Cinnamoyloxy-mammeisin Isolated from Geopropolis Attenuates Inflammatory Process by Inhibiting Cytokine Production: Involvement of MAPK, AP-1, and NF-κB

Journal of Natural Products

Volumn 79, Issue 7, 2016, Pages 1828-1833

  Franchin, Marcelo ^a   Rosalen, Pedro Luiz ^a   Da Cunha, Marcos Guilherme ^a   Silva, Rangel Leal ^b   Colón, David F ^b   Bassi, Gabriel Shimizu ^b   De Alencar, Severino Matias ^b   Ikegaki, Masaharu ^c   Alves Filho, José C ^b   Cunha, Fernando Q ^b   Beutler, John A ^d   Cunha, Thiago Mattar ^b  

^a UNIVERSITY OF CAMPINAS   (Brazil)

^b UNIVERSITY OF SÃO PAULO   (Brazil)

^c FEDERAL UNIVERSITY OF ALFENAS   (Brazil)

^d NATIONAL CANCER INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIINFLAMMATORY AGENT; CINNAMOYLOXYMAMMEISIN; COUMARIN DERIVATIVE; CXCL2 CHEMOKINE; CYTOKINE; I KAPPA B ALPHA; IMMUNOGLOBULIN ENHANCER BINDING PROTEIN; LUCIFERASE; MACROPHAGE INFLAMMATORY PROTEIN 2; MITOGEN ACTIVATED PROTEIN KINASE; MITOGEN ACTIVATED PROTEIN KINASE 1; MITOGEN ACTIVATED PROTEIN KINASE 3; MITOGEN ACTIVATED PROTEIN KINASE P38; STRESS ACTIVATED PROTEIN KINASE; SYNAPTOTAGMIN I; TRANSCRIPTION FACTOR AP 1; TUMOR NECROSIS FACTOR ALPHA; UNCLASSIFIED DRUG; CINNAMOYLOXY-MAMMEISIN; CYCLOOXYGENASE 2; INDUCIBLE NITRIC OXIDE SYNTHASE; LIPOPOLYSACCHARIDE; MAMMEISIN; PROTEIN KINASE R; TUMOR NECROSIS FACTOR;

ANIMAL CELL; ANIMAL EXPERIMENT; ANTIINFLAMMATORY ACTIVITY; ARTICLE; ATTENUATION; CELL ISOLATION; CELL MIGRATION; CONTROLLED STUDY; CYTOKINE PRODUCTION; CYTOKINE RELEASE; DRUG ISOLATION; DRUG MECHANISM; ENZYME INHIBITION; EXPERIMENTAL ARTHRITIS; GENE EXPRESSION; GEOPROPOLIS; IN VITRO STUDY; IN VIVO STUDY; INFLAMMATION; JOINT CAVITY; MACROPHAGE; MALE; MEDICINAL PLANT; MOUSE; NEUTROPHIL; NONHUMAN; PERITONEAL CAVITY; PERITONEUM; PERITONITIS; PROTEIN DEGRADATION; PROTEIN PHOSPHORYLATION; REPORTER GENE; SIGNAL TRANSDUCTION; ANIMAL; ANTAGONISTS AND INHIBITORS; BRAZIL; CHEMICAL STRUCTURE; CHEMISTRY; DRUG EFFECTS; ISOLATION AND PURIFICATION; METABOLISM;

ANIMALS; ANTI-INFLAMMATORY AGENTS; BRAZIL; COUMARINS; CYCLOOXYGENASE 2; EIF-2 KINASE; LIPOPOLYSACCHARIDES; MACROPHAGES; MICE; MOLECULAR STRUCTURE; NF-KAPPA B; NITRIC OXIDE SYNTHASE TYPE II; P38 MITOGEN-ACTIVATED PROTEIN KINASES; SIGNAL TRANSDUCTION; TRANSCRIPTION FACTOR AP-1; TUMOR NECROSIS FACTOR-ALPHA;

EID: 84979518002     PISSN: 01633864     EISSN: 15206025     Source Type: Journal    
DOI: 10.1021/acs.jnatprod.6b00263     Document Type: Article

References (37)

1. Newman, D. J.; Cragg, G. M.; Snader, K. M. J. Nat. Prod. 2003, 66, 1022-1037 10.1021/np030096l
2. Newman, D. J.; Cragg, G. M. J. Nat. Prod. 2012, 75, 311-335 10.1021/np200906s
3. Musa, M. A.; Cooperwood, J. S.; Khan, M. O. Curr. Med. Chem. 2008, 15, 2664-2679 10.2174/092986708786242877
4. Ishita, I. J.; Nurul Islam, M.; Kim, Y. S.; Choi, R. J.; Sohn, H. S.; Jung, H. A.; Choi, J. S. Arch. Pharmacal Res. 2016, 39, 115-126 10.1007/s12272-015-0668-6
5. Niu, X.; Wang, Y.; Li, W.; Mu, Q.; Li, H.; Yao, H. et al. Int. Immunopharmacol. 2015, 24, 432-439 10.1016/j.intimp.2014.12.041
6. Xiong, Y.; Wang, J.; Yu, H.; Zhang, X.; Miao, C.; Ma, S. Immunopharmacol. Immunotoxicol. 2014, 36, 341-348 10.3109/08923973.2014.947035
7. Franchin, M.; Da Cunha, M. G.; Denny, C.; Napimoga, M. H.; Cunha, T. M.; Bueno-Silva, B.; Alencar, S. M.; Ikegaki, M.; Rosalen, P. L. Evid. Based. Complement. Alternat. Med. 2013, 2013, 1-9 10.1155/2013/907041
8. Da Cunha, M. G.; Rosalen, P. L.; Franchin, M.; de Alencar, S. M.; Ikegaki, M.; Ransom, T.; Beutler, J. A. Planta Med. 2016, 82, 190-194 10.1055/s-0035-1558142
9. Ribeiro-Junior, J. A.; Franchin, M.; Cavallini, M. E.; Denny, C.; Alencar, S. M.; Ikegaki, M.; Rosalen, P. L. Evid. Based. Complement. Alternat. Med. 2015, 2015, 1-5 10.1155/2015/459846
10. Park, Y. K.; Alencar, S. M.; Aguiar, C. L. J. Agric. Food Chem. 2002, 50, 2502-2506 10.1021/jf011432b
11. Silva, B. B.; Rosalen, P. L.; Cury, J. A.; Ikegaki, M.; Souza, V. C.; Esteves, A.; Alencar, S. M. Evid. Based. Complement. Alternat. Med. 2008, 5, 313-316 10.1093/ecam/nem059
12. Natarajan, K.; Singh, S.; Burke, T. R., Jr.; Grunberger, D.; Aggarwal, B. B. Proc. Natl. Acad. Sci. U. S. A. 1996, 93, 9090-9095 10.1073/pnas.93.17.9090
13. Paulino, N.; Abreu, S. R.; Uto, Y.; Koyama, D.; Nagasawa, H.; Hori, H.; Dirsch, V. M.; Vollmar, A. M.; Scremin, A.; Bretz, W. A. Eur. J. Pharmacol. 2008, 587, 296-301 10.1016/j.ejphar.2008.02.067
14. Koo, H.; Hayacibara, M. F.; Schobel, B. D.; Cury, J. A.; Rosalen, P. L.; Park, Y. K.; Vacca-Smith, A. M.; Bowen, W. H. J. Antimicrob. Chemother. 2003, 52, 782-789 10.1093/jac/dkg449
15. Koo, H.; Rosalen, P. L.; Cury, J. A.; Park, Y. K.; Ikegaki, M.; Sattler, A. Caries Res. 1999, 33, 393-400 10.1159/000016539
16. Sforcin, J. M.; Bankova, V. J. Ethnopharmacol. 2011, 133, 253-260 10.1016/j.jep.2010.10.032
17. Wynn, T. A.; Chawla, A.; Pollard, J. W. Nature 2013, 496, 445-455 10.1038/nature12034
18. Davies, L. C.; Jenkins, S. J.; Allen, J. E.; Taylor, P. R. Nat. Immunol. 2013, 14, 986-995 10.1038/ni.2705
19. Kim, E. K.; Choi, E. J. Biochim. Biophys. Acta, Mol. Basis Dis. 2010, 1802, 396-405 10.1016/j.bbadis.2009.12.009
20. Arthur, J. S.; Ley, S. C. Nat. Rev. Immunol. 2013, 13, 679-692 10.1038/nri3495
21. Dumitru, C. D.; Ceci, J. D.; Tsatsanis, C.; Kontoyiannis, D.; Stamatakis, K.; Lin, J. H.; Patriotis, C.; Jenkins, N. A.; Copeland, N. G.; Kollias, G.; Tsichlis, P. N. Cell 2000, 103, 1071-1083 10.1016/S0092-8674(00)00210-5
22. Karin, M. J. Biol. Chem. 1995, 270, 16483-16486 10.1074/jbc.270.28.16483
23. Zarubin, T.; Han, J. Cell Res. 2005, 15, 11-18 10.1038/sj.cr.7290257
24. Li, Q.; Verma, I. M. Nat. Rev. Immunol. 2002, 2, 725-734 10.1038/nri910
25. Auphan, N.; DiDonato, J. A.; Rosette, C.; Helmberg, A.; Karin, M. Science 1995, 270, 286-290 10.1126/science.270.5234.286
26. Olson, C. M.; Hedrick, M. N.; Izadi, H.; Bates, T. C.; Oliveira, E. R.; Anguita, J. Infect. Immun. 2007, 75, 270-277 10.1128/IAI.01412-06
27. Reber, L.; Vermeulen, L.; Haegeman, G.; Frossard, N. PLoS One 2009, 4, e4393 10.1371/journal.pone.0004393
28. Liu, F.; Sun, G. Q.; Gao, H. Y.; Li, R. S.; Soromou, L. W.; Chen, N.; Deng, Y. H.; Feng, H. H. J. Surg. Res. 2013, 185, 300-309 10.1016/j.jss.2013.05.083
29. Guo, W.; Sun, J.; Jiang, L.; Duan, L.; Huo, M.; Chen, N.; Zhong, W.; Wassy, L.; Yang, Z.; Feng, H. Inflammation 2012, 35, 1764-1772 10.1007/s10753-012-9495-9
30. Dal Secco, D.; Moreira, A. P.; Freitas, A.; Silva, J. S.; Rossi, M. A.; Ferreira, S. H.; Cunha, F. Q. Nitric Oxide 2006, 15, 77-86 10.1016/j.niox.2006.02.004
31. Baez, S. Circ. Res. 1969, 25, 315-329 10.1161/01.RES.25.3.315
32. Fortes, Z. B.; Farsky, S. P.; Oliveira, M. A.; Garcia-Leme, J. Diabetes 1991, 40, 1267-1273 10.2337/diab.40.10.1267
33. Vieira, S. M.; Lemos, H. P.; Grespan, R.; Napimoga, M. H.; Dal-Secco, D.; Freitas, A.; Cunha, T. M.; Verri, W. A., Jr.; Souza-Junior, D. A.; Jamur, M. C.; Fernandes, K. S.; Oliver, C.; Silva, J. S.; Teixeira, M. M.; Cunha, F. Q. Br. J. Pharmacol. 2009, 158, 779-789 10.1111/j.1476-5381.2009.00367.x
34. Veras, F. P.; Peres, R. S.; Saraiva, A. L.; Pinto, L. G.; Louzada-Junior, P.; Cunha, T. M.; Paschoal, J. A.; Cunha, F. Q.; Alves-Filho, J. C. Sci. Rep. 2015, 5, 15171 10.1038/srep15171
35. Vermes, I.; Haanen, C.; Steffens-Nakken, H.; Reutellingsperger, C. J. Immunol. Methods 1995, 184, 39-51 10.1016/0022-1759(95)00072-I
36. Cooper, Z. A.; Ghosh, A.; Gupta, A.; Maity, T.; Benjamin, I. J.; Vogel, S. N.; Hasday, J. D.; Singh, I. S. Am. J. Physiol. Cell. Physiol. 2010, 298, C171-C181 10.1152/ajpcell.00346.2009
37. Silva, R. L.; Lopes, A. H.; França, R. O.; Vieira, S. M.; Silva, E. C.; Amorim, R. C.; Cunha, F. Q.; Pohlit, A. M.; Cunha, T. M. J. Nat. Prod. 2015, 78, 241-249 10.1021/np500796f