Synthesis and characterization of a metal complex containing naringin and Cu, and its antioxidant, antimicrobial, antiinflammatory and tumor cell cytotoxicity.
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 cytotoxicity activities than free naringin without reducing cell viability.
Pereira
Regina M S
RM
Department of Pharmacy, Bandeirante University of São Paulo, Rua Maria Cândida 1813, São Paulo, SP, Brazil. rpereira02@hotmail.com
Andrades
Norma E D
NE
Paulino
Niraldo
N
Sawaya
Alexandra C H F
AC
Eberlin
Marcos N
MN
Marcucci
Maria C
MC
Favero
Giovani Marino
GM
Novak
Estela Maria
EM
Bydlowski
Sérgio Paulo
SP
D000818:Animals; D000900:Anti-Bacterial Agents / Q000494:pharmacology*; D000893:Anti-Inflammatory Agents / Q000494:pharmacology*; D000975:Antioxidants / Q000494:pharmacology*; D001713:Biphenyl Compounds / Q000737:chemistry; D002453:Cell Cycle / Q000187:drug effects; D016923:Cell Death / Q000187:drug effects; D003300:Copper / Q000737:chemistry*; D004354:Drug Screening Assays, Antitumor; D044950:Flavanones / Q000008:administration & dosage / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D016166:Free Radical Scavengers / Q000737:chemistry; D006801:Humans; D006834:Hydrazines / Q000737:chemistry; D006863:Hydrogen-Ion Concentration; D020014:K562 Cells; D009682:Magnetic Resonance Spectroscopy; D008297:Male; D051379:Mice; D008826:Microbial Sensitivity Tests; D010851:Picrates; D021241:Spectrometry, Mass, Electrospray Ionization; D013056:Spectrophotometry, Ultraviolet
D000900:Anti-Bacterial Agents; D000893:Anti-Inflammatory Agents; D000975:Antioxidants; D001713:Biphenyl Compounds; D044950:Flavanones; D016166:Free Radical Scavengers; D006834:Hydrazines; D010851:Picrates; D003300:Copper; C004931:1,1-diphenyl-2-picrylhydrazyl; C005274:naringin