A SPECTROSCOPIC INVESTIGATION OF THE COMPLEX OF TURMERIC DYE WITH COPPER(II) IN AQUEOUS SOLUTION
Keywords:
Curcumin, spectrophotometry, complexation, copperAbstract
The structure of the complex formed between Cu(II) and curcumin in aqueous solution was investigated using UV-visible spectroscopy. The molar ratio method was applied to ascertain the stoichiometric composition of the complex in aqueous solution. The resulting stoichiometry forCu(II) to curcumin was 1:2. A structure for Cu(Cur)2 was proposed. Curcumin uses the β-diketone moiety as the binding site with copper(II) ion. In addition, IR spectra and diffuse reflectance UV-Vis spectra have been performed to support the experimental observations.
References
Annaraj, J.P., Ponvel, K.M., and Athappan, P.(2004). Synthesis, spectra and redox behavior of copper(II) complexes ofcurcumin diketimines as models for blue copper proteins. Transit. Metal Chem.,29(7):722–727.
Barik, A., Mishra B., Kunwar, A., Kadam, R.M.,Shen, L., Dutta, S., Padhye, S., Satpati,A.K., Zhang, H.Y., and Priyadarsini, K.I.(2007). Comparative study of copper(II)-curcumin complexes as superoxide dismutase mimics and free radical scavenger.Eur. J. Med. Chem., 42(4):431-439.
Bates, R. (2000). Organic Synthesis using Transition Metals. Sheffield Academic Press, Sheffield, UK, 190p.
Bernabé-Prineda. M., Ramírez-Silva M.T.,Romero-Romo, M., González-Vergara,E., and Rojas-Hernández, A. (2004).Determination of acidity constants of curcumin in aqueous solution and apparent rate constant of its decomposition.Spectrochim. Acta. A, 60(5):1091-1097.
Borsari, M., Ferrari, E., Grandi, R., andSaladini, M. (2002). Curcuminoids as potential new ion-chelating agents:spectroscopic, polarographic and potentiometric study on their Fe(II)complexing ability, Inorg. Chim. Acta,328(1):61-68.
Christie, R.M. (2001). Colour Chemistry.Royal Society of Chemistry, Cambridge,UK, p. 12-134.
Jayaprakasha, G.K., Jagan Mohan Rao, L.,and Sakariah, K.K. (2002). ImprovedHPLC for the determination of curcumin,demethoxycurcumin, and bisdemethoxycurcumin.J. Agric. Food Chem., 50(13):3663-3672.
Jayaprakasha, G.K., Jagan Mohan Rao, L.,and Sakariah, K.K. (2005). Chemistry and biological activities of C.longa. Trends Food Sci. Tech., 16(12):533-548.
Jiang, H., Timmermann, B.N., and Gang, D.R.(2006). Use of liquid chromatography electrospray ionization tandem mass spectrometry to identify diaryheptanoidsin turmeric (Curcuma longa L.) rhizome.J. Chromatogr. A, 1111(1):21-31.
Karlsen J., Mostad A., and Tønnesen H.H.(1988). Structural studies of curcuminoids.VI. Crystal structure of 1,7 Bis(4-hydroxyphenyl)-1,6-heptadiene-3,5-dione hydrate. Acta Chem. Scand.,42:23-27.
Moeyes, M. (1993). Natural dyeing in Thailand.Bangkok: White Lotus., Bangkok, Thailand, 212p.
Mohammadi, K., Thompson, K.H., Patrick,B.O., Storr, T., Martins, C., Polishchuk,E., Yuen, V.G., and McNeill, J.H. (2005).Synthesis and characterization of dual function vanadyl, gallium and indium curcumin complexes for medicinal applications, J. Inorg. Biochem., 99(11):2217-2225.
Popoola, A.V. (2000). Comparative fastness assessment performance of cellulosic fibers dyed using natural colorants. J.Appl. Polym. Sci., 77(4):752-755.
Shen, L., Zhang, H., and Ji, H. (2005). Atheoretical study on Cu(II)-chelating properties of curcumin and its implicationsfor curcumin as a multipotent agent tocombat Alzheimer’s desease. J. Mol.Struc-Theochem., 757(1-3):199-202.
Tønnesen, H.H. (1989). Studies on curcuminand curcuminoids XV. Catalytic effect ofdemethoxy and bisdemethoxy curcuminon the peroxidation of linoleic acid by15-lipoxygenase. Int. J. Pharm., 51(4):179–181.
Tønnesen H.H., Karlsen J., and Mostad A. (1982).Studies on curcumin and curcuminoids.XXXIX. Photophysical properties of bisdemethoxycurcumin. Acta Chem.Scand., 36:475-479.
Tønnesen, H.H., Karlsen, J., Mostad, A.,Pedersen, U., Rasmussen, P.B., andLawesson, S.O. (1983). Electro analytical study of the interaction between dsDNAand curcumin in the presence of copper(II).Acta Chem. Scand., 37(4-5):179-185.
Tønnesen, H.H. and Karlsen, J. (1992). Studieson curcumin and curcuminoids, XXII.Curcumin as reducing agent and as a radical scavenger, Int. J. Pharm., 87(1-3):79-87.
Tønnesen, H.H., Másson, M., and Loftsson,T. (2002). Studies of curcumin and curcuminoids. XXVII. Cyclodextrin complexation: solubility, chemical and photochemical stability. Int. J. Pharm.,244(1-3):127-135.
Tsatsaroni, E., Liakopoulou-Kyriakides, M.,and Eleftheriadis, I. (1998). Comparative study of dyeing properties of two yellow natural pigments-effects of enzymes and proteins. Dyes Pigments, 37(4):307-315.
Vajragupta, O., Boonchoong, P., Watanabe,H., Tohda, M., Kummasud, N., andSumanont,Y. (2003). Manganese complexes of curcumin and its derivatives: Evaluation for the radical scavenging ability and neuroprotective activity. Free Radical Biology & Medicine, 35(12):1632–1644.
Wang, Y.-J., Pan, M.-H., Cheng, A.-L., Lin,L.-I., Ho, Y.-S., Hsieh, C.-Y., and Lin,J.-K. (1997). Stability of curcumin inbuffer solutions and characterization ofits degradation products. J. Pharmaceut.Biomed., 15(12):1867-1876.
Welch, A.J. and Champman, S.K. (1993). The Chemistry of the Copper and ZincTriads. Royal Society of Chemistry, Cambridge, UK, 259p.
Yoshizumi, K. and Crews, P.C. (2003).Characteristics of fading of wool cloth dyed with selected natural dyestuffs on the basis of solar radiant energy. Dyes Pigments, 58(3):197-204.
Zhao, L., Chen, F., Zhao, G., Wang, Z., Liao, X.and Hu, X. (2005). Isomerization of trans-Astaxanthin induced by copper(II)ion in ethanol, J. Agric. Food Chem.,53(24):9620-9623.
