Differential effects of resveratrol and its natural analogs, piceatannol and 3,5,4′-trans-trimethoxystilbene, on anti-inflammatory heme oxigenase-1 expression in RAW264.7 macrophages

BioFactors

Volumn 40, Issue 1, 2014, Pages 138-145

  Son, Yong ^a   Chung, Hun Taeg ^b   Pae, Hyun Ock ^a  

^a Wonkwang University School of Medicine   (South Korea)

^b University of Ulsan   (South Korea)

Author keywords

3,5,4 trans trimethoxystilbene; Heme oxygenase 1; Interleukin 1 ; Macrophages; Piceatannol; Resveratrol; Tumor necrosis factor

Indexed keywords

3,5,4′-TRANS-TRIMETHOXYSTILBENE; HEME OXYGENASE-1; INTERLEUKIN-1Β; MACROPHAGES; PICEATANNOL; RESVERATROL; TUMOR NECROSIS FACTOR-Α;

ANIMALS; ANTI-INFLAMMATORY AGENTS; CELL LINE; CELL SURVIVAL; ENZYME INDUCTION; GENE EXPRESSION; HEME OXYGENASE-1; INTERLEUKIN-1BETA; LIPOPOLYSACCHARIDES; MACROPHAGES; MEMBRANE PROTEINS; MICE; STILBENES; TUMOR NECROSIS FACTOR-ALPHA;

EID: 84894069941     PISSN: 09516433     EISSN: 18728081     Source Type: Journal    
DOI: 10.1002/biof.1108     Document Type: Article

References (35)

1. de la Lastra, C. A. and Villegas, I. (2005) Resveratrol as an anti-inflammatory and anti-aging agent: mechanisms and clinical implications. Mol. Nutr. Food Res. 49, 405-430.
2. Walle, T., Hsieh, F., DeLegge, M. H., Oatis, J. E. Jr, and Walle, U. K. (2004) High absorption but very low bioavailability of oral resveratrol in humans. Drug Metab. Dispos. 32, 1377-1382.
3. Wenzel, E. and Somoza, V. (2005) Metabolism and bioavailability of trans-resveratrol. Mol. Nutr. Food Res. 49, 472-481.
4. Potter, G. A., Patterson, L. H., Wanogho, E., Perry, P. J., Butler, P. C., et al. (2002) The cancer preventative agent resveratrol is converted to the anticancer agent piceatannol by the cytochrome P450 enzyme CYP1B1. Br. J. Cancer 86, 774-778.
5. Blair G. E., Cassady J. M., Robbers J. E., Tyler V. E., and Raffauf R. F. (1969) Isolation of 3, 4′, 5-trimethoxy-trans-stilbene, otobaene and hydroxyotobain from Virola cuspidata. Phytochemistry 8, 497-500.
6. Lin, H. S. and Ho, P.C. (2009) A rapid HPLC method for the quantification of 3, 5, 4'-trimethoxy-trans-stilbene (TMS) in rat plasma and its application in pharmacokinetic study. J. Pharm. Biomed. Anal. 49, 387-392.
7. Piotrowska, H., Kucinska, M., and Murias, M. (2012) Biological activity of piceatannol: leaving the shadow of resveratrol. Mutat. Res. 750, 60-82.
8. Deng, Y. H., Alex, D., Huang, H. Q., Wang, N., Yu, N., et al. (2011) Inhibition of TNF-α-mediated endothelial cell-monocyte cell adhesion and adhesion molecules expression by the resveratrol derivative, trans-3, 5, 4'-trimethoxystilbene. Phytother. Res. 25, 451-457.
9. Fujiwara, N. and Kobayashi, K. (2005) Macrophages in inflammation. Curr. Drug Targets Inflamm. Allergy 4, 281-286.
10. Dinarello, C. A. (1977) Role of pro- and anti-inflammatory cytokines during inflammation: experimental and clinical findings. J. Biol. Regul. Homeost. Agents 11, 91-103.
11. Lawrence, T. and Gilroy, D. W. (2007) Chronic inflammation: a failure of resolution? Int. J. Exp. Pathol. 88, 85-94.
12. Dong, Z., Lavrovsky, Y., Venkatachalam, M. A., and Roy, A. K. (2000) Heme oxygenase-1 in tissue pathology: the Yin and Yang. Am. J. Pathol. 156, 1485-1488.
13. Pae, H. O., Son, Y., Kim, N. H., Jeong, H. J., Chang, K.C., et al. (2010) Role of heme oxygenase in preserving vascular bioactive NO. Nitric Oxide 23, 251-257.
14. Pae, H. O., Lee, Y. C., and Chung, H. T. (2008) Heme oxygenase-1 and carbon monoxide: emerging therapeutic targets in inflammation and allergy. Recent Pat. Inflamm. Allergy Drug Discov. 2, 159-165.
15. Kil, J. S., Son, Y., Cheong, Y. K., Kim, N. H., Jeong, H. J., et al. (2012) Okanin, a chalcone found in the genus Bidens, and 3-penten-2-one inhibit inducible nitric oxide synthase expression via heme oxygenase-1 induction in RAW264.7 macrophages activated with lipopolysaccharide. J. Clin. Biochem. Nutr. 50, 53-58.
16. Pae, H. O., Jeong, S. O., Koo, B. S., Ha, H. Y., Lee, K. M., et al (2008) Tranilast, an orally active anti-allergic drug, up-regulates the anti-inflammatory heme oxygenase-1 expression but down-regulates the pro-inflammatory cyclooxygenase-2 and inducible nitric oxide synthase expression in RAW264.7 macrophages. Biochem. Biophys. Res. Commun. 371, 361-365.
17. Kim, K. M., Pae, H. O., Zhung, M., Ha, H. Y., Ha, Y. A., et al. (2008) Involvement of anti-inflammatory heme oxygenase-1 in the inhibitory effect of curcumin on the expression of pro-inflammatory inducible nitric oxide synthase in RAW264.7 macrophages. Biomed. Pharmacother. 62, 630-636.
18. Pae, H. O., Jeong, G. S., Kim, H. S., Woo, W. H., Rhew, H. Y., et al. (2007) Costunolide inhibits production of tumor necrosis factor-alpha and interleukin-6 by inducing heme oxygenase-1 in RAW264.7 macrophages. Inflamm. Res. 56, 520-526.
19. Seo, W. Y., Goh, A. R., Ju, S. M., Song, H. Y., Kwon, D. J., et al. (2011) Celastrol induces expression of heme oxygenase-1 through ROS/Nrf2/ARE signaling in the HaCaT cells. Biochem. Biophys. Res. Commun. 407, 535-540.
20. Jin, C. H., Lee, H. J., Park, Y. D., Choi, D. S., Kim, D. S., et al. (2010) Isoegomaketone inhibits lipopolysaccharide-induced nitric oxide production in RAW 264.7 macrophages through the heme oxygenase-1 induction and inhibition of the interferon-beta-STAT-1 pathway. J. Agric. Food Chem. 58, 860-867.
21. Leung, P. O., Wang, S. H., Lu, S. H., Chou, W. H., Shiau, C. Y., et al. (2011) Simvastatin inhibits pro-inflammatory mediators through induction of heme oxygenase-1 expression in lipopolysaccharide-stimulated RAW264.7 macrophages. Toxicol. Lett. 207, 159-166.
22. Park, S. Y., Lee, S. W., Baek, S. H., Lee, S. J., Lee, W. S., et al. (2011) Induction of heme oxygenase-1 expression by cilostazol contributes to its anti-inflammatory effects in J774 murine macrophages. Immunol. Lett. 136, 138-145.
23. Walle, T. (2011) Bioavailability of resveratrol. Ann. NY Acad. Sci. 1215, 9-15.
24. Delmas, D., Aires, V., Limagne, E., Dutartre, P., Mazué, F., et al. (2011) Transport, stability, and biological activity of resveratrol. Ann. NY Acad. Sci. 1215, 48-59.
25. Ndiaye, M., Kumar, R., and Ahmad, N. (2011) Resveratrol in cancer management: where are we and where we go from here? Ann. NY Acad. Sci. 1215, 144-149.
26. Murias, M., Handler, N., Erker, T., Pleban, K., Ecker, G., et al. (2004) Resveratrol analogues as selective cyclooxygenase-2 inhibitors: synthesis and structure-activity relationship. Bioorg. Med. Chem. 12, 5571-5578.
27. Paine, A., Eiz-Vesper, B., Blasczyk, R., and Immenschuh, S. (2010) Signaling to heme oxygenase-1 and its anti-inflammatory therapeutic potential. Biochem. Pharmacol. 80, 1895-1903.
28. Liu, D., Kim, D. H., Park, J. M., Na, H. K., and Surh, Y. J. (2009) Piceatannol inhibits phorbol ester-induced NF-κB activation and COX-2 expression in cultured human mammary epithelial cells. Nutr. Cancer 61, 855-863.
29. Kang, O. H., Jang, H. J., Chae, H. S., Oh, Y. C., Choi, J. G., et al. (2009) Anti-inflammatory mechanisms of resveratrol in activated HMC-1 cells: pivotal roles of NF-κB and MAPK. Pharmacol. Res. 59, 330-337.
30. Busch, F., Mobasheri, A., Shayan, P., Stahlmann, R., and Shakibaei, M. (2012) Sirt-1 is required for the inhibition of apoptosis and inflammatory responses in human tenocytes. J. Biol. Chem. 287, 25770-25781.
31. 2S) in inflammation. Arch. Pharm. Res. 32, 1155-1162.
32. Tsoyi, K., Lee, T. Y., Lee, Y. S., Kim, H. J., Seo, H. G., et al. (2009) Heme-oxygenase-1 induction and carbon monoxide-releasing molecule inhibit lipopolysaccharide (LPS)-induced high-mobility group box 1 release in vitro and improve survival of mice in LPS- and cecal ligation and puncture-induced sepsis model in vivo. Mol. Pharmacol. 76, 173-182.
33. Kadl, A., Pontiller, J., Exner, M., and Leitinger, N. (2007) Single bolus injection of bilirubin improves the clinical outcome in a mouse model of endotoxemia. Shock 28, 582-588.
34. Cao, Q., Jing, C., Tang, X., Yin, Y., Han, X., et al. (2011) Protective effect of resveratrol on acute lung injury induced by lipopolysaccharide in mice. Anat. Rec. (Hoboken) 294, 527-532.
35. Dang, O., Navarro, L., and David, M. (2004) Inhibition of lipopolysaccharide-induced interferon regulatory factor 3 activation and protection from septic shock by hydroxystilbenes. Shock 21, 470-475.