Regiospecific methylation of a dietary flavonoid scaffold selectively enhances IL-1β production following toll-like receptor 2 Stimulation in THP-1 monocytes

Journal of Biological Chemistry

Volumn 288, Issue 29, 2013, Pages 21126-21135

  Lim, Eng Kiat ^a   Mitchell, Paul J ^a   Brown, Najmeeyah ^a   Drummond, Rebecca A ^b   Brown, Gordon D ^c   Kaye, Paul M ^a   Bowles, Dianna J ^b  

^a UNIVERSITY OF HULL   (United Kingdom)

^b UNIVERSITY OF ABERDEEN   (United Kingdom)

^c UNIVERSITY OF YORK   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

BIOACTIVITY; FLAVONOIDS; METHYLATION;

FLAVONOID; IMMUNOMODULATORS; NATURAL PRODUCTS; REGIOSPECIFIC; SIDE-CHAINS; THP-1 CELLS; THP-1 MONOCYTES; TOLL-LIKE RECEPTOR 2;

ALKYLATION;

CATECHIN; FLAVANONE DERIVATIVE; FLAVONE DERIVATIVE; FLAVONOID; FLAVONOL DERIVATIVE; IMMUNOGLOBULIN ENHANCER BINDING PROTEIN; IMMUNOMODULATING AGENT; INFLAMMASOME; INTERLEUKIN 1BETA; NUTRACEUTICAL; PROCYANIDIN DERIVATIVE; STAT1 PROTEIN; TOLL LIKE RECEPTOR 2; CYCLOHEXIMIDE; INTERLEUKIN 1BETA CONVERTING ENZYME; LIPOPEPTIDE; MESSENGER RNA; MITOGEN ACTIVATED PROTEIN KINASE; PAM(3)CSK(4) PEPTIDE; QUERCETIN; QUERCETIN 3-O-METHYL ETHER;

APOPTOSIS; ARTICLE; BIOLOGICAL ACTIVITY; CONTROLLED STUDY; CYTOKINE RELEASE; ENZYME ACTIVATION; ENZYME RELEASE; ENZYME SYNTHESIS; GENE EXPRESSION; HUMAN; HUMAN CELL; INNATE IMMUNITY; MONOCYTE; PRIORITY JOURNAL; TRANSCRIPTION REGULATION; AGONISTS; ANALOGS AND DERIVATIVES; BIOLOGICAL MODEL; BIOSYNTHESIS; CELL LINE; CHEMISTRY; DRUG EFFECTS; DRUG POTENTIATION; ENZYMOLOGY; GENE EXPRESSION REGULATION; GENETIC TRANSCRIPTION; GENETICS; METABOLISM; METHYLATION; PHOSPHORYLATION; SECRETION (PROCESS); STEREOISOMERISM;

CASPASE 1; CELL LINE; CYCLOHEXIMIDE; DRUG SYNERGISM; FLAVONOIDS; GENE EXPRESSION REGULATION; HUMANS; INTERLEUKIN-1BETA; LIPOPEPTIDES; METHYLATION; MITOGEN-ACTIVATED PROTEIN KINASES; MODELS, BIOLOGICAL; MONOCYTES; PHOSPHORYLATION; QUERCETIN; RNA, MESSENGER; STEREOISOMERISM; TOLL-LIKE RECEPTOR 2; TRANSCRIPTION, GENETIC;

EID: 84880550807     PISSN: 00219258     EISSN: 1083351X     Source Type: Journal    
DOI: 10.1074/jbc.M113.453514     Document Type: Article

References (53)

1. Martin, C., Butelli, E., Petroni, K., and Tonelli, C. (2011) How can research on plants contribute to promoting human health? Plant Cell 23,1685-1699
2. Crozier, A., Jaganath, I. B., and Clifford, M. N. (2009) Dietary phenolics: chemistry, bioavailability and effects on health. Nat. Prod. Rep. 26, 1001-1043
3. Ríos, J. L., Recio, M. C., Escandell, J. M., and Andújar, I. (2009) Inhibition of transcription factors by plant-derived compounds and their implications in inflammation and cancer. Curr. Pharm. Des. 15,1212-1237
4. Schmidt, T. J., Khalid, S. A., Romanha, A. J., Alves, T. M., Biavatti, M. W., Brun, R., Da Costa, F. B., de Castro, S. L., Ferreira, V. F., de Lacerda, M. V. G., Lago, J. H. G., Leon, L. L., Lopes, N. P., das Neves Amorim, R. C., Niehues, M., Ogungbe, I. V., Pohlit, A. M., Scotti, M. T., Setzer, W. N., de N C Soeiro, M., Steindel, M., and Tempone, A. G. (2012) The potential of secondary metabolites from plants as drugs or leads against protozoan neglected diseases - Part I. Curr. Med. Chem. 19, 2128-2175
5. Schmidt, T. J., Khalid, S. A., Romanha, A. J., Alves, T. M., Biavatti, M. W., Brun, R., Da Costa, F. B., de Castro, S. L., Ferreira, V. F., de Lacerda, M. V. G., Lago, J. H. G., Leon, L. L., Lopes, N. P., das Neves Amorim, R. C., Niehues, M., Ogungbe, I. V., Pohlit, A. M., Scotti, M. T., Setzer, W. N., de N C Soeiro, M., Steindel, M., and Tempone, A. G. (2012) The potential of secondary metabolites from plants as drugs or leads against protozoan neglected diseases - Part II. Curr. Med. Chem. 19, 2176-2228
6. Hemaiswarya, S., Kruthiventi, A. K., and Doble, M. (2008) Synergism between natural products and antibiotics against infectious diseases. Phyto-medicine 15, 639-652
7. MacDonald, T. T., and Monteleone, G. (2005) Immunity, inflammation, and allergy in the gut. Science 307,1920 -1925
8. Tlaskalovä-Hogenovä, H., Stepänkovä, R., Hudcovic, T., Tuckovä, L., Cuk-rowska, B., Lodinovä-Zädnikovä, R., Kozäkovä, H., Rossmann, P., Bärtovä, J., Sokol, D., Funda, D. P., Borovskä, D., Rehäkovä, Z., Sinkora, J., Hofman, J., Drastich, P., and Kokesovä, A. (2004) Commensal bacteria (normal microflora), mucosal immunity and chronic inflammatory and autoimmune diseases. Immunol. Lett. 93, 97-108
9. Marques, R., and Boneca, I. (2011) Expression and functional importance of innate immune receptors by intestinal epithelial cells. Cell Mol. Life Sci. 68, 3661-3673
10. Heimesaat, M. M., Fischer, A., Siegmund, B., Kupz, A., Niebergall, J., Fuchs, D., Jahn, H.-K., Freudenberg, M., Loddenkemper, C., Batra, A., Lehr, H.-A., Liesenfeld, O., Blaut, M., Göbel, U. B., Schumann, R. R., and Bereswill, S. (2007) Shift towards pro-inflammatory intestinal bacteria aggravates acute murine colitis via Toll-like receptors 2 and 4. Plos One 2, e662
11. Dong, L., Li, J., Liu, Y., Yue, W. J., and Luo, X. T. (2012) Toll-like receptor 2 monoclonal antibody or/and Toll-like receptor 4 monoclonal antibody increase counts of Lactobacilli and Bifidobacteria in dextran sulfate sodium-induced colitis in mice. J. Gastroenterol. Hepatol. 27,110-119
12. Albert, E. J., and Marshall, J. S. (2008) Aging in the absence of TLR2 is associated with reduced IFN-γ responses in the large intestine and increased severity of induced colitis. J. Leukoc. Biol. 83, 833- 842
13. Messlik, A., Schmechel, S., Kisling, S., Bereswill, S., Heimesaat, M. M., Fischer, A., Göbel, U., andHaller, D. (2009) Loss of Toll-like receptor 2 and 4 leads to differential induction of endoplasmic reticulum stress and pro-apoptotic responses in the intestinal epithelium under conditions of chronic inflammation. J. ProteomeRes. 8, 4406-4417
14. Cohen-Poradosu, R., McLoughlin, R. M., Lee, J. C., and Kasper, D. L. (2011) Bacteroides fragilis-stimulated interleukin-10 contains expanding disease. J. Infect. Dis. 204, 363-371
15. Lowe, E. L., Crother, T. R., Rabizadeh, S., Hu, B., Wang, H., Chen, S., Shimada, K., Wong, M. H., Michelsen, K. S., and Arditi, M. (2010) Toll-like receptor 2 signaling protects mice from tumor development in a mouse model of colitis-induced cancer. Plos One 5, e13027
16. de Oliveira, J. G., and Silva, A. E. (2012) Polymorphisms of the TLR2 and TLR4 genes are associated with risk of gastric cancer in a Brazilian population. World J. Gastroenterol. 18,1235-1242
17. Tahara, T., Arisawa, T., Wang, F., Shibata, T., Nakamura, M., Sakata, M., Hirata, I., and Nakano, H. (2008) Toll-like receptor 2 (TLR)-196 to 174del polymorphism in gastro-duodenal diseases in Japanese population. Dig. Dis. Sci. 53, 919 -924
18. BoraskaJelaviC, T., BarisiC, M., DrmicHofman, I., Boraska, V., Vrdoljak, E., Peruzovic, M., Hozo, I., Puljiz, Z., and Terzic, J. (2006) Microsatelite GT polymorphism in the Toll-like receptor 2 is associated with colorectal cancer. Clin. Genet. 70, 156 -160
19. Bhaskar, S., Shalini, V., and Helen, A. (2011) Quercetin regulates oxidized LDL induced inflammatory changes in human PBMCs by modulating the TLR-NF-κB signaling pathway. Immunobiology 216, 367-373
20. Byun, E. H., Omura, T., Yamada, K., and Tachibana, H. (2011) Green tea polyphenol epigallocatechin-3-gallate inhibits TLR2 signaling induced by peptidoglycan through the polyphenol sensing molecule 67-kDa laminin receptor. FEBS Lett. 585, 814- 820
21. Morimoto, M., Watanabe, T., Yamori, M., Takebe, M., and Wakatsuki, Y. (2009) Isoflavones regulate innate immunity and inhibit experimental colitis. J. Gastroenterol. Hepatol. 24, 1123-1129
22. Pichersky, E., and Lewinsohn, E. (2011) Convergent evolution in plant specialized metabolism. Annu. Rev. Plant Biol. 62, 549 -566
23. Modolo, L. V., Reichert, A. I., and Dixon, R. A. (2009) in Plant-Derived Natural Products: Synthesis, Function, and Application (Osbourn, A. E., and Lanzotti, V. eds), pp. 143-163, Springer, New York
24. Gaestel, M., Kotlyarov, A., and Kracht, M. (2009) Targeting innate immunity protein kinase signalling in inflammation. Nat. Rev. DrugDiscov. 8, 480-499
25. Martinon, F., Mayor, A., and Tschopp, J. (2009) The Inflammasomes: guardians of the body. Annu. Rev. Immunol. 27, 229-265
26. Li, Q., and Verma, I. M. (2002) NF-κB regulation in the immune system. Nat. Rev. Immunol. 2, 725-734
27. Rhee, S. H., Jones, B. W., Toshchakov, V., Vogel, S. N., and Fenton, M. J. (2003) Toll-like receptors 2 and 4 activate STAT1 serine phosphorylation by distinct mechanisms in macrophages. J. Biol. Chem. 278, 22506 -22512
28. Hershko, D. D., Robb, B. W., Wray, C. J., Luo, G. J., and Hasselgren, P. O. (2004) Superinduction of IL-6 by cycloheximide is associated with mRNA stabilization and sustained activation of p38 map kinase and NF-κBin cultured Caco-2 cells. J. Cell Biochem. 91, 951-961
29. Fenton, M. J., Clark, B. D., Collins, K. L., Webb, A. C., Rich, A., and Auron, P. E. (1987) Transcriptional regulation of the human prointerleukin 1β gene.J.Immunol. 138, 3972-3979
30. Zhang, Y., Saccani, S., Shin, H., and Nikolajczyk, B. S. (2008) Dynamic protein associations define two phases of IL-1β transcriptional activation. J.Immunol. 181, 503-512
31. Park, H. Y., Kim, G. Y., Hyun, J. W., Hwang, H. J., Kim, N. D., Kim, B. W., and Choi, Y. H. (2012) 7,8-Dihydroxyflavone exhibits anti-inflammatory properties by downregulating the NF-κB and MAPK signaling pathways in lipopolysaccharide-treated RAW264.7 cells. Int. J. Mol. Med. 29, 1146-1152
32. Kim, D. H., Yun, C. H., Kim, M. H., Naveen Kumar, C., Yun, B. H., Shin, J.-S., An, H. J., Lee, Y. H., Yun, Y. D., Rim, H.-K., Yoo, M.-S., Lee, K.-T., and Lee, Y. S. (2012) 4' -Bromo-5,6,7-trimethoxyflavone represses lipopolysac-charide-induced iNOS and COX-2 expressions by suppressing the NF-κB signaling pathway in RAW 264.7 macrophages. Bioorg. Med. Chem. Lett. 22, 700 -705
33. Lee, J. K., Kim, S. Y., Kim, Y. S., Lee, W.-H., Hwang, D. H., and Lee, J. Y. (2009) Suppression of the TRIF-dependent signaling pathway of Toll-like receptors by luteolin. Biochem. Pharmacol. 77,1391-1400
34. Nicholas, C., Batra, S., Vargo, M. A., Voss, O. H., Gavrilin, M. A., Wewers, M. D., Guttridge, D. C., Grotewold, E., and Doseff, A. I. (2007) Apigenin blocks lipopolysaccharide-induced lethality in vivo and proinflammatory cytokines expression by inactivating NF-κB through the suppression of p65 phosphorylation. J. Immunol. 179, 7121-7127
35. Soromou, L. W., Zhang, Z., Li, R., Chen, N., Guo, W., Huo, M., Guan, S., Lu, J., and Deng, X. (2012) Regulation of inflammatory cytokines in lipopo-lysaccharide-stimulated RAW 264.7 murine macrophage by 7-O-methyl-naringenin. Molecules 17, 3574-3585
36. Huo, M., Chen, N., Chi, G., Yuan, X., Guan, S., Li, H., Zhong, W., Guo, W., Soromou, L. W., Gao, R., Ouyang, H., Deng, X., and Feng, H. (2012) Traditional medicine alpinetin inhibits the inflammatory response in Raw 264.7 cells and mouse models. Int. Immunopharmacol. 12, 241-248
37. Han, J.-M., Jin, Y.-Y., Kim, H. Y., Park, K. H., Lee, W. S., and Jeong, T.-S. (2010) Lavandulyl flavonoids from Sophora flavescens suppress lipopoly-saccharide-induced activation of nuclear factor-κB and mitogen-acti-vated protein kinases in RAW264.7 cells. Biol. Pharm. Bull. 33, 1019-1023
38. Zheng, L. T., Ock, J., Kwon, B.-M., and Suk, K. (2008) Suppressive effects of flavonoid fisetin on lipopolysaccharide-induced microglial activation and neurotoxicity. Int. Immunopharmacol. 8, 484- 494
39. Choi, H.J., Eun, J.-S., Park, Y.-R., Kim, D. K., Li, R., Moon,W. S., Park, J. M., Kim, H. S., Cho, N.-P., Cho, S.-D., and Soh, Y. (2008) Ikarisoside A inhibits inducible nitric oxide synthase in lipopolysaccharide-stimulated RAW 264.7 cells via p38 kinase and nuclear factor-KB signaling pathways. Eur. J.Pharmacol. 601, 171-178
40. Park, S. E., Sapkota, K., Kim, S., Kim, H., and Kim, S. J. (2011) Kaempferol acts through mitogen-activated protein kinases and protein kinase B/AKT to elicit protection in a model of neuroinflammation in BV2 microglial cells. Br. J. Pharmacol. 164,1008 -1025
41. Soromou, L. W., Chen, N., Jiang, L., Huo, M., Wei, M., Chu, X., Millim-ouno, F. M., Feng, H., Sidime, Y., and Deng, X. (2012) Astragalin attenuates lipopolysaccharide-induced inflammatory responses by down-regulating NF-κB signaling pathway. Biochem. Biophys. Res. Commun. 419, 256-261
42. Kim, Y.-J., Ko, H., Park, J.-S., Han, I.-H., Amor, E. C., Lee, J. W., and Yang, H. O. (2010) Dimethyl cardamonin inhibits lipopolysaccharide-induced inflammatory factors through blocking NF-κB p65 activation. Int. Immu-nopharmacol. 10,1127-1134
43. Chu, X., Ci, X., Wei, M., Yang, X., Cao, Q., Guan, M., Li, H., Deng, Y., Feng, H., and Deng, X. (2012) Licochalcone A inhibits lipopolysaccharide-in- duced inflammatory response in vitro and in vivo. J. Agric. Food Chem. 60, 3947-3954
44. Del Rio, D., Borges, G., and Crozier, A. (2010) Berry flavonoids and phe-nolics: bioavailability and evidence of protective effects. Br. J.Nutr. 104, S67-S90
45. Boesch-Saadatmandi, C., Egert, S., Schrader, C., Coumou, X., Barouki, R., Muller, M. J., Wolffram, S., and Rimbach, G. (2010) Effect of quercetin on paraoxonase 1 activity - studies in cultured cells, mice and humans. J.Physiol. Pharmacol. 61, 99-105
46. De Santi, C., Pietrabissa, A., Mosca, F., and Pacifici, G. M. (2002) Methy-lation of quercetin and fisetin, flavonoids widely distributed in edible vegetables, fruits and wine, by human liver. Int. J. Clin. Pharmacol. Ther. 40, 207-212
47. Krenn, L., Wollenweber, E., Steyrleuthner, K., Goerick, C., and Melzig, M. F. (2009) Contribution of methylated exudate flavonoids to the anti-inflammatory activity of Grindelia robusta. Fitoterapia 80, 267-269
48. Jones, D. J. L., Lamb, J. H., Verschoyle, R. D., Howells, L. M., Butterworth, M., Lim, C. K., Ferry, D., Farmer, P. B., and Gescher, A. J. (2004) Characterisation of metabolites of the putative cancer chemopreventive agent quercetin and their effect on cyclo-oxygenase activity. Br. J. Cancer 91, 1213-1219
49. Shen, J.-K., Du, H.-p., Yang, M., Wang, Y.-G., and Jin, J. (2009) Casticin induces leukemic cell death through apoptosis and mitotic catastrophe. Ann. Hematol. 88, 743-752
50. Torres, F., Quintana, J., and Estevez, F. (2010) 5,7,3'-Trihydroxy-3,4'- dimethoxyflavone-induced cell death in human leukemia cells is dependent on vaspases and activates the MAPK pathway. Mol. Carcinog. 49, 464-475
51. Torres, F., Quintana, J., and Estevez, F. (2011) 5,7,3'-Trihydroxy-3,4'- dimethoxyflavone inhibits the tubulin polymerization and activates the sphingomyelin pathway. Mol. Carcinog. 50,113-122
52. Rubio, S., Quintana, J., Lopez, M., Eiroa, J. L., Triana, J., and Estevez, F. (2006) Phenylbenzopyrones structure-activity studies identify betuletol derivatives as potential antitumoral agents. Eur. J. Pharmacol. 548, 9 -20
53. Pardoll, D. (2003) Does the immune system see tumors as foreign or self? Annu. Rev. Immunol. 21, 807-839