol Cell Biol 88 2010 351 360
25. N. Boulais, and L. Misery Merkel cells J Am Acad Dermatol 57 2007 147 165
26. G. Szabo The number of melanocytes in human epidermis Br Med J 1 1954 1016 1017
27. J.E. Lai-Cheong, and J.A. McGrath Structure and function of skin, hair and nails Medicine (Baltimore) 37 2009 223 226
28. P.S. Friedmann, I. Strickland, A.A. Memon, and P.M. Johnson Early time course of recruitment of immune surveillance in human skin after chemical provocation Clin Exp Immunol 91 1993 351 356
29. D.D. Kish, X. Li, and R.L. Fairchild CD8 T cells producing IL-17 and IFN-γ initiate the innate immune response required for responses to antigen skin challenge J Immunol 182 2009 5949 5959
30. A. Iyer, D.P. Fairlie, J.B. Prins, B.D. Hammock, and L. Brown Inflammatory lipid mediators in adipocyte function and obesity Nat Rev Endocrinol 6 2010 71 82
31. T. Ezure, and S. Amano Negative regulation of dermal fibroblasts by enlarged adipocytes through release of free fatty acids J Invest Dermatol 131 2011 2004 2009
32. I. Falcao-Pires, P. Castro-Chaves, D. Miranda-Silva, A.P. Lourenco, and A.F. Leite-Moreira Physiological, pathological and potential therapeutic roles of adipokines Drug Discovery Today 2012 http://dx.doi.org/10.1016/j.drudis.2012. 04.007
33. K.M. Moon, Y.H. Park, J.S. Lee, Y.B. Chae, M.M. Kim, and D.S. Kim The effect of secretory factors of adipose-derived stem cells on human keratinocytes Int J Mol Sci 13 2012 1239 1257
34. S.H. Lee, S.Y. Jin, J.S. Song, K.K. Seo, and K.H. Cho Paracrine effects of adipose-derived stem cells on keratinocytes and dermal fibroblasts Ann Dermatol 24 2012 136 143
35. B. Homey, M. Steinhoff, T. Ruzicka, and D.Y.M. Leung Cytokines and chemokines orchestrate atopic skin inflammation J Allergy Clin Immunol 118 2006 178 189
36. A. Saalbach, C. Klein, C. Schirmer, W. Briest, U. Anderegg, and J.C. Simon Dermal fibroblasts promote the migration of dendritic cells J Invest Dermatol 130 2009 444 454
37. A. Fukunaga, N.M. Khaskhely, C.S. Sreevidya, S.N. Byrne, and S.E. Ullrich Dermal dendritic cells, and not Langerhans cells, play an essential role in inducing an immune response J Immunol 180 2008 3057 3064
38. I. Kimber, M. Cumberbatch, and R.J. Dearman Langerhans cell migration: not necessarily always at the center of the skin sensitization universe J Invest Dermatol 129 2009 1852 1853
39. P. Krause, M. Bruckner, C. Uermösi, E. Singer, M. Groettrup, and D.F. Legler Prostaglandin E2 enhances T-cell proliferation by inducing the costimulatory molecules OX40L, CD70, and 4-1BBL on dendritic cells Blood 113 2009 2451 2460
40. A.P. Pentland, and M.G. Mahoney Keratinocyte prostaglandin synthesis is enhanced by IL-1 J Invest Dermatol 94 1990 43 46
41. A. McIlroy, G. Caron, S. Blanchard, I. Frémaux, D. Duluc, and Y. Delneste Histamine and prostaglandin E2 up-regulate the production of Th2-attracting chemokines (CCL17 and CCL22) and down-regulate IFN-γ-induced CXCL10 production by immature human dendritic cells Immunology 117 2006 507 516
42. 2 suppresses IL-12 release by dendritic cells leading to Th2 polarized immune responses in vivo Immunobiology 211 2006 463 472
43. + helper T cells J Exp Med 147 1978 446 458
44. S. Aggarwal, N. Ghilardi, M.-H. Xie, F.J. de Sauvage, and A.L. Gurney Interleukin-23 promotes a distinct CD4 T cell activation state characterized by the production of interleukin-17 J Biol Chem 278 2003 1910 1914
45. + type 1 cytotoxic T cells both play a crucial role in the full development of contact hypersensitivity J Immunol 165 2000 6783 6790
46. S. Petrosino, L. Cristino, M. Karsak, E. Gaffal, N. Ueda, and T. Tüting Protective role of palmitoylethanolamide in contact allergic dermatitis Allergy 65 2010 698 711
47. G.R. Lee, and R.A. Flavell Transgenic mice which overproduce Th2 cytokines develop spontaneous atopic dermatitis and asthma Int Immunol 16 2004 1155 1160
48. F.M. Marelli-Berg, L. Cannella, F. Dazzi, and V. Mirenda The highway code of T cell trafficking J Pathol 214 2008 179 189
49. V.A. Ziboh, and R.S. Chapkin Metabolism and function of skin lipids Prog Lipid Res 27 1988 81 105
50. G.M. Gray, and H.J. Yardley Lipid compositions of cells isolated from pig, human, and rat epidermis J Lipid Res 16 1975 434 440
51. M.A. Lampe, A.L. Burlingame, J. Whitney, M.L. Williams, B.E. Brown, and E. Roitman Human stratum corneum lipids: characterization and regional variations J Lipid Res 24 1983 120 130
52. N.A. Coolen, K.C. Schouten, E. Middelkoop, and M.M. Ulrich Comparison between human fetal and adult skin Arch Dermatol Res 302 2010 47 55
53. E.J. Kim, M.-K. Kim, X.-J. Jin, J.-H. Oh, J.E. Kim, and J.H. Chung Skin aging and photoaging alter fatty acids composition, including 11,14,17-eicosatrienoic acid, in the epidermis of human skin J Korean Med Sci 25 2010 980 983
54. C. De Luca, and G. Valacchi Surface lipids as multifunctional mediators of skin responses to environmental stimuli Mediators Inflamm 2010 2010
55. E. Camera, M. Ludovici, M. Galante, J.-L. Sinagra, and M. Picardo Comprehensive analysis of the major lipid classes in sebum by rapid resolution high-performance liquid chromatography and electrospray mass spectrometry J Lipid Res 51 2010 3377 3388
56. N. Nicolaides, and G.C. Wells On the biogenesis of the free fatty acids in human skin surface fat J Invest Dermatol 29 1957 423 433
57. T. Nakatsuji, M.C. Kao, L. Zhang, C.C. Zouboulis, R.L. Gallo, and C.-M. Huang Sebum free fatty acids enhance the innate immune defense of human sebocytes by upregulating β-defensin-2 expression J Invest Dermatol 130 2010 985 994
58. S. Ní Raghallaigh, K. Bender, N. Lacey, L. Brennan, and F.C. Powell The fatty acid profile of the skin surface lipid layer in papulopustular rosacea Br J Dermatol 166 2012 279 287
59. S.P. Panicker, T. Ganguly, M. Consolo, V. Price, P. Mirmirani, and K. Honda Sterol intermediates of cholesterol biosynthesis inhibit hair growth and trigger an innate immune response in cicatricial alopecia PLoS ONE 7 2012 e38449
60. G. Grubauer, K.R. Feingold, and P.M. Elias Relationship of epidermal lipogenesis to cutaneous barrier function J Lipid Res 28 1987 746 752
61. V.A. Ziboh, C.C. Miller, and Y. Cho Metabolism of polyunsaturated fatty acids by skin epidermal enzymes: generation of antiinflammatory and antiproliferative metabolites Am J Clin Nutr 71 2000 361S 366S
62. M.M. McCusker, and J.M. Grant-Kels Healing fats of the skin: the structural and immunologic roles of the ω-6 and ω-3 fatty acids Clin Dermatol 28 2010 440 451
63. N.Y. Schurer, W. Stremmel, J.U. Grundmann, V. Schliep, H. Kleinert, and N.M. Bass Evidence for a novel keratinocyte fatty acid uptake mechanism with preference for linoleic acid: comparison of oleic and linoleic acid uptake by cultured human keratinocytes, fibroblasts and a human hepatoma cell line Biochim Biophys Acta 1211 1994 51 60
64. O. Macheleidt, H.W. Kaiser, and K. Sandhoff Deficiency of epidermal protein-bound ω-hydroxyceramides in atopic dermatitis J Invest Dermatol 119 2002 166 173
65. S.C. Wallingford, S.M. Pilkington, K.A. Massey, N.M. Al-Aasswad, T.I. Ibiebele, and M. Celia Hughes Three-way assessment of long-chain n-3 PUFA nutrition: by questionnaire and matched blood and skin samples Br J Nutr 2012 1 8
66. R.S. Chapkin, and V.A. Ziboh Inability of skin enzyme preparations to biosynthesize arachidonic acid from linoleic acid Biochem Biophys Res Commun 124 1984 784 792
67. K.A. Massey, and A. Nicolaou Lipidomics of polyunsaturated-fatty-acid- derived oxygenated metabolites Biochem Soc Trans 39 2011 1240 1246
68. E.A. Dennis, J. Cao, Y.H. Hsu, V. Magrioti, and G. Kokotos Phospholipase A2 enzymes: physical structure, biological function, disease implication, chemical inhibition and therapeutic intervention Chem Rev 111 2011 6130 6185
69. 2 in allergic response and parturition Nature 390 1997 618 622
70. A. Chan, and T. Mauro Acidification in the epidermis and the role of secretory phospholipases Dermatoendocrinology 3 2011 84 90
71. 2 in human epidermis J Invest Dermatol 114 2000 960 966
72. M. Murakami, and I. Kudo Prostaglandin E synthase: a novel drug target for inflammation and cancer Curr Pharm Des 12 2006 943 954
73. Y. Urade, and N. Eguchi Lipocalin-type and hematopoietic prostaglandin D synthases as a novel example of functional convergence Prostaglandins Other Lipid Mediat 68-69 2002 375 382
74. K. Watanabe, and F. Prostaglandin Synthase Prostaglandins Other Lipid Mediat 68-69 2002 401 407
75. M.C. Cathcart, J.V. Reynolds, K.J. O'Byrne, and G.P. Pidgeon The role of prostacyclin synthase and thromboxane synthase signaling in the development and progression of cancer Biochim Biophys Acta 1805 2010 153 166
76. A.T. Black, J.P. Gray, M.P. Shakarjian, V. Mishin, D.L. Laskin, and D.E. Heck UVB light upregulates prostaglandin synthases and prostaglandin receptors in mouse keratinocytes Toxicol Appl Pharmacol 232 2008 14 24
77. M. Kapoor, F. Kojima, L. Yang, and L.J. Crofford Sequential induction of pro- and anti-inflammatory prostaglandins and peroxisome proliferators-activated receptor-gamma during normal wound healing: a time course study Prostaglandins Leukot Essent Fatty Acids 76 2007 103 112
78. 2 generation by omega-3 fatty acids in THP-1 macrophages and Langerhans dendritic cells J Inflamm Res 5 2012 37 50
79. W.L. Smith Cyclooxygenases, peroxide tone and the allure of fish oil Curr Opin Cell Biol 17 2005 174 182
80. U. Janssen-Timmen, P.J. Vickers, U. Wittig, W.D. Lehmann, H.J. Stark, and N.E. Fusenig Expression of 5-lipoxygenase in differentiating human skin keratinocytes Proc Natl Acad Sci USA 92 1995 6966 6970
81. H. Hussain, L.P. Shornick, V.R. Shannon, J.D. Wilson, C.D. Funk, and A.P. Pentland Epidermis contains platelet-type 12-lipoxygenase that is overexpressed in germinal layer keratinocytes in psoriasis Am J Physiol-Cell Physiol 266 1994 C243 C253
82. A. Nicolaou, M. Masoodi, K. Gledhill, A.K. Haylett, A.J. Thody, and D.J. Tobin The eicosanoid response to high dose UVR exposure of individuals prone and resistant to sunburn Photochem Photobiol Sci 11 2012 371 380
83. H. Kuhn, and V.B. O'Donnell Inflammation and immune regulation by 12/15-lipoxygenases Prog Lipid Res 45 2006 334 356
84. M. Jisaka, R.B. Kim, W.E. Boeglin, and A.R. Brash Identification of amino acid determinants of the positional specificity of mouse 8S-lipoxygenase and human 15S-lipoxygenase-2 J Biol Chem 275 2000 1287 1293
85. M.A. Gijón, S. Zarini, and R.C. Murphy Biosynthesis of eicosanoids and transcellular metabolism of leukotrienes in murine bone marrow cells J Lipid Res 48 2007 716 725
86. L. Iversen, K. Fogh, V.A. Ziboh, P. Kristensen, A. Schmedes, and K. Kragballe Leukotriene B4 formation during human neutrophil keratinocyte interactions: evidence for transformation of leukotriene A4 by putative keratinocyte leukotriene A4 hydrolase J Invest Dermatol 100 1993 293 298
87. J. Breton, D. Woolf, P. Young, and M. Chabot-Fletcher Human keratinocytes lack the components to produce leukotriene B4 J Invest Dermatol 106 1996 162 167
88. R. Horrillo, A. González-Périz, M. Martínez- Clemente, M. López-Parra, N. Ferré, and E. Titos 5-Lipoxygenase activating protein signals adipose tissue inflammation and lipid dysfunction in experimental obesity J Immunol 184 2010 3978 3987
89. O. Kowal-Bielecka, O. Distler, M. Neidhart, P. Künzler, J. Rethage, and M. Nawrath Evidence of 5-lipoxygenase overexpression in the skin of patients with systemic sclerosis: a newly identified pathway to skin inflammation in systemic sclerosis Arthritis Rheum 44 2001 1865 1875
90. L.E. Rhodes, K. Gledhill, M. Masoodi, A.K. Haylett, M. Brownrigg, and A.J. Thody The sunburn response in human skin is characterized by sequential eicosanoid profiles that may mediate its early and late phases FASEB J 23 2009 3947 3956
91. A. Konkel, and W.-H. Schunck Role of cytochrome P450 enzymes in the bioactivation of polyunsaturated fatty acids Biochim Biophys Acta (BBA)-Proteins Proteomics 1814 2011 210 222
92. J. Capdevila, J. Falck, and R. Estabrook Cytochrome P450 and the arachidonate cascade FASEB J 6 1992 731 736
93. J.M. Baron, and C. Skazik Research in practice: the second barrier of the human skin J Deutsch Dermatol Ges 8 2010 155 158
94. A. Sala, G. Folco, and R.C. Murphy Transcellular biosynthesis of eicosanoids Pharmacol Rep 62 2010 503 510
95. B.L. Judson, A. Miyaki, V.D. Kekatpure, B. Du, P. Gilleaudeau, and M. Sullivan-Whalen UV radiation inhibits 15-hydroxyprostaglandin dehydrogenase levels in human skin: evidence of transcriptional suppression Cancer Prev Res 3 2010 1104 1111
96. V.A. Ziboh, J.T. Lord, and N.S. Penneys Alterations of prostaglandin E2-9-ketoreductase activity in proliferating skin J Lipid Res 18 1977 37 43
97. R. Camp, and M.W. Greaves The catabolism of prostaglandins by rat skin Biochem J 186 1980 153 160
98. K. Tsuboi, Y. Sugimoto, and A. Ichikawa Prostanoid receptor subtypes Prostaglandins Other Lipid Mediat 68-69 2002 535 556
99. V.C. Sandulache, A. Parekh, H.-S. Li-Korotky, J.E. Dohar, and P.A. Hebda Prostaglandin E2 differentially modulates human fetal and adult dermal fibroblast migration and contraction: implication for wound healing Wound Repair Regen 14 2006 633 643
100. 2 is a UVR-inducible autocrine factor for human melanocytes that stimulates tyrosinase activation Exp Dermatol 19 2010 682 684
101. 2, in adult human epidermis J Invest Dermatol 124 2005 965 970
102. Y. Matsushima, T. Satoh, Y. Yamamoto, M. Nakamura, and H. Yokozeki Distinct roles of prostaglandin D2 receptors in chronic skin inflammation Mol Immunol 49 2011 304 310
103. S.A. Boehme, K. Franz-Bacon, E.P. Chen, R. Šášik, L.J. Sprague, and T.W. Ly A small molecule CRTH2 antagonist inhibits FITC-induced allergic cutaneous inflammation Int Immunol 21 2009 81 93
104. M. Nakamura, and T. Shimizu Leukotriene receptors Chem Rev 111 2011 6231 6298
105. Y. Kanaoka, and J.A. Boyce Cysteinyl leukotrienes and their receptors: cellular distribution and function in immune and inflammatory responses J Immunol 173 2004 1503 1510
106. C. Kim, H.C. Ryu, and J.H. Kim Low-dose UVB irradiation stimulates matrix metalloproteinase-1 expression via a BLT2-linked pathway in HaCaT cells Exp Mol Med 42 2010 833 841
107. D.S. Keeney, C. Skinner, J.B. Travers, J.H. Capdevila, L.B. Nanney, and L.E. King Differentiating keratinocytes express a novel cytochrome P450 enzyme, CYP2B19, having arachidonate monooxygenase activity J Biol Chem 273 1998 32071 32079
108. H. Yoo, B. Jeon, M.-S. Jeon, H. Lee, and T.-Y. Kim Reciprocal regulation of 12- and 15-lipoxygenases by UV-irradiation in human keratinocytes FEBS Lett 582 2008 3249 3253
109. S.A. Abd-El-Aleem, M.W.J. Ferguson, I. Appleton, A. Bhowmick, C.N. McCollum, and G.W. Ireland Expression of cyclooxygenase isoforms in normal human skin and chronic venous ulcers J Pathol 195 2001 616 623
110. K. Kragballe, G. Pinnamaneni, L. Desjarlais, E.A. Duell, and J.J. Voorhees Dermis-derived 15-hydroxy-eicosatetraenoic acid inhibits epidermal 12-lipoxygenase activity J Invest Dermatol 87 1986 494 498
111. 4 production and 5-lipoxygenase expression in normal human dermal fibroblasts in vitro Photochem Photobiol 82 2006 665 669
112. 1-induced collagen synthesis Wound Repair Regen 15 2007 122 133
113. J.M. Baron, R. Heise, W.S. Blaner, M. Neis, S. Joussen, and A. Dreuw Retinoic acid and its 4-oxo metabolites are functionally active in human skin cells in vitro J Invest Dermatol 125 2005 143 153
114. 2 production in FM55 melanoma cells is regulated by α-melanocyte-stimulating hormone and is not related to melanin production Exp Dermatol 19 2010 751 753
115. 2 in response to nicotinic acid J Invest Dermatol 126 2006 2637 2646
116. 2 and the ligation of PPARγ J Clin Investig 112 2003 945 955
117. 2 receptor, EP2, stimulates keratinocyte proliferation in mouse skin by G protein-dependent and β-arrestin1-dependent signaling pathways J Biol Chem 285 2010 39672 39681
118. 2 induces the production of human β-defensin-3 in human keratinocytes Biochem Pharmacol 79 2010 982 989
119. 2 and enamel matrix derivative on the proliferation of human gingival and dermal fibroblasts and gingival keratinocytes J Periodontal Res 45 2010 731 740
120. 2 Burns 32 2006 299 304
121. Y. Yang, S.K. Shim, H.-A. Kim, M. Seon, E. Yang, and D. Cho CXC chemokine receptor 4 is essential for Lipo-PGE1-enhanced migration of human dermal fibroblasts Exp Dermatol 21 2012 75 77
122. H.H. Kim, C.M. Shin, C.-H. Park, K.H. Kim, K.H. Cho, and H.C. Eun Eicosapentaenoic acid inhibits UV-induced MMP-1 expression in human dermal fibroblasts J Lipid Res 46 2005 1712 1720
123. 2 production Exp Dermatol 15 2006 769 774
124. 2 are active in sebaceous glands J Mol Med 84 2006 75 87
125. 2 does not affect testosterone production Br J Dermatol 161 2009 674 677
126. A. Wrobel, H. Seltmann, S. Fimmel, K. Muller-Decker, M. Tsukada, and B. Bogdanoff Differentiation and apoptosis in human immortalized sebocytes J Invest Dermatol 120 2003 175 181
127. 2 production J Invest Dermatol 125 2005 865 872
128. 2 in the skin Am J Pathol 176 2010 227 237
129. 2 in the inhibition of epidermal Langerhans cell migration during Schistosomiasis infection J Exp Med 193 2001 1135 1148
130. 2 is generally required for human dendritic cell migration and exerts its effect via EP2 and EP4 receptors J Immunol 176 2006 966 973
131. 2 in podosome dissolution and induction of high-speed migration during dendritic cell maturation J Immunol 177 2006 1567 1574
132. 2 induces matrix metalloproteinase 9 expression in dendritic cells through two independent signaling pathways leading to activator protein 1 (AP-1) activation J Biol Chem 286 2011 38913 38923
133. S. Doepping, C.D. Funk, A.J.R. Habenicht, and R. Spanbroek Selective 5-lipoxygenase expression in Langerhans cells and impaired dendritic cell migration in 5-LO-deficient mice reveal leukotriene action in skin J Invest Dermatol 127 2007 1692 1700
134. 4 prevents the complete maturation of murine dendritic cells and modifies interleukin-12/interleukin-23 balance Immunology 134 2011 185 197
135. M.K. Church, T.J. Griffiths, S. Jeffery, L.C. Ravell, A.S. Cowburn, and A.P. Sampson Are cysteinyl leukotrienes involved in allergic responses in human skin? Clin Exp Allergy 32 2002 1013 1019
136. J.Y. Lee, A.Y. Choi, Y.T. Oh, W. Choe, E.-J. Yeo, and J. Ha AMP-activated protein kinase mediates T cell activation-induced expression of FasL and COX-2 via protein kinase C theta-dependent pathway in human Jurkat T leukemia cells Cell Signal 24 2012 1195 1207
137. 2 and T cells: friends or foes? Immunol Cell Biol 90 2012 579 586
138. 2 through the p38 MAPK pathway is responsible for the antipruritic activity of sertaconazole nitrate J Invest Dermatol 130 2010 2448 2456
139. h2) Int Immunol 21 2009 621 632
140. 2 receptor DP2/CRTH2 increases allergic inflammation in mouse J Immunol 174 2005 3703 3708
141. 2 suppresses human NK cell function via signaling through D prostanoid receptor J Immunol 179 2007 2766 2773
142. M.D. Diaz-Munoz, I.C. Osma-Garcia, M. Fresno, and M.A. Iniguez Involvement of PGE2 and cyclic AMP signaling pathway in the up-regulation of COX-2 and mPGES-1 expression in LPS-activated macrophages Biochem J 15 2012 451 461
143. F. Cipollone, M.L. Fazia, A. Iezzi, C. Cuccurullo, D. De Cesare, and S. Ucchino Association between prostaglandin E receptor subtype EP4 overexpression and unstable phenotype in atherosclerotic plaques in human Arterioscler Thromb Vasc Biol 25 2005 1925 1931
144. P.M. Dowd, A.K. Black, P.M. Woollard, R.D.R. Camp, and M.W. Greaves Cutaneous responses to 12-hydroxy-5,8,10,14-eicosatetraenoic acid (12-HETE) J Invest Dermatol 84 1985 537 541
145. C.N. Serhan, A. Jain, S. Marleau, C. Clish, A. Kantarci, and B. Behbehani Reduced inflammation and tissue damage in transgenic rabbits overexpressing 15-lipoxygenase and endogenous anti-inflammatory lipid mediators J Immunol 171 2003 6856 6865
146. S. Xi, H. Pham, and V.A. Ziboh Supression of proto-oncogene (AP-1) in a model of skin epidermal hyperproliferation is reversed by topical application of 13-hydroxyoctadecadienoic acid and 15-hydroxyeicosatrienoic acid Prostaglandins Leukot Essent Fatty Acids 62 2000 13 19
147. Y.-S. Piao, Y.-C. Du, H. Oshima, J.-C. Jin, M. Nomura, and T. Yoshimoto Platelet-type 12-lipoxygenase accelerates tumor promotion of mouse epidermal cells through enhancement of cloning efficiency Carcinogenesis 29 2008 440 447
148. D. Schweiger, G. Fürstenberger, and P. Krieg Inducible expression of 15-lipoxygenase-2 and 8-lipoxygenase inhibits cell growth via common signaling pathways J Lipid Res 48 2007 553 564
149. N. Godessart, M. Camacho, J. Lopez-Belmonte, R. Anton, M. Garcia, and J.-M. de Moragas Prostaglandin H-synthase-2 is the main enzyme involved in the biosynthesis of octadecanoids from linoleic acid in human dermal fibroblasts stimulated with interleukin-1β J Invest Dermatol 107 1996 726 732
150. C.C. Miller, and V.A. Ziboh Induction of epidermal hyperproliferation by topical n-3 polyunsaturated fatty acids on guinea pig skin linked to decreased levels of 13-hydroxyoctadecadienoic acid (13-HODE) J Invest Dermatol 94 1990 353 358
151. E. Ogawa, Y. Owada, S. Ikawa, Y. Adachi, T. Egawa, and K. Nemoto Epidermal FABP (FABP5) regulates keratinocyte differentiation by 13(S)-HODE-mediated activation of the NF-κB signaling pathway J Invest Dermatol 131 2011 604 612
152. T. Hattori, H. Obinata, A. Ogawa, M. Kishi, K. Tatei, and O. Ishikawa G2A plays proinflammatory roles in human keratinocytes under oxidative stress as a receptor for 9-hydroxyoctadecadienoic acid J Invest Dermatol 128 2007 1123 1133
153. P.A. Ladd, L. Du, J.H. Capdevila, R. Mernaugh, and D.S. Keeney Epoxyeicosatrienoic acids activate transglutaminases in situ and induce cornification of epidermal keratinocytes J Biol Chem 278 2003 35184 35192
154. J. Wang, and N. Ueda Biology of endocannabinoid synthesis system Prostaglandins Other Lipid Mediat 89 2009 112 119
155. C.C. Felder, E.M. Briley, J. Axelrod, J.T. Simpson, K. Mackie, and W.A. Devane Anandamide, an endogenous cannabimimetic eicosanoid, binds to the cloned human cannabinoid receptor and stimulates receptor-mediated signal transduction Proc Natl Acad Sci USA 90 1993 7656 7660
156. + cells Biochem J 346 2000 369 374
157. S. Oka, J. Wakui, S. Ikeda, S. Yanagimoto, S. Kishimoto, and M. Gokoh Involvement of the cannabinoid CB2 receptor and is endogenous ligand 2-arachidonoylglycerol in oxazolone-induced contact dermatitis in mice J Immunol 177 2006 8796 8805
158. N. Ghafouri, B. Ghafouri, B. Larsson, M.V. Turkina, L. Karlsson, and C.J. Fowler High levels of N-palmitoylethanolamide and N-stearoylethanolamide in microdialysate samples from myalgic trapezius muscle in women PLoS ONE 6 2011 e27257
159. H.S. Hansen, and A. Artmann Endocannabinoids and nutrition J Neuroendocrinol 20 2008 94 99
160. J. Wang, Y. Okamoto, J. Morishita, K. Tsuboi, A. Miyatake, and N. Ueda Functional analysis of the purified anandamide-generating phospholipase D as a member of the metallo-beta-lactamase family J Biol Chem 281 2006 12325 12335
161. U. Yapa, J.J. Prusakiewicz, A.D. Wrightstone, L.J. Christine, J. Palandra, and E. Groeber High-performance liquid chromatography-tandem mass spectrometry assay of fatty acid amide hydrolase (FAAH) in blood: FAAH inhibition as clinical biomarker Anal Biochem 421 2012 556 565
162. N.T. Snider, V.J. Walker, and P.F. Hollenberg Oxidation of the endogenous cannabinoid arachidonoyl ethanolamide by the cytochrome P450 monooxygenases: physiological and pharmacological implications Pharmacol Rev 62 2010 136 154
163. N. Ueda, K. Tsuboi, T. Uyama, and T. Ohnishi Biosynthesis and degradation of the endocannabinoid 2-arachidonoylglycerol BioFactors 37 2011 1 7
164. G. Labar, J. Wouters, and D.M. Lambert A review on the monoacylglycerol lipase: at the interface between fat and endocannabinoid signalling Curr Med Chem 17 2010 2588 2607
165. M. Pucci, N. Pasquariello, N. Battista, M. Di Tommaso, C. Rapino, and F. Fezza Endocannabinoids stimulate human melanogenesis via type-1 cannabinoid receptor J Biol Chem 287 2012 15466 15478
166. C. Kuc, A. Jenkins, and R.T. Van Dross Arachidonoyl ethanolamide (AEA)-induced apoptosis is mediated by J-series prostaglandins and is enhanced by fatty acid amide hydrolase (FAAH) blockade Mol Carcinog 51 2012 139 149
167. M. Maccarrone, M. Di Rienzo, N. Battista, V. Gasperi, P. Guerrieri, and A. Rossi The endocannabinoid system in human keratinocytes J Biol Chem 278 2003 33896 33903
168. J.M. McPartland Expression of the endocannabinoid system in fibroblasts and myofascial tissues J Bodywork Mov Ther 12 2008 169 182
169. M.G.J. Balvers, K.C.M. Verhoeckx, P. Plastina, H.M. Wortelboer, J. Meijerink, and R.F. Witkamp Docosahexaenoic acid and eicosapentaenoic acid are converted by 3T3-L1 adipocytes to N-acyl ethanolamines with anti-inflammatory properties Biochim Biophys Acta (BBA)-Mol Cell Biol Lipids 1801 2010 1107 1114
170. K.R. Kozak, B.C. Crews, J.D. Morrow, L.-H. Wang, Y.H. Ma, and R. Weinander Metabolism of the endocannabinoids, 2-arachidonylglycerol and anandamide, into prostaglandin, thromboxane, and prostacyclin glycerol esters and ethanolamides J Biol Chem 277 2002 44877 44885
171. L.D. Petrocellis, M.G. Cascio, and V.D. Marzo The endocannabinoid system: a general view and latest additions Br J Pharmacol 141 2004 765 774
172. M. Kaczocha, S. Vivieca, J. Sun, S.T. Glaser, and D.G. Deutsch Fatty acid-binding proteins transport N-acylethanolamines to nuclear receptors and are targets of endocannabinoid transport inhibitors J Biol Chem 287 2012 3415 3424
173. 2 in immune regulation: therapeutic prospects for neuroinflammation Expert Rev Mol Med 11 2009 e3
174. K. Starowicz, S. Nigam, and V. DiMarzo Biochemistry and pharmacology of endovanilloids Pharmacol Ther 114 2007 13 33
175. S.E. O'Sullivan, and D.A. Kendall Cannabinoid activation of peroxisome proliferator-activated receptors: potential for modulation of inflammatory disease Immunobiology 215 2010 611 616
176. J.E. Lauckner, J.B. Jensen, H.-Y. Chen, H.-C. Lu, B. Hille, and K. Mackie GPR55 is a cannabinoid receptor that increases intracellular calcium and inhibits M current Proc Natl Acad Sci USA 105 2008 2699 2704
177. M.-T. Samson, A. Small-Howard, L.M.N. Shimoda, M. Koblan-Huberson, A.J. Stokes, and H. Turner Differential roles of CB1 and CB2 cannabinoid receptors in mast cells J Immunol 170 2003 4953 4962
178. B.I. Toth, N. Dobrosi, A. Dajnoki, G. Czifra, A. Olah, and A.G. Szollosi Endocannabinoids modulate human epidermal keratinocyte proliferation and survival via the sequential engagement of cannabinoid receptor-1 and transient receptor potential vanilloid-1 J Invest Dermatol 131 2011 1095 1104
179. N. Dobrosi, B.I. Tóth, G. Nagy, A. Dózsa, T. Géczy, and L. Nagy Endocannabinoids enhance lipid synthesis and apoptosis of human sebocytes via cannabinoid receptor-2-mediated signaling FASEB J 22 2008 3685 3695
180. S. Ständer, M. Schmelz, D. Metze, T. Luger, and R. Rukwied Distribution of cannabinoid receptor 1 (CB1) and 2 (CB2) on sensory nerve fibers and adnexal structures in human skin J Dermatol Sci 38 2005 177 188
181. L. Tedesco, A. Valerio, M. Dossena, A. Cardile, M. Ragni, and C. Pagano Cannabinoid receptor stimulation impairs mitochondrial biogenesis in mouse white adipose tissue, muscle, and liver Diabetes 59 2010 2826 2836
182. S. Galiègue, S. Mary, J. Marchand, D. Dussossoy, D. Carrière, and P. Carayon Expression of central and peripheral cannabinoid receptors in human immune tissues and leukocyte subpopulations Eur J Biochem 232 1995 54 61
183. P.W. Wacnik, K.M. Luhr, R.H. Hill, H.-G. Ljunggren, K. Kristensson, and M. Svensson Cannabinoids affect dendritic cell (DC) potassium channel function and modulate DC T cell stimulatory capacity J Immunol 181 2008 3057 3066
184. 1 receptor antagonist and induces pro-allergic effects in skin Biochem Pharmacol 79 2010 1815 1826
185. D.J. Rog Cannabis-based medicines in multiple sclerosis-a review of clinical studies Immunobiology 215 2010 658 672
186. A.A. Izzo, and M. Camilleri Cannabinoids in intestinal inflammation and cancer Pharmacol Res 60 2009 117 125
187. 2 receptors PLoS ONE 5 2010 e8688
188. C. Börner, M. Smida, V. Höllt, B. Schraven, and J. Kraus Cannabinoid receptor type 1- and 2-mediated increase in cyclic AMP inhibits T cell receptor-triggered signaling J Biol Chem 284 2009 35450 35460
189. C. Börner, V. Höllt, W. Sebald, and J. Kraus Transcriptional regulation of the cannabinoid receptor type 1 gene in T cells by cannabinoids J Leukoc Biol 81 2007 336 343
190. C. Börner, A. Bedini, V. Höllt, and J. Kraus Analysis of promoter regions regulating basal and interleukin-4-inducible expression of the human CB1 receptor gene in T lymphocytes Mol Pharmacol 73 2008 1013 1019
191. D.-Z. Liu, C.-M. Hu, C.-H. Huang, S.-P. Wey, and T.-R. Jan Cannabidiol attenuates delayed-type hypersensitivity reactions via suppressing T-cell and macrophage reactivity Acta Pharmacol Sin 31 2010 1611 1617
192. G.J.M. Maestroni The endogenous cannabinoid 2-arachidonoyl glycerol as in vivo chemoattractant for dendritic cells and adjuvant for Th1 response to a soluble protein FASEB J 18 2004 1914 1916
193. A. Ribeiro, V. Ferraz-de-Paula, M.L. Pinheiro, M. Sakai, F.A. Costa-Pinto, and J. Palermo-Neto Anandamide prior to sensitization increases cell-mediated immunity in mice Int Immunopharmacol 10 2010 431 439
194. K. Sugawara, T. Bíró, D. Tsuruta, B.I. Tóth, A. Kromminga, and N. Zákány Endocannabinoids limit excessive mast cell maturation and activation in human skin J Allergy Clin Immunol 129 2012 726 738
195. M. Gokoh, S. Kishimoto, S. Oka, and T. Sugiura 2-Arachidonoylglycerol enhances the phagocytosis of opsonized zymosan by HL-60 cells differentiated into macrophage-like cells Biol Pharm Bull 30 2007 1199 1205
196. V.A. Fadok, D.L. Bratton, A. Konowal, P.W. Freed, J.Y. Westcott, and P.M. Henson Macrophages that have ingested apoptotic cells in vitro inhibit proinflammatory cytokine production through autocrine/paracrine mechanisms involving TGF-β, PGE2, and PAF J Clin Investig 101 1998 890 898
197. K.H. Han, S. Lim, J. Ryu, C.-W. Lee, Y. Kim, and J.-H. Kang CB1 and CB2 cannabinoid receptors differentially regulate the production of reactive oxygen species by macrophages Cardiovasc Res 84 2009 378 386
198. A. Sindrilaru, T. Peters, S. Wieschalka, C. Baican, A. Baican, and H. Peter An unrestrained proinflammatory M1 macrophage population induced by iron impairs wound healing in humans and mice J Clin Invest 121 2011 985 997
199. T. Tanikawa, K. Kurohane, and Y. Imai Regulatory effect of cannabinoid receptor agonist on chemokine-induced lymphocyte chemotaxis Biol Pharm Bull 34 2011 1090 1093
200. A. Nagel, M. Hertl, and R. Eming B-cell-directed therapy for inflammatory skin diseases J Invest Dermatol 129 2009 289 301
201. A.H. Merrill Sphingolipid and glycosphingolipid metabolic pathways in the era of sphingolipidomics Chem Rev 111 2011 6387 6422
202. J.T. Hannich, K. Umebayashi, and H. Riezman Distribution and functions of sterols and sphingolipids Cold Spring Harbor Perspect Biol 3 2011
203. S.T. Pruett, A. Bushnev, K. Hagedorn, M. Adiga, C.A. Haynes, and M.C. Sullards Thematic review series: sphingolipids. Biodiversity of sphingoid bases ("sphingosines") and related amino alcohols J Lipid Res 49 2008 1621 1639
204. K. Mizukoshi, K. Matsumoto, R. Hirose, T. Fujita, A. Ishida-Yamamoto, and H. Iizuka Effects of serine palmitoyltransferase inhibitor ISP-I on the stratum corneum of intact mouse skin Biol Pharm Bull 34 2011 1383 1389
205. G. Fabrias, J. Muñoz-Olaya, F. Cingolani, P. Signorelli, J. Casas, and V. Gagliostro Dihydroceramide desaturase and dihydrosphingolipids: debutant players in the sphingolipid arena Prog Lipid Res 51 2012 82 94
206. Y. Mizutani, S. Mitsutake, K. Tsuji, A. Kihara, and Y. Igarashi Ceramide biosynthesis in keratinocyte and its role in skin function Biochimie 91 2009 784 790
207. Y. Masukawa, H. Narita, E. Shimizu, N. Kondo, Y. Sugai, and T. Oba Characterization of overall ceramide species in human stratum corneum J Lipid Res 49 2008 1466 1476
208. C.E. Chalfant, and S. Spiegel Sphingosine 1-phosphate and ceramide 1-phosphate: expanding roles in cell signaling J Cell Sci 118 2005 4605 4612
209. W.M. Holleran, Y. Takagi, and Y. Uchida Epidermal sphingolipids: metabolism, function, and roles in skin disorders FEBS Lett 580 2006 5456 5466
210. J. Stiban, L. Caputo, and M. Colombini Ceramide synthesis in the endoplasmic reticulum can permeabilize mitochondria to proapoptotic proteins J Lipid Res 49 2008 625 634
211. A.B.A. Shakor, M. Taniguchi, K. Kitatani, M. Hashimoto, S. Asano, and A. Hayashi Sphingomyelin synthase 1-generated sphingomyelin plays an important role in transferrin trafficking and cell proliferation J Biol Chem 286 2011 36053 36062
212. A.V. Samsonov, I. Mihalyov, and F.S. Cohen Characterization of cholesterol-sphingomyelin domains and their dynamics in bilayer membranes Biophys J 81 2001 1486 1500
213. S. Kim, I. Hong, J.S. Hwang, J.K. Choi, H.S. Rho, and D.H. Kim Phytosphingosine stimulates the differentiation of human keratinocytes and inhibits TPA-induced inflammatory epidermal hyperplasia in hairless mouse skin Mol Med 12 2006 17 24
214. D.-S. Kim, S.-Y. Kim, B. Kleuser, M. Schäfer-Korting, K.-H. Kim, and K.-C. Park Sphingosine-1-phosphate inhibits human keratinocyte proliferation via Akt/protein kinase B inactivation Cell Signal 16 2004 89 95
215. 2 receptor subtype J Invest Dermatol 128 2008 1747 1756
216. M. Scherer, K. Leuthäuser-Jaschinski, J. Ecker, G. Schmitz, and G. Liebisch A rapid and quantitative LC-MS/MS method to profile sphingolipids J Lipid Res 51 2010 2001 2011
217. M. Jung, S. Lee, H.-Y. Park, J.-K. Youm, S. Jeong, and J. Bae Anti-ageing effects of a new synthetic sphingolipid (K6EAA-L12) on aged murine skin Exp Dermatol 20 2011 314 319
218. S. Bu, Y. Asano, A. Bujor, K. Highland, F. Hant, and M. Trojanowska Dihydrosphingosine 1-phosphate has a potent antifibrotic effect in scleroderma fibroblasts via normalization of phosphatase and tensin homolog levels Arthritis Rheum 62 2010 2117 2126
219. I. Reines, M. Kietzmann, R. Mischke, T. Tschernig, A. Luth, and B. Kleuser Topical application of sphingosine-1-phosphate and FTY720 attenuate allergic contact dermatitis reaction through inhibition of dendritic cell migration J Invest Dermatol 129 2009 1954 1962
220. Y.Y. Lan, D. Tokita, Z. Wang, H.C. Wang, J. Zhan, and V. Brinkmann Sphingosine 1-phosphate receptor agonism impairs skin dendritic cell migration and homing to secondary lymphoid tissue: association with prolonged allograft survival Transpl Immunol 20 2008 88 94
221. G. Gollmann, H. Neuwirt, C.H. Tripp, H. Mueller, G. Konwalinka, and C. Heufler Sphingosine-1-phosphate receptor type-1 agonism impairs blood dendritic cell chemotaxis and skin dendritic cell migration to lymph nodes under inflammatory conditions Int Immunol 20 2008 911 923
222. A. Lamana, P. Martin, H. de la Fuente, L. Martinez-Munoz, A. Cruz-Adalia, and M. Ramirez-Huesca CD69 modulates sphingosine-1-phosphate-induced migration of skin dendritic cells J Invest Dermatol 131 2011 1503 1512
223. H. Müller, S. Hofer, N. Kaneider, H. Neuwirt, B. Mosheimer, and G. Mayer The immunomodulator FTY720 interferes with effector functions of human monocyte-derived dendritic cells Eur J Immunol 35 2005 533 545
224. H17-cell differentiation in a murine model FASEB J 25 2011 4024 4036
225. L. Zhi, P. Kim, B.D. Thompson, C. Pitsillides, A.J. Bankovich, and S.-H. Yun FTY720 blocks egress of T cells in part by abrogation of their adhesion on the lymph node sinus J Immunol 187 2011 2244 2251
226. A. Olivera Unraveling the complexities of sphingosine-1-phosphate function: the mast cell model Prostaglandins Other Lipid Mediat 86 2008 1 11
227. S.C. Diesner, A. Olivera, S. Dillahunt, C. Schultz, T. Watzlawek, and E. Förster-Waldl Sphingosine-kinase 1 and 2 contribute to oral sensitization and effector phase in a mouse model of food allergy Immunol Lett 141 2012 210 219
228. R.T. Van Dross Metabolism of anandamide by COX-2 is necessary for endocannabinoid-induced cell death in tumorigenic keratinocytes Mol Carcinog 48 2009 724 732
229. 2 J Lipid Res 46 2005 2745 2751
230. J.S. Moody, K.R. Kozak, C. Ji, and L.J. Marnett Selective oxygenation of the endocannabinoid 2-arachidonylglycerol by leukocyte-type 12-lipoxygenase Biochemistry (Mosc) 40 2001 861 866
231. K.R. Kozak, R.A. Gupta, J.S. Moody, C. Ji, W.E. Boeglin, and R.N. DuBois 15-Lipoxygenase metabolism of 2-arachidonylglycerol J Biol Chem 277 2002 23278 23286
232. N.T. Snider, A.M. Kornilov, U.M. Kent, and P.F. Hollenberg Anandamide metabolism by human liver and kidney microsomal cytochrome P450 enzymes to form hydroxyeicosatetraenoic and epoxyeicosatrienoic acid ethanolamides J Pharmacol Exp Ther 321 2007 590 597
233. H. Du, X. Chen, J. Zhang, and C. Chen Inhibition of COX-2 expression by endocannabinoid 2-arachidonoylglycerol is mediated via PPAR-γ Br J Pharmacol 163 2011 1533 1549
234. 1 cannabinoid receptor Mol Pharmacol 70 2006 41 50
235. J.D. Wilkinson, and E.M. Williamson Cannabinoids inhibit human keratinocyte proliferation through a non-CB1/CB2 mechanism and have a potential therapeutic value in the treatment of psoriasis J Dermatol Sci 45 2007 87 92
236. 2 production in response to TNF-α FASEB J 17 2003 1411 1421
237. 2 J Biol Chem 279 2004 11320 11326
238. H. Nakamura, T. Hirabayashi, M. Shimizu, and T. Murayama Ceramide-1-phosphate activates cytosolic phospholipase A2α directly and by PKC pathway Biochem Pharmacol 71 2006 850 857
239. 2 via a novel site in the C2 domain J Biol Chem 282 2007 20467 20474
240. 2 and prostaglandin synthesis J Biol Chem 284 2009 26897 26907
241. H. Nakamura, S. Wakita, A. Suganami, Y. Tamura, K. Hanada, and T. Murayama Modulation of the activity of cytosolic phospholipase A2α (cPLA2α) by cellular sphingolipids and inhibition of cPLA2α by sphingomyelin J Lipid Res 51 2010 720 728
242. M.A. Lowes, A.M. Bowcock, and J.G. Krueger Pathogenesis and therapy of psoriasis Nature 445 2007 866 873
243. + T cells J Invest Dermatol 132 2012 626 634
244. A. Pietrzak, A. Michalak-Stoma, G. Chodorowska, and J.C. Szepietowski Lipid disturbances in psoriasis: an update Mediators Inflamm 2010 2010
245. 2α in epidermis of psoriasis Proc Natl Acad Sci USA 72 1975 5130 5134
246. P. Mayser, H. Grimm, and F. Grimminger n-3 fatty acids in psoriasis Br J Nutr 87 Suppl. 1 2002 S77 S82
247. J.R. Ricketts, M.J. Rothe, and J.M. Grant-Kels Nutrition and psoriasis Clin Dermatol 28 2010 615 626
248. 2 in human keratinocytes and in healthy and psoriatic human skin J Invest Dermatol 124 2004 204 211
249. 2 in psoriatic tissue Inflammation 18 1994 1 12
250. G.J. Fisher, H.S. Talwar, A. Tavakkol, J. Esmann, J.J. Baldassare, and J.T. Elder Phosphoinositide-mediated signal transduction in normal and psoriatic epidermis J Invest Dermatol 95 1990 15S-7S
251. J.E. Gudjonsson, J. Ding, X. Li, R.P. Nair, T. Tejasvi, and Z.S. Qin Global gene expression analysis reveals evidence for decreased lipid biosynthesis and increased innate immunity in uninvolved psoriatic skin J Invest Dermatol 129 2009 2795 2804
252. K. Kragballe, L. Desjarlais, E.A. Duell, and J.J. Voorhees In vitro synthesis of 12-hydroxy-eicosatetraenoic acid is increased in uninvolved psoriatic epidermis J Invest Dermatol 87 1986 47 52
253. W.E. Boeglin, R.B. Kim, and A.R. Brash A 12R-lipoxygenase in human skin: mechanistic evidence, molecular cloning, and expression Proc Natl Acad Sci USA 95 1998 6744 6749
254. Q. Zhou, U. Mrowietz, and M. Rostami-Yazdi Oxidative stress in the pathogenesis of psoriasis Free Radic Biol Med 47 2009 891 905
255. A.W. Ford-Hutchinson 5-Lipoxygenase activation in psoriasis: a dead issue? Skin Pharmacol 6 1993 292 297
256. G.J. Fisher, H.S. Talwar, J.J. Baldassare, P.A. Henderson, and J.J. Voorhees Increased phospholipase C-catalyzed hydrolysis of phosphatidylinositol- 4,5-bisphosphate and 1,2-sn-diacylglycerol content in psoriatic involved compared to uninvolved and normal epidermis J Invest Dermatol 95 1990 428 435
257. L. Nanney, R. Gates, G. Todderud, L. King Jr, and G. Carpenter Altered distribution of phospholipase C-gamma 1 in benign hyperproliferative epidermal diseases Cell Growth Differ 3 1992 233 239
258. B.-L. Lew, Y. Cho, J. Kim, W.-Y. Sim, and N.-I. Kim Ceramides and cell signaling molecules in psoriatic epidermis: reduced levels of ceramides, PKC-α, and JNK J Korean Med Sci 21 2006 95 99
259. K.-K. Hong, H.-R. Cho, W.-C. Ju, Y. Cho, and N.-I. Kim A study on altered expression of serine palmitoyltransferase and ceramidase in psoriatic skin lesion J Korean Med Sci 22 2007 862 867
260. E.-Y. Seo, G.T. Park, K.-M. Lee, J.-A. Kim, J.-H. Lee, and J.-M. Yang Identification of the target genes of atopic dermatitis by real-time PCR J Invest Dermatol 126 2006 1187 1189
261. D.-D. Lee, O. Stojadinovic, A. Krzyzanowska, C. Vouthounis, M. Blumenberg, and M. Tomic-Canic Retinoid-responsive transcriptional changes in epidermal keratinocytes J Cell Physiol 220 2009 427 439
262. 2+ signaling J Invest Dermatol 128 2008 2166 2178
263. M.K. Oyoshi, R. He, L. Kumar, J. Yoon, and R.S. Geha Cellular and molecular mechanisms in atopic dermatitis Adv Immunol 102 2009 135 226
264. A. Kawamura, K. Ooyama, K. Kojima, H. Kachi, T. Abe, and K. Amano Dietary supplementation of gamma-linolenic acid improves skin parameters in subjects with dry skin and mild atopic dermatitis J Oleo Sci 60 2011 597 607
265. A. Gimenez-Arnau, C. Barranco, M. Alberola, C. Wale, S. Serrano, and M.R. Buchanan Effects of linoleic acid supplements on atopic dermatitis Adv Exp Med Biol 433 1997 285 289
266. C. Koch, S. Dölle, M. Metzger, C. Rasche, H. Jungclas, and R. Rühl Docosahexaenoic acid (DHA) supplementation in atopic eczema: a randomized, double-blind, controlled trial Br J Dermatol 158 2008 786 792
267. F.J. Bath-Hextall, C. Jenkinson, R. Humphreys, and H.C. Williams Dietary supplements for established atopic eczema Cochrane Database Syst Rev 2 2012 CD005205
268. T. Ruzicka, T. Simmet, B.A. Peskar, and J. Ring Skin levels of arachidonic acid-derived inflammatory mediators and histamine in atopic dermatitis and psoriasis J Invest Dermatol 86 1986 105 108
269. 2 receptor CRTH2 is important for allergic skin inflammation after epicutaneous antigen challenge J Allergy Clin Immunol 126 2010 784 790
270. S.A. Boehme, E.P. Chen, K. Franz-Bacon, R. Šášik, L.J. Sprague, and T.W. Ly Antagonism of CRTH2 ameliorates chronic epicutaneous sensitization-induced inflammation by multiple mechanisms Int Immunol 21 2009 1 17
271. H. Yahara, T. Satoh, C. Miyagishi, and H. Yokozeki Increased expression of CRTH2 on eosinophils in allergic skin diseases J Eur Acad Dermatol Venereol 24 2010 75 76
272. Z. Hua, H. Fei, and X. Mingming Evaluation and interference of serum and skin lesion levels of leukotrienes in patients with eczema Prostaglandins Leukot Essent Fatty Acids 75 2006 51 55
273. P. Rubin, and K.W. Mollison Pharmacotherapy of diseases mediated by 5-lipoxygenase pathway eicosanoids Prostaglandins Other Lipid Mediat 83 2007 188 197
274. V. Broshtilova, and M. Gantcheva Therapeutic hotline: cysteinyl leukotriene receptor antagonist montelukast in the treatment of atopic dermatitis Dermatol Ther 23 2010 90 93
275. J.H. Jin, T.M. Ngoc, K. Bae, Y.S. Kim, and H.P. Kim Inhibition of experimental atopic dermatitis by rhubarb (rhizomes of Rheum tanguticum) and 5-lipoxygenase inhibition of its major constituent, emodin Phytother Res 25 2011 755 759
276. D. De Filippis, A. D'Amico, and T. Iuvone Cannabinomimetic control of mast cell mediator release: new perspective in chronic inflammation J Neuroendocrinol 20 2008 20 25
277. N. Pulvirenti, M.R. Nasca, and G. Micali Topical adelmidrol 2% emulsion, a novel aliamide, in the treatment of mild atopic dermatitis in pediatric subjects: a pilot study Acta Dermatovenerol Croat 15 2007 80 83
278. 2 and TNFα release from canine skin mast cells Vet Immunol Immunopathol 133 2010 9 15
279. J.E. Schlosburg, D.L. Boger, B.F. Cravatt, and A.H. Lichtman Endocannabinoid modulation of scratching response in an acute allergenic model: a new prospective neural therapeutic target for pruritus J Pharmacol Exp Ther 329 2009 314 323
280. J. Ishikawa, H. Narita, N. Kondo, M. Hotta, Y. Takagi, and Y. Masukawa Changes in the ceramide profile of atopic dermatitis patients J Invest Dermatol 130 2010 2511 2514
281. M. Janssens, J. van Smeden, G.S. Gooris, W. Bras, G. Portale, and P.J. Caspers Lamellar lipid organization and ceramide composition in the stratum corneum of patients with atopic eczema J Invest Dermatol 131 2011 2136 2138
282. J.M. Jungersted, H. Scheer, M. Mempel, H. Baurecht, L. Cifuentes, and J.K. Høgh Stratum corneum lipids, skin barrier function and filaggrin mutations in patients with atopic eczema Allergy 65 2010 911 918
283. L.H. Kircik, J.Q. Del Rosso, and D. Aversa Evaluating clinical use of a ceramide-dominant, physiologic lipid-based topical emulsion for atopic dermatitis J Clin Aesthetic Dermatol 4 2011 34 40
284. L.H. Kircik, and J.Q. Del Rosso Nonsteroidal treatment of atopic dermatitis in pediatric patients with a ceramide-dominant topical emulsion formulated with an optimized ratio of physiological lipids J Clin Aesthetic Dermatol 4 2011 25 31
285. K. Vávrová, A. Hrabálek, S. Mac-Mary, P. Humbert, and P. Muret Ceramide analogue 14S24 selectively recovers perturbed human skin barrier Br J Dermatol 157 2007 704 712
286. K. Sugita, K. Kabashima, J.-I. Sakabe, R. Yoshiki, H. Tanizaki, and Y. Tokura FTY720 regulates bone marrow egress of eosinophils and modulates late-phase skin reaction in mice Am J Pathol 177 2010 1881 1887
287. K. Katagiri, S. Arakawa, and R. Kurahashi IL-4 restores impaired contact hypersensitivity response in obese mice fed a high-fat diet enriched with oleic acid J Invest Dermatol 128 2007 735 737
288. S. Sierra, F. Lara-Villoslada, M. Comalada, M. Olivares, and J. Xaus Dietary fish oil n-3 fatty acids increase regulatory cytokine production and exert anti-inflammatory effects in two murine models of inflammation Lipids 41 2006 1115 1125
289. 2 inhibitor: a double-blind placebo-controlled pilot study Int J Immunopathol Pharmacol 20 2007 191 195
290. 2-IP signaling promotes Th1 differentiation in a mouse model of contact hypersensitivity J Immunol 184 2010 5595 5603
291. A. Del Bufalo, J. Bernad, C. Dardenne, D. Verda, J.R. Meunier, and F. Rousset Contact sensitizers modulate the arachidonic acid metabolism of PMA-differentiated U-937 monocytic cells activated by LPS Toxicol Appl Pharmacol 256 2011 35 43
292. W. Bäumer, S. Krekeler, V.C. DeVries, F. Niedorf, T. Tschernig, and M. Kietzmann Non-steroidal and steroidal anti-inflammatory drugs vary in their modulation of dendritic cell function in the elicitation phase of allergic contact dermatitis Exp Dermatol 15 2006 322 329
293. 3 signaling suppresses skin inflammation in murine contact hypersensitivity J Allergy Clin Immunol 124 809-818 2009 e2
294. M. Karsak, E. Gaffal, R. Date, L. Wang-Eckhardt, J. Rehnelt, and S. Petrosino Attenuation of allergic contact dermatitis through the endocannabinoid system Science 316 2007 1494 1497
295. C.W. Choi, J.W. Choi, K.C. Park, and S.W. Youn Facial sebum affects the development of acne, especially the distribution of inflammatory acne J Eur Acad Dermatol Venereol 2011 http://dx.doi.org/10.1111/j.1468-3083.2011.04384x.
296. A.M. Morello, D.T. Downing, and J.S. Strauss Octadecadienoic acids in the skin surface lipids of acne patients and normal subjects J Invest Dermatol 66 1976 319 323
297. P. Morganti, E. Berardesca, B. Guarneri, F. Guarneri, G. Fabrizi, and P. Palombo Topical clindamycin 1% vs. linoleic acid-rich phosphatidylcholine and nicotinamide 4% in the treatment of acne: a multicentre-randomized trial Int J Cosmet Sci 33 2011 467 476
298. H. Akamatsu, J. Komura, Y. Miyachi, Y. Asada, and Y. Niwa Suppressive effects of linoleic acid on neutrophil oxygen metabolism and phagocytosis J Invest Dermatol 95 1990 271 274
299. C. Letawe, M. Boone, and G.E. Pierard Digital image analysis of the effect of topically applied linoleic acid on acne microcomedones Clin Exp Dermatol 23 1998 56 58
300. Y. Katsuta, T. Iida, S. Inomata, and M. Denda Unsaturated fatty acids induce calcium influx into keratinocytes and cause abnormal differentiation of epidermis J Invest Dermatol 124 2005 1008 1013
301. M. Ottaviani, T. Alestas, E. Flori, A. Mastrofrancesco, C.C. Zouboulis, and M. Picardo Peroxidated squalene induces the production of inflammatory mediators in HaCaT keratinocytes: a possible role in acne vulgaris J Invest Dermatol 126 2006 2430 2437
302. C.C. Zouboulis, H. Seltmann, and T. Alestas Zileuton prevents the activation of the leukotriene pathway and reduces sebaceous lipogenesis Exp Dermatol 19 2010 148 150
303. T. Sato, T. Shirane, N. Noguchi, M. Sasatsu, and A. Ito Novel anti-acne actions of nadifloxacin and clindamycin that inhibit the production of sebum, prostaglandin E2 and promatrix metalloproteinase-2 in hamster sebocytes J Dermatol 39 2012 774 800
304. B.I. Toth, T. Geczy, Z. Griger, A. Dozsa, H. Seltmann, and L. Kovacs Transient receptor potential vanilloid-1 signaling as a regulator of human sebocyte biology J Invest Dermatol 129 2008 329 339
305. P.W. Wertz, M.C. Miethke, S.A. Long, J.S. Strauss, and D.T. Downing The composition of the ceramides from human stratum corneum and from comedones J Invest Dermatol 84 1985 410 412
306. T. Pavicic, U. Wollenweber, M. Farwick, and H.C. Korting Anti-microbial and -inflammatory activity and efficacy of phytosphingosine: an in vitro and in vivo study addressing acne vulgaris Int J Cosmet Sci 29 2007 181 190
307. M. Otranto, A.P. Do Nascimento, and A. Monte-Alto-Costa Effects of supplementation with different edible oils on cutaneous wound healing Wound Repair Regen 18 2010 629 636
308. J.C. McDaniel, K. Massey, and A. Nicolaou Fish oil supplementation alters levels of lipid mediators of inflammation in microenvironment of acute human wounds Wound Repair Regen 19 2011 189 200
309. H.G. Rodrigues, M.A.R. Vinolo, J. Magdalon, K. Vitzel, R.T. Nachbar, and A.F.M. Pessoa Oral administration of oleic or linoleic acid accelerates the inflammatory phase of wound healing J Invest Dermatol 132 2012 208 215
310. Y. Lu, H. Tian, and S. Hong Novel 14,21-dihydroxy-docosahexaenoic acids: structures, formation pathways, and enhancement of wound healing J Lipid Res 51 2010 923 932
311. N.Y. Park, G. Valacchi, and Y. Lim Effect of dietary conjugated linoleic acid supplementation on early inflammatory responses during cutaneous wound healing Mediators Inflamm 2010 2010
312. H. Kampfer, L. Brautigam, G. Geisslinger, J. Pfeilschifter, and S. Frank Cyclooxygenase-1-coupled prostaglandin biosynthesis constitutes an essential prerequisite for skin repair J Invest Dermatol 120 2003 880 890
313. H. Kobayashi, O. Katakura, N. Morimoto, K. Akiyoshi, and S. Kasugai Effects of cholesterol-bearing pullulan (CHP)-nanogels in combination with prostaglandin E1 on wound healing J Biomed Mater Res B Appl Biomater 91B 2009 55 60
314. Y. Wu, S. Karna, C.H. Choi, M. Tong, H.-H. Tai, and D.H. Na Synthesis and biological evaluation of novel thiazolidinedione analogues as 15-hydroxyprostaglandin dehydrogenase inhibitors J Med Chem 54 2011 5260 5264
315. R.M.Z. Farahani Endocannabinoid system and wound healing J Tissue Viability 17 2008 100 101
316. S. Kozono, T. Matsuyama, K.K. Biwasa, K.-I. Kawahara, Y. Nakajima, and T. Yoshimoto Involvement of the endocannabinoid system in periodontal healing Biochem Biophys Res Commun 394 2010 928 933
317. M. Solinas, P. Massi, A.R. Cantelmo, M.G. Cattaneo, R. Cammarota, and D. Bartolini Cannabidiol inhibits angiogenesis by multiple mechanisms Br J Pharmacol 167 2012 1218 1231
318. K.R. Watterson, D.A. Lanning, R.F. Diegelmann, and S. Spiegel Regulation of fibroblast functions by lysophospholipid mediators: Potential roles in wound healing Wound Repair Regen 15 2007 607 616
319. K.N. Francis-Goforth, A.H. Harken, and J.D. Saba Normalization of diabetic wound healing Surgery 147 2010 446 449
320. T. Ulrych, A. BÖHm, A. Polzin, G. Daum, R.M. NÜSing, and G. Geisslinger Release of sphingosine-1-phosphate from human platelets is dependent on thromboxane formation J Thromb Haemost 9 2011 790 798
321. H. Wakita, K. Matsushita, K. Nishimura, Y. Tokura, F. Furukawa, and M. Takigawa Sphingosylphosphorylcholine stimulates proliferation and upregulates cell surface-associated plasminogen activator activity in cultured human keratinocytes J Invest Dermatol 110 1998 253 258
322. M.J. Zhu, C.D. Kim, Y.B. Kwon, K.-C. Kye, Y.Y. Chen, and W.-H. Lee Induction of connective tissue growth factor expression by sphingosylphosphorylcholine in cultured human skin fibroblasts Exp Dermatol 14 2005 509 514
323. K.-C. Kye, E.-K. Chae, Y.-J. Piao, S. Park, J.-K. Park, and C.D. Kim Signaling events during induction of plasminogen activator inhibitor-1 expression by sphingosylphosphorylcholine in cultured human dermal fibroblasts J Invest Dermatol 122 2004 1365 1371
324. Y.B. Kwon, Y.S. Lee, K.C. Sohn, Y.J. Piao, S.J. Back, and Y.J. Seo Sphingosylphosphorylcholine-induced interleukin-6 production is mediated by protein kinase C and p42/44 extracellular signal-regulated kinase in human dermal fibroblasts J Dermatol Sci 46 2007 91 99
325. A. Nicolaou, S.M. Pilkington, and L.E. Rhodes Ultraviolet-radiation induced skin inflammation: dissecting the role of bioactive lipids Chem Phys Lipids 164 2011 535 543
326. G.M. Halliday, D.L. Damian, S. Rana, and S.N. Byrne The suppressive effects of ultraviolet radiation on immunity in the skin and internal organs: implications for autoimmunity J Dermatol Sci 66 2012 176 182
327. K.Y. Chin, B. El-Kayat, A. Milne, and A. Hart Melanoma diagnosed 27 years after a benoxaprofen-induced photosensitivity reaction J Dermatol Case Rep 6 2012 5 7
328. K. Shimoda, N. Wagai, and M. Kato Stimulation of prostaglandin production by quinolone phototoxicity in Balb/c 3T3 mouse fibroblast cells in vitro Fundam Appl Toxicol 36 1997 157 162
329. D.L. Narayanan, R.N. Saladi, and J.L. Fox Review: ultraviolet radiation and skin cancer Int J Dermatol 49 2010 978 986
330. 2 levels in skin and increases the threshold to provocation of polymorphic light eruption J Invest Dermatol 105 1995 532 535
331. L.E. Rhodes, H. Shahbakhti, R.M. Azurdia, R.M.W. Moison, M.-J.S.T. Steenwinkel, and M.I. Homburg Effect of eicosapentaenoic acid, an omega-3 polyunsaturated fatty acid, on UVR-related cancer risk in humans. An assessment
332. A. Storey, F. McArdle, P.S. Friedmann, M.J. Jackson, and L.E. Rhodes Eicosapentaenoic acid and docosahexaenoic acid reduce UVB- and TNF-alpha-induced IL-8 secretion in keratinocytes and UVB-induced IL-8 in fibroblasts J Invest Dermatol 124 2005 248 255
333. R.M.W. Moison, D.P.T. Steenvoorden, and G.M.J. Beijersbergen van Henegouwen Topically applied eicosapentaenoic acid protects against local immunosuppression Induced by UVB irradiation, cis-urocanic acid and thymidine dinucleotides Photochem Photobiol 73 2001 64 70
334. M. Cario-André, S. Briganti, M. Picardo, O. Nikaido, H. De Verneuil, and A. Taïeb Polyunsaturated fatty acids partially reproduce the role of melanocytes in the epidermal melanin unit Exp Dermatol 14 2005 194 201
335. H.H. Kim, S. Cho, S. Lee, K.H. Kim, K.H. Cho, and H.C. Eun Photoprotective and anti-skin-aging effects of eicosapentaenoic acid in human skin in vivo J Lipid Res 47 2006 921 930
336. 2 in human skin Am J Physiol-Cell Physiol 270 1996 C1037 C1050
337. 2 after UVB injury Biochim Biophys Acta (BBA)-Lipids Lipid Metab 1299 1996 23 33
338. C.H. Kang-Rotondo, C.C. Miller, A.R. Morrison, and A.P. Pentland Enhanced keratinocyte prostaglandin synthesis after UV injury is due to increased phospholipase activity Am J Physiol-Cell Physiol 264 1993 C396 C401
339. W. Chen, Q. Tang, M.S. Gonzales, and G.T. Bowden Role of p38 MAP kinases and ERK in mediating ultraviolet-B induced cyclooxygenase-2 gene expression in human keratinocytes Oncogene 20 2001 3921 3926
340. Y. Shintani, Y. Yasuda, K. Kobayashi, A. Maeda, and A. Morita Narrowband ultraviolet B radiation suppresses contact hypersensitivity Photodermatol Photoimmunol Photomed 24 2008 32 37
341. C.J. Carsberg, J. Ohanian, and P.S. Friedmann Ultraviolet radiation stimulates a biphasic pattern of 1,2-diacylglycerol formation in cultured human melanocytes and keratinocytes by activation of phospholipases C and D Biochem J 305 Pt 2 1995 471 477
342. D. Zheng, A.M. Bode, Q. Zhao, Y.-Y. Cho, F. Zhu, and W.-Y. Ma The cannabinoid receptors are required for ultraviolet-induced inflammation and skin cancer development Cancer Res 68 2008 3992 3998
343. J.M. Jungersted, J.K. Høgh, L.I. Hellgren, G.B.E. Jemec, and T. Agner The impact of ultraviolet therapy on stratum corneum ceramides and barrier function Photodermatol Photoimmunol Photomed 27 2011 331 333
344. Y. Uchida, E. Houben, K. Park, S. Douangpanya, Y.-M. Lee, and B.X. Wu Hydrolytic pathway protects against ceramide-induced apoptosis in keratinocytes exposed to UVB J Invest Dermatol 130 2010 2472 2480
345. H. Bak, S.-P. Hong, S.-K. Jeong, E.-H. Choi, S.E. Lee, and S.-H. Lee Altered epidermal lipid layers induced by long-term exposure to suberythemal-dose ultraviolet Int J Dermatol 50 2011 832 837