Ginger phenylpropanoids inhibit IL-1β and prostanoid secretion and disrupt arachidonate-phospholipid remodeling by targeting phospholipases A 2

Journal of Immunology

Volumn 187, Issue 8, 2011, Pages 4140-4150

  Nievergelt, Andreas ^a   Marazzi, Janine ^a   Schoop, Roland ^b   Altmann, Karl Heinz ^c   Gertsch, Jürg ^a  

^a UNIVERSITY OF BERN   (Switzerland)

^b Bioforce AG   (Switzerland)

^c ETH ZURICH   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

(10) GINGEROL; (10) SHOGAOL; 1,4 DIAMINO 1,4 BIS(2 AMINOPHENYLTHIO) 2,3 DICYANOBUTADIENE; 2 (2 AMINO 3 METHOXYPHENYL)CHROMONE; 4 (4 FLUOROPHENYL) 2 (4 HYDROXYPHENYL) 5 (4 PYRIDYL)IMIDAZOLE; 4 (4 FLUOROPHENYL) 2 (4 METHYLSULFINYLPHENYL) 5 (4 PYRIDYL)IMIDAZOLE; ANTHRA[1,9 CD]PYRAZOL 6(2H) ONE; ARACHIDONIC ACID; BROMOENOL LACTONE; CD3 ANTIBODY; CETIRIZINE; CYCLOSPORIN; DEXAMETHASONE; DICLOFENAC; GINGER EXTRACT; INTERLEUKIN 1BETA; LEUKOTRIENE B4; LIPOPOLYSACCHARIDE; PARTHENOLIDE; PHENYLPROPANOID; PHOSPHOLIPASE A2; PROSTAGLANDIN E2; PROSTANOID; SHOGAOL; THAPSIGARGIN; THROMBOXANE B2; UNCLASSIFIED DRUG;

ACYLATION; ANTIINFLAMMATORY ACTIVITY; ARTICLE; CONTROLLED STUDY; DEACYLATION; DRUG DETERMINATION; DRUG INHIBITION; DRUG STRUCTURE; ENZYME RELEASE; HUMAN; HUMAN CELL; MACROPHAGE; MONOCYTE; PRIORITY JOURNAL; PROTEIN EXPRESSION; PROTEIN FUNCTION; PROTEIN TARGETING; TREATMENT RESPONSE;

ARACHIDONIC ACID; BLOTTING, WESTERN; CELLS, CULTURED; CYTOKINES; EICOSANOIDS; ENZYME-LINKED IMMUNOSORBENT ASSAY; GINGER; HUMANS; INTERLEUKIN-1BETA; MONOCYTES; PHOSPHOLIPASES A2; PHOSPHOLIPIDS; PLANT EXTRACTS; RHIZOME; U937 CELLS;

EID: 80054769765     PISSN: 00221767     EISSN: 15506606     Source Type: Journal    
DOI: 10.4049/jimmunol.1100880     Document Type: Article

References (98)

1. Duke, J. A., and E. S. Ayensu. 1985. Medicinal Plants of China. Reference Publications, Algonac, MI.
2. Boone, S. A., and K. M. Shields. 2005. Treating pregnancy-related nausea and vomiting with ginger. Ann. Pharmacother. 39: 1710-1713. (Pubitemid 41393131)
3. Bryer, E. 2005. A literature review of the effectiveness of ginger in alleviating mild-to-moderate nausea and vomiting of pregnancy. J. Midwifery Womens Health 50: e1-e3. (Pubitemid 40103893)
4. Altman, R. D., and K. C. Marcussen. 2001. Effects of a ginger extract on knee pain in patients with osteoarthritis. Arthritis Rheum. 44: 2531-2538. (Pubitemid 33049331)
5. Bliddal, H., A. Rosetzsky, P. Schlichting, M. S. Weidner, L. A. Andersen, H. H. Ibfelt, K. Christensen, O. N. Jensen, and J. Barslev. 2000. A randomized, placebo-controlled, cross-over study of ginger extracts and ibuprofen in osteoarthritis. Osteoarthritis Cartilage 8: 9-12. (Pubitemid 30032721)
6. Penna, S. C., M. V. Medeiros, F. S. Aimbire, H. C. Faria-Neto, J. A. Sertié, and R. A. Lopes-Martins. 2003. Anti-inflammatory effect of the hydralcoholic extract of Zingiber officinale rhizomes on rat paw and skin edema. Phytomedicine 10: 381-385. (Pubitemid 36745160)
7. Wigler, I., I. Grotto, D. Caspi, and M. Yaron. 2003. The effects of Zintona EC (a ginger extract) on symptomatic gonarthritis. Osteoarthritis Cartilage 11: 783-789. (Pubitemid 37407594)
8. Kim, J. K., Y. Kim, K. M. Na, Y. J. Surh, and T. Y. Kim. 2007. [6]-Gingerol prevents UVB-induced ROS production and COX-2 expression in vitro and in vivo. Free Radic. Res. 41: 603-614. (Pubitemid 46511125)
9. Lee, T. Y., K. C. Lee, S. Y. Chen, and H. H. Chang. 2009. 6-Gingerol inhibits ROS and iNOS through the suppression of PKC-alpha and NF-kappaB pathways in lipopolysaccharide-stimulated mouse macrophages. Biochem. Biophys. Res. Commun. 382: 134-139.
10. Nurtjahja-Tjendraputra, E., A. J. Ammit, B. D. Roufogalis, V. H. Tran, and C. C. Duke. 2003. Effective anti-platelet and COX-1 enzyme inhibitors from pungent constituents of ginger. Thromb. Res. 111: 259-265. (Pubitemid 38021945)
11. van Breemen, R. B., Y. Tao, and W. Li. 2011. Cyclooxygenase-2 inhibitors in ginger (Zingiber officinale). Fitoterapia 82: 38-43.
12. Heubl, G., G. Abel, W. Blaschek, and H. Hager. 1997. Hagers Handbuch der Pharmazeutischen Praxis. Springer, Berlin.
13. Aimbire, F., S. C. Penna, M. Rodrigues, K. C. Rodrigues, R. A. Lopes-Martins, and J. A. Sertié. 2007. Effect of hydroalcoholic extract of Zingiber officinalis rhizomes on LPS-induced rat airway hyperreactivity and lung inflammation. Prostaglandins Leukot. Essent. Fatty Acids 77: 129-138. (Pubitemid 350141684)
14. Denniff, P., I. Macleod, and D. A. Whiting. 1981. Syntheses of the (±)-[n]-gingerols (pungent principles of ginger) and related compounds through regio-selective aldol condensations: relative pungency assays. J.C.S. Perkin I: 82-87.
15. Iwasaki, Y., A. Morita, T. Iwasawa, K. Kobata, Y. Sekiwa, Y. Morimitsu, K. Kubota, and T. Watanabe. 2006. A nonpungent component of steamed ginger - [10]-shogaol - increases adrenaline secretion via the activation of TRPV1. Nutr. Neurosci. 9: 169-178. (Pubitemid 44869162)
16. Morita, A., Y. Iwasaki, K. Kobata, H. Yokogoshi, and T. Watanabe. 2007. Newly synthesized oleylgingerol and oleylshogaol activate TRPV1 ion channels. Biosci. Biotechnol. Biochem. 71: 2304-2307. (Pubitemid 350113118)
17. Nievergelt, A., P. Huonker, R. Schoop, K. H. Altmann, and J. Gertsch. 2010. Identification of serotonin 5-HT1A receptor partial agonists in ginger. Bioorg. Med. Chem. 18: 3345-3351.
18. Gilroy, D. W., J. Newson, P. Sawmynaden, D. A. Willoughby, and J. D. Croxtall. 2004. A novel role for phospholipase A2 isoforms in the checkpoint control of acute inflammation. FASEB J. 18: 489-498. (Pubitemid 38326305)
19. Amandi-Burgermeister, E., U. Tibes, B. M. Kaiser, W. G. Friebe, and W. V. Scheuer. 1997. Suppression of cytokine synthesis, integrin expression and chronic inflammation by inhibitors of cytosolic phospholipase A2. Eur. J. Pharmacol. 326: 237-250. (Pubitemid 27214554)
20. Honda, Z., M. Nakamura, I. Miki, M. Minami, T. Watanabe, Y. Seyama, H. Okado, H. Toh, K. Ito, T. Miyamoto, et al. 1991. Cloning by functional expression of platelet-activating factor receptor from guinea-pig lung. Nature 349: 342-346. (Pubitemid 21912080)
21. Caughey, G. E., M. J. James, and L. G. Cleland. 2005. Prostaglandins and leukotrienes. In Encyclopedia of Human Nutrition, 2nd Ed. B. Caballero, L. Allen, and A. Prentice, eds. Elsevier, Amsterdam, p. 42-45.
22. Smith, W. L., and R. C. Murphy. 2004. Prostaglandins and Leukotrienes. In Encyclopedia of Biological Chemistry. W. J. Lennarz and M. D. Lane, eds. Elsevier, Amsterdam, p. 452-456.
23. Lands, W. E. 1958. Metabolism of glycerolipides; a comparison of lecithin and triglyceride synthesis. J. Biol. Chem. 231: 883-888.
24. Lands, W. E. 1960. Metabolism of glycerolipids. 2. The enzymatic acylation of lysolecithin. J. Biol. Chem. 235: 2233-2237.
25. Balsinde, J., I. D. Bianco, E. J. Ackermann, K. Conde-Frieboes, and E. A. Dennis. 1995. Inhibition of calcium-independent phospholipase A2 prevents arachidonic acid incorporation and phospholipid remodeling in P388D1 macrophages. Proc. Natl. Acad. Sci. USA 92: 8527-8531.
26. Smani, T., S. I. Zakharov, E. Leno, P. Csutora, E. S. Trepakova, and V. M. Bolotina. 2003. Ca2+-independent phospholipase A2 is a novel determinant of store-operated Ca2+ entry. J. Biol. Chem. 278: 11909-11915. (Pubitemid 36800163)
27. Atsumi, G., M. Murakami, K. Kojima, A. Hadano, M. Tajima, and I. Kudo. 2000. Distinct roles of two intracellular phospholipase A2s in fatty acid release in the cell death pathway: proteolytic fragment of type IVA cytosolic phospholipase A2alpha inhibits stimulus-induced arachidonate release, whereas that of type VI Ca2+-independent phospholipase A2 augments spontaneous fatty acid release. J. Biol. Chem. 275: 18248-18258. (Pubitemid 30416946)
28. Roshak, A. K., E. A. Capper, C. Stevenson, C. Eichman, and L. A. Marshall. 2000. Human calcium-independent phospholipase A2 mediates lymphocyte proliferation. J. Biol. Chem. 275: 35692-35698.
29. Balboa, M. A., R. Pérez, and J. Balsinde. 2008. Calcium-independent phospholipase A2 mediates proliferation of human promonocytic U937 cells. FEBS J. 275: 1915-1924. (Pubitemid 351464009)
30. Poitout, V. 2008. Phospholipid hydrolysis and insulin secretion: a step toward solving the Rubik's cube. Am. J. Physiol. Endocrinol. Metab. 294: E214-E216. (Pubitemid 351231445)
31. Malaviya, R., J. Ansell, L. Hall, M. Fahmy, R. L. Argentieri, G. C. Olini, Jr., D. W. Pereira, R. Sur, and D. Cavender. 2006. Targeting cytosolic phospholipase A2 by arachidonyl trifluoromethyl ketone prevents chronic inflammation in mice. Eur. J. Pharmacol. 539: 195-204. (Pubitemid 43783524)
32. Kahlenberg, J. M., K. C. Lundberg, S. B. Kertesy, Y. Qu, and G. R. Dubyak. 2005. Potentiation of caspase-1 activation by the P2X7 receptor is dependent on TLR signals and requires NF-kappaB-driven protein synthesis. J. Immunol. 175: 7611-7622. (Pubitemid 41713461)
33. Qu, Y., L. Franchi, G. Nunez, and G. R. Dubyak. 2007. Nonclassical IL-1 beta secretion stimulated by P2X7 receptors is dependent on inflammasome activation and correlated with exosome release in murine macrophages. J. Immunol. 179: 1913-1925.
34. Dinarello, C. A. 1996. Biologic basis for interleukin-1 in disease. Blood 87: 2095-2147. (Pubitemid 26086851)
35. Fernandes, J. C., J. Martel-Pelletier, and J. P. Pelletier. 2002. The role of cytokines in osteoarthritis pathophysiology. Biorheology 39: 237-246. (Pubitemid 34626067)
36. Molina-Holgado, E., S. Ortiz, F. Molina-Holgado, and C. Guaza. 2000. Induction of COX-2 and PGE(2) biosynthesis by IL-1beta is mediated by PKC and mitogen-activated protein kinases in murine astrocytes. Br. J. Pharmacol. 131: 152-159.
37. Dinarello, C. A. 1998. Interleukin-1, interleukin-1 receptors and interleukin-1 receptor antagonist. Int. Rev. Immunol. 16: 457-499. (Pubitemid 28286181)
38. Manninen, P., E. Häivälä, S. Sarimo, and H. Kallio. 1997. Distribution of microbes in supercritical CO2 extraction of sea buckthorn (Hippophaë rhamnoides) oils. Zeitschrift für Lebensmitteluntersuchung und -Forschung A 204: 202-205. DOI: 10.1007/s002170050063.
39. Gertsch, J., R. Schoop, U. Kuenzle, and A. Suter. 2004. Echinacea alkylamides modulate TNF-alpha gene expression via cannabinoid receptor CB2 and multiple signal transduction pathways. FEBS Lett. 577: 563-569. (Pubitemid 39535349)
40. Sundström, C., and K. Nilsson. 1976. Establishment and characterization of a human histiocytic lymphoma cell line (U-937). Int. J. Cancer 17: 565-577.
41. Jursik, C., R. Sluyter, J. G. Georgiou, S. J. Fuller, J. S. Wiley, and B. J. Gu. 2007. A quantitative method for routine measurement of cell surface P2X7 receptor function in leucocyte subsets by two-colour time-resolved flow cytometry. J. Immunol. Methods 325: 67-77. (Pubitemid 47238290)
42. Balboa, M. A., and J. Balsinde. 2002. Involvement of calcium-independent phospholipase A2 in hydrogen peroxide-induced accumulation of free fatty acids in human U937 cells. J. Biol. Chem. 277: 40384-40389. (Pubitemid 35215612)
43. Pérez, R., R. Melero, M. A. Balboa, and J. Balsinde. 2004. Role of group VIA calcium-independent phospholipase A2 in arachidonic acid release, phospholipid fatty acid incorporation, and apoptosis in U937 cells responding to hydrogen peroxide. J. Biol. Chem. 279: 40385-40391. (Pubitemid 39287626)
44. Wen, B., W. Eli, Q. Xue, X. Dong, and W. Liu. 2007. Ultrasound accelerated esterification of palmitic acid with vitamin C. Ultrason. Sonochem. 14: 213-218. (Pubitemid 44499060)
45. Jain, M. K., B. Z. Yu, M. H. Gelb, and O. G. Berg. 1992. Assay of phospholipases A(2) and their inhibitors by kinetic analysis in the scooting mode. Mediators Inflamm. 1: 85-100.
46. Bayburt, T., and M. H. Gelb. 1997. Interfacial catalysis by human 85 kDa cytosolic phospholipase A2 on anionic vesicles in the scooting mode. Biochemistry 36: 3216-3231. (Pubitemid 27142394)
47. Weerheim, A. M., A. M. Kolb, A. Sturk, and R. Nieuwland. 2002. Phospholipid composition of cell-derived microparticles determined by one-dimensional high-performance thin-layer chromatography. Anal. Biochem. 302: 191-198. (Pubitemid 34229723)
48. Eidukevicius, R., D. Characiejus, R. Janavicius, N. Kazlauskaite, V. Pasukoniene, M. Mauricas, and W. Den Otter. 2005. A method to estimate cell cycle time and growth fraction using bromodeoxyuridine-flow cytometry data from a single sample. BMC Cancer 5: 122.
49. Thiele, D. L., M. Kurosaka, and P. E. Lipsky. 1983. Phenotype of the accessory cell necessary for mitogen-stimulated T and B cell responses in human peripheral blood: delineation by its sensitivity to the lysosomotropic agent, L-leucine methyl ester. J. Immunol. 131: 2282-2290. (Pubitemid 14227424)
50. Dixon, J. F., and K. Uyemura. 1987. Highly purified human T-lymphocytes do not respond to mitogens - including calcium ionophore and phorbol ester. Immunol. Invest. 16: 189-200. (Pubitemid 17144265)
51. Folch, J., M. Lees, and G. H. Sloane Stanley. 1957. A simple method for the isolation and purification of total lipides from animal tissues. J. Biol. Chem. 226: 497-509.
52. Obata, T., Y. Sakurai, Y. Kase, Y. Tanifuji, and T. Horiguchi. 2003. Simultaneous determination of endocannabinoids (arachidonylethanolamide and 2-arachidonylglycerol) and isoprostane (8-epiprostaglandin F2alpha) by gas chromatography-mass spectrometry-selected ion monitoring for medical samples. J. Chromatogr. B Analyt. Technol. Biomed. Life Sci. 792: 131-140. (Pubitemid 36773810)
53. Balazy, M. 1991. Metabolism of 5,6-epoxyeicosatrienoic acid by the human platelet: formation of novel thromboxane analogs. J. Biol. Chem. 266: 23561-23567. (Pubitemid 21908834)
54. Wübert, J., E. Reder, A. Kaser, P. C. Weber, and R. L. Lorenz. 1997. Simultaneous solid phase extraction, derivatization, and gas chromatographic mass spectrometric quantification of thromboxane and prostacyclin metabolites, prostaglandins, and isoprostanes in urine. Anal. Chem. 69: 2143-2146. (Pubitemid 27279475)
55. Aderem, A., and R. J. Ulevitch. 2000. Toll-like receptors in the induction of the innate immune response. Nature 406: 782-787.
56. Castagna, M., Y. Takai, K. Kaibuchi, K. Sano, U. Kikkawa, and Y. Nishizuka. 1982. Direct activation of calcium-activated, phospholipid-dependent protein kinase by tumor-promoting phorbol esters. J. Biol. Chem. 257: 7847-7851. (Pubitemid 12043279)
57. Los, M., W. Dröge, and K. Schulze-Osthoff. 1994. Inhibition of activation of transcription factor AP-1 by CD28 signalling in human T-cells. Biochem. J. 302: 119-123. (Pubitemid 24256343)
58. Nüsslein, H. G., K. H. Frosch, W. Woith, P. Lane, J. R. Kalden, and B. Manger. 1996. Increase of intracellular calcium is the essential signal for the expression of CD40 ligand. Eur. J. Immunol. 26: 846-850. (Pubitemid 26118297)
59. Inesi, G., R. Wade, and T. Rogers. 1998. The sarcoplasmic reticulum Ca2+ pump: inhibition by thapsigargin and enhancement by adenovirus-mediated gene transfer. Ann. N. Y. Acad. Sci. 853: 195-206.
60. Andrei, C., P. Margiocco, A. Poggi, L. V. Lotti, M. R. Torrisi, and A. Rubartelli. 2004. Phospholipases C and A2 control lysosome-mediated IL-1 beta secretion: implications for inflammatory processes. Proc. Natl. Acad. Sci. USA 101: 9745-9750. (Pubitemid 38869307)
61. Perregaux, D. G., R. E. Laliberte, and C. A. Gabel. 1996. Human monocyte interleukin-1beta posttranslational processing: evidence of a volume-regulated response. J. Biol. Chem. 271: 29830-29838. (Pubitemid 26389614)
62. Yang, H. C., M. Mosior, C. A. Johnson, Y. Chen, and E. A. Dennis. 1999. Group-specific assays that distinguish between the four major types of mammalian phospholipase A2. Anal. Biochem. 269: 278-288. (Pubitemid 29201025)
63. Lucas, K. K., and E. A. Dennis. 2005. Distinguishing phospholipase A2 types in biological samples by employing group-specific assays in the presence of inhibitors. Prostaglandins Other Lipid Mediat. 77: 235-248. (Pubitemid 41133432)
64. Carman, G. M., R. A. Deems, and E. A. Dennis. 1995. Lipid signaling enzymes and surface dilution kinetics. J. Biol. Chem. 270: 18711-18714.
65. Skipski, V. P., R. F. Peterson, and M. Barclay. 1964. Quantitative analysis of phospholipids by thin-layer chromatography. Biochem. J. 90: 374-378.
66. Nakagawa, Y., and K. Waku. 1989. Phospholipids. In Lipids and Related Compounds. Springer Protocols, Berlin, p. 149-178.
67. Jolad, S. D., R. C. Lantz, G. J. Chen, R. B. Bates, and B. N. Timmermann. 2005. Commercially processed dry ginger (Zingiber officinale): composition and effects on LPS-stimulated PGE2 production. Phytochemistry 66: 1614-1635. (Pubitemid 40950555)
68. Jolad, S. D., R. C. Lantz, A. M. Solyom, G. J. Chen, R. B. Bates, and B. N. Timmermann. 2004. Fresh organically grown ginger (Zingiber officinale): composition and effects on LPS-induced PGE2 production. Phytochemistry 65: 1937-1954. (Pubitemid 38981684)
69. Lantz, R. C., G. J. Chen, M. Sarihan, A. M. Sólyom, S. D. Jolad, and B. N. Timmermann. 2007. The effect of extracts from ginger rhizome on inflammatory mediator production. Phytomedicine 14: 123-128. (Pubitemid 46136942)
70. Dinarello, C. A. 1985. An update on human interleukin-1: from molecular biology to clinical relevance. J. Clin. Immunol. 5: 287-297. (Pubitemid 16257932)
71. Ha, H., J. H. Lee, H. N. Kim, H. M. Kim, H. B. Kwak, S. Lee, H. H. Kim, and Z. H. Lee. 2006. alpha-Lipoic acid inhibits inflammatory bone resorption by suppressing prostaglandin E2 synthesis. J. Immunol. 176: 111-117. (Pubitemid 43023254)
72. White, K. E., Q. Ding, B. B. Moore, M. Peters-Golden, L. B. Ware, M. A. Matthay, and M. A. Olman. 2008. Prostaglandin E2 mediates IL-1beta-related fibroblast mitogenic effects in acute lung injury through differential utilization of prostanoid receptors. J. Immunol. 180: 637-646.
73. Balsinde, J. 2002. Roles of various phospholipases A2 in providing lysophospholipid acceptors for fatty acid phospholipid incorporation and remodelling. Biochem. J. 364: 695-702. (Pubitemid 34680845)
74. Pérez-Chacón, G., A. M. Astudillo, D. Balgoma, M. A. Balboa, and J. Balsinde. 2009. Control of free arachidonic acid levels by phospholipases A2 and lysophospholipid acyltransferases. Biochim. Biophys. Acta 1791: 1103-1113.
75. Chilton, F. H., A. N. Fonteh, M. E. Surette, M. Triggiani, and J. D. Winkler. 1996. Control of arachidonate levels within inflammatory cells. Biochim. Biophys. Acta 1299: 1-15. (Pubitemid 26007728)
76. Diez, E., P. Louis-Flamberg, R. H. Hall, and R. J. Mayer. 1992. Substrate specificities and properties of human phospholipases A2 in a mixed vesicle model. J. Biol. Chem. 267: 18342-18348.
77. Burdge, G. C., A. Creaney, A. D. Postle, and D. C. Wilton. 1995. Mammalian secreted and cytosolic phospholipase A2 show different specificities for phospholipid molecular species. Int. J. Biochem. Cell Biol. 27: 1027-1032.
78. Burke, J. R., M. R. Witmer, and J. A. Tredup. 1999. The size and curvature of anionic covesicle substrate affects the catalytic action of cytosolic phospholipase A2. Arch. Biochem. Biophys. 365: 239-247. (Pubitemid 29391632)
79. Ghosh, M., D. E. Tucker, S. A. Burchett, and C. C. Leslie. 2006. Properties of the group IV phospholipase A2 family. Prog. Lipid Res. 45: 487-510.
80. Lio, Y. C., L. J. Reynolds, J. Balsinde, and E. A. Dennis. 1996. Irreversible inhibition of Ca(2+)-independent phospholipase A2 by methyl arachidonyl fluorophosphonate. Biochim. Biophys. Acta 1302: 55-60. (Pubitemid 26267041)
81. Surette, M. E., N. Dallaire, N. Jean, S. Picard, and P. Borgeat. 1998. Mechanisms of the priming effect of lipopolysaccharides on the biosynthesis of leukotriene B4 in chemotactic peptide-stimulated human neutrophils. FASEB J. 12: 1521-1531. (Pubitemid 28506721)
82. Rapoport, S. I. 2001. In vivo fatty acid incorporation into brain phosholipids in relation to plasma availability, signal transduction and membrane remodeling. J. Mol. Neurosci. 16: 243-261, discussion 279-284.
83. Rapoport, S. I. 2003. In vivo approaches to quantifying and imaging brain arachidonic and docosahexaenoic acid metabolism. J. Pediatr. 143: S26-S34. (Pubitemid 37346691)
84. Holman, R. T. 1986. Control of polyunsaturated acids in tissue lipids. J. Am. Coll. Nutr. 5: 183-211. (Pubitemid 16083228)
85. Basselin, M., L. Chang, R. Seemann, J. M. Bell, and S. I. Rapoport. 2005. Chronic lithium administration to rats selectively modifies 5-HT2A/2C receptor-mediated brain signaling via arachidonic acid. Neuropsychopharmacology 30: 461-472. (Pubitemid 40271149)
86. Aggarwal, B. B., A. B. Kunnumakkara, K. B. Harikumar, S. T. Tharakan, B. Sung, and P. Anand. 2008. Potential of spice-derived phytochemicals for cancer prevention. Planta Med. 74: 1560-1569.
87. Aggarwal, B. B., and S. Shishodia. 2006. Molecular targets of dietary agents for prevention and therapy of cancer. Biochem. Pharmacol. 71: 1397-1421.
88. Schmid, H. H. 2000. Pathways and mechanisms of N-acylethanolamine biosynthesis: can anandamide be generated selectively? Chem. Phys. Lipids 108: 71-87.
89. LoVerme, J., M. Guzmán, S. Gaetani, and D. Piomelli. 2006. Cold exposure stimulates synthesis of the bioactive lipid oleoylethanolamide in rat adipose tissue. J. Biol. Chem. 281: 22815-22818.
90. Dugasani, S., M. R. Pichika, V. D. Nadarajah, M. K. Balijepalli, S. Tandra, and J. N. Korlakunta. 2010. Comparative antioxidant and anti-inflammatory effects of [6]-gingerol, [8]-gingerol, [10]-gingerol and [6]-shogaol. J. Ethnopharmacol. 127: 515-520.
91. Patro, B. S., S. Rele, G. J. Chintalwar, S. Chattopadhyay, S. Adhikari, and T. Mukherjee. 2002. Protective activities of some phenolic 1,3-diketones against lipid peroxidation: possible involvement of the 1,3-diketone moiety. ChemBioChem 3: 364-370. (Pubitemid 34464789)
92. Balboa, M. A., R. Pérez, and J. Balsinde. 2003. Amplification mechanisms of inflammation: paracrine stimulation of arachidonic acid mobilization by secreted phospholipase A2 is regulated by cytosolic phospholipase A2-derived hydroperoxyeicosatetraenoic acid. J. Immunol. 171: 989-994. (Pubitemid 36871414)
93. Kuwata, H., S. Yamamoto, Y. Miyazaki, S. Shimbara, Y. Nakatani, H. Suzuki, N. Ueda, S. Yamamoto, M. Murakami, and I. Kudo. 2000. Studies on a mechanism by which cytosolic phospholipase A2 regulates the expression and function of type IIA secretory phospholipase A2. J. Immunol. 165: 4024-4031. (Pubitemid 32057314)
94. Murakami, M., Y. Nakatani, H. Kuwata, and I. Kudo. 2000. Cellular components that functionally interact with signaling phospholipase A(2)s. Biochim. Biophys. Acta 1488: 159-166.
95. Burke, J. E., and E. A. Dennis. 2009. Phospholipase A2 structure/function, mechanism, and signaling. J. Lipid Res. 50: S237-S242.
96. Chakraborti, S. 2003. Phospholipase A(2) isoforms: a perspective. Cell. Signal. 15: 637-665.
97. Harris, K. M., A. Fasano, and D. L. Mann. 2008. Cutting edge: IL-1 controls the IL-23 response induced by gliadin, the etiologic agent in celiac disease. J. Immunol. 181: 4457-4460.
98. Pathak, S., E. Goldofsky, E. X. Vivas, V. R. Bonagura, and A. Vambutas. 2011. IL-1β is overexpressed and aberrantly regulated in corticosteroid nonresponders with autoimmune inner ear disease. J. Immunol. 186: 1870-1879.