Honokiol is a potent scavenger of superoxide and peroxyl radicals

Biochemical Pharmacology

Volumn 76, Issue 5, 2008, Pages 589-596

  Dikalov, Sergey ^a   Losik, Tanya ^a   Arbiser, Jack L ^a  

^a EMORY UNIVERSITY SCHOOL OF MEDICINE   (United States)

Author keywords

Antioxidant; Electron spin resonance; Honokiol; Melanoma; Superoxide

Indexed keywords

2,2' AZOBIS(2 AMIDINOPROPANE); ASCORBIC ACID; CYTOCHROME P450; HONOKIOL; IMMUNOGLOBULIN ENHANCER BINDING PROTEIN; MAGNOLIA OFFICINALIS EXTRACT; PEROXY RADICAL; REACTIVE OXYGEN METABOLITE; SCAVENGER; SUPEROXIDE; TROLOX C; XANTHINE OXIDASE;

ANTIANGIOGENIC ACTIVITY; ANTINEOPLASTIC ACTIVITY; ANTIOXIDANT ACTIVITY; ARTICLE; CELL CULTURE; CELL FREE SYSTEM; CONTROLLED STUDY; DRUG POTENCY; DRUG STRUCTURE; ELECTRON SPIN RESONANCE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; HUMAN CELL; MELANOMA CELL; OXIDATIVE STRESS; PRIORITY JOURNAL; REACTION TIME; SPIN TRAPPING; STATISTICAL ANALYSIS;

EID: 49149119432     PISSN: 00062952     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bcp.2008.06.012     Document Type: Article

References (52)

1. Bai X., Cerimele F., Ushio-Fukai M., Waqas M., Campbell P.M., Govindarajan B., et al. Honokiol, a small molecular weight natural product, inhibits angiogenesis in vitro and tumor growth in vivo. J Biol Chem 278 (2003) 35501-35507
2. Ishitsuka K., Hideshima T., Hamasaki M., Raje N., Kumar S., Hideshima H., et al. Honokiol overcomes conventional drug resistance in human multiple myeloma by induction of caspase-dependent and -independent apoptosis. Blood 106 (2005) 1794-1800
3. Battle T.E., Arbiser J., and Frank D.A. The natural product honokiol induces caspase-dependent apoptosis in B-cell chronic lymphocytic leukemia (B-CLL) cells. Blood 106 (2005) 690-697
4. Chawla-Sarkar M., Bauer J.A., Lupica J.A., Morrison B.H., Tang Z., Oates R.K., et al. Suppression of NF-kappa B survival signaling by nitrosylcobalamin sensitizes neoplasms to the anti-tumor effects of Apo2L/TRAIL. J Biol Chem 278 (2003) 39461-39469
5. Oberley L.W., and Buettner G.R. Role of superoxide dismutase in cancer: a review. Cancer Res 39 (1979) 1141-1149
6. Ahn K.S., Sethi G., Shishodia S., Sung B., Arbiser J.L., and Aggarwal B.B. Honokiol potentiates apoptosis, suppresses osteoclastogenesis, and inhibits invasion through modulation of nuclear factor-kappaB activation pathway. Mol Cancer Res 4 (2006) 621-633
7. Schreck R., Rieber P., and Baeuerle P.A. Reactive oxygen intermediates as apparently widely used messengers in the activation of the NF-kappa B transcription factor and HIV-1. EMBO J 10 (1991) 2247-2258
8. Samlowski W.E., Petersen R., Cuzzocrea S., Macarthur H., Burton D., McGregor J.R., et al. A nonpeptidyl mimic of superoxide dismutase, M40403, inhibits dose-limiting hypotension associated with interleukin-2 and increases its antitumor effects. Nat Med 9 (2003) 750-755
9. Traber M.G., and Atkinson J. Vitamin E, antioxidant and nothing more. Free Radic Biol Med 43 (2007) 4-15
10. Cao G., Sofic E., and Prior R.L. Antioxidant and prooxidant behavior of flavonoids: structure-activity relationships. Free Radic Biol Med 22 (1997) 749-760
11. Chiu J.H., Ho C.T., Wei Y.H., Lui W.Y., and Hong C.Y. In vitro and in vivo protective effect of honokiol on rat liver from peroxidative injury. Life Sci 61 (1997) 1961-1971
12. Ou H.C., Chou F.P., Lin T.M., Yang C.H., and Sheu W.H. Protective effects of honokiol against oxidized LDL-induced cytotoxicity and adhesion molecule expression in endothelial cells. Chem Biol Interact 161 (2006) 1-13
13. Oettl K., Dikalov S., Freisleben H.J., Mlekusch W., and Reibnegger G. Spin trapping study of antioxidant properties of neopterin and 7, 8-dihydroneopterin. Biochem Biophys Res Commun 234 (1997) 774-778
14. Kuzkaya N., Weissmann N., Harrison D.G., and Dikalov S. Interactions of peroxynitrite, tetrahydrobiopterin, ascorbic acid, and thiols: implications for uncoupling endothelial nitric-oxide synthase. J Biol Chem 278 (2003) 22546-22554
15. Benov L., Sztejnberg L., and Fridovich I. Critical evaluation of the use of hydroethidine as a measure of superoxide anion radical. Free Radic Biol Med 25 (1998) 826-831
16. Zhao H., Joseph J., Fales H.M., Sokoloski E.A., Levine R.L., Vasquez-Vivar J., et al. Detection and characterization of the product of hydroethidine and intracellular superoxide by HPLC and limitations of fluorescence. Proc Natl Acad Sci USA 102 (2005) 5727-5732
17. Dikalov S., Griendling K.K., and Harrison D.G. Measurement of reactive oxygen species in cardiovascular studies. Hypertension 49 (2007) 717-727
18. Zhang H., Joseph J., Vasquez-Vivar J., Karoui H., Nsanzumuhire C., Martasek P., et al. Detection of superoxide anion using an isotopically labeled nitrone spin trap: potential biological applications. FEBS Lett 473 (2000) 58-62
19. Dikalov S.I., and Mason R.P. Reassignment of organic peroxyl radical adducts. Free Radic Biol Med 27 (1999) 864-872
20. Dikalov S., Jiang J., and Mason R.P. Characterization of the high-resolution ESR spectra of superoxide radical adducts of 5-(diethoxyphosphoryl)-5-methyl-1-pyrroline N-oxide (DEPMPO) and 5,5-dimethyl-1-pyrroline N-oxide (DMPO). Analysis of conformational exchange. Free Radic Res 39 (2005) 825-836
21. Dikalov S., Landmesser U., and Harrison D.G. Geldanamycin leads to superoxide formation by enzymatic and non-enzymatic redox cycling Implications for studies of Hsp90 and endothelial cell nitric-oxide synthase. J Biol Chem 277 (2002) 25480-25485
22. Duling D.R. Simulation of multiple isotropic spin-trap EPR spectra. J Magn Reson B 104 (1994) 105-110
23. Liang J., Zubovitz J., Petrocelli T., Kotchetkov R., Connor M.K., Han K., et al. PKB/Akt phosphorylates p27, impairs nuclear import of p27 and opposes p27-mediated G1 arrest. Nat Med 8 (2002) 1153-1160
24. Kuzkaya N., Weissmann N., Harrison D.G., and Dikalov S. Interactions of peroxynitrite with uric acid in the presence of ascorbate and thiols: implications for uncoupling endothelial nitric oxide synthase. Biochem Pharmacol 70 (2005) 343-354
25. Mitsuta K., Mizuta Y., Kohno M., Hiramatsu M., and Mori A. Reaction of superoxide with ascorbate. Bull Chem Soc Jpn 63 (1990) 187-191
26. Taubert D., Breitenbach T., Lazar A., Censarek P., Harlfinger S., Berkels R., et al. Reaction rate constants of superoxide scavenging by plant antioxidants. Free Radic Biol Med 35 (2003) 1599-1607
27. Dikalov S.I., and Mason R.P. Spin trapping of polyunsaturated fatty acid-derived peroxyl radicals: reassignment to alkoxyl radical adducts. Free Radic Biol Med 30 (2001) 187-197
28. Simic M.G. Peroxyl radical from oleic acid. Autoxid Food Biol Syst (1980) 17-26
29. Bickers D.R., and Athar M. Oxidative stress in the pathogenesis of skin disease. J Invest Dermatol 126 (2006) 2565-2575
30. Arbiser J.L., Petros J., Klafter R., Govindajaran B., McLaughlin E.R., Brown L.F., et al. Reactive oxygen generated by Nox1 triggers the angiogenic switch. Proc Natl Acad Sci USA 99 (2002) 715-720
31. Petros J.A., Baumann A.K., Ruiz-Pesini E., Amin M.B., Sun C.Q., Hall J., et al. mtDNA mutations increase tumorigenicity in prostate cancer. Proc Natl Acad Sci USA 102 (2005) 719-724
32. Podda M., Zollner T.M., Grundmann-Kollmann M., Thiele J.J., Packer L., and Kaufmann R. Activity of alpha-lipoic acid in the protection against oxidative stress in skin. Curr Probl Dermatol 29 (2001) 43-51
33. Khan N., Afaq F., Saleem M., Ahmad N., and Mukhtar H. Targeting multiple signaling pathways by green tea polyphenol (-)-epigallocatechin-3-gallate. Cancer Res 66 (2006) 2500-2505
34. Mantena S.K., Meeran S.M., Elmets C.A., and Katiyar S.K. Orally administered green tea polyphenols prevent ultraviolet radiation-induced skin cancer in mice through activation of cytotoxic T cells and inhibition of angiogenesis in tumors. J Nutr 135 (2005) 2871-2877
35. Wallace D.C. A mitochondrial paradigm of metabolic and degenerative diseases, aging, and cancer: a dawn for evolutionary medicine. Annu Rev Genet 39 (2005) 359-407
36. Eshaghian A., Vleugels R.A., Canter J.A., McDonald M.A., Stasko T., and Sligh J.E. Mitochondrial DNA deletions serve as biomarkers of aging in the skin, but are typically absent in nonmelanoma skin cancers. J Invest Dermatol 126 (2006) 336-344
37. Tsai S.K., Huang S.S., and Hong C.Y. Myocardial protective effect of honokiol: an active component in Magnolia officinalis. Planta Med 62 (1996) 503-506
38. Liou K.T., Shen Y.C., Chen C.F., Tsao C.M., and Tsai S.K. The anti-inflammatory effect of honokiol on neutrophils: mechanisms in the inhibition of reactive oxygen species production. Eur J Pharmacol 475 (2003) 19-27
39. Zhang W.J., and Frei B. Intracellular metal ion chelators inhibit TNFalpha-induced SP-1 activation and adhesion molecule expression in human aortic endothelial cells. Free Radic Biol Med 34 (2003) 674-682
40. Ramana K.V., Bhatnagar A., Srivastava S., Yadav U.C., Awasthi S., Awasthi Y.C., et al. Mitogenic responses of vascular smooth muscle cells to lipid peroxidation-derived aldehyde 4-hydroxy-trans-2-nonenal (HNE): role of aldose reductase-catalyzed reduction of the HNE-glutathione conjugates in regulating cell growth. J Biol Chem 281 (2006) 17652-17660
41. Watanabe N., Zmijewski J.W., Takabe W., Umezu-Goto M., Le Goffe C., Sekine A., et al. Activation of mitogen-activated protein kinases by lysophosphatidylcholine-induced mitochondrial reactive oxygen species generation in endothelial cells. Am J Pathol 168 (2006) 1737-1748
42. Huie R.E., and Padmaja S. The reaction of NO with superoxide. Free Radic Res Commun 18 (1993) 195-199
43. Thomas D.D., Ridnour L.A., Espey M.G., Donzelli S., Ambs S., Hussain S.P., et al. Superoxide fluxes limit nitric oxide-induced signaling. J Biol Chem (2006)
44. Son H.J., Lee H.J., Yun-Choi H.S., and Ryu J.H. Inhibitors of nitric oxide synthesis and TNF-alpha expression from Magnolia obovata in activated macrophages. Planta Med 66 (2000) 469-471
45. Jiang F., Guo N., and Dusting G.J. Modulation of nicotinamide adenine dinucleotide phosphate oxidase expression and function by 3′,4′-dihydroxyflavonol in phagocytic and vascular cells. J Pharmacol Exp Ther 324 (2008) 261-269
46. Steffen Y., Gruber C., Schewe T., and Sies H. Mono-O-methylated flavanols and other flavonoids as inhibitors of endothelial NADPH oxidase. Arch Biochem Biophys 469 (2008) 209-219
47. Alberts D.S., Goldman R., Xu M.J., Dorr R.T., Quinn J., Welch K., et al. Disposition and metabolism of topically administered alpha-tocopherol acetate: a common ingredient of commercially available sunscreens and cosmetics. Nutr Cancer 26 (1996) 193-201
48. Mehlhorn R.J., Sumida S., and Packer L. Tocopheroxyl radical persistence and tocopherol consumption in liposomes and in vitamin E-enriched rat liver mitochondria and microsomes. J Biol Chem 264 (1989) 13448-13452
49. Kagan V.E., Freisleben H.J., Tsuchiya M., Forte T., and Packer L. Generation of probucol radicals and their reduction by ascorbate and dihydrolipoic acid in human low density lipoproteins. Free Radic Res Commun 15 (1991) 265-276
50. Zhao A., Wu Z.Q., Pollack M., Rollwagen F.M., Hirszel P., and Zhou X. Disulfiram inhibits TNF-alpha-induced cell death. Cytokine 12 (2000) 1356-1367
51. Meyskens Jr. F.L., McNulty S.E., Buckmeier J.A., Tohidian N.B., Spillane T.J., Kahlon R.S., et al. Aberrant redox regulation in human metastatic melanoma cells compared to normal melanocytes. Free Radic Biol Med 31 (2001) 799-808
52. Brar S.S., Grigg C., Wilson K.S., Holder Jr. W.D., Dreau D., Austin C., et al. Disulfiram inhibits activating transcription factor/cyclic AMP-responsive element binding protein and human melanoma growth in a metal-dependent manner in vitro, in mice and in a patient with metastatic disease. Mol Cancer Ther 3 (2004) 1049-1060