Anti-inflammatory effects of trans-1,3-diphenyl-2,3-epoxypropane-1-one mediated by suppression of inflammatory mediators in LPS-stimulated RAW 264.7 macrophages

Food and Chemical Toxicology

Volumn 53, Issue , 2013, Pages 371-375

  Kim, Kil Nam ^a   Ko, Yeong Jong ^b   Kang, Min Cheol ^c   Yang, Hye Mi ^a   Roh, Seong Woon ^a   Oda, Tatsuya ^d   Jeon, You Jin ^c   Jung, Won Kyo ^e   Heo, Soo Jin ^f   Yoon, Weon Jong ^b   Kim, Daekyung ^a  

^a Korea Basic Science Institute (KBSI)   (South Korea)

^b Jeju Biodiversity Research Institute   (South Korea)

^c Jeju National University   (South Korea)

^d NAGASAKI UNIVERSITY   (Japan)

^e Chosun University   (South Korea)

^f Korea Research Institute of Ships and Ocean Engineering   (South Korea)

Author keywords

Anti inflammatory; Macrophage; MAPKs; NF B; Trans 1,3 diphenyl 2,3 epoxypropan 1 one (DPEP)

Indexed keywords

1,3 DIPHENYL 2,3 EPOXYPROPANE 1 ONE; ANTIINFLAMMATORY AGENT; CYCLOOXYGENASE 2; I KAPPA B ALPHA; IMMUNOGLOBULIN ENHANCER BINDING PROTEIN; INDUCIBLE NITRIC OXIDE SYNTHASE; INTERLEUKIN 1BETA; INTERLEUKIN 6; LIPOPOLYSACCHARIDE; MITOGEN ACTIVATED PROTEIN KINASE; NITRIC OXIDE; PROSTAGLANDIN E2; STRESS ACTIVATED PROTEIN KINASE; SYNAPTOPHYSIN; TUMOR NECROSIS FACTOR ALPHA; UNCLASSIFIED DRUG;

ANIMAL CELL; ANTIINFLAMMATORY ACTIVITY; ARTICLE; CONCENTRATION RESPONSE; CONTROLLED STUDY; CYTOKINE PRODUCTION; ENZYME PHOSPHORYLATION; INFLAMMATION; MACROPHAGE; MACROPHAGE ACTIVATION; MOUSE; NONHUMAN; SIGNAL TRANSDUCTION;

ANIMALS; ANTI-INFLAMMATORY AGENTS; CELL LINE, TUMOR; CYCLOOXYGENASE 2; DINOPROSTONE; EPOXY COMPOUNDS; I-KAPPA B KINASE; INFLAMMATION; INFLAMMATION MEDIATORS; INTERLEUKIN-1BETA; INTERLEUKIN-6; JNK MITOGEN-ACTIVATED PROTEIN KINASES; LIPOPOLYSACCHARIDES; MACROPHAGES; MICE; NF-KAPPA B; NITRIC OXIDE; NITRIC OXIDE SYNTHASE TYPE II; P38 MITOGEN-ACTIVATED PROTEIN KINASES; PHOSPHORYLATION; PROPANE; SIGNAL TRANSDUCTION; TUMOR NECROSIS FACTOR-ALPHA;

EID: 84872383575     PISSN: 02786915     EISSN: 18736351     Source Type: Journal    
DOI: 10.1016/j.fct.2012.12.021     Document Type: Article

References (32)

1. Aggarwal B.B., Natarajan K. Tumor necrosis factors: developments during the last decade. Eur. Cytokine Netw. 1996, 7:93-124.
2. Ahmad N., Chen L.C., Gordon M.A., Laskin J.D., Laskin D.L. Regulation of cyclooxygenase-2 by nitric oxide in activated hepatic macrophages during acute endotoxemia. J. Leukoc. Biol. 2002, 71:1005-1011.
3. Ajizian S.J., English B.K., Meals E.A. Specific inhibitors of p38 and extracellular signal-regulated kinase mitogen-activated protein kinase pathways block inducible nitric oxide synthase and tumor necrosis factor accumulation in murine macrophages stimulated with lipopolysaccharide and interferon-gamma. J. Infect. Dis. 1999, 179:939-944.
4. Ban H.S., Suzuki K., Lim S.S., Jung S.H., Lee S., Ji J., Lee H.S., Lee Y.S., Shin K.H., Ohuchi K. Inhibition of lipopolysaccharide-induced expression of inducible nitric oxide synthase and tumor necrosis factor-alpha by 2'-hydroxychalcone derivatives in RAW 264.7 cells. Biochem. Pharmacol. 2004, 67:1549-1557.
5. Bandgar B.P., Gawande S.S., Bodade R.G., Totre J.V., Khobragade C.N. Synthesis and biological evaluation of simple methoxylated chalcones as anticancer, anti-inflammatory and antioxidant agents. Bioorg. Med. Chem. 2010, 18:1364-1370.
6. Bhat N.R., Zhang P., Lee J.C., Hogan E.L. Extracellular signal-regulated kinase and p38 subgroups of mitogen-activated protein kinases regulate inducible nitric oxide synthase and tumor necrosis factor-alpha gene expression in endotoxin-stimulated primary glial cultures. J. Neurosci. 1998, 18:1633-1641.
7. Chang Y.C., Li P.C., Chen B.C., Chang M.S., Wang J.L., Chiu W.T., Lin C.H. Lipoteichoic acid-induced nitric oxide synthase expression in RAW 264.7 macrophages is mediated by cyclooxygenase-2, prostaglandin E2, protein kinase A, p38 MAPK, and nuclear factor-kappaB pathways. Cell. Signal. 2006, 18:1235-1243.
8. Cheenpracha S., Karalai C., Ponglimanont C., Subhadhirasakul S., Tewtrakul S. Anti-HIV-1 protease activity of compounds from Boesenbergia pandurata. Bioorg. Med. Chem. 2006, 14:1710-1714.
9. Cho J.Y., Baik K.U., Jung J.H., Park M.H. In vitro anti-inflammatory effects of cynaropicrin, a sesquiterpene lactone, from Saussurea lappa. Eur. J. Pharmacol. 2000, 398:399-407.
10. Cobb M.H., Goldsmith E.J. How MAP kinases are regulated. J. Biol. Chem. 1995, 270:14843-14846.
11. Ghosh S., Karin M. Missing pieces in the NF-kappaB puzzle. Cell 2002, 109(Suppl):S81-96.
12. Herencia F., Ferrandiz M.L., Ubeda A., Guillen I., Dominguez J.N., Charris J.E., Lobo G.M., Alcaraz M.J. Novel anti-inflammatory chalcone derivatives inhibit the induction of nitric oxide synthase and cyclooxygenase-2 in mouse peritoneal macrophages. FEBS Lett. 1999, 453:129-134.
13. Hommes D.W., Peppelenbosch M.P., van Deventer S.J. Mitogen activated protein (MAP) kinase signal transduction pathways and novel anti-inflammatory targets. Gut 2003, 52:144-151.
14. Kim K.N., Heo S.J., Yoon W.J., Kang S.M., Ahn G., Yi T.H., Jeon Y.J. Fucoxanthin inhibits the inflammatory response by suppressing the activation of NF-kappaB and MAPKs in lipopolysaccharide-induced RAW 264.7 macrophages. Eur. J. Pharmacol. 2010, 649:369-375.
15. Lee H.J., Hyun E.A., Yoon W.J., Kim B.H., Rhee M.H., Kang H.K., Cho J.Y., Yoo E.S. In vitro anti-inflammatory and anti-oxidative effects of Cinnamomum camphora extracts. J. Ethnopharmacol. 2006, 103:208-216.
16. Lee H.S., Ryu D.S., Lee G.S., Lee D.S. Anti-inflammatory effects of dichloromethane fraction from Orostachys japonicus in RAW 264.7 cells: suppression of NF-kappaB activation and MAPK signaling. J. Ethnopharmacol. 2012, 140:271-276.
17. Lee S.H., Sohn D.H., Jin X.Y., Kim S.W., Choi S.C., Seo G.S. 2',4',6'-tris(methoxymethoxy) chalcone protects against trinitrobenzene sulfonic acid-induced colitis and blocks tumor necrosis factor-alpha-induced intestinal epithelial inflammation via heme oxygenase 1-dependent and independent pathways. Biochem. Pharmacol. 2007, 74:870-880.
18. Lee S.J., Bai S.K., Lee K.S., Namkoong S., Na H.J., Ha K.S., Han J.A., Yim S.V., Chang K., Kwon Y.G., Lee S.K., Kim Y.M. Astaxanthin inhibits nitric oxide production and inflammatory gene expression by suppressing I (kappa) B kinase-dependent NF-kappaB activation. Mol. Cells 2003, 16:97-105.
19. Liaras K., Geronikaki A., Glamoclija J., Ciric A., Sokovic M. Thiazole-based chalcones as potent antimicrobial agents. Synthesis and biological evaluation. Bioorg. Med. Chem. 2011, 19:3135-3140.
20. Liu R.H., Hotchkiss J.H. Potential genotoxicity of chronically elevated nitric oxide: a review. Mutat. Res. 1995, 339:73-89.
21. Medzhitov R., Janeway C.A. Innate immunity: impact on the adaptive immune response. Curr. Opin. Immunol. 1997, 9:4-9.
22. Nerya O., Musa R., Khatib S., Tamir S., Vaya J. Chalcones as potent tyrosinase inhibitors: the effect of hydroxyl positions and numbers. Phytochemistry 2004, 65:1389-1395.
23. Rajapakse N., Kim M.M., Mendis E., Kim S.K. Inhibition of inducible nitric oxide synthase and cyclooxygenase-2 in lipopolysaccharide-stimulated RAW264.7 cells by carboxybutyrylated glucosamine takes place via down-regulation of mitogen-activated protein kinase-mediated nuclear factor-kappaB signaling. Immunology 2008, 123:348-357.
24. Ruland J. Return to homeostasis: downregulation of NF-kappaB responses. Nat. Immunol. 2011, 12:709-714.
25. Sarkar D., Saha P., Gamre S., Bhattacharjee S., Hariharan C., Ganguly S., Sen R., Mandal G., Chattopadhyay S., Majumdar S., Chatterjee M. Anti-inflammatory effect of allylpyrocatechol in LPS-induced macrophages is mediated by suppression of iNOS and COX-2 via the NF-kappaB pathway. Int. Immunopharmacol. 2008, 8:1264-1271.
26. Serhan C.N., Savill J. Resolution of inflammation: the beginning programs the end. Nat. Immunol. 2005, 6:1191-1197.
27. Southan G.J., Szabo C. Selective pharmacological inhibition of distinct nitric oxide synthase isoforms. Biochem. Pharmacol. 1996, 51:383-394.
28. Tao J.Y., Zheng G.H., Zhao L., Wu J.G., Zhang X.Y., Zhang S.L., Huang Z.J., Xiong F.L., Li C.M. Anti-inflammatory effects of ethyl acetate fraction from Melilotus suaveolens Ledeb on LPS-stimulated RAW 264.7 cells. J. Ethnopharmacol. 2009, 123:97-105.
29. Uto T., Fujii M., Hou D.X. 6-(methylsulfinyl)hexyl isothiocyanate suppresses inducible nitric oxide synthase expression through the inhibition of Janus kinase 2-mediated JNK pathway in lipopolysaccharide-activated murine macrophages. Biochem. Pharmacol. 2005, 70:1211-1221.
30. Valla A., Valla B., Cartier D., Le Guillou R., Labia R., Florent L., Charneau S., Schrevel J., Potier P. New syntheses and potential antimalarial activities of new 'retinoid-like chalcones'. Eur. J. Med. Chem. 2006, 41:142-146.
31. Walsh N.C., Crotti T.N., Goldring S.R., Gravallese E.M. Rheumatic diseases: the effects of inflammation on bone. Immunol. Rev. 2005, 208:228-251.
32. Yun K.J., Kim J.Y., Kim J.B., Lee K.W., Jeong S.Y., Park H.J., Jung H.J., Cho Y.W., Yun K., Lee K.T. Inhibition of LPS-induced NO and PGE2 production by asiatic acid via NF-kappa B inactivation in RAW 264.7 macrophages: possible involvement of the IKK and MAPK pathways. Int. Immunopharmacol. 2008, 8:431-441.