Dimerization, ROS formation, and biological activity of o-methoxyphenols

Archivum Immunologiae et Therapiae Experimentalis

Volumn 53, Issue 1, 2005, Pages 28-38

  Fujisawa, Seiichiro ^a   Atsumi, Toshiko ^a   Murakami, Yukio ^a   Kadoma, Yoshinori ^b  

^a MEIKAI UNIVERSITY SCHOOL OF DENTISTRY   (Japan)

^b TOKYO MEDICAL AND DENTAL UNIVERSITY   (Japan)

Author keywords

Apoptosis; Cooxidation of thiol; Cox 2; Dimerization; NF B; o methoxyphenols; ROS formation; Stoichiometric factors

Indexed keywords

3,3' DIMETHOXY 5,5' DI 2 PROPENYL 1,1' BIPHENYL 2,2' DIOL; 4,8 BIS(4 HYDROXY 3 METHOXYPHENYL) 3,7 DIOXABICYCLO[3.3.0]OCTANE 2,6 DIONE; ALPHA DIISOEUGENOL; ANTIOXIDANT; CATECHIN; CURCUMIN; CYCLOOXYGENASE 2; DEHYDRODIISOEUGENOL; DIMER; EUGENOL; FERULIC ACID; GUAIACOL; IMMUNOGLOBULIN ENHANCER BINDING PROTEIN; ISOEUGENOL; MERCAPTOMETHYLIMIDAZOLE; PHENOL DERIVATIVE; POLYPHENOL; REACTIVE OXYGEN METABOLITE; THIOL DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL CELL; ANTIOXIDANT ACTIVITY; APOPTOSIS; BIOMIMETICS; CANCER CELL; CONTROLLED STUDY; COSMETIC INDUSTRY; DIMERIZATION; DOSE RESPONSE; FOOD INDUSTRY; MOUSE; NONHUMAN; OXYGEN CONSUMPTION; REVIEW;

ANISOLES; ANTIOXIDANTS; APOPTOSIS; CELL LINE; DIMERIZATION; DRUG DESIGN; FREE RADICAL SCAVENGERS; HUMANS; MOLECULAR STRUCTURE; NF-KAPPA B; NITRIC OXIDE; REACTIVE OXYGEN SPECIES;

EID: 14944343245     PISSN: 0004069X     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Review

References (78)

1. Aggawal B., Kumar A. and Bharti A. C. (2003): Anticancer potential of curcumin: preclinical and clinical studies. Anticancer Res., 23, 363-398.
2. Ahmad N., Gupta S. and Mukhtar H. (2000): Green tea polyphenol epigallocatechin-3-gallate differentially modulates nuclear factor κB in cancer cells versus normal cells. Arch. Biochem. Biophys., 376, 338-346.
3. Allen R.G. and Tresini M. (2000): Oxidative stress and gene regulation. Free Radic. Biol. Med., 28, 463-499.
4. Amorati R., Ferroni F., Pedulli G. F. and Valgimigli L. (2003): Modeling the co-antioxidant behavior of monofunctional phenols. Application to some relevant compounds. J. Org. Chem., 68, 9654-9658.
5. Atsumi T., Fujisawa S., Satoh K., Sakagami H., Iwakura I., Ueha T., Sugita Y. and Yokoe I. (2000): Cytotoxicity and radical intensity of eugenol, isoeugenol or related dimers. Anticancer Res., 20, 2519-2524.
6. Atsumi T., Fujisawa S. and Tonosaki K. (2004): Relationship between intercellular ROS production and membrane mobility in curcumin- and tetrahydroxycurcumin-treated human gingival fibroblasts and human submandibular gland carcinoma cells. Oral Dis. (in press).
7. Awasthi S., Pandya U., Singhal S. S., Lin J. T., Thiviyanathan V., Seifert W. E. Jr., Awasthi Y. C. and Ansari G. A. (2000): Curcumin-glutathione interactions and the role of human glutathione S-transferase P1-1. Chem. Biol. Interact., 128, 19-38.
8. Barratt M. D. and Basketter D. A. (1992): Possible origin of the skin sensitization potential of isoeugenol and related compounds. I. Preliminary studies of potential reaction mechanisms. Contact Derm., 27, 98-104.
9. Bergendi L., Benes L., Durackova Z. and Ferenics M. (1999): Chemistry, physiology and pathology of free radicals. Life Sci., 65, 1865-1874.
10. Bhaumik S., Anjum R., Rangaraj N., Pardhasaradhi B. V. and Khar A. (1999): Curcumin mediated apoptosis in AK-5 tumor cells involves the production of reactive oxygen intermediates. FEBS Lett., 456, 311-314.
11. Bolann B. J. and Ulvik R. J. (1990): On the limited ability of superoxide to release iron from ferritin. Eur. J. Biochem., 193, 899-904.
12. Bors W. and Michel C. (1999): Antioxidant capacity of flavanols and gallate esters: pulse radiolysis studies. Free Radic. Biol. Med., 27, 1413-1426.
13. Brand-Williams W., Cuvelier M. E. and Berset C. (1995): Use of a free radical method to evaluate antioxidant activity. Lebenm.-Wiss. U. Technol, 28, 25-30.
14. Brown K., Gerstberger S., Carlson L., Franzoso G. and Siebenlist U. (1995): Control of IκB-α proteolysis by site specific, signal-induced phosphorylation. Science, 267, 1485-1488.
15. Burton G. M. and Ingold K. U. (1981): Autoxidation of biological molecules 1. The antioxidant activity of vitamin E and related chain-breaking phenolic antioxidants in vivo. J. Am. Chem. Soc., 103, 6472-6477.
16. Burton G. W. and Ingold K. U. (1984): β-Carotene. An unusual type of lipid antioxidant. Science, 224, 569-573.
17. Canada A. T., Giannella E., Nguyen T. D. and Mason R. P. (1990): The production of reactive oxygen species by dietary flavonols. Free Radic. Biol. Med., 9, 441-449.
18. Chung L. Y., Cheung T. C., Kong S. K., Fung K. P., Choy Y. M., Chan Z. Y. and Kwok T. T. (2001): Induction of apoptosis by green tea catechins in human prostate cancer DU145 cells. Life Sci., 68, 1207-1214.
19. Decker E. A. (1997): Phenolics: prooxidants or antioxidants? Nutr. Rev., 55, 396-401.
20. Fujisawa S., Atsumi T., Kadoma Y. and Sakagami H. (2002): Antioxidant and prooxidant action of eugenol-related compounds and their cytotoxicity. Toxicology, 177, 39-54.
21. Fujisawa S., Ishihara M. and Kadoma Y. (2002): Kinetic evaluation of the reactivity of flavonoids as radical scavengers. SAR and QSAR in Environ. Res., 13, 617-627.
22. Fujisawa S., Atsumi T., Ishihara M. and Kadoma Y. (2004): Cytotoxicity, ROS-generation activity and radical-scavenging activity of curcumin and related compounds. Anticancer Res., 24, 563-570.
23. Fujisawa, S., Ishihara M. and Kadoma Y. (2004): Kinetics of the radical scavenging activity of β-carotene-related compounds. SAR and QSAR in Environ. Res., 15, 33-41.
24. Fujisawa S., Kadoma Y. and Yokoe I. (2004): Radical-scavenging activity of butylated hydroxytoluene (BHT) and its metabolites. Chem. Phys. Lipids, 130, 189-195.
25. th birthday. Internet Electron. J. Mol. Des., 3, 241-246 (http://www.biochempress.com).
26. Fujisawa S., Atsumi T., Kadoma Y., Ishihara M., Itoh S. and Yokoe I. (2004): Kinetic radical scavenging activity and cytotoxicity of 2-methoxy- and 2-t-butyl-substituted phenols and their dimers. Anticancer Res. (in press).
27. Galati G., Sabzevali O., Wilson J. X. and O'Brien P. J. (2002): Prooxidant activity and cellular effects of the phenoxyl radicals of dietary flavonoids and other polyphenolics. Toxicology, 177, 91-104.
28. Goldman R., Claycamp G. H., Sweetland M. A., Sedlov A. V., Tyurin V. A., Kisin E. R., Tyurina Y. Y., Ritov V. B., Wenger S. L., Grant S. G. and Kagan V. E. (1999): Myeloperoxidase-catalyzed redox-cycling of phenol promotes lipid peroxidation and thiol oxidation in HL-60 cells. Free Radic. Biol. Med., 27, 1050-1063.
29. Hansch C., Bonavida B., Jazirehi A. R., Cohen J. J., Milliron C. and Kurup A. (2003): Quantitative structure-activity relationships of phenolic compounds causing apoptosis. Bioorg. Med. Chem., 11, 617-620.
30. Henkel T., Machleidt T., Alkalay I., Kranke M., Ben-Neriah Y. and Baeuerle P. A. (1993): Rapid proteolysis of IκB-α is necessary for activation of transcription factor NF-κ. Nature, 365, 182-185.
31. Horswill E. C., Howard J. A. and Ingold K. V. (1966): The oxidation of phenols. III. The stoichiometries for the oxidation of some substituted phenols with peroxy radicals. Can. J. Chem., 44. 985-991.
32. Hotta H., Sakamoto H., Nakano S., Osakai T. and Tsujimoto Y. (2001): Unusually large number of electrons for the oxidation of polyphenolic antioxidants. Biochim. Biophys. Acta. 1526, 159-167.
33. Kelm M. A., Nair M. G., Strasburg G. M. and DeWitt D. L. (2000): Antioxidant and cyclooxygenase inhibitory phenolic compounds from Ocimum sanctum Linn. Phytomed., 71, 7-13.
34. 2 supply under normal and pathological conditions. Adv. Exp. Med. Biol., 169, 69-80.
35. Kim S. S., Oh O. J., Min H. Y., Park E. J., Kim Y., Park H. J., Nam Han Y. and Lee S. K. (2003): Eugenol suppresses cyclooxygenase-2 expression in lipopolysaccharide-stimulated mouse macrophage RAW 264.7 cells. Life Sci., 73, 337-348.
36. Kondo K., Kurihara M., Miyata N., Suzuki T. and Toyoda M. (1999): Mechanistic studies of catechins as antioxidants against radical oxidation. Arch. Biochem. Biophys., 362, 79-86.
37. Land E. J. and Swallow A. J. (1971): One-electron reactions in biochemical systems as studied by pulse radiolysis. IV. Oxidation of dihydronicotinamide-adenine dinucleotide. Biochim. Biophys. Acta, 234, 34-42.
38. Legrand-Poels S., Maniglia S., Boelaert R. J. and Piette J. (1997): Activation of the transcription factor NF-κB in lipopolysaccharide- stimulated U937 cells. Biochem. Pharmacol., 53, 339-346.
39. Li J. K. and Lin-Shia S. Y. (2001): Mechanisms of cancer chemo-prevention by curcumin. Proc. Natl. Sci. Counc. Repub. China, B 25, 59-66.
40. Masuda T., Hidaka K., Shinohara A., Maekawa T., Takeda Y. and Yamaguchi H. (1999): Chemical studies on antioxidant mechanism of curcuminoid: analysis of radical reaction products from curcumin. J Agric. Food Chem., 47, 71-77.
41. Masuda T., Toi Y., Bando H., Maekawa T., Takeda Y. and Yamaguchi H. (2002): Structural identification of new curcumin dimers and their contribution to the antioxidant mechanism of curcumin. J Agric. Food Chem., 50, 2524-2530.
42. Masuda T., Maekawa T., Hidaka K., Bando H., Takeda Y. and Yamaguchi H. (2001): Chemical studies on antioxidant mechanism of curcumin: analysis of oxidative coupling products from curcumin and linoleate. J. Agric. Food Chem., 49, 2539-2547.
43. Matsuguchi T., Musikacharoen T., Ogawa T. and Yoshikai Y. (2000): Gene expression of Toll-like receptor 2, but not Toll-like receptor 4, is induced by LPS and inflammatory cytokines in mouse macrophages. J. Immunol., 165, 5767-5772.
44. Middleton E. and Kandaswami C. (1994): The impact of plant flavonoids on mammalian biology: implications for immunity, inflammation and cancer. In Harborne J. B. (ed.): The Flavonoids: Advances in Research since 1986. Chapman & Hall, London, pp. 619-652.
45. Murakami, Y., Shoji M., Hanazawa S., Tanaka S. and Fujisawa S. (2003): Preventive effect of bis-eugenol, a eugenol ortho dimer, and inflammatory cytokine expression in macrophages. Biochem. Pharmacol., 66, 1061-1066.
46. Niki E., Saito T., Kawakami A. and Kamiya Y. (1984): Inhibition of oxidation of methyl linoleate in solution by vitamin E and vitamin C. J. Biol. Chem., 259, 4177-4182.
47. Nogaki A., Satoh K., Iwasaka K., Takano H., Takahama M., Ida Y. and Sakagami H. (1998): Radical intensity and cytotoxic activity of curcumin and gallic acid. Anticancer Res., 18, 3487-3491.
48. Ogata M., Hoshi M., Urano S. and Endo T. (2000): Antioxidant activity of eugenol and related monomeric and dimeric compounds. Chem. Pharma. Bull., 48, 1467-1469.
49. Ogiwara T., Satoh K., Kadoma Y., Murakami Y., Unten S., Atsumi T., Sakagami H. and Fujisawa S. (2002): Radical scavenging activity and cytotoxicity of ferulic acid. Anticancer Res., 22. 2711-2718.
50. Ogiwara T., Satoh K., Negoro T., Okayasu H., Sakagami H. and Fujisawa S. (2003): Inhibition of NO production by activated macrophages by phenolcarboxylic acid monomers and polymers with radical scavenging activity. Anticancer Res., 23, 1317-1323.
51. Pan M. H., Lin-Shiau S. Y. and Lin J. K. (2000): 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., 60, 1665-1676.
52. Park S., Lee D. K. and Yang C. H. (1998): Inhibition of fos-jun-DNA complex formation by dihydroguaiaretic acid and in vitro cytotoxic effects on cancer cells. Cancer Lett., 127, 23-28.
53. Pelicano H., Carney D. and Huang P. (2004): ROS stress in cancer cells and therapeutic implications. Drug Resist. Updat, 7, 97-110.
54. Pervaiz S. and Clement M. V. (2004): Tumor intracellular redox status and drug resistance - serendipity or a causal relationship? Curr. Pharm. Des., 10, 1969-1977.
55. Priyadarsini K. I. (1997): Free radical reactions of curcumin in membrane models. Free Radic. Biol. Med., 23, 838-843.
56. Pryor W. A., Stricland T. and Church D. F. (1988): Comparison of the efficiencies of several natural and synthetic antioxidants in aqueous sodium dodecyl sulfate micelle solutions. J. Am. Chem. Soc., 110, 2224-2229.
57. Roginsky V. (2003): Chain-breaking antioxidant activity of natural polyphenols as determined during the chain oxidation of methyl linoleate in Triton-X-100 micelles. Arch. Biochem. Biophys., 414, 261-270.
58. Saeki K., Kobayashi N., Inazawa Y., Zhang H., Nishitoh H., Ichijo H., Saeki K., Isemura M. and Yuo A. (2002): Oxidation-triggered c-Jun N-terminal kinase (JNK) and p38 mitogen-activated protein (MAP) kinase pathways for apoptosis in human leukaemic cells stimulated by epigallocatechin-3-gallate (EGCG): a distinct pathway from those of chemically induced and receptor-mediated apoptosis. Biochem J., 368 (Pt 3), 705-720.
59. Saito M., Sakagami H. and Fujisawa S. (2003): Cytotoxicity and apoptosis induction by butylated hydroxyanisole (BHA) and butylated hydroxytoluene (BHT). Anticancer Res., 23, 4693-4701.
60. Satoh K., Sakagami H., Terasaka H., Ida Y. and Fujisawa S. (2000): Interaction between hydroquinone and ascorbic acid derivatives: quenching effect of organic solvents. Anticancer Res., 20, 1577-1581.
61. Smith D. M., and Dou Q. P. (2001): Green tea polyphenol epigallocatechin inhibits DNA replication and consequently induces leukemia cell apoptosis. Int. J. Mol. Med., 7, 645-652.
62. Soriani M., Pietraforte D. and Minetti M. (1994): Antioxidant potential of anaerobic human plasma: role of serum albumin and thiols as scavengers of carbon radicals. Arch. Biochem. Biophys, 312, 180-188.
63. Storey K. B. (1996): Oxidative stress: animal adaptations in nature. Braz. J. Med. Biol. Res., 29, 1715-1733.
64. Surh Y. J. (2002): Anti-tumor promoting potential of selected spice ingredients with antioxidative and anti-inflammatory activities: a short review. Food Chem. Toxicol., 40, 1091-1097.
65. Suzuki Y., Ono Y. and Hirabayashi Y. (1998): Rapid and specific reactive oxygen species generation via NADPH oxidase activation during Fas-mediated apoptosis. FEBS Lett., 425, 209-212.
66. Taira J., Yoneyama T., Hagi A., Murakami A. and Makino K. (1992): Essential oil phenyl propanoids. Useful as OH scavengers? Free Radic. Res. Commun., 16, 197-204.
67. Thompson D., Norbec K., Olsson L., Constantin-Teodosiu, D., van der Zee J. and Moldeus P. (1989): Peroxidase-catalyzed oxidation of eugenol: formation of a cytotoxic metabolite(s). J. Biol. Chem., 264, 1016-1021.
68. Thompson D. C., Thompson J.A., Suguraman M. and Moldeus P. (1991): Biological and toxicological consequences of quinone methide formation. Chem. Biol. Interact., 86, 129-162.
69. Thompson C. B. (1995): Apoptosis in the pathogenesis and treatment of disease. Science, 267, 1456-1462.
70. Tomba M. and Simone G. (1986): Interaction of thiyl free radicals with oxygen: a pulse radiolysis study. Int. J. Radiat. Biol., 50, 595-600.
71. Tonnesen H. H., de Vries H., Karlsen J. and Beijersbergen van Henegouwen G. (1987): Studies on curcumin and curcuminoids. IX. Investigation of the photobiological activity of curcumin using bacterial indicator systems. J. Pharm. Sci., 76, 371-373.
72. Toniolo R., Di Narda F., Susmel S., Martelli M., Martelli L. and Bontempelli G. (2002): Quenching of Superoxide ions by curcumin. A mechanistic study in acetonitrile. Ann. Chim., 92, 281-288.
73. Wang C. Y., Mayo M. W., Korneluk R. G., Goeddel D. V. and Baldwin A. S. Jr. (1998): NF-κB antiapoptosis: induction of TRAF1 and TRAF2 and c-IAP1 and C-IAP2 to suppress caspase-8 activation. Science, 281, 1680-1683.
74. Watanabe A., Takeshita A., Kitano S. and Hanazawa S. (1996): CD14-mediated signal pathway of Porphyromonas gingivalis lipopolysaccharide in human gingival fibroblasts. Infect. Immun., 64, 4488-4494.
75. Wiseman A. (2004): Dietary alkyl thiol free radicals (RSS) can be as toxic as reactive oxygen species (ROS). Med. Hypotheses, 63, 667-670.
76. Wright J. S., Carpenter D. J., Mckay D. J. and Ingold K. U. (1997): Theoretical calculation of substituent effect on O-H bond strength of phenolic antioxidants related to vitamin E. J. Am. Chem. Soc., 119, 4245-4252.
77. Zhang C. P., Xie Y. Z., Chen P., Hong X., Xiao Z. H., Ma Y. and Lu Y. D. (2004): Nuclear factor κB signal transduction in macrophages during hypoxia: reactive oxygen species generation. Sheng Li Xue Bao, 56, 515-520.
78. Zhou Y., Hileman E. O., Plunkett W., Keating M. J. and Huang P. (2003): Free radical stress in chronic lymphocytic leukemia cells and anticancer agents. Blood, 101, 4098-4104.