Piceatannol, a hydroxystilbene natural product, stabilizes HIF-1α protein by inhibiting HIF prolyl hydroxylase

European Journal of Pharmacology

Volumn 699, Issue 1-3, 2013, Pages 124-131

  Yum, Soohwan ^a   Doh, Hea Jeong ^a   Hong, Sungchae ^a   Jeong, Seongkeun ^a   Kim, Dae Duk ^b   Park, Misun ^c   Jung, Yunjin ^a  

^a Pusan National University   (South Korea)

^b Seoul National University   (South Korea)

^c RUTGERS NEW JERSEY MEDICAL SCHOOL   (United States)

Author keywords

Colitis; HIF prolyl hydroxylase; Hypoxia inducible factor 1; Piceatannol; Structural analysis

Indexed keywords

2 OXOGLUTARIC ACID; ASCORBIC ACID; CATECHOL; HEME OXYGENASE 1; HYPOXIA INDUCIBLE FACTOR; HYPOXIA INDUCIBLE FACTOR 1; HYPOXIA INDUCIBLE FACTOR 1ALPHA; PICEATANNOL; PROCOLLAGEN PROLINE 2 OXOGLUTARATE 4 DIOXYGENASE; RESORCINOL; RESVERATROL; SMALL INTERFERING RNA; VASCULOTROPIN; VON HIPPEL LINDAU PROTEIN;

ANIMAL CELL; ARTICLE; CARCINOMA CELL; COLITIS; COLON CARCINOMA; CONTROLLED STUDY; DRUG MECHANISM; DRUG STRUCTURE; ENZYME INHIBITION; HUMAN; HYDROXYLATION; IMMUNOPRECIPITATION; NONHUMAN; PRIORITY JOURNAL; PROTEIN DEGRADATION; PROTEIN EXPRESSION; PROTEIN PROCESSING; PROTEIN SECRETION; PROTEIN STABILITY;

ASCORBIC ACID; CELL LINE, TUMOR; COLITIS; COLONIC NEOPLASMS; HEK293 CELLS; HEME OXYGENASE-1; HUMANS; HYPOXIA-INDUCIBLE FACTOR 1, ALPHA SUBUNIT; HYPOXIA-INDUCIBLE FACTOR-PROLINE DIOXYGENASES; PROCOLLAGEN-PROLINE DIOXYGENASE; STILBENES; VASCULAR ENDOTHELIAL GROWTH FACTOR A;

EID: 84871917347     PISSN: 00142999     EISSN: 18790712     Source Type: Journal    
DOI: 10.1016/j.ejphar.2012.12.008     Document Type: Article

References (33)

1. B.B. Aggarwal, G. Sethi, K.S. Ahn, S.K. Sandur, M.K. Pandey, A.B. Kunnumakkara, B. Sung, and H. Ichikawa Targeting signal-transducer-and- activator-of-transcription-3 for prevention and therapy of cancer: modern target but ancient solution Ann. N. Y. Acad. Sci. 1091 2006 151 169
2. N.C. Andrews, and D.V. Faller A rapid micropreparation technique for extraction of DNA-binding proteins from limiting numbers of mammalian cells Nucleic Acids Res. 19 1991 2499
3. K. Ashikawa, S. Majumdar, S. Banerjee, A.C. Bharti, S. Shishodia, and B.B. Aggarwal Piceatannol inhibits TNF-induced NF-kappaB activation and NF-kappaB-mediated gene expression through suppression of IkappaBalpha kinase and p65 phosphorylation J. Immunol. 169 2002 6490 6497
4. R.K. Bruick, and S.L. McKnight A conserved family of prolyl-4- hydroxylases that modify HIF Science 294 2001 1337 1340
5. A. Chernoguz, K. Crawford, A. Vandersall, M. Rao, T. Willson, L.A. Denson, and J.S. Frischer Pretreatment with anti-VEGF therapy may exacerbate inflammation in experimental acute colitis J. Pediatr. Surg. 47 2012 347 354
6. D. Choi, J. Han, Y. Lee, J. Choi, S. Han, S. Hong, H. Jeon, Y.M. Kim, and Y. Jung Caffeic acid phenethyl ester is a potent inhibitor of HIF prolyl hydroxylase: structural analysis and pharmacological implication J. Nutr. Biochem 2009
7. M.E. Cockman, N. Masson, D.R. Mole, P. Jaakkola, G.W. Chang, S.C. Clifford, E.R. Maher, C.W. Pugh, P.J. Ratcliffe, and P.H. Maxwell Hypoxia inducible factor-alpha binding and ubiquitylation by the von Hippel-Lindau tumor suppressor protein J. Biol. Chem. 275 2000 25733 25741
8. E.P. Cummins, F. Seeballuck, S.J. Keely, N.E. Mangan, J.J. Callanan, P.G. Fallon, and C.T. Taylor The hydroxylase inhibitor dimethyloxalylglycine is protective in a murine model of colitis Gastroenterology 134 2008 156 165
9. D.L. Gillespie, K. Whang, B.T. Ragel, J.R. Flynn, D.A. Kelly, and R.L. Jensen Silencing of hypoxia inducible factor-1alpha by RNA interference attenuates human glioma cell growth in vivo Clin. Cancer Res. 13 2007 2441 2448
10. K.S. Hewitson, and C.J. Schofield The HIF pathway as a therapeutic target Drug Discov. Today 9 2004 704 711
11. S.A. Hirota, K. Fines, J. Ng, D. Traboulsi, J. Lee, E. Ihara, Y. Li, W.G. Willmore, D. Chung, M.M. Scully, T. Louie, S. Medlicott, M. Lejeune, K. Chadee, G. Armstrong, S.P. Colgan, D.A. Muruve, J.A. MacDonald, and P.L. Beck Hypoxia-inducible factor signaling provides protection in Clostridium difficile-induced intestinal injury Gastroenterology 139 259-269 2010 e253
12. M. Hirsila, P. Koivunen, V. Gunzler, K.I. Kivirikko, and J. Myllyharju Characterization of the human prolyl 4-hydroxylases that modify the hypoxia-inducible factor J. Biol. Chem. 278 2003 30772 30780
13. 2-dependent degradation domain via the ubiquitin-proteasome pathway Proc. Natl. Acad. Sci. U. S. A. 95 1998 7987 7992
14. J.S. Isaacs, Y.J. Jung, E.G. Mimnaugh, A. Martinez, F. Cuttitta, and L.M. Neckers Hsp90 regulates a von Hippel-Lindau-independent hypoxia-inducible factor-1 alpha-degradative pathway J. Biol. Chem. 277 2002 29936 29944
15. 2 sensing Science 292 2001 464 468
16. 2-regulated prolyl hydroxylation Science 292 2001 468 472
17. H. Jeon, H. Kim, D. Choi, D. Kim, S.Y. Park, Y.J. Kim, Y.M. Kim, and Y. Jung Quercetin activates an angiogenic pathway, hypoxia inducible factor (HIF)-1-vascular endothelial growth factor, by inhibiting HIF-prolyl hydroxylase: a structural analysis of quercetin for inhibiting HIF-prolyl hydroxylase Mol. Pharmacol. 71 2007 1676 1684
18. Y.J. Jung, J.S. Isaacs, S. Lee, J. Trepel, and L. Neckers Microtubule disruption utilizes an NFkappa B-dependent pathway to stabilize HIF-1alpha protein J. Biol. Chem. 278 2003 7445 7452
19. Y.H. Kim, H.S. Kwon, D.H. Kim, H.J. Cho, H.S. Lee, J.G. Jun, J.H. Park, and J.K. Kim Piceatannol, a stilbene present in grapes, attenuates dextran sulfate sodium-induced colitis Int. Immunopharmacol. 8 2008 1695 1702
20. K.I. Kivirikko, R. Myllyla, and T. Pihlajaniemi Protein hydroxylation: prolyl 4-hydroxylase, an enzyme with four cosubstrates and a multifunctional subunit FASEB J. 3 1989 1609 1617
21. H.H. Lee, S.A. Park, I. Almazari, E.H. Kim, H.K. Na, and Y.J. Surh Piceatannol induces heme oxygenase-1 expression in human mammary epithelial cells through activation of ARE-driven Nrf2 signaling Arch. Biochem. Biophys. 501 2010 142 150
22. H. Piotrowska, M. Kucinska, and M. Murias Biological activity of piceatannol: leaving the shadow of resveratrol Mutat. Res. 750 2012 60 82
23. A. Robinson, S. Keely, J. Karhausen, M.E. Gerich, G.T. Furuta, and S.P. Colgan Mucosal protection by hypoxia-inducible factor prolyl hydroxylase inhibition Gastroenterology 134 2008 145 155
24. S. Salceda, and J. Caro Hypoxia-inducible factor 1alpha (HIF-1alpha) protein is rapidly degraded by the ubiquitin-proteasome system under normoxic conditions. Its stabilization by hypoxia depends on redox-induced changes J. Biol. Chem. 272 1997 22642 22647
25. 2 homeostasis Curr. Opin. Genet. Dev. 8 1998 588 594
26. S.Z. Sheikh, R.A. Hegazi, T. Kobayashi, J.C. Onyiah, S.M. Russo, K. Matsuoka, A.R. Sepulveda, F. Li, L.E. Otterbein, and S.E. Plevy An anti-inflammatory role for carbon monoxide and heme oxygenase-1 in chronic Th2-mediated murine colitis J. Immunol. 186 2011 5506 5513
27. P.S. Son, S.A. Park, H.K. Na, D.M. Jue, S. Kim, and Y.J. Surh 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 31 2010 1442 1449
28. M.M. Tambuwala, E.P. Cummins, C.R. Lenihan, J. Kiss, M. Stauch, C.C. Scholz, P. Fraisl, F. Lasitschka, M. Mollenhauer, S.P. Saunders, P.H. Maxwell, P. Carmeliet, P.G. Fallon, M. Schneider, and C.T. Taylor Loss of prolyl hydroxylase-1 protects against colitis through reduced epithelial cell apoptosis and increased barrier function Gastroenterology 139 2010 2093 2101
29. K. Tanimoto, Y. Makino, T. Pereira, and L. Poellinger Mechanism of regulation of the hypoxia-inducible factor-1 alpha by the von Hippel-Lindau tumor suppressor protein EMBO J. 19 2000 4298 4309
30. A.S. Tarnawski Cellular and molecular mechanisms of gastrointestinal ulcer healing Dig. Dis. Sci. 50 Suppl. 1 2005 S24 S33
31. 2 tension Proc. Natl. Acad. Sci. U. S. A. 92 1995 5510 5514
32. W.P. Wang, X. Guo, M.W. Koo, B.C. Wong, S.K. Lam, Y.N. Ye, and C.H. Cho Protective role of heme oxygenase-1 on trinitrobenzene sulfonic acid-induced colitis in rats Am. J. Physiol. Gastrointest. Liver Physiol. 281 2001 G586 G594
33. J. Youn, J.S. Lee, H.K. Na, J.K. Kundu, and Y.J. Surh Resveratrol and piceatannol inhibit iNOS expression and NF-kappaB activation in dextran sulfate sodium-induced mouse colitis Nutr. Cancer 61 2009 847 854