Comparative anti-inflammatory activities of curcumin and tetrahydrocurcumin based on the phenolic O-H bond dissociation enthalpy, ionization potential and quantum chemical descriptor

Anticancer Research

Volumn 28, Issue 2 A, 2008, Pages 699-707

  Murakami, Yukio ^a   Ishii, Hiroaki ^a   Takada, Naokj ^a   Tanaka, Shoji ^a   Machino, Mamoru ^a   Ito, Shigeru ^b   Fujisawa, Seiichiro ^a  

^a MEIKAI UNIVERSITY SCHOOL OF DENTISTRY   (Japan)

^b TOKYO MEDICAL AND DENTAL UNIVERSITY   (Japan)

Author keywords

Chemical descriptors; COX 2; Curcumin; Lipopolysaccharide; NF B; Porphyromonas gingivalis fimbriae; Tetrahydrocurcumin

Indexed keywords

CURCUMIN; CYCLOOXYGENASE 2; EUGENOL; IMMUNOGLOBULIN ENHANCER BINDING PROTEIN; LIPOPOLYSACCHARIDE; TETRAHYDROCURCUMIN; UNCLASSIFIED DRUG;

ANTIINFLAMMATORY ACTIVITY; ARTICLE; CELL ACTIVATION; COMPARATIVE STUDY; DENSITY FUNCTIONAL THEORY; DRUG EFFECT; DRUG INHIBITION; DRUG STRUCTURE; ENTHALPY; GENE EXPRESSION; IONIZATION; NORTHERN BLOTTING; PRIORITY JOURNAL;

ANIMALS; ANTI-INFLAMMATORY AGENTS; CELL LINE; CURCUMIN; CYCLOOXYGENASE 2; CYCLOOXYGENASE 2 INHIBITORS; HYDROGEN BONDING; HYDROXIDES; LIPOPOLYSACCHARIDES; MICE; PHENOL; PORPHYROMONAS GINGIVALIS; PROTEIN-SERINE-THREONINE KINASES;

EID: 42549172316     PISSN: 02507005     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (38)

1. Aggarwal BB, Bhatt ID, Ichikawa H, Ahn KS, Sethi G, Sandur SK, Natarajan C, Seeram N and Shishodia S: Curcumin: biological and medicinal properties. In: Turmeric: The Genus Curcuma. Ravindran PN, Nirmal Babu K and Sivaraman K (eds.). Series: Medicinal and Aromatic Plants - Industrial Profiles Volume: 45. CRC Press, New York, USA, 2007.
2. Murakami Y, Shoji M, Ogiwara T, Tanaka S, Yokoe I and Fujisawa S: Preventive effect of ortho dimer of butylated hydroxyanisole on activator protein-1 activation and cyclooxygenase-2 expression in macrophages stimulated by fimbriae of Porphyromonas gingivalis, an oral anaerobe. Anticancer Res 26: 2915-2920, 2006.
3. Murakami Y, Shoji M, Hirata A, Tanaka S, Hanazawa S, Yokoe I and Fujisawa S: An ortho dimer of butylated hydroxyanisole inhibits nuclear factor kappa B activation and gene expression of inflammatory cytokines in macrophages stimulated by Porphyromonas gingivalis fimbriae. Arch Biochem Biophys 449: 171-177, 2006.
4. Kim SS, Oh OJ, Min HY, Park EJ, Kim Y, Park HJ, Nam Han Y and Lee SK: Eugenol suppresses cyclooxygenase-2 expression in lipopolysaccharide-stimulated mouse macrophage RAW264.7 cells. Life Sci 73: 337-348, 2003.
5. Murakami Y, Shoji M, Hanazawa S, Tanaka S and Fujisawa S: Preventive effect of bis-eugenol, a eugenol ortho dimer, on lipopolysaccharide-stimulated nuclear factor kappa B activation and inflammatory cytokine expression in macrophages. Biochem Pharmacol 66: 1061-1066, 2003.
6. Murakami Y, Shoji M, Hirata A, Tanaka S, Yokoe I and Fujisawa S: Dehydrodiisoeugenol, an isoeugenol dimer, inhibits lipopolysaccharide-stimulated nuclear factor kappa B activation and cyclooxygenase-2 expression in macrophages. Arch Biochem Biophys 434: 326-332, 2005.
7. Price SL: The computational prediction of pharmaceutical crystal structures and polymorphism. Adv Drug Deliv Rev 56: 301-319, 2004.
8. Yoshimura F, Takahashi K, Nodasaka Y and Suzuki T: Purification and characterization of a novel type of fimbriae from the oral anaerobe Bacteroides gingivalis. J Bacteriol 160: 949-954, 1984.
9. Kawata Y, Hanazawa S, Amano S, Murakami Y, Matsumoto T, Nishida K and Kitano S: Porphyromonas gingivalis fimbriae stimulate bone resorption in vitro. Infect Immun 62: 3012-3016, 1994.
10. Bradford MM: A rapid and sensitive method for the quantification of microgram quantities of protein utilizing the principle of protein-dye binding. Anal Biochem 72: 248-254, 1976.
11. Chomozynski P and Sacci N: Single-step method of RNA isolation by acid guanidine thiocyanate-phenol-chloroform extraction. Anal Biochem 162: 156-159, 1987.
12. Hanazawa S, Takeshita A and Kitano S: Retinoic acid suppression of c-fos gene inhibits expression of tumor necrosis factor-alpha-induced monocyte chemoattractant JE/MCP-1 in clonal osteoblastic MC3T3-E1 cells. J Biol Chem 269: 21379-21384, 1994.
13. Smith PM, Krohn RI, Hermanson GT, Mallia AK, Gartner FH, Provenzano MD, Fujimoto EK, Goeke NM, Olson BJ and Klenk DC: Measurement of protein using bicinchoninic acid. Anal Biochem 150: 76-85, 1985.
14. Klein E and Lukes V: Study of gas-phase O-H-bond dissociation enthalpies and ionization potentials of substituted phenols-applicability of ab initio and DFT/B3LYP methods. Chemical Physics 330: 515-525, 2006.
15. Hong J, Bose M, Ju J, Ryu JH, Chen X, Sang S, Lee MJ and Yang CS: Modulation of arachidonic acid metabolism by curcumin and related beta-diketone derivatives: effects on cytosolic phospholipase A(2), cyclooxygenases and 5-lipoxygenase. Carcinogenesis 25: 1671-1679, 2004.
16. Pan MH, Lin-Shiau SY and Lin JK: Comparative studies on the suppression of nitric oxide synthase by curcumin and its hydrogenated metabolites through down-regulation of IkappaB kinase and NFkappaB activation in macrophages. Biochem Pharmacol 60: 1665-1676, 2000.
17. Baeuerle PA and Baltimore D: I kappa B: a specific inhibitor of the NF-kappa B transcription factor. Science 242: 540-546, 1988.
18. Garg AK and Aggawal BB: Reactive oxygen intermediates in TNF signaling. Mol Immunol 39: 509-517, 2002.
19. Atsumi T, Fujisawa S and Tonosaki K: Relationship between intracellular ROS production and membrane mobility in curcumin- and tetrahydrocurcumin-treated human gingival fibroblasts and human submandibular gland carcinoma cells. Oral Dis 11: 236-242, 2005.
20. Fujisawa S, Atsumi T, Ishihara M and Kadoma Y: Cytotoxicity, ROS-generation activity and radical-scavenging activity of curcumin and related compounds. Anticancer Res 24: 563-569, 2004.
21. Li W, Tsubouchi R, Qiao S, Haneda M, Murakami K and Yoshino M: Inhibitory action of eugenol compounds on the production of nitric oxide in RAW264.7 macrophages. Biomed Res 27: 69-74, 2006.
22. Iwakubo M, Takami A, Okada Y, Kawata T, Tagami Y, Sato M, Sugiyama T, Fukushima K, Taya S, Amano M, Kaibuchi K and Iijima H: Design and synthesis of rho kinase inhibitors (III). Bioorg Med Chem 15: 1022-1033, 2007.
23. Yao JC, Duan WG, Yun Y, Liu de Q, Yan M, Jiang ZZ and Zhang LY: Screening method for nonsteroidal antiinflammatory drugs based on the cyclooxygenase 2 pathway activated by serum-free stimulation in A549 cells. Yakugaku Zasshi 127: 527-532, 2007 (in Japanese).
24. Mitchell JA, Akarasereenont P, Thiemermann C, Flower RJ and Vane JR: Selectivity of nonsteroidal antiinflammatory drugs as inhibitors of constitutive and inducible cyclooxygenase. Proc Natl Acad Sci USA 90: 11693-11697, 1993.
25. Chang MS, Chen BC, Yu MT, Sheu JR, Chen TF and Lin CH: Phorbol 12-myristate 13-acetate up-regulates cyclooxygenase-2 expression in human pulmonary epithelial cells via Ras, Raf-1, ERK, and NF-kappaB, but not p38 MAPK, pathways. Cell Signal 17: 299-310, 2005.
26. Ackerman WE 4th, Rovin BH and Kniss DA: Epidermal growth factor and interleukin-1 beta utilize divergent signaling pathways to synergistically up-regulate cyclooxygenase-2 gene expression in human amnion-derived WISH cells. Biol Reprod 71: 2079-2086, 2004.
27. Liontas A and Yeger H: Curcumin and resveratrol induce apoptosis and nuclear translocation and activation of p53 in human neuroblastoma. Anticancer Res 24: 987-998, 2004.
28. 2+ and the activation of caspase-3. Anticancer Res 26: 4379-4389, 2006.
29. Pari L and Amali DR: Protective role of tetrahydrocurcumin (THC) an active principle of turmeric on chloroquine-induced hepatotoxicity. J Pharm Pharm Sci 8: 115-123, 2005.
30. Somparn P, Phisalaphong C, Nakornchai S, Unchern S and Morales NP: Comparative antioxidant activities of curcumin and its demethoxy and hydrogenated derivatives. Biol Pharm Bull 30: 74-78, 2007.
31. Murugan P and Pari L: Antioxidant effect of tetrahydrocurcumin in streptozotocin-nicotinamide-induced diabetic rats. Life Sci 79: 1720-1728, 2006.
32. Murugan P and Pari L: Effect of tetrahydrocurcumin on lipid peroxidation and lipids in streptozotocin-nicotinamide-induced diabetic rats. Basic Clin Pharmacol Toxicol 99: 122-127, 2006.
33. Priyadarsini KI, Maity DK, Naik GH, Kumar MS, Unnikrishnan MK, Satav JG and Mohan H: Role of phenolic O-H and methylene hydrogen on the free radical reactions and antioxidant activity of curcumin. Free Radic Biol Med 35: 475-484, 2003.
34. Murakami Y, Hirata A, Ito S, Shoji M, Tanaka S, Yasui T, Machino M and Fujisawa S: Re-evaluation of cyclooxygenase-2-inhibiting activity of vanillin and guaiacol in macrophages stimulated with lipopolysaccharide. Anticancer Res 27: 801-807, 2007.
35. Fujisawa S, Ishihara M, Murakami Y, Atsumi T, Kadoma Y and Yokoe I: Predicting the biological activities of 2-methoxyphenol antioxidants: effects of dimers. In Vivo 21: 181-188, 2007.
36. Maynard AT, Huang M, Rice WG and Covell DG: Reactivity of the HIV-1 nucleocapsid P7 zinc finger domains from the perspective of density function theory. Proc Natl Acad Sci USA 95: 11578-11583, 1998.
37. Roy D, Sarkar U, Chattaraj P, Mitra A, Padmanabhan J, Subramanian V, Damme S and Bultinck P: Analyzing toxicity through electrophilicity. Mol Diver 10: 119-131, 2006.
38. Kobayashi S, Shinohara H, Tabata K, Yamamoto N and Miyai A: Stereo structure-controlled and electronic structure-controlled estrogen-like chemicals to design and develop non-estrogenic bisphenol A analogs based on chemical hardness concept. Chem Pharm Bull (Tokyo) 54: 1633-1638, 2006.