Molecular orbital basis for yellow curry spice curcumin's prevention of Alzheimer's disease

Journal of Agricultural and Food Chemistry

Volumn 54, Issue 10, 2006, Pages 3512-3520

  Balasubramanian, Krishnan ^a,b,c  

^a LAWRENCE LIVERMORE NATIONAL LABORATORY   (United States)

^b CALIFORNIA STATE UNIVERSITY   (United States)

^c UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

Charges; Curcumin; Molecular orbital studies; Polar and hydrophobic features

Indexed keywords

ANTIOXIDANT; CURCUMIN; NONSTEROID ANTIINFLAMMATORY AGENT; PLANT EXTRACT;

ALZHEIMER DISEASE; ARTICLE; BINDING SITE; BIOLOGY; BLOOD BRAIN BARRIER; CHEMICAL STRUCTURE; CHEMISTRY; CURCUMA LONGA; HUMAN; METHODOLOGY; PHYTOTHERAPY; SPICE;

ALZHEIMER DISEASE; ANTI-INFLAMMATORY AGENTS, NON-STEROIDAL; ANTIOXIDANTS; BINDING SITES; BLOOD-BRAIN BARRIER; COMPUTATIONAL BIOLOGY; CURCUMA; CURCUMIN; HUMANS; MOLECULAR STRUCTURE; PHYTOTHERAPY; PLANT EXTRACTS; SPICES;

ARISTOLOCHIA WATSONII; CURCUMA LONGA;

EID: 33744918267     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf0603533     Document Type: Article

References (36)

1. Yang, F.; Lim, G. P.; Begum, A. N.; Ubeda, O. J.; Simmons, M. R.; Ambegaokar, S. S.; Chen, P.; Kayed, R.; Glabe, C. G. Frautschy, S. A.; Cole, G. M. Curcumin inhibits formation of amyloid β oligomers and fibrils, binds plaques, and reduces amyloid in vivo. J. Biol. Chem. 2004, 280, 5892-5901.
2. Weggen, S.; Eriksen, J. L.; Das, P.; Sagi, S. A.; Wang, R.; Pietrizik, C. U.; Findlay, K. A.; Smith, T. E.; Murphy, M. P.; Butler, T.; Kang, D. E.; Marquez-Sterling, N.; Golde, T. E.; Koo, E. H. A subset of NSAIDs lower amyloidogenic Aβ 42 independently of cyclooxygenase activity. Nature 2001, 414, 212-216.
3. Gasparini, L.; Rusconi, L.; Xu, H.; del Soldato, P.; Ongini, E. Modulation of β-amyloid metabolism by non-steroidal anti-inflammatory drugs in neuronal cell cultures. J. Neurochem. 2004, 88, 337-348.
4. Lim, G. P.; Chiu, T.; Yang, F.; Beech, W.; Frautschy, S. A.; Cole, G. M. The curry spice curcumin reduces oxidative damage and amyloid pathology in an Alzheimer transgenic mouse J. Neurosci. 2001, 21, 8370-8377.
5. Zsila, F.; Bikádi, Z.; Simonyi, M. Molecular basis of Cotton effects induced by the binding of curcumin to human serum albumin. Tetrahedron: Asymmetry 2003, 14, 2433-2444.
6. Rovner, S. L. Untangling Alzheimer's-cover story. Chem. Eng. News 2005, 83 (8, Feb 21), 38-45.
7. Masuda, T.; Toi, Y.; Bando, H.; Maekawa, T.; Takeda, Y.; Yamaguchi, H. Structural identification of new curcumin dimers and their contribution to the antioxidant mechanism of curcumin. J. Agric. Food Chem. 2002, 50, 2524-2530.
8. L and IAP, the release of cytochrome c and inhibition of Akt. Carcinogenesis 2003, 24, 1199-1208.
9. Moos, P. J.; Edes, K.; Mullally, J.; Fitzpatrick, J. Curcumin impairs tumor suppressor p53 function in colon cancer cells. Carcinogenesis 2004, 9, 1611-1617.
10. Rashmi, R.; Kumar, S.; Karunagaran, D. Human colon cancer cells lacking Bax resisit curcumin-induced apoptosis and Bax requirement is dispensable with ectopic expression of Smac or downregulation of Bcl-XI. Carcinogenisis 2005, 26, 713-723.
11. Khafif, A.; Schantz, S. P.; Chou, T. C.; Edelstein, D.; Sacks, P. G. Quantification of chemopreventive synergism between (-)-epigallocatechin-3- gallate and curcumin in normal, premaligannat and malignant human oral epithelial cells. Carcinogenisis 1998, 19, 419-424.
12. Balasubramanian, S.; Eckert, R. Green tea polyphenol snd curcumin inversely regulate human involucrin promoter activity via opposing effects on CCAAT/enhancer-binding protein function. J. Biol. Chem. 2004, 23, 24007-24014.
13. Van Erk, M. J.; Teuling, E.; Staal, Y. C. M.; Huybers, S.; van Bladeren, P. J.; Aarts, J. M. M. J. G.; van Ommen, B. Time-and dose-dependent effects of curcumin on gene expressio in human colon cancel cells J. Carcinogen. 2004, 3, 1-17.
14. Kim, M.-k.; Choi, G.-j.; Lee, H.-s. Fungicidal property of Curcuma longa L. rhizome-derived curcumin against phytopathogenic fungi in a greenhouse. J. Agric. Food Chem. 2003, 51, 1578-1581.
15. Fujisawa, S.; Atsumi, T.; Ishihara, M.; Kadoma, Y. Cyctotoxicity, ROS generation activity and radical-scavengining activity of curcumin and related compounds. Anticancer Res. 2004, 24, 563-569.
16. Jovanovic, S. V.; Steenken, S.; Boone, C. W.; Simic, M. G. H-atom transfer is a preferred antioxidant mechanism of curcumin. J. Am. Chem. Soc. 1999, 121, 9677-9681.
17. Zsila, F.; Bikádi, Z.; Simonyi, M. Unique, pH-dependent biphasic band shape of the visible circular dichroism of curcumin-serum albumin complex. Biochem. Biophys. Res. Commun. 2003, 301, 776-872.
18. Khopde, S. M.; Priyadharshini, K. I.; Palit, D. K.; Mukherjee, T. Effect of solvent on the excited-state photophysical properties of curcumin. Photochem. Photobiol. 2000, 72, 625-631.
19. Borsari, M.; Ferrari, E.; Grandi, R.; Saladani, M. Curcuminoids as potential new iron-chelating agents: spectroscopic, polarographic and potentiometric study on their Fe(III) complexing ability. Inorg. Chim. Acta 2002, 328, 61-68.
20. Balasubramanian, K. Two colorful applications of the PPP method. Int. J. Quantum Chem. 1990, 37, 449-464.
21. Balasubramanian, K. Theoretical calculations on the UV-visible spectra of the curcumin pigment in turmeric. Indian J. Chem. 1991, 30A, 61-65.
22. Wright, J. S. Predicting the antioxidant activity of curcumin and curcuminoids. J. Mol. Struct. (THEOCHEM) 2002, 591, 207-217.
23. Sun, Y. M.; Wang, R. X.; Yuan, S. L.; Lin, X. J.; Liu, C. B. Theoretical study of the antioxidant activity of curcumin. Chinese J. Chem. 2004, 22, 827-830.
24. Mazumder, A.; Neamati, N.; Sunder, S.; SchuLz, J.; Perez, H.; Eich, E.; Pommier, Y. Curcumin analogs with altered potencies against HIV-1 integrase as probes for biochemical mechanisms of drug action. J. Med. Chem. 1997, 40, 3057-3063.
25. Basak, S. C. Use of molecular complexity indices in predictive pharmacology and toxicology: a QSAR approach. Med. Sci. Res. 1987, 15, 605-640.
26. Basak, S. C.; Mills, D.; Gute, B. D.; Hawkins, D. Predicting mutagenicity of congeneric and diverse sets of chemicals using computed molecular descriptors: a hierarchical approach. Quantitative Structure-Activity Relationship (QSAR) Models of Mutagens and Carcinogens; Benigni, R., Ed.; CRC Press: Boca Raton, FL, 2003; Chapter 7, pp 207-234.
27. Dias, J. R Handbook of Polycyclic Aromatic Hydrocarbons; Elsevier: Amsterdam, The Netherlands, 1987.
28. Parr, R. G.; Yang, W. Density Functional Theory of Atoms and Molecules; Oxford University Press: New York, 1989.
29. Møller, C.; Plesset, M. S. Note on an approximation treatment for many-electron systems. Phys. Rev. 1934, 46, 618-622.
30. Becke, A. D. Density-functional thermochemistry. III. The role of exact exchange. J. Chem. Phys. 1993, 98, 5648-5652.
31. Cances, E.; Mennucci, B.; Tomasi, J. A new integral equation formalism for the polarizable continuum model: theoretical background and applications to isotropic and anisotropic dielectrics J. Chem. Phys. 1997, 107, 3032-3041.
32. Mennucci, B.; Cances, E.; Tomasi, J. Evaluation of solvent effects in isotropic and anisotropic dielectrics and in ionic solutions with a unified integral equation method: theoretical bases, computational implementation, and numerical applications. J. Phys. Chem. B 1997, 101, 10506-10517.
33. Mennucci, B.; Tomasi, J. Continuum solvation models: A new approach to the problem of solute's charge distribution and cavity boundaries. J. Chem. Phys. 1997, 106, 5151-5158.
34. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A., Jr.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S,; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Salvador, P.; Dannenberg, J. J.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Baboul, A. G.; Stefanov, B. B; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Andres, J. L.; Gonzalez, C.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 03, revision C.02; Gaussian, Inc.: Pittsburgh, PA, 2005.
35. Barclay, L. R. C.; Vinquist, M. R.; Mukai, K.; Goto, H.; Hashimoto, Y.; Tokunaga, A.; Uno, H. On the antioxidant mechanism of curcumin: classical methods are needed to determine antioxidant mechanism and activity. Org. Lett. 2000, 2, 2841-2843.
36. Mauge, J. T.; Alworth, W. L.; Payton, F. L. Curcumin and derivatives. Acta Crystallogr. 2004, C60, 608-610.