Abstract
The article describes the synthesis and characterisation of the Cr(III)-rutin complex along with an estimate of its antioxidant activity. The complex was characterised using elemental analysis, UV-VIS, IR, conductance data, thermal, and gravimetric analyses. In the UV-VIS study, a bathochromic shift of approximately 98 nm indicates the formation of a rutin complex by more than one chelating site. The FT-IR spectra clearly show the formation of the Cr—O bond between rutin and Cr(III) at 494 cm−1, while the thermal study shows the presence of eight coordinated water molecules in the complex. The gravimetric analysis quantitatively proves the presence of four chloride ions. From these data, the formula of the Cr(III)-rutin complex was deduced as [Cr2(C27H28O16)(H2O)8]Cl4. Moreover, the antioxidant study of the complex was evaluated by using 2,2′-diphenyl-1-picrylhydrazyl (DPPH) free-radical, ferric-reducing, and phosphomolybdenum assays, which show that the complex has a higher antioxidant activity than rutin.
Similar content being viewed by others
References
Abbasi, M. A., Zafar, A., Riaz, T., Rehman, A., Arshad, S., Shahwar, D., Jahangir, M., Siddiqui, S. Z., Shahzadi, T., & Ajaib, M. (2010). Evaluation of comparative antioxidant potential of aqueous and organic fractions of Ipomoea carnea. Journal of Medicinal Plants Research, 4, 1883–1887. DOI: 10.5897/jmpr10.287.
Aroua, M. K., Zuki, F. M., & Sulaiman, N. M. (2007). Removal of chromium ions from aqueous solutions by polymerenhanced ultrafiltration. Journal of Hazardous Material, 147, 752–758. DOI: 10.1016/j.jhazmat.2007.01.120.
Balasuriya, B. W. N., & Rupasinghe, H. P. V. (2011). Plant flavonoids as angiotensin converting enzyme inhibitors in regulation of hypertension. Functional Foods in Health and Disease, 5, 172–188.
Buer, C. S., Imin, N., & Djordjevic, M. A. (2010). Flavonoids: New roles for old molecules. Journal of Integrative Plant Biology, 52, 98–111. DOI: 10.1111/j.1744-7909.2010.00905.x.
Choudhary, A., Sharma, R., Nagar, M., Mohsin, M., & Meena, H. S. (2011). Synthesis, characterization and antioxidant activity of some transition metal complexes with terpenoid derivatives. Journal of the Chilean Chemical Society, 56, 911–917. DOI: 10.4067/s0717-97072011000400019.
de Mello, V. J., da Maia, J. R. S., de Oliveira, T. T., Nagern, T. J., Ardisson, J. D., & de Lima, G. M. (2004). Tin(IV) compounds derivatives of reaction between organotin(IV), SNCl4 and rutin trihydrate: Characterization and hypolipidemic effects. Main Group Metal Chemistry, 27, 309–321. DOI: 10.1515/mgmc.2004.27.6.309.
de Souza, R. F. V., Sussuchi, E. M., & de Giovani, W. F. (2003). Synthesis, electrochemical, spectral, and antioxidant properties of complexes of flavonoids with metal ions. Synthesis and Reactivity in Inorganic and Metal-Organic Chemistry, 33, 1125–1144. DOI: 10.1081/sim-120023482.
de Souza, R. F. V., & de Giovani, W. F. (2005). Synthesis, spectral and electrochemical properties of Al(III) and Zn(II) complexes with flavonoids. Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 61, 1985–1990. DOI: 10.1016/j.saa.2004.07.029.
Dehghan, G., & Khoshkam, Z. (2012). Tin(II)-quercetin complex: Synthesis, spectral characterization and antioxidant activity. Food Chemistry, 131, 422–426. DOI: 10.1016/j.foodchem.2011.08.074.
Dubey, R. K., Dubey, U. K., & Mishra, C. M. (2008). Synthesis and physicochemical characterization of some Schiff base complexes of chromium(III). Indian Journal of Chemistry, 47A, 1208–1212.
Eastmond, D. A., MacGregor, J. T., & Slesinski, R. S. (2008). Trivalent chromium: Assessing the genotoxic risk of an essential trace element and widely used human and animal nutritional supplement. Critical Reviews in Toxicology, 38, 173–190. DOI: 10.1080/10408440701845401.
Ebrahimzadeh, M. A., Nabavi, S. M., Nabavi, S., Eslami, B., & Rahmani, Z. (2010a). Antioxidant and antihaemolytic activities of the leaves of Kefe cumin (Laser trilobum L) umbelliferae. Tropical Journal of Pharmaceutical Research, 9, 441–449. DOI: 10.4314/tjpr.v9i5.61053.
Ebrahimzadeh, M. A., Nabavi, S. M., Nabavi, S. F., Bahramian, F., & Bekhradnia, A. R. (2010b). Antioxidant and free radical scavenging activity of H. Officinalis L. Var. Angustifolius, V. Odorata, B. Hyrcana and C. Speciosum. Pakistan Journal of Pharmaceutical Sciences, 23, 29–34.
Es-Safi, N. E., Ghidouche, S., & Ducrot, P. H. (2007). Flavonoids: Hemisynthesis, reactivity, characterization and free radical scavenging activity. Molecules, 12, 2228–2258. DOI: 10.3390/12092228.
Fathiazad, F., Delazar, A., Amiri, R., & Sarker, S. D. (2006). Extraction of flavonoids and quantification of rutin from waste tobacco leaves. Iranian Journal of Pharmaceutical Research, 3, 222–227.
Filipiak-Szok, A., Kurzawa, M., & Szłyk, E. (2012). Determination of anti-oxidant capacity and content of phenols, phenolic acids, and flavonols in Indian and European gooseberry. Chemical Papers, 66, 259–268. DOI: 10.2478/s11696-012-0151-5.
Gülçin, İ., Topal, F., Öztürk Sarıkaya, S. B., Bursal, E., Bilsel, G., & Gören, A. C. (2011). Polyphenol contents and antioxidant properties of medlar (Mespilus germanica L.). Records of Natural Products, 5, 158–175
Huang, D. J., Ou, B. X., & Prior, R. L. (2005). The chemistry behind antioxidant capacity assays. Journal of Agricultural and Food Chemistry, 53, 1841–1856. DOI: 10.1021/jf030723c.
Katz, S. A., & Salem, H. (1993). The toxicology of chromium with respect to its chemical speciation: A review. Journal of Applied Toxicology, 13, 217–224. DOI: 10.1002/jat.2550130 314.
Khade, B. C., Deore, P. M., & Arbad, B. R. (2011). Composition and stability of chromium metal complexes with drug salbutamol and amino acids. Pharma Science Monitor, 2, 73–86.
Koksal, E., Bursal, E., Dikici, E., Tozoglu, F., & Gulcin, I. (2011). Antioxidant activity of Melissa officinalis leaves. Journal of Medicinal Plants Research, 5, 217–222.
Krejpcio, Z. (2001). Essentiality of chromium for human nutrition and health. Polish Journal of Environmental Studies, 10, 399–404.
Kuntić, V. S., Malešev, D. L., Radović, Z. V., & Kosanić, M. M. (1998). Spectrophotometric investigation of uranil(II)-rutin complex in 70 ethanol. Journal of Agricultural and Food Chemistry, 46, 5139–5142. DOI: 10.1021/jf980376k.
Kuntić, V., Malešev, D., Radović, Z., & Vukojević, V. (2000). Spectrophotometric investigation of the complexing reaction between rutin and titanyloxalate anion in 50% ethanol. Monatshefte für Chemie/Chemical Monthly, 131, 769–777. DOI: 10.1007/s007060050024.
Lee, J. D. (1996). Concise inorganic chemistry (5th ed.). New Delhi, India: Blackwell Science.
Li, X. C., & Chen, C. (2012). Systematic evaluation on antioxidant of magnolol in vitro. International Research Journal of Pure and Applied Chemistry, 2, 68–76.
Limaye, A. S., Deore, G. B., Shinde, B. M., & Laware, S. L. (2010). Assessment of Adiantum trapeziforme L. for antioxidant activities. Asian Journal of Experimental Biological Sciences, 1, 79–84.
Lugasi, L., Hóvári, J., Sági, K. V., & Bíró, L. (2003). The role of antioxidant phytonutrients in the prevention of diseases. Acta Biologica Szegediensis, 47, 119–125.
Malešev, D., & Kuntić, V. (2007). Investigation of metal-flavonoid chelates and the determination of flavonoids via metal-flavonoid complexing reactions. Journal of Serbian Chemical Society, 72, 921–939. DOI: 10.2298/jsc0710921m.
Marwah, R. G., Fatope, M. O., Al Mahrooqi, R., Varma, G. B., Al Abadi, H., & Al-Burtamani, S. K. S. (2007). Antioxidant capacity of some edible and wound healing plants in Oman. Food Chemistry, 101, 465–470. DOI: 10.1016/j.foodchem.2006.02.001.
Medvidović-Kosanović, M., SamardŽić, M., Malatesti, N., & Sak-Bosnar, M. (2011). Electroanalytical characterization of a copper(II)-rutin complex. International Journal of Electrochemical Science, 6, 1075–1084.
Middleton, E., Jr., Kandaswami, C., & Theoharides, T. C. (2000). The effect of plant flavonoids on mammalian cells: Implications for inflammation, heart disease, and cancer. Pharmacological Reviews, 52, 673–751.
Niu, S. Y., Zhao, M., Hu, L. Z., & Zhang, S. H. (2008). Carbon nanotube-enhanced DNA biosensor for DNA hyberdization detection using rutin-Mn as electrochemical indicator. Sensors and Actuators B, 135, 200–205. DOI: 10.1016/j.snb.2008.08.022.
Panhwar, Q. K., Memon, S., & Bhanger, M. I. (2010). Synthesis, characterization, spectroscopic and antioxidation studies of Cu(II)-morin complex. Journal of Molecular Structure, 967, 47–53. DOI: 10.1016/j.molstruc.2009.12.037.
Prieto, P., Pineda, M., & Aguilar, M. (1999). Spectrophotometric quantitation of antioxidant capacity through the formation of a phosphomolybdenum complex: Specific application to the determination of vitamin E. Analytical Biochemistry, 269, 337–341. DOI: 10.1006/abio.1999.4019.
Raghu, K. L., Ramesh, C. K., Srinivasa, T. R., & Jamuna, K. S. (2011). Total antioxidant capacity in aqueous extracts of some common vegetables. Asian Journal of Experimental Biological Sciences, 2, 58–62.
Ray, N. K., Sripal, R. M., Chaluvadi, M. R., & Krishna, D. R. (2001). Bioflavonoids classification, pharmacological, biochemical effects and therapeutic potential. Indian Journal of Pharmacology, 33, 2–16.
Ren, W. Y., Qiao, Z. H., Wang, H. W., Zhu, L., & Zhang, L. (2003). Flavonoids: Promising anticancer agents. Medicinal Research Reviews, 23, 519–534. DOI: 10.1002/med.10033.
Sharma, D. K. (2006). Pharmacological properties of flavonoids including flavonolignans-integration of petrocrops with drug development from plants. Journal of Scientific and Industrial Research, 65, 477–484.
Sekhon, B. S., Kaushal, G. P., & Bhatia, I. S. (1983). Use of zirconium(IV) and antimony(III) for structural investigation of flavonoids. Microchimica Acta, 80, 421–427. DOI: 10.1007/bf01202020.
Shyam, K. R., Mruthunjaya, K., & Kumar, G. M. (2012). Preparation, characterization and antioxidant activities of gallic acid-phospholipids complex. International Journal of Research in Pharmaceutical Sciences, 2, 138–148.
Špačkov, V., & Pazourek, J. (2013). Identification of carbohydrate isomers in flavonoid glycosides after hydrolysis by hydrophilic interaction chromotogarphy. Chemical Papers, 67, 357–364. DOI: 10.2478/s11696-012-0302-8.
Tan, M. X., Liu, Y. C., Luo, X. J., Chen, Z. F., & Liang, H. (2011). Antioxidant activities of plumbagin and its Cu (II) complex. Bioinorganic Chemistry and Applications, 2011, 898726. DOI: 10.1155/2011/898726.
Tang, A. N., Jiang, D. Q., Jiang, Y., Wang, S. W., & Yan, X. P. (2004). Cloud point extraction for high-performance liquid chromatographic speciation of Cr(III) and Cr(VI) in aqueous solutions. Journal of Chromatography A, 1036, 183–188. DOI: 10.1016/j.chroma.2004.02.065.
Tian, Q. L., Liao, S. H., Lu, P., & Liu, L. J. (2006). Spectroscopic study on the interaction of Al3+ with flavonoids and BSA. Chinese Journal of Chemistry, 24, 1388–1390. DOI: 10.1002/cjoc.200690259.
Uivarosi, V., Barbuceanu, S. F., Aldea, V., Arama, C. C., Badea, M., Olar, R., & Marinescu, D. (2010). Synthesis, spectral and thermal studies of new rutin vanadyl complexes. Molecules, 15, 1578–1589. DOI: 10.3390/molecules15031578.
Yang, M. L., Yang, P. J., & Song, Y. M. (2005). Synthesis, characterization and interaction of transition metal complex of rutin with BSA and HAS. Chinese Journal of Inorganic Chemistry, 21, 483–489.
Yazdanbakhsh, M., Lotfian, N., & Tavakkoli, H. (2009). Synthesis and characterization of two novel trinuclear oxo-centered, of chromium and iron complexes containing unsaturated carboxylate bridging ligand. Bulletin of the Chemical Society of Ethiopia, 23, 463–466. DOI: 10.4314/bcse.v23i3.47672.
Zheng, L. J., Wu, Y. B., Wu, J. G., Tan, C. J., Yi, J., Chen, T. Q., & Wu, J. Z. (2012). Antioxidant activity of lotus (Nelumbo nucifera Gaertn.) receptacles of eleven cultivars grown in China. Journal of Medicinal Plants Research, 6, 1902–1911. DOI: 10.5897/jmpr11.1373.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Panhwar, Q.K., Memon, S. Synthesis, characterisation, and antioxidant study of Cr(III)-rutin complex. Chem. Pap. 68, 614–623 (2014). https://doi.org/10.2478/s11696-013-0494-6
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.2478/s11696-013-0494-6