Intracellular signaling pathways modulated by phenolic compounds: Application for new anti-inflammatory drugs discovery

Current Medicinal Chemistry

Volumn 19, Issue 18, 2012, Pages 2876-2900

  Costa, G ^a   Francisco, V ^a,b   Lopes, M C ^a,b   Cruz, M T ^a,b   Batista, M T ^a  

^a UNIVERSITY OF COIMBRA   (Portugal)

^b UNIVERSITY OF COIMBRA   (Portugal)

Author keywords

Chemokines; Cytokines; Drug discovery; Flavonoids; Inflammation; Intracellular signaling pathways; Mitogen activated protein kinase; Natural compounds; Nitric oxide; Phenolic compounds; Proteasome; Structure activity relationship; Transcription factor

Indexed keywords

ANTHRAQUINONE DERIVATIVE; ANTIINFLAMMATORY AGENT; BENZOIC ACID DERIVATIVE; CINNAMIC ACID DERIVATIVE; COUMARIN DERIVATIVE; IMMUNOGLOBULIN ENHANCER BINDING PROTEIN; LEUKOTRIENE; LIGNAN DERIVATIVE; METHANOL DERIVATIVE; MITOGEN ACTIVATED PROTEIN KINASE; NITRIC OXIDE; PEROXISOME PROLIFERATOR ACTIVATED RECEPTOR; PHENOL DERIVATIVE; PHOSPHATIDYLINOSITOL 3 KINASE; PROSTAGLANDIN; PROTEASOME; PROTEIN KINASE B; STILBENE DERIVATIVE; TANNIN DERIVATIVE; TRANSCRIPTION FACTOR AP 1; TRANSCRIPTION FACTOR NRF2; UBIQUITIN;

ANTIINFLAMMATORY ACTIVITY; ARTICLE; CELLULAR STRESS RESPONSE; DIMERIZATION; DRUG CLASSIFICATION; DRUG ISOLATION; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME ACTIVITY; ENZYME PHOSPHORYLATION; INNATE IMMUNITY; INTRACELLULAR SIGNALING; MEDIATOR RELEASE; PROTEIN DEGRADATION; PROTEIN FUNCTION; PROTEIN INDUCTION; STRUCTURE ACTIVITY RELATION;

EID: 84861917656     PISSN: 09298673     EISSN: 1875533X     Source Type: Journal    
DOI: 10.2174/092986712800672049     Document Type: Article

References (169)

1. Yoon, J.H.; Baek, S.J. Molecular targets of dietary polyphenols with antiinflammatory properties. Yonsei Med. J., 2005, 46(5), 585-596.
2. Santangelo, C.; Vari, R.; Scazzocchio, B.; Di Benedetto, R.; Filesi, C.; Masella, R. Polyphenols, intracellular signaling and inflammation. Ann. Ist. Super. Sanita, 2007, 43(4), 394-405.
3. O'Neill, L.A. Targeting signal transduction as a strategy to treat inflammatory diseases. Nat. Rev. Drug Discov., 2006, 5(7), 549-563.
4. Molina, M.F.; Sanchez-Reus, I.; Iglesias, I.; Benedi, J. Quercetin, a flavonoid antioxidant, prevents and protects against ethanol-induced oxidative stress in mouse liver. Biol. Pharm. Bull., 2003, 26(10), 1398-1402.
5. Cabrini, L.; Barzanti, V.; Cipollone, M.; Fiorentini, D.; Grossi, G.; Tolomelli, B.; Zambonin, L.; Landi, L. Antioxidants and total peroxyl radical-trapping ability of olive and seed oils. J. Agric. Food Chem., 2001, 49(12), 6026-6032.
6. de la Torre, R.; Covas, M.I.; Pujadas, M.A.; Fito, M.; Farre, M. Is dopamine behind the health benefits of red wine? Eur. J. Nutr., 2006, 45(5), 307-310.
7. Shahidi, F.; Naczk, M. Food phenolics, sources, chemistry, effects, applications; Technomic Publishing Co Inc: Lancaster, 1995.
8. Vitaglione, P.; Donnarumma, G.; Napolitano, A.; Galvano, F.; Gallo, A.; Scalfi, L.; Fogliano, V. Protocatechuic acid is the major human metabolite of cyanidin-glucosides. J. Nutr., 2007, 137(9), 2043-2048.
9. Clifford, M.N. Chlorogenic acids and other cinnamates - nature, occurrence, dietary burden, absorption and metabolism. Journal of the Science of Food and Agriculture, 2000, 80(7), 1033-1043.
10. D'Archivio, M.; Filesi, C.; Di Benedetto, R.; Gargiulo, R.; Giovannini, C.; Masella, R. Polyphenols, dietary sources and bioavailability. Ann. Ist. Super. Sanita, 2007, 43(4), 348-361.
11. Zhang, Y.; Liu, Y.; Wang, T.; Li, B.; Li, H.; Wang, Z.; Yang, B. Resveratrol, a natural ingredient of grape skin: antiarrhythmic efficacy and ionic mechanisms. Biochem. Biophys. Res. Commun., 2006, 340(4), 1192-1199.
12. Beecher, G.R. Overview of dietary flavonoids: nomenclature, occurrence and intake. J Nutr, 2003, 133(10), 3248S-3254S.
13. Gomes, A.; Fernandes, E.; Lima, J.L.; Mira, L.; Corvo, M.L. Molecular mechanisms of anti-inflammatory activity mediated by flavonoids. Curr. Med. Chem., 2008, 15(16), 1586-1605.
14. Manach, C.; Williamson, G.; Morand, C.; Scalbert, A.; Remesy, C. Bioavailability and bioefficacy of polyphenols in humans. I. Review of 97 bioavailability studies. Am. J. Clin. Nutr., 2005, 81(1 Suppl), 230S-242S.
15. Markham, K.R. Techniques of flavonoids identification; Academic Press: 1982.
16. Rangkadilok, N.; Sitthimonchai, S.; Worasuttayangkurn, L.; Mahidol, C.; Ruchirawat, M.; Satayavivad, J. Evaluation of free radical scavenging and antityrosinase activities of standardized longan fruit extract. Food Chem. Toxicol., 2007, 45(2), 328-336.
17. Huang, W.Y.; Cai, Y.Z.; Zhang, Y. Natural phenolic compounds from medicinal herbs and dietary plants: potential use for cancer prevention. Nutr. Cancer, 2009, 62(1), 1-20.
18. Manna, S.K.; Mukhopadhyay, A.; Aggarwal, B.B. Resveratrol suppresses TNF-induced activation of nuclear transcription factors NF-kappa B, activator protein-1, and apoptosis: potential role of reactive oxygen intermediates and lipid peroxidation. J. Immunol., 2000, 164(12), 6509-6519.
19. Son, P.S.; Park, S.A.; Na, H.K.; Jue, D.M.; Kim, S.; Surh, Y.J. Piceatannol, a catechol-type polyphenol, inhibits phorbol ester-induced NF-{kappa}B activation and cyclooxygenase-2 expression in human breast epithelial cells: cysteine 179 of IKK{beta} as a potential target. Carcinogenesis, 2010, 31(8), 1442-1449.
20. Hou, D.X.; Luo, D.; Tanigawa, S.; Hashimoto, F.; Uto, T.; Masuzaki, S.; Fujii, M.; Sakata, Y. Prodelphinidin B-4 3'-O-gallate, a tea polyphenol, is involved in the inhibition of COX-2 and iNOS via the downregulation of TAK1-NF-kappaB pathway. Biochem. Pharmacol., 2007, 74(5), 742-751.
21. Lo, A.H.; Liang, Y.C.; Lin-Shiau, S.Y.; Ho, C.T.; Lin, J.K. Carnosol, an antioxidant in rosemary, suppresses inducible nitric oxide synthase through down-regulating nuclear factor-kappaB in mouse macrophages. Carcinogenesis, 2002, 23(6), 983-991.
22. Liang, Y.C.; Huang, Y.T.; Tsai, S.H.; Lin-Shiau, S.Y.; Chen, C.F.; Lin, J.K. Suppression of inducible cyclooxygenase and inducible nitric oxide synthase by apigenin and related flavonoids in mouse macrophages. Carcinogenesis, 1999, 20(10), 1945-1952.
23. Chen, C.C.; Chow, M.P.; Huang, W.C.; Lin, Y.C.; Chang, Y.J. Flavonoids inhibit tumor necrosis factor-alpha-induced up-regulation of intercellular adhesion molecule-1 (ICAM-1) in respiratory epithelial cells through activator protein-1 and nuclear factor-kappaB: structure-activity relationships. Mol. Pharmacol., 2004, 66(3), 683-693.
24. Suh, S.J.; Chung, T.W.; Son, M.J.; Kim, S.H.; Moon, T.C.; Son, K.H.; Kim, H.P.; Chang, H.W.; Kim, C.H. The naturally occurring biflavonoid, ochnaflavone, inhibits LPS-induced iNOS expression, which is mediated by ERK1/2 via NF-kappaB regulation, in RAW264.7 cells. Arch. Biochem. Biophys., 2006, 447(2), 136-146.
25. Chen, J.C.; Ho, F.M.; Pei-Dawn Lee, C.; Chen, C.P.; Jeng, K.C.; Hsu, H.B.; Lee, S.T.; Wen Tung, W.; Lin, W.W. Inhibition of iNOS gene expression by quercetin is mediated by the inhibition of IkappaB kinase, nuclear factorkappa B and STAT1, and depends on heme oxygenase-1 induction in mouse BV-2 microglia. Eur. J. Pharmacol., 2005, 521(1-3), 9-20.
26. Manna, S.K.; Aggarwal, R.S.; Sethi, G.; Aggarwal, B.B.; Ramesh, G.T. Morin (3,5,7,2',4'-Pentahydroxyflavone) abolishes nuclear factor-kappaB activation induced by various carcinogens and inflammatory stimuli, leading to suppression of nuclear factor-kappaB-regulated gene expression and upregulation of apoptosis. Clin. Cancer Res., 2007, 13(7), 2290-2297.
27. Aneja, R.; Hake, P.W.; Burroughs, T.J.; Denenberg, A.G.; Wong, H.R.; Zingarelli, B. Epigallocatechin, a green tea polyphenol, attenuates myocardial ischemia reperfusion injury in rats. Mol. Med., 2004, 10(1-6), 55-62.
28. Mackenzie, G.G.; Carrasquedo, F.; Delfino, J.M.; Keen, C.L.; Fraga, C.G.; Oteiza, P.I. Epicatechin, catechin, and dimeric procyanidins inhibit PMAinduced NF-kappaB activation at multiple steps in Jurkat T cells. FASEB J., 2004, 18(1), 167-169.
29. Pan, M.H.; Hsieh, M.C.; Hsu, P.C.; Ho, S.Y.; Lai, C.S.; Wu, H.; Sang, S.; Ho, C.T. 6-Shogaol suppressed lipopolysaccharide-induced up-expression of iNOS and COX-2 in murine macrophages. Mol. Nutr. Food Res., 2008, 52(12), 1467-1477.
30. Pan, M.H.; Lai, C.S.; Wang, Y.J.; Ho, C.T. Acacetin suppressed LPSinduced up-expression of iNOS and COX-2 in murine macrophages and TPA-induced tumor promotion in mice. Biochem. Pharmacol., 2006, 72(10), 1293-1303.
31. Chen, S.R.; Xu, X.Z.; Wang, Y.H.; Chen, J.W.; Xu, S.W.; Gu, L.Q.; Liu, P.Q. Icariin derivative inhibits inflammation through suppression of p38 mitogen-activated protein kinase and nuclear factor-kappaB pathways. Biol. Pharm. Bull., 2010, 33(8), 1307-1313.
32. Kundu, J.K.; Surh, Y.J. Epigallocatechin gallate inhibits phorbol esterinduced activation of NF-kappa B and CREB in mouse skin: role of p38 MAPK. Ann. N. Y. Acad. Sci., 2007, 1095, 504-512.
33. Zhang, Y.; Lian, F.; Zhu, Y.; Xia, M.; Wang, Q.; Ling, W.; Wang, X.D. Cyanidin-3-O-beta-glucoside inhibits LPS-induced expression of inflammatory mediators through decreasing IkappaBalpha phosphorylation in THP-1 cells. Inflamm Res, 2010, 59(9), 723-730.
34. Erdelyi, K.; Kiss, A.; Bakondi, E.; Bai, P.; Szabo, C.; Gergely, P.; Erdodi, F.; Virag, L. Gallotannin inhibits the expression of chemokines and inflammatory cytokines in A549 cells. Mol. Pharmacol., 2005, 68(3), 895-904.
35. Moon, M.K.; Lee, Y.J.; Kim, J.S.; Kang, D.G.; Lee, H.S. Effect of caffeic acid on tumor necrosis factor-alpha-induced vascular inflammation in human umbilical vein endothelial cells. Biol. Pharm. Bull., 2009, 32(8), 1371-1377.
36. Han, J.M.; Jin, Y.Y.; Kim, H.Y.; Park, K.H.; Lee, W.S.; Jeong, T.S. Lavandulyl flavonoids from Sophora flavescens suppress lipopolysaccharideinduced activation of nuclear factor-kappaB and mitogen-activated protein kinases in RAW264.7 cells. Biol. Pharm. Bull., 2010, 33(6), 1019-1023.
37. Chen, Y.; Yang, L.; Lee, T.J. Oroxylin A inhibition of lipopolysaccharideinduced iNOS and COX-2 gene expression via suppression of nuclear factorkappaB activation. Biochem. Pharmacol., 2000, 59(11), 1445-1457.
38. Min, Y.D.; Choi, C.H.; Bark, H.; Son, H.Y.; Park, H.H.; Lee, S.; Park, J.W.; Park, E.K.; Shin, H.I.; Kim, S.H. Quercetin inhibits expression of inflammatory cytokines through attenuation of NF-kappaB and p38 MAPK in HMC-1 human mast cell line. Inflamm. Res., 2007, 56(5), 210-215.
39. Oh, G.S.; Pae, H.O.; Choi, B.M.; Lee, H.S.; Kim, I.K.; Yun, Y.G.; Kim, J.D.; Chung, H.T. Penta-O-galloyl-beta-D-glucose inhibits phorbol myristate acetate-induced interleukin-8 gene expression in human monocytic U937 cells through its inactivation of nuclear factor-kappa B. Int. Immunopharmacol., 2004, 4(3), 377-386.
40. Kim, S.J.; Kim, M.C.; Lee, B.J.; Park, D.H.; Hong, S.H.; Um, J.Y. Anti- Inflammatory activity of chrysophanol through the suppression of NFkappaB/caspase-1 activation in vitro and in vivo. Molecules, 2010, 15(9), 6436-6451.
41. Kumar, A.; Dhawan, S.; Aggarwal, B.B. Emodin (3-methyl-1,6,8- trihydroxyanthraquinone) inhibits TNF-induced NF-kappaB activation, IkappaB degradation, and expression of cell surface adhesion proteins in human vascular endothelial cells. Oncogene, 1998, 17(7), 913-918.
42. Choi, J.S.; Choi, Y.J.; Park, S.H.; Kang, J.S.; Kang, Y.H. Flavones mitigate tumor necrosis factor-alpha-induced adhesion molecule upregulation in cultured human endothelial cells: role of nuclear factor-kappa B. J. Nutr., 2004, 134(5), 1013-1019.
43. Xu, C.Q.; Liu, B.J.; Wu, J.F.; Xu, Y.C.; Duan, X.H.; Cao, Y.X.; Dong, J.C. Icariin attenuates LPS-induced acute inflammatory responses: involvement of PI3K/Akt and NF-kappaB signaling pathway. Eur. J. Pharmacol., 2010, 642(1-3), 146-153.
44. De Stefano, D.; Maiuri, M.C.; Simeon, V.; Grassia, G.; Soscia, A.; Cinelli, M.P.; Carnuccio, R. Lycopene, quercetin and tyrosol prevent macrophage activation induced by gliadin and IFN-gamma. Eur. J. Pharmacol., 2007, 566(1-3), 192-199.
45. Carluccio, M.A.; Siculella, L.; Ancora, M.A.; Massaro, M.; Scoditti, E.; Storelli, C.; Visioli, F.; Distante, A.; De Caterina, R. Olive oil and red wine antioxidant polyphenols inhibit endothelial activation: antiatherogenic properties of Mediterranean diet phytochemicals. Arterioscler. Thromb. Vasc. Biol., 2003, 23(4), 622-629.
46. Kang, G.; Kong, P.J.; Yuh, Y.J.; Lim, S.Y.; Yim, S.V.; Chun, W.; Kim, S.S. Curcumin suppresses lipopolysaccharide-induced cyclooxygenase-2 expression by inhibiting activator protein 1 and nuclear factor kappab bindings in BV2 microglial cells. J. Pharmacol. Sci., 2004, 94(3), 325-328.
47. Chan, M.M. Inhibition of tumor necrosis factor by curcumin, a phytochemical. Biochem. Pharmacol., 1995, 49(11), 1551-1556.
48. Park, S.H.; Kang, J.S.; Yoon, Y.D.; Lee, K.; Kim, K.J.; Lee, K.H.; Lee, C.W.; Moon, E.Y.; Han, S.B.; Kim, B.H.; Kim, H.M.; Park, S.K. Glabridin inhibits lipopolysaccharide-induced activation of a microglial cell line, BV-2, by blocking NF-kappaB and AP-1. Phytother. Res., 2010, 24 Suppl 1, S29-34.
49. Woo, K.J.; Lim, J.H.; Suh, S.I.; Kwon, Y.K.; Shin, S.W.; Kim, S.C.; Choi, Y.H.; Park, J.W.; Kwon, T.K. Differential inhibitory effects of baicalein and baicalin on LPS-induced cyclooxygenase-2 expression through inhibition of C/EBPbeta DNA-binding activity. Immunobiology, 2006, 211(5), 359-368.
50. Ichikawa, D.; Matsui, A.; Imai, M.; Sonoda, Y.; Kasahara, T. Effect of various catechins on the IL-12p40 production by murine peritoneal macrophages and a macrophage cell line, J774.1. Biol. Pharm. Bull., 2004, 27(9), 1353-1358.
51. Lim, J.H.; Kwon, T.K. Curcumin inhibits phorbol myristate acetate (PMA)- induced MCP-1 expression by inhibiting ERK and NF-kappaB transcriptional activity. Food Chem. Toxicol., 2010, 48(1), 47-52.
52. Donnelly, L.E.; Newton, R.; Kennedy, G.E.; Fenwick, P.S.; Leung, R.H.; Ito, K.; Russell, R.E.; Barnes, P.J. Anti-inflammatory effects of resveratrol in lung epithelial cells: molecular mechanisms. Am. J. Physiol. Lung. Cell. Mol. Physiol., 2004, 287(4), L774-783.
53. Schonthaler, H.B.; Guinea-Viniegra, J.; Wagner, E.F. Targeting inflammation by modulating the Jun/AP-1 pathway. Ann. Rheum. Dis., 2011, 70 Suppl 1, i109-112.
54. Karin, M. The regulation of AP-1 activity by mitogen-activated protein kinases. J. Biol. Chem., 1995, 270(28), 16483-16486.
55. Stein, B.; Baldwin, A.S., Jr.; Ballard, D.W.; Greene, W.C.; Angel, P.; Herrlich, P. Cross-coupling of the NF-kappa B p65 and Fos/Jun transcription factors produces potentiated biological function. EMBO J., 1993, 12(10), 3879-3891.
56. Hirano, T.; Higa, S.; Arimitsu, J.; Naka, T.; Ogata, A.; Shima, Y.; Fujimoto, M.; Yamadori, T.; Ohkawara, T.; Kuwabara, Y.; Kawai, M.; Matsuda, H.; Yoshikawa, M.; Maezaki, N.; Tanaka, T.; Kawase, I. Luteolin, a flavonoid, inhibits AP-1 activation by basophils. Biochem. Biophys. Res. Commun., 2006, 340(1), 1-7.
57. Wadsworth, T.L.; McDonald, T.L.; Koop, D.R. Effects of Ginkgo biloba extract (EGb 761) and quercetin on lipopolysaccharide-induced signaling pathways involved in the release of tumor necrosis factor-alpha. Biochem. Pharmacol., 2001, 62(7), 963-974.
58. Kim, A.R.; Cho, J.Y.; Zou, Y.; Choi, J.S.; Chung, H.Y. Flavonoids differentially modulate nitric oxide production pathways in lipopolysaccharide- activated RAW264.7 cells. Arch. Pharm. Res., 2005, 28(3), 297-304.
59. Maggi-Capeyron, M.F.; Ceballos, P.; Cristol, J.P.; Delbosc, S.; Le Doucen, C.; Pons, M.; Leger, C.L.; Descomps, B. Wine phenolic antioxidants inhibit AP-1 transcriptional activity. J. Agric. Food. Chem., 2001, 49(11), 5646-5652.
60. Lee, J.Y.; Woo, E.R.; Kang, K.W. Inhibition of lipopolysaccharide- inducible nitric oxide synthase expression by acteoside through blocking of AP-1 activation. J. Ethnopharmacol., 2005, 97(3), 561-566.
61. Hwang, M.K.; Song, N.R.; Kang, N.J.; Lee, K.W.; Lee, H.J. Activation of phosphatidylinositol 3-kinase is required for tumor necrosis factor-alphainduced upregulation of matrix metalloproteinase-9: its direct inhibition by quercetin. Int. J. Biochem. Cell. Biol., 2009, 41(7), 1592-1600.
62. Becker, J.; Delayre-Orthez, C.; Frossard, N.; Pons, F. Regulation of inflammation by PPARs: a future approach to treat lung inflammatory diseases? Fundam. Clin. Pharmacol., 2006, 20(5), 429-447.
63. Blanquart, C.; Barbier, O.; Fruchart, J.C.; Staels, B.; Glineur, C. Peroxisome proliferator-activated receptors: regulation of transcriptional activities and roles in inflammation. J. Steroid Biochem. Mol. Biol., 2003, 85(2-5), 267-273.
64. Dubuquoy, L.; Rousseaux, C.; Thuru, X.; Peyrin-Biroulet, L.; Romano, O.; Chavatte, P.; Chamaillard, M.; Desreumaux, P. PPARgamma as a new therapeutic target in inflammatory bowel diseases. Gut, 2006, 55(9), 1341-1349.
65. Esposito, E.; Mazzon, E.; Paterniti, I.; Dal Toso, R.; Pressi, G.; Caminiti, R.; Cuzzocrea, S. PPAR-alpha Contributes to the Anti-Inflammatory Activity of Verbascoside in a Model of Inflammatory Bowel Disease in Mice. PPAR Res., 2010, 2010, 917312.
66. Zhang, M.; Deng, C.; Zheng, J.; Xia, J.; Sheng, D. Curcumin inhibits trinitrobenzene sulphonic acid-induced colitis in rats by activation of peroxisome proliferator-activated receptor gamma. Int. Immunopharmacol., 2006, 6(8), 1233-1242.
67. Valles, S.L.; Dolz-Gaiton, P.; Gambini, J.; Borras, C.; Lloret, A.; Pallardo, F.V.; Vina, J. Estradiol or genistein prevent Alzheimer's disease-associated inflammation correlating with an increase PPAR gamma expression in cultured astrocytes. Brain Res., 2010, 1312, 138-144.
68. Salam, N.K.; Huang, T.H.; Kota, B.P.; Kim, M.S.; Li, Y.; Hibbs, D.E. Novel PPAR-gamma agonists identified from a natural product library: a virtual screening, induced-fit docking and biological assay study. Chem. Biol. Drug Des., 2008, 71(1), 57-70.
69. Favreau, L.V.; Pickett, C.B. The rat quinone reductase antioxidant response element. Identification of the nucleotide sequence required for basal and inducible activity and detection of antioxidant response element-binding proteins in hepatoma and non-hepatoma cell lines. J. Biol. Chem., 1995, 270(41), 24468-24474.
70. Rushmore, T.H.; King, R.G.; Paulson, K.E.; Pickett, C.B. Regulation of glutathione S-transferase Ya subunit gene expression: identification of a unique xenobiotic-responsive element controlling inducible expression by planar aromatic compounds. PNAS, 1990, 87(10), 3826-3830.
71. Chan, K.; Kan, Y.W. Nrf2 is essential for protection against acute pulmonary injury in mice. PNAS, 1999, 96(22), 12731-12736.
72. Kim, Y.C.; Masutani, H.; Yamaguchi, Y.; Itoh, K.; Yamamoto, M.; Yodoi, J. Hemin-induced activation of the thioredoxin gene by Nrf2. A differential regulation of the antioxidant responsive element by a switch of its binding factors. J. Biol. Chem., 2001, 276(21), 18399-18406.
73. Inamdar, N.M.; Ahn, Y.I.; Alam, J. The heme-responsive element of the mouse heme oxygenase-1 gene is an extended AP-1 binding site that resembles the recognition sequences for MAF and NF-E2 transcription factors. Biochem. Biophys. Res. Commun., 1996, 221(3), 570-576.
74. Tsuji, Y.; Ayaki, H.; Whitman, S.P.; Morrow, C.S.; Torti, S.V.; Torti, F.M. Coordinate transcriptional and translational regulation of ferritin in response to oxidative stress. Mol. Cell. Biol., 2000, 20(16), 5818-5827.
75. Kim, J.; Cha, Y.N.; Surh, Y.J. A protective role of nuclear factor-erythroid 2- related factor-2 (Nrf2) in inflammatory disorders. Mutat. Res., 2010, 690(1-2), 12-23.
76. Balogun, E.; Hoque, M.; Gong, P.; Killeen, E.; Green, C.J.; Foresti, R.; Alam, J.; Motterlini, R. Curcumin activates the haem oxygenase-1 gene via regulation of Nrf2 and the antioxidant-responsive element. Biochem. J., 2003, 371(Pt 3), 887-895.
77. Tanigawa, S.; Fujii, M.; Hou, D.X. Action of Nrf2 and Keap1 in AREmediated NQO1 expression by quercetin. Free Radic. Biol. Med., 2007, 42(11), 1690-1703.
78. Chen, C.; Yu, R.; Owuor, E.D.; Kong, A.N. Activation of antioxidantresponse element (ARE), mitogen-activated protein kinases (MAPKs) and caspases by major green tea polyphenol components during cell survival and death. Arch. Pharm. Res., 2000, 23(6), 605-612.
79. Vari, R.; D'Archivio, M.; Filesi, C.; Carotenuto, S.; Scazzocchio, B.; Santangelo, C.; Giovannini, C.; Masella, R. Protocatechuic acid induces antioxidant/detoxifying enzyme expression through JNK-mediated Nrf2 activation in murine macrophages. J. Nutr. Biochem., 2011, 22(5), 409-417.
80. Page, T.H.; Smolinska, M.; Gillespie, J.; Urbaniak, A.M.; Foxwell, B.M. Tyrosine kinases and inflammatory signaling. Curr. Mol. Med., 2009, 9(1), 69-85.
81. Lee, K.M.; Lee, K.W.; Jung, S.K.; Lee, E.J.; Heo, Y.S.; Bode, A.M.; Lubet, R.A.; Lee, H.J.; Dong, Z. Kaempferol inhibits UVB-induced COX-2 expression by suppressing Src kinase activity. Biochem. Pharmacol., 2010, 80(12), 2042-2049.
82. Byun, S.; Lee, K.W.; Jung, S.K.; Lee, E.J.; Hwang, M.K.; Lim, S.H.; Bode, A.M.; Lee, H.J.; Dong, Z. Luteolin inhibits protein kinase C(epsilon) and c- Src activities and UVB-induced skin cancer. Cancer. Res., 2010, 70(6), 2415-2423.
83. Gururajan, M.; Dasu, T.; Shahidain, S.; Jennings, C.D.; Robertson, D.A.; Rangnekar, V.M.; Bondada, S. Spleen tyrosine kinase (Syk), a novel target of curcumin, is required for B lymphoma growth. J. Immunol., 2007, 178(1), 111-121.
84. Shichijo, M.; Yamamoto, N.; Tsujishita, H.; Kimata, M.; Nagai, H.; Kokubo, T. Inhibition of syk activity and degranulation of human mast cells by flavonoids. Biol. Pharm. Bull., 2003, 26(12), 1685-1690.
85. Kumamoto, T.; Fujii, M.; Hou, D.X. Myricetin directly targets JAK1 to inhibit cell transformation. Cancer Lett., 2009, 275(1), 17-26.
86. Owuor, E.D.; Kong, A.N. Antioxidants and oxidants regulated signal transduction pathways. Biochem. Pharmacol., 2002, 64(5-6), 765-770.
87. Broom, O.J.; Widjaya, B.; Troelsen, J.; Olsen, J.; Nielsen, O.H. Mitogen activated protein kinases: a role in inflammatory bowel disease? Clin. Exp. Immunol., 2009, 158(3), 272-280.
88. Kaminska, B. MAPK signaling pathways as molecular targets for antiinflammatory therapy - from molecular mechanisms to therapeutic benefits. Biochim. Biophys. Acta, 2005, 1754 (1-2), 253-262.
89. Camacho-Barquero, L.; Villegas, I.; Sanchez-Calvo, J.M.; Talero, E.; Sanchez-Fidalgo, S.; Motilva, V.; Alarcon de la Lastra, C. Curcumin, a Curcuma longa constituent, acts on MAPK p38 pathway modulating COX-2 and iNOS expression in chronic experimental colitis. Int. Immunopharmacol., 2007, 7(3), 333-342.
90. Xagorari, A.; Roussos, C.; Papapetropoulos, A. Inhibition of LPS-stimulated pathways in macrophages by the flavonoid luteolin. Br. J. Pharmacol., 2002, 136(7), 1058-1064.
91. Cho, S.Y.; Park, S.J.; Kwon, M.J.; Jeong, T.S.; Bok, S.H.; Choi, W.Y.; Jeong, W.I.; Ryu, S.Y.; Do, S.H.; Lee, C.S.; Song, J.C.; Jeong, K.S. Quercetin suppresses proinflammatory cytokines production through MAP kinases andNF-kappaB pathway in lipopolysaccharide-stimulated macrophage. Mol. Cell. Biochem., 2003, 243(1-2), 153-160.
92. Kandere-Grzybowska, K.; Kempuraj, D.; Cao, J.; Cetrulo, C.L.; Theoharides, T.C. Regulation of IL-1-induced selective IL-6 release from human mast cells and inhibition by quercetin. Br. J. Pharmacol., 2006, 148(2), 208-215.
93. Pergola, C.; Rossi, A.; Dugo, P.; Cuzzocrea, S.; Sautebin, L. Inhibition of nitric oxide biosynthesis by anthocyanin fraction of blackberry extract. Nitric Oxide, 2006, 15(1), 30-39.
94. Fougerat, A.; Gayral, S.; Malet, N.; Briand-Mesange, F.; Breton-Douillon, M.; Laffargue, M. Phosphoinositide 3-kinases and their role in inflammation: potential clinical targets in atherosclerosis? Clin. Sci. (Lond.), 2009, 116(11), 791-804.
95. Marone, R.; Cmiljanovic, V.; Giese, B.; Wymann, M.P. Targeting phosphoinositide 3-kinase: moving towards therapy. Biochim. Biophys. Acta, 2008, 1784(1), 159-185.
96. Elliott, P.J.; Zollner, T.M.; Boehncke, W.H. Proteasome inhibition: a new anti-inflammatory strategy. J. Mol. Med., 2003, 81(4), 235-245.
97. Nguyen, T.; Sherratt, P.J.; Huang, H.C.; Yang, C.S.; Pickett, C.B. Increased protein stability as a mechanism that enhances Nrf2-mediated transcriptional activation of the antioxidant response element. Degradation of Nrf2 by the 26 S proteasome. J. Biol. Chem., 2003, 278(7), 4536-4541.
98. Shen, J.; Reis, J.; Morrison, D.C.; Papasian, C.; Raghavakaimal, S.; Kolbert, C.; Qureshi, A.A.; Vogel, S.N.; Qureshi, N. Key inflammatory signaling pathways are regulated by the proteasome. Shock, 2006, 25(5), 472-484.
99. Chen, D.; Daniel, K.G.; Chen, M.S.; Kuhn, D.J.; Landis-Piwowar, K.R.; Dou, Q.P. Dietary flavonoids as proteasome inhibitors and apoptosis inducers in human leukemia cells. Biochem. Pharmacol., 2005, 69(10), 1421-1432.
100. Weng, M.S.; Ho, Y.S.; Lin, J.K. Chrysin induces G1 phase cell cycle arrest in C6 glioma cells through inducing p21Waf1/Cip1 expression: involvement of p38 mitogen-activated protein kinase. Biochem. Pharmacol., 2005, 69(12), 1815-1827.
101. Nam, S.; Smith, D.M.; Dou, Q.P. Tannic acid potently inhibits tumor cell proteasome activity, increases p27 and Bax expression, and induces G1 arrest and apoptosis. Cancer Epidemiol. Biomarkers Prev., 2001, 10(10), 1083-1088.
102. Mozzicafreddo, M.; Cuccioloni, M.; Cecarini, V.; Eleuteri, A.M.; Angeletti, M. Homology modeling and docking analysis of the interaction between polyphenols and mammalian 20S proteasomes. J. Chem. Inf. Model., 2009, 49(2), 401-409.
103. Geller, D.A.; Billiar, T.R. Molecular biology of nitric oxide synthases. Cancer Metastasis. Rev., 1998, 17(1), 7-23.
104. Zamora, R.; Vodovotz, Y.; Billiar, T.R. Inducible nitric oxide synthase and inflammatory diseases. Mol. Med., 2000, 6(5), 347-373.
105. Guzik, T.J.; Korbut, R.; Adamek-Guzik, T. Nitric oxide and superoxide in inflammation and immune regulation. J. Physiol. Pharmacol., 2003, 54(4), 469-487.
106. Francisco, V.; Figueirinha, A.; Neves, B.M.; Garcia-Rodriguez, C.; Lopes, M.C.; Cruz, M.T.; Batista, M.T. Cymbopogon citratus as source of new and safe anti-inflammatory drugs: bio-guided assay using lipopolysaccharidestimulated macrophages. J. Ethnopharmacol., 2011, 133(2), 818-827.
107. Figueirinha, A.; Cruz, M.T.; Francisco, V.; Lopes, M.C.; Batista, M.T. Anti- Inflammatory Activity of Cymbopogon citratus Leaf Infusion in Lipopolysaccharide-Stimulated Dendritic Cells: Contribution of the Polyphenols. J. Med. Food, 2010, 1-10
108. Diaz, A.M.; Abad, M.J.; Fernandez, L.; Silvan, A.M.; De Santos, J.; Bermejo, P. Phenylpropanoid glycosides from Scrophularia scorodonia: in vitro anti-inflammatory activity. Life Sci., 2004, 74(20), 2515-2526.
109. Chan, M.M.; Huang, H.I.; Fenton, M.R.; Fong, D. In vivo inhibition of nitric oxide synthase gene expression by curcumin, a cancer preventive natural product with anti-inflammatory properties. Biochem. Pharmacol., 1998, 55(12), 1955-1962.
110. Kim, H.Y.; Park, E.J.; Joe, E.H.; Jou, I. Curcumin suppresses Janus kinase- STAT inflammatory signaling through activation of Src homology 2 domaincontaining tyrosine phosphatase 2 in brain microglia. J. Immunol., 2003, 171(11), 6072-6079.
111. Zhao, F.; Wang, L.; Liu, K. In vitro anti-inflammatory effects of arctigenin, a lignan from Arctium lappa L., through inhibition on iNOS pathway. J. Ethnopharmacol., 2009, 122(3), 457-462.
112. Chao, C.L.; Weng, C.S.; Chang, N.C.; Lin, J.S.; Kao, S.T.; Ho, F.M. Naringenin more effectively inhibits inducible nitric oxide synthase and cyclooxygenase-2 expression in macrophages than in microglia. Nutr. Res., 2010, 30(12), 858-864.
113. van Meeteren, M.E.; Hendriks, J.J.; Dijkstra, C.D.; van Tol, E.A. Dietary compounds prevent oxidative damage and nitric oxide production by cells involved in demyelinating disease. Biochem. Pharmacol., 2004, 67(5), 967-975.
114. Kim, H.K.; Cheon, B.S.; Kim, Y.H.; Kim, S.Y.; Kim, H.P. Effects of naturally occurring flavonoids on nitric oxide production in the macrophage cell line RAW 264.7 and their structure-activity relationships. Biochem. Pharmacol., 1999, 58(5), 759-765.
115. Shen, S.C.; Lee, W.R.; Lin, H.Y.; Huang, H.C.; Ko, C.H.; Yang, L.L.; Chen, Y.C. In vitro and in vivo inhibitory activities of rutin, wogonin, and quercetin on lipopolysaccharide-induced nitric oxide and prostaglandin E(2) production. Eur. J. Pharmacol., 2002, 446(1-3), 187-194.
116. Chen, Y.C.; Shen, S.C.; Lee, W.R.; Hou, W.C.; Yang, L.L.; Lee, T.J. Inhibition of nitric oxide synthase inhibitors and lipopolysaccharide induced inducible NOS and cyclooxygenase-2 gene expressions by rutin, quercetin, and quercetin pentaacetate in RAW 264.7 macrophages. J. Cell. Biochem., 2001, 82(4), 537-548.
117. Lee, S.J.; Lee, I.S.; Mar, W. Inhibition of inducible nitric oxide synthase and cyclooxygenase-2 activity by 1,2,3,4,6-penta-O-galloyl-beta-D- glucose in murine macrophage cells. Arch. Pharm. Res., 2003, 26(10), 832-839.
118. Kwak, W.J.; Moon, T.C.; Lin, C.X.; Rhyn, H.G.; Jung, H.; Lee, E.; Kwon, D.Y.; Son, K.H.; Kim, H.P.; Kang, S.S.; Murakami, M.; Kudo, I.; Chang, H.W. Papyriflavonol A from Broussonetia papyrifera inhibits the passive cutaneous anaphylaxis reaction and has a secretory phospholipase A2- inhibitory activity. Biol. Pharm. Bull., 2003, 26(3), 299-302.
119. Dreiseitel, A.; Korte, G.; Schreier, P.; Oehme, A.; Locher, S.; Hajak, G.; Sand, P.G. sPhospholipase A(2) is inhibited by anthocyanidins. J. Neural Transm., 2009, 116(9), 1071-1077.
120. Hsu, M.F.; Lu, M.C.; Tsao, L.T.; Kuan, Y.H.; Chen, C.C.; Wang, J.P. Mechanisms of the influence of magnolol on eicosanoid metabolism in neutrophils. Biochem. Pharmacol., 2004, 67(5), 831-840.
121. de la Puerta, R.; Ruiz Gutierrez, V.; Hoult, J.R. Inhibition of leukocyte 5- lipoxygenase by phenolics from virgin olive oil. Biochem. Pharmacol., 1999, 57(4), 445-449.
122. Yoshimoto, T.; Furukawa, M.; Yamamoto, S.; Horie, T.; Watanabe-Kohno, S. Flavonoids: potent inhibitors of arachidonate 5-lipoxygenase. Biochem. Biophys. Res. Commun., 1983, 116(2), 612-618.
123. Chi, Y.S.; Jong, H.G.; Son, K.H.; Chang, H.W.; Kang, S.S.; Kim, H.P. Effects of naturally occurring prenylated flavonoids on enzymes metabolizing arachidonic acid: cyclooxygenases and lipoxygenases. Biochem. Pharmacol., 2001, 62(9), 1185-1191.
124. Silvan, A.M.; Abad, M.J.; Bermejo, P.; Sollhuber, M.; Villar, A. Antiinflammatory activity of coumarins from Santolina oblongifolia. J. Nat. Prod., 1996, 59(12), 1183-1185.
125. Hoult, J.R.; Paya, M. Pharmacological and biochemical actions of simple coumarins: natural products with therapeutic potential. Gen. Pharmacol., 1996, 27(4), 713-722.
126. Resch, M.; Steigel, A.; Chen, Z.L.; Bauer, R. 5-Lipoxygenase and cyclooxygenase-1 inhibitory active compounds from Atractylodes lancea. J. Nat. Prod., 1998, 61(3), 347-350.
127. Petroni, A.; Blasevich, M.; Papini, N.; Salami, M.; Sala, A.; Galli, C. Inhibition of leukocyte leukotriene B4 production by an olive oil-derived phenol identified by mass-spectrometry. Thromb. Res., 1997, 87(3), 315-322.
128. Son, J.K.; Son, M.J.; Lee, E.; Moon, T.C.; Son, K.H.; Kim, C.H.; Kim, H.P.; Kang, S.S.; Chang, H.W. Ginkgetin, a Biflavone from Ginko biloba leaves, inhibits cyclooxygenases-2 and 5-lipoxygenase in mouse bone marrowderived mast cells. Biol. Pharm. Bull., 2005, 28(12), 2181-2184.
129. Morikawa, K.; Nonaka, M.; Narahara, M.; Torii, I.; Kawaguchi, K.; Yoshikawa, T.; Kumazawa, Y.; Morikawa, S. Inhibitory effect of quercetin on carrageenan-induced inflammation in rats. Life Sci., 2003, 74(6), 709-721.
130. Kim, H.J.; Jang, S.I.; Kim, Y.J.; Chung, H.T.; Yun, Y.G.; Kang, T.H.; Jeong, O.S.; Kim, Y.C. Scopoletin suppresses pro-inflammatory cytokines and PGE2 from LPS-stimulated cell line, RAW 264.7 cells. Fitoterapia, 2004, 75(3-4), 261-266.
131. Seeram, N.P.; Zhang, Y.; Nair, M.G. Inhibition of proliferation of human cancer cells and cyclooxygenase enzymes by anthocyanidins and catechins. Nutr. Cancer, 2003, 46(1), 101-106.
132. Miles, E.A.; Zoubouli, P.; Calder, P.C. Differential anti-inflammatory effects of phenolic compounds from extra virgin olive oil identified in human whole blood cultures. Nutrition, 2005, 21(3), 389-394.
133. Gerritsen, M.E.; Carley, W.W.; Ranges, G.E.; Shen, C.P.; Phan, S.A.; Ligon, G.F.; Perry, C.A. Flavonoids inhibit cytokine-induced endothelial cell adhesion protein gene expression. Am. J. Pathol., 1995, 147(2), 278-292.
134. Youdim, K.A.; McDonald, J.; Kalt, W.; Joseph, J.A. Potential role of dietary flavonoids in reducing microvascular endothelium vulnerability to oxidative and inflammatory insults (small star, filled). J. Nutr. Biochem., 2002, 13(5), 282-288.
135. Ueda, H.; Yamazaki, C.; Yamazaki, M. A hydroxyl group of flavonoids affects oral anti-inflammatory activity and inhibition of systemic tumor necrosis factor-alpha production. Biosci. Biotechnol. Biochem., 2004, 68(1), 119-125.
136. Lee, K.M.; Lee, K.W.; Byun, S.; Jung, S.K.; Seo, S.K.; Heo, Y.S.; Bode, A.M.; Lee, H.J.; Dong, Z. 5-deoxykaempferol plays a potential therapeutic role by targeting multiple signaling pathways in skin cancer. Cancer Prev. Res. (Phila.), 2010, 3(4), 454-465.
137. Gonzalez, R.; Ballester, I.; Lopez-Posadas, R.; Suarez, M.D.; Zarzuelo, A.; Martinez-Augustin, O.; Sanchez de Medina, F. Effects of flavonoids and other polyphenols on inflammation. Crit. Rev. Food Sci. Nutr., 2011, 51(4), 331-362.
138. Pelzer, L.E.; Guardia, T.; Osvaldo Juarez, A.; Guerreiro, E. Acute and chronic antiinflammatory effects of plant flavonoids. Farmaco, 1998, 53(6), 421-424.
139. Huang, M.T.; Lysz, T.; Ferraro, T.; Abidi, T.F.; Laskin, J.D.; Conney, A.H. Inhibitory effects of curcumin on in vitro lipoxygenase and cyclooxygenase activities in mouse epidermis. Cancer Res., 1991, 51(3), 813-819.
140. Kowluru, R.A.; Kanwar, M. Effects of curcumin on retinal oxidative stress and inflammation in diabetes. Nutr. Metab. (Lond.), 2007, 4, 8.
141. Sebai, H.; Ben-Attia, M.; Sani, M.; Aouani, E.; Ghanem-Boughanmi, N. Protective effect of resveratrol in endotoxemia-induced acute phase response in rats. Arch. Toxicol., 2009, 83(4), 335-340.
142. Martin, A.R.; Villegas, I.; La Casa, C.; de la Lastra, C.A. Resveratrol, a polyphenol found in grapes, suppresses oxidative damage and stimulates apoptosis during early colonic inflammation in rats. Biochem. Pharmacol., 2004, 67(7), 1399-1410.
143. Do, G.M.; Kwon, E.Y.; Kim, H.J.; Jeon, S.M.; Ha, T.Y.; Park, T.; Choi, M.S. Long-term effects of resveratrol supplementation on suppression of atherogenic lesion formation and cholesterol synthesis in apo E-deficient mice. Biochem. Biophys. Res. Commun., 2008, 374(1), 55-59.
144. Yano, S.; Umeda, D.; Yamashita, T.; Ninomiya, Y.; Sumida, M.; Fujimura, Y.; Yamada, K.; Tachibana, H. Dietary flavones suppresses IgE and Th2 cytokines in OVA-immunized BALB/c mice. Eur. J. Nutr., 2007, 46(5), 257-263.
145. Kotanidou, A.; Xagorari, A.; Bagli, E.; Kitsanta, P.; Fotsis, T.; Papapetropoulos, A.; Roussos, C. Luteolin reduces lipopolysaccharideinduced lethal toxicity and expression of proinflammatory molecules in mice. Am. J. Respir. Crit. Care Med., 2002, 165(6), 818-823.
146. Park, B.K.; Heo, M.Y.; Park, H.; Kim, H.P. Inhibition of TPA-induced cyclooxygenase-2 expression and skin inflammation in mice by wogonin, a plant flavone from Scutellaria radix. Eur. J. Pharmacol., 2001, 425(2), 153-157.
147. Verdrengh, M.; Jonsson, I.M.; Holmdahl, R.; Tarkowski, A. Genistein as an anti-inflammatory agent. Inflamm. Res., 2003, 52(8), 341-346.
148. Takahashi, K.; Morikawa, A.; Kato, Y.; Sugiyama, T.; Koide, N.; Mu, M.M.; Yoshida, T.; Yokochi, T. Flavonoids protect mice from two types of lethal shock induced by endotoxin. FEMS Immunol. Med. Microbiol., 2001, 31(1), 29-33.
149. Mamani-Matsuda, M.; Kauss, T.; Al-Kharrat, A.; Rambert, J.; Fawaz, F.; Thiolat, D.; Moynet, D.; Coves, S.; Malvy, D.; Mossalayi, M.D. Therapeutic and preventive properties of quercetin in experimental arthritis correlate with decreased macrophage inflammatory mediators. Biochem. Pharmacol., 2006, 72(10), 1304-1310.
150. Rogerio, A.P.; Kanashiro, A.; Fontanari, C.; da Silva, E.V.; Lucisano-Valim, Y.M.; Soares, E.G.; Faccioli, L.H. Anti-inflammatory activity of quercetin and isoquercitrin in experimental murine allergic asthma. Inflamm. Res., 2007, 56(10), 402-408.
151. Galvez, J.; Coelho, G.; Crespo, M.E.; Cruz, T.; Rodriguez-Cabezas, M.E.; Concha, A.; Gonzalez, M.; Zarzuelo, A. Intestinal anti-inflammatory activity of morin on chronic experimental colitis in the rat. Aliment. Pharmacol. Ther., 2001, 15(12), 2027-2039.
152. Wei, H.; Frenkel, K. Relationship of oxidative events and DNA oxidation in SENCAR mice to in vivo promoting activity of phorbol ester-type tumor promoters. Carcinogenesis, 1993, 14(6), 1195-1201.
153. Morinobu, A.; Biao, W.; Tanaka, S.; Horiuchi, M.; Jun, L.; Tsuji, G.; Sakai, Y.; Kurosaka, M.; Kumagai, S. (-)-Epigallocatechin-3-gallate suppresses osteoclast differentiation and ameliorates experimental arthritis in mice. Arthritis Rheum., 2008, 58(7), 2012-2018.
154. Abboud, P.A.; Hake, P.W.; Burroughs, T.J.; Odoms, K.; O'Connor, M.; Mangeshkar, P.; Wong, H.R.; Zingarelli, B. Therapeutic effect of epigallocatechin-3-gallate in a mouse model of colitis. Eur. J. Pharmacol., 2008, 579(1-3), 411-417.
155. Tjendraputra, E.; Tran, V.H.; Liu-Brennan, D.; Roufogalis, B.D.; Duke, C.C. Effect of ginger constituents and synthetic analogs on cyclooxygenase-2 enzyme in intact cells. Bioorg. Chem., 2001, 29(3), 156-163.
156. Patwardhan, R.S.; Checker, R.; Sharma, D.; Kohli, V.; Priyadarsini, K.I.; Sandur, S.K. Dimethoxycurcumin, a metabolically stable analog of curcumin, exhibits anti-inflammatory activities in murine and human lymphocytes. Biochem. Pharmacol., 2011, 82(6), 642-657.
157. Olivera, A.; Moore, T.W.; Hu, F.; Brown, A.P.; Sun, A.; Liotta, D.C.; Snyder, J.P.; Yoon, Y.; Shim, H.; Marcus, A.I.; Miller, A.H.; Pace, T.W. Inhibition of the NF-kappaB signaling pathway by the curcumin analog, 3,5- Bis(2-pyridinylmethylidene)-4-piperidone (EF31): anti-inflammatory and anti-cancer properties. Int. Immunopharmacol., 2012, 12(2), 368-377.
158. Wang, Y.; Yu, C.; Pan, Y.; Yang, X.; Huang, Y.; Feng, Z.; Li, X.; Yang, S.; Liang, G. A Novel Synthetic Mono-Carbonyl Analog of Curcumin, A13, Exhibits Anti-Inflammatory Effects In vivo by Inhibition of Inflammatory Mediators. Inflammation, 2011.
159. Kim, Y.H.; Kim, J.; Park, H.; Kim, H.P. Anti-inflammatory activity of the synthetic chalcone derivatives: inhibition of inducible nitric oxide synthasecatalyzed nitric oxide production from lipopolysaccharide-treated RAW 264.7 cells. Biol. Pharm. Bull., 2007, 30(8), 1450-1455.
160. Vogel, S.; Barbic, M.; Jurgenliemk, G.; Heilmann, J. Synthesis, cytotoxicity, anti-oxidative and anti-inflammatory activity of chalcones and influence of A-ring modifications on the pharmacological effect. Eur. J. Med. Chem., 2010, 45(6), 2206-2213.
161. Kim, S.J.; Park, H.; Kim, H.P. Inhibition of nitric oxide production from lipopolysaccharide-treated RAW 264.7 cells by synthetic flavones: structureactivity relationship and action mechanism. Arch. Pharm. Res., 2004, 27(9), 937-943.
162. Lim, H.; Jin, J.H.; Park, H.; Kim, H.P. New synthetic anti-inflammatory chrysin analog, 5,7-dihydroxy-8-(pyridine-4yl)flavone. Eur. J. Pharmacol., 2011, 670(2-3), 617-622.
163. Ortega, M.G.; Saragusti, A.C.; Cabrera, J.L.; Chiabrando, G.A. Quercetin tetraacetyl derivative inhibits LPS-induced nitric oxide synthase (iNOS) expression in J774A.1 cells. Arch. Biochem. Biophys., 2010, 498(2), 105-110.
164. Iijima, T.; Mohri, Y.; Hattori, Y.; Kashima, A.; Kamo, T.; Hirota, M.; Kiyota, H.; Makabe, H. Synthesis of (-)-epicatechin 3-(3-O-methylgallate) and (+)-catechin 3-(3-O-methylgallate), and their anti-inflammatory activity. Chem. Biodivers., 2009, 6(4), 520-526.
165. Bonfili, L.; Cecarini, V.; Amici, M.; Cuccioloni, M.; Angeletti, M.; Keller, J.N.; Eleuteri, A.M. Natural polyphenols as proteasome modulators and their role as anti-cancer compounds. FEBS J., 2008, 275(22), 5512-5526.
166. Kim, H.P.; Son, K.H.; Chang, H.W.; Kang, S.S. Anti-inflammatory plant flavonoids and cellular action mechanisms. J. Pharmacol. Sci., 2004, 96(3), 229-245.
167. Benavente-Garcia, O.; Castillo, J. Update on uses and properties of citrus flavonoids: new findings in anticancer, cardiovascular, and antiinflammatory activity. J. Agric. Food Chem., 2008, 56(15), 6185-6205.
168. Shie, J.J.; Chen, C.A.; Lin, C.C.; Ku, A.F.; Cheng, T.J.; Fang, J.M.; Wong, C.H. Regioselective synthesis of di-C-glycosylflavones possessing antiinflammation activities. Org. Biomol. Chem., 2010, 8(19), 4451-4462.
169. Wan, S.B.; Landis-Piwowar, K.R.; Kuhn, D.J.; Chen, D.; Dou, Q.P.; Chan, T.H. Structure-activity study of epi-gallocatechin gallate (EGCG) analogs as proteasome inhibitors. Bioorg. Med. Chem., 2005, 13(6), 2177-2185.