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Molecules 2007, 12(7), 1352-1366; doi:10.3390/12071352

Synthesis and Characterization of a Metal Complex Containing Naringin and Cu, and its Antioxidant, Antimicrobial, Antiinflammatory and Tumor Cell Cytotoxicity

1
Department of Pharmacy, Bandeirante University of São Paulo, Rua Maria Cândida 1813, São Paulo, SP, Brazil
2
Thomson Mass Spectrometry Laboratory, Institute of Chemistry, State University of Campinas, UNICAMP, P.O.Box 6154, 13084-971 Campinas, SP, Brazil
3
Fundação Pró-Sangue Hemocentro de São Paulo. Av. Dr. Eneas Carvalho de Aguiar 155 –1 andar, sl. l43, SP, Brazil
*
Author to whom correspondence should be addressed.
Received: 15 May 2007 / Revised: 20 June 2007 / Accepted: 3 July 2007 / Published: 9 July 2007
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Abstract

The antioxidant activity of flavonoids is believed to increase when they are coordinated with transition metal ions. However, the literature on this subject is contradictory and the outcome seems to largely depend on the experimental conditions. In order to understand the contribution of the metal coordination and the type of interaction between a flavonoid and the metal ion, in this study a new metal complex of Cu (II) with naringin was synthesized and characterized by FT-IR, UV-VIS, mass spectrometry (ESI-MS/MS), elemental analysis and 1H-NMR. The results of these analyses indicate that the complex has a Cu (II) ion coordinated via positions 4 and 5 of the flavonoid. The antioxidant, anti-inflammatory and antimicrobial activities of this complex were studied and compared with the activity of free naringin. The Naringin–Cu (II) complex 1 showed higher antioxidant, anti-inflammatory and tumor cell cytoxicity activities than free naringin without reducing cell viability.
Keywords: Naringin complexes;flavonoid;anti-inflammatory;antimicrobial and antioxidant activities Naringin complexes;flavonoid;anti-inflammatory;antimicrobial and antioxidant activities
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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MDPI and ACS Style

Pereira, R.M.; Andrades, N.E.; Paulino, N.; Sawaya, A.C.; Eberlin, M.N.; Marcucci, M.C.; Favero, G.M.; Novak, E.M.; Bydlowski, S.P. Synthesis and Characterization of a Metal Complex Containing Naringin and Cu, and its Antioxidant, Antimicrobial, Antiinflammatory and Tumor Cell Cytotoxicity. Molecules 2007, 12, 1352-1366.

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