5,6,7-Trimethoxyflavone suppresses pro-inflammatory mediators in lipopolysaccharide-induced RAW 264.7 macrophages and protects mice from lethal endotoxin shock

Food and Chemical Toxicology

Volumn 62, Issue , 2013, Pages 847-855

  Rim, Hong Kun ^a   Yun, Chang Hyeon ^a   Shin, Ji Sun ^a   Cho, Young Wuk ^a   Jang, Dae Sik ^a   Ryu, Jong Hoon ^a   Park, Haeil ^b   Lee, Kyung Tae ^a  

^a Kyung Hee University   (South Korea)

^b Kangwon National University   (South Korea)

Author keywords

5,6,7 Trimethoxyflavone; Cyclooxygenase 2; Inducible nitric oxide synthase; Inflammation; Nuclear factor kappa B; Sepsis

Indexed keywords

5,6,7 TRIMETHOXYFLAVONE; ANTIINFLAMMATORY AGENT; CYCLOOXYGENASE 2; I KAPPA B ALPHA; IMMUNOGLOBULIN ENHANCER BINDING PROTEIN; INDUCIBLE NITRIC OXIDE SYNTHASE; INTERLEUKIN 1BETA; INTERLEUKIN 6; MESSENGER RNA; MITOGEN ACTIVATED PROTEIN KINASE; NITRIC OXIDE; PROSTAGLANDIN E2; STAT1 PROTEIN; STAT3 PROTEIN; TRANSCRIPTION FACTOR AP 1; TUMOR NECROSIS FACTOR ALPHA; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANTIINFLAMMATORY ACTIVITY; ARTICLE; CONTROLLED STUDY; CYCLOOXYGENASE 2 GENE; DOSE RESPONSE; DOWN REGULATION; DRUG EFFECT; ENDOTOXEMIA; ENZYME INHIBITION; INDUCIBLE NITRIC OXIDE SYNTHASE GENE; INTERLEUKIN 1BETA GENE; INTERLEUKIN 6 GENE; MACROPHAGE ACTIVATION; MALE; MOUSE; NONHUMAN; PROTEIN BLOOD LEVEL; PROTEIN EXPRESSION; PROTEIN PHOSPHORYLATION; SEPTIC SHOCK; SURVIVAL RATE; TUMOR NECROSIS FACTOR ALPHA GENE;

MUS;

5,6,7-TRIMETHOXYFLAVONE; CYCLOOXYGENASE-2; INDUCIBLE NITRIC OXIDE SYNTHASE; INFLAMMATION; NUCLEAR FACTOR-KAPPA B; SEPSIS;

ANIMALS; ANTI-INFLAMMATORY AGENTS, NON-STEROIDAL; CELL LINE; CYCLOOXYGENASE 2; CYTOKINES; DOSE-RESPONSE RELATIONSHIP, DRUG; ENDOTOXEMIA; FLAVONOIDS; INFLAMMATION MEDIATORS; INTERLEUKIN-6; LIPOPOLYSACCHARIDES; MACROPHAGES; MALE; MICE; MICE, INBRED C57BL; NF-KAPPA B; NITRIC OXIDE SYNTHASE TYPE II; SHOCK, SEPTIC;

EID: 84887558773     PISSN: 02786915     EISSN: 18736351     Source Type: Journal    
DOI: 10.1016/j.fct.2013.10.025     Document Type: Article

References (38)

1. Ahmed J.S. The role of cytokines in immunity and immunopathogenesis of pirolasmoses. Parasitol. Res. 2002, 88:S48-S50.
2. Akira S., Takeda K. Toll-like receptor signalling. Nat. Rev. Immunol. 2004, 4:499-511.
3. Alexopoulou L., Holt A.C., Medzhitov R., Flavell R.A. Recognition of double-stranded RNA and activation of NF-kappaB by Toll-like receptor 3. Nature 2001, 413:732-738.
4. Christiaens I., Zaragoza D.B., Guilbert L., Robertson S.A., Mitchell B.F., Olson D.M. Inflammatory processes in preterm and term parturition. J. Reprod. Immunol. 2008, 79:50-57.
5. Darnell J.E., Kerr I.M., Stark G.R. Jak-STAT pathways and transcriptional activation in response to IFNs and other extracellular signaling proteins. Science 1994, 264:1415-1421.
6. Doyle S.L., O'Neill L.A. Toll-like receptors: from the discovery of NFkappaB to new insights into transcriptional regulations in innate immunity. Biochem. Pharmacol. 2006, 72:1102-1113.
7. Duffield J.S. The inflammatory macrophage: a story of Jekyll and Hyde. Clin. Sci. 2003, 104:27-38.
8. Fichtner-Feigl S., Fuss I.J., Preiss J.C., Strober W., Kitani A. Treatment of murine Th1- and Th2-mediated inflammatory bowel disease with NF-kappa B decoy oligonucleotides. J. Clin. Invest. 2005, 115:3057-3071.
9. Hayashi K., Hayashi T., Otsuka H., Takeda Y. Antiviral activity of 5,6,7-trimethoxyflavone and its potentiation of the antiherpes activity of acyclovir. J. Antimicrob. Chemother. 1997, 39:821-824.
10. Hosozawa S., Kato N., Munakata K. 5,6,7-Trimethoxyflavone from Callicarpa japonica. Phytochemistry 1972, 11:2362.
11. Huang W.H., Yang C.H., Chien P.Y., Lee A.R. Synthesis of 5,6,7-trimethoxyflavone as a key intermediate for the preparation of baicalein. Chin. Pharm. J. 2003, 55:101-107.
12. Huang W.H., Lee A.R., Chien P.Y., Chou T.C. Synthesis of baicalein derivatives as potential anti-aggregatory and anti-inflammatory agents. J. Pharm. Pharmacol. 2005, 57:219-225.
13. Kaplanski G., Marin V., Montero-Julian F., Mantovani A., Farnarier C. IL-6: a regulator of the transition from neutrophil to monocyte recruitment during inflammation. Trends Immunol. 2003, 24:25-29.
14. Kim D.H., Yun C.H., Kim M.H., Kumar C.N., Yun B.H., Shin J.S., An H.J., Lee Y.H., Yun Y.D., Rim H.K., Yoo M.S., Lee K.T., Lee Y.S. 4'-Bromo-5,6,7-trimethoxyflavone represses lipopolysaccharide-induced iNOS and COX-2 expressions by suppressing the NF-kB signaling pathway in RAW 264.7 macrophages. Bioorg. Med. Chem. Lett. 2012, 22:700-705.
15. Klotz L., Schmidt M., Giese T., Sastre M., Knolle P., Klockgether T., Heneka M.T. Proinflammatory stimulation and pioglitazone treatment regulate peroxisome proliferator-activated receptor gamma levels in peripheral blood mononuclear cells from healthy controls and multiple sclerosis patients. J. Immunol. 2005, 175:4948-4955.
16. Kutney J.P., Hanssen H.W. 5,6,7-Trimethoxyflavone and 5,6,7,8-tetramethoxyflavone from Zeyhera tuberculosa. Phytochemistry 1971, 10:3298-3302.
17. Lappas M., Permezel M., Georgiou H.M., Rice G.E. Nuclear factor kappa B regulation of proinflammatory cytokines in human gestational tissues in vitro. Biol. Reprod. 2002, 67:668-673.
18. Lawrence T., Willoughby D.A., Gilroy D.W. Anti-inflammatory lipid mediators and insights into the resolution of inflammation. Nat. Rev. Immunol. 2002, 2:787-795.
19. Lee Y., Yeo H., Liu S.H., Jiang Z., Savizky R.M., Austin D.J., Cheng Y.C. Increased anti-P-glycoprotein activity of baicalein by alkylation on the A ring. J. Med. Chem. 2004, 47:5555-5566.
20. Li Q., Verma I.M. NF-kappaB regulation in the immune system. Nat. Rev. Immunol. 2002, 2:725-734.
21. Liao H.L., Hu M.K. Synthesis and anticancer activities of 5,6,7-trimethylbaicalein derivatives. Chem. Pharm. Bull. 2004, 52:1162-1165.
22. Liu S.F., Malik A.B. NF-kappa B activation as a pathological mechanism of septic shock and inflammation. Am. J. Physiol. Lung Cell. Mol. Physiol. 2006, 290:L622-L645.
23. Mabalirajan U., Ahmad T., Rehman R., Leishangthem G.D., Dinda A.K., Agrawal A., Ghosh B., Sharma S.K. Baicalein reduces airway injury in allergen and IL-13 induced airway inflammation. PLoS One 2013, 8:e62916.
24. Panichpol K., Waterman P.G. Novel flavonoids from the stem of Popowia cauliflora. Phytochemistry 1978, 17:1363-1367.
25. Pinar M. 5,6,7-Trimethoxyflavone and 5,6,7,4'-tetramethoxyflavone from Kichxia lanigera. Phytochemistry 1973, 12:3014-3015.
26. Ponchel F., Morgan A.W., Bingham S.J., Quinn M., Buch M., Verburg R.J., Henwood J., Douglas S.H., Masurel A., Conaghan P., Gesinde M., Taylor J., Markham A.F., Emery P., van Laar J.M., Isaacs J.D. Dysregulated lymphocyte proliferation and differentiation in patients with rheumatoid arthritis. Blood 2002, 100:4550-4556.
27. 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.
28. Sakagami T., Vella J., Dixon M.F., O'Rourke J., Radcliff F., Sutton P., Shimoyama T., Beagley K., Lee A. The endotoxin of helicobacter pylori is a modulator of host-dependent gastritis. Infect. Immun. 1997, 65:3310-3316.
29. Sakurai H., Nishi A., Sato N., Mizukami J., Miyoshi H., Sugita T. TAK1-TAB1 fusion protein: a novel constitutively active mitogen-activated protein kinase kinase kinase that stimulates AP-1 and NF-kappaB signaling pathways. Biochem. Biophys. Res. Commun. 2002, 297:1277-1281.
30. Sanchez-Perez I., Benitah S.A., Martinez-Gomariz M., Lacal J.C., Perona R. Cell stress and MEKK1-mediated c-Jun activation modulate NFkappaB activity and cell viability. Mol. Biol. Cell 2002, 13:2933-2945.
31. Simi A., Ingelman-Sundberg M., Tindberg N. Neuroprotective agent chlomethiazole attenuates c-fos, c-jun, and AP-1 activation through inhibition of p38 MAP kinase. J. Cereb. Blood Flow Metab. 2000, 20:1077-1088.
32. Stancovski I., Baltimore D. NF-kappaB activation: the I kappaB kinase revealed?. Cell 1997, 91:299-302.
33. Suresh Babu K., Hari Babu T., Srinivas P.V., Sastry B.S., Hara Kishore K., Murty U.S., Madhusudana Rao J. Synthesis and in vitro study of novel 7-O-acyl derivatives of Oroxylin A as antibacterial agents. Bioorg. Med. Chem. Lett. 2005, 15:3953-3956.
34. Tseng T.L., Chen M.F., Tsai M.J., Hsu Y.H., Chen C.P., Lee T.J. Oroxylin-A rescues LPS-induced acute lung injury via regulation of NF-κB signaling pathway in rodents. PLoS One 2012, 7:e47403.
35. Van Amersfoort E.S., Van Berkel T.J., Kuiper J. Receptors, mediators, and mechanisms involved in bacterial sepsis and septic shock. Clin. Microbiol. Rev. 2003, 16:379-414.
36. Walle T. Methylation of dietary flavones greatly improves their hepatic metabolic stability and intestinal absorption. Mol. Pharm. 2007, 4:826-832.
37. Xu M., Lu N., Sun Z., Zhang H., Dai Q., Wei L., Li Z., You Q., Guo Q. Activation of the unfolded protein response contributed to the selective cytotoxicity of oroxylin A in human hepatocellular carcinoma HepG2 cells. Toxicol. Lett. 2012, 212:113-125.
38. Zhang H.B., Lu P., Guo Q.Y., Zhang Z.H., Meng X.Y. Baicalein induces apoptosis in esophageal squamous cell carcinoma cells through modulation of the PI3K/Akt pathway. Oncol. Lett. 2013, 5:722-728.