Effect of 5-O-methylhirsutanonol on nuclear factor-κB-dependent production of NO and expression of iNOS in lipopolysaccharide-induced RAW264.7 cells

Journal of Agricultural and Food Chemistry

Volumn 56, Issue 1, 2008, Pages 92-98

  Han, Jong Min ^a   Woo, Song Lee ^a   Kim, Ju Ryoung ^a   Son, Joonsok ^a   Kwon, Oh Hyung ^a   Lee, Hyun Jun ^a   Jung, Joon Lee ^a   Jeong, Tae Sook ^a  

^a Korea Research Institute of Bioscience and Biotechnology (KRIBB)   (South Korea)

Author keywords

5 O methylhirsutanonol (5 MH); Diarylheptanoids; Inducible nitric oxide synthease (iNOS); Nitric oxide (NO); Nuclear factor B (NF B); Reactive oxygen species (ROS)

Indexed keywords

5 O METHYLHIRSUTANONOL; 5-O-METHYLHIRSUTANONOL; ANTIINFLAMMATORY AGENT; HEPTANE DERIVATIVE; IMMUNOGLOBULIN ENHANCER BINDING PROTEIN; INDUCIBLE NITRIC OXIDE SYNTHASE; LIPOPOLYSACCHARIDE; MESSENGER RNA; NITRIC OXIDE; UNCLASSIFIED DRUG;

ANIMAL; ARTICLE; BIOSYNTHESIS; CELL LINE; DRUG EFFECT; GENE EXPRESSION; GENETICS; MACROPHAGE; METABOLISM; MOUSE;

ANIMALS; ANTI-INFLAMMATORY AGENTS; CELL LINE; DIARYLHEPTANOIDS; GENE EXPRESSION; LIPOPOLYSACCHARIDES; MACROPHAGES; MICE; NF-KAPPA B; NITRIC OXIDE; NITRIC OXIDE SYNTHASE TYPE II; RNA, MESSENGER;

ALNUS; ALNUS JAPONICA;

EID: 38549174558     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf0721085     Document Type: Article

References (43)

1. Bowie, A.; O'Neill, L. A. Oxidative stress and nuclear factor-κB activation: A reassessment of the evidence in the light of recent discoveries. Biochem. Pharmacol. 2000, 59, 13-23.
2. Zingarelli, B.; Hake, P. W.; Yang, Z.; O'Connor, M.; Denenberg, A.; Wong, H. R. Absence of inducible nitric oxide synthase modulates early reperfusion-induced NF-κB and AP-1 activation and enhances myocardial damage. FASEB. J. 2002, 16, 327-342.
3. Moncada, S.; Palmer, R. M.; Higgs, E. A. Nitric oxide: Physiology, pathophysiology, and pharmacology. Pharmacol. Rev. 1991, 43, 109-142.
4. MacMicking, J.; Xie, Q. W.; Nathan, C. Nitric oxide and macrophage function. Annu. Rev. Immunol. 1997, 15, 323-350.
5. Liu, R. H.; Hotchkiss, J. H. Potential genotoxicity of chronically elevated nitric oxide: A review. Mutat. Res. 1995, 339, 73-89.
6. Ghosh, S.; May, M. J.; Kopp, E. B. NF-κB and Rel proteins: Evolutionarily conserved mediators of immune responses. Annu. Rev. Immunol. 1998, 16, 225-260.
7. Bours, V.; Bonizzi, G.; Bentires-Alj, M.; Bureau, F.; Piette, J.; Lekeux, P.; Merville, M. NF-κB activation in response to toxical and therapeutical agents: Role in inflammation and cancer treatment. Toxicology 2000, 153, 27-38.
8. Wang, T.; Zhang, X.; Li, J. J. The role of NF-κB in the regulation of cell stress responses. Int. Immunopharmacol. 2002, 2, 1509-1520.
9. Hayakawa, M.; Miyashita, H.; Sakamoto, I.; Kitagawa, M.; Tanaka, H.; Yasuda, H.; Karin, M.; Kikugawa, K. Evidence that reactive oxygen species do not mediate NF-κB activation. EMBO J. 2003, 22, 3356-3366.
10. Olszanecki, R.; Jawien, J.; Gajda, M.; Mateuszuk, L.; Gebska, A.; Korabiowska, M.; Chlopicki, S.; Korbut, R. Effect of curcumin on atherosclerosis in apoE/LDLR-double knockout mice. J. Physiol. Pharmacol. 2005, 56, 627-635.
11. Jawien, J.; Gajda, M.; Mateuszuk, L.; Olszanecki, R.; Jakubowski, A.; Szlachcic, A.; Korabiowska, M.; Korbut, R. Inhibition of nuclear factor-κB attenuates artherosclerosis in apoE/LDLR - Double knockout mice. J. Physiol. Pharmacol. 2005, 56, 483-489.
12. Lee, M. W.; Kim, J. H.; Jeong, D. W.; Ahn, K. H.; Toh, S. H.; Surh, Y. J. Inhibition of cyclooxygenase-2 expression by diarylheptanoids from the bark of Alnus hirsuta var. sibirica. Biol. Pharm. Bull. 2000, 23, 517-518.
13. Kim, J. H.; Lee, K. W.; Lee, M. W.; Lee, H. J.; Kim, S. H.; Surh, Y. J. Hirsutenone inhibits phorbol ester-induced upregulation of COX-2 and MMP-9 in cultured human mammary epithelial cells: NF-κB as a potential molecular target. FEBS Lett. 2006, 580, 385-392.
14. Lee, M. W.; Kim, N. Y.; Park, M. S.; Ahn, K. H.; Toh, S. H.; Hahn, D. R.; Kim, Y. C.; Chung, H. T. Diarylheptanoids with in vitro inducible nitric oxide synthesis inhibitory activity from Alnus hirsuta. Planta Med. 2000, 66, 551-553.
15. Lee, C. J.; Lee, S. S.; Chen, S. C.; Ho, F. M.; Lin, W. W. Oregonin inhibits lipopolysaccharide-induced iNOS gene transcription and upregulates HO-1 expression in macrophages and microglia. Br. J. Pharmacol. 2005, 146, 378-388.
16. Kuroyanagi, M.; Shimomae, M.; Nagashima, Y.; Muto, N.; Okuda, T.; Kawahara, N.; Nakane, T.; Sano, T. New diarylheptanoids from Alnus japonica and their antioxidative activity. Chem. Pharm. Bull. 2005, 53, 1519-1523.
17. Lee, W. S.; Kim, J. R.; Im, K. R.; Cho, K. H.; Sok, D. E.; Jeong, T. S. Antioxidant effects of diarylheptanoid derivatives from Alnus japonica on human LDL oxidation. Planta Med. 2005, 71, 295-299.
18. Kim, J. R. Isolation and characterization of antiatherosclerotic substances from Alnus japonica and Torreya nucifera. Ph.D. Thesis, Chungnam National University, Korea, 2005.
19. Lee, S. J. Korea Folk Medicine; Seoul National University Publishing Center Press: Seoul, Korea, 1996; p 40.
20. Yagi, K. Lipid Peroxides in Biology and Medicine; Yagi, K., Ed.; Academic Press: Orlando, FL, 1982; p 223.
21. Lesnik, P.; Dachet, C.; Petit, L.; Moreau, M.; Griglio, S.; Brudi, P.; Chapman, M. J. Impact of a combination of a calcium antagonist and a β-blocker on cell- and copper-mediated oxidation of LDL and on the accumulation and efflux of cholesterol in human macrophages and murine J774 cells. Arterioscler., Thromb., Vasc. Biol. 1997, 17, 979-988.
22. Kim, Y. M.; de Vera, M. E.; Watkins, S. C.; Billiar, T. R. Nitric oxide protects cultured rat hepatocytes from tumor necrosis factor-α-induced apoptosis by inducing heat shock protein 70 expression. J. Biol. Chem. 1997, 272, 1402-1411.
23. Lee, W. S.; Kim, J. R.; Han, J. M.; Jang, K. C.; Sok, D. E.; Jeong, T. S. Antioxidant activities of abietane diterpenoids isolated from Torreya nucifera leaves. J. Agric. Food Chem. 2006, 54, 5369-5374.
24. Lee, J. H.; Koo, T. H.; Hwang, B. Y.; Lee, J. J. Kaurane diterpene, kamebakaurin, inhibits NF-κB by directly targeting the DNA-binding activity of p50 and blocks the expression of antiapoptotic NF-κB target genes. J. Biol. Chem. 2002, 277, 18411-18420.
25. Xu, M. Z.; Lee, W. S.; Han, J. M.; Oh, H. W.; Park, D. S.; Tian, G. R.; Jeong, T. S.; Park, H. Y. Antioxidant and anti-inflammatory activities of N-acetyldopamine dimers from Periostracum Cicadae. Bioorg. Med. Chem. 2006, 14, 7826-7834.
26. Lee, H. J.; Masuda, E. S.; Arai, N.; Arai, K.; Yokota, T. Definition of cis-regulatory elements of the mouse interleukin-5 gene promoter. Involvement of nuclear factor of activated T cell-related factors in interleukin-5 expression. J. Biol. Chem. 1995, 270, 17541-17550.
27. Heinecke, J. W.; Rosen, H.; Chait, A. Iron and copper promote modification of low density lipoprotein by human arterial smooth muscle cells in culture. J. Clin. Invest. 1984, 74, 1890-1894.
28. Schreck, R.; Meier, B.; Mannel, D. N.; Droge, W.; Baeuerle, P. A. Dithiocarbamates as potent inhibitors of nuclear factor κB activation in intact cells. J. Exp. Med. 1992, 175, 1181-1194.
29. Jin, W.; Cai, X. F.; Na, M.; Lee, J. J.; Bae, K. Diarylheptanoids from Alnus hirsuta inhibit the NF-κB activation and NO and TNF-α production. Biol. Pharm. Bull. 2007, 30, 810-813.
30. Ross, R. The pathogenesis of atherosclerosis: A perspective for the 1990s. Nature 1993, 362, 801-809.
31. Brand, K.; Page, S.; Rogler, G.; Bartsch, A.; Brandl, R.; Knuechel, R.; Page, M.; Kaltschmidt, C.; Baeuerle, P. A.; Neumeier, D. Activated transcription factor nuclear factor-κB is present in the atherosclerotic lesion. J. Clin. Invest. 1996, 97, 1715-1722.
32. Brand, K.; Page, S.; Walli, A. K.; Neumeier, D.; Baeuerle, P. A. Role of nuclear factor-κB in atherogenesis. Exp. Physiol. 1997, 82, 297-304.
33. Monaco, C.; Andreakos, E.; Kiriakidis, S.; Mauri, C.; Bicknell, C.; Foxwell, B.; Cheshire, N.; Paleolog, E.; Feldmann, M. Canonical pathway of nuclear factor κB activation selectively regulates proinflammatory and prothrombotic responses in human atherosclerosis. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 5634-5639.
34. Yoshimura, S.; Morishita, R.; Hayashi, K.; Yamamoto, K.; Nakagami, H.; Kaneda, Y.; Sakai, N.; Ogihara, T. Inhibition of intimal hyperplasia after balloon injury in rat carotid artery model using cis-element "decoy" of nuclear factor-κB binding site as a novel molecular strategy. Gene Ther. 2001, 8, 1635-1642.
35. Monaco, C.; Paleolog, E. Nuclear factor κB: A potential therapeutic target in atherosclerosis and thrombosis. Cardiovasc. Res. 2004, 61, 671-682.
36. 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, 1955-1962.
37. Pan, M. H.; Lin-Shiau, S. Y.; Lin, J. K. Comparative studies on the suppression of nitric oxide synthase by curcumin and its hydrogenated metabolites through down-regulation of IκB kinase and NFκB activation in macrophages. Biochem. Pharmacol. 2000, 60, 1665-1676.
38. Baeuerle, P. A.; Henkel, T. Function and activation of NF-κB in the immune system. Annu. Rev. Immunol. 1994, 12, 141-179.
39. Han, J. M.; Lee, W. S.; Kim, J. R.; Son, J.; Nam, K. H.; Choi, S. C.; Lim, J. S.; Jeong, T. S. Effects of diarylheptanoids on the tumor necrosis factor-α-induced expression of adhesion molecules in human umbilical vein endothelial cells. J. Agri. Food Chem. 2007, 55, 9457-9464.
40. Witztum, J. L. Role of oxidised low density lipoprotein in atherogenesis. Br. Heart. J. 1993, 69 (Suppl. 1), S12-S8.
41. Rahman, I.; Marwick, J.; Kirkham, P. Redox modulation of chromatin remodeling: Impact on histone acetylation and deacetylation, NF-κB and pro-inflammatory gene expression. Biochem. Pharmacol. 2004, 68, 1255-1267.
42. Borek, C. Antioxidant health effects of aged garlic extract. J. Nutr. 2001, 131, 1010S-1015S.
43. Park, J. Y.; Cho, H. Y.; Kim, J. K.; Noh, K. H.; Yang, J. R.; Ahn, J. M.; Lee, M. O.; Song, Y. S. Chlorella dichloromethane extract ameliorates NO production and iNOS expression through the down-regulation of NF κB activity mediated by suppressed oxidative stress in RAW264.7 macrophages. Clin. Chim. Acta 2005, 351, 185-196.